FI79317B - Foerfarande foer framstaellning av antibiotiskt aktiva karbapenemderivat. - Google Patents
Foerfarande foer framstaellning av antibiotiskt aktiva karbapenemderivat. Download PDFInfo
- Publication number
- FI79317B FI79317B FI853748A FI853748A FI79317B FI 79317 B FI79317 B FI 79317B FI 853748 A FI853748 A FI 853748A FI 853748 A FI853748 A FI 853748A FI 79317 B FI79317 B FI 79317B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- coor
- defined above
- organic solvent
- Prior art date
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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
- 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 (8)
1. Förfarande för framställning av antibiotiskt aktiva karbapenemderivat med formeln I 5 CH-, R10 OK H K | 3 © / I : JL S-CH9CH9- S CH-CH--1 * \„H 3. lI R 1
10. N COOR2 o väri R2 är väte, en anjonisk laddning eller en konventio-neli karboxylskyddsgrupp, som kan lätt avlägsnas, säsom 15 paranitrobensyl, förutsatt, att dä R2 är väte eller en skyddsgrupp, är ocksä en motanjon närvarande; och den ena av grupperna R10 och R11 är metyl och den andra är klorsubstituerad fenyl, eller R10 och R11 tillsammans med S^, vid vilken de är bundna, betecknar en grupp med 20 formeln Θ/—\ Φ/ I -S 0 eller -S V-/ vJ 25 eller farmaceutiskt godtagbara salter därav, känne-t e c k n a t därav, att a) en förening med formeln II CH- 0H H H I 3 30 chJh_L_|A^ s-ch2ch2-i I l
0. N ^ COOR2 ' 39 7 9 3 1 7 väri R2' är en konventionell karboxylskyddsgrupp soin kan lätt avlägsnas, säsom paranitrobensyl, underkastas en nukleofil substitutionsreaktion i ett inert organiskt lösningsmedel i närvaro av en silverjonkälla med en sul-5 fidförening med formeln ^RlO R11 väri R10 och R11 är som ovan definierats, för utbytning av jodsubstituenten i föreningen med formeln II mot gruppen 10 ©^.R10 ""-R11 varvid man erhäller en förening med formeln I' 15 „ _ T CH, „10 ? h ? I „e CH3CH--S'CH2CH2'SvVr11
0 COOR2' 20 väri X® är en motanjon och R10, R11 och R2' är som ovan definierats, och om sä önskas, avlägsnas karboxylskydds-gruppen R2 * för erhällande av en oskyddad förening med 25 formeln I eller en farmaceutiskt godtagbart sait därav, eller bl) en förening med formeln III CH3 OH H H I 30 | 1 - /V CH-.CH--Γ I i III >—N-2·
0 COOR väri R2' är som ovan definierats, omsätts i ett inert organiskt lösningsmedel med difenylklorfosfat i närvaro av en bas, varvid man erhäller en förening med formeln IV .0 79317
5 CH3 0H H h chJh ltV°P,oc6„5,2 3. ii IV J-N-2' o ^ COOR 10 väri R2' är som ovan definierats; b2) föreningen med formeln IV omsätts i ett inert organiskt lösningsmedel ooh i närvaro av en bas med en 15 merkaptanförening med formeln HS-CH2CH2-OH, varvid man erhäller en förening med formeln V CH3 OH H H , | z I S-CH0CH~-OH
20 CH-CH--KV"
3. V A-N-2 » o COOR 25 väri R2' är som ovan definierats; b3) föreningen med formeln V omsätts i ett organiskt lösningsmedel ooh i närvaro av en bas med metansulfonyl-klorid eller en funktionell acylerande ekvivalent därav, varvid man erhäller en förening med formeln VI 30 CH, OH H h I 3 I r L S-CH-CHo-0S0oCH_ CH^CH--1 3 “ Γ J-N--X 2, 35 0 ^ COOR
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/656,838 US4683301A (en) | 1982-04-08 | 1984-10-02 | Carbapenem antibiotics |
| US65683884 | 1984-10-02 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI853748A0 FI853748A0 (fi) | 1985-09-27 |
| FI853748L FI853748L (fi) | 1986-04-03 |
| FI79317B true FI79317B (fi) | 1989-08-31 |
| FI79317C FI79317C (sv) | 1989-12-11 |
Family
ID=24634788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI853748A FI79317C (sv) | 1984-10-02 | 1985-09-27 | Förfarande för framställning av antibiotiskt aktiva karbapenemderivat |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4683301A (sv) |
| JP (1) | JPS6187682A (sv) |
| KR (1) | KR910009270B1 (sv) |
| AT (1) | AT395151B (sv) |
| AU (1) | AU575432B2 (sv) |
| BE (1) | BE903353A (sv) |
| CA (1) | CA1260945A (sv) |
| CH (1) | CH665640A5 (sv) |
| DE (1) | DE3535196A1 (sv) |
| DK (1) | DK446685A (sv) |
| ES (2) | ES8703880A1 (sv) |
| FI (1) | FI79317C (sv) |
| FR (1) | FR2571054B1 (sv) |
| GB (1) | GB2165247B (sv) |
| GR (1) | GR852336B (sv) |
| HU (1) | HU194240B (sv) |
| IL (1) | IL76539A0 (sv) |
| IT (1) | IT1190396B (sv) |
| LU (1) | LU86105A1 (sv) |
| NL (1) | NL8502681A (sv) |
| OA (1) | OA08113A (sv) |
| PT (1) | PT81236B (sv) |
| SE (1) | SE466202B (sv) |
| ZA (1) | ZA857581B (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4732977A (en) * | 1982-09-28 | 1988-03-22 | Bristol Myers Company | Carbapenem antibiotics |
| US5116833A (en) * | 1990-10-19 | 1992-05-26 | Bristol-Myers Squibb Company | Antibiotic c-3 dithioacetal-substituted carbapenem compounds, compositions, and methods of use thereof |
| AR002507A1 (es) * | 1995-06-28 | 1998-03-25 | Merck & Co Inc | Proceso mejorado para sintetizar intermediarios de carbapenem |
| US5823718A (en) * | 1996-07-25 | 1998-10-20 | Alnet (Proprietary) Limited | Pillar bag |
Family Cites Families (27)
| 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 |
| US4218463A (en) * | 1977-12-28 | 1980-08-19 | Merck & Co., Inc. | 3-Substituted thio-6-amido-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| US4174316A (en) * | 1978-08-14 | 1979-11-13 | Merck & Co., Inc. | 4-Iodomethylazetidin-2-one |
| US4208422A (en) * | 1978-10-24 | 1980-06-17 | Merck & Co., Inc. | 1-Substituted-pen-2-em-3-carboxylic acids |
| US4232036A (en) * | 1978-10-24 | 1980-11-04 | Merck & Co., Inc. | 6-, 1- and 2-Substituted-1-carbadethiapen-2-em-3-carboxylic acids |
| DK446179A (da) * | 1978-10-24 | 1980-05-29 | Merck & Co Inc | Fremgangsmaade til fremstilling af substituerede 1-carbadethiapen-2-em-3-carboxylsyrer |
| US4318912A (en) * | 1979-01-02 | 1982-03-09 | Merck & Co., Inc. | 6-(1-Hydroxyethyl)-3-substituted-1-azabicyclo(3.2.0)-hept-2-en-7-one-2-carboxylic acid |
| DK165280A (da) * | 1979-04-19 | 1980-10-20 | Merck & Co Inc | Fremgangsmaade til fremstilling af 2- og 6-substituerede 1-carbadethiapen-2-em-3-carboxylsyrer og mellemprodukter til brug ved udoevelse af fremgangsmaaden |
| US4376774A (en) * | 1979-05-29 | 1983-03-15 | Merck & Co., Inc. | Antibiotic N-heterocyclyl thienamycin |
| EP0024832B1 (en) * | 1979-08-10 | 1985-03-13 | Beecham Group Plc | Beta-lactam antibiotics, their preparation, pharmaceutical compositions containing them and their preparation |
| US4309346A (en) * | 1980-03-27 | 1982-01-05 | Merck & Co., Inc. | Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates |
| IE52147B1 (en) * | 1980-03-27 | 1987-07-08 | Merck & Co Inc | 4-(3-carboxy-2-oxopropyl)-azetidin-2-ones and process for their preparation |
| EP0037082B1 (en) * | 1980-03-27 | 1985-03-20 | Merck & Co. Inc. | Process for the preparation of 1-carbapenems and intermediates via silyl-substituted dithioacetals |
| 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 |
| US4378315A (en) * | 1980-05-29 | 1983-03-29 | Merck & Co., Inc. | Process for the preparation of thienamycin and intermediates |
| US4350631A (en) * | 1980-12-18 | 1982-09-21 | Merck & Co., Inc. | 6- and 4-Substituted-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylates |
| ES8404184A1 (es) * | 1981-08-03 | 1984-04-16 | Merck & Co Inc | Un procedimiento para la prepracion de nuevos derivados de acidos 2-carbamimidoil-1-,carbadestiapen-2-en-3-carboxilados. |
| EP0074599A1 (en) * | 1981-09-09 | 1983-03-23 | Takeda Chemical Industries, Ltd. | 5,6-cis-Carbapenem derivatives, their production and use |
| US4640915A (en) * | 1982-03-29 | 1987-02-03 | Fujisawa Pharmaceutical Co., Ltd. | 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid derivatives |
| CA1198440A (en) * | 1982-04-08 | 1985-12-24 | Choung U. Kim | Carbapenem antibiotics |
| US4536335A (en) * | 1982-06-18 | 1985-08-20 | Bristol-Myers Company | Carbapenem antibiotics |
| EP0113101A1 (en) * | 1982-12-30 | 1984-07-11 | Merck & Co. Inc. | 6-(1-Hydroxyethyl)-2-SR8-1-methyl-1-carbadethiapen-2-em-3-carboxylic acid esters |
| DK140584A (da) * | 1983-03-08 | 1984-09-09 | Bristol Myers Co | Fremgangsmaade til fremstilling af carbapenemderivater |
-
1984
- 1984-10-02 US US06/656,838 patent/US4683301A/en not_active Expired - Fee Related
-
1985
- 1985-09-18 CA CA000491072A patent/CA1260945A/en not_active Expired
- 1985-09-25 GR GR852336A patent/GR852336B/el unknown
- 1985-09-27 FI FI853748A patent/FI79317C/sv not_active IP Right Cessation
- 1985-09-28 KR KR1019850007200A patent/KR910009270B1/ko not_active IP Right Cessation
- 1985-09-30 AU AU48102/85A patent/AU575432B2/en not_active Ceased
- 1985-09-30 FR FR8514442A patent/FR2571054B1/fr not_active Expired
- 1985-09-30 ES ES547438A patent/ES8703880A1/es not_active Expired
- 1985-10-01 BE BE0/215665A patent/BE903353A/fr not_active IP Right Cessation
- 1985-10-01 NL NL8502681A patent/NL8502681A/nl not_active Application Discontinuation
- 1985-10-01 IT IT22317/85A patent/IT1190396B/it active
- 1985-10-01 HU HU853808A patent/HU194240B/hu not_active IP Right Cessation
- 1985-10-01 CH CH4235/85A patent/CH665640A5/de not_active IP Right Cessation
- 1985-10-01 GB GB08524125A patent/GB2165247B/en not_active Expired
- 1985-10-01 JP JP60219030A patent/JPS6187682A/ja active Pending
- 1985-10-01 IL IL76539A patent/IL76539A0/xx not_active IP Right Cessation
- 1985-10-01 SE SE8504538A patent/SE466202B/sv not_active IP Right Cessation
- 1985-10-01 DK DK446685A patent/DK446685A/da not_active Application Discontinuation
- 1985-10-01 ZA ZA857581A patent/ZA857581B/xx unknown
- 1985-10-01 LU LU86105A patent/LU86105A1/fr unknown
- 1985-10-02 OA OA58695A patent/OA08113A/xx unknown
- 1985-10-02 PT PT81236A patent/PT81236B/pt not_active IP Right Cessation
- 1985-10-02 DE DE19853535196 patent/DE3535196A1/de not_active Ceased
- 1985-10-02 AT AT0284985A patent/AT395151B/de not_active IP Right Cessation
-
1986
- 1986-04-01 ES ES553605A patent/ES8800223A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: BRISTOL-MYERS CO |