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US4337199A
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US
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Antibiotic β-lactam compounds, production thereof, and their use as antimicrobial agent
Assignee: Sanraku Inc
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Filing: 1980-05-06
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Granted: 1982-06-29
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Expires: 2000-05-06
Abstract
Abstract Novel antibiotic β-lactam compounds, i.e. 7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid derivatives of the following formula ##STR1## wherein R 1 represents a hydrogen atom, a methyl group or a hydroxyl group, R 2 represents a lower alkyl group, a hydroxy lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkanoyloxy-lower alkyl group, a cyclohexyl group, a phenyl group or a 5- or 6-membered aromatic heterocyclic group containing 1 or 2 nitrogen atoms, and R 3 represents a hydrogen atom, a lower alkyl group, or a substituted or unsubstituted aralkyl group containing 7 to 20 carbon atoms, and the salts thereof; processes for production thereof; use thereof as antimicrobial agents; and novel intermediates for production of the compounds of formula (I).
Inventors
- 👤 Takeo Yoshioka
- 👤 Kenichi Yamamoto
- 👤 Kaoru Yamada
- 👤 Yasuyuki Kato
- 👤 Yasutaka Shimauchi
- 👤 Tomoyuki Ishikura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 13:01
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
196 words
A process for producing a compound of the formula ##STR86## wherein R 1 represents hydrogen, methyl or hydroxyl, R 2 represents lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, lower alkanoyloxy-lower alkyl, cyclohexyl, phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrrolyl, 3-pyrrolyl, 2-imidazolyl or 4-imidazolyl, and R 3 represents hydrogen, lower alkyl or lower alkyl substituted by 1 to 3 phenyl groups which may be substituted by a substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, lower haloalkyl, nitro and lower alkylsulfonyl, or its salt, which comprises reacting a compound of the formula ##STR87## wherein R 1 is as defined above, and R 33 represents lower alkyl or lower alkyl substituted by 1 to 3 phenyl groups which may be substituted by a substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, lower haloalkyl, nitro and lower alkylsulfonyl, with a thiol compound of the formula R.sub.2 SY wherein R 2 is as defined above, and Y represents hydrogen or an alkali metal, and, to produce a compound of formula (I) in which R 3 is hydrogen, hydrogenolyzing the resulting product, and if desired, converting the resulting product to its salt.
Claim 2
Dependent Claim
196 words
A process for producing a compound of the formula ##STR86## wherein R 1 represents hydrogen, methyl or hydroxyl, R 2 represents lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, lower alkanoyloxy-lower alkyl, cyclohexyl, phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrrolyl, 3-pyrrolyl, 2-imidazolyl or 4-imidazolyl, and R 3 represents hydrogen, lower alkyl or lower alkyl substituted by 1 to 3 phenyl groups which may be substituted by a substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, lower haloalkyl, nitro and lower alkylsulfonyl, or its salt, which comprises reacting a compound of the formula ##STR87## wherein R 1 is as defined above, and R 33 represents lower alkyl or lower alkyl substituted by 1 to 3 phenyl groups which may be substituted by a substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, lower haloalkyl, nitro and lower alkylsulfonyl, with a thiol compound of the formula R.sub.2 SY wherein R 2 is as defined above, and Y represents hydrogen or an alkali metal, and, to produce a compound of formula (I) in which R 3 is hydrogen, hydrogenolyzing the resulting product, and if desired, converting the resulting product to its salt.
Claim 3
Dependent Claim
36 words
The process of claim 1 wherein R 2 in the thiol compound represents alkyl having 1 to 4 carbon atoms, hydroxyethyl, ethoxyethyl, acetyloxyethyl, cyclohexyl, phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrrolyl, 3-pyrrolyl, 2-imidazolyl or 4-imidazolyl.
Claim 4
Dependent Claim
20 words
The process of claim 1 wherein R 2 in the thiol compound represents 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl or 5-pyrimidinyl.
Claim 5
Dependent Claim
58 words
The process of claim 1 which produces a compound of the formula ##STR88## wherein R 1 is as defined in claim 29, R 21 represents alkyl having 1 to 4 carbon atoms, hydroxyethyl, ethoxyethyl, acetyloxyethyl, cyclohexyl, phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrrolyl, 3-pyrrolyl, 2-imidazolyl or 4-imidazolyl, and R 31 represents hydrogen, methyl, benzyl, p-nitrobenzyl or benzhydryl.
Claim 6
Dependent Claim
40 words
The process of claim 1 which produces a compound of the formula ##STR89## wherein R 1 is as defined in claim 29, R 22 represents phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl or 5-pyrimidinyl, and R 32 represents hydrogen or p-nitrobenzyl.
Claim 7
Dependent Claim
21 words
The process of claim 1 wherein the reaction is carried out at a temperature of not more than about -20° C.
Claim 8
Dependent Claim
28 words
The process of claim 1 wherein the reaction is carried out in a solvent selected from the group consisting of N,N-dimethylformamide, tetrahydrofuran, dioxane, hexamethyl phosphoric triamide and glyme.
Claim 9
Dependent Claim
28 words
The process of claim 1 wherein the thiol compound is used in an amount of 1.1 to 1.5 moles per mole of the compound of the formula (II).
Claim 10
Dependent Claim
14 words
The process of claim 1 wherein R 2 in the thiol compound represents phenyl.
Claim 11
Dependent Claim
30 words
The process of claim 1 wherein R 33 in the compound of the formula (II) represents benzyl, phenethyl, benzhydryl, trityl, p-nitrobenzyl, o-nitrobenzyl, p-chlorobenzyl, o-chlorobenzyl, p-fluorobenzyl, p-bromobenzyl, p-methoxybenzyl, p-methylsulfonylbenzyl or p-trifluoromethylbenzyl.
Claim 12
Dependent Claim
21 words
The process of claim 1 wherein R 33 in the compound of the formula (II) represents methyl, benzyl, p-nitrobenzyl or benzhydryl.
Claim 13
Dependent Claim
17 words
The process of claim 1 wherein R 33 in the compound of the formula (II) represents p-nitrobenzyl.
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) | 1985-06-28 | 1985-12-28 | 1986-06-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-06-28 | 1989-12-28 | 1990-06-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-06-28 | 1993-12-28 | 1994-06-29 | $7700.00 | Window Closed / Lapsed |