# US 7,744,889 B2 · Alpha, beta-unsaturated sulfoxides for treating proliferative disorders

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 7,744,889 B2
- Document ID: US7744889B2
- Status: Granted
- Kind: B2
- Application number: 10/574,993
- Filed: 2004-11-08
- Published: 2006-12-14
- Granted: 2010-06-29
- Earliest claimed: 2003-11-14
- Assignees: Temple University of the Commonwealth System of Higher Education
- Inventors: E. Premkumar Reddy; M. V. Ramana Reddy; Stanley C. Bell
- Web page: https://patentgrep.com/patent/US7744889B2

## CPC

- C07C 317/44: having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 19/04: for non-specific disorders of the connective tissue
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- C07C 317/10: of an unsaturated carbon skeleton containing rings
- C07C 317/18: with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C 317/28: with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
- C07D 207/333: Radicals substituted by oxygen or sulfur atoms
- C07D 213/34: to which a second hetero atom is attached
- C07D 277/26: Radicals substituted by sulfur atoms
- C07D 307/38: with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D 333/18: by sulfur atoms
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

αβ-Unsaturated sulfoxides of Formula I: are useful as antiproliferative agents including, for example, anticancer agents, and as radioprotective and chemoprotective agents.

## Claims

### Claim 1

A compound of Formula IA:
wherein:
A1 is aryl or heteroaryl and x is 0, 1, 2, 3, 4 or 5;
either B1 is aryl and y is 1, 2, 3, 4 or 5, or B1 is heteroaryl and y is 0, 1, 2, 3, 4 or 5;
provided that x does not exceed the number of substitutable positions of the ring to which each Ra is attached; and y does not exceed number of substitutable positions of the ring to which each Rb is attached;
n is 1;
R1 is —H, —(C1-C8)hydrocarbyl, —CN, —CO2(C1-C6)alkyl or halo(C1-C6)alkyl;
the configuration of the substituents on the carbon-carbon double bond is either E- or Z—;
the configuration of the substituents on the sulfoxide sulfur atom is R—, S— or any mixture of R— and S—;
each Ra is independently selected from the group consisting of halogen; —(C1-C8)hydrocarbyl, —C(═O)R2, —NR22, —NHC(═O)R3, —NHSO2R3, —NHR4, —NHCR2R4C(═O)R6, —C(═O)OR2, —C(═O)NHR2; —NO2, —CN, —OR2, —P(═O)(OH)2, dimethylamino(C2-C6 alkoxy), —NHC(═NH)NHR2, —(C1-C6)haloalkyl, —(C1-C6)haloalkoxy and —N═CH—R7;
each Rb attached to aryl is independently selected from the group consisting of —C(═O)R2, halogen, —NO2, —CN, —OR2, —C(═O)OR2, —NR22, (C1-C6)haloalkyl and (C1-C6)haloalkoxy;
each Rb attached to heteroaryl is independently selected from the group consisting of —(C1-C8)hydrocarbyl, —C(═O)R2, halogen, —NO2, —CN, —OR2, —C(═O)OR2, —NR22, (C1-C6)haloalkyl and (C1-C6)haloalkoxy;
each R2 is independently selected from the group consisting of —H and —(C1-C8)hydrocarbyl;
each R3 is independently selected from the group consisting of —H, —(C1-C8)hydrocarbyl, —O(C1-C8)hydrocarbyl, substituted and unsubstituted aryl, substituted heterocyclyl(C1-C3)alkyl, heteroaryl(C1-C3)alkyl, —(C2-C10)heteroalkyl, —(C1-C6)haloalkyl, —CR2R4NHR5, —N(R2)2, —(C1-C3)alkyleneNH2, —(C1-C3)alkylene-N(CH3)2, —(C1-C3)perfluoroalkylene-N(CH3)2, —(C1-C3)alkylene-N+((C1-C3)alkyl)3, —(C1-C3)alkylene-N+(CH2CH2OH)3, —(C1-C3)alkylene-OR2, —(C1-C4)alkylene-CO2R2, —(C1-C4)alkylene-C(═O)halogen, halo(C1-C3)alkyl-, —(C1-C3)alkylene-C(═O)(C1-C3)alkyl, and —(C1-C4)perfluoroalkylene-CO2R2;
each R4 is independently selected from the group consisting of —H, —(C1-C6)alkyl, —(CH2)3—NH—C(NH2)(═NH), —CH2C(═O)NH2, —CH2COOH, —CH2SH, —(CH2)2C(═O)—NH2, —(CH2)2COOH, —CH2-(2-imidazolyl), —(CH2)4—NH2, —(CH2)2—S—CH3, phenyl, —CH2-phenyl, —CH2—OH, —CH(OH)—CH3, —CH2-(3-indolyl), and —CH2-(4-hydroxyphenyl);
each R5 is independently selected from the group consisting of —H and a carboxy terminally linked peptidyl residue containing from 1 to 3 amino acids in which the terminal amino group of the peptidyl residue is present as a functional group selected from the group consisting of —NH2 and —NHC(═O)(C1-C6)alkyl, —NH(C1-C6)alkyl, —N(C1-C6alkyl)2 and —NHC(═O)O(C1-C7)hydrocarbyl;
each R6 is independently selected from the group consisting of —OR2 and an N-terminally linked peptidyl residue containing from 1 to 3 amino acids in which the terminal carboxyl group of the peptidyl residue is present as a functional group selected from the group consisting of —CO2R2 and —C(═O)NR22; and
each R7 is independently selected from the group consisting of substituted and unsubstituted aryl and substituted and unsubstituted heteroaryl;
* indicates that, when R1 is other than —H, the configuration of the substituents on the designated carbon atom is R—, S— or any mixture of R— and S—; or a salt of such a compound.

### Claim 2 (depends on 1)

A compound according to claim 1 of Formula IAz:
or a salt thereof.

### Claim 3 (depends on 1)

A compound according to claim 1 of the Formula IAe:
or a salt thereof.

### Claim 4 (depends on 1)

A compound according to claim 1, or a salt thereof, wherein the sum of x and y is greater than zero.

### Claim 5 (depends on 4)

A compound according to claim 4, or a salt thereof, wherein A1 is an aryl radical.

### Claim 6 (depends on 5)

A compound according to claim 5 selected from the group consisting of: (1E)-2-(4-fluorophenyl)-1-[(naphthylmethyl)sulfinyl]ethene; (1E)-2-(4-chlorophenyl)-1-[(naphthylmethyl)sulfinyl]ethene; (1E)-2-(4-bromophenyl)-1-[(naphthylmethyl)sulfinyl]ethene; (1E)-2-(2-nitrophenyl)-1-[(naphthylmethyl)sulfinyl]-ethene; (1E)-2-(3-nitrophenyl)-1-[(naphthylmethyl)sulfinyl]ethene; and (1E)-2-(4-nitrophenyl)-1-[(naphthylmethyl)sulfinyl]ethene.

### Claim 7 (depends on 5)

A compound according to claim 5, of Formula IB:
or a salt thereof.

### Claim 8 (depends on 7)

A compound according to claim 7, or a salt thereof, wherein each Ra is independently selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)alkoxy, —NO2, —CN, —C(═O)OR2, —OH, —NH2, (C1-C6)trifluoroalkoxy and —CF3.

### Claim 9 (depends on 7)

A compound according to claim 7, of Formula IC:
or a salt thereof.

### Claim 10 (depends on 9)

A compound according to claim 9 wherein each Ra is independently selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)alkoxy, —NO2, —CN and —CF3, and each Rb is independently selected from the group consisting of halogen, (C1-C6)alkoxy, —NO2, —CN and —CF3.

### Claim 11 (depends on 9)

A compound according to claim 9, or a salt thereof, wherein the configuration of the substituents on the carbon-carbon double bond is E-.

### Claim 12 (depends on 11)

A compound according to claim 11, or a salt thereof, wherein x is 0, 1 or 2and y is 1 or 2.

### Claim 13 (depends on 11)

A compound according to claim 11 selected from the group consisting of: (1E)-1-{[(3-amino-4-methoxyphenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxyphenyl)ethene; (1E)-1-{[(3-hydroxy-4-methoxyphenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxyphenyl)ethene; (1E)-1-{[(4-methoxy-3-nitrophenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxyphenyl)ethene; 2-({[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]-sulfinyl}-methyl)-2-methoxyphenyl]amino}sulfonyl)acetic acid; 2-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}acetic acid; [5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]aminocarboxamidine; 2-{[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]amino}acetic acid; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl](3,5-dinitro-phenyl)carboxamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl](3,5-diaminophenyl)carboxamide; N-[5-({[(1E)-2-(2,4,6-trimethoxy-phenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-chloroacetamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-(4-methyl-piperazinyl)acetamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]benzamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl](4-nitrophenyl)carboxamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl](4-aminophenyl)carboxamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)-vinyl]sulfinyl}methyl)-2-methoxyphenyl](2R)-2,6-diaminohexanamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl](2R)-2-amino-3-hydroxypropanamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl](2S)-2-amino-3-hydroxypropanamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]aminamide; (1E)-1-({[4-methoxy-3-(methylamino)phenyl]methyl}sulfinyl)-2-(2,4,6-trimethoxyphenyl)ethene; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]acetamide; [5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl][(2,4-dinitrophenyl)sulfonyl]amine; [5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl][(2,4-diaminophenyl)sulfonyl]amine; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-(dimethylamino)-acetamide; 2-{[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxy-phenyl]amino}propanoic acid; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl][4-(4-methylpiperazinyl)phenyl]carboxamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-hydroxyacetamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-pyridylacetamide; {N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]carbamoyl}methyl acetate; N-[5-({[(1E)-2-(2,4,6-trimethoxy-phenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-hydroxypropanamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-(triethylamino)acetamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]-2-[tris(2-hydroxyethyl)amino]acetamide; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-hydroxy-2-methylpropanamide; 1-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}-isopropyl acetate; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2,2,2-trifluoroacetamide; [5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl][(trifluoro-methyl)sulfonyl]amine; 3-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]-sulfinyl}methyl)-2-methoxyphenyl]carbamoyl}propanoic acid; 3-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}propanoyl chloride; 3-[({N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}methyl)oxycarbonyl]propanoic acid; 4-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}butanoic acid; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-(phosphonooxy)acetamide, disodium salt; 4-{[5-({[(1E)-2-(2,4,6-trimethoxy-phenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]amino}butanoic acid; 3-{[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]amino}propanoic acid; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]methoxycarboxamide; [5-({[(1E)-2-(2,4,6-trimethoxy-phenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl][(4-methoxyphenyl)sulfonyl]amine; {N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]carbamoyl}ethyl acetate; methyl-3-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]-sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}propanoate; ethyl-2-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}acetate; N-[5-({[(1E)-2-(2,4,6-trimethoxy-phenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2,2,3,3,3-pentafluoropropanamide; methyl-2-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]-sulfinyl}methyl)-2-methoxy-phenyl]carbamoyl}-2,2-difluoroacetate; 