Patent US3930949A successfully refreshed from Google Patents.
US3930949A
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Process for the production of 7-amino-Δ3 -cephem derivatives
Assignee: Bayer AG
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Filing: 1974-10-22
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Granted: 1976-01-06
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Expires: 1994-10-22
Abstract
Abstract 7-Amino-Δ 3 -cephem derivatives of the formula: ##SPC1## Wherein: R is hydrogen; hydroxy; amino; cyano; --O--CO--NH 2 ; ##EQU1## wherein n is an integer from 4 to 6; --O--CO--R 1 ; --NH--CO--R 1 or --S--CS--O--R 1 wherein R 1 is alkyl of 1 to 4 carbon atoms; -S-Het or Het wherein Het is a 5- or 6-membered hetero-aromatic ring unsubstituted or substituted by 1 to 3 alkyl moieties of 1 to 3 carbon atoms or said ring having a positive charge; and X is hydrogen; or, is a negative charge if R has a positive charge, Are obtained by reacting a compound of the formula: ##SPC2## Or a salt thereof with an inorganic or organic base, Wherein: R and X are as above defined; R 2 is phenyl, phenoxy, 2-thienyl or 2-furyl, unsubstituted or substituted in the ring by amino, hydroxy or alkyl of 1 to 3 carbon atoms; and R 3 is hydrogen, amino, hydroxy or alkyl of 1 to 3 carbon atoms, With penicillinacylase which is bound by convalent bonds to a water-insoluble carrier.
Inventors
- 👤 Carl Kutzbach
- 👤 Uwe Petersen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 19:40
CPC Classifications
C; C12; C12N; C12N11/00; C12N11/02; C12N11/10; C12N11/08; C12N11/082; C12N11/087; C12P; C12P35/00; C12P35/02; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/848; Y10S435/849
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
179 words
A process for the production of a compound of the formula: ##SPC18## wherein: R is hydrogen; hydroxy; amino; cyano; --O--CO--NH 2 ; ##EQU3## wherein n is an integer from 4 to 6; --O--CO--R 1 ; --NH--CO--R 1 or --S--CS--O--R 1 wherein R 1 is alkyl of 1 to 4 carbon atoms; -S-Het or Het wherein Het is a 5- or 6-membered hetero-aromatic ring unsubstituted or substituted by 1 to 3 alkyl moieties of 1 to 3 carbon atoms or said ring having a positive charge; and X is hydrogen; or, is a negative charge if R has a positive charge, which comprises reacting a compound of the formula: ##SPC19## or a salt thereof with an inorganic or organic base, wherein: R and X are as above defined; R 2 is phenyl, phenoxy, 2-thienyl or 2-furyl, unsubstituted or substituted in the ring by amino, hydroxy or alkyl of 1 to 3 carbon atoms; and R 3 is hydrogen, amino, hydroxy or alkyl of 1 to 3 carbon atoms, with penicillinacylase which is bound by covalent bonds to a water-insoluble carrier.
Claim 2
Dependent Claim
179 words
A process for the production of a compound of the formula: ##SPC18## wherein: R is hydrogen; hydroxy; amino; cyano; --O--CO--NH 2 ; ##EQU3## wherein n is an integer from 4 to 6; --O--CO--R 1 ; --NH--CO--R 1 or --S--CS--O--R 1 wherein R 1 is alkyl of 1 to 4 carbon atoms; -S-Het or Het wherein Het is a 5- or 6-membered hetero-aromatic ring unsubstituted or substituted by 1 to 3 alkyl moieties of 1 to 3 carbon atoms or said ring having a positive charge; and X is hydrogen; or, is a negative charge if R has a positive charge, which comprises reacting a compound of the formula: ##SPC19## or a salt thereof with an inorganic or organic base, wherein: R and X are as above defined; R 2 is phenyl, phenoxy, 2-thienyl or 2-furyl, unsubstituted or substituted in the ring by amino, hydroxy or alkyl of 1 to 3 carbon atoms; and R 3 is hydrogen, amino, hydroxy or alkyl of 1 to 3 carbon atoms, with penicillinacylase which is bound by covalent bonds to a water-insoluble carrier.
Claim 3
Dependent Claim
79 words
A process according to claim 1 wherein R 1 is alkyl of 1 or 2 carbon atoms; n is 4 or 5; said hetero-aromatic ring contains from 1 to 3 of the same or different hetero-atoms selected from the group consisting of oxygen, sulfur and nitrogen, the alkyl substituent on said hetero-aromatic ring is of 1 or 2 carbon atoms and the alkyl substituent on the phenyl, phenoxy, 2-thienyl or 2-furyl substituent is of 1 or 2 carbon atoms.
Claim 4
Dependent Claim
42 words
A process according to claim 1 wherein R, r 3 and X are each hydrogen; and R 2 is phenyl or phenoxy; or R is --O--CO--CH 3 ; R 3 and X are each hydrogen; and R 2 is phenyl or phenoxy.
