US3978084A
Expired / Lapsed
US
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Synthesis of biotin
Assignee: Hoffmann La Roche Inc
•
Filing: 1973-12-03
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Granted: 1976-08-31
•
Expires: 1993-12-03
Abstract
Abstract Synthesis of biotin from 4-carbomethoxy-2-(4,5-dihydrothiophen-3(2H)-one)-valeric acid methyl ester, and thiophene intermediates in this synthesis.
Inventors
- 👤 Pasquale Nicholas Confalone
- 👤 Milan Radoje Uskokovic
- 👤 Giacomo Pizzolato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:03
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/36; C07D333/38
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
25 words
A compound of the formula: ##SPC25## wherein R 2 is lower alkyl; R 3 is aliphatic hydrocarbyl, and R 4 is hydroxy, or lower alkoxy.
Claim 2
Dependent Claim
25 words
A compound of the formula: ##SPC25## wherein R 2 is lower alkyl; R 3 is aliphatic hydrocarbyl, and R 4 is hydroxy, or lower alkoxy.
Claim 3
Dependent Claim
13 words
The compound of claim 1 wherein said compound is 3-carbethoxyamino-4-carbomethoxyamino-2-thiophenevaleric acid methyl ester.
Claim 4
Dependent Claim
11 words
The compound of claim 1 wherein said compound is 3-carbethoxyamino-4-carbomethoxyamino-2-thiophenevaleric acid.
Claim 5
Dependent Claim
11 words
The compound of claim 1 wherein said compound is 3-carbethoxyamino-4-carbo-3-pinyloxyamino-2-thiophenevaleric acid.
Claim 6
Dependent Claim
18 words
A compound of the formula: ##SPC26## wherein R 2 is lower alkyl; and R 3 is aliphatic hydrocarbyl.
Claim 7
Dependent Claim
18 words
A compound of the formula: ##SPC26## wherein R 2 is lower alkyl; and R 3 is aliphatic hydrocarbyl.
Claim 8
Dependent Claim
12 words
The compound of claim 5 wherein said compound is all cis-c,1-3-carbethoxyamino-4-carbomethoxyamino-2-tetrahydrothiophenevaleric acid.
Claim 9
Dependent Claim
130 words
A process for obtaining a compound of the formula: ##SPC27## wherein R 2 is lower alkyl; and R 3 is aliphatic hydrocarbyl; comprising hydrogenating a compound of the formula: ##SPC28## wherein R 2 and R 3 are as above; in the presence of a noble metal catalyst and a solvent, said solvent being selected from the group consisting of a. methanol, ethanol, dioxane, tetrahydrofuran, having in combination therewith a catalytic amount of a lower alkanoic acid, a lower alkane dicarboxylic acid or an aryl lower alkanoic acid, b. lower alkanoic acid, lower alkane dicarboxylic acid, or an aryl lower alkanoic acid, as sole solvent, said hydrogenation being carried out at a temperature of from about 25°C. to about 110°C. and a pressure of from about 1500 to about 2000 psi.
Claim 10
Dependent Claim
130 words
A process for obtaining a compound of the formula: ##SPC27## wherein R 2 is lower alkyl; and R 3 is aliphatic hydrocarbyl; comprising hydrogenating a compound of the formula: ##SPC28## wherein R 2 and R 3 are as above; in the presence of a noble metal catalyst and a solvent, said solvent being selected from the group consisting of a. methanol, ethanol, dioxane, tetrahydrofuran, having in combination therewith a catalytic amount of a lower alkanoic acid, a lower alkane dicarboxylic acid or an aryl lower alkanoic acid, b. lower alkanoic acid, lower alkane dicarboxylic acid, or an aryl lower alkanoic acid, as sole solvent, said hydrogenation being carried out at a temperature of from about 25°C. to about 110°C. and a pressure of from about 1500 to about 2000 psi.
Claim 11
Dependent Claim
14 words
The process of claim 7 wherein said catalyst is platinum, palladium, ruthenium or rhodium.
Claim 12
Dependent Claim
15 words
The process of claim 7 wherein said reaction is carried out in glacial acetic acid.
Claim 13
Dependent Claim
26 words
The process of claim 7 wherein R 3 is a residue of an optically active, aliphatic hydrocarbyl alcohol, cycloaliphatic hydrocarbyl alcohol or aryl lower alkyl alcohol.
Claim 14
Dependent Claim
13 words
The process of claim 10 wherein R 3 is pinyl, bornyl or menthyl.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-31 | 1980-03-01 | 1980-08-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-31 | 1984-03-01 | 1984-08-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-31 | 1988-03-01 | 1988-08-31 | $7700.00 | Window Closed / Lapsed |