N-1-Benzyl-3-pyrrolidinyl-4-dimethylamino benzamide derivatives

• US 4,197,243 A
• Filed: 05/15/1978
• Issued: 04/08/1980
• Est. Priority Date: 04/02/1975
• Status: Expired due to Term

• Current Assignee: Yamanouchi Pharmaceutical Co., Ltd. (Astellas Pharma Incorporated)
• Original Assignee: Yamanouchi Pharmaceutical Co., Ltd. (Astellas Pharma Incorporated)
• Inventors: Takahashi, Kozo, Murakami, Masuo, Takeda, Masaaki, Tachikawa, Shiro, Hasegawa, Osamu, Nozaki, Yoshihisa, Usuda, Shinji, Hirata, Yasufumi, Iwanami, Sumio, Takashima, Mutsuo
• Primary Examiner(s): Daus, Donald G.
• Assistant Examiner(s): Wheeler, David E.
• Application Number:
  US05/906,079
• Time in Patent Office: 694 Days
• Field of Search: 260/326.47
• US Class Current: 548/557
• CPC Class Codes: C07D 207/08 with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 209/14 Radicals substituted by nitrogen atoms, not forming part of a nitro radical
• CPC Class Codes: C07D 211/26 with hydrocarbon radicals, substituted by nitrogen atoms
• CPC Class Codes: C07D 213/53 Nitrogen atoms
• CPC Class Codes: C07D 217/14 other than aralkyl radicals
• CPC Class Codes: C07D 307/52 Radicals substituted by nitrogen atoms not forming part of a nitro radical

Abstract

##STR1## wherein R represents a hydrogen atom or a lower alkyl group; X represents a lower alkoxy group; Y represents a hydrogen atom, an amino group, or mono- or di-lower alkylamino group; Z represents a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a sulfamoyl group, or a lower alkylsulfamoyl group; said Y and Z may combine to form --N═N--NH--; W represents a group shown by the formula ##STR2## (wherein A represents a phenyl group, a cyclohexyl group, a furyl group, or a pyridyl group; R₁, R₂, and R₄, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a phenyl group; R₃ represents a lower alkyl group, a phenyl lower alkyl group, or a di-lower alkylamino lower alkyl group; R₅, R₆, and R₇, which may be the same or different, each represents a hydrogen atom, a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, or a trifluoromethyl group; R₈ represents a lower alkyl group; and n represents 1 or 2), a 1-ethyl-5-phenyl-2-pyrrolidinylmethyl group, a 1-ethyl-2-isoindolinylmethyl group, a 2-ethyl-1,2,3,4-tetrahydro-4-isoquinolyl group, a 2-(2-phenylpyrrolidino)ethyl group, a 2-(2-isoindolinyl)ethyl group, or a 2-(1,2,3,4-tetrahydro-2-isoquinolyl)ethyl group and the pharmaceutically acceptable nontoxic salts thereof.

The compounds of this invention are strong central nervous system depressants, in particular strong antipsychotics.

Claims

1. A benzamide compound selected from the group consisting of N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-diethylamino-2-methoxybenzamide, N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-dimethylamino-2-ethoxy-benzamide, N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-(N-ethyl-N-methylamino)-2-methoxybenzamide, N-[1-(4-fluorobenzyl)-3-pyrrolidinyl]-5-chloro-4-dimethylamino-2-methoxybenzamide, N-[1-(4-chlorobenzyl)-3-pyrrolidinyl]-5-chloro-4-dimethylamino-2-methoxybenzamide, and N-(1-benzyl-3-pyrrolidinyl)-5-chloro-2-methoxy-4-methylaminobenzamide.

2. N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-diethylamino-2-methoxybenzamide as claimed in claim 1.

3. N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-dimethylamino-2-ethoxy-benzamide as claimed in claim 1.

4. N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-(N-ethyl-N-methylamino)-2-methoxybenzamide as claimed in claim 1.

5. N-[1-(4-fluorobenzyl)-3-pyrrolidinyl]-5-chloro-4-dimethylamino-2-methoxybenzamide as claimed in claim 1.

6. N-[1-(4-chlorobenzyl)-3-pyrrolidinyl]-5-chloro-4-dimethylamino-2-methoxybenzamide as claimed in claim 1.

7. N-(1-benzyl-3-pyrrolidinyl)-5-chloro-2-methoxy-4-methylaminobenzamide as claimed in claim 1.