# US 8,541,475 B2 · MAO-B inhibitors useful for treating obesity

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- Number: US 8,541,475 B2
- Document ID: US8541475B2
- Status: Granted
- Kind: B2
- Application number: 12/650,642
- Filed: 2009-12-31
- Published: 2010-07-01
- Granted: 2013-09-24
- Earliest claimed: 2005-06-02
- Assignees: Jenrin Discovery
- Applicants: John Francis McElroy; Robert J. Chorvat; Parthasarathi Rajagopalan
- Inventors: John Francis McElroy; Robert J. Chorvat; Parthasarathi Rajagopalan
- Web page: https://patentgrep.com/patent/US8541475B2

## CPC

- C07F 9/3808: {Acyclic saturated acids which can have further substituents on alkyl}
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 217/54: having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C 229/46: having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C 229/50: with amino groups and carboxyl groups bound to carbon atoms being part of the same condensed ring system
- C07C 235/06: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C 311/08: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07D 307/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07F 9/4006: {Esters of acyclic acids which can have further substituents on alkyl}
- C07C 2602/08: the other ring being five-membered, e.g. indane
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention provides novel compounds of formulae I and II: that are monoamine oxidase-B inhibitors, which can be useful in treating obesity, diabetes, and/or cardiometabolic disorders (e.g., hypertension, dyslipidemias, high blood pressure, and insulin resistance).

## Claims

### Claim 1

A method of treating a disease, comprising: administering to a mammal in need thereof a therapeutically effective amount of a compound of formula I or II, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the disease is selected from obesity, Type 2 diabetes, hypertension, dyslipidemia, high blood pressure, insulin resistance, and a combination thereof:
wherein:
R, at each occurrence, is independently selected from H, C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl;
R1 is selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, (CH2)mCO2R, C2-6 alkenyl-CO2R, CH2CH(NHAc)CO2R, CH2CH(NHR)CO2R, and, (CH2),nPO(OR)2;
A− is a counter ion;
V is selected from O−, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
X, X1, X2, and X3 are independently selected from H, OR, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, —CN, (CH2)nCO2R, (CH2)nCONR2, (CH2)nCN, O(CH2)nCN, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-6 alkenyl-CO2R, O(CH2)nPO(OR)2, NR—C2-4 alkenyl, NRSO2CH3, NR(CH2)nCO2R, NR(CH2)nCON(R)2, NR—C2-4 alkenyl-CO2R, NR(CH2)nPO(OR)2, NR(CH2)nSO2OR, SO2NRCH3, OCH2CHMCONRCH2CO2R, CH2-aryl, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2(CH2)nN+(CH3)3A−, O(CH2)n-biphenyl, O(CH2)n-biphenyl-(CH2)mCO2R, O(CH2)n-biphenyl-(CH2)mCN, O(CH2)n-biphenyl-(CH2)mCON(R)2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-(CH2)mCO2R, NR(CH2)n-biphenyl-(CH2)mCN, NR(CH2)n-biphenyl-(CH2)mCON(R)2, O(CH2)n-aryl, NR(CH2)n-aryl, O(CH2)n-aryl(CH2)m,CO2R, O(CH2)n-aryl-C2-6 alkenyl-CO2R, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-aryl(CH2)m-PO(OR)2, O(CH2)n-aryl-O(CH2)nCO2R, O(CH2)n-aryl-O—C2-6 alkenyl-CO2R, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, O(CH2)n-arylO(CH2)n-PO(OR)2, O(CH2)n-aryl-NR(CH2)nCO2R, O(CH2)n-aryl-NRC2-6 alkenyl-CO2R, O(CH2)n-aryl-NR(CH2)nCN, O(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)n-PO(OR)2, NR(CH2)n-aryl(CH2)mCO2R, NR(CH2)n-aryl-C2-6 alkenyl-CO2R, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)mCON(R)2, NR(CH2)n-aryl(CH2)m-PO(OR)2, NR(CH2)n-aryl-NR(CH2)nCO2R, NR(CH2)n-aryl-NR—C2-6 alkenyl-CO2R, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nPO(OR)2, NR(CH2)n-arylO(CH2)nCO2R, NR(CH2)n-aryl-O—C2-6 alkenyl-CO2R, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, and NR(CH2)n-arylO(CH2)nPO(OR)2, wherein aryl is substituted with 1-2 X4;
X4 is selected from H, OR, O—C2-6 alkenyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, nitro, —CN, C(O)NR2, NRSO2CH3, and, SO2N(R)C1-6alkyl;
Q is selected from H, OH, C1-6 alkoxy, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-6 alkenyl, O—C2-6 alkenyl-CO2R, OCH2CH2CONRCH2CO2R, OCH2CHMCONRCH2CO2R, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2CH(NHAc)CO2R, OCH2CH(NHR)CO2R, and O(CH2)n-aryl;
W is selected from H, CO2R, CON(R)2, CH2OH, CH2OC1-6 alkyl, CH2OC2-6 alkenyl, CH2O(CH2)nCO2R, CH2O(CH2)nCON(R)2, CH2O—C2-6 alkenyl-CO2R, CH2OCH2CH2CONRCH2CO2R, CH2OCH2CHMCONRCH2CO2R, CH2O(CH2)nPO(OR)2, CH2O(CH2)nSO2OR, CH2OCH2CH(NHAc)CO2R, CH2OCH2CH(NHR)CO2R, CH2O—C2-6 alkenyl, and CH2O(CH2)nCONH2, and CH2O(CH2)n-aryl;
M is independently selected from H, C1-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, and (CH2)n-aryl, wherein aryl is substituted with 1-2 X4;
m is independently selected from 0, 1, 2, 3, and 4; and,
n is independently selected from 1, 2, 3, and 4;
provided that at least one of X, X1, X2, and X3 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 2 (depends on 1)

A method of treating of claim 1, wherein the compound is of formula I1 or II1, or a stereoisomer or pharmaceutically acceptable salt thereof:

### Claim 3 (depends on 1)

A method of treating of claim 1, wherein the compound is of formula Ia, or a stereoisomer or pharmaceutically acceptable salt thereof:
wherein:
R, at each occurrence, is independently selected from H and C1-4 alkyl;
R1 is selected from H and C1-4 alkyl;
X and X1 are independently selected from H, OR, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, —CN, O(CH2)nCON(R)2, O—C2-4 alkenyl, NRSO2CH3, SO2NRCH3, CH2N(C1-4 alkyl)2, CH2-aryl, O(CH2)n-aryl, NR(CH2)n-aryl, O(CH2)n-aryl-(CH2)mCON(R)2, O(CH2)n-aryl-O(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-(CH2)mCON(R)2, NR(CH2)n-aryl-O(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-biphenyl, O(CH2)n-biphenyl-CN, O(CH2)n-biphenyl-CONH2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-CN, and NR(CH2)n-biphenyl-CONH2, wherein aryl is substituted with 1-2 X4;
X4 is selected from H, OH, C1-4 alkoxy, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, nitro, —CN, C(O)NR2, NRSO2CH3, and, SO2N(R)C1-6alkyl;
n is independently selected from 1, 2, and 3;
provided that at least one of X and X1 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 4 (depends on 3)

A method of of claim 3, wherein:
one of X and X1 is H and the other is selected from OH, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, —CN, C1-4 alkoxy, O(CH2)nCON(R)2, O—C2-4 alkenyl, NRSO2CH3, SO2NRCH3, CH2N(C1-4 alkyl)2, CH2-aryl, O(CH2)n-aryl, NR(CH2)n-aryl, O(CH2)n-aryl-(CH2)mCON(R)2, O(CH2)n-aryl-O(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-(CH2)mCON(R)2, NR(CH2)n-aryl-O(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-biphenyl, O(CH2)n-biphenyl-CN, O(CH2)n-biphenyl-CONH2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-CN, and NR(CH2)n-biphenyl-CONH2, wherein aryl is substituted with 1-2 X4;
provided that at least one of X and X1 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 5 (depends on 3)

A method of treating of claim 3, wherein the compound is of formula Ia1, or a stereoisomer or pharmaceutically acceptable salt thereof:

### Claim 6 (depends on 1)

A method of of claim 1, wherein the compound is of formula Ib, or a stereoisomer or pharmaceutically acceptable salt thereof:
wherein:
R, at each occurrence, is independently selected from H and C1-4 alkyl;
R1 is selected from H, C1-4 alkyl, (CH2)mCO2R, C2-4 alkenyl-CO2R, CH2CH(NHAc)CO2R, CH2CH(NHR)CO2R, and, (CH2),PO(OR)2;
X and X1 are independently selected from H, OR, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, —CN, O(CH2)nCON(R)2, O—C2-4 alkenyl, NRSO2CH3, SO2NRCH3, CH2N(C1-4 alkyl)2, CH2-aryl, O(CH2)n-aryl, NR(CH2)n-aryl, O(CH2)n-aryl-(CH2)mCON(R)2, O(CH2)n-aryl-O(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-(CH2)mCON(R)2, NR(CH2)n-aryl-O(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-biphenyl, O(CH2)n-biphenyl-CN, O(CH2)n-biphenyl-CONH2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-CN, NR(CH2)n-biphenyl-CONH2, wherein aryl is substituted with 1-2 X4;
X4 is selected from H, OH, C1-4 alkoxy, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, nitro, —CN, C(O)NR2, NRSO2CH3, and, SO2N(R)C1-6alkyl;
W is selected from H, CH2OH, CH2OC1-4 alkyl, CH2OC2-4 alkenyl, CH2O(CH2)nCO2R, CH2O—C2-4 alkenyl-CO2R, CH2O(CH2)nCON(R)2, CH2O(CH2)nPO(OR)2, and CH2O(CH2)n-aryl;
m is independently selected from 0, 1, and 2; and,
n is independently selected from 1, 2, and 3;
provided that at least one of X and X1 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 7 (depends on 6)

A method of treating of claim 6, wherein:
one of X and X1 is H and the other is selected from OH, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, —CN, C1-4 alkoxy, O(CH2)nCON(R)2, O—C2-4 alkenyl, NRSO2CH3, SO2NRCH3, CH2N(C1-4 alkyl)2, CH2-aryl, O(CH2)n-aryl, NR(CH2)n-aryl, O(CH2)n-aryl-(CH2)mCON(R)2, O(CH2)n-aryl-O(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-(CH2)mCON(R)2, NR(CH2)n-aryl-O(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-biphenyl, O(CH2)n-biphenyl-CN, O(CH2)n-biphenyl-CONH2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-CN, NR(CH2)n-biphenyl-CONH2, wherein aryl is substituted with 1-2 X4;
provided that at least one of X and X1 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 8 (depends on 6)

A method of treating of claim 6, wherein the compound is of formula Ib1, or a stereoisomer or pharmaceutically acceptable salt thereof:

### Claim 9 (depends on 1)

A method of treating of claim 1, wherein the compound is of formula Ic, or a stereoisomer or pharmaceutically acceptable salt thereof:
wherein:
R, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
R1 is selected from H and C1-4 alkyl;
X, X1, X2, and X3 are independently selected from H, OR, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, —CN, (CH2)nCO2R, (CH2)nCONR2, (CH2)nCN, O(CH2)nCN, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-4 alkenyl-CO2R, O(CH2)nPO(OR)2, NR—C2-4 alkenyl, NRSO2CH3, NR(CH2)nCO2R, NR(CH2)nCON(R)2, NR—C2-4 alkenyl-CO2R, NR(CH2)nPO(OR)2, NR(CH2)nSO2OR, SO2NRCH3, OCH2CHMCONRCH2CO2R, CH2-aryl, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2(CH2)nN+(CH3)3A−, O(CH2)n-biphenyl, O(CH2)n-biphenyl-(CH2)mCO2R, O(CH2)n-biphenyl-(CH2)mCN, O(CH2)n-biphenyl-(CH2)mCON(R)2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-(CH2)mCO2R, NR(CH2)n-biphenyl-(CH2)mCN, NR(CH2)n-biphenyl-(CH2)mCON(R)2, O(CH2)n-aryl, O(CH2)n-aryl(CH2)mCO2R, O(CH2)n-aryl-C2-4 alkenyl-CO2R, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-aryl(CH2)m-PO(OR)2, O(CH2)n-aryl-O(CH2)nCO2R, O(CH2)n-aryl-O—C2-4 alkenyl-CO2R, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, O(CH2)n-arylO(CH2)n-PO(OR)2, O(CH2)n-aryl-NR(CH2)nCO2R, O(CH2)n-aryl-NRC2-4alkenyl-CO2R, O(CH2)n-aryl-NR(CH2)nCN, O(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)n-PO(OR)2, NR(CH2)n-aryl(CH2)mCO2R, NR(CH2)n-aryl-C2-4 alkenyl-CO2R, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)mCON(R)2, NR(CH2)n-aryl(CH2)m-PO(OR)2, NR(CH2)n-aryl-NR(CH2)nCO2R, NR(CH2)n-aryl-NR—C2-4 alkenyl-CO2R, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nPO(OR)2, NR(CH2)n-arylO(CH2)nCO2R, NR(CH2)n-aryl-O—C2-4 alkenyl-CO2R, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, and NR(CH2)n-arylO(CH2)nPO(OR)2, wherein is substituted with 1-2 X4 ;
X4 is selected from H, OR, C1-4 alkoxy, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, nitro, —CN, C(O)NR2, NRSO2CH3, and, SO2N(R)C1-6alkyl;
A− is selected from Cl and Br;
M is independently selected from H, C1-4 alkyl, C3-6 cycloalkyl, C2-4 alkenyl, C2-4 alkynyl, aryl, and (CH2)n-aryl; and,
m is independently selected from 0, 1, and 2; and,
n is independently selected from 1, 2, and 3;
provided that at least one of X, X1, X2, and X3 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 10 (depends on 9)

