FI81803B - Foerfarande foer framstaellning av terapeutiskt anvaendbara 6-(1-hydroxietyl)-7-oxo-3-(1-metyl-4- tiatetrahydrotiopyranium)-1-azabicyklo/3.2.0/hept-2-en-2- karboxylsyraderivat. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 6-(1-hydroxietyl)-7-oxo-3-(1-metyl-4- tiatetrahydrotiopyranium)-1-azabicyklo/3.2.0/hept-2-en-2- karboxylsyraderivat. Download PDFInfo
- Publication number
- FI81803B FI81803B FI863609A FI863609A FI81803B FI 81803 B FI81803 B FI 81803B FI 863609 A FI863609 A FI 863609A FI 863609 A FI863609 A FI 863609A FI 81803 B FI81803 B FI 81803B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- methyl
- compound
- defined above
- protecting group
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
-
- 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
-
- 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
Landscapes
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (3)
1. Förfarande för framställning av terapeutiskt användbara 6-(1-hydroxietyl)-7-oxo-3-(l-metyl-4-tiatetra-5 hydrotiopyraniura) - 1-azabicyklo [3.2.0]hept-2-en-2-karboxy1 - syraderivat och farmaceutiskt godtagbara salter därav, OH B ^prV s -0*-ch3 io2R2 (I» 15 där R2 är väte, ajonisk laddning eller en fysiologiskt godtagbar estergrupp, och B är väte eller metyl, k ä n -neteckrvat därav, att (a) (1) en mellanprodukt med formeln (lii) 20 OH B A— • (III)
25 Cr“ N ^COOR2' där B är ovan definierad och R2' är en konvetionell lätt 30 avspjälkbar karboxylskyddsgrupp, säsom p-nitrobensyl, om-sätts 1 ett Inert organiskt lösningsmedel med ett reagens, som förmär Införa en konventlonell avgäende grupp L, säsom difenoxifosfinyloxi, i 2-ställning av mellanprodukten (III), varvld erhälls en mellanprodukt med formeln (IV) 36 81 803 OH B Λ-rV
5. I (IV) 0^ N ——L 2 1 ^COOR^ 10 där B och R2' är ovan deflnierade och L är en ovan defini-erad konventionell avgäende grupp; (2) mellanprodukten med formeln (IV) omsätts i ett inert organiskt lösningsmedel och i närvaro av en bas med en tiol med följande formel 15 -O 20 varvid erhälls en mellanprodukt med formeln (II) 25 OH B ,_t -ΥΛγ "O
30 N"-N 2'
0 NCOOR^ där B och R2' är ovan deflnierade; 35 (3) en mellanprodukt med formeln (II) omsätts i ett 37 8 1 8 0 3 inert organiskt lösningsmedel med ett alkyleringsmedel med följande formel H3C-X’ 5 där X' är en konventionell avgäende grupp, säsom halogen eller sulfonatester, varvld bildas en kvaterniserad före-ning med formeln (I'), 10 OH B Λ—rV s Os'CH3 0J^_N -^coor2' 15 där B och R2' Mr ovan definierade; och ifall önskvärt, avlägsnas karboxy1skyddsgruppen R2', 20 varvid erhälls en önskad oskyddad förening med formeln (I) eller ett farmaceutiskt godtagbart salt eller en fysiolo-giskt hydrolyserbar ester därav, eller ifall önskvärt, utförs kvaterniseringssteget efter avlägsnandet av karbo-xylskyddsgruppen R2 ' , eller 25 (b) en mellanprodukt med formeln (IV) OH B A—r^Y"1, 30 1 (IV) -N L 21 ^ ^COOR^ 35 där B och L Mr ovan definierade och R2' Mr en konventio- 38 81 803 neli lätt avspjälkbar karboxylskyddsgrupp, omsätts i ett inert lösningsmedel och i närvaro av en bas med en tiol med följande formel 5 HS —Q*-ch3 10 varvid erhälls en förening med formeln (I') 15 OH B
20 C00R där B och R2' är ovan definierade, och ifall önskvärt, avlägsnas karboxyskyddsgruppen R2 ’ , varvid erhälls en öns-25 kad oskyddad förening med formeln (I) eller ett farmaceu-tiskt godtagbart sait eller en fysiologiskt hydrolyserbar ester därav.
2. Förfarande enligt patentkravet 1, kanne-t e c k n a t därav, att man framställer (5R,6S)-6-(1R- 30 hydroxietyl)-7-oxo-3-(l-metyl-4-tiatetrahydrotiopyranium)- l-azabicyklo[3.2.0]hept-2-en-karboxylat.
3. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer (5R,6S)-6-(1R-hydroxietyl)-4R-metyl-7-oxo-3-(l-metyl-4-tiatetrahydrotio- 35 pyranium)-l-azabicyklo[3.2.0]hept-2-en-2-karboxylat.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77462885 | 1985-09-11 | ||
| US06/774,628 US4665169A (en) | 1985-09-11 | 1985-09-11 | Carbapenem antibiotics |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI863609A0 FI863609A0 (fi) | 1986-09-08 |
| FI863609A FI863609A (fi) | 1987-03-12 |
| FI81803B true FI81803B (fi) | 1990-08-31 |
| FI81803C FI81803C (sv) | 1990-12-10 |
Family
ID=25101800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI863609A FI81803C (sv) | 1985-09-11 | 1986-09-08 | Förfarande för framställning av terapeutiskt användbara 6-(1-hydroxiet yl)-7-oxo-3-(1-metyl-4-tiatetrahydrotiopyranium)-1-azabicyklo/3.2.0/he pt-2-en-2-karboxylsyraderivat |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4665169A (sv) |
| JP (1) | JPS6261980A (sv) |
| KR (1) | KR910006807B1 (sv) |
| CN (1) | CN1015261B (sv) |
| AR (1) | AR242577A1 (sv) |
| AT (1) | AT396472B (sv) |
| AU (1) | AU596990B2 (sv) |
| BE (1) | BE905415A (sv) |
| CH (1) | CH669381A5 (sv) |
| CS (1) | CS259892B2 (sv) |
| DD (1) | DD252605A1 (sv) |
| DE (1) | DE3630857C2 (sv) |
| DK (1) | DK433586A (sv) |
| ES (1) | ES2002303A6 (sv) |
| FI (1) | FI81803C (sv) |
| FR (1) | FR2587704B1 (sv) |
| GB (1) | GB2180238B (sv) |
| GR (1) | GR862313B (sv) |
| HU (1) | HU198491B (sv) |
| IL (1) | IL79969A0 (sv) |
| IT (1) | IT1207578B (sv) |
| LU (1) | LU86575A1 (sv) |
| MY (1) | MY102957A (sv) |
| NL (1) | NL8602282A (sv) |
| NZ (1) | NZ217519A (sv) |
| PT (1) | PT83361B (sv) |
| SE (1) | SE469630B (sv) |
| SU (1) | SU1480764A3 (sv) |
| YU (1) | YU45800B (sv) |
| ZA (1) | ZA866638B (sv) |
| ZW (1) | ZW16186A1 (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5321020A (en) * | 1989-03-28 | 1994-06-14 | Pfizer Inc. | Antibacterial 2-carbapenem derivatives |
| MX20084A (es) * | 1989-03-28 | 1993-03-01 | Pfizer | Derivados de 2 -carbapenem antibacterianos |
| US5602118A (en) * | 1993-03-16 | 1997-02-11 | American Cyanamid Company | 2-thiosubstituted carbapenems |
| RU2714730C1 (ru) | 2019-04-11 | 2020-02-19 | Общество с ограниченной ответственностью "КС-ТЕХНОЛОГИИ" | Конусная инерционная дробилка с опорным подшипником скольжения |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950357A (en) * | 1974-11-25 | 1976-04-13 | Merck & Co., Inc. | Antibiotics |
| US4235920A (en) * | 1975-11-21 | 1980-11-25 | Merck & Co., Inc. | N-Alkylated derivatives of thienamycin |
| AU4061378A (en) * | 1977-10-19 | 1980-04-17 | Merck & Co., Inc. | 1-azabicyclo (3.2.0) hept-2-enes |
| AU531084B2 (en) * | 1977-10-19 | 1983-08-11 | Merck & Co., Inc. | Azetidine derivatives |
| US4232036A (en) * | 1978-10-24 | 1980-11-04 | Merck & Co., Inc. | 6-, 1- and 2-Substituted-1-carbadethiapen-2-em-3-carboxylic acids |
| EP0010317B1 (en) * | 1978-10-24 | 1983-12-21 | Merck & Co. Inc. | 6-, 1- and 2-substituted-1-carbapen-2-em-3-carboxylic acids, processes for the preparation of such compounds and pharmaceutical composition comprising such compounds |
| EP0017992A1 (en) * | 1979-04-19 | 1980-10-29 | Merck & Co. Inc. | 2-Substituted-6-substituted-1-carbadethiapen-2-em-3-carboxylic acids, processes for preparing them, antibiotic pharmaceutical compositions containing same and process for preparing intermediates |
| US4376774A (en) * | 1979-05-29 | 1983-03-15 | Merck & Co., Inc. | Antibiotic N-heterocyclyl thienamycin |
| IE52147B1 (en) * | 1980-03-27 | 1987-07-08 | Merck & Co Inc | 4-(3-carboxy-2-oxopropyl)-azetidin-2-ones and process for their preparation |
| DE3169321D1 (en) * | 1980-03-27 | 1985-04-25 | Merck & Co Inc | Process for the preparation of 1-carbapenems and intermediates via silyl-substituted dithioacetals |
| US4309346A (en) * | 1980-03-27 | 1982-01-05 | Merck & Co., Inc. | Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates |
| EP0038869A1 (en) * | 1980-04-30 | 1981-11-04 | Merck & Co. Inc. | Process for the preparation of 1-carbapenems, and intermediates for their preparation |
| JPS56161393A (en) * | 1980-05-16 | 1981-12-11 | Sanraku Inc | Beta-lactam compound |
| CA1198440A (en) * | 1982-04-08 | 1985-12-24 | Choung U. Kim | Carbapenem antibiotics |
| US4552696A (en) * | 1982-04-09 | 1985-11-12 | Bristol-Myers Company | Carbapenem antibiotics |
| US4536335A (en) * | 1982-06-18 | 1985-08-20 | Bristol-Myers Company | Carbapenem antibiotics |
| FI832619A (fi) * | 1982-07-26 | 1984-01-27 | Sandoz Ag | Fluoralkylerade karbapenemderivat |
| NZ205626A (en) * | 1982-09-28 | 1986-12-05 | Bristol Myers Co | Carbapenem antibiotics |
| DK140584A (da) * | 1983-03-08 | 1984-09-09 | Bristol Myers Co | Fremgangsmaade til fremstilling af carbapenemderivater |
| JPS60202886A (ja) * | 1984-03-27 | 1985-10-14 | Sankyo Co Ltd | １―置換カルバペネム―３―カルボン酸誘導体 |
-
1985
- 1985-09-11 US US06/774,628 patent/US4665169A/en not_active Expired - Fee Related
-
1986
- 1986-08-08 ZW ZW161/86A patent/ZW16186A1/xx unknown
- 1986-08-29 AR AR86305095A patent/AR242577A1/es active
- 1986-09-02 ZA ZA866638A patent/ZA866638B/xx unknown
- 1986-09-04 AU AU62348/86A patent/AU596990B2/en not_active Ceased
- 1986-09-08 IL IL79969A patent/IL79969A0/xx not_active IP Right Cessation
- 1986-09-08 FR FR868612540A patent/FR2587704B1/fr not_active Expired
- 1986-09-08 FI FI863609A patent/FI81803C/sv not_active IP Right Cessation
- 1986-09-09 DD DD86294267A patent/DD252605A1/xx not_active IP Right Cessation
- 1986-09-09 CN CN86105933A patent/CN1015261B/zh not_active Expired
- 1986-09-09 NZ NZ217519A patent/NZ217519A/xx unknown
- 1986-09-10 JP JP61213707A patent/JPS6261980A/ja active Pending
- 1986-09-10 SE SE8603798A patent/SE469630B/sv not_active IP Right Cessation
- 1986-09-10 DE DE3630857A patent/DE3630857C2/de not_active Expired - Fee Related
- 1986-09-10 KR KR1019860007583A patent/KR910006807B1/ko not_active IP Right Cessation
- 1986-09-10 DK DK433586A patent/DK433586A/da not_active Application Discontinuation
- 1986-09-10 IT IT8621666A patent/IT1207578B/it active
- 1986-09-10 NL NL8602282A patent/NL8602282A/nl not_active Application Discontinuation
- 1986-09-10 ES ES8601760A patent/ES2002303A6/es not_active Expired
- 1986-09-10 BE BE0/217150A patent/BE905415A/fr not_active IP Right Cessation
- 1986-09-10 GB GB8621759A patent/GB2180238B/en not_active Expired
- 1986-09-10 CH CH3640/86A patent/CH669381A5/de not_active IP Right Cessation
- 1986-09-10 GR GR862313A patent/GR862313B/el unknown
- 1986-09-10 SU SU864028122A patent/SU1480764A3/ru active
- 1986-09-10 LU LU86575A patent/LU86575A1/fr unknown
- 1986-09-11 CS CS866567A patent/CS259892B2/cs unknown
- 1986-09-11 HU HU863916A patent/HU198491B/hu not_active IP Right Cessation
- 1986-09-11 PT PT83361A patent/PT83361B/pt not_active IP Right Cessation
- 1986-09-11 YU YU158586A patent/YU45800B/sh unknown
- 1986-09-11 AT AT0245286A patent/AT396472B/de not_active IP Right Cessation
-
1987
- 1987-10-01 MY MYPI87002710A patent/MY102957A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR890001426B1 (ko) | 카르바페넴 화합물의 제조방법 | |
| FI86729B (fi) | Foerfarande foer framstaellning av antibiotiskt aktiva (1r,5s,6s)-2- -substituerade tio-6-/(r)-1-hydroxietyl/-1-metyl-karbapenem-3 -karboxylsyraderivat. | |
| IE53047B1 (en) | 2-carbamimidoyl-6-substituted-1-carbadethiapen-2-em-3-carboxylic acids, a process for preparing and an antibiotic composition comprising the same | |
| KR19990064201A (ko) | 세팔로스포린 항생제 | |
| KR880001069B1 (ko) | 카르바페넴 유도체및 그의 제조방법 | |
| KR890002228B1 (ko) | 카르바페넴 유도체 및 그의 제조방법 | |
| FI81803B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 6-(1-hydroxietyl)-7-oxo-3-(1-metyl-4- tiatetrahydrotiopyranium)-1-azabicyklo/3.2.0/hept-2-en-2- karboxylsyraderivat. | |
| JPS60233077A (ja) | １‐テヘロ‐６‐〔１‐ヒドロキシエチル〕‐２‐ｓｒ↑８‐１‐カルバデチアペン‐２‐エム‐３‐カルボン酸 | |
| IE860918L (en) | Penem compounds | |
| EP0273747B1 (en) | Penem derivatives, production and use thereof | |
| EP0166972B1 (en) | Penem derivatives, methods of producing them, their use and pharmaceutical compositions | |
| EP0235823B1 (en) | Carbapenem antibiotics, a process for preparing them and pharmaceutical compositions containing them | |
| US4076826A (en) | 3-(.beta.-Hydroxyethylidene)-6-(α-Hydroxyethyl)-7-oxo-4-oxaazabicyclo[3.2.0]heptene-2-carboxylic acid and derivatives thereof | |
| US4078067A (en) | 3-(.beta.-Aminoethylidene)-7-oxo-4-oxaazabicyclo[3.2.0]heptane-2-carboxylic acid and derivatives thereof | |
| US4880922A (en) | Carbapenems with quaternized heterothioalkylthio substitution at position 2 | |
| IL101164A (en) | Trotocyclic compounds of carbapenem, their preparation and pharmaceutical preparations containing them | |
| US4840946A (en) | Benzazolythio-carbapenem antibiotics | |
| KR880001055B1 (ko) | 카르바페넴 유도체의 제조방법 | |
| US4629726A (en) | Penem carboxylic acids | |
| EP0430037A2 (en) | Process for producing 2-carbon-substituted carbapenem derivatives | |
| KR910009270B1 (ko) | 카바펜엠 항생제의 제조방법 | |
| DE3880660T2 (de) | In 2-stellung substituierte (1r,5s,6s)-2-thio-6-((r)-1-hydroxyethyl)-1-methyl-carbapenem-carbonsaeure-derivate. | |
| EP0544307A1 (en) | Alkylaminoakylpyrrolidinylthiocarbapenem derivatives | |
| WO1995014692A1 (en) | Cabapenem derivatives and processes for preparing the same | |
| US4078068A (en) | 3-(β-Aminoethylidene)-6-(α-hydroxyethyl)-7-oxo-4-oxaazabicyclo[3.]heptane-2-carboxylic acid and derivatives thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: BRISTOL-MYERS SQUIBB COMPANY |