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US4252804A Expired / Lapsed US ⏱️ 0.0 years remaining

Therapeutically useful 3,4,5-trimethoxybenzene derivatives

Assignee: Metabio-Joullie
•
Filing: 1978-01-13
•
Granted: 1981-02-24
•
Expires: 1998-01-13
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Abstract

Abstract Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO 2 , and NR 1 R 2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(α-m-chlorophenyl-benzyl)-piperazino, 4-(3,4,5-trimethoxyphenylaminocarbonyl)-piperazino, 4-(3,4,5-trimethoxyphenylaminocarbonylmethyl)-piperazino, 4-phenylpiperazino, 4-m-trifluoromethylphenyl-piperazino, 4-piperidinocarbonylmethyl-piperazino, 1,2,3,4-tetrahydroquinolyl, 1,2,3,4-tetrahydroisoquinolyl, (7-chloro-4-quinolyl)-amino, 1,2,3,4-tetrahydrobenzoxazinyl or 1,2,3,4-tetrahydro-6-chlorobenzoxazinyl group, and their pharmaceutically acceptable acid addition salts are novel and are therapeutically useful, in particular as tranquillizers, myorelaxants and anticonvulsants.

Inventors

  • 👤 Maurice Joullie
  • 👤 Gabriel Maillard
  • 👤 Lucien Lakah
  • 👤 Christian J. M. Warolin

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 13:35
CPC Classifications
C; C07; C07D; C07D261/00; C07D261/02; A; A61; A61P; A61P25/00; A61P25/08; A61P25/24; A61P25/26; C07C; C07C275/00; C07C275/28; C07C275/32; C07C275/34; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/52; C07D211/68; C07D211/70; C07D215/00; C07D215/02; C07D215/04; C07D215/06; C07D215/08; C07D215/16; C07D215/38; C07D215/42; C07D215/44; C07D217/00; C07D217/02; C07D217/06; C07D265/00; C07D265/28; C07D265/30; C07D265/34; C07D265/36; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C07D295/12; C07D295/125; C07D295/13; C07D295/14; C07D295/145; C07D295/15; C07D295/16; C07D295/18; C07D295/182; C07D295/185; C07D295/20; C07D295/205; C07D295/215; C07D295/22; C07D295/24; C07D295/26; C07D295/28; C07D295/32; C07D307/00; C07D307/02; C07D307/04; C07D307/10; C07D307/14; C07D309/00; C07D309/02; C07D309/04; C07D309/08; C07D309/14; C07C2601/00; C07C2601/06; C07C2601/08; C07C2601/12; C07C2601/14; C07C2601/18; C07C2603/00; C07C2603/56; C07C2603/58; C07C2603/70; C07C2603/74

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 81 words
A compound of the formula ##STR88## wherein m is selected from O and the numbers 1 and 2, X is selected from oxygen and an imino group of the formula NR 3 ,(wherein R 3 is selected from hydrogen benzyl, and morpholinoethyl), Y is selected from the divalent groups CO, CONH, and COO and SO 2 , and NR 1 R 2 is selected from the group consisting of morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, and thiamorpholino, and their pharmaceutically-acceptable acid addition salts.
Claim 2
Dependent Claim 81 words
A compound of the formula ##STR88## wherein m is selected from O and the numbers 1 and 2, X is selected from oxygen and an imino group of the formula NR 3 ,(wherein R 3 is selected from hydrogen benzyl, and morpholinoethyl), Y is selected from the divalent groups CO, CONH, and COO and SO 2 , and NR 1 R 2 is selected from the group consisting of morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, and thiamorpholino, and their pharmaceutically-acceptable acid addition salts.
Claim 3
Dependent Claim 31 words
A compound according to claim 1 which is of the formula ##STR89## (wherein X and NR 1 R 2 are as defined in claim 1) and its pharmaceutically-acceptable acid addition salts.
Claim 4
Dependent Claim 32 words
A compound according to claim 1 which is of the formula ##STR90## (wherein Y, m and NR 1 R 2 are as defined in claim 1) and its pharmaceutically-acceptable acid addition salts.
Claim 5
Dependent Claim 16 words
A compound according to claim 1 wherein NR 1 R 2 represents a morpholino or 2,6-dimethylmorpholino.
Claim 6
Dependent Claim 13 words
A compound according to claim 1 which is selected from 4-[N-(3,4,5-trimethoxyphenyl)-carbamoyl]-morpholine and 4-(3,4,5-trimethoxyphenoxycarbonyl)-morpholine.
Claim 7
Dependent Claim 7 words
4-(3,4,5-Trimethoxyphenoxycarbonyl)-morpholine, and its pharmaceutically-acceptable acid addition salts.
Claim 8
Dependent Claim 7 words
4-(3,4,5-Trimethoxyphenoxycarbonyl)-morpholine, and its pharmaceutically-acceptable acid addition salts.
Claim 9
Dependent Claim 7 words
4-[N-(3,4,5-trimethoxyphenyl)-carbamoyl]-morpholine, and its pharmaceutically-acceptable acid addition salts.
Claim 10
Dependent Claim 7 words
4-[N-(3,4,5-trimethoxyphenyl)-carbamoyl]-morpholine, and its pharmaceutically-acceptable acid addition salts.
Claim 11
Dependent Claim 39 words
A pharmaceutical composition, useful for its tranquilizing, muscle relaxing and sedative effects, which comprises a pharmaceutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid-addition salt thereof together with a pharmaceutically acceptable carrier or diluent.
Claim 12
Dependent Claim 16 words
A pharmaceutical composition according to claim 7 which contains a compound selected from 4-[N-(3,4,5-trimethoxyphenyl)-carbamoyl]-morpholine and 4-(3,4,5-trimethoxyphenoxycarbonyl)-morpholine.
Claim 13
Dependent Claim 35 words
A method for treating a human patient which comprises administering to said patient for its tranquilizing, muscle relaxing and sedative effects, a therapeutically-effective amount of a compound of claim 1 or a pharmaceutically-acceptable acid-addition-salt thereof.
Claim 14
Dependent Claim 17 words
A method according to claim 10 wherein there is administered a compound selected from 4-[N-(3,4,5-trimethoxyphenyl)-carbamoyl]-morpholine and 4-(3,4,5-trimethoxyphenoxycarbonyl)-morpholine.

References Cited (Backward Citations)

US2870145A Cited
US2882273A Cited
US2870146A Cited
GB872350A Cited
GB912788A Cited
US3234276A Cited
US3562262A Cited
US3729470A Cited
US3755317A Cited
GB1346029A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-02-24 1984-08-25 1985-02-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-02-24 1988-08-25 1989-02-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-02-24 1992-08-25 1993-02-24 $7700.00 Window Closed / Lapsed

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