FI89715B - Foerfarande foer framstaellning av cefalosporinderivat med foerbaettrade foermakokinetiska egenskaper - Google Patents
Foerfarande foer framstaellning av cefalosporinderivat med foerbaettrade foermakokinetiska egenskaper Download PDFInfo
- Publication number
- FI89715B FI89715B FI884614A FI884614A FI89715B FI 89715 B FI89715 B FI 89715B FI 884614 A FI884614 A FI 884614A FI 884614 A FI884614 A FI 884614A FI 89715 B FI89715 B FI 89715B
- Authority
- FI
- Finland
- Prior art keywords
- group
- compound
- groups
- formula
- salt
- Prior art date
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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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/31—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
- C07C311/32—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Claims (5)
1. Förfarande för framställning av cefalosporinde-rivat med den allmänna formeln (I) och farmaceutiskt god-5 tagbara salter och inre salter samt estrar därav, H2N~Ö 10 \ - C - NH--_/ N\ *i J-n —ch2oco—U 7—A °-C-r2 I \=/ * COOH R3 (I) 15 där I*!, R2 och R3 var och en betecknar en väteatom, eller Rx och R2 bäda betecknar en väteatom eller en metyl-grupp och R3 är en karboxylgrupp, 20. tvä A-grupper är olika; den ena är en OH-grupp och den andra betecknar en grupp -NHS02-Alk-NH2, där Alk betecknar en lägre alkylengrupp med 2-4 kolatomer, k ä n-netecknat därav, att - en förening, som har formeln 25 ' - “Ή , C - C - NH-- f1 cf-K-ss*—ch2i 1 O-C-R’3 X R, COOtBu 35 .· ; ,- '· Γ-f Λ · 2 4 ? .? / ί b där R3 och R2 betecknar samma som ovan, R3' är väte eller en lätt labil ester, och Tr betecknar en aminoskyddsgrupp, bringas att reagera i en lösning, i ett aprotiskt polärt lösningsmedel med en syra, som har formeln (2), eller ett 5 reaktivt derivat därav, A' A'-^-COOH 2 10 där tvä A'-grupper är olika, och av vilka den ena betecknar en hydroxylgrupp och den andra gruppen -NH-S02-Alk-NH2, där Alk betecknar samma som ovan och den aminerade gruppen 15 är skyddad med en labil grupp, - skyddsgrupperna i amino- och karboxylgrupperna elimineras medelst hydrolysering i en stark syra, - den sä erhällna föreningen (I) isoleras som sait, vilket är blldat med de aminerade grupperna närvarande i 20 molekylen, - detta salt eventuellt omvandlas tili ett inre sait eller ett annat, med den aminerade gruppen bildat sait, - föreningen med formeln I eventuellt isoleras av-25 gäende frän motsvarande aminsalt i form av en bas, och denna eventuellt enligt kända metoder omvandlas tili ett sait eller en ester med en eller tvä karboxylgrupper närvarande i molekylen.
2. Förfarande enligt patentkravet 1, k ä n n e -30 tecknat därav, att reagenset med formeln 1 är en syn-isomer.
3. Förfarande enligt patentkravet 2, känne-tecknat därav, att 3-hydroxi-4-[2-(bensyloxikarbo-nylaminoetyl )sulfonamido]bensoesyra omsätts med en syn- 35 isomer av tert.-butyl-7-[2-(2-tritylaminotiazol-4-yl)-2- 25 (, ' r7 < ' / ib metoxiimino-acetamido]-3-jodmetyl-3-cefemkarboxylat, - skyddsgrupperna i amino- och karboxylgrupperna elimineras medelst hydrolysering i en stark syra, och - den sä erhällna föreningen (I) isoleras i en öns-5 kad form.
4. Förfarande enligt nägot av patentkraven 1-3, kännetecknat därav, att som reagens används en förening med formeln
10 B’—cooH B' där tvä B’-grupper är olika och av vilka den ena betecknar 15 en OH-grupp, och den andra en grupp X-NH-Alk-S02-NH-, där X betecknar väte eller en skyddsgrupp för aminogruppen, och Alk betecknar en lägre alkylengrupp med 2-4 kolato-mer. 20
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8713925A FR2621589B1 (fr) | 1987-10-08 | 1987-10-08 | Derives des cephalosporines a pharmacocinetique amelioree, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR8713925 | 1987-10-08 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI884614A0 FI884614A0 (fi) | 1988-10-07 |
| FI884614A FI884614A (fi) | 1989-04-09 |
| FI89715B true FI89715B (fi) | 1993-07-30 |
| FI89715C FI89715C (sv) | 1993-11-10 |
Family
ID=9355637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI884614A FI89715C (sv) | 1987-10-08 | 1988-10-07 | Förfarande för framställning av cefalosporinderivat med förbättrade fö rmakokinetiska egenskaper |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5079241A (sv) |
| EP (1) | EP0311521B1 (sv) |
| JP (1) | JPH0637502B2 (sv) |
| KR (1) | KR970004044B1 (sv) |
| AR (1) | AR246271A1 (sv) |
| AT (1) | ATE74607T1 (sv) |
| AU (2) | AU612414B2 (sv) |
| DE (1) | DE3869895D1 (sv) |
| DK (1) | DK555288A (sv) |
| ES (1) | ES2036702T3 (sv) |
| FI (1) | FI89715C (sv) |
| FR (1) | FR2621589B1 (sv) |
| GR (1) | GR3005122T3 (sv) |
| IE (1) | IE61508B1 (sv) |
| IL (2) | IL103721A (sv) |
| NO (1) | NO171275C (sv) |
| NZ (1) | NZ226487A (sv) |
| PT (1) | PT88694B (sv) |
| ZA (1) | ZA887546B (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4282699B2 (ja) | 2006-09-01 | 2009-06-24 | 株式会社東芝 | 半導体装置 |
| WO2015035376A2 (en) | 2013-09-09 | 2015-03-12 | Calixa Therapeutics, Inc. | Treating infections with ceftolozane/tazobactam in subjects having impaired renal function |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024133A (en) * | 1971-05-14 | 1977-05-17 | Glaxo Laboratories Limited | 7β-[2-Etherified oximino-2-(thienyl-,furyl- or pyridylacetamido)]cephalosporins |
| US3971778A (en) * | 1972-05-12 | 1976-07-27 | Glaxo Laboratories Limited | Cephalosporins having (α-etherified oximino)acylamido groups at the 7-position |
| US4033950A (en) * | 1971-05-14 | 1977-07-05 | Glaxo Laboratories Limited | 3-Hydroxymethyl-7β-(2-alkoxy-or benzyloxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof |
| US4138555A (en) * | 1971-05-14 | 1979-02-06 | Glaxo Laboratories, Limited | (6R,7R)-7-[2-aryl-2-(etherified oximino)acetamido]-3-carbamoyloxymethylceph-3-em-4-carboxylic acid 1-oxides |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US4203899A (en) * | 1974-12-19 | 1980-05-20 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| JPS5760345B2 (sv) * | 1974-12-19 | 1982-12-18 | Takeda Chemical Industries Ltd | |
| US4668783A (en) * | 1974-12-19 | 1987-05-26 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido cephalosporin compounds |
| US4298606A (en) * | 1974-12-19 | 1981-11-03 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| US4166115A (en) * | 1976-04-12 | 1979-08-28 | Fujisawa Pharmaceutical Co., Ltd. | Syn 7-oxoimino substituted derivatives of cephalosporanic acid |
| US4871860A (en) * | 1976-04-12 | 1989-10-03 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3,7-disubstituted-3-cephem-4-caroxylic acid compounds and processes for the preparation thereof |
| US4493833A (en) * | 1976-04-12 | 1985-01-15 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds |
| US4304770A (en) * | 1976-04-12 | 1981-12-08 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
| US4331664A (en) * | 1976-04-12 | 1982-05-25 | Fujisawa Pharmaceutical Co., Ltd. | Syn isomer of 7-[2-cyclo(lower) alkoxyimino-2-(2-amino-or substituted aminothiazol-4-yl)acetamido]-3-lower alkanoyloxymethyl or heterocyclicthiomethyl-3-cephem-4-carboxylic acid compounds |
| US4804752A (en) * | 1976-04-12 | 1989-02-14 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
| US4364943A (en) * | 1976-04-12 | 1982-12-21 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 7-[2-alkoxyimino-2-(2-amino-alkanoylamino-or haloalkanoylamino-thiazol-4-yl) acetamids]-3-[hexanoyl-, or phenylalkanoyl-oxymethyl or benzothiazolylthiomethyl]-3-cephem-4-carboxylic acid |
| DE2760484C2 (sv) * | 1976-04-14 | 1992-12-03 | Takeda Chemical Industries, Ltd., Osaka, Jp | |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| US4655166A (en) * | 1979-12-26 | 1987-04-07 | Hitachi, Ltd. | Apparatus for preventing oscillation of running strip |
| FR2546520B1 (fr) * | 1983-05-27 | 1985-08-30 | Sanofi Sa | Nouveaux composes antibiotiques derives des cephalosporines |
| FR2570702B1 (fr) * | 1984-09-27 | 1987-01-09 | Sanofi Sa | Derives des cephalosporines, procedes d'obtention et leur application a titre d'antibiotiques |
| ZA877987B (en) * | 1986-11-12 | 1988-08-31 | Ici Pharma | Antibiotic compounds |
| FR2607135B1 (fr) * | 1986-11-20 | 1989-04-28 | Sanofi Sa | Nouveaux derives des cephalosporines a pharmacocinetique amelioree, procede pour leur preparation et compositions pharmaceutiques les contenant |
| ZA884093B (en) * | 1987-06-16 | 1989-04-26 | Hoffmann La Roche | Acyl derivatives |
-
1987
- 1987-10-08 FR FR8713925A patent/FR2621589B1/fr not_active Expired - Fee Related
-
1988
- 1988-10-04 DK DK555288A patent/DK555288A/da not_active Application Discontinuation
- 1988-10-06 NZ NZ226487A patent/NZ226487A/xx unknown
- 1988-10-06 AU AU23495/88A patent/AU612414B2/en not_active Ceased
- 1988-10-06 EP EP88402527A patent/EP0311521B1/fr not_active Expired - Lifetime
- 1988-10-06 ES ES198888402527T patent/ES2036702T3/es not_active Expired - Lifetime
- 1988-10-06 DE DE8888402527T patent/DE3869895D1/de not_active Expired - Fee Related
- 1988-10-06 AT AT88402527T patent/ATE74607T1/de not_active IP Right Cessation
- 1988-10-07 AR AR88312142A patent/AR246271A1/es active
- 1988-10-07 IL IL10372188A patent/IL103721A/en not_active IP Right Cessation
- 1988-10-07 FI FI884614A patent/FI89715C/sv not_active IP Right Cessation
- 1988-10-07 JP JP63253650A patent/JPH0637502B2/ja not_active Expired - Lifetime
- 1988-10-07 PT PT88694A patent/PT88694B/pt not_active IP Right Cessation
- 1988-10-07 IL IL87975A patent/IL87975A/xx not_active IP Right Cessation
- 1988-10-07 ZA ZA887546A patent/ZA887546B/xx unknown
- 1988-10-07 NO NO884486A patent/NO171275C/no unknown
- 1988-10-07 IE IE304688A patent/IE61508B1/en not_active IP Right Cessation
- 1988-10-08 KR KR1019880013177A patent/KR970004044B1/ko active IP Right Grant
-
1989
- 1989-10-13 US US07/420,270 patent/US5079241A/en not_active Expired - Fee Related
-
1991
- 1991-06-28 AU AU79451/91A patent/AU637915B2/en not_active Ceased
-
1992
- 1992-07-08 GR GR920401466T patent/GR3005122T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: SANOFI |