Claim 5
Dependent Claim
36 words
A process according to claim 1 wherein R is hydrogen, --O--CO--CH 3 ; or ##SPC20## R 2 is phenyl, phenoxy or thienyl; R 3 is hydrogen or amino; and X is hydrogen or a negative charge.
Claim 6
Dependent Claim
28 words
A process according to claim 1 wherein R is hydrogen or --O--CO--CH 3 ; R 2 is phenyl or phenoxy; R 3 is hydrogen; and X is hydrogen.
Claim 7
Dependent Claim
36 words
A process according to claim 1 wherein R is hydrogen, --O--CO--CH 3 , or ##SPC21## R 2 is phenyl, phenoxy or thienyl; R 3 is hydrogen or amino; and X is hydrogen or a negative charge.
Claim 8
Dependent Claim
61 words
A process according to claim 1 wherein the penicillinacylase is bound to cross-linked polymers which consist essentially of copolymeric units comprising: a. 0.1 to 50% by weight of α-β-mono-olefinically unsaturated dicarboxylic anhydrides of 4 to 9 carbon atoms; and b. 99.9 to 50% by weight of at least one member selected from the group consisting of diacrylates, polyacrylates, dimethacrylates and polymethacrylates.
Claim 9
Dependent Claim
85 words
A process according to claim 7 wherein the penicillinacylase is bound to copolymers which consist essentially of cross-linked polymers wherein the copolymerized units comprise: a. 0.1 to 30% by weight of α-β-mono-olefinically unsaturated dicarboxylic acid anhydrides of 4 to 9 carbon atoms; b. 35 to 90% by weight of at least one member selected from the group consisting of diacrylates, polyacrylates, dimethacrylates and polyacrylates; and c. 5 to 60% by weight of at least one hydrophilic monomer other than those set forth in (b) above.
Claim 10
Dependent Claim
14 words
A process according to claim 1 wherein the penicillinacylase is obtained from E. coli.
Claim 11
Dependent Claim
13 words
A process according to claim 9 wherein the E. coli is ATCC 11,105.
Claim 12
Dependent Claim
42 words
A process according to claim 1 for the production of 7-aminocephalosporanic acid which comprises reacting the sodium salt of 7-(2-thienyl)-acetamido-cephalosporanic acid with penicillinacylase obtained from E. coli bound by covalent bonds to a water-insoluble carrier comprising tetraethylene glycol dimethacrylate and maleic anhydride.
Claim 13
Dependent Claim
40 words
A process according to claim 1 for the production of 7-amino-3-pyridiniummethyl-Δ 3 -cephem-4-carboxylate which comprises reacting 7-(2-thienyl)-acetamido-3-pyridiniummethyl-Δ 3 -cephem-4-carboxylate with penicillinacylase obtained from E. coli bound by covalent bonds to a water-insoluble carrier comprising tetraethylene glycol dimethacrylate and maleic anhydride.
Claim 14
Dependent Claim
38 words
A process according to claim 1 for the production of 7-amino-desacetoxy-cephalosporanic acid which comprises reacting 7-phenylacetamido-desacetoxy-cephalosporanic acid with penicillinacylase obtained from E. coli bound by covalent bonds to a water-insoluble carrier comprising tetraethylene glycol dimethacrylate and maleic anhydride.
Claim 15
Dependent Claim
38 words
A process according to claim 1 for the production of 7-amino-desacetoxy-cephalosporanic acid which comprises reacting 7-phenoxyacetamido-desacetoxy-cephalosporanic acid with penicillinacylase obtained from E. coli bound by covalent bonds to a water-insoluble carrier comprising tetraethylene glycol dimethacrylate and maleic anhydride.
Claim 16
Dependent Claim
38 words
A process according to claim 1 for the production of 7-amino-desacetoxy-cephalosporanic acid which comprises reacting 7-(α-amino-phenylacetyl)-desacetoxy-cephalosporanic acid with penicillinacylase obtained from E. coli bound by covalent bonds to a water-insoluble carrier comprising tetraethylene glycol dimethacrylate and maleic anhydride.
Claim 17
Dependent Claim
41 words
A process according to claim 1 for the production of 7-amino-desacetoxy-cephalosporanic acid which comprises reacting 7-phenylacetamido-desacetoxy-cephalosporanic acid with penicillinacylase obtained from E. coli bound by covalent bonds to a water-insoluble carrier which comprises tetramethylene glycol dimethacrylate, methacrylic acid and maleic anhydride.
Claim 18
Dependent Claim
41 words
A process according to claim 1 for the production of 7-amino-desacetoxy-cephalosporanic acid which comprises reacting 7-phenoxyacetamido-desacetoxy-cephalosporanic acid with penicillinacylase obtained from E. coli bound by covalent bonds to a water-insoluble carrier which comprises tetramethylene glycol dimethacrylate, methacrylic acid and maleic anhydride.
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) | 1979-01-05 | 1979-07-07 | 1980-01-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-05 | 1983-07-07 | 1984-01-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-05 | 1987-07-07 | 1988-01-06 | $7700.00 | Window Closed / Lapsed |