A method of treating of claim 9, wherein:
three of X, X1, X2, and X3 are H and the fourth is selected from OH, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, C1-4 alkoxy, —CN, (CH2)nCO2R, (CH2)nCONR2, (CH2)nCN, O(CH2)nCN, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-4 alkenyl-CO2R, O(CH2)nPO(OR)2, NR—C2-4 alkenyl, NRSO2CH3, NR(CH2)nCO2R, NR(CH2)nCON(R)2, NR—C2-4 alkenyl-CO2R, NR(CH2)nPO(OR)2, NR(CH2)nSO2OR, SO2NRCH3, OCH2CHMCONRCH2CO2R, CH2-aryl, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2(CH2)nN+(CH3)3A−, O(CH2)n-biphenyl, O(CH2)n-biphenyl-(CH2)mCO2R, O(CH2)n-biphenyl-(CH2)mCN, O(CH2)n-biphenyl-(CH2)mCON(R)2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-(CH2)mCO2R, NR(CH2)n-biphenyl-(CH2)mCN, NR(CH2)n-biphenyl-(CH2)mCON(R)2, O(CH2)n-aryl, O(CH2)n-aryl(CH2)mCO2R, O(CH2)n-aryl-C2-4 alkenyl-CO2R, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-aryl(CH2)m-PO(OR)2, O(CH2)n-aryl-O(CH2)nCO2R, O(CH2)n-aryl-O—C2-4 alkenyl-CO2R, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, O(CH2)n-arylO(CH2)n-PO(OR)2, O(CH2)n-aryl-NR(CH2)nCO2R, O(CH2)n-aryl-NRC2-4 alkenyl-CO2R, O(CH2)n-aryl-NR(CH2)nCN, O(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)n-PO(OR)2, NR(CH2)n-aryl(CH2)mCO2R, NR(CH2)n-aryl-C2-4 alkenyl-CO2R, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)n,CON(R)2, NR(CH2)n-aryl(CH2)m-PO(OR)2, NR(CH2)n-aryl-NR(CH2)nCO2R, NR(CH2)n-aryl-NR—C2-4 alkenyl-CO2R, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nPO(OR)2, NR(CH2)n-arylO(CH2)nCO2R, NR(CH2)n-aryl-O—C2-4 alkenyl-CO2R, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, and NR(CH2)n-arylO(CH2)nPO(OR)2, O(CH2)n— wherein aryl is substituted with 1-2 X4;
provided that at least one of X, X1, X2, and X3 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 11 (depends on 9)

A method of treating of claim 9, wherein the compound is of formula Ic1, or a stereoisomer or pharmaceutically acceptable salt thereof:

### Claim 12 (depends on 1)

A method of treating of claim 1, wherein the compound is of formula Id, or a stereoisomer or pharmaceutically acceptable salt thereof:
wherein:
R, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
R1 is selected from H, C1-4 alkyl, (CH2)mCO2R, (CH2)nPO(OR)2, C2-4 alkenyl, and C2-4 alkynyl;
X, X1, and X2 are independently selected from H, OR, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, O(CH2)nCON(R)2, O—C2-4 alkenyl, NRSO2CH3, SO2NRCH3, CH2N(C1-4 alkyl)2, CH2-aryl, O(CH2)n-aryl, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)mCON(R)2, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-biphenyl, O(CH2)n-biphenyl-CN, O(CH2)n-biphenyl-CONH2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-CN, and NR(CH2)n-biphenyl-CONH2, wherein aryl is substituted with 1-2 X4;
X4 is selected from H, OH, C1-6 alkoxy C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, nitro, —CN, C(O)NR2, NRSO2CH3, and, SO2N(R)C1-6alkyl;
Q is selected from OH, C1-4 alkoxy, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-4 alkenyl, O—C2-4 alkenyl-CO2R, OCH2CH2CONRCH2CO2R, OCH2CHMCONRCH2CO2R, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2CH(NHAc)CO2R, OCH2CH(NHR)CO2R, and O(CH2)n-aryl;
M is independently selected from H, C1-4 alkyl, C3-6 cycloalkyl, C2-4 alkenyl, C2-4 alkynyl, aryl, and (CH2)n-aryl; and,
m is independently selected from 0, 1, and 2; and,
n is independently selected from 1, 2, and 3;
provided that at least one of X, X1, and X2 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 13 (depends on 12)

A method of treating of claim 12, wherein:
two of X, X1, and X2 are H and the third is selected from OH, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, C1-4 alkoxy, O(CH2)nCON(R)2, O—C2-4 alkenyl, NRSO2CH3, SO2NRCH3, CH2N(C1-4 alkyl)2, CH2-aryl, O(CH2)n-aryl, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)mCON(R)2, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-biphenyl, O(CH2)n-biphenyl-CN, O(CH2)n-biphenyl-CONH2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-CN, and NR(CH2)n-biphenyl-CONH2, wherein aryl is substituted with 1-2 X4;
provided that at least one of X, X1, and X2 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 14 (depends on 12)

A method of treating of claim 12, wherein the compound is of formula Id1, or a stereoisomer or pharmaceutically acceptable salt thereof:

### Claim 15 (depends on 1)

A method of treating of claim 1, wherein the compound is of formula IIa, or a stereoisomer or pharmaceutically acceptable salt thereof:
wherein:
R, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
R1 is selected from H and C1-4 alkyl;
A− is selected from Cl− and Br−;
V is selected from O−, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
X and X1 are independently selected from H, OR, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, O(CH2)nCON(R)2, O—C2-4 alkenyl, NRSO2CH3, SO2NRCH3, CH2-aryl, O(CH2)n-aryl, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)mCON(R)2, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-biphenyl, O(CH2)n-biphenyl-CN, O(CH2)n-biphenyl-CONH2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-CN, and NR(CH2)n-biphenyl-CONH2, wherein aryl is substituted with 1-2 X4;
X4 is selected from H, OR, C1-6 alkoxy C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, nitro, —CN, C(O)NR2, NRSO2CH3, and, SO2N(R)C1-6alkyl;
n is independently selected from 1, 2, and 3;
provided that at least one of X and X1 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 16 (depends on 15)

A method of treating of claim 15, wherein:
one of X and X1 is H and the other is selected from OH, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halogen, CF3, C1-4 alkoxy, O(CH2)nCON(R)2, O—C2-4 alkenyl, NRSO2CH3, SO2NRCH3, CH2-aryl, O(CH2)n-aryl, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)mCON(R)2, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-biphenyl, O(CH2)n-biphenyl-CN, O(CH2)n-biphenyl-CONH2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-CN, and NR(CH2)n-biphenyl-CONH2, wherein aryl is substituted with 1-2 X4;
provided that at least one of X and X1 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 17 (depends on 15)

A method of treating of claim 15, wherein the compound is of formula IIa1, or a stereoisomer or pharmaceutically acceptable salt thereof:

### Claim 18

A method of treating a disease, comprising: administering to a mammal in need thereof a therapeutically effective amount of a compound of formula I or II or a pharmaceutically acceptable salt form thereof, wherein the disease is a co-morbidty of obesity selected from Type 2 diabetes, Metabolic Syndrome, dementia, hypertension, pulmonary hypoventilation syndrome, coronary artery disease, arterial sclerotic disease, and high cholesterol:
wherein:
R, at each occurrence, is independently selected from H, C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl;
R1 is selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, (CH2)mCO2R, C2-6 alkenyl-CO2R, CH2CH(NHAc)CO2R, CH2CH(NHR)CO2R, and, (CH2)nPO(OR)2;
A− is a counter ion;
V is selected from O−, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
X, X1, X2, and X3 are independently selected from H, OR, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, —CN, (CH2)nCO2R, (CH2)nCONR2, (CH2)nCN, O(CH2)nCN, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-6 alkenyl-CO2R, O(CH2)nPO(OR)2, NR—C2-4 alkenyl, NRSO2CH3, NR(CH2)nCO2R, NR(CH2)nCON(R)2, NR—C2-4 alkenyl-CO2R, NR(CH2)nPO(OR)2, NR(CH2)nSO2OR, SO2NRCH3, OCH2CHMCONRCH2CO2R, CH2-aryl, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2(CH2)nN+(CH3)3A−, O(CH2)n-biphenyl, O(CH2)n-biphenyl-(CH2)mCO2R, O(CH2)n-biphenyl-(CH2)mCN, O(CH2)n-biphenyl-(CH2)mCON(R)2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-(CH2)mCO2R, NR(CH2)n-biphenyl-(CH2)mCN, NR(CH2)n-biphenyl-(CH2)mCON(R)2, O(CH2)n-aryl, NR(CH2)n-aryl, O(CH2)n-aryl(CH2)mCO2R, O(CH2)n-aryl-C2-6 alkenyl-CO2R, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-aryl(CH2)m-PO(OR)2, O(CH2)n-aryl-O(CH2)nCO2R, O(CH2)n-aryl-O—C2-6 alkenyl-CO2R, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, O(CH2)n-arylO(CH2)n-PO(OR)2, O(CH2)n-aryl-NR(CH2)nCO2R, O(CH2)n-aryl-NRC2-6 alkenyl-CO2R, O(CH2)n-aryl-NR(CH2)nCN, O(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)n-PO(OR)2, NR(CH2)n-aryl(CH2)mCO2R, NR(CH2)n-aryl-C2-6 alkenyl-CO2R, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)mCON(R)2, NR(CH2)n-aryl(CH2)m-PO(OR)2, NR(CH2)n-aryl-NR(CH2)nCO2R, NR(CH2)n-aryl-NR—C2-6 alkenyl-CO2R, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nPO(OR)2, NR(CH2)n-arylO(CH2)nCO2R, NR(CH2)n-aryl-O—C2-6 alkenyl-CO2R, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, and NR(CH2)n-arylO(CH2)nPO(OR)2, wherein aryl is substituted with 1-2 X4;
X4 is selected from H, OR, O—C2-6 alkenyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, nitro, —CN, C(O)NR2, NRSO2CH3, and, SO2N(R)C1-6alkyl;
Q is selected from H, OH, C1-6 alkoxy, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-6 alkenyl, O—C2-6 alkenyl-CO2R, OCH2CH2CONRCH2CO2R, OCH2CHMCONRCH2CO2R, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2CH(NHAc)CO2R, OCH2CH(NHR)CO2R, and O(CH2)n-aryl;
W is selected from H, CO2R, CON(R)2, CH2OH, CH2OC1-6 alkyl, CH2OC2-6 alkenyl, CH2O(CH2)nCO2R, CH2O(CH2)nCON(R)2, CH2O—C2-6 alkenyl-CO2R, CH2OCH2CH2CONRCH2CO2R, CH2OCH2CHMCONRCH2CO2R, CH2O(CH2)nPO(OR)2, CH2O(CH2)nSO2OR, CH2OCH2CH(NHAc)CO2R, CH2OCH2CH(NHR)CO2R, CH2O—C2-6 alkenyl, and CH2O(CH2)nCONH2, and CH2O(CH2)n-aryl;
M is independently selected from H, C1-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, and (CH2)n-aryl, wherein aryl is substituted with 1-2 X4;
m is independently selected from 0, 1, 2, 3, and 4; and,
n is independently selected from 1, 2, 3, and 4;
provided that at least one of X, X1, X2, and X3 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 19