3-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}-2,2,3,3-tetrafluoropropanoic acid; N-[5-({[(1E)-2-(2,4,6-trimethoxy-phenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-aminoacetamide; 2-{N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}-methyl)-2-methoxyphenyl]carbamoyl}-2,2-difluoroacetic acid; N-[5-({[(1E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfinyl}methyl)-2-methoxyphenyl]-2-(dimethylamino)-2,2-difluoroacetamide, 4-((1E)-2-{[(4-fluorophenyl)methyl]sulfinyl}vinyl)benzoic acid; 4-((1E)-2-{[(4-iodophenyl)methyl]-sulfinyl}vinyl)benzoic acid; 4-((1E)-2-{[(4-chlorophenyl)methyl]sulfinyl}vinyl)benzoic acid; 1-[5-((1E)-2-{[(4-chlorophenyl)methyl]sulfinyl}vinyl)-2-fluoro-phenyl]-2-(dimethylamino)ethan-1-one; (1E)-2-(2,4-difluorophenyl)-1-{[(4-bromophenyl)methyl]-sulfinyl}ethene; (1E)-2-(3-amino-4-fluorophenyl)-1-{[(4-chlorophenyl)methyl]sulfinyl}-ethene; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(2,3 ,4,5,6-pentafluorophenyl)-ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2,3,4,5,6-pentafluoro-phenyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(2,3,4,5,6-pentafluoro-phenyl)ethene; (1E)-2-(4-fluorophenyl)-1-{[(2,3,4,5,6-pentafluorophenyl)-methyl]sulfinyl}ethene; (1E)-2-(4-chlorophenyl)-1-{[(2,3,4,5,6-pentafluorophenyl)-methyl]sulfinyl}ethene; (1E)-2-(4-bromophenyl)-1-{[(2,3,4,5,6-pentafluorophenyl)-methyl]sulfinyl}ethene; (1E)-1-{[(3,4-dichlorophenyl)methyl]sulfinyl}-2-(2,3,4,5,6-pentafluorophenyl)ethene; (1E)-1-{[(4-iodophenyl)methyl]sulfinyl}-2-(2,3,4,5,6-pentafluorophenyl)ethene; (1E) 1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(2-hydroxy-3,5-dinitrophenyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(2-hydroxy-3,5-dinitrophenyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2-hydroxy-3,5-dinitrophenyl)ethene; (1E)-1-{[(2,4-dichlorophenyl)methyl]sulfinyl}-2-(2-hydroxy-3,5-dinitrophenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxy-phenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(3,4,5-trimethoxy-phenyl)ethene; (1E)-1-{[(2-nitro-4,5-dimethoxyphenyl)methyl]sulfinyl}-2-(3,4,5-trimethoxyphenyl)ethene; (1E)-1-{[(2-nitro-4,5-dimethoxyphenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxyphenyl)ethene; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(2,3,4-trifluorophenyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2,3,4-trifluorophenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(2,6-methoxy-4-hydroxyphenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(2,3,5,6-tetrafluorophenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(2,4,5-trimethoxyphenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(2,3,4-trimethoxyphenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(3-nitro-4-hydroxy-5-methoxyphenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(3,4-dimethoxy-6-nitrophenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(3,4-dimethoxy-5-iodophenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(2,6-dimethoxy-4-fluorophenyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(2-hydroxy-4,6-dimethoxyphenyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxyphenyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2,6-dimethoxy-4-fluorophenyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2-hydroxy-4,6-dimethoxyphenyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxyphenyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(2,6-dimethoxy-4-fluorophenyl)ethene; (1E)-1-{[(2,4,6-trimethoxyphenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxyphenyl)ethene; (1E)-1-{[(2,3,4-trimethoxyphenyl)methyl]sulfinyl}-2-(2,6-dimethoxyphenyl)ethene; (1E)-1-{[(3,4,5-trimethoxyphenyl)methyl]sulfinyl}-2-(2,4,6-trimethoxyphenyl)ethene; (1E)-1-{[(3,4,5-trimethoxyphenyl)methyl]sulfinyl}-2-(2,6-dimethoxyphenyl)ethene; (1E)-1-{[(3,4,5-trimethoxyphenyl)methyl]sulfinyl}-2-(4-fluorophenyl)ethene; (1E)-2-(4-fluorophenyl)-1-({[4-(trifluoromethyl)phenyl]methyl}-sulfinyl)ethene; (1E)-2-(4-chlorophenyl)-1-({[4-(trifluoromethyl)phenyl]methyl}-sulfinyl)ethene; (1E)-2-(4-bromophenyl)-1-({[4-(trifluoromethyl)phenyl]methyl}-sulfinyl)ethene; (1E)-1-{[(2,4-dichlorophenyl)methyl]sulfinyl}-2-(4-fluorophenyl)ethene; (1E)-1-{[(2,4-dichlorophenyl)methyl]sulfinyl}-2-(4-chloro-phenyl)ethene; (1E)-1-{[(3,4-dichlorophenyl)methyl]sulfinyl}-2-(4-fluoro-phenyl)ethene; (1E)-1-{[(3,4-dichloro-phenyl)methyl]sulfinyl}-2-(4-chloro-phenyl)ethene; (1E)-1-{[(3,4-dichloro-phenyl)methyl]sulfinyl}-2-(4-bromo-phenyl)ethene; (1E)-2-(4-fluorophenyl)-1-{[(4-nitrophenyl)methyl]sulfinyl}-ethene; 4-({[(1E)-2-(4-fluorophenyl)vinyl]-sulfinyl }methyl)benzene-carbonitrile; 4-({[(1E)-2-(4-chlorophenyl)vinyl]sulfinyl}-methyl)benzene-carbonitrile; 4-({[(1E)-2-(4-bromophenyl)vinyl]sulfinyl}-methyl)benzene-carbonitrile; (1E)-2-(3,4-difluorophenyl)-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(3-chloro-4-fluorophenyl)-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(2-chloro-4-fluorophenyl)-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(2,4-dichlorophenyl)-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(3,4-dichlorophenyl)-1-{[(4-chlorophenyl)-methyl]sulfinyl}ethene; (1E)-2-(2,3-dichlorophenyl)-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(4-fluorophenyl)-1-{[(4-iodophenyl)methyl]-sulfinyl}ethene; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(4-iodophenyl)-ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(4-iodophenyl)-ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(4-iodophenyl)-ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(4-chlorophenyl)-ethene; (1E)-2-(4-bromophenyl)-1-{[(4-iodophenyl)methyl]sulfinyl}ethene; (1E)-1-{[(4-iodophenyl)methyl]sulfinyl}-2-(4-nitrophenyl)-ethene; (1E)-1-{[(4-iodophenyl)methyl]sulfinyl}-2-(2-nitrophenyl)-ethene; (1E)-2-(4-iodophenyl)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-ethene; (1E)-1-{[(2,4-dichlorophenyl)methyl]sulfinyl}-2-(4-iodophenyl)-ethene; (1E)-2-(3,4-dichlorophenyl)-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(2-nitrophenyl)-1-{[(4-fluoro-phenyl)methyl]sulfinyl}-ethene; (1E)-2-(3-nitrophenyl)-1-{[(4-fluorophenyl)methyl]-sulfinyl}-ethene; (1E)-2-(4-nitrophenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}-ethene; (1E)-2-(2-trifluoromethylphenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}ethene; (1E)-2-(3-trifluoromethylphenyl)-1-{[(4-fluorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(4-trifluoromethylphenyl)-1-{[(4-fluorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(2-trifluoro-methyl-4-fluorophenyl)-1-{[(4-fluorophenyl)-methyl]sulfinyl}ethene; (1E)-2-(2-nitrophenyl)-1-{[(4-chlorophenyl)methyl]sulfinyl}-ethene; (1E)-2-(3-nitrophenyl)-1-{[(4-chlorophenyl)methyl]sulfinyl}-ethene; (1E)-2-(4-nitrophenyl)-1-{[(4-chlorophenyl)-methyl]sulfinyl}-ethene; (1E)-2-(2-trifluoromethylphenyl)-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(3-trifluoromethylphenyl)-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(4-trifluoromethylphenyl)-1-{[(4-chlorophenyl)-methyl]sulfinyl}ethene; (1E)-2-(2-trifluoromethyl-4-fluorophenyl)-1-{[(4-chlorophenyl)-methyl]sulfinyl}ethene; (1E)-2-(2-nitrophenyl)-1-{[(2,4-dichlorophenyl)methyl]sulfinyl}-ethene; (1E)-2-(2-trifluoromethyl-4-fluorophenyl)-1-{[(2,4-dichloro-phenyl)methyl]sulfinyl}ethene; (1E)-2-(2-nitrophenyl)-1-{[(4-bromophenyl)methyl]sulfinyl}ethene; (1E)-2-(3-nitrophenyl)-1-{[(4-bromophenyl)methyl]sulfinyl}ethene; (1E)-2-(4-nitrophenyl)-1-{[(4-bromophenyl)methyl]sulfinyl}ethene; (1E)-2-(2-trifluoromethylphenyl)-1-{[(4-bromophenyl)methyl]sulfinyl}ethene; (1E)-2-(3-trifluoromethylphenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}ethene; (1E)-2-(4-trifluoromethylphenyl)-1-{[(4-bromophenyl)methyl]sulfinyl}ethene; (1E)-2-(2-nitrophenyl)-1-{[(4-cyanophenyl)methyl]sulfinyl}ethene; (1E)-2-(3-nitrophenyl)-1-{[(4-cyanophenyl)-methyl]sulfinyl}ethene; (1E)-2-(4-nitrophenyl)-1-{[(4-cyanophenyl)-methyl]sulfinyl}ethene; (1E)-2-(4-fluorophenyl)-1-{[(4-methylphenyl)methyl]sulfinyl}-ethene; (1E)-2-(4-bromophenyl)-1-{[(4-methylphenyl)methyl]sulfinyl}ethene; (1E)-2-(2-nitrophenyl)-1-{[(4-methylphenyl)methyl]sulfinyl}ethene; (1E)-2-(3-nitrophenyl)-1-{[(4-methylphenyl)methyl]sulfinyl}ethene; (1E)-2-(4-nitrophenyl)-1-{[(4-methylphenyl)methyl]sulfinyl}ethene; (1E)-2-(4-fluorophenyl)-1-{[(4-methoxyphenyl)methyl]sulfinyl}ethene; (1E)-2-(4-chlorophenyl)-1-{[(4-methoxyphenyl)methyl]-sulfinyl}ethene; (1E)-2-(4-bromophenyl)-1-{[(4-methoxyphenyl)methyl]-sulfinyl}ethene; (1E)-2-(2-nitrophenyl)-1-{[(4-methoxyphenyl)methyl]sulfinyl}ethene; (1E)-2-(3-nitrophenyl)-1-{[(4-methoxyphenyl)methyl]sulfinyl}ethene; (1E)-2-(4-nitrophenyl)-1-{[(4-methoxy-phenyl)methyl]sulfinyl}ethene; (1E)-2-(4-chlorophenyl)-1-{[(4-nitrophenyl)methyl]-sulfinyl}ethene; (1E)-2-(4-fluorophenyl)-1-{[(4-nitrophenyl)methyl]sulfinyl}ethene; and salts thereof.

### Claim 14 (depends on 9)

A compound according to claim 9 wherein:
Ra is selected from the group consisting of chlorine, fluorine and bromine, and said Ra is bonded to the para position of the ring to which it is attached;
x is 0 or 1;
Rb is selected from the group consisting of chlorine, fluorine, bromine, and methoxy, and said Rb is bonded to the ortho or para position of the ring to which it is bonded; and
y is 1, 2 or 3.

### Claim 15 (depends on 14)

A compound according to claim 14 wherein the configuration of the substituents on the carbon-carbon double bond is E-.

### Claim 16 (depends on 15)

A compound according to claim 15 selected from the group consisting of: (1E)-2-(2-chlorophenyl)-1-[benzylsulfinyl]ethene; (1E)-2-(4-chlorophenyl)-1-[benzylsulfinyl]ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(4-fluorophenyl)ethene; (1E)-2-(4-chlorophenyl)-1-{[(4-chlorophenyl)methyl]sulfinyl}-ethene; (1E)-2-(4-fluorophenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}ethene; (1E)-2-(2,4-difluorophenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(4-fluorophenyl)ethene; (1E)-2-(4-bromophenyl)-1-{[(4-bromophenyl)methyl]sulfinyl}ethene; (1E)-2-(4-bromophenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}ethene; and (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(4-chlorophenyl)ethene.

### Claim 17 (depends on 9)

A compound according to claim 9, wherein:
each Ra is independently selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)alkoxy, —NO2, —CN and —CF3, and each Rb is independently selected from the group consisting of (C1-C6)alkoxy, halogen and nitro, and is bonded to the ortho or para position of the ring to which it is attached;
x is 0, 1, 2 or 3; and
y is 1, 2 or 3.

### Claim 18 (depends on 17)

A compound according to claim 17, wherein the configuration of the substituents on the carbon-carbon double bond is Z—.

### Claim 19 (depends on 18)

A compound according to claim 18 selected from the group consisting of: (1Z)-2-(4-chlorophenyl)-1-[benzylsulfinyl]ethene; (1Z)-2-(4-chlorophenyl)-1-{[(4-chlorophenyl)methyl]sulfinyl}-ethene; (1Z)-2-(4-chlorophenyl)-1-{[(2-chlorophenyl)methyl]sulfinyl}-ethene; (1Z)-2-(4-chlorophenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}ethene; (1Z)-2-(4-fluorophenyl)-1-[benzylsulfinyl]ethene; (1Z)-2-(4-fluorophenyl)-1-{[(4-chlorophenyl)methyl]sulfinyl}ethene; (1Z)-2-(4-fluoro-phenyl)-1-{[(2-chlorophenyl)methyl]sulfinyl}ethene; (1Z)-2-(4-fluorophenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}ethene; (1Z)-2-(4-bromophenyl)-1-[benzylsulfinyl]ethene; (1Z)-2-(4-bromophenyl)-1-{[(4-chlorophenyl)methyl]sulfinyl}ethene; (1Z)-2-(4-bromophenyl)-1-{[(2-chlorophenyl)methyl]sulfinyl}ethene; (1Z)-2-(4-bromophenyl)-1-{[(4-fluorophenyl)methyl]sulfinyl}ethene; and (1Z)-2-(4-fluorophenyl)-1-{[(4-iodophenyl)methyl]sulfinyl}ethene.

### Claim 20 (depends on 4)

A compound according to claim 4, of Formula ID:
wherein B2 is selected from the group consisting of heteroaryl and aryl other than phenyl
or a salt thereof.

### Claim 21 (depends on 20)

A compound according to claim 20, or a salt thereof, wherein B2 is heteroaryl.

### Claim 22 (depends on 20)

A compound according to claim 20, or a salt thereof, wherein B2 is selected from the group consisting of furyl, thienyl, pyrrolyl, thiazolyl, pyridyl, thienyl-1,1-dioxide, anthryl, and naphthyl.

### Claim 23 (depends on 22)

A compound according to claim 22, or a salt thereof, wherein the configuration of the substituents on the carbon-carbon double bond is E-.

### Claim 24 (depends on 23)

A compound according to claim 23, or a salt thereof, wherein Ra is independently selected from the group consisting of halogen, (C1-C3)alkoxy, —CN, —NO2, and —CF3.

### Claim 25 (depends on 24)

A compound of claim 24 selected from the group consisting of: (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(2-pyridyl)ethene; (1E)-1-{[(4-fluorophenyl)methyl]-sulfinyl}-2-(3-pyridyl)ethene; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(4-pyridyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2-pyridyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(3-pyridyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(4-pyridyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(2-pyridyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]-sulfinyl}-2-(3-pyridyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(4-pyridyl)ethene; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(2-thienyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2-thienyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(2-thienyl)ethene; (1E)-2-(4-bromo(2-thienyl))-1-{[(4-fluorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(5-bromo(2-thienyl))-1-{[(4-fluorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(5-bromo(2-thienyl))-1-{[(4-chlorophenyl)methyl]-sulfinyl}ethene; (1E)-2-(5-bromo(2-thienyl))-1-{[(4-bromophenyl)methyl]-sulfinyl}ethene; 2-((1E)-2-{[(4-fluorophenyl)methyl]sulfinyl}vinyl)thiole-1,1-dione; 2-((1E)-2-{[(4-chlorophenyl)-methyl]sulfinyl}vinyl)thiole-1,1-dione; 2-((1E)-2-{[(4-bromophenyl)methyl]-sulfinyl}vinyl)thiole-1,1-dione; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(3-thienyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(3-thienyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(3-thienyl)ethene; (1E)-1-{[(4-iodophenyl)methyl]sulfinyl}-2-(3-thienyl)ethene; (1E)-1-{[(4-methylphenyl)methyl]sulfinyl}-2-(3-thienyl)ethene; (1E)-1-{[(4-methoxyphenyl)-methyl]sulfinyl}-2-(3-thienyl)ethene; (1E)-1-{[(4-trifluoromethylphenyl)methyl]-sulfinyl}-2-(3-thienyl)-ethene; (1E)-1-{[(2,4-dichlorophenyl)methyl]sulfinyl}-2-(3-thienyl)-ethene; (1E)-1-{[(3,4-dichlorophenyl)methyl]sulfinyl}-2-(3-thienyl)-ethene; (1E)-1-{[(4-cyanophenyl)methyl]sulfinyl}-2-(3-thienyl)ethene; (1E)-1-{[(4-nitrophenyl)methyl]sulfinyl}-2-(3-thienyl)ethene; 3-((1E)-2-{[(4-fluorophenyl)methyl]sulfinyl}vinyl)thiole-1,1-dione; 3-((1E)-2-{[(4-chlorophenyl)methyl]sulfinyl}vinyl)thiole-1,1-dione; 3-((1E)-2-{[(4-bromophenyl)-methyl]sulfinyl}vinyl)thiole-1,1-dione; 3-((1E)-2-{[(4-methoxyphenyl)-methyl]sulfinyl}vinyl)thiole-1,1-dione; 3-((1E)-2-{[(2,4-dichlorophenyl)methyl]-sulfinyl}vinyl)thiole-1,1-dione; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(2-furyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2-furyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(2-furyl)ethene; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-chlorophenyl)-methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-iodophenyl)methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-methylphenyl)methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-trifluoromethylphenyl)methyl]sulfinyl}-2-(3-furyl)-ethene; (1E)-1-{[(2,4-dichlorophenyl)methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(3,4-dichlorophenyl)-methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-cyanophenyl)methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-nitrophenyl)methyl]sulfinyl}-2-(3-furyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(1,3-thiazol-2-yl)-ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-pyrrol-2-ylethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-pyrrol-2-ylethene; (1E)-1-{[(4-chlorophenyl)-methyl]sulfinyl}-2-(5-nitro(3-thienyl))ethene; (1E)-1-{[(4-iodophenyl)methyl]sulfinyl}-2-(5-nitro(3-thienyl))ethene; (1E)-1-{[(2,4-dichlorophenyl)methyl]sulfinyl}-2-(5-nitro(3-thienyl))ethene; (1E)-1-{[(4-methoxyphenyl)methyl]sulfinyl}-2-(5-nitro(3-thienyl))ethene; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-naphthylethene; (1E)-1-{[(4-fluorophenyl)methyl]sulfinyl}-2-(2-naphthyl)ethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-naphthylethene; (1E)-1-{[(4-chlorophenyl)methyl]sulfinyl}-2-(2-naphthyl)ethene; (1E)-1-{[(4-bromophenyl)methyl]sulfinyl}-2-naphthylethene; (1E)-1-{[(4-bromophenyl)methyl]-sulfinyl}-2-(2-naphthyl)ethene; (1E)-2-(9-anthryl)-1-{[(4-fluorophenyl)-methyl ]sulfinyl}ethene; (1E)-2-(9-anthryl)-1-{[(4-chlorophenyl)methyl]sulfinyl}ethene; (1E)-2-(9-anthryl)-1-{[(4-bromophenyl)methyl]sulfinyl}ethene; and salts thereof.

### Claim 26 (depends on 1)

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 27 (depends on 9)

A conjugate of the Formula, IC-L-Ab;
wherein:
IC is a compound according to claim 9 or a pharmaceutically acceptable salt thereof;
Ab is an antibody; and
-L- is a single covalent bond or a linking group covalently linking said compound to said antibody.

### Claim 28 (depends on 27)

A conjugate according to claim 27 wherein said antibody Ab is a monoclonal antibody or a monospecific polyclonal antibody.

### Claim 29 (depends on 28)

A conjugate according to claim 28 wherein said antibody Ab is a tumor-specific antibody.

### Claim 30 (depends on 27)

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one conjugate according to claim 27.

### Claim 31 (depends on 9)

A method of treating an individual for breast cancer, prostate cancer, lung cancer or colorectal cancer comprising administering to said individual in need of such treatment an effective amount of a compound according to claim 9, or a pharmaceutically acceptable salt thereof.

### Claim 32 (depends on 9)

A method of treating an individual for a cancer selected from the group consisting of breast, prostate, lung, and colorectal cancers, comprising administering to said individual an effective amount of a compound according to claim 9, or a pharmaceutically acceptable salt thereof, and administering an effective amount of therapeutic ionizing radiation to the individual.

### Claim 33 (depends on 9)

A method of inducing apoptosis of tumor cells in an individual afflicted with breast cancer, prostate cancer, lung cancer or colorectal cancer comprising administering to said individual an effective amount of a compound according to claim 9, or a pharmaceutically acceptable salt thereof.

### Claim 34 (depends on 27)

A method of treating an individual afflicted with breast cancer, prostate cancer, lung cancer or colorectal cancer, comprising administering to said individual an effective amount of at least one conjugate according to claim 27.

### Claim 35 (depends on 1, 3)

A process for preparing a compound according to claim 3 comprising:
(a) reacting a compound of Formula II′:
wherein A1, n, R1, Ra and x are defined as in claim 1
with a compound of Formula III′:
wherein B1, Rb and y are defined as in claim 1; and
(b) isolating a compound of claim 3 from the reaction products.

### Claim 36 (depends on 35)

A process according to claim 35 wherein the compound of Formula II′ is prepared by:
(a) reacting a compound of Formula IIA′:
with an oxidizing agent capable of oxidizing a sulfide to a sulfoxide; and
(b) isolating a compound of Formula II′ from the reaction products.

### Claim 37 (depends on 36)

A process according to claim 36 wherein the compound of Formula IIA′0 is prepared by:
(a) reacting a compound of Formula IIB′:
wherein:
L is a leaving group;
with mercaptoacetic acid; and
(b) isolating a compound of Formula IIA′ from the reaction products.

### Claim 38 (depends on 1, 2)

A process for preparing a compound according to claim 2 comprising:
(a) reacting a compound of Formula IV′:
wherein A1, B1, n, R1, Ra, Rb, x and y are defined as in claim 1;
with an oxidizing agent capable of oxidizing a sulfide to a sulfoxide; and
(b) isolating a compound of claim 2 from the reaction products.

### Claim 39 (depends on 38)

A process according to claim 38 wherein the compound of Formula IV′ is prepared by:
(a) reacting a compound of Formula IVA′:
wherein Q+ is a counterion selected from the group consisting of alkali metals, alkaline earth metals and transition metals;
with a compound of Formula IVB′:
(b) isolating a compound of Formula IV′ from the reaction products.

### Claim 40 (depends on 1)

An isolated optical isomer of a compound according to claim 1, or a salt thereof.