US 2003/0232802 A1Published application

Aryl and heteroaryl sulfonates

AssigneeBayer Aktiengesellschaft

InventorsMarkus Heil, Heinrich Meier, Paul Naab, Arnd Voerste, Jean-Marie-Viktor de Vry, Dirk Denzer, Frank Mauler, Klemens Lustig, Volker Hinz, Swen Allerheiligen

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Abstract

The invention relates to novel aryl and heteroaryl sulfonates of formula (Ia) and to methods for producing them and to novel aryl and heteroaryl sulfonates of formula (I) for treating and/or preventing diseases, especially for treating pain and neurodegenerative diseases, A representing (C6-C10)-aryl or 5-10-membered heteroaryl, D representing (C6-C10)-arylene or 5-10-membered heteroarylene, R1 representing (C4-C8)-alkyl, (C2-C8)-alkyl, the carbon chain being interrupted by one or two heteroatoms or groups chosen from the following group: —O—, —S—, —SO—and —SO2—, (C2-C8)-alkenyl or (C2-C8)-alkinyl, in formula (Ia); and R1 representing (C3-C8)-alkyl, (C2-C8)-alkyl, the carbon chain being interrupted by one or two heteroatoms or groups chosen from the following group: —O—, —S—,—SO—and —SO2—, (C2-C8)-alkenyl or (C2-C8)-alkinyl. A—D—O—SO2—R1 (Ia) A—D—O—SO2—R1 (I)

Claims10

Dependent claims

A compound of the formula (I),

A-D-O—SO2—R1 (I)
in which
A
represents (C6-C10)-aryl or 5- to 10-membered heteroaryl
where adjacent ring atoms in aryl and heteroaryl are, where appropriate, connected by a saturated or partially unsaturated bridge comprising 3 to 7 bridge atoms selected from the group of carbon, nitrogen, oxygen and sulfur, and
where aryl, heteroaryl and the bridge are optionally substituted one or more times by radicals selected from the group of (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkinyl, (C1-C8)-alkoxy, (C1-C8)-alkanoyl, (C3-C8)-cyclolkyl, halogen, nitro, cyano, hydroxyl, trifluoromethoxy, —CO2R2, —CONR3R4, —SO2NR5R6, —NR7COR8, —NR9SO2R10 and —NR11R12, where (C1-C8)-alkyl in turn is optionally substituted by halogen, cyano, hydroxyl or —NR13R14,
in which
R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13 and R14 are identical or different and denote hydrogen, optionally hydroxyl- or (C1-C4)-alkoxy-substituted (C1-C8)-alkyl or (C3-C8)-cycloalkyl,
D represents (C6-C10)-arylene or 5- to 10-membered heteroarylene where arylene and heteroarylene are optionally substituted one or more times by radicals selected from the group of (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkinyl, (C1-C8)-alkoxy, (C1-C8)-alkanoyl, (C3-C8)-cycloalkyl, halogen, nitro, cyano, hydroxyl, trifluoromethyl, trifluoromethoxy and —CO2R15,
in which
R15 denotes hydrogen, (C1-C8)-alkyl or (C3-C8)-cycloalkyl, and
R1
represents (C4-C8)-alkyl,
represents (C2-C8)-alkyl where the carbon chain is interrupted by one or two heteroatoms or groups selected from the group of —O—, —S—, —SO— and —SO2—,
represents (C2-C8)-alkenyl, or
represents (C2-C8)-alkinyl,
where alkyl, alkenyl and alkinyl are optionally substituted one or more times by halogen and/or cyano,
and the salts, hydrates and/or solvates thereof,
with the exception of
compounds of the general formula (I), in which D is phenylene and R1 is 1,1,2,2,3,3,4,4,4-nonafluorobutyl, and
with the exception of
[1,1′-biphenyl]-4-yl 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-1-octanesulfonate and
[1,1′-biphenyl]-2-yl 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-1-octanesulfonate.

20 more elements

A compound of the formula (I)

A-D-O—SO2—R1 (I)
in which
A
represents (C6-C10)-aryl or 5- to 10-membered heteroaryl,
where adjacent ring atoms in aryl and heteroaryl are, where appropriate, connected by a saturated or partially unsaturated bridge comprising 3 to 7 bridge atoms selected from the group of carbon, nitrogen, oxygen and sulfur, and
where aryl, heteroaryl and the bridge are optionally substituted one or more times by radicals selected from the group of (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkinyl, (C1-C8)-alkoxy, (C1-C8)-alkanoyl,
(C3-C8)-cycloalkyl, halogen, nitro, cyano, hydroxyl, trifluoromethoxy, —CO2R2, —CONR3R4, —SO2NR5R6, —NR7COR8, —NR9SO2R10 and —NR11R12, where (C1-C8)-alkyl in turn is optionally substituted by halogen, cyano, hydroxyl or —NR13R14,
in which
R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13 and R14 are identical or different and denote hydrogen, optionally hydroxyl- or (C1-C4)-alkoxy-substituted (C1-C8)-alkyl or (C3-C8)-cycloalkyl,
D represents (C6-C10)-arylene or 5- to 10-membered heteroarylene, where arylene and heteroarylene are optionally substituted one or more times by radicals selected from the group of (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkinyl, (C1-C8)-alkoxy, (C1-C8)-alkanoyl, (C3-C8)-cycloalkyl, halogen, nitro, cyano, hydroxyl, trifluoromethyl, trifluoromethoxy and —CO2R15,
in which
R15 denotes hydrogen, (C1-C8)-alkyl or (C3-C8)-cycloalkyl, and
R1
represents (C3-C8)-alkyl,
represents (C2-C8)-alkyl where the carbon chain is interrupted by one or two heteroatoms or groups selected from the group of —O—, —S—, —SO— and —SO2—,
represents (C2-C8)-alkenyl, or
represents (C2-C8)-alkinyl,
where alkyl, alkenyl and alkinyl are optionally substituted one or more times by halogen and/or cyano,
and the salts, hydrates and/or solvates thereof,
for the treatment and/or prophylaxis of diseases.

17 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/240,464Filed 12 May 2003
Priority: DE 10015866.830 Mar 2000
Published: 18 Dec 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification43 codes

C07D 217/16
Other than aralkyl radicals: substituted by oxygen atoms
A61P 1/08
Drugs for disorders of the alimentary tract or the digestive system: for nausea, cinetosis or vertigo; Antiemetics
A61P 11/06
Drugs for disorders of the respiratory system: antiasthmatics
A61P 13/12
Drugs for disorders of the urinary system: of the kidneys

Family

US 6,919,470 B2Related patent
US 2003/0232802 A1This patent

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

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