A method of treating a disease, comprising: administering to a mammal in need thereof a therapeutically effective amount of a compound of formula I or II or a pharmaceutically acceptable salt form thereof, wherein the disease is a CNS disorder selected from Parkinson's disease, depression, anxiety, panic attack, social phobia, schizophrenia, anorexia, and neuropathic pain:
wherein:
R, at each occurrence, is independently selected from H, C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl;
R1 is selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, (CH2)mCO2R, C2-6 alkenyl-CO2R, CH2CH(NHAc)CO2R, CH2CH(NHR)CO2R, and, (CH2)nPO(OR)2;
A− is a counter ion;
V is selected from O−, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
X, X1, X2, and X3 are independently selected from H, OR, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, —CN, (CH2)nCO2R, (CH2)nCONR2, (CH2)nCN, O(CH2)nCN, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-6 alkenyl-CO2R, O(CH2)nPO(OR)2, NR—C2-4 alkenyl, NRSO2CH3, NR(CH2)nCO2R, NR(CH2)nCON(R)2, NR—C2-4 alkenyl-CO2R, NR(CH2)nPO(OR)2, NR(CH2)nSO2OR, SO2NRCH3, OCH2CHMCONRCH2CO2R, CH2-aryl, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2(CH2)nN+(CH3)3A−, O(CH2)n-biphenyl, O(CH2)n-biphenyl-(CH2)mCO2R, O(CH2)n-biphenyl-(CH2)mCN, O(CH2)n-biphenyl-(CH2)mCON(R)2, NR(CH2)n-biphenyl, NR(CH2)n-biphenyl-(CH2)mCO2R, NR(CH2)n-biphenyl-(CH2)mCN, NR(CH2)n-biphenyl-(CH2)mCON(R)2, O(CH2)n-aryl, NR(CH2)n-aryl, O(CH2)n-aryl(CH2)mCO2R, O(CH2)n-aryl-C2-6 alkenyl-CO2R, O(CH2)n-aryl(CH2)mCN, O(CH2)n-aryl(CH2)mCON(R)2, O(CH2)n-aryl(CH2)m-PO(OR)2, O(CH2)n-aryl-O(CH2)nCO2R, O(CH2)n-aryl-O—C2-6 alkenyl-CO2R, O(CH2)n-arylO(CH2)nCN, O(CH2)n-arylO(CH2)nCON(R)2, O(CH2)n-arylO(CH2)n-PO(OR)2, O(CH2)n-aryl-NR(CH2)nCO2R, O(CH2)n-aryl-NRC2-6 alkenyl-CO2R, O(CH2)n-aryl-NR(CH2)nCN, O(CH2)n-aryl-NR(CH2)nCON(R)2, O(CH2)n-aryl-NR(CH2)n-PO(OR)2, NR(CH2)n-aryl(CH2)mCO2R, NR(CH2)n-aryl-C2-6 alkenyl-CO2R, NR(CH2)n-aryl(CH2)mCN, NR(CH2)n-aryl(CH2)mCON(R)2, NR(CH2)n-aryl(CH2)m-PO(OR)2, NR(CH2)n-aryl-NR(CH2)nCO2R, NR(CH2)n-aryl-NR—C2-6 alkenyl-CO2R, NR(CH2)n-aryl-NR(CH2)nCN, NR(CH2)n-aryl-NR(CH2)nCON(R)2, NR(CH2)n-aryl-NR(CH2)nPO(OR)2, NR(CH2)n-arylO(CH2)nCO2R, NR(CH2)n-aryl-O—C2-6 alkenyl-CO2R, NR(CH2)n-arylO(CH2)nCN, NR(CH2)n-aryl-O(CH2)nCON(R)2, and NR(CH2)n-arylO(CH2)nPO(OR)2, wherein aryl is substituted with 1-2 X4;
X4 is selected from H, OR, O—C2-6 alkenyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, nitro, —CN, C(O)NR2, NRSO2CH3, and, SO2N(R)C1-6alkyl;
Q is selected from H, OH, C1-6 alkoxy, O(CH2)nCO2R, O(CH2)nCON(R)2, O—C2-6 alkenyl, O-C2-6 alkenyl-CO2R, OCH2CH2CONRCH2CO2R, OCH2CHMCONRCH2CO2R, O(CH2)nPO(OR)2, O(CH2)nSO2OR, OCH2CH(NHAc)CO2R, OCH2CH(NHR)CO2R, and O(CH2)n-aryl;
W is selected from H, CO2R, CON(R)2, CH2OH, CH2OC1-6 alkyl, CH2OC2-6 alkenyl, CH2O(CH2)nCO2R, CH2O(CH2)nCON(R)2, CH2O—C2-6 alkenyl-CO2R, CH2OCH2CH2CONRCH2CO2R, CH2OCH2CHMCONRCH2CO2R, CH2O(CH2)nPO(OR)2, CH2O(CH2)nSO2OR, CH2OCH2CH(NHAc)CO2R, CH2OCH2CH(NHR)CO2R, CH2O—C2-6 alkenyl, and CH2O(CH2)nCONH2, and CH2O(CH2)n-aryl;
M is independently selected from H, C1-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, and (CH2)n-aryl, wherein aryl is substituted with 1-2 X4;
m is independently selected from 0, 1, 2, 3, and 4; and,
n is independently selected from 1, 2, 3, and 4;
provided that at least one of X, X1, X2, and X3 is other than H, alkyl, alkoxy, hydroxyl, CF3, and halo.

### Claim 20 (depends on 1)

The method of claim 1, wherein the compound is a compound selected from Tables A-C or a stereoisomer or pharmaceutically acceptable salt thereof:
TABLE A
All compounds racemic
Number
X
R
1
CH2C6H5
H
2
CH2CH2C6H5
H
3
CH2CO2Et
CH3
4
CH2CO2Et
H
TABLE B
All compounds racemic
Number
X
R
5
CH2C6H5
H
6
CH2CH2C6H5
H
7
CH2C6H5
CH3
8
CH2CO2Et
H
9
CH2CO2Et
CH3
10
CH2CO2H
CH3
11
(CH2)4CO2Et
H
12
CH2CH═CHCO2Et
CH3
13
CH2CH═CHCO2Et
H
14
CH2C6H5CO2Me(4)
CH3
15
CH2C6H5CO2Me(4)
H
16
CH2C6H5CONH2(4)
H
17
CH2C6H5CO2Me(3)
CH3
18
CH2C6H5CO2Me(3)
H
19
CH2C6H5CO2H(3)
H
20
CH2C6H5CONH2(3)
H
21
CH2C6H5CH2CO2Me(4)
H
22
CH2C6H5CH2CO2H(4)
H
23
CH2C6H5OCH2CO2Et(4)
H
24
CH2C6H5OCH2CONH2(4)
H
26
CH2CH2CH2PO(OEt)2
H
TABLE C
All compounds racemic
Number
X
R
27
CH2C6H5
H
28
CH2C6H5
CH3
29
CH2CH2C6H5
H
30
CH2CO2Et
CH3
31
CH2CH═CHCO2Et
CH3
32
CH2CH═CHCO2Et
H
33
CH2C6H5CO2Me(4)
CH3
34
CH2C6H5CO2Me(4)
H
35
CH2C6H5CO2Me(3)
H
36
CH2C6H5OCH2CN(3)
H
37
CH2C6H5CN(3)
H
38
CH2C6H5CONH2(3)
H

### Claim 21 (depends on 1)

The method of claim 1, wherein the compound is a compound selected from Tables I-Vb and VIIa-VIIc or a stereoisomer or a pharmaceutically acceptable salt thereof:
TABLE I
Ex. #
X
X1
R
R1
21
OCH2C6H5
H
CH3
H
22
OCH2C6H5
H
H
H
23
OCH2C6H5
H
CH3
CH3
24
OCH2C6H5
H
H
CH3
25
H
OCH2C6H5
CH3
H
26
H
OCH2C6H5
H
H
27
H
OCH2C6H5
CH3
CH3
28
H
OCH2C6H5
H
CH3
29
OCH2C6H5
H
CH3
H
30
OCH2C6H5
H
H
H
31
OCH2C6H5
H
CH3
CH3
32
OCH2C6H5
H
H
CH3
33
OCH2CH2C6H5
H
CH3
H
34
OCH2CH2C6H5
H
H
H
35
OCH2CH2C6H5
H
CH3
CH3
36
OCH2CH2C6H5
H
H
CH3
37
H
OCH2CH2C6H5
CH3
H
38
H
OCH2CH2C6H5
H
H
39
H
OCH2CH2C6H5
CH3
CH3
40
H
OCH2CH2C6H5
H
CH3
41
OCH2CH═CH2
H
CH3
H
42
OCH2CH═CH2
H
H
H
43
OCH2CH═CH2
H
CH3
CH3
44
OCH2CH═CH2
H
H
CH3
45
H
OCH2CH═CH2
CH3
H
46
H
OCH2CH═CH2
H
H
47
H
OCH2CH═CH2
CH3
CH3
48
H
OCH2CH═CH2
H
CH3
49
OCH2CONH2
H
CH3
H
50
OCH2CONH2
H
H
H
51
OCH2CONH2
H
CH3
CH3
52
OCH2CONH2
H
H
CH3
53
H
OCH2CONH2
CH3
H
54
H
OCH2CONH2
H
H
55
H
OCH2CONH2
CH3
CH3
56
H
OCH2CONH2
H
CH3
69
NH2
H
CH3
H
70
NH2
H
H
H
71
NH2
H
CH3
CH3
72
NH2
H
H
CH3
73
NHSO2CH3
H
CH3
H
74
NHSO2CH3
H
H
H
75
NHSO2CH3
H
CH3
CH3
76
NHSO2CH3
H
H
CH3
TABLE IIa
Ex. #
X
X1
R1
1.
OCH2CH═CH2
H
CO2CH2CH3
2.
OCH2CH═CH2
H
CO2H
3.
OCH2C6H5
H
CO2CH2CH3
4.
OCH2C6H5
H
CO2H
5.
OCH2CH2C6H5
H
CO2CH2CH3
6.
OCH2CH2C6H5
H
CO2H
7.
OCH2CONH2
H
CO2CH2CH3
8.
OCH2CONH2
H
CO2H
9.
NH2
H
CO2CH2CH3
10.
NH2
H
CO2H
11.
NHSO2CH3
H
CO2CH2CH3
12.
NHSO2CH3
H
CO2H
13.
H
OCH2CH═CH2
CO2CH2CH3
14.
H
OCH2CH═CH2
CO2H
15.
H
OCH2C6H5
CO2CH2CH3
16.
H
OCH2C6H5
CO2H
17.
H
OCH2CH2C6H5
CO2CH2CH3
18.
H
OCH2CH2C6H5
CO2H
19.
H
OCH2CONH2
CO2CH2CH3
20.
H
OCH2CONH2
CO2H
21.
OCH2CH═CH2
H
CH2CO2CH2CH3
22.
OCH2CH═CH2
H
CH2CO2H
23.
OCH2C6H5
H
CH2CO2CH2CH3
24.
OCH2C6H5
H
CH2CO2H
25.
OCH2CH2C6H5
H
CH2CO2CH2CH3
26.
OCH2CH2C6H5
H
CH2CO2H
27.
OCH2CONH2
H
CH2CO2CH2CH3
28.
OCH2CONH2
H
CH2CO2H
29.
NH2
H
CH2CO2CH2CH3
30.
NH2
H
CH2CO2H
31.
NHSO2CH3
H
CH2CO2CH2CH3
32.
NHSO2CH3
H
CH2CO2H
33.
H
OCH2CH═CH2
CH2CO2CH2CH3
34.
H
OCH2CH═CH2
CH2CO2H
35.
H
OCH2C6H5
CH2CO2CH2CH3
36.
H
OCH2C6H5
CH2CO2H
37.
H
OCH2CH2C6H5
CH2CO2CH2CH3
38.
H
OCH2CH2C6H5
CH2CO2H
39.
H
OCH2CONH2
CH2CO2CH2CH3
40.
H
OCH2CONH2
CH2CO2H
41.
OCH2CH═CH2
H
CH2CO2CH2CH2CH3
42.
OCH2CH═CH2
H
CH2CH2CO2H
43.
OCH2C6H5
H
CH2CH2CO2CH2CH3
44.
OCH2C6H5
H
CH2CH2CO2H
45.
OCH2CH2C6H5
H
CH2CO2CH2CH2CH3
46.
OCH2CH2C6H5
H
CH2CH2CO2H
47.
OCH2CONH2
H
CH2CH2CO2CH2CH3
48.
OCH2CONH2
H
CH2CH2CO2H
49.
NH2
H
CH2CO2CH2CH2CH3
50.
NH2
H
CH2CH2CO2H
51.
NHSO2CH3
H
CH2CH2CO2CH2CH3
52.
NHSO2CH3
H
CH2CH2CO2H
53.
H
OCH2CH═CH2
CH2CO2CH2CH2CH3
54.
H
OCH2CH═CH2
CH2CH2CO2H
55.
H
OCH2C6H5
CH2CH2CO2CH2CH3
56.
H
OCH2C6H5
CH2CH2CO2H
57.
H
OCH2CH2C6H5
CH2CO2CH2CH2CH3
58.
H
OCH2CH2C6H5
CH2CH2CO2H
59.
H
OCH2CONH2
CH2CH2CO2CH2CH3
60.
H
OCH2CONH2
CH2CH2CO2H
61.
OCH2CH═CH2
H
CH2CH2PO(OCH2CH3)2
62.
OCH2CH═CH2
H
CH2CH2PO(OH)2
63.
OCH2C6H5
H
CH2CH2PO(OCH2CH3)2
64.
OCH2C6H5
H
CH2CH2PO(OH)2
65.
OCH2CH2C6H5
H
CH2CH2PO(OCH2CH3)2
66.
OCH2CH2C6H5
H
CH2CH2PO(OH)2
67.
OCH2CONH2
H
CH2CH2PO(OCH2CH3)2
68.
OCH2CONH2
H
CH2CH2PO(OH)2
69.
NH2
H
CH2CH2PO(OCH2CH3)2
70.
NH2
H
CH2CH2PO(OH)2
71.
NHSO2CH3
H
CH2CH2PO(OCH2CH3)2
72.
NHSO2CH3
H
CH2CH2PO(OH)2
73.
H
OCH2CH═CH2
CH2CH2PO(OCH2CH3)2
74.
H
OCH2CH═CH2
CH2CH2PO(OH)2
75.
H
OCH2C6H5
CH2CH2PO(OCH2CH3)2
76.
H
OCH2C6H5
CH2CH2PO(OH)2
77.
H
OCH2CH2C6H5
CH2CH2PO(OCH2CH3)2
78.
H
OCH2CH2C6H5
CH2CH2PO(OH)2
79.
H
OCH2CONH2
CH2CH2PO(OCH2CH3)2
80.
H
OCH2CONH2
CH2CH2PO(OH)2
81.
OCH2CH═CH2
H
CH2CH═CHCO2CH2CH3
82.
OCH2CH═CH2
H
CH2CH═CHCO2H
83.
OCH2C6H5
H
CH2CH═CHCO2CH2CH3
84.
OCH2C6H5
H
CH2CH═CHCO2H
85.
OCH2CH2C6H5
H
CH2CH═CHCO2CH2CH3
86.
OCH2CH2C6H5
H
CH2CH═CHCO2H
87.
OCH2CONH2
H
CH2CH═CHCO2CH2CH3
88.
OCH2CONH2
H
CH2CH═CHCO2H
89.
NH2
H
CH2CH═CHCO2CH2CH3
90.
NH2
H
CH2CH═CHCO2H
91.
NHSO2CH3
H
CH2CH═CHCO2CH2CH3
92.
NHSO2CH3
H
CH2CH═CHCO2H
93.
H
OCH2CH═CH2
CH2CH═CHCO2CH2CH3
94.
H
OCH2CH═CH2
CH2CH═CHCO2H
95.
H
OCH2C6H5
CH2CH═CHCO2CH2CH3
96.
H
OCH2C6H5
CH2CH═CHCO2H
97.
H
OCH2CH2C6H5
CH2CH═CHCO2CH2CH3
98.
H
OCH2CH2C6H5
CH2CH═CHCO2H
99.
H
OCH2CONH2
CH2CH═CHCO2CH2CH3
100.
H
OCH2CONH2
CH2CH═CHCO2H
TABLE IIb
EX. #
X
X1
R1
1.
OCH2CH═CH2
H
CO2CH2CH3
2.
OCH2CH═CH2
H
CO2H
3.
OCH2C6H5
H
CO2CH2CH3
4.
OCH2C6H5
H
CO2H
5.
OCH2CH2C6H5
H
CO2CH2CH3
6.
OCH2CH2C6H5
H
CO2H
7.
OCH2CONH2
H
CO2CH2CH3
8.
OCH2CONH2
H
CO2H
9.
NH2
H
CO2CH2CH3
10.
NH2
H
CO2H
11.
NHSO2CH3
H
CO2CH2CH3
12.
NHSO2CH3
H
CO2H
13.
H
OCH2CH═CH2
CO2CH2CH3
14.
H
OCH2CH═CH2
CO2H
15.
H
OCH2C6H5
CO2CH2CH3
16.
H
OCH2C6H5
CO2H
17.
H
OCH2CH2C6H5
CO2CH2CH3
18.
H
OCH2CH2C6H5
CO2H
19.
H
OCH2CONH2
CO2CH2CH3
20.
H
OCH2CONH2
CO2H
21.
OCH2CH═CH2
H
CH2CO2CH2CH3
22.
OCH2CH═CH2
H
CH2CO2H
23.
OCH2C6H5
H
CH2CO2CH2CH3
24.
OCH2C6H5
H
CH2CO2H
25.
OCH2CH2C6H5
H
CH2CO2CH2CH3
26.
OCH2CH2C6H5
H
CH2CO2H
27.
OCH2CONH2
H
CH2CO2CH2CH3
28.
OCH2CONH2
H
CH2CO2H
29.
NH2
H
CH2CO2CH2CH3
30.
NH2
H
CH2CO2H
31.
NHSO2CH3
H
CH2CO2CH2CH3
32.
NHSO2CH3
H
CH2CO2H
33.
H
OCH2CH═CH2
CH2CO2CH2CH3
34.
H
OCH2CH═CH2
CH2CO2H
35.
H
OCH2C6H5
CH2CO2CH2CH3
36.
H
OCH2C6H5
CH2CO2H
37.
H
OCH2CH2C6H5
CH2CO2CH2CH3
38.
H
OCH2CH2C6H5
CH2CO2H
39.
H
OCH2CONH2
CH2CO2CH2CH3
40.
H
OCH2CONH2
CH2CO2H
41.
OCH2CH═CH2
H
CH2CO2CH2CH2CH3
42.
OCH2CH═CH2
H
CH2CH2CO2H
43.
OCH2C6H5
H
CH2CH2CO2CH2CH3
44.
OCH2C6H5
H
CH2CH2CO2H
45.
OCH2CH2C6H5
H
CH2CO2CH2CH2CH3
46.
OCH2CH2C6H5
H
CH2CH2CO2H
47.
OCH2CONH2
H
CH2CH2CO2CH2CH3
48.
OCH2CONH2
H
CH2CH2CO2H
49.
NH2
H
CH2CO2CH2CH2CH3
50.
NH2
H
CH2CH2CO2H
51.
NHSO2CH3
H
CH2CH2CO2CH2CH3
52.
NHSO2CH3
H
CH2CH2CO2H
53.
H
OCH2CH═CH2
CH2CO2CH2CH2CH3
54.
H
OCH2CH═CH2
CH2CH2CO2H
55.
H
OCH2C6H5
CH2CH2CO2CH2CH3
56.
H
OCH2C6H5
CH2CH2CO2H
57.
H
OCH2CH2C6H5
CH2CO2CH2CH2CH3
58.
H
OCH2CH2C6H5
CH2CH2CO2H
59.
H
OCH2CONH2
CH2CH2CO2CH2CH3
60.
H
OCH2CONH2
CH2CH2CO2H
61.
OCH2CH═CH2
H
CH2CH2PO(OCH2CH3)2
62.
OCH2CH═CH2
H
CH2CH2PO(OH)2
63.
OCH2C6H5
H
CH2CH2PO(OCH2CH3)2
64.
OCH2C6H5
H
CH2CH2PO(OH)2
65.
OCH2CH2C6H5
H
CH2CH2PO(OCH2CH3)2
66.
OCH2CH2C6H5
H
CH2CH2PO(OH)2
67.
OCH2CONH2
H
CH2CH2PO(OCH2CH3)2
68.
OCH2CONH2
H
CH2CH2PO(OH)2
69.
NH2
H
CH2CH2PO(OCH2CH3)2
70.
NH2
H
CH2CH2PO(OH)2
71.
NHSO2CH3
H
CH2CH2PO(OCH2CH3)2
72.
NHSO2CH3
H
CH2CH2PO(OH)2
73.
H
OCH2CH═CH2
CH2CH2PO(OCH2CH3)2
74.
H
OCH2CH═CH2
CH2CH2PO(OH)2
75.
H
OCH2C6H5
CH2CH2PO(OCH2CH3)2
76.
H
OCH2C6H5
CH2CH2PO(OH)2
77.
H
OCH2CH2C6H5
CH2CH2PO(OCH2CH3)2
78.
H
OCH2CH2C6H5
CH2CH2PO(OH)2
79.
H
OCH2CONH2
CH2CH2PO(OCH2CH3)2
80.
H
OCH2CONH2
CH2CH2PO(OH)2
81.
OCH2CH═CH2
H
CH2CH═CHCO2CH2CH3
82.
OCH2CH═CH2
H
CH2CH═CHCO2H
83.
OCH2C6H5
H
CH2CH═CHCO2CH2CH3
84.
OCH2C6H5
H
CH2CH═CHCO2H
85.
OCH2CH2C6H5
H
CH2CH═CHCO2CH2CH3
86.
OCH2CH2C6H5
H
CH2CH═CHCO2H
87.
OCH2CONH2
H
CH2CH═CHCO2CH2CH3
88.
OCH2CONH2
H
CH2CH═CHCO2H
89.
NH2
H
CH2CH═CHCO2CH2CH3
90.
NH2
H
CH2CH═CHCO2H
91.
NHSO2CH3
H
CH2CH═CHCO2CH2CH3
92.
NHSO2CH3
H
CH2CH═CHCO2H
93.
H
OCH2CH═CH2
CH2CH═CHCO2CH2CH3
94.
H
OCH2CH═CH2
CH2CH═CHCO2H
95.
H
OCH2C6H5
CH2CH═CHCO2CH2CH3
96.
H
OCH2C6H5
CH2CH═CHCO2H
97.
H
OCH2CH2C6H5
CH2CH═CHCO2CH2CH3
98.
H
OCH2CH2C6H5
CH2CH═CHCO2H
99.
H
OCH2CONH2
CH2CH═CHCO2CH2CH3
100.
H
OCH2CONH2
CH2CH═CHCO2H
TABLE III
Ex. #
X
X1
R1
R″
1.
OCH2CH═CH2
H
H
CH2—CO2CH2CH3
2.
OCH2CH═CH2
H
CH3
CH2—CO2H
3.
OCH2C6H5
H
H
CH2—CO2CH2CH3
4.
OCH2C6H5
H
CH3
CH2—CO2H
5.
OCH2CH2C6H5
H
H
CH2—CO2CH2CH3
6.
OCH2CH2C6H5
H
CH3
CH2—CO2H
7.
OCH2—CONH2
H
H
CH2—CO2CH2CH3
8.
OCH2—CONH2
