FI74973C - Förfarande för framställning av terapeutiskt aktiva 3-/(1-metyl-1-pyrr olidinium)metyl/-3-cefem-4-karboxylatderivat. - Google Patents
Förfarande för framställning av terapeutiskt aktiva 3-/(1-metyl-1-pyrr olidinium)metyl/-3-cefem-4-karboxylatderivat. Download PDFInfo
- Publication number
- FI74973C FI74973C FI830689A FI830689A FI74973C FI 74973 C FI74973 C FI 74973C FI 830689 A FI830689 A FI 830689A FI 830689 A FI830689 A FI 830689A FI 74973 C FI74973 C FI 74973C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- carboxylate
- pyrrolidinium
- cephem
- compound
- Prior art date
Links
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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (3)
1. Förfarande för framställning av terapeutiskt aktiva 3-^( 1-metyl-l-pyrrolidinium)metyl7-3-cefem-4-5 karboxylatderivat med formeln ./yirPX;- o 10 too© W ch3 i 2 väri R är en lägre alkyl, lägre karboxialkyl eller allyl, eller ogiftiga farinaceutiskt godtagbara salter och soivat därav, kännetecknat därav, att en förening med 15 formeln 0 I / s. N -r— C- C — NH -I-r > b2hn^.s3 \or2, ch2i xiv COOR1 20 2 1 väri R är en lägre alkyl, allyl eller en med en konven-tionell karboxylskyddande grupp skyddad lägre karboxialkyl, B^ är en konventionell karboxylskyddande grupp och B2 är en konventionell aminoskyddande grupp, omsätts med N-metyl-25 pyrrolidin för framställning av en förening med formeln O N—τ— C — C -NH—-\ τβ 2 jCY \ JXi JL B2HN^S^ \nR2' (Γ 30 0R loos' 2/V-> XV ch3 21 1 2 väri RÄ , B och B4 är ovan definierade och samtliga skydds grupper avlägsnas därefter pä konventionellt sätt och om s& önskas, omvandlas den erhällna föreningen tili ett 35 ogiftigt sait eller soivat därav. 43 7 4 9 7 3
2. Förfarande enligt patentkravet 1 för framställ-ning av 7-£2-(2-aminotiazol-4-yl)-(Z)-2-(2-karboxiprop-2-oxiimino) acetamido7-3-Z"(l-nietyl-l-pyrrolidinium) metyl7-3-cefem-4-karboxylat eller ett ogiftigt farmaceutiskt god- 5 tagbart sait eller soivat därav, kännetecknat därav, att benshydryl-7-7T( Z)-2-(2-t-butoxikarbonylprop-2-oxiimino)-2-(2-tritylaminotiazol-4-yl)acetamido7-3-jodmetyl- 3-cefem-4-karboxylat omsätts med N-metylpyrrolidin i ett organiskt lösningsmedel, skyddsgrupperna avlägsnas frän den 10 erhällna föreningen och, om sä önskas, omvandlas den erhäll-na föreningen tili ett ogiftigt farmaceutiskt godtagbart sait eller soivat därav.
