US 8,541,475 B2Granted

MAO-B inhibitors useful for treating obesity

AssigneeJenrin Discovery

InventorsJohn Francis McElroy, Robert J. Chorvat, Parthasarathi Rajagopalan

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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).

Claims21

Dependent claims

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.

12 more elements

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.

12 more elements

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.

12 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/650,642Filed 31 Dec 2009 · division
Priority: 2 Jun 2005
Published: US 2010/0168068 A11 Jul 2010
Granted: 24 Sep 2013
Term ends: Not estimatedThe source records don’t support an estimate.

Classification19 codes

C07F 9/3808
Not used, see subgroups: acyclic saturated acids which can have further substituents on alkyl
A61P 3/00
Drugs for disorders of the metabolism
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics

Family

Application60/686,585Us provisional application · filed 2 Jun 2005
Application11/445,044Parent of this division · filed 1 Jun 2006
US 2010/0168068 A1Pre-grant publication · published 1 Jul 2010
US 7,649,115 B2Parent of this division
US 2007/0088004 A1Published application
US 8,541,475 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

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.

12 more elements

Facts

Application

12/650,642Filed 31 Dec 2009 · division

Priority

2 Jun 2005

Published

US 2010/0168068 A11 Jul 2010

Granted

24 Sep 2013

Term ends

Not estimatedThe source records don’t support an estimate.

Classification19 codes

C07F 9/3808
Not used, see subgroups: acyclic saturated acids which can have further substituents on alkyl
A61P 3/00
Drugs for disorders of the metabolism
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics

Family

Application60/686,585Us provisional application · filed 2 Jun 2005

Application11/445,044Parent of this division · filed 1 Jun 2006

US 2010/0168068 A1Pre-grant publication · published 1 Jul 2010

US 7,649,115 B2Parent of this division

US 2007/0088004 A1Published application

US 8,541,475 B2This patent

From the US filing history. Foreign family members aren’t listed.