H
CH3
CH2—CO2H
9.
NH2
H
H
CH2—CO2CH2CH3
10.
NH2
H
CH3
CH2—CO2H
11.
NHSO2CH3
H
H
CH2—CO2CH2CH3
12.
NHSO2CH3
H
CH3
CH2—CO2H
13.
H
OCH2CH═CH2
H
CH2—CO2CH2CH3
14.
H
OCH2CH═CH2
CH3
CH2—CO2H
15.
H
OCH2C6H5
H
CH2—CO2CH2CH3
16.
H
OCH2C6H5
CH3
CH2—CO2H
17.
H
OCH2CH2C6H5
H
CH2—CO2CH2CH3
18.
H
OCH2CH2C6H5
CH3
CH2—CO2H
19.
H
OCH2—CONH2
H
CH2—CO2CH2CH3
20.
H
OCH2—CONH2
CH3
CH2—CO2H
21.
OCH2CH═CH2
H
H
CH2CH2—CO2CH2CH3
22.
OCH2CH═CH2
H
CH3
CH2CH2—CO2H
23.
OCH2C6H5
H
H
CH2CH2—CO2CH2CH3
24.
OCH2C6H5
H
CH3
CH2CH2—CO2H
25.
OCH2CH2C6H5
H
H
CH2CH2—CO2CH2CH3
26.
OCH2CH2C6H5
H
CH3
CH2CH2—CO2H
27.
OCH2—CONH2
H
H
CH2CH2—CO2CH2CH3
28.
OCH2—CONH2
H
CH3
CH2CH2—CO2H
35.
NH2
H
H
CH2CH2—CO2CH2CH3
36.
NH2
H
CH3
CH2CH2—CO2H
37.
NHSO2CH3
H
H
CH2CH2—CO2CH2CH3
38.
NHSO2CH3
H
CH3
CH2CH2—CO2H
39.
H
OCH2CH═CH2
H
CH2CH2—CO2CH2CH3
40.
H
OCH2CH═CH2
CH3
CH2CH2—CO2H
41.
H
OCH2C6H5
H
CH2CH2—CO2CH2CH3
42.
H
OCH2C6H5
CH3
CH2CH2—CO2H
43.
H
OCH2CH2C6H5
H
CH2CH2—CO2CH2CH3
44.
H
OCH2CH2C6H5
CH3
CH2CH2—CO2H
45.
H
OCH2—CONH2
H
CH2CH2—CO2CH2CH3
46.
H
OCH2—CONH2
CH3
CH2CH2—CO2H
47.
OCH2CH═CH2
H
H
CH2CH2P—O(OCH2CH3)2
48.
OCH2CH═CH2
H
CH3
CH2CH2P—O (OH)2
49.
OCH2C6H5
H
H
CH2CH2P—O(OCH2CH3)2
50.
OCH2C6H5
H
CH3
CH2CH2P—O(OH)2
51.
OCH2CH2C6H5
H
H
CH2CH2P—O(OCH2CH3)2
52.
OCH2CH2C6H5
H
CH3
CH2CH2P—O(OH)2
53.
OCH2—CONH2
H
H
CH2CH2P—O(OCH2CH3)2
54.
OCH2—CONH2
H
CH3
CH2CH2P—O(OH)2
55.
NH2
H
H
CH2CH2P—O(OCH2CH3)2
56.
NH2
H
CH3
CH2CH2P—O(OH)2
57.
NHSO2CH3
H
H
CH2CH2P—O(OCH2CH3)2
58.
NHSO2CH3
H
CH3
CH2CH2P—O(OH)2
59.
H
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
60.
H
OCH2CH═CH2
CH3
CH2CH2P—O(OH)2
61.
H
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
62.
H
OCH2C6H5
CH3
CH2CH2P—O(OH)2
63.
H
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
64.
H
OCH2CH2C6H5
CH3
CH2CH2P—O(OH)2
65.
H
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
66.
H
OCH2—CONH2
CH3
CH2CH2P—O(OH)2
67.
OCH2CH═CH2
H
H
CH2CH═CH—CO2CH2CH3
68.
OCH2CH═CH2
H
CH3
CH2CH═CH—CO2H
69.
OCH2C6H5
H
H
CH2CH═CH—CO2CH2CH3
70.
OCH2C6H5
H
CH3
CH2CH═CH—CO2H
71.
OCH2CH2C6H5
H
H
CH2CH═CH—CO2CH2CH3
72.
OCH2CH2C6H5
H
CH3
CH2CH═CH—CO2H
73.
OCH2—CONH2
H
H
CH2CH═CH—CO2CH2CH3
74.
OCH2—CONH2
H
CH3
CH2CH═CH—CO2H
75.
NH2
H
H
CH2CH═CH—CO2CH2CH3
76.
NH2
H
CH3
CH2CH═CH—CO2H
77.
NHSO2CH3
H
H
CH2CH═CH—CO2CH2CH3
78.
NHSO2CH3
H
CH3
CH2CH═CH—CO2H
79.
H
OCH2CH═CH2
H
CH2CH═CH—CO2CH2CH3
80.
H
OCH2CH═CH2
CH3
CH2CH═CH—CO2H
81.
H
OCH2C6H5
H
CH2CH═CH—CO2CH2CH3
82.
H
OCH2C6H5
CH3
CH2CH═CH—CO2H
83.
H
OCH2CH2C6H5
H
CH2CH═CH—CO2CH2CH3
84.
H
OCH2CH2C6H5
CH3
CH2CH═CH—CO2H
85.
H
OCH2—CONH2
H
CH2CH═CH—CO2CH2CH3
86.
H
OCH2—CONH2
CH3
CH2CH═CH—CO2H
87.
OCH2CH═CH2
H
CH2—CO2CH2CH3
CH3
88.
OCH2CH═CH2
H
CH2—CO2H
CH3
89.
OCH2C6H5
H
CH2—CO2CH2CH3
CH3
90.
OCH2C6H5
H
CH2—CO2H
CH3
91.
OCH2CH2C6H5
H
CH2—CO2CH2CH3
CH3
92.
OCH2CH2C6H5
H
CH2—CO2H
CH3
93.
OCH2—CONH2
H
CH2—CO2CH2CH3
CH3
94.
OCH2—CONH2
H
CH2—CO2H
CH3
95.
NH2
H
CH2—CO2CH2CH3
CH3
96.
NH2
H
CH2—CO2H
CH3
97.
NHSO2CH3
H
CH2—CO2CH2CH3
CH3
98.
NHSO2CH3
H
CH2—CO2H
CH3
99.
H
OCH2CH═CH2
CH2—CO2CH2CH3
CH3
100.
H
OCH2CH═CH2
CH2—CO2H
CH3
101.
H
OCH2C6H5
CH2—CO2CH2CH3
CH3
102.
H
OCH2C6H5
CH2—CO2H
CH3
103.
H
OCH2CH2C6H5
CH2—CO2CH2CH3
CH3
104.
H
OCH2CH2C6H5
CH2—CO2H
CH3
105.
H
OCH2—CONH2
CH2—CO2CH2CH3
CH3
106.
H
OCH2—CONH2
CH2—CO2H
CH3
107.
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
CH3
108.
OCH2CH═CH2
H
CH2CH2P—O(OH)2
CH3
109.
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH3
110.
OCH2C6H5
H
CH2CH2P—O(OH)2
CH3
111.
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH3
112.
OCH2CH2C6H5
H
CH2CH2P—O(OH)2
CH3
113.
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
CH3
114.
OCH2—CONH2
H
CH2CH2P—O(OH)2
CH3
115.
NH2
H
CH2CH2P—O(OCH2CH3)2
CH3
116.
NH2
H
CH2CH2P—O(OH)2
CH3
117.
NHSO2CH3
H
CH2CH2P—O(OCH2CH3)2
CH3
118.
NHSO2CH3
H
CH2CH2P—O(OH)2
CH3
119.
H
OCH2CH═CH2
CH2CH2P—O(OCH2CH3)2
CH3
120.
H
OCH2CH═CH2
CH2CH2P—O(OH)2
CH3
121.
H
OCH2C6H5
CH2CH2P—O(OCH2CH3)2
CH3
122.
H
OCH2C6H5
CH2CH2P—O(OH)2
CH3
123.
H
OCH2CH2C6H5
CH2CH2P—O(OCH2CH3)2
CH3
124.
H
OCH2CH2C6H5
CH2CH2P—O(OH)2
CH3
125.
H
OCH2—CONH2
CH2CH2P—O(OCH2CH3)2
CH3
126.
H
OCH2—CONH2
CH2CH2P—O(OH)2
CH3
127.
OCH2CH═CH2
H
CH2—CO2CH2CH3
CH2CH═CH2
128.
OCH2CH═CH2
H
CH2—CO2H
CH2CH═CH2
129.
OCH2C6H5
H
CH2—CO2CH2CH3
CH2CH═CH2
130.
OCH2C6H5
H
CH2—CO2H
CH2CH═CH2
131.
OCH2CH2C6H5
H
CH2—CO2CH2CH3
CH2CH═CH2
132.
OCH2CH2C6H5
H
CH2—CO2H
CH2CH═CH2
133.
OCH2—CONH2
H
CH2—CO2CH2CH3
CH2CH═CH2
134.
OCH2—CONH2
H
CH2—CO2H
CH2CH═CH2
135.
NH2
H
CH2—CO2CH2CH3
CH2CH═CH2
136.
NH2
H
CH2—CO2H
CH2CH═CH2
137.
NHSO2CH3
H
CH2—CO2CH2CH3
CH2CH═CH2
138.
NHSO2CH3
H
CH2—CO2H
CH2CH═CH2
139.
H
OCH2CH═CH2
CH2—CO2CH2CH3
CH2CH═CH2
140.
H
OCH2CH═CH2
CH2—CO2H
CH2CH═CH2
141.
H
OCH2C6H5
CH2—CO2CH2CH3
CH2CH═CH2
142.
H
OCH2C6H5
CH2—CO2H
CH2CH═CH2
143.
H
OCH2CH2C6H5
CH2—CO2CH2CH3
CH2CH═CH2
144.
H
OCH2CH2C6H5
CH2—CO2H
CH2CH═CH2
145.
H
OCH2—CONH2
CH2—CO2CH2CH3
CH2CH═CH2
146.
H
OCH2—CONH2
CH2—CO2H
CH2CH═CH2
147.
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
148.
OCH2CH═CH2
H
CH2CH2P—O(OH)2
CH2CH═CH2
149.
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
150.
OCH2C6H5
H
CH2CH2P—O(OH)2
CH2CH═CH2
151.
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
152.
OCH2CH2C6H5
H
CH2CH2P—O(OH)2
CH2CH═CH2
153.
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
154.
OCH2—CONH2
H
CH2CH2P—O(OH)2
CH2CH═CH2
155.
NH2
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
156.
NH2
H
CH2CH2P—O(OH)2
CH2CH═CH2
157.
NHSO2CH3
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
158.
NHSO2CH3
H
CH2CH2P—O(OH)2
CH2CH═CH2
159.
H
OCH2CH═CH2
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
160.
H
OCH2CH═CH2
CH2CH2P—O(OH)2
CH2CH═CH2
161.
H
OCH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
162.
H
OCH2C6H5
CH2CH2P—O(OH)2
CH2CH═CH2
163.
H
OCH2CH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
164.
H
OCH2CH2C6H5
CH2CH2P—O(OH)2
CH2CH═CH2
165.
H
OCH2—CONH2
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
166.
H
OCH2—CONH2
CH2CH2P—O(OH)2
CH2CH═CH2
167.
OCH2CH═CH2
H
CH2—CO2CH2CH3
CH2—CONH2
168.
OCH2CH═CH2
H
CH2—CO2H
CH2—CONH2
169.
OCH2C6H5
H
CH2—CO2CH2CH3
CH2—CONH2
170.
OCH2C6H5
H
CH2—CO2H
CH2—CONH2
171.
OCH2CH2C6H5
H
CH2—CO2CH2CH3
CH2—CONH2
172.
OCH2CH2C6H5
H
CH2—CO2H
CH2—CONH2
173.
OCH2—CONH2
H
CH2—CO2CH2CH3
CH2—CONH2
174.
OCH2—CONH2
H
CH2—CO2H
CH2—CONH2
175.
NH2
H
CH2—CO2CH2CH3
CH2—CONH2
176.
NH2
H
CH2—CO2H
CH2—CONH2
177.
NHSO2CH3
H
CH2—CO2CH2CH3
CH2—CONH2
178.
NHSO2CH3
H
CH2—CO2H
CH2—CONH2
179.
H
OCH2CH═CH2
CH2—CO2CH2CH3
CH2—CONH2
180.
H
OCH2CH═CH2
CH2—CO2H
CH2—CONH2
181.
H
OCH2C6H5
CH2—CO2CH2CH3
CH2—CONH2
182.
H
OCH2C6H5
CH2—CO2H
CH2—CONH2
183.
H
OCH2CH2C6H5
CH2—CO2CH2CH3
CH2—CONH2
184.
H
OCH2CH2C6H5
CH2—CO2H
CH2—CONH2
185.
H
OCH2—CONH2
CH2—CO2CH2CH3
CH2—CONH2
186.
H
OCH2—CONH2
CH2—CO2H
CH2—CONH2
187.
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
188.
OCH2CH═CH2
H
CH2CH2P—O(OH)2
CH2—CONH2
189.
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
190.
OCH2C6H5
H
CH2CH2P—O(OH)2
CH2—CONH2
191.
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
192.
OCH2CH2C6H5
H
CH2CH2P—O(OH)2
CH2—CONH2
193.
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
194.
OCH2—CONH2
H
CH2CH2P—O(OH)2
CH2—CONH2
195.
NH2
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
