GB1467407A - Process for the manufacture of 7-beta-acylaminoceph-3-em- 4-carboxylic acid compounds - Google Patents
Process for the manufacture of 7-beta-acylaminoceph-3-em- 4-carboxylic acid compoundsInfo
- Publication number
- GB1467407A GB1467407A GB1372074A GB1372074A GB1467407A GB 1467407 A GB1467407 A GB 1467407A GB 1372074 A GB1372074 A GB 1372074A GB 1372074 A GB1372074 A GB 1372074A GB 1467407 A GB1467407 A GB 1467407A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- formula
- prepared
- trifluoroacetylaminomethyl
- thiophene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1467407 7 - Acylamino - ceph - 3 - em - 4- carboxylic acids and derivatives thereof CIBAGEIGY AG 28 March 1974 [30 March 1973] 13720/74 Heading C2C Novel compounds of the Formula I wherein X is sulphur or oxygen, R is hydrogen or an amino protective group, R 1 is hydrogen, a free etherified or esterified hydroxyl or mercapto group, or a substituted ammonium group, R 2 is hydroxyl or a carboxyl protective radical which together with the carbonyl grouping of the formula -C(: O)- forms a protected carboxyl group, or salts thereof, may be prepared by acylating a compound of the Formula II wherein the amino group is optionally substituted by a group which permits acylation to take place, or a salt thereof with carboxylic of the Formula III or a reactive derivative thereof and optionally removing or interconverting protective groups at R and R 2 , converting R 1 groups to other R 1 groups and forming salts or free compounds. 2 - (5 - N - tert. - Butoxycarbonylaminomethyl- 2-thienyl acetic acid is prepared by reacting thenylamine hydrochloride with trifluoroacetic acid and acetic anhydride to form 2-acetyl-5- trifluoroacetylaminomethyl-thiophene which with perchloric acid, thallium nitrate and methanol yields 2 - (5 - trifluoroacetylaminomethyl - 2- thienyl) acetic acid, methyl ester which with base and then t-butoxycarbonyl azide yields the required compound. 2-(5-N-t-Butoxycarbonylamino-2-furyl) acetic acid is prepared by an analogous process from furfurylamine. 2-Acetyl- 5 - trifluoroacetylaminomethyl - thiophene is also prepared by reacting thiophene with N- hydroxymethyltrifluoroacetamide in trifluoroacetic acid and acetic anhydride. Pharmaceutical compositions of the compounds I in which R is hydrogen and R 2 is hydroxyl or a radical which together with the carbonyl grouping of the formula -C(=O)- forms an esterified carbonyl group which can be split under physiological conditions or a physiologically acceptable salt thereof, with the usual excipients show antibiotic activity when administered orally or parenterally.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH460873A CH583240A5 (en) | 1973-03-30 | 1973-03-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1467407A true GB1467407A (en) | 1977-03-16 |
Family
ID=4279271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1372074A Expired GB1467407A (en) | 1973-03-30 | 1974-03-28 | Process for the manufacture of 7-beta-acylaminoceph-3-em- 4-carboxylic acid compounds |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS49126693A (en) |
BE (1) | BE813076A (en) |
BG (1) | BG21610A3 (en) |
CH (1) | CH583240A5 (en) |
DE (1) | DE2413572A1 (en) |
FR (1) | FR2283685A1 (en) |
GB (1) | GB1467407A (en) |
NL (1) | NL7404248A (en) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3459747A (en) * | 1967-02-15 | 1969-08-05 | American Cyanamid Co | Substituted 7-acetylamino cephalosporanic acids |
US3382241A (en) * | 1967-02-27 | 1968-05-07 | Lilly Co Eli | Certain orally active cephalosporin antibiotics |
-
1973
- 1973-03-30 CH CH460873A patent/CH583240A5/xx not_active IP Right Cessation
-
1974
- 1974-03-21 DE DE2413572A patent/DE2413572A1/en active Pending
- 1974-03-26 FR FR7410246A patent/FR2283685A1/en active Granted
- 1974-03-28 GB GB1372074A patent/GB1467407A/en not_active Expired
- 1974-03-28 NL NL7404248A patent/NL7404248A/xx unknown
- 1974-03-29 BE BE142663A patent/BE813076A/en unknown
- 1974-03-29 JP JP49034814A patent/JPS49126693A/ja active Pending
- 1974-03-29 BG BG26242A patent/BG21610A3/xx unknown
Also Published As
Publication number | Publication date |
---|---|
NL7404248A (en) | 1974-10-02 |
FR2283685A1 (en) | 1976-04-02 |
CH583240A5 (en) | 1976-12-31 |
FR2283685B1 (en) | 1978-07-28 |
BG21610A3 (en) | 1976-07-20 |
BE813076A (en) | 1974-09-30 |
JPS49126693A (en) | 1974-12-04 |
DE2413572A1 (en) | 1974-10-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |