Patent US3907812A successfully refreshed from Google Patents.
US3907812A
Expired / Lapsed
US
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Butyrophenone derivatives
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1973-02-02
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Granted: 1975-09-23
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Expires: 1993-02-02
Abstract
Abstract A novel process for preparing central nervous system active butyrophenone derivatives in which gamma piperidinobutyrophenone derivatives of the formula, wherein R1 is hydrogen, halogen, amino, acylamino, alkylamino or N-acylalkylamino; R2 is hydrogen or halogen; R3 is hydrogen or unsubstituted or alkyl-, alkoxy-, halogen- or trifluoromethylsubstituted phenyl; and R4 is hydrogen or hydroxyl, can be prepared by reacting an indole derivative of the formula, wherein R2, R3 and R4 are as defined above, and R5 and R6 are each independently hydrogen or alkyl, with an oxidizing agent to yield an o-acylamino- gamma -piperidinobutyrophenone derivative of the formula, wherein R2, R3, R4, R5 and R6 are as defined above, and further, if necessary, hydrolyzing the product to yield an o-amino- gamma -piperidinobutyrophenone derivative of the formula, wherein R2, R3, R4 and R5 are as defined above, and further diazotizing, if desired, in case R5 is hydrogen, the obtained oamino- gamma -piperidinobutyrophenone derivative and subsequently decomposing the resultant diazonium compound to replace the diazonium group by hydrogen or halogen. Among the butyrophenone derivatives thus obtained, those in which R1 is halogen, amino, acylamino, alkylamino or N-acylalkylamino are novel compounds.
Inventors
- 👤 Hisao Yamamoto
- 👤 Tadashi Okamoto
- 👤 Kikuo Sasajima
- 👤 Masaru Nakao
- 👤 Isamu Maruyama
- 👤 Shigenari Katayama
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:07
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/52
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
5 words
A COMPOUND OF THE FORMULA,
Claim 2
Dependent Claim
5 words
A COMPOUND OF THE FORMULA,
Claim 3
Dependent Claim
5 words
A compound of the formula,
Claim 4
Dependent Claim
5 words
A compound of the formula,
Claim 5
Dependent Claim
9 words
gamma -(4-p-Chlorophenyl-4-hydroxypiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim
9 words
gamma -(4-p-Chlorophenyl-4-hydroxypiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
9 words
gamma -(4-p-Chlorophenyl-4-hydroxypiperidino)-2-amino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim
9 words
gamma -(4-p-Chlorophenyl-4-hydroxypiperidino)-2-amino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim
9 words
gamma -(4-Hydroxy-4-m-trifluoromethylpiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 10
Dependent Claim
9 words
gamma -(4-Hydroxy-4-m-trifluoromethylpiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 11
Dependent Claim
9 words
gamma -(4-Hydroxy-4-m-trifluomethylphenylpiperidino)-2-amino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 12
Dependent Claim
9 words
gamma -(4-Hydroxy-4-m-trifluomethylphenylpiperidino)-2-amino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 13
Dependent Claim
9 words
gamma -(4-p-Chlorophenyl-4-hydroxypiperidino)-2-chloro-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 14
Dependent Claim
9 words
gamma -(4-p-Chlorophenyl-4-hydroxypiperidino)-2-chloro-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 15
Dependent Claim
10 words
gamma -(4-Hydroxy-4-m-trifluoromethylphenylpiperidino)-2-methylamino-4 -fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 16
Dependent Claim
10 words
gamma -(4-Hydroxy-4-m-trifluoromethylphenylpiperidino)-2-methylamino-4 -fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 17
Dependent Claim
9 words
gamma -(4-Hydroxy-4-p-methoxyphenylpiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 18
Dependent Claim
9 words
gamma -(4-Hydroxy-4-p-methoxyphenylpiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 19
Dependent Claim
9 words
gamma -(4-Hydroxy-4-p-tolylpiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 20
Dependent Claim
9 words
gamma -(4-Hydroxy-4-p-tolylpiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 21
Dependent Claim
8 words
gamma -(4-Hydroxy-4-p-tolylpiperidino)-2-amino-4-fluorobutyrophenone and pharmaceutically acceptable acid salts thereof.
Claim 22
Dependent Claim
8 words
gamma -(4-Hydroxy-4-p-tolylpiperidino)-2-amino-4-fluorobutyrophenone and pharmaceutically acceptable acid salts thereof.
Claim 23
Dependent Claim
9 words
gamma -(4-Hydroxy-4-phenylpiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 24
Dependent Claim
9 words
gamma -(4-Hydroxy-4-phenylpiperidino)-2-acetamino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 25
Dependent Claim
9 words
gamma -(4-Hydroxy-4-phenylpiperidino)-2-amino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 26
Dependent Claim
9 words
gamma -(4-Hydroxy-4-phenylpiperidino)-2-amino-4-fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 27
Dependent Claim
10 words
gamma -(4-Hydroxy-4-m-trifluoromethylphenylpiperidino)-2-propionylamino-4 -fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 28
Dependent Claim
10 words
gamma -(4-Hydroxy-4-m-trifluoromethylphenylpiperidino)-2-propionylamino-4 -fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 29
Dependent Claim
10 words
gamma -(4-Hydroxy-4-m-trifluoromethylphenylpiperidino)-2-(N-acetyl)methyl-amino-4 -fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 30
Dependent Claim
10 words
gamma -(4-Hydroxy-4-m-trifluoromethylphenylpiperidino)-2-(N-acetyl)methyl-amino-4 -fluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 31
Dependent Claim
10 words
gamma -(4-Hydroxy-4-m-trifluoromethylphenylpiperidino)-2-chloro-4 -FLUOROBUTYROPHENONE and pharmaceutically acceptable acid addition salts thereof.
Claim 32
Dependent Claim
10 words
gamma -(4-Hydroxy-4-m-trifluoromethylphenylpiperidino)-2-chloro-4 -FLUOROBUTYROPHENONE and pharmaceutically acceptable acid addition salts thereof.
Claim 33
Dependent Claim
9 words
gamma -(40Hydroxy-4-m-trifluoromethylphenylpiperidino)-2,4-difluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
Claim 34
Dependent Claim
9 words
gamma -(40Hydroxy-4-m-trifluoromethylphenylpiperidino)-2,4-difluorobutyrophenone and pharmaceutically acceptable acid addition salts thereof.
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) | 1978-09-22 | 1979-03-24 | 1979-09-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-09-22 | 1983-03-24 | 1983-09-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-09-22 | 1987-03-24 | 1987-09-23 | $7700.00 | Window Closed / Lapsed |