GB1261780A - Orally active sulfur-containing cephalosporin antibiotics - Google Patents
Orally active sulfur-containing cephalosporin antibioticsInfo
- Publication number
- GB1261780A GB1261780A GB63526/69A GB6352669A GB1261780A GB 1261780 A GB1261780 A GB 1261780A GB 63526/69 A GB63526/69 A GB 63526/69A GB 6352669 A GB6352669 A GB 6352669A GB 1261780 A GB1261780 A GB 1261780A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- methylthiomethyl
- ester
- group
- treatment
- 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
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title 1
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 229940088710 antibiotic agent Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- 229910052717 sulfur Inorganic materials 0.000 title 1
- 239000011593 sulfur Substances 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 4
- -1 N-protected phenylglycine Chemical class 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000005331 phenylglycines Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- 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
1,261,780. 3-Methylthiomethyl cephalosporins. ELI LILLY & CO. 31 Dec., 1969 [26 Feb., 1969], No. 63526/69. Heading C2A. Novel cephalosporanic acids of Formula I wherein R is phenyl, thienyl or phenyl substituted with OH, Cl, Br, NO 2 , CN, or C 1 -C 6 alkyl or alkoxy are prepared by acylating 3- methylthiomethyl-7-aminocephalosporanic acid or an ester thereof with N-protected phenylglycine, thienylglycine or appropriately substituted phenylglycine or an acid halide or anhydride thereof, and removing the N-protecting group, and the ester group if present. The 3-methylthiomethyl - 7 - aminocephalosporanic acid may be prepared by treating either (a) 7- aminocephalosporanic acid or (b) the corresponding 7-phenylacetamido or 7-phenoxyacetamido acid with methyl mercaptan, and in the case of (b), protecting the carboxyl group by ester formation and then splitting off the phenylacetyl or phenoxyacetyl group by treatment with PCl 5 in the presence of a tertiary amine followed by treatment with a lower alkanol and then with water or aqueous acid. Alternatively a #<SP>3</SP>-desacetoxycephalosporanic acid ester prepared by heating a penicillin sulphoxide ester under acid conditions, is isomerized to the corresponding #<SP>2</SP> compound, converted to the 3-bromomethyl derivative with N-bromosuccinimide, and treated with methyl mercaptan to give the 3-methylthiomethyl derivative which is converted to the corresponding #<SP>3</SP> isomer by treatment with a base. The 7-acylating group is then removed as described above to give the required 7-amino-3-methylthiomethyl starting material.. Pharmaceutical compositions having antibacterial activity comprise a cephalosporanic acid of Formula I together with a pharmaceutically acceptable carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80264369A | 1969-02-26 | 1969-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1261780A true GB1261780A (en) | 1972-01-26 |
Family
ID=25184304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB63526/69A Expired GB1261780A (en) | 1969-02-26 | 1969-12-31 | Orally active sulfur-containing cephalosporin antibiotics |
Country Status (17)
| Country | Link |
|---|---|
| AT (1) | AT296501B (en) |
| BE (1) | BE743754A (en) |
| BR (1) | BR6915176D0 (en) |
| CH (1) | CH536321A (en) |
| DE (1) | DE2000111A1 (en) |
| DO (1) | DOP1970001696A (en) |
| ES (1) | ES375237A1 (en) |
| FR (1) | FR2032408B1 (en) |
| GB (1) | GB1261780A (en) |
| GT (1) | GT196915584A (en) |
| IL (1) | IL33522A0 (en) |
| LU (1) | LU60150A1 (en) |
| NL (1) | NL6919698A (en) |
| PL (1) | PL80818B1 (en) |
| RO (1) | RO56960A (en) |
| SU (1) | SU383302A3 (en) |
| ZA (1) | ZA698494B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409215A (en) | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7112483A (en) * | 1970-09-14 | 1972-03-16 | ||
| GB1385895A (en) * | 1971-03-01 | 1975-03-05 | Glaxo Lab Ltd | Antibiotics |
| CA1076560A (en) * | 1972-06-14 | 1980-04-29 | Smith Kline And French Canada Ltd. | 3-heterocyclic thiomethylcephalosporins |
-
1969
- 1969-12-05 ZA ZA698494A patent/ZA698494B/en unknown
- 1969-12-11 IL IL33522A patent/IL33522A0/en unknown
- 1969-12-15 BR BR215176/69A patent/BR6915176D0/en unknown
- 1969-12-24 SU SU1389812A patent/SU383302A3/ru active
- 1969-12-24 BE BE743754D patent/BE743754A/xx unknown
- 1969-12-26 FR FR6945111A patent/FR2032408B1/fr not_active Expired
- 1969-12-26 GT GT196915584A patent/GT196915584A/en unknown
- 1969-12-31 NL NL6919698A patent/NL6919698A/xx unknown
- 1969-12-31 GB GB63526/69A patent/GB1261780A/en not_active Expired
-
1970
- 1970-01-02 DE DE19702000111 patent/DE2000111A1/en active Pending
- 1970-01-02 PL PL1970137933A patent/PL80818B1/pl unknown
- 1970-01-06 RO RO62053A patent/RO56960A/ro unknown
- 1970-01-07 DO DO1970001696A patent/DOP1970001696A/en unknown
- 1970-01-07 CH CH10970A patent/CH536321A/en not_active IP Right Cessation
- 1970-01-07 AT AT11670A patent/AT296501B/en not_active IP Right Cessation
- 1970-01-07 ES ES375237A patent/ES375237A1/en not_active Expired
- 1970-01-07 LU LU60150D patent/LU60150A1/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409215A (en) | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
| US4462999A (en) * | 1979-11-19 | 1984-07-31 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
| US5594132A (en) * | 1979-11-19 | 1997-01-14 | Fujisawa Pharmaceutical Co., Ltd. | 7-acylamino-3-substituted cephalosporanic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| RO56960A (en) | 1974-11-11 |
| GT196915584A (en) | 1971-06-19 |
| SU383302A3 (en) | 1973-05-25 |
| BR6915176D0 (en) | 1973-02-13 |
| FR2032408A1 (en) | 1970-11-27 |
| CH536321A (en) | 1973-04-30 |
| AT296501B (en) | 1972-02-25 |
| PL80818B1 (en) | 1975-08-30 |
| FR2032408B1 (en) | 1974-02-01 |
| BE743754A (en) | 1970-06-24 |
| DOP1970001696A (en) | 1974-12-09 |
| DE2000111A1 (en) | 1970-09-10 |
| ZA698494B (en) | 1971-07-28 |
| LU60150A1 (en) | 1970-07-09 |
| ES375237A1 (en) | 1972-03-16 |
| NL6919698A (en) | 1970-08-28 |
| IL33522A0 (en) | 1970-02-19 |
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