GB1360860A - Cepham compounds process for their manufacture and compositions containing them - Google Patents
Cepham compounds process for their manufacture and compositions containing themInfo
- Publication number
- GB1360860A GB1360860A GB3087571A GB3087571A GB1360860A GB 1360860 A GB1360860 A GB 1360860A GB 3087571 A GB3087571 A GB 3087571A GB 3087571 A GB3087571 A GB 3087571A GB 1360860 A GB1360860 A GB 1360860A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- hydrogen
- compounds
- denotes
- formula
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 150000001781 cephams Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- -1 2,4,6-trihydroxy - phenyl Chemical group 0.000 abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 11
- 150000001875 compounds Chemical class 0.000 abstract 8
- 229930186147 Cephalosporin Natural products 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 229940124587 cephalosporin Drugs 0.000 abstract 2
- 150000001780 cephalosporins Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 abstract 1
- ZPKLKQNMZTUIFZ-UHFFFAOYSA-N 2-phenylethanone Chemical compound O=[C]CC1=CC=CC=C1 ZPKLKQNMZTUIFZ-UHFFFAOYSA-N 0.000 abstract 1
- XRRBWJLFPKTWCQ-NFSFSXTOSA-N CC(C[S+]([C@@H]1C2)N)=C(C([O-])=O)N1C2=O Chemical class CC(C[S+]([C@@H]1C2)N)=C(C([O-])=O)N1C2=O XRRBWJLFPKTWCQ-NFSFSXTOSA-N 0.000 abstract 1
- KOEOWHCPPBABTA-DHXZLDRASA-N CC([C@H](C([O-])=O)N([C@H]1C2)C2=O)=C[S+]1N Chemical class CC([C@H](C([O-])=O)N([C@H]1C2)C2=O)=C[S+]1N KOEOWHCPPBABTA-DHXZLDRASA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- 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
-
- 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)
Abstract
1360860 Cephalosporins CIBA-GEIGY AG 1 July 1971 [8 July 1970 3 Dec 1970] 30875/71 Heading C2A The invention relates to 7-N-R<SP>a</SP> 1 -N-R<SP>b</SP> 1 - amino - 3 - R - methyl - ceph - 2 - em - 4 - carboxylic acid compounds of Formula 1 wherein R represents a radical, possessing a hydrogen and being bonded via a carbon atom, of an organic C-nucleophilic compound, R<SP>a</SP> 1 is hydrogen or an amino protective group R<SP>a</SP> 1 , R<SP>b</SP> 1 is hydrogen or an acyl group or R<SP>a</SP> 1 and R 1 <SP>b</SP> together denote a bivalent amino protective group, and R 2 represents hydrogen or a radical R<SP>a</SP> 2 which together with the -C(=O)-O- grouping forms a protected carboxyl group, or salts of such compounds which have saltforming groups. Also 7-N-R<SP>a</SP> 1 -N-R<SP>b</SP> 1 -amino-3- R - methyl - ceph - 3 - em - 4 - carboxylic acid compounds of Formula IV wherein R, R<SP>a</SP> 1 , R<SP>b</SP> 1 and R<SP>a</SP> 2 are as defined above, with the exception of (i) compounds of Formula IV in which R denotes an unsubstituted or substituted pyrryl or indolyl radical or a dicarbonylmethyl radical, in which each of the carbonyl groups is part of an acyl radical or an esterified carboxyl group, or both together are part of a diacyl radical, R<SP>a</SP> 1 represents hydrogen or an acyl radical Ac, R<SP>b</SP> 1 denotes hydrogen and R 2 has the meaning given above, (ii) compounds of the Formula IV, wherein R denotes the 2,4-dihydroxyphenyl radical, a phenyl group with two hydroxy groups in adjacent positions and an ethyl group in the m- and p-position, respectively, to these hydroxy groups, the 2,4,6-trihydroxy - phenyl, 2 - hydroxy - 1 - naphthyl, dicarboxymethyl, carboxycarbonylmethyl radical, a dimethylamino-phenyl radical, the 1- oxido-2-picolyl or the 2-hydroxy-1-4-dioxo-1-4- dihydro-3-naphthyl radical, R<SP>a</SP> 1 denotes the phenylacetyl radical and R<SP>b</SP> 1 and R 2 denote hydrogen, (iii) compounds of the Formula IV, wherein R represents 2,4-dimethoxy-phenyl, R<SP>a</SP> 1 denotes phenylacetyl, R<SP>b</SP> 1 denotes hydrogen and R 2 is methyl, (iv) compounds of the Formula IV, wherein R represents 2-oxocyclohexyl, R<SP>a</SP> 1 denotes hydrogen, 2-thienylacetyl, α - amino - phenylacetyl or α - (tert. - butyloxycarbonyl) - aminophenylacetyl, R<SP>b</SP> 1 denotes hydrogen and R 2 represents diphenylmethyl, and (v) compounds of the Formula IV, wherein R denotes 2-oxo-cyclohexyl, R<SP>a</SP> 1 represents 2- thienylacetyl or α-amino-phenylacetyl, R<SP>b</SP> 1 represents hydrogen and R 2 represents hydrogen. The invention also relates to 1-oxides corresponding to the ceph-3-em compounds - of Formula IV but without the above restrictions on groupings present. Pharmaceutical compositions suitable for oral or parenteral administration may be prepared using the above compounds as the active ingredient. Processes for the preparation of the above cephalosporins are described.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1030570 | 1970-07-08 | ||
| CH1787870 | 1970-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1360860A true GB1360860A (en) | 1974-07-24 |
Family
ID=25706322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3087571A Expired GB1360860A (en) | 1970-07-08 | 1971-07-01 | Cepham compounds process for their manufacture and compositions containing them |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE769609A (en) |
| DD (1) | DD98095A5 (en) |
| DE (1) | DE2132883A1 (en) |
| FR (1) | FR2100876B1 (en) |
| GB (1) | GB1360860A (en) |
| NL (1) | NL7109409A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791161A (en) * | 1972-01-03 | 1973-05-09 | Beecham Group Ltd | METHOD FOR THE PREPARATION OF ANALOGUES OF CEPHALOSPORINS |
| US3994877A (en) * | 1975-07-22 | 1976-11-30 | Richardson-Merrell Inc. | 6-[α-AMINO-ω-(3,4-METHYLENEDIOXYPHENYL)ACYLAMIDO]PENICILLANIC ACID DERIVATIVES |
| US3994876A (en) * | 1975-07-22 | 1976-11-30 | Richardson-Merrell Inc. | 6-[α-AMINO-ω-(2,3-METHYLENEDIOXYPHENYL)ACYLAMIDO]PENICILLANIC ACID DERIVATIVES |
| NZ198350A (en) * | 1980-09-25 | 1985-02-28 | Toyama Chemical Co Ltd | Cephalosporins and intermediates;pharmaceutical compositions |
| EP0061234A3 (en) * | 1981-03-05 | 1983-11-16 | Beecham Group Plc | Cephalosporin derivatives, process for their preparation and pharmaceutical preparations containing them |
| FR2533216A1 (en) * | 1982-09-22 | 1984-03-23 | Toyama Chemical Co Ltd | New cephalosporins and their salts. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1337775A (en) * | 1962-05-16 | 1963-09-20 | Glaxo Lab Ltd | New cephalosporin c derivatives and their preparation methods |
| GB1241657A (en) * | 1967-08-21 | 1971-08-04 | Glaxo Lab Ltd | Improvements in or relating to cephalosporin compounds |
| FI56535C (en) * | 1968-02-07 | 1980-02-11 | Lilly Co Eli | VID FRAMSTAELLNING AV 3-CEFALOSPORINANTIBIOTIKA SAOSOM MELLANPRODUKTER ANVAENDBARA 7-SKYDDAD-AMINO- 2-CEFALOSPORANSYRAESTRAR |
-
1971
- 1971-07-01 GB GB3087571A patent/GB1360860A/en not_active Expired
- 1971-07-01 DE DE19712132883 patent/DE2132883A1/en active Pending
- 1971-07-07 DD DD156326A patent/DD98095A5/xx unknown
- 1971-07-07 BE BE769609A patent/BE769609A/en unknown
- 1971-07-07 NL NL7109409A patent/NL7109409A/xx unknown
- 1971-07-08 FR FR7124989A patent/FR2100876B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2100876A1 (en) | 1972-03-24 |
| NL7109409A (en) | 1972-01-11 |
| FR2100876B1 (en) | 1974-11-15 |
| DE2132883A1 (en) | 1972-01-13 |
| BE769609A (en) | 1972-01-07 |
| DD98095A5 (en) | 1973-06-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |