US 6,639,107 B1Granted

Cyclopentyl sulfonamide derivatives

AssigneeEli Lilly and Company

InventorsJames Abraham Aikins, Edward C R Smith, Timothy Alan Shepherd, Dennis Michael Zimmerman

Life of this patent

Estimating the term…

Abstract

The present invention provides certain cyclopentyl sulfonamide derivatives of formula (I): useful for potentiating glutamate receptor function in a mammal. It also relates to novel cyclopentyl sulfonamide derivatives, to processes for their preparation and to pharmaceutical compositions containing them.

Claims29

Dependent claims

A compound of the formula:

wherein
R1, R2, and R3 each independently represent hydrogen, halogen, CF3, OCF3, CN, NO2, NH2, (1-6C)alkyl, (1-6C)alkoxy, —(CH2)nNHSO2R5, —(CH2)nNHC(═O)R5, —SO2R5, —C(═O)R6, —CH═CHCO2R7, heterocycle, or phenyl which is unsubstituted or substituted by one, two, or three substituents selected from the group consisting of halogen, CF3, OCF3, CN, NO2, NH2, (1-6C)alkyl, (1-6C)alkoxy, —(CH2)nNHSO2R5, —(CH2)nNHC(═O) R5, —SO2R5, —C(═O)R6, —C(═O)NR10R11, —SO2NR10R11, or —CH═CHCO2R7;
R4 represents (1-6C)alkyl, (2-6C)alkenyl, or NR8R9;
R5 represents (1-6C)alkyl, CF3, or phenyl which is unsubstituted or substituted by one, two, or three substituents selected from the group consisting of halogen, CF3, CN, NO2, NH2, (1-6C)alkyl, or (1-6C)alkoxy;
R6 represents (1-4C)alkyl or phenyl;
R7 represents hydrogen or (1-4C)alkyl;
R8 and R9 each independently represent hydrogen or (1-4C)alkyl;
R10 and R11 each independently represent hydrogen or (1-4C)alkyl;
and
n is 0, 1, 2, 3, or 4;
or a pharmaceutically acceptable salt thereof.

8 more elements

A compound which is selected from the group consisting of:

(+,−) trans-propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide;
(+,−) trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide;
(+,−) trans propane-2-sulfonic acid (2-biphenyl-4-yl-cyclopentyl)-amide;
(+,−) trans propane-2-sulfonic acid [2-(4′-cyano-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) trans propane-2-sulfonic acid {2-[4′-(2-methanesulfonylamino-ethyl)-biphenyl-4-yl]-cyclopentyl}-amide;
(+,−) trans propane-2-sulfonic acid [2-(3′-methanesulfonylamino-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) trans propane-2-sulfonic acid [2-(2′,4′-difluoro-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) trans propane-2-sulfonic acid [2-(4′-cyanomethyl-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) trans propane-2-sulfonic acid {2-[4′-(2-amino-ethyl)-biphenyl-4-yl}-cyclopentyl}-amide;
(+,−) trans N-(2-{4′-[2-(Propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl)-ethyl)-acetamide;
(+,−) trans 2,2,2-Trifluoro-N-(2-{4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-ethyl)-acetamide;
(+) trans propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide;
(−) trans propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide;
(+) trans propane-2-sulfonic acid [2-(4′-cyano-biphenyl-4-yl)-cyclopentyl]-amide;
(−) trans propane-2-sulfonic acid [2-(4′-cyano-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) cis-propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide;
(+,−) cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide;
(+,−) cis propane-2-sulfonic acid [2-(4′-cyano-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) cis propane-2-sulfonic acid {2-[4′-(2-methanesulfonylamino-ethyl)-biphenyl-4-yl]-cyclopentyl)-amide;
(R,R)-propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide;
(S,S)-propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide;
(+,−) cis propane-2-sulfonic acid (2-(4-nitro-phenyl)-cyclopentyl]-amide;
(+,−) cis propane-2-sulfonic acid [2-(4-amino-phenyl)-cyclopentyl]-amide;
(+,−) cis N-{4-[2-(Propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−) cis propane-2-sulfonic acid [2-(4-methanesulfonylamino-phenyl)-cyclopentyl]-amide;
(+,−) cis propane-2-sulfonic acid [2-(4-tert-butyl-phenyl)-cyclopentyl]-amide;
(+,−) trans propane-2-sulfonic acid [2-(4-tert-butyl-phenyl)-cyclopentyl]-amide;
(+,−) cis propane-2-sulfonic acid [2-(3′-methanesulfonylamino-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) cis-propane-2-sulfonic acid (2-p-tolyl-cyclopentyl)-amide;
(+,−) trans-3-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-acrylic acid ethyl ester;
(+,−) cis-propane-2-sulfonic acid (2-p-bromophenyl-cyclopentyl)-amide;
(+,−) cis-propane-2-sulfonic acid (2-p-chlorophenyl-cyclopentyl)-amide;
(+,−) cis-propane-2-sulfonic acid (2-(2,4-difluorophenyl)-cyclopentyl)-amide;
(1S,2S) cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide;
(1R,2R) cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide;
(1S,2S) cis-propane-2-sulfonic acid (2-(2,4-difluorophenyl)-cyclopentyl)-amide;
(1R,2R) cis-propane-2-sulfonic acid (2-(2,4-difluorophenyl)-cyclopentyl)-amide;
(+,−) cis-propane-2-sulfonic acid [2-(3-fluoro-phenyl)-cyclopentyl]-amide;
(+,−) cis-propane-2-sulfonic acid [2-(3,4-difluoro-phenyl)-cyclopentyl]-amide;
(1S,2S) cis-propane-2-sulfonic acid [2-(4-cyano-phenyl)-cyclopentyl]-amide;
(1R,2R) cis-propane-2-sulfonic acid [2-(4-cyano-phenyl)-cyclopentyl]-amide;
(+,−) cis-propane-2-sulfonic acid [2-(2′,4′-difluoro-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) cis propane-2-sulfonic acid [2-(3′,5′-difluoro-biphenyl-4-yl)-cyclopentyl]-amide
(+,−) cis propane-2-sulfonic acid [2-(4′-methoxy-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) cis propane-2-sulfonic acid [2-(3′-acetamido-biphenyl-4-yl)-cyclopentyl]-amide;
(+,−) cis propane-2-sulfonic acid [2-(4′-trifluoromethoxy-biphenyl-4-yl)-cyclopentyl]-amide;
(S,S) cis-4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-carboxylic acid methylamide;
(R,R) cis-4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-carboxylic acid methylamide;
(+,−) cis-propane-2-sulfonic acid {2-[4-(1-oxo-indan-5-yl)-phenyl]-cyclopentyl}-amide;
(+,−) cis-4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-sulfonic acid amide;
(S,S) cis-4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-sulfonic acid amide;
(R,R) cis-41-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-sulfonic acid amide;
(+,−)-cis-41-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-carboxylic acid;
(+,−) cis-4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-carboxylic acid methylamide;
(+,−) trans propane-2-sulfonic acid (2-(4-bromo-phenyl)-cyclopentyl)-amide;
(+,−) trans 4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-sulfonic acid amide;
(+,−) trans 4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-carboxylic acid;
(1R,2S) trans propane-2-sulfonic acid [2-(4-bromo-phenyl)-cyclopentyl]-amide;
(1S,2R) trans propane-2-sulfonic acid (2-(4-bromo-phenyl)-cyclopentyl]-amide;
(1R,2S) trans 4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-sulfonic acid amide;
(1S,2R) trans 4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-sulfonic acid amide;
(1R,2S) trans 4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-carboxylic acid methylamide;
(1S,2R) trans 4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-carboxylic acid methylamide;
(+,−) trans 4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-carboxylic acid methylamide;
(+,−) cis-propane-2-sulfonic acid [2-(4-fluoro-phenyl)-cyclopentyl]-amide;
(+,−) cis-propane-2-sulfonic acid (2-biphenyl-4-yl-cyclopentyl)-amide;
(+,−) cis-4-chloro-N-{4-[2-(propane-2-sulfonylamino)-cyclopentyl)-phenyl}-benzamide;
(+,−) cis-3,5-difluoro-N-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−) cis-2,4-difluoro-N-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−) cis-3-cyano-N-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−) cis-4-cyano-N-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−) cis-N-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-terephthalamic acid methyl ester;
(+,−) cis-4-nitro-N-{4-(2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−) cis-3-nitro-N-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−) cis-4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-3-carboxylic acid methyl ester;
(+,−) cis N-{4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-acetamide;
(+,−) cis N-{4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-3-yl}-acetamide;
(+,−) cis-N-{4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-3-yl}-acetamide;
(+,−) cis- N-{4′-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-acetamide;
(+,−)-cis-(4-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenylcarbamoyl}-phenyl)-carbamic acid tert-butyl ester;
(+,−)-cis-(4-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenylcarbamoyl}-phenyl)-carbamic acid tert-butyl ester;
(+,−)-cis 4-amino-N-(4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−)-cis-3-amino-N-{4-[2-(propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide;
(+,−) cis-N-[2-(phenyl)-cyclopentyl]-dimethylaminosulfonamide;
(+,−) cis- N-[2-(4-bromo-phenyl)-cyclopentyl]-dimethylaminosulfonamide;
(+,−) cis-N-[2-(3′-methanesulfonylamino-biphenyl-4-yl)-cyclopentyl]-dimethylaminosulfonamide;
and
(+,−) cis-N-[2-(4-cyano-biphenyl-4-yl)-cyclopentyl]-dimethylaminosulfonamide;
or a pharmaceutically acceptable salt thereof.

86 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/130,156Filed 14 May 2002 · us provisional application
Priority: 8 Dec 1999
Granted: 28 Oct 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 311/07
Of an acyclic saturated carbon skeleton: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other…
C07C 307/08
Diamides of sulfuric acids: having nitrogen atoms of the sulfamide groups bound to carbon atoms of rings other than six-membered aromatic rings
C07C 311/05
Having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms: to acyclic carbon atoms of hydrocarbon…
C07C 311/08
Of an acyclic saturated carbon skeleton: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a…

Family

Application60/169,684Us provisional application · filed 8 Dec 1999
US 6,639,107 B1This patent

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

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Abstract

Facts

Application

10/130,156Filed 14 May 2002 · us provisional application

Priority

8 Dec 1999

Granted

28 Oct 2003

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 311/07
Of an acyclic saturated carbon skeleton: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other…
C07C 307/08
Diamides of sulfuric acids: having nitrogen atoms of the sulfamide groups bound to carbon atoms of rings other than six-membered aromatic rings
C07C 311/05
Having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms: to acyclic carbon atoms of hydrocarbon…
C07C 311/08
Of an acyclic saturated carbon skeleton: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a…