Sulfonamide derivatives

• US 5,250,549 A
• Filed: 08/08/1991
• Issued: 10/05/1993
• Est. Priority Date: 08/20/1990
• Status: Expired due to Term

• Current Assignee: Eisai R & D Management Company Limited (Eisai Medical Research Incorporated)
• Original Assignee: Eisai Company Limited (Eisai Medical Research Incorporated)
• Inventors: Kotake, Yoshihiko, Tsukahara, Kappei, Ueda, Norihiro, Niijima, Jun, Yoshino, Hiroshi, Asada, Makoto, Watanabe, Tatsuo, Okada, Toshimi, Nagasu, Takeshi, Yoshimatsu, Kentaro, Koyanagi, Nozomu, Sugumi, Hiroyuki, Kitoh, Kyosuke, Iijima, Atsumi
• Primary Examiner(s): Ivy, C. Warren
• Assistant Examiner(s): SPIVACK, PHYLLIS G
• Application Number:
  US07/742,618
• Time in Patent Office: 789 Days
• Field of Search: 546/307, 546/22, 546/24, 514/352, 514/345, 514/348, 514/349
• US Class Current: 514/345
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• 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 311/44 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: C07D 213/74 Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
• 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 213/82 in position 3
• CPC Class Codes: C07D 239/42 One nitrogen atom nitro radicals C07D239/30
• CPC Class Codes: C07D 239/48 Two nitrogen atoms
• CPC Class Codes: C07D 239/50 Three nitrogen atoms
• CPC Class Codes: C07D 307/68 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 333/38 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07F 9/58 Pyridine rings
• CPC Class Codes: C07H 15/203 Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
• CPC Class Codes: C07H 15/26 Acyclic or carbocyclic radicals, substituted by hetero rings

Abstract

Sulfonamide derivatives of the general formula (I): ##STR1## wherein preferably R¹ represents a lower alkoxy group, R², R³, R⁴, R⁵, R⁶ and R⁷ are as defined in the specification, A and B may be the same or different from each other and each represents ═N-- or ═CH--, E represents an aromatic 6-membered cyclic group, which may have 1 or 2 nitrogen atoms in the ring, and may be substituted with 1 to 3 substituents which may be the same or different from one another with the proviso that a combination of R¹ which is a hydrogen atom, lower alkyl group, nitro group or amino group which may be protected, R² and R³ which are each a hydrogen atom, A and B which are each ═CH-- and E which is a phenyl group which may be substituted with 1 to 3 substituents G which may be the same or different from one another is excluded, or pharmacologically acceptance salts of them.

Claims

1. Sulfonamide derivatives of general formula (1) or pharmacologically acceptable salts thereof:

##STR143## wherein;

R¹ represents a hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, hydroxyl group, nitro group, phenoxy group, cyano group, acetyl group or amino group, R² and R³ may be the same or different from each other and each represent a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group, R⁴ and R⁷ may be the same or different from each other and each represent a hydrogen atom or lower alkyl group, R⁵ and R⁶ may be the same or different from each other and each represents a hydrogen atom, halogen atom, lower alkoxy group, amino group or an amino group substituted with a lower alkyl or a phenyl group, and D represents H or NO.

2. Sulfonamide derivatives or pharmacologically acceptable salts of them according to claim 1, wherein OD is a hydroxyl group or a protected hydroxyl group.

3. Sulfonamide derivatives or pharmacologically acceptable salts thereof according to claim 1, wherein R¹ represents a lower alkoxy group.

4. Sulfonamide derivatives or pharmacologically acceptable salts of them according to claim 3, wherein OD is a hydroxyl group or a protected hydroxyl group.

5. Sulfonamide derivatives or pharmacologically acceptable salts thereof according to claim 1, wherein the compound is selected from among the following sulfonamide derivatives:

4-methoxy-N-[2-[(4-methoxyphenyl)amino]-3-pyridyl]benzenesulfonamide or

N-[2-[(4-hydroxyphenyl)amino]-3-pyridyl]-4-methoxybenzenesulfonamide.

6. A pharmacological composition which comprises a pharmacologically effective amount of the derivative as defined in claim 1 and a pharmacologically acceptable carrier.

7. Sulfonamide derivatives of general formula (1) or pharmacological acceptable salts thereof ##STR144## wherein:

R¹ represents a hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, hydroxyl group, nitro group, phenoxy group, cyano group, acetyl group, or amino group, R² and R³ may be the same or different from each other and each represent a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group, R⁴ and R⁷ may be the same or different from each other and each represent a hydrogen atom or lower alkyl group, R⁵ and R⁶ may be the same or different from each other and each represents a hydrogen atom, halogen atom, lower alkoxy group, amino group or an amino group substituted with a lower alkyl or a phenyl group, A is ═

CH--, B is ═

N-- and E is phenyl optionally substituted by --OD, D representing H, NO, PO(OH)₂ or a lower alkyl group.

8. Sulfonamide derivatives or pharmacologically acceptable salts thereof according to claim 7, wherein the compound is selected from among the following sulfonamide derivatives:

(1) N-(2-anilino-3-pyridyl)-p-toluenesulfonamide,

(2) N-(2-anilino-3-pyridyl)-4-ethylbenzenesulfonamide,

(3) N-(2-anilino-3-pyridyl)-4-methoxybenzenesulfonamide, and

(4) 4-[[3-(4-methoxybenzenesulfonamide)-2-pyridyl]amino]-phenyl dihydrogenphosphate.

9. Sulfonamide derivatives of the general formula (1) or pharmacologically acceptable salts thereof:

##STR145## wherein;

R¹ represents a hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, hydroxyl group, nitro group, phenoxy group, cyano group, acetyl group, or amino group, R² and R³ may be the same or different from each other and each represent a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group, R⁴ and R⁷ may be the same or different from each other and each represents a hydrogen atom or a lower alkyl group, R⁵ and R⁶ may be the same or different from each other and each represents a hydrogen atom, halogen atom, lower alkoxy group, amino group or an amino group substituted with a lower alkyl or a phenyl group, A is ═

CH--, B is ═

N-- and E is a phenyl group or a phenyl group having from 1 to 3 substituents, said substituents being the same or different from one another and selected from the group consisting of a halogen atom, lower alkyl group, lower alkoxy group, hydroxyl group, protected hydroxyl group, carboxyl group, esterified carboxyl group, amidated carboxyl group, lower alkylthio group and phenoxy group.