US3979390A
Expired / Lapsed
US
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Butyrophenone derivatives and production thereof
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1973-03-16
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Granted: 1976-09-07
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Expires: 1993-03-16
Abstract
Abstract A process for producing butyrophenone derivatives of the formula: ##EQU1## which comprises reacting a compound of the formula: ##SPC1## With an amine of the formula H-W (wherein Ar represents a group of either one of the formulas: ##SPC2## Z is a secondary amino group and W is the residue of an amine excluding a hydrogen atom therefrom). The said butyrophenone derivatives and their salts exhibit a variety of beneficial pharmacological activities including a central and autonomic nervous system depressing activity.
Inventors
- 👤 Kikuo Sasajima
- 👤 Keiichi Ono
- 👤 Masaru Nakao
- 👤 Isamu Maruyama
- 👤 Masaharu Takayama
- 👤 Shigenari Katayama
- 👤 Junki Katsube
- 👤 Shigeho Inaba
- 👤 Hisao Yamamoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 04:55
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/10; C07D295/104; C07D295/108; A; A61; A61P; A61P25/00; A61P25/02; A61P25/04; A61P25/20; C07C; C07C45/00; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/80; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/52; C07D217/00; C07D217/02; C07D217/04; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/16
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
309 words
A process for producing butyrophenone derivatives and their acid addition salts, which comprises reacting a compound of the formula: ##SPC19## with a secondary amine of the formula: ##EQU2## wherein R 11 and R 12 are each hydrogen, C 1 -C 8 alkyl, hydroxy-substituted C 1 -C 8 alkyl, C 1 -C 4 alkoxy substituted C 1 -C 8 alkyl, di(C 1 -C 4 alkyl) amino-substituted C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl or optionally substituted aralkyl, at least one of R 11 and R 12 being an optionally substituted benzyl group, to give an intermediate compound of the formula: ##EQU3## wherein Ar is a group of either one of the formulas: ##SPC20## Z is a secondary amino group of either one of the formulas: ##SPC21## wherein R 1 is hydrogen or hydroxyl, R 2 and R 3 are each hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl and n is a integer of 0 or 1; ##SPC22## wherein R 4 is hydrogen or C 1 -C 4 alkyl, R 5 and R 6 are each hydrogen, halogen or C 1 -C 4 alkyl and the dotted line is an optional bond between the carbon atoms at the 3- and 4-positions of the piperidine ring, ##SPC23## wherein R 7 is hydrogen or C 1 -C 4 alkyl and R 8 is hydrogen, halogen, C 1 -C 4 or C 1 -C 4 alkoxy, ##SPC24## wherein R 9 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl and m is an integer of 0, 1 or 2, and ##SPC25## wherein R 10 is hydrogen, halogen, hydroxyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; and thereafter hydrogenating said intermediate compound to give the corresponding compound wherein the optionally substituted benzyl group is eliminated.
Claim 2
Dependent Claim
309 words
A process for producing butyrophenone derivatives and their acid addition salts, which comprises reacting a compound of the formula: ##SPC19## with a secondary amine of the formula: ##EQU2## wherein R 11 and R 12 are each hydrogen, C 1 -C 8 alkyl, hydroxy-substituted C 1 -C 8 alkyl, C 1 -C 4 alkoxy substituted C 1 -C 8 alkyl, di(C 1 -C 4 alkyl) amino-substituted C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl or optionally substituted aralkyl, at least one of R 11 and R 12 being an optionally substituted benzyl group, to give an intermediate compound of the formula: ##EQU3## wherein Ar is a group of either one of the formulas: ##SPC20## Z is a secondary amino group of either one of the formulas: ##SPC21## wherein R 1 is hydrogen or hydroxyl, R 2 and R 3 are each hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl and n is a integer of 0 or 1; ##SPC22## wherein R 4 is hydrogen or C 1 -C 4 alkyl, R 5 and R 6 are each hydrogen, halogen or C 1 -C 4 alkyl and the dotted line is an optional bond between the carbon atoms at the 3- and 4-positions of the piperidine ring, ##SPC23## wherein R 7 is hydrogen or C 1 -C 4 alkyl and R 8 is hydrogen, halogen, C 1 -C 4 or C 1 -C 4 alkoxy, ##SPC24## wherein R 9 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl and m is an integer of 0, 1 or 2, and ##SPC25## wherein R 10 is hydrogen, halogen, hydroxyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; and thereafter hydrogenating said intermediate compound to give the corresponding compound wherein the optionally substituted benzyl group is eliminated.
Claim 3
Dependent Claim
31 words
The process according to claim 1, wherein said optionally substituted benzyl group is selected from the group consisting of unsubstituted benzyl or substituted benzyl substituted with methoxy, methyl, fluoro or chloro.
Claim 4
Dependent Claim
26 words
The process according to claim 2, wherein said optionally substituted benzyl group is selected from the group consisting of benzyl, p-methoxybenzyl, p-methylbenzyl, o,p-dimethylbenzyl, p-fluorobenzyl, p-chlorobenzyl, α-ethylbenzyl.
Claim 5
Dependent Claim
42 words
The process according to claim 1, wherein the optionally substituted aralkyl groups are selected from the group consisting of phenethyl, benzhydryl, naphthalenemethyl, unsubstituted phenethyl, substituted phenethyl substituted with hydroxy, unsubstituted benzyl and substituted benzyl substituted with methoxy, methyl, ethyl, fluoro or chloro.
Claim 6
Dependent Claim
31 words
The process according to claim 4, wherein the optionally substituted aralkyl groups are selected from the group consisting of benzyl, p-methoxybenzyl, methylbenzyl, o,p-dimethylbenzyl, p-fluorobenzyl, p-chlorobenzyl, α-ethylbenzyl, phenethyl, 3,4-dihydroxyphenethyl, benzhydryl, and 1-naphthalenemethyl.
Claim 7
Dependent Claim
24 words
The process according to claim 4, wherein said nonpolar solvent is selected from the group consisting of benzene, toluene, xylene, dioxane and carbon tetrachloride.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-09-07 | 1980-03-08 | 1980-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-07 | 1984-03-08 | 1984-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-07 | 1988-03-08 | 1988-09-07 | $7700.00 | Window Closed / Lapsed |