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US3945888A
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Method for the production of cephalosporins
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1973-12-04
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Granted: 1976-03-23
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Expires: 1993-12-04
Abstract
Abstract A new method for production of a cephalosporin ester (I) which comprises reacting a derivative of an organic acid (II) with a 7-aminocephem compound (III) in the presence of an enzyme of a microorganism of one of the genera Escherichia, Bacillus, Proteus and Pseudomonas: ##SPC1## ##EQU1## ##SPC2## wherein R is an unsaturated six-membered carbocyclic ring or five-membered heterocyclic ring residue which may optionally have uncharged substituent groups; R 1 is hydrogen or an uncharged substituent group such as hydroxyl or halogen; R 2 is a hydrogen atom or an organic group which is bound through an oxygen, sulfur or nitrogen atom; COOR 3 is a group which may easily be converted to COOH.
Inventors
- 👤 Takeshi Takahashi
- 👤 Kenji Kawahara
- 👤 Toshiyuki Takahashi
- 👤 Koichi Kato
- 👤 Yoshio Yamazaki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 18:59
CPC Classifications
C; C12; C12P; C12P35/00; C12P35/04; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/848; Y10S435/849; Y10S435/873; Y10S435/874
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
173 words
A method for the production of a cephalosporin of the formula: ##SPC9## wherein R is an unsaturated six-membered carbocyclic ring or five-membered heterocyclic ring residue which may have uncharged substituent(s); R 1 hydrogen, hydroxy, or halogen; R 2 is a hydrogen atom or an organic group which is bound through an oxygen, sulfur or nitrogen atom; COOR 3 is an ester group which may be easily converted to COOH, which comprises reacting a derivative of an organic acid of the formula: ##EQU4## wherein R and R 1 have the same meaning as defined above with 7-aminocephem-4-carboxilic acid ester of the formula: ##SPC10## wherein R 2 and COOR 3 have the same meaning as defined above in the presence of a culture or the enzyme containing processed matter of said culture of the microorganism of one of the genera Escherichia, Bacillus, Proteus and Pseudomonas which is able to synthesize a cephalosporin of the formula (I) from a derivative of the organic acid of the formula (II) and 7-aminocephem-4-carboxylic acid ester of the formula (III).
Claim 2
Independent Claim
173 words
A method for the production of a cephalosporin of the formula: ##SPC9## wherein R is an unsaturated six-membered carbocyclic ring or five-membered heterocyclic ring residue which may have uncharged substituent(s); R 1 hydrogen, hydroxy, or halogen; R 2 is a hydrogen atom or an organic group which is bound through an oxygen, sulfur or nitrogen atom; COOR 3 is an ester group which may be easily converted to COOH, which comprises reacting a derivative of an organic acid of the formula: ##EQU4## wherein R and R 1 have the same meaning as defined above with 7-aminocephem-4-carboxilic acid ester of the formula: ##SPC10## wherein R 2 and COOR 3 have the same meaning as defined above in the presence of a culture or the enzyme containing processed matter of said culture of the microorganism of one of the genera Escherichia, Bacillus, Proteus and Pseudomonas which is able to synthesize a cephalosporin of the formula (I) from a derivative of the organic acid of the formula (II) and 7-aminocephem-4-carboxylic acid ester of the formula (III).
Claim 3
Dependent Claim
49 words
A method according to claim 1, wherein the derivative of the organic acid of the formula (II) is one which can be hydrolyzed in aqueous medium in the presence of a culture or a processed matter of the microorganism employed to give the organic acid of the formula (II).
Claim 4
Dependent Claim
41 words
A method according to claim 1, wherein R 2 is hydrogen, alkoxy, alkylcarbonyloxy, pyridylthio, pyridinium, alkylthiocarbonyloxy, dialkylaminothiocarbonylthio, alkylammonium, --N 3 , aralkyloxycarbonylamino or pyridazinylthio-N-oxide and R 3 is halogenoalkyl, alkyl(or aryl) sulfonylalkyl, alkyl, alkoxyalkyl, alkylcarbonylakyl, diarylthioalkyl or alkyl (or aryl) sulfinylalkyl.
Claim 5
Dependent Claim
42 words
A method according to claim 2, wherein R 2 is hydrogen, alkoxy, alkylcarbonyloxy, pyridylthio, pyridinium, alkylthiocarbonyloxy, dialkylaminothiocarbonylthio, alkylammonium, --N 3 , aralkyloxycarbonylamino or pyridazinylthio-N-oxide and R 3 is halogenoalkyl, alkyl (or aryl) sulfonylalkyl, alkyl, alkoxyalkyl, alkylcarbonylalkyl, diarythioalkyl or alkyl (or aryl) sulfinylalkyl.
Claim 6
Dependent Claim
40 words
A method according to claim 4, wherein the derivative of the organic acid of the formula (II) is an amino acid ester, a glycolic acid ester, a thioglycolic acid ester, an amide or alkyl ester of the said organic acid.
Claim 7
Dependent Claim
12 words
A method according to claim 1, wherein the microorganism is Escherichia coli.
Claim 8
Dependent Claim
45 words
A method according to claim 4, wherein the microorganism is Escherichia coli IFO-3542, escherichia coli ATCC-9637, escherichia coli var. communior IFO-3547, escherichia coli var. communior IFO-3548, escherichia coli IFO-13502, escherichia coli IFO-3470, escherichia coli IFO-3450, bacillus sp. IFO-12063, proteus rettgeri ATCC-9250 or Pseudomonas putida IFO-3537.
References Cited (Backward Citations)
US3816253A
Cited
US3862004A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-03-23 | 1979-09-22 | 1980-03-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-23 | 1983-09-22 | 1984-03-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-23 | 1987-09-22 | 1988-03-23 | $7700.00 | Window Closed / Lapsed |