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US4346218A
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Cyclization process to form cephem ring
Assignee: Eli Lilly and Co
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Filing: 1980-02-27
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Granted: 1982-08-24
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Expires: 2000-02-27
Abstract
Abstract An intermediate represented by following formula for synthesizing 3-hydroxy-3-cephem compounds ##STR1## wherein A and B each is a hydrogen or amino substituent; R is a hydrogen or thiol substituent; Hal is a halogen; X is a hydroxy or carboxy protecting group; the broken line between A and R shows that when R and B are hydrogens, and A is a carboxylic acyl, the substituents can be combined to form an azetidinothiazoline bicyclic ring; and the enamine derivatives thereof.
Inventors
- 👤 Teruji Tsuji
- 👤 Yoshio Hamashima
- 👤 Mitsuru Yoshioka
- 👤 Masayuki Narisada
- 👤 Hiroshi Tanida
- 👤 Taichiro Komeno
- 👤 Wataru Nagata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:24
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/09; C07D205/095; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
173 words
A method for the production of a compound of the formula ##STR154## which comprises treating a compound of the formula ##STR155## with an acid, base, solvent, or solvent together with a catalizer selected from the group of a neutral or basic silica gel, alumina, diatomaceous earth, or florisil, wherein R' is a member selected from the group consisting of (1) hydrogen, (2) C 1 to C 4 alkyl, (3) phenyl, (4) α-chlorobenzyl, (5) ArCQQ, (6) Ar--G--CQQ wherein Q represents hydrogen or methyl, G represents oxygen or sulfur and Ar represents (a) phenyl, (b) dihydrophenyl, (c) monocyclic heterocyclic aromatic containing from 1 to 4 hetero atoms selected from the group of nitrogen, oxygen and sulfur or (d) one of said groups (a) to (c) substituted by an inert group selected from the group of alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, chlorine, bromine, iodine, fluorine, trifluoromethyl hydroxy, cyano, aminomethyl, amino and nitro, Hal is chlorine, bromine, or iodine, and X is OH or a carboxy protecting group.
Claim 2
Independent Claim
173 words
A method for the production of a compound of the formula ##STR154## which comprises treating a compound of the formula ##STR155## with an acid, base, solvent, or solvent together with a catalizer selected from the group of a neutral or basic silica gel, alumina, diatomaceous earth, or florisil, wherein R' is a member selected from the group consisting of (1) hydrogen, (2) C 1 to C 4 alkyl, (3) phenyl, (4) α-chlorobenzyl, (5) ArCQQ, (6) Ar--G--CQQ wherein Q represents hydrogen or methyl, G represents oxygen or sulfur and Ar represents (a) phenyl, (b) dihydrophenyl, (c) monocyclic heterocyclic aromatic containing from 1 to 4 hetero atoms selected from the group of nitrogen, oxygen and sulfur or (d) one of said groups (a) to (c) substituted by an inert group selected from the group of alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, chlorine, bromine, iodine, fluorine, trifluoromethyl hydroxy, cyano, aminomethyl, amino and nitro, Hal is chlorine, bromine, or iodine, and X is OH or a carboxy protecting group.
Claim 3
Dependent Claim
31 words
A process according to claim 1 wherein the acid is a mineral acid, sulfonic acid, phosphonic acid, or carboxylic acid, or their salts with a weak base, or their acidic salts.
Claim 4
Dependent Claim
13 words
A process according to claim 1 wherein the base is a weak base.
Claim 5
Dependent Claim
20 words
A process according to claim 1 wherein the solvent is an amide, alcohol, or water solvents as the cyclization reagent.
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) | 1985-08-23 | 1986-02-22 | 1986-08-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-23 | 1990-02-22 | 1990-08-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-23 | 1994-02-22 | 1994-08-24 | $7700.00 | Window Closed / Lapsed |