196.
NH2
H
CH2CH2P—O(OH)2
CH2—CONH2
197.
NHSO2CH3
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
198.
NHSO2CH3
H
CH2CH2P—O(OH)2
CH2—CONH2
199.
H
OCH2CH═CH2
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
200.
H
OCH2CH═CH2
CH2CH2P—O(OH)2
CH2—CONH2
201.
H
OCH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
202.
H
OCH2C6H5
CH2CH2P—O(OH)2
CH2—CONH2
203.
H
OCH2CH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
204.
H
OCH2CH2C6H5
CH2CH2P—O(OH)2
CH2—CONH2
205.
H
OCH2—CONH2
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
206.
H
OCH2—CONH2
CH2CH2P—O(OH)2
CH2—CONH2
207.
OCH2CH═CH2
H
CH2—CO2CH2CH3
CH2C6H5
208.
OCH2CH═CH2
H
CH2—CO2H
CH2C6H5
209.
OCH2C6H5
H
CH2—CO2CH2CH3
CH2C6H5
210.
OCH2C6H5
H
CH2—CO2H
CH2C6H5
211.
OCH2CH2C6H5
H
CH2—CO2CH2CH3
CH2C6H5
212.
OCH2CH2C6H5
H
CH2—CO2H
CH2C6H5
213.
OCH2—CONH2
H
CH2—CO2CH2CH3
CH2C6H5
214.
OCH2—CONH2
H
CH2—CO2H
CH2C6H5
215.
NH2
H
CH2—CO2CH2CH3
CH2C6H5
216.
NH2
H
CH2—CO2H
CH2C6H5
217.
NHSO2CH3
H
CH2—CO2CH2CH3
CH2C6H5
218.
NHSO2CH3
H
CH2—CO2H
CH2C6H5
219.
H
OCH2CH═CH2
CH2—CO2CH2CH3
CH2C6H5
220.
H
OCH2CH═CH2
CH2—CO2H
CH2C6H5
221.
H
OCH2C6H5
CH2—CO2CH2CH3
CH2C6H5
222.
H
OCH2C6H5
CH2—CO2H
CH2C6H5
223.
H
OCH2CH2C6H5
CH2—CO2CH2CH3
CH2C6H5
224.
H
OCH2CH2C6H5
CH2—CO2H
CH2C6H5
225.
H
OCH2—CONH2
CH2—CO2CH2CH3
CH2C6H5
226.
H
OCH2—CONH2
CH2—CO2H
CH2C6H5
227.
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
228.
OCH2CH═CH2
H
CH2CH2P—O(OH)2
CH2C6H5
229.
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
230.
OCH2C6H5
H
CH2CH2P—O(OH)2
CH2C6H5
231.
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
232.
OCH2CH2C6H5
H
CH2CH2P—O(OH)2
CH2C6H5
233.
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
234.
OCH2—CONH2
H
CH2CH2P—O(OH)2
CH2C6H5
235.
NH2
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
236.
NH2
H
CH2CH2P—O(OH)2
CH2C6H5
237.
NHSO2CH3
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
238.
NHSO2CH3
H
CH2CH2P—O(OH)2
CH2C6H5
239.
H
OCH2CH═CH2
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
240.
H
OCH2CH═CH2
CH2CH2P—O(OH)2
CH2—CONH2
241.
H
OCH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
242.
H
OCH2C6H5
CH2CH2P—O(OH)2
CH2—CONH2
243.
H
OCH2CH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
244.
H
OCH2CH2C6H5
CH2CH2P—O(OH)2
CH2—CONH2
245.
H
OCH2—CONH2
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
246.
H
OCH2—CONH2
CH2CH2P—O(OH)2
CH2—CONH2
TABLE IV
Ex. #
X
X1
R1
R″
1.
OCH2CH═CH2
H
H
CH2—CO2CH2CH3
2.
OCH2CH═CH2
H
CH3
CH2—CO2H
3.
OCH2C6H5
H
H
CH2—CO2CH2CH3
4.
OCH2C6H5
H
CH3
CH2—CO2H
5.
OCH2CH2C6H5
H
H
CH2—CO2CH2CH3
6.
OCH2CH2C6H5
H
CH3
CH2—CO2H
7.
OCH2—CONH2
H
H
CH2—CO2CH2CH3
8.
OCH2—CONH2
H
CH3
CH2—CO2H
9.
NH2
H
H
CH2—CO2CH2CH3
10.
NH2
H
CH3
CH2—CO2H
11.
NHSO2CH3
H
H
CH2—CO2CH2CH3
12.
NHSO2CH3
H
CH3
CH2—CO2H
13.
H
OCH2CH═CH2
H
CH2—CO2CH2CH3
14.
H
OCH2CH═CH2
CH3
CH2—CO2H
15.
H
OCH2C6H5
H
CH2—CO2CH2CH3
16.
H
OCH2C6H5
CH3
CH2—CO2H
17.
H
OCH2CH2C6H5
H
CH2—CO2CH2CH3
18.
H
OCH2CH2C6H5
CH3
CH2—CO2H
19.
H
OCH2—CONH2
H
CH2—CO2CH2CH3
20.
H
OCH2—CONH2
CH3
CH2—CO2H
21.
OCH2CH═CH2
H
H
CH2CH2—CO2CH2CH3
22.
OCH2CH═CH2
H
CH3
CH2CH2—CO2H
23.
OCH2C6H5
H
H
CH2CH2—CO2CH2CH3
24.
OCH2C6H5
H
CH3
CH2CH2—CO2H
25.
OCH2CH2C6H5
H
H
CH2CH2—CO2CH2CH3
26.
OCH2CH2C6H5
H
CH3
CH2CH2—CO2H
27.
OCH2—CONH2
H
H
CH2CH2—CO2CH2CH3
28.
OCH2—CONH2
H
CH3
CH2CH2—CO2H
29.
NH2
H
H
CH2CH2—CO2CH2CH3
30.
NH2
H
CH3
CH2CH2—CO2H
31.
NHSO2CH3
H
H
CH2CH2—CO2CH2CH3
32.
NHSO2CH3
H
CH3
CH2CH2—CO2H
33.
H
OCH2CH═CH2
H
CH2CH2—CO2CH2CH3
34.
H
OCH2CH═CH2
CH3
CH2CH2—CO2H
35.
H
OCH2C6H5
H
CH2CH2—CO2CH2CH3
36.
H
OCH2C6H5
CH3
CH2CH2—CO2H
37.
H
OCH2CH2C6H5
H
CH2CH2—CO2CH2CH3
38.
H
OCH2CH2C6H5
CH3
CH2CH2—CO2H
39.
H
OCH2—CONH2
H
CH2CH2—CO2CH2CH3
40.
H
OCH2—CONH2
CH3
CH2CH2—CO2H
41.
OCH2CH═CH2
H
H
CH2CH2P—O(OCH2CH3)2
42.
OCH2CH═CH2
H
CH3
CH2CH2P—O(OH)2
43.
OCH2C6H5
H
H
CH2CH2P—O(OCH2CH3)2
44.
OCH2C6H5
H
CH3
CH2CH2P—O(OH)2
45.
OCH2CH2C6H5
H
H
CH2CH2P—O(OCH2CH3)2
46.
OCH2CH2C6H5
H
CH3
CH2CH2P—O(OH)2
47.
OCH2—CONH2
H
H
CH2CH2P—O(OCH2CH3)2
48.
OCH2—CONH2
H
CH3
CH2CH2P—O(OH)2
49.
NH2
H
H
CH2CH2P—O(OCH2CH3)2
50.
NH2
H
CH3
CH2CH2P—O(OH)2
51.
NHSO2CH3
H
H
CH2CH2P—O(OCH2CH3)2
52.
NHSO2CH3
H
CH3
CH2CH2P—O(OH)2
53.
H
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
54.
H
OCH2CH═CH2
CH3
CH2CH2P—O(OH)2
55.
H
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
56.
H
OCH2C6H5
CH3
CH2CH2P—O(OH)2
57.
H
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
58.
H
OCH2CH2C6H5
CH3
CH2CH2P—O(OH)2
59.
H
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
60.
H
OCH2—CONH2
CH3
CH2CH2P—O(OH)2
61.
OCH2CH═CH2
H
H
CH2CH═CH—CO2CH2CH3
62.
OCH2CH═CH2
H
CH3
CH2CH═CH—CO2H
63.
OCH2C6H5
H
H
CH2CH═CH—CO2CH2CH3
64.
OCH2C6H5
H
CH3
CH2CH═CH—CO2H
65.
OCH2CH2C6H5
H
H
CH2CH═CH—CO2CH2CH3
66.
OCH2CH2C6H5
H
CH3
CH2CH═CH—CO2H
67.
OCH2—CONH2
H
H
CH2CH═CH—CO2CH2CH3
68.
OCH2—CONH2
H
CH3
CH2CH═CH—CO2H
69.
NH2
H
H
CH2CH═CH—CO2CH2CH3
70.
NH2
H
CH3
CH2CH═CH—CO2H
71.
NHSO2CH3
H
H
CH2CH═CH—CO2CH2CH3
72.
NHSO2CH3
H
CH3
CH2CH═CH—CO2H
73.
H
OCH2CH═CH2
H
CH2CH═CH—CO2CH2CH3
74.
H
OCH2CH═CH2
CH3
CH2CH═CH—CO2H
75.
H
OCH2C6H5
H
CH2CH═CH—CO2CH2CH3
76.
H
OCH2C6H5
CH3
CH2CH═CH—CO2H
77.
H
OCH2CH2C6H5
H
CH2CH═CH—CO2CH2CH3
78.
H
OCH2CH2C6H5
CH3
CH2CH═CH—CO2H
79.
H
OCH2—CONH2
H
CH2CH═CH—CO2CH2CH3
80.
H
OCH2—CONH2
CH3
CH2CH═CH—CO2H
81.
OCH2CH═CH2
H
CH2—CO2CH2CH3
CH3
82.
OCH2CH═CH2
H
CH2—CO2H
CH3
83.
OCH2C6H5
H
CH2—CO2CH2CH3
CH3
84.
OCH2C6H5
H
CH2—CO2H
CH3
85.
OCH2CH2C6H5
H
CH2—CO2CH2CH3
CH3
86.
OCH2CH2C6H5
H
CH2—CO2H
CH3
87.
OCH2—CONH2
H
CH2—CO2CH2CH3
CH3
88.
OCH2—CONH2
H
CH2—CO2H
CH3
89.
NH2
H
CH2—CO2CH2CH3
CH3
90.
NH2
H
CH2—CO2H
CH3
91.
NHSO2CH3
H
CH2—CO2CH2CH3
CH3
92.
NHSO2CH3
H
CH2—CO2H
CH3
93.
H
OCH2CH═CH2
CH2—CO2CH2CH3
CH3
94.
H
OCH2CH═CH2
CH2—CO2H
CH3
95.
H
OCH2C6H5
CH2—CO2CH2CH3
CH3
96.
H
OCH2C6H5
CH2—CO2H
CH3
97.
H
OCH2CH2C6H5
CH2—CO2CH2CH3
CH3
98.
H
OCH2CH2C6H5
CH2—CO2H
CH3
99.
H
OCH2—CONH2
CH2—CO2CH2CH3
CH3
100.
H
OCH2—CONH2
CH2—CO2H
CH3
101.
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
CH3
102.
OCH2CH═CH2
H
CH2CH2P—O(OH)2
CH3
103.
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH3
104.
OCH2C6H5
H
CH2CH2P—O(OH)2
CH3
105.
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH3
106.
OCH2CH2C6H5
H
CH2CH2P—O(OH)2
CH3
107.
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
CH3
108.
OCH2—CONH2
H
CH2CH2P—O(OH)2
CH3
109.
NH2
H
CH2CH2P—O(OCH2CH3)2
CH3
110.
NH2
H
CH2CH2P—O(OH)2
CH3
111.
NHSO2CH3
H
CH2CH2P—O(OCH2CH3)2
CH3
112.
NHSO2CH3
H
CH2CH2P—O(OH)2
CH3
113.
H
OCH2CH═CH2
CH2CH2P—O(OCH2CH3)2
CH3
114.
H
OCH2CH═CH2
CH2CH2P—O(OH)2
CH3
115.
H
OCH2C6H5
CH2CH2P—O(OCH2CH3)2
CH3
116.
H
OCH2C6H5
CH2CH2P—O(OH)2
CH3
117.
H
OCH2CH2C6H5
CH2CH2P—O(OCH2CH3)2
CH3
118.
H
OCH2CH2C6H5
CH2CH2P—O(OH)2
CH3
119.
H
OCH2—CONH2
CH2CH2P—O(OCH2CH3)2
CH3
120.
H
OCH2—CONH2
CH2CH2P—O(OH)2
CH3
121.
OCH2CH═CH2
H
CH2—CO2CH2CH3
CH2CH═CH2
122.
OCH2CH═CH2
H
CH2—CO2H
CH2CH═CH2
123.
OCH2C6H5
H
CH2—CO2CH2CH3
CH2CH═CH2
124.
OCH2C6H5
H
CH2—CO2H
CH2CH═CH2
125.
OCH2CH2C6H5
H
CH2—CO2CH2CH3
CH2CH═CH2
126.
OCH2CH2C6H5
H
CH2—CO2H
CH2CH═CH2
127.
OCH2—CONH2
H
CH2—CO2CH2CH3
CH2CH═CH2
128.
OCH2—CONH2
H
CH2—CO2H
CH2CH═CH2
129.
NH2
H
CH2—CO2CH2CH3
CH2CH═CH2
130.
NH2
H
CH2—CO2H
CH2CH═CH2
131.
NHSO2CH3
H
CH2—CO2CH2CH3
CH2CH═CH2
132.
NHSO2CH3
H
CH2—CO2H
CH2CH═CH2
133.
H
OCH2CH═CH2
CH2—CO2CH2CH3
CH2CH═CH2
134.
H
OCH2CH═CH2
CH2—CO2H
CH2CH═CH2
135.
H
OCH2C6H5
CH2—CO2CH2CH3
CH2CH═CH2
136.
H
OCH2C6H5
CH2—CO2H
CH2CH═CH2
137.
H
OCH2CH2C6H5
CH2—CO2CH2CH3
CH2CH═CH2
138.
H
OCH2CH2C6H5
CH2—CO2H
CH2CH═CH2
139.
H
OCH2—CONH2
CH2—CO2CH2CH3
CH2CH═CH2
140.
H
OCH2—CONH2
CH2—CO2H
CH2CH═CH2
141.
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
142.
OCH2CH═CH2
H
CH2CH2P—O(OH)2
CH2CH═CH2
143.
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
144.
OCH2C6H5
H
CH2CH2P—O(OH)2
CH2CH═CH2
145.
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
146.
OCH2CH2C6H5
H
CH2CH2P—O(OH)2
CH2CH═CH2
147.
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
148.
OCH2—CONH2
H
CH2CH2P—O(OH)2
CH2CH═CH2
149.
NH2
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
150.
NH2
H
CH2CH2P—O(OH)2
CH2CH═CH2
151.
NHSO2CH3
H
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
152.
NHSO2CH3
H
CH2CH2P—O(OH)2
CH2CH═CH2
153.
H
OCH2CH═CH2
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
154.
H
OCH2CH═CH2
CH2CH2P—O(OH)2
CH2CH═CH2
155.
H
OCH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
156.
H
OCH2C6H5
CH2CH2P—O(OH)2
CH2CH═CH2
157.
H
OCH2CH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
158.
H
OCH2CH2C6H5
CH2CH2P—O(OH)2
CH2CH═CH2
159.
H
OCH2—CONH2
CH2CH2P—O(OCH2CH3)2
CH2CH═CH2
160.
H
OCH2—CONH2
CH2CH2P—O(OH)2
CH2CH═CH2
161.
OCH2CH═CH2
H
CH2—CO2CH2CH3
CH2—CONH2
162.
OCH2CH═CH2
H
CH2—CO2H
CH2—CONH2
163.
OCH2C6H5
H
CH2—CO2CH2CH3
CH2—CONH2
164.
OCH2C6H5
H
CH2—CO2H
CH2—CONH2
165.
OCH2CH2C6H5
H
CH2—CO2CH2CH3
CH2—CONH2
166.
OCH2CH2C6H5
H
CH2—CO2H
CH2—CONH2
167.
OCH2—CONH2
H
CH2—CO2CH2CH3
CH2—CONH2
168.
OCH2—CONH2
H
CH2—CO2H
CH2—CONH2
169.
NH2
H
CH2—CO2CH2CH3
CH2—CONH2
170.
NH2
H
CH2—CO2H
CH2—CONH2
171.
NHSO2CH3
H
CH2—CO2CH2CH3
CH2—CONH2
172.
NHSO2CH3
H
CH2—CO2H
CH2—CONH2
173.
H
OCH2CH═CH2
CH2—CO2CH2CH3
CH2—CONH2
174.
H
OCH2CH═CH2
CH2—CO2H
CH2—CONH2
175.
H
OCH2C6H5
CH2—CO2CH2CH3
CH2—CONH2
176.
H
OCH2C6H5
CH2—CO2H
CH2—CONH2
177.
H
OCH2CH2C6H5
CH2—CO2CH2CH3
CH2—CONH2
178.
H
OCH2CH2C6H5
CH2—CO2H
CH2—CONH2
179.
H
OCH2—CONH2
CH2—CO2CH2CH3
CH2—CONH2
180.
H
OCH2—CONH2
CH2—CO2H
CH2—CONH2
181.
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
182.
OCH2CH═CH2
H
CH2CH2P—O(OH)2
CH2—CONH2
183.
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
184.
OCH2C6H5
H
CH2CH2P—O(OH)2
CH2—CONH2
185.
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
186.
OCH2CH2C6H5
H
CH2CH2P—O(OH)2
CH2—CONH2
187.
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
188.
OCH2—CONH2
H
CH2CH2P—O(OH)2
CH2—CONH2
189.
NH2
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
190.
NH2
H
CH2CH2P—O(OH)2
CH2—CONH2
191.
NHSO2CH3
H
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
192.
NHSO2CH3
H
CH2CH2P—O(OH)2
CH2—CONH2
193.
H
OCH2CH═CH2
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
194.
H
OCH2CH═CH2
CH2CH2P—O(OH)2
CH2—CONH2
195.
H
OCH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
196.
H
OCH2C6H5
CH2CH2P—O(OH)2
CH2—CONH2
197.
H
OCH2CH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
198.
H
OCH2CH2C6H5
CH2CH2P—O(OH)2
CH2—CONH2
199.
H
OCH2—CONH2
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
200.
H
OCH2—CONH2
CH2CH2P—O(OH)2
CH2—CONH2
201.
OCH2CH═CH2
H
CH2—CO2CH2CH3
CH2C6H5
202.
OCH2CH═CH2
H
CH2—CO2H
CH2C6H5
203.
OCH2C6H5
H
CH2—CO2CH2CH3
CH2C6H5
204.
OCH2C6H5
H
CH2—CO2H
CH2C6H5
205.
OCH2CH2C6H5
H
CH2—CO2CH2CH3
CH2C6H5
206.
OCH2CH2C6H5
H
CH2—CO2H
CH2C6H5
207.
OCH2—CONH2
H
CH2—CO2CH2CH3
CH2C6H5
208.
OCH2—CONH2
H
CH2—CO2H
CH2C6H5
209.
NHSO2CH3
H
CH2—CO2CH2CH3
CH2C6H5
210.
NHSO2CH3
H
CH2—CO2H
CH2C6H5
211.
H
OCH2CH═CH2
CH2—CO2CH2CH3
CH2C6H5
212.
H
OCH2CH═CH2
CH2—CO2H
CH2C6H5
213.
H
OCH2C6H5
CH2—CO2CH2CH3
CH2C6H5
214.
H
OCH2C6H5
CH2—CO2H
CH2C6H5
215.
H
OCH2CH2C6H5
CH2—CO2CH2CH3
CH2C6H5
216.
H
OCH2CH2C6H5
CH2—CO2H
CH2C6H5
217.
H
OCH2—CONH2
CH2—CO2CH2CH3
CH2C6H5
218.
H
OCH2—CONH2
CH2—CO2H
CH2C6H5
219.
OCH2CH═CH2
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
220.
OCH2CH═CH2
H
CH2CH2P—O(OH)2
CH2C6H5
221.
OCH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
222.
OCH2C6H5
H
CH2CH2P—O(OH)2
CH2C6H5
223.
OCH2CH2C6H5
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
224.
OCH2CH2C6H5
H
CH2CH2P—O(OH)2
CH2C6H5
225.
OCH2—CONH2
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
226.
OCH2—CONH2
H
CH2CH2P—O(OH)2
CH2C6H5
227.
NH2
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
228.
NH2
H
CH2CH2P—O(OH)2
CH2C6H5
229.
NHSO2CH3
H
CH2CH2P—O(OCH2CH3)2
CH2C6H5
230.
NHSO2CH3
H
CH2CH2P—O(OH)2
CH2C6H5
231.
H
OCH2CH═CH2
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
232.
H
OCH2CH═CH2
CH2CH2P—O(OH)2
CH2—CONH2
233.
H
OCH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
234.
H
OCH2C6H5
CH2CH2P—O(OH)2
CH2—CONH2
235.
H
OCH2CH2C6H5
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
236.
H
OCH2CH2C6H5
CH2CH2P—O(OH)2
CH2—CONH2
237.
H
OCH2—CONH2
CH2CH2P—O(OCH2CH3)2
CH2—CONH2
238.
H
OCH2—CONH2
CH2CH2P—O(OH)2
CH2—CONH2
TABLE Va
Ex.
#
X
X1
X2
X3
R1
1.
OCH2CO2—CH2CH3
H
H
H
H
2.
OCH2CO2—CH2CH3
H
H
H
CH3
3.
OCH2CO2H
H
H
H
H
4.
OCH2CO2H
H
H
H
CH3
5.
OCH2CH2—CO2CH2CH3
H
H
H
H
6.
OCH2CH2—CO2CH2CH3
H
H
H
CH3
7.
OCH2CH2—CO2H
H
H
H
H
8.
OCH2CH2—CO2H
H
H
H
CH3
9.
OCH2CH═CH—CO2CH2CH3
H
H
H
H
10.
OCH2CH═CH—CO2CH2CH3
H
H
H
CH3
11.
OCH2CH═CH—CO2H
H
H
H
H
12.
OCH2CH═CH—CO2H
H
H
H
CH3
13.
OCH2CH2—PO(OCH2CH3)2
H
H
H
H
14.
OCH2CH2—PO(OCH2CH3)2
H
H
H
CH3
15.
OCH2CH2—PO(OH)2
H
H
H
H
16.
OCH2CH2—PO(OH)2
H
H
H
CH3
17.
H
OCH2CO2—CH2CH3
H
H
H
18.
H
OCH2CO2—CH2CH3
H
H
CH3
19.
H
OCH2CO2H
H
H
H
20.
H
OCH2CO2H
H
H
CH3
21.
H
OCH2CH2CO2—CH2CH3
H
H
H
22.
H
OCH2CH2CO2—CH2CH3
H
H
CH3
23.
H
OCH2CH2CO2H
H
H
H
24.
H
OCH2CH2CO2H
H
H
CH3
25.
H
OCH2CH═CH—CO2CH2CH3
H
H
H
26.
H
OCH2CH═CH—CO2CH2CH3
H
H
CH3
27.
H
OCH2CH═CH—CO2H
H
H
H
28.
H
OCH2CH═CH—CO2H
H
H
CH3
29.
H
OCH2CH2—PO(OCH2CH3)2
H
H
H
30.
H
OCH2CH2—PO(OCH2CH3)2
H
H
CH3
31.
H
OCH2CH2—PO(OH)2
H
H
H
32.
H
OCH2CH2—PO(OH)2
H
H
CH3
33.
H
H
OCH2CO2—CH2CH3
H
H
34.
H
H
OCH2CO2—CH2CH3
H
CH3
35.
H
H
OCH2CO2H
H
H
36.
H
H
OCH2CO2H
H
CH3
37.
H
H
OCH2CH2—CO2CH2CH3
H
H
38.
H
H
OCH2CH2—CO2CH2CH3
H
CH3
39.
H
H
OCH2CH2—CO2H
H
H
40.
H
H
OCH2CH2—CO2H
H
CH3
41.
H
H
OCH2—CH═CH—CO2CH2CH3
H
H
42.
H
H
OCH2—CH═CH—CO2CH2CH3
H
CH3
43.
H
H
OCH2—CH═CHCO2H
H
H
44.
H
H
OCH2—CH═CHCO2H
H
CH3
45.
H
H
OCH2CH2PO—(OCH2CH3)2
H
H
46.
H
H
OCH2CH2PO—(OCH2CH3)2
H
CH3
47.
H
H
OCH2CH2—PO(OH)2
H
H
48.
H
H
OCH2CH2—PO(OH)2
H
CH3
49.
H
H
H
OCH2CO2—CH2CH3
H
50.
H
H
H
OCH2CO2—CH2CH3
CH3
51.
H
H
H
OCH2CO2H
H
52.
H
H
H
OCH2CO2H
CH3
53.
H
H
H
OCH2CH2—CO2CH2CH3
H
54.
H
H
H
OCH2CH2—CO2CH2CH3
CH3
55.
H
H
H
OCH2CH2—CO2H
H
56.
H
H
H
OCH2CH2—CO2H
CH3
57.
H
H
H
OCH2—CH═CH—CO2CH2CH3
H
58.
H
H
H
OCH2—CH═CH—CO2CH2CH3
CH3
59.
H
H
H
OCH2—CH═CHCO2H
H
60.
H
H
H
OCH2—CH═CHCO2H
CH3
61.
H
H
H
OCH2CH2PO—(OCH2CH3)2
H
62.
H
H
H
OCH2CH2PO—(OCH2CH3)2
CH3
63.
H
H
H
OCH2CH2—PO(OH)2
H
64.
H
H
H
OCH2CH2—PO(OH)2
CH3
TABLE Vb
Ex.
#
X
X1
X2
X3
R1
1.
OCH2CO2—CH2CH3
H
H
H
H
2.
OCH2CO2—CH2CH3
H
H
H
CH3
3.
OCH2CO2H
H
H
H
H
4.
OCH2CO2H
H
H
H
CH3
5.
OCH2CH2—CO2CH2CH3
H
H
H
H
6.
OCH2CH2—CO2CH2CH3
H
H
H
CH3
7.
OCH2CH2—CO2H
H
H
H
H
8.
OCH2CH2—CO2H
H
H
H
CH3
9.
OCH2CH═CH—CO2CH2CH3
H
H
H
H
10.
OCH2CH═CH—CO2CH2CH3
H
H
H
CH3
11.
OCH2CH═CH—CO2H
H
H
H
H
12.
OCH2CH═CH—CO2H
H
H
H
CH3
13.
OCH2CH2—PO(OCH2CH3)2
H
H
H
H
14.
OCH2CH2—PO(OCH2CH3)2
H
H
H
CH3
15.
OCH2CH2—PO(OH)2
H
H
H
H
16.
OCH2CH2—PO(OH)2
H
H
H
CH3
17.
H
OCH2CO2—CH2CH3
H
H
H
18.
H
OCH2CO2—CH2CH3
H
H
CH3
19.
H
OCH2CO2H
H
H
H
20.
H
OCH2CO2H
H
H
CH3
21.
H
OCH2CH2CO2—CH2CH3
H
H
H
22.
H
OCH2CH2CO2—CH2CH3
H
H
CH3
23.
H
OCH2CH2CO2H
H
H
H
24.
H
OCH2CH2CO2H
H
H
CH3
25.
H
OCH2CH═CH—CO2CH2CH3
H
H
H
26.
H
OCH2CH═CH—CO2CH2CH3
H
H
CH3
27.
H
OCH2CH═CH—CO2H
H
H
H
28.
H
OCH2CH═CH—CO2H
H
H
CH3
29.
H
OCH2CH2—PO(OCH2CH3)2
H
H
H
30.
H
OCH2CH2—PO(OCH2CH3)2
H
H
CH3
31.
H
OCH2CH2—PO(OH)2
H
H
H
32.
H
OCH2CH2—PO(OH)2
H
H
CH3
33.
H
H
OCH2CO2—CH2CH3
H
H
34.
H
H
OCH2CO2—CH2CH3
H
CH3
35.
H
H
OCH2CO2H
H
H
36.
H
H
OCH2CO2H
H
CH3
37.
H
H
OCH2CH2—CO2CH2CH3
H
H
38.
H
H
OCH2CH2—CO2CH2CH3
H
CH3
39.
H
H
OCH2CH2—CO2H
H
H
40.
H
H
OCH2CH2—CO2H
H
CH3
41.
H
H
OCH2—CH═CH—CO2CH2CH3
H
H
42.
H
H
OCH2—CH═CH—CO2CH2CH3
H
CH3
43.
H
H
OCH2—CH═CHCO2H
H
H
44.
H
H
OCH2—CH═CHCO2H
H
CH3
45.
H
H
OCH2CH2PO—(OCH2CH3)2
H
H
46.
H
H
OCH2CH2PO—(OCH2CH3)2
H
CH3
47.
H
H
OCH2CH2—PO(OH)2
H
H
48.
H
H
OCH2CH2—PO(OH)2
H
CH3
49.
H
H
H
OCH2CO2—CH2CH3
H
50.
H
H
H
OCH2CO2—CH2CH3
CH3
51.
H
H
H
OCH2CO2H
H
52.
H
H
H
OCH2CO2H
CH3
53.
H
H
H
OCH2CH2—CO2CH2CH3
H
54.
H
H
H
OCH2CH2—CO2CH2CH3
CH3
55.
H
H
H
OCH2CH2—CO2H
H
56.
H
H
H
OCH2CH2—CO2H
CH3
57.
H
H
H
OCH2—CH═CH—CO2CH2CH3
H
58.
H
H
H
OCH2—CH═CH—CO2CH2CH3
CH3
59.
H
H
H
OCH2—CH═CHCO2H
H
60.
H
H
H
OCH2—CH═CHCO2H
CH3
61.
H
H
H
OCH2CH2PO—(OCH2CH3)2
H
62.
H
H
H
OCH2CH2PO—(OCH2CH3)2
CH3
63.
H
H
H
OCH2CH2—PO(OH)2
H
64.
H
H
H
OCH2CH2—PO(OH)2
CH3
TABLE VIIa
Ex. #
X
X1
X2
R
1.
OCH2CH═CH2
H
H
H
2.
OCH2CH═CH2
H
H
CH3
3.
NHSO2CH3
H
H
H
4.
NHSO2CH3
H
H
CH3
5.
OCH2C6H5
H
H
H
6.
OCH2C6H5
H
H
CH3
7.
OCH2C6H4—Cl(3)
H
H
H
8.
OCH2C6H4—Cl(3)
H
H
CH3
9.
OCH2C6H4—Cl(4)
H
H
H
10.
OCH2C6H4—Cl(4)
H
H
CH3
11.
OCH2C6H4—F(3)
H
H
H
12.
OCH2C6H4—F(3)
H
H
CH3
13.
OCH2C6H4—F(4)
H
H
H
14.
OCH2C6H4—F(4)
H
H
CH3
15.
OCH2C6H4—CF3(3)
H
H
H
16.
OCH2C6H4—CF3(3)
H
H
CH3
17.
OCH2C6H4—CF3(4)
H
H
H
18.
OCH2C6H4—CF3(4)
H
H
CH3
19.
OCH2C6H4—NO2(3)
H
H
H
20.
OCH2C6H4—NO2(3)
H
H
CH3
21.
OCH2C6H4—NO2(4)
H
H
H
22.
OCH2C6H4—NO2(4)
H
H
CH3
23.
OCH2C6H4—NHSO2CH3(3)
H
H
H
24.
OCH2C6H4—NHSO2CH3(3)
H
H
CH3
25.
OCH2C6H4—NHSO2CH3(4)
H
H
H
26.
OCH2C6H4—NHSO2CH3(4)
H
H
CH3
27.
OCH2C6H4—CN(3)
H
H
H
28.
OCH2C6H4—CN(3)
H
H
CH3
29.
OCH2C6H4—CN(4)
H
H
H
30.
OCH2C6H4—CN(4)
H
H
CH3
31.
OCH2C6H4—CONH2(3)
H
H
H
32.
OCH2C6H4—CONH2(3)
H
H
CH3
33.
OCH2C6H4—CONH2(4)
H
H
H
34.
OCH2C6H4—CONH2(4)
H
H
CH3
35.
OCH2C6H4—CH2CN(3)
H
H
H
36.
OCH2C6H4—CH2CN(3)
H
H
CH3
37.
OCH2C6H4—CH2CN(4)
H
H
H
38.
OCH2C6H4—CH2CN(4)
H
H
CH3
39.
OCH2C6H4—CH2CONH2(3)
H
H
H
40.
OCH2C6H4—CH2CONH2(3)
H
H
CH3
41.
OCH2C6H4—CH2CONH2(4)
H
H
H
42.
OCH2C6H4—CH2CONH2(4)
H
H
CH3
43.
OCH2C6H4—OCH2CN(3)
H
H
H
44.
OCH2C6H4—OCH2CN(3)
H
H
CH3
45.
OCH2C6H4—OCH2CN(4)
H
H
H
46.
OCH2C6H4—OCH2CN(4)
H
H
CH3
47.
OCH2C6H4—OCH2CONH2(3)
H
H
H
48.
OCH2C6H4—OCH2CONH2(3)
H
H
CH3
49.
OCH2C6H4—OCH2CONH2(4)
H
H
H
50.
OCH2C6H4—OCH2CONH2(4)
H
H
CH3
51.
OCH2C6H3—(CN)2(3,5)
H
H
H
52.
OCH2C6H3—(CN)2(3,5)
H
H
CH3
53.
OCH2C6H3—(CN)2(3,5)
H
H
H
54.
OCH2C6H3—(CN)2(3,5)
H
H
CH3
55.
OCH2C6H3—(CONH2)2(3,5)
H
H
H
56.
OCH2C6H3—(CONH2)2(3,5)
H
H
CH3
57.
OCH2C6H3—(CONH2)2(3,5)
H
H
H
58.
OCH2C6H3—(CONH2)2(3,5)
H
H
CH3
59.
OCH2CH2C6H5
H
H
H
60.
OCH2CH2C6H5
H
H
CH3
61.
OCH2C6H4C6H4CN(2)
H
H
H
62.
OCH2C6H4C6H4CN(2)
H
H
CH3
63.
OCH2C6H4C6H4CONH2(2)
H
H
H
64.
OCH2C6H4C6H4CONH2(2)
H
H
CH3
TABLE VIIb
Ex. #
X1
X
X2
R
1.
OCH2CH═CH2
H
H
H
2.
OCH2CH═CH2
H
H
CH3
3.
NHSO2CH3
H
H
H
4.
NHSO2CH3
H
H
CH3
5.
OCH2C6H5
H
H
H
6.
OCH2C6H5
H
H
CH3
7.
OCH2C6H4—Cl(3)
H
H
H
8.
OCH2C6H4—Cl(3)
H
H
CH3
9.
OCH2C6H4—Cl(4)
H
H
H
10.
OCH2C6H4—Cl(4)
H
H
CH3
11.
OCH2C6H4—F(3)
H
H
H
12.
OCH2C6H4—F(3)
H
H
CH3
13.
OCH2C6H4—F(4)
H
H
H
14.
OCH2C6H4—F(4)
H
H
CH3
15.
OCH2C6H4—CF3(3)
H
H
H
16.
OCH2C6H4—CF3(3)
H
H
CH3
17.
OCH2C6H4—CF3(4)
H
H
H
18.
OCH2C6H4—CF3(4)
H
H
CH3
19.
OCH2C6H4—NO2(3)
H
H
H
20.
OCH2C6H4—NO2(3)
H
H
CH3
21.
OCH2C6H4—NO2(4)
H
H
H
22.
OCH2C6H4—NO2(4)
H
H
CH3
23.
OCH2C6H4—NHSO2CH3(3)
H
H
H
24.
OCH2C6H4—NHSO2CH3(3)
H
H
CH3
25.
OCH2C6H4—NHSO2CH3(4)
H
H
H
26.
OCH2C6H4—NHSO2CH3(4)
H
H
CH3
27.
OCH2C6H4—CN(3)
H
H
H
28.
OCH2C6H4—CN(3)
H
H
CH3
29.
OCH2C6H4—CN(4)
H
H
H
30.
OCH2C6H4—CN(4)
H
H
CH3
31.
OCH2C6H4—CONH2(3)
H
H
H
32.
OCH2C6H4—CONH2(3)
H
H
CH3
33.
OCH2C6H4—CONH2(4)
H
H
H
34.
OCH2C6H4—CONH2(4)
H
H
CH3
35.
OCH2C6H4—CH2CN(3)
H
H
H
36.
OCH2C6H4—CH2CN(3)
H
H
CH3
37.
OCH2C6H4—CH2CN(4)
H
H
H
38.
OCH2C6H4—CH2CN(4)
H
H
CH3
39.
OCH2C6H4—CH2CONH2(3)
H
H
H
40.
OCH2C6H4—CH2CONH2(3)
H
H
CH3
41.
OCH2C6H4—CH2CONH2(4)
H
H
H
42.
OCH2C6H4—CH2CONH2(4)
H
H
CH3
43.
OCH2C6H4—OCH2CN(3)
H
H
H
44.
OCH2C6H4—OCH2CN(3)
H
H
CH3
45.
OCH2C6H4—OCH2CN(4)
H
H
H
46.
OCH2C6H4—OCH2CN(4)
H
H
CH3
47.
OCH2C6H4—OCH2CONH2(3)
H
H
H
48.
OCH2C6H4—OCH2CONH2(3)
H
H
CH3
49.
OCH2C6H4—OCH2CONH2(4)
H
H
H
50.
OCH2C6H4—OCH2CONH2(4)
H
H
CH3
51.
OCH2C6H3—(CN)2(3,5)
H
H
H
52.
OCH2C6H3—(CN)2(3,5)
H
H
CH3
53.
OCH2C6H3—(CN)2(3,5)
H
H
H
54.
OCH2C6H3—(CN)2(3,5)
H
H
CH3
55.
OCH2C6H3—(CONH2)2(3,5)
H
H
H
56.
OCH2C6H3—(CONH2)2(3,5)
H
H
CH3
57.
OCH2C6H3—(CONH2)2(3,5)
H
H
H
58.
OCH2C6H3—(CONH2)2(3,5)
H
H
CH3
59.
OCH2CH2C6H5
H
H
H
60.
OCH2CH2C6H5
H
H
CH3
61.
OCH2C6H4C6H4CN(2)
H
H
H
62.
OCH2C6H4C6H4CN(2)
H
H
CH3
63.
OCH2C6H4C6H4CONH2(2)
H
H
H
64.
OCH2C6H4C6H4CONH2(2)
H
H
CH3
TABLE VIIc
Ex. #
X2
X
X1
R
1.
OCH2CH═CH2
H
H
H
2.
OCH2CH═CH2
H
H
CH3
3.
NHSO2CH3
H
H
H
4.
NHSO2CH3
H
H
CH3
5.
OCH2C6H5
H
H
H
6.
OCH2C6H5
H
H
CH3
7.
OCH2C6H4—Cl(3)
H
H
H
8.
OCH2C6H4—Cl(3)
H
H
CH3
9.
OCH2C6H4—Cl(4)
H
H
H
10.
OCH2C6H4—Cl(4)
H
H
CH3
11.
OCH2C6H4—F(3)
H
H
H
12.
OCH2C6H4—F(3)
H
H
CH3
13.
OCH2C6H4—F(4)
H
H
H
14.
OCH2C6H4—F(4)
H
H
CH3
15.
OCH2C6H4—CF3(3)
H
H
H
16.
OCH2C6H4—CF3(3)
H
H
CH3
17.
OCH2C6H4—CF3(4)
H
H
H
18.
OCH2C6H4—CF3(4)
H
H
CH3
19.
OCH2C6H4—NO2(3)
H
H
H
20.
OCH2C6H4—NO2(3)
H
H
CH3
21.
OCH2C6H4—NO2(4)
H
H
H
22.
OCH2C6H4—NO2(4)
H
H
CH3
23.
OCH2C6H4—NHSO2CH3(3)
H
H
H
24.
OCH2C6H4—NHSO2CH3(3)
H
H
CH3
25.
OCH2C6H4—NHSO2CH3(4)
H
H
H
26.
OCH2C6H4—NHSO2CH3(4)
H
H
CH3
27.
OCH2C6H4—CN(3)
H
H
H
28.
OCH2C6H4—CN(3)
H
H
CH3
29.
OCH2C6H4—CN(4)
H
H
H
30.
OCH2C6H4—CN(4)
H
H
CH3
31.
OCH2C6H4—CONH2(3)
H
H
H
32.
OCH2C6H4—CONH2(3)
H
H
CH3
33.
OCH2C6H4—CONH2(4)
H
H
H
34.
OCH2C6H4—CONH2(4)
H
H
CH3
35.
OCH2C6H4—CH2CN(3)
H
H
H
36.
OCH2C6H4—CH2CN(3)
H
H
CH3
37.
OCH2C6H4—CH2CN(4)
H
H
H
38.
OCH2C6H4—CH2CN(4)
H
H
CH3
39.
OCH2C6H4—CH2CONH2(3)
H
H
H
40.
OCH2C6H4—CH2CONH2(3)
H
H
CH3
41.
OCH2C6H4—CH2CONH2(4)
H
H
H
42.
OCH2C6H4—CH2CONH2(4)
H
H
CH3
43.
OCH2C6H4—OCH2CN(3)
H
H
H
44.
OCH2C6H4—OCH2CN(3)
H
H
CH3
45.
OCH2C6H4—OCH2CN(4)
H
H
H
46.
OCH2C6H4—OCH2CN(4)
H
H
CH3
47.
OCH2C6H4—OCH2CONH2(3)
H
H
H
48.
OCH2C6H4—OCH2CONH2(3)
H
H
CH3
49.
OCH2C6H4—OCH2CONH2(4)
H
H
H
50.
OCH2C6H4—OCH2CONH2(4)
H
H
CH3
51.
OCH2C6H3—(CN)2(3,5)
H
H
H
52.
OCH2C6H3—(CN)2(3,5)
H
H
CH3
53.
OCH2C6H3—(CN)2(3,5)
H
H
H
54.
OCH2C6H3—(CN)2(3,5)
H
H
CH3
55.
OCH2C6H3—(CONH2)2(3,5)
H
H
H
56.
OCH2C6H3—(CONH2)2(3,5)
H
H
CH3
57.
OCH2C6H3—(CONH2)2(3,5)
H
H
H
58.
OCH2C6H3—(CONH2)2(3,5)
H
H
CH3
59.
OCH2CH2C6H5
H
H
H
60.
OCH2CH2C6H5
H
H
CH3
61.
OCH2C6H4C6H4CN(2)
H
H
H
62.
OCH2C6H4C6H4CN(2)
H
H
CH3
63.
OCH2C6H4C6H4CONH2(2)
H
H
H
64.
OCH2C6H4C6H4CONH2(2)
H
H
CH3