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

Assignee: Astellas Pharma Inc
•
Filing: 1978-05-15
•
Granted: 1980-04-08
•
Expires: 1998-05-15
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Abstract

Abstract <IMAGE> 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 <IMAGE> +TR <IMAGE> (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.

Inventors

  • 👤 Masuo Murakami
  • 👤 Kozo Takahashi
  • 👤 Yasufumi Hirata
  • 👤 Mutsuo Takashima
  • 👤 Sumio Iwanami
  • 👤 Osamu Hasegawa
  • 👤 Yoshihisa Nozaki
  • 👤 Shiro Tachikawa
  • 👤 Masaaki Takeda
  • 👤 Shinji Usuda

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 22:08
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/53; C07D207/00; C07D207/02; C07D207/04; C07D207/08; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/14; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/26; C07D217/00; C07D217/12; C07D217/14; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/52

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 16 words
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.
Claim 2
Dependent Claim 16 words
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.
Claim 3
Dependent Claim 6 words
N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-diethylamino-2-methoxybenzamide as claimed in claim 1.
Claim 4
Dependent Claim 6 words
N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-dimethylamino-2-ethoxy-benzamide as claimed in claim 1.
Claim 5
Dependent Claim 6 words
N-(1-benzyl-3-pyrrolidinyl)-5-chloro-4-(N-ethyl-N-methylamino)-2-methoxybenzamide as claimed in claim 1.
Claim 6
Dependent Claim 6 words
N-[1-(4-fluorobenzyl)-3-pyrrolidinyl]-5-chloro-4-dimethylamino-2-methoxybenzamide as claimed in claim 1.
Claim 7
Dependent Claim 6 words
N-[1-(4-chlorobenzyl)-3-pyrrolidinyl]-5-chloro-4-dimethylamino-2-methoxybenzamide as claimed in claim 1.
Claim 8
Dependent Claim 6 words
N-(1-benzyl-3-pyrrolidinyl)-5-chloro-2-methoxy-4-methylaminobenzamide as claimed in claim 1.

References Cited (Backward Citations)

US3577440A Cited
US3975402A Cited
US3900481A Cited
US4158060A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-04-08 1983-10-08 1984-04-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-04-08 1987-10-08 1988-04-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-04-08 1991-10-08 1992-04-08 $7700.00 Window Closed / Lapsed

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