Sulfonamide derivatives and drugs containing the same as the active ingredient

• US 6,403,607 B1
• Filed: 10/02/2000
• Issued: 06/11/2002
• Est. Priority Date: 03/30/1998
• Status: Expired due to Fees

• Current Assignee: Hiroyoshi Hidaka
• Original Assignee: Hiroyoshi Hidaka
• Inventors: Nakano, Hiroyuki, Hidaka, Hiroyoshi, Watanabe, Naofumi, Umezawa, Isao, Sasaki, Tomomitsu, Yokota, Shizumasa, Yajima, Yumi, Inoue, Tsutomu, Nakamura, Hiroshi
• Primary Examiner(s): Rotman, Alan L.
• Assistant Examiner(s): ROBINSON, BINTA M
• Application Number:
  US09/647,533
• Time in Patent Office: 617 Days
• Field of Search: 564/80, 564/81, 546/294, 546/141, 546/60, 546/167, 546/142, 544/128, 549/67, 549/429, 548/251, 514/187, 514/461, 514/231.2, 514/231.5, 514/309
• US Class Current: 514/309
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: 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
• CPC Class Codes: C07C 311/21 having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 311/29 having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 323/49 to sulfur atoms
• CPC Class Codes: C07D 213/74 Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
• CPC Class Codes: C07D 213/75 Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
• CPC Class Codes: C07D 213/76 to which a second hetero atom is attached nitro radicals C07D213/61
• CPC Class Codes: C07D 213/81 Amides; Imides
• CPC Class Codes: C07D 215/40 attached in position 8
• CPC Class Codes: C07D 217/02 with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
• CPC Class Codes: C07D 243/08 not condensed with other rings
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links

Abstract

The present invention discloses a sulfonamide derivative represented by the following formula (1):

[wherein A represents a nitrogen atom, —CH═, etc.; Z represents an oxygen atom, etc.; Ar¹ represents an aryl group, etc.; Ar² represents an alkyl group, etc.; R^a represents a hydrogen atom, etc.; R^b represents a hydrogen atom, etc.; and R^c represents an alkyl group, etc.], or a salt thereof; and drugs containing the derivative or a salt thereof as an active ingredient.

This compound exhibits radical scavenging action, gastric mucous secretion augmenting action, and anti-HP action, and thus is effective as a peptic ulcer therapeutic agent.

Claims

1. A sulfonamide compound represented by the following formula (1):

wherein Z represents an imino group, —

N(R²)—

(CH²)_n—

, —

N(R²)—

(CH²)_n—

N(R³)—

, —

N(R²)—

(CH²)_n—

O—

, —

N(R²)—

(CH²)_n—

S—

, —

N(R²)—

(CH²)_n—

NHSO₂—

, —

N(R²)—

CH₂CH═

CH—

, —

O(CH₂)—

N(R³)—

, or —

N(R²)—

(CH²)_n—

O—

CH₂—

;

Ar¹ represents an aromatic hydrocarbon group, a saturated heterocyclic group or an unsaturated heterocyclic group selected from the group consisting of pyridyl, thienyl, furyl, quinolyl, oxazolyl, thiazolyl, thiadiazolyl, and tetrazolyl.

Ar² represents a phenyl group, an alkyl group, a naphthyl group, a quinolyl group, an isoquinolyl group, a thienyl group, or a pyridyl group, which optionally has one through three substituents selected from among a halogen atom, an alkyl group, an alkoxy group, an acetamido group, and a nitro group;

R^a represents a hydrogen atom, a morpholinoyl group, an alkoxy group, or an aminoalkoxy group;

R^b represents a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group;

R^c represents a hydrogen atom, or an alkyl group or a halogenobenzenesulfonyl group, which optionally has a substituent;

R¹ represents a hydrogen atom, or R¹ and R² together form a trimethylene group;

R² represents a hydrogen atom, an alkyl group, a dialkylaminoalkyl group, a benzyl group, a halogenophenyl group, or a halogenobenzenesulfonyl group, R² and R¹ together form a trimethylene group, or R² and R³ together for an ethanedioyl group or an alkylene group;

R³ represents a hydrogen atom, an alkyl group, a hydroxyoxalyl group, an alkanoyl group, a sulfonyl group, an alkoxycarbonyl group, or a halogenobenzenesulfonyl group, or R³ and R² together form an ethanedioyl group or an alkylene group;

n is a number of 2-4; and

Z is not —

N(R²)—

CH₂—

CH═

CH—

when Ar² is an isoquinolyl group, or a pharmaceutically acceptable salt thereof.

2. A sulfonamide compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R^c is an alkyl group having a substituent selected from the group consisting of an amino group, a dialkylamino group, an aminoalkoxy group, a dialkylaminoalkoxy group, a heterocyclic group, and a hydroxyl group.

3. A pharmaceutical composition comprising a sulfonamide compound as recited in claim 1 or 2 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier therefor.

4. A method for treating a patient in need of treatment for a peptic ulcer comprising administration of an effective dose of a sulfonamide compound as recited in claim 1 or 2 or a pharmaceutically acceptable salt thereof.

5. A method for treating a patient in need of treatment for a Helicobacter-Pylori infection comprising administering an effective dose of sulfonamide compound as recited in claim 1 or 2 or a pharmaceutically acceptable salt thereof.

6. A sulfonamide compound according to claim 1 of the formula N-(4-chlorobenzenesulfonyl)-N-(2-dimethylaminoethyl)-N′

-[2-(4-chlorophenoxy)ethyl ]-o-phenylenediamine or a pharmaceutically acceptable salt thereof.

7. N-[2-(2-Aminoethoxy)ethyl]-N-(4-chlorobenzenesulfonyl)-N′

-[2-(4-chlorophenoxy)ethyl]-o-phenylenediamine or a pharmaceutically acceptable salt thereof.

8. N-(4-Chlorobenzenesulfonyl)-N-[2-(2-dimethylamino)ethoxyethyl]-N′

-[2-(4-chlorophenoxy)ethyl]-o-phenylenediamine or a pharmaceutically acceptable salt thereof.