3. Förfarande enligt patentkravet 1 för framställning av föreningar med formeln I 15 0 N-r-C—£ -CH-1-f S ^ h2n co° ch3 ^ 20 väri R2 är metyl, etyl, isopropyl eller allyl, eller ogif-tiga farmaceutiskt godtagbara salter eller solvater därav. kännetecknat därav, att benshydryl-7-£"( Z)-2-(metoxi-, etoxi-, 2-propoxi- eller allyl)imino-2-(2-trityl-25 aminotiazol-4-yl)acetamido7-3-jodmetyl-3-cefem-4-karboxylat omsätts med ett jodsalt för erhällande av motsvarande 3-jodmetylderivat varefter det nämnda 3-jodmetylderivatet omsätts med N-metylpyrrolidin i ett organiskt lösningsmedel eller en blandning av organiska lösningsmedel för erhällan-30 de av motsvarande pyrrolidiniumderivat och slutligen avlägsnas skyddsgrupperna frän det nämnda pyrrolidiniumde-rivatet för erhällande av 7-/~(Z)-2-metoxiimino-2-(2-amino-tiazol-4-yl)acetamido7-3-^(l-metyl-l-pyrrolidinium)metyl7- 3- cefem-4-karboxylat, 7-£(Z)-2-etoxiimino-2-(2-aminotiazol- 35 4-yl) acetamido7-3-^(l-metyl-l-pyrrolidinium)metyl7-3-cefeTn- 4- karboxylat, 7-^(Z)-2-(2-propoxiimino)-2-(2-aminotiazol-
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35485182 | 1982-03-04 | ||
| US06/354,851 US4406899A (en) | 1982-03-04 | 1982-03-04 | Cephalosporins |
| US35753482A | 1982-03-12 | 1982-03-12 | |
| US35753482 | 1982-03-12 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI830689A0 FI830689A0 (fi) | 1983-03-01 |
| FI830689L FI830689L (fi) | 1983-09-05 |
| FI74973B FI74973B (fi) | 1987-12-31 |
| FI74973C true FI74973C (sv) | 1988-04-11 |
Family
ID=26998584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI830689A FI74973C (sv) | 1982-03-04 | 1983-03-01 | Förfarande för framställning av terapeutiskt aktiva 3-/(1-metyl-1-pyrr olidinium)metyl/-3-cefem-4-karboxylatderivat. |
Country Status (29)
| Country | Link |
|---|---|
| KR (1) | KR870001986B1 (sv) |
| AT (2) | AT382155B (sv) |
| AU (1) | AU562776B2 (sv) |
| BE (1) | BE896086A (sv) |
| CA (1) | CA1213882A (sv) |
| CH (1) | CH654313A5 (sv) |
| CS (1) | CS249512B2 (sv) |
| DD (1) | DD210280A5 (sv) |
| DE (1) | DE3307550A1 (sv) |
| DK (1) | DK156900C (sv) |
| EG (1) | EG15934A (sv) |
| ES (2) | ES8403919A1 (sv) |
| FI (1) | FI74973C (sv) |
| FR (1) | FR2522659B1 (sv) |
| GB (1) | GB2116180B (sv) |
| GR (1) | GR77916B (sv) |
| HU (1) | HU193158B (sv) |
| IE (1) | IE56647B1 (sv) |
| IL (1) | IL68011A0 (sv) |
| IT (1) | IT1170307B (sv) |
| LU (1) | LU84674A1 (sv) |
| MY (1) | MY8700943A (sv) |
| NL (2) | NL193284C (sv) |
| NZ (1) | NZ203312A (sv) |
| PH (1) | PH18002A (sv) |
| PT (1) | PT76330B (sv) |
| SE (1) | SE453091B (sv) |
| SU (1) | SU1250173A3 (sv) |
| YU (2) | YU43822B (sv) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3409431A1 (de) * | 1983-10-08 | 1985-04-18 | Hoechst Ag, 6230 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| DE3404906A1 (de) * | 1984-02-11 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | 1-oxadethiacephalosporinderivate sowie verfahren zu ihrer herstellung |
| DE3419013A1 (de) * | 1984-05-22 | 1985-11-28 | Bayer Ag, 5090 Leverkusen | Neue cephalosporine und verfahren zu ihrer herstellung |
| GB8424692D0 (en) * | 1984-10-01 | 1984-11-07 | Glaxo Group Ltd | Chemical compounds |
| US4698336A (en) * | 1985-01-30 | 1987-10-06 | Eisai Co., Ltd. | 3-(pyrrolidinio)methyl-3-cephem derivatives |
| CA1284994C (en) * | 1985-08-05 | 1991-06-18 | Murray Arthur Kaplan | Cephalosporin salts and injectable compositions |
| US4910301A (en) * | 1985-08-05 | 1990-03-20 | Bristol-Myers Company | Cefepime cephalosporin salts |
| US4808617A (en) * | 1985-12-18 | 1989-02-28 | Bristol-Myers Company | Lyophilized or precipitated cephalosporin zwitterion and salt combination |
| DE3789466T2 (de) * | 1986-03-17 | 1994-07-28 | Fujisawa Pharmaceutical Co | 3,7-Disubstituierte-3-Cephemverbindungen und Verfahren zu ihrer Herstellung. |
| CA2011116C (en) * | 1989-03-06 | 1999-11-16 | Murray A. Kaplan | Lyophilized bmy-28142 dihydrochloride for parenteral use |
| PT503453E (pt) | 1991-03-08 | 2001-10-31 | Biochemie Gmbh | Novo processo para a producao de cefalosporinas e novos intermeiarios neste processo |
| MY108872A (en) * | 1991-09-10 | 1996-11-30 | Bristol Myers Squibb Co | Preparation of a cephalosporin antibiotic using the syn-isomer of a thiazolyl intermediate. |
| YU81692A (sh) * | 1991-09-10 | 1995-03-27 | Bristol-Myers Co. | Postupak za proizvodnju cefalosporinskog antibiotika |
| US5523400A (en) * | 1993-04-16 | 1996-06-04 | Hoffmann-La Roche Inc. | Cephalosporin antibiotics |
| EP1699804B1 (en) * | 2003-12-23 | 2008-02-06 | Sandoz Gmbh | Process for production of intermediates for use in cefalosporin synthesis |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2760484C2 (sv) * | 1976-04-14 | 1992-12-03 | Takeda Chemical Industries, Ltd., Osaka, Jp | |
| GB1591439A (en) * | 1976-10-01 | 1981-06-24 | Glaxo Operations Ltd | 7-syn (oxyimino -acylamido) cephalosporins |
| AR229883A1 (es) * | 1978-05-26 | 1983-12-30 | Glaxo Group Ltd | Procedimiento para la preparacion de antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)-acetamido)-3-(1-piridinometil)-cef-3-em-4-carboxilato |
| NL7907881A (nl) * | 1978-10-27 | 1980-04-29 | Glaxo Group Ltd | Nieuwe cefalosporine-antibiotica, werkwijze voor de bereiding daarvan en farmaceutische preparaten die deze bevatten. |
| US4443444A (en) * | 1980-08-11 | 1984-04-17 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
-
1983
- 1983-02-02 CA CA000420788A patent/CA1213882A/en not_active Expired
- 1983-02-10 AU AU11304/83A patent/AU562776B2/en not_active Expired
- 1983-02-16 NZ NZ203312A patent/NZ203312A/en unknown
- 1983-02-24 DK DK086283A patent/DK156900C/da not_active IP Right Cessation
- 1983-02-28 CS CS831295A patent/CS249512B2/cs unknown
- 1983-02-28 EG EG136/83A patent/EG15934A/xx active
- 1983-03-01 FR FR8303334A patent/FR2522659B1/fr not_active Expired
- 1983-03-01 IT IT47826/83A patent/IT1170307B/it active
- 1983-03-01 FI FI830689A patent/FI74973C/sv not_active IP Right Cessation
- 1983-03-01 IL IL68011A patent/IL68011A0/xx not_active IP Right Cessation
- 1983-03-01 NL NL8300755A patent/NL193284C/nl not_active IP Right Cessation
- 1983-03-02 ES ES520224A patent/ES8403919A1/es not_active Expired
- 1983-03-02 PH PH28591A patent/PH18002A/en unknown
- 1983-03-02 GR GR70653A patent/GR77916B/el unknown
- 1983-03-03 DE DE19833307550 patent/DE3307550A1/de active Granted
- 1983-03-03 CH CH1170/83A patent/CH654313A5/de not_active IP Right Cessation
- 1983-03-03 GB GB08305940A patent/GB2116180B/en not_active Expired
- 1983-03-03 SU SU833560801A patent/SU1250173A3/ru active
- 1983-03-03 SE SE8301178A patent/SE453091B/sv not_active IP Right Cessation
- 1983-03-03 PT PT76330A patent/PT76330B/pt unknown
- 1983-03-03 DD DD83248457A patent/DD210280A5/de unknown
- 1983-03-03 HU HU83729A patent/HU193158B/hu unknown
- 1983-03-03 IE IE455/83A patent/IE56647B1/en not_active IP Right Cessation
- 1983-03-04 YU YU523/83A patent/YU43822B/xx unknown
- 1983-03-04 AT AT0076183A patent/AT382155B/de not_active IP Right Cessation
- 1983-03-04 LU LU84674A patent/LU84674A1/fr unknown
- 1983-03-04 BE BE0/210263A patent/BE896086A/fr not_active IP Right Cessation
- 1983-03-04 KR KR1019830000871A patent/KR870001986B1/ko not_active IP Right Cessation
- 1983-10-11 ES ES526397A patent/ES8507557A1/es not_active Expired
-
1985
- 1985-08-02 AT AT0228285A patent/AT384612B/de not_active IP Right Cessation
- 1985-09-23 YU YU1496/85A patent/YU44777B/xx unknown
-
1987
- 1987-12-30 MY MY943/87A patent/MY8700943A/xx unknown
-
1999
- 1999-11-05 NL NL990039C patent/NL990039I2/nl unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4406899A (en) | Cephalosporins | |
| US4525473A (en) | Cephalosporins | |
| FI66618C (fi) | Foerfarande foer framstaellning av terapeutiskt verkande 7-(2-(2-aminotiazol-4-yl)-2-(syn)-metoxi-iminoacetamido-cefalosporinderivat | |
| FI74973C (sv) | Förfarande för framställning av terapeutiskt aktiva 3-/(1-metyl-1-pyrr olidinium)metyl/-3-cefem-4-karboxylatderivat. | |
| US4457929A (en) | 3-Quaternary ammonium methyl)-substituted cephalosporin derivatives | |
| US4520022A (en) | Substituted vinyl cephalosporins | |
| US4500526A (en) | Cephalosporin derivatives | |
| KR830000835B1 (ko) | 세팔로스포린 항생제의 제조방법 | |
| FI74972C (sv) | Förfarande för framställning av farmaceutiskt värdefull 7 -/(Z)-2-(2-a minotiazol/-4-yl)-2-oxi-imino-acetamido/-3-cefem-4-karboxylsyra. | |
| US4138555A (en) | (6R,7R)-7-[2-aryl-2-(etherified oximino)acetamido]-3-carbamoyloxymethylceph-3-em-4-carboxylic acid 1-oxides | |
| FI85487B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3- propenylaminotiazolylcefalosporansyror och estrar. | |
| US4971962A (en) | Cephalosporin compounds | |
| US5043334A (en) | Cephalosporin antibiotics | |
| EP0097961B1 (en) | Cephalosporin derivatives, a process for the manufacture thereof and pharmaceutical compositions containing said derivatives | |
| US4661590A (en) | Substituted vinyl cephalosporins | |
| US4874856A (en) | 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof | |
| US4507487A (en) | Chemical compounds | |
| US4394503A (en) | Cephalosporin derivatives | |
| US4560683A (en) | Cephalosporin antibiotics | |
| US4179502A (en) | 7[2-Hydroxyiminoacetamido]cephalosporins | |
| US4474954A (en) | Intermediates for cephalosporin derivatives | |
| CA2057777A1 (en) | Cephalosporin derivatives | |
| JPH04112891A (ja) | 新規オキシム誘導体及び該誘導体を含有する抗菌剤 | |
| GB2168972A (en) | Cephalosporin antibiotics | |
| JPS61134391A (ja) | 新規セフアロスポリン化合物及びそれを有効成分とする抗菌剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ND | Supplementary protection certificate (spc) granted | ||
| SPCG | Supplementary protection certificate granted |
Spc suppl protection certif: L31 Extension date: 20080301 |
|
| MA | Patent expired |
Owner name: BRISTOL-MYERS CO |