FI82057B - Foerfarande foer framstaellning av en 7beta-(karboxialkenoylamino)-3-cefem-4-karboxylsyrafoerening och dess derivat. - Google Patents
Foerfarande foer framstaellning av en 7beta-(karboxialkenoylamino)-3-cefem-4-karboxylsyrafoerening och dess derivat. Download PDFInfo
- Publication number
- FI82057B FI82057B FI843871A FI843871A FI82057B FI 82057 B FI82057 B FI 82057B FI 843871 A FI843871 A FI 843871A FI 843871 A FI843871 A FI 843871A FI 82057 B FI82057 B FI 82057B
- Authority
- FI
- Finland
- Prior art keywords
- carboxylic acid
- mixture
- acid
- 7beta
- ester
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
Claims (2)
1. Förfarande för tillverkning av en 7beta-(karboxi- alkenoylamino)-3-cefem-4-karboxylsyraförening som är 5 användbar som läkemedel och derivat av denna, vilken förening presenteras med följande formel I: 1. ? 1 Rj-C00R* O00R* där R är en eventuellt skyddad aminotiazolyl eller 1c aminotiadiazolyl, 5 2 .. R ar en lagre alkylen, är en väteatom eller en som läkemedelsderivat lämp-lig bildningsatom eller -grupp eller en bildnings-grupp för en ester, 4 .. 2Q R ar vate, R^ är väte, halogenatom, hydroxi, en lägre alkoxi, en lägre alkansulfonyloxi, en lägre halogenalkyltio, en lägre alkenyltiogrupp,-eller en lägre alkenyl-eller en lägre alkylgrupp, vilken kan vara substi-tuerad med cyano, karboxi, skyddad karboxi, en lägre alkoxikarbonyl, en lägre alkoxi, en lägre alkanoyloxi, karbamoyl, en lägre alkyltio, en lägre cyanoalkyltio, en lägre difluoralkyltio, halogen, pyridino, triazolyltio, tetrazolyltio, en 3Q lägre alkylitetrazolyltio, tiadiazolyltio, en lägre alkylitiadiazolyltio, aminotiadiazolyltio, en skyddad aminotiadiazolyltio, en lägre alkoxi-karbonylaminotiadiazolyltio, en lägre alkoxikarbo-nylaminotetrazolyltio, en lägre aminoalkyltia- 33 diazolyltio eller en lägre skyddad aminoalkyltia- diazolyltio, 94 8 2 0 5 7 är en väteatom eller en som läkemedelsderivat lämp-lig saitbiidnincsatom eller -grupp eller en ester-bildnir.gsgrupp, lämpligen en lägre aralkylgrupp, och
5 X är svavel, kännetecknat av att antingen a) en 7beta-amino-3-cefem-4-karboxylsyra amideras i enlighet med formel II eller dess reaktiva derivat R4 H2N^j---y x ·.
10 J-- N J (II) ° Y^R5 COOR6 med en karboxialkenoylsyra eller dess reaktiva derivat i enlighet med formel III 15 RC = CH-R2- COOR3 (III) i COOH varvid en 7beta-amino-3-cefem-4-karboxylsyra eller dess 20 derivat som motsvarar formel I erhälls, b) 7beta-karboxialkenoylamino-3-(halogen eller sulfonyloxi)-3-cefem-4-karboxylsyra^eller dess reaktiva derivat reduceras med ett reducerande ämne, varvid en 7beta-karboxialkenoylamino-3-ickesubstituerad-3-cefem- 25 4-karboxylsyra eller dess derivat erhälls, c) 7beta-karboxialkenoylamino-3-(halogen eller sulfonyloxi)-3-cefem-4-karboxylsyra eller dess reaktiva derivat utsätts att elimineras medelst en bas eller värme, varvid en mot formeln I motsvarande 7beta- 30 karboxialkenoylamino-3-ickesubstituerad-3-cefem-4- karboxylsyra eller dess derivat erhälls, eller d) 7beta-karboxialkenoylamino-3-(med en avlägs- nande grupp substituerad metyl)-3-cefem-4-karboxylsyra eller dess reaktiva derivat utsätts för en nukleofil 35 reagens, varvid en mot formeln I motsvarande 7beta- karboxialkenoylamino-3-(med en nukleofil grupp substi- 95 82057 tue ramety 1) - r-cef em—4-karboxy Isyra eiler de s s derivat erhalls, ooh om sa onskas avlägsnas karboxi- eiler aminogrup-pens skyddsgrupp ur den erhällna 7beta-karboxialkenoyl-5 amino-3-cefem-4-karboxylsyran eiler dess derivat, denna omvandlas till sitt sait och/eller förestras.
2. Förfarande i enlighet med patentkrav 1, k ä n - ; 2 netecknat av att R är 2-aminotiazol-4-yl, R 10 är metylen, RJ, R^, R^ är väte, R^ är väte, vinyl, cyanovinyl, trifluorpropenyl, acetoximetyl, karbamoyl-metyl eiler tiadiazolyltiometyl och X är svavel.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58186601A JPS6078987A (ja) | 1983-10-04 | 1983-10-04 | アクリルアミドセフアロスポリン類 |
JP18660183 | 1983-10-04 | ||
JP1856384 | 1984-02-03 | ||
JP59018563A JPS60163884A (ja) | 1984-02-03 | 1984-02-03 | カルボキシアルケンアミドセフアロスポリン |
JP59100890A JPH0780892B2 (ja) | 1984-05-18 | 1984-05-18 | カルボキシアルケンアミドセフアロスポリン |
JP10089084 | 1984-05-18 |
Publications (4)
Publication Number | Publication Date |
---|---|
FI843871A0 FI843871A0 (fi) | 1984-10-02 |
FI843871L FI843871L (fi) | 1985-04-05 |
FI82057B true FI82057B (fi) | 1990-09-28 |
FI82057C FI82057C (sv) | 1991-01-10 |
Family
ID=27282263
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI843871A FI82057C (sv) | 1983-10-04 | 1984-10-02 | Förfarande för framställning av en 7beta-(karboxialkenoylamino)-3-cefe m-4-karboxylsyraförening och dess derivat |
Country Status (22)
Country | Link |
---|---|
US (3) | US4634697A (sv) |
EP (1) | EP0136721B1 (sv) |
KR (2) | KR880002376B1 (sv) |
AR (1) | AR242392A1 (sv) |
AT (1) | ATE99311T1 (sv) |
AU (2) | AU575854B2 (sv) |
CA (2) | CA1238910A (sv) |
DE (2) | DE3486259T2 (sv) |
DK (1) | DK171043B1 (sv) |
ES (3) | ES8604602A1 (sv) |
FI (1) | FI82057C (sv) |
GB (3) | GB2154580B (sv) |
GR (1) | GR80544B (sv) |
HU (1) | HU193298B (sv) |
IE (1) | IE57744B1 (sv) |
IL (3) | IL84653A (sv) |
MX (1) | MX174328B (sv) |
NL (1) | NL940013I2 (sv) |
NO (2) | NO173238C (sv) |
NZ (2) | NZ209634A (sv) |
PH (2) | PH20223A (sv) |
PT (1) | PT79287A (sv) |
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GB2076801A (en) * | 1980-04-14 | 1981-12-09 | Erba Farmitalia | alpha , beta -Disubstituted Acrylamido Cephalosporins |
DE3037997A1 (de) * | 1980-10-08 | 1982-05-13 | Bayer Ag | (beta) -lactamantibiotika, verfahren zu deren herstellung sowie sie enthaltende mittel |
DE3145727A1 (de) * | 1981-11-19 | 1983-05-26 | Bayer Ag, 5090 Leverkusen | Zwischenprodukte, verfahren zu deren herstellung und verfahren zur herstellung von cephalosporinen |
CA1201431A (en) * | 1981-12-17 | 1986-03-04 | Daiei Tunemoto | .beta.-LACTAM COMPOUNDS, PROCESS FOR THE PREPARATION THEREOF AND INTERMEDIATE PRODUCTS FOR THE PREPARATION THEREOF |
DE3224866A1 (de) * | 1982-07-02 | 1984-01-05 | Bayer Ag, 5090 Leverkusen | Ss-lactamantibiotika, verfahren zu deren herstellung sowie sie enthaltende mittel |
DE3300593A1 (de) * | 1983-01-11 | 1984-07-12 | Bayer Ag, 5090 Leverkusen | Neue cephalosporine und verfahren zu ihrer herstellung |
AU575854B2 (en) * | 1983-10-04 | 1988-08-11 | Shionogi & Co., Ltd. | 7beta-(carboxyalkenamido) cephalosporins |
-
1984
- 1984-09-19 AU AU33300/84A patent/AU575854B2/en not_active Expired
- 1984-09-21 NZ NZ209634A patent/NZ209634A/xx unknown
- 1984-09-21 NZ NZ218741A patent/NZ218741A/xx unknown
- 1984-09-25 PH PH31265A patent/PH20223A/en unknown
- 1984-09-27 CA CA000464215A patent/CA1238910A/en not_active Expired
- 1984-10-01 PT PT79287A patent/PT79287A/pt unknown
- 1984-10-02 FI FI843871A patent/FI82057C/sv not_active IP Right Cessation
- 1984-10-02 NO NO843956A patent/NO173238C/no not_active IP Right Cessation
- 1984-10-03 IE IE2524/84A patent/IE57744B1/en not_active IP Right Cessation
- 1984-10-03 GR GR80544A patent/GR80544B/el unknown
- 1984-10-03 MX MX013280A patent/MX174328B/es unknown
- 1984-10-03 GB GB08424923A patent/GB2154580B/en not_active Expired
- 1984-10-03 HU HU843743A patent/HU193298B/hu unknown
- 1984-10-03 DK DK474584A patent/DK171043B1/da not_active IP Right Cessation
- 1984-10-04 AT AT84111916T patent/ATE99311T1/de active
- 1984-10-04 IL IL84653A patent/IL84653A/xx not_active IP Right Cessation
- 1984-10-04 DE DE3486259T patent/DE3486259T2/de not_active Expired - Lifetime
- 1984-10-04 IL IL73159A patent/IL73159A/xx not_active IP Right Cessation
- 1984-10-04 AR AR84298181A patent/AR242392A1/es active
- 1984-10-04 EP EP84111916A patent/EP0136721B1/en not_active Expired - Lifetime
- 1984-10-04 DE DE198484111916T patent/DE136721T1/de active Pending
- 1984-10-04 ES ES536502A patent/ES8604602A1/es not_active Expired
- 1984-10-04 KR KR1019840006134A patent/KR880002376B1/ko not_active IP Right Cessation
-
1985
- 1985-03-12 US US06/711,017 patent/US4634697A/en not_active Expired - Lifetime
- 1985-08-29 ES ES547301A patent/ES8605278A1/es not_active Expired
- 1985-08-29 ES ES547300A patent/ES8700222A1/es not_active Expired
- 1985-09-27 NO NO853806A patent/NO176567C/no not_active IP Right Cessation
-
1986
- 1986-02-20 US US06/831,435 patent/US4748170A/en not_active Expired - Lifetime
- 1986-05-27 PH PH33818A patent/PH21766A/en unknown
-
1987
- 1987-01-06 GB GB08700123A patent/GB2190914B/en not_active Expired
- 1987-03-04 CA CA000531176A patent/CA1272713A/en not_active Expired - Lifetime
- 1987-11-13 GB GB08726623A patent/GB2198727B/en not_active Expired
- 1987-11-27 IL IL84653A patent/IL84653A0/xx unknown
- 1987-12-09 US US07/132,882 patent/US4912224A/en not_active Expired - Lifetime
-
1988
- 1988-05-16 AU AU16194/88A patent/AU601842B2/en not_active Expired
- 1988-09-21 KR KR1019880012223A patent/KR880002684B1/ko not_active IP Right Cessation
-
1994
- 1994-07-04 NL NL940013C patent/NL940013I2/nl unknown
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Date | Code | Title | Description |
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ND | Supplementary protection certificate (spc) granted | ||
SPCG | Supplementary protection certificate granted |
Spc suppl protection certif: L68 Extension date: 20070217 |
|
FG | Patent granted |
Owner name: SHIONOGI & CO, LTD |
|
MA | Patent expired |