KR840001585A - 티에노 및 푸로피리디늄-치환 세팔로스포린 유도체의 제조방법 - Google Patents
티에노 및 푸로피리디늄-치환 세팔로스포린 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840001585A KR840001585A KR1019820004043A KR820004043A KR840001585A KR 840001585 A KR840001585 A KR 840001585A KR 1019820004043 A KR1019820004043 A KR 1019820004043A KR 820004043 A KR820004043 A KR 820004043A KR 840001585 A KR840001585 A KR 840001585A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- group
- formula
- carboxy
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 229930186147 Cephalosporin Natural products 0.000 title claims description 3
- 229940124587 cephalosporin Drugs 0.000 title claims description 3
- 150000001780 cephalosporins Chemical class 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 6
- -1 hydroxy, amino Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical group C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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)
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
내용 없음
Description
[발명의 명칭
티에노 및 푸로피리디늄-치환 세팔로스포린 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 일반식(Ⅱ)의 화합물을 후술하는 구조식 R1으로 표시하는 티에노 또는 푸로피리딘과 축합시키고, 이어서 R3가 에스테르 보호그룹인 경우에는 그 그룹 및 R치환기에 존재할 수 있는 어떤 보호그룹을 제거하거나; 일반식(Ⅲ)의 화합물, 또는 그의 염 또는 4′-에스테르(R3)를 일반식(Ⅴ)인 산의 활성카복시 유도체로 아실화하고, 일반식(Ⅲ)의 화합물이 에스테르형인 경우에는 R3그룹 및 R-치환기에 존재할 수 있는어떤 아미노 보호그룹을 제거하는 것을 포함하여, 일반식(Ⅰ)의 세팔로스포린 유도체 또는 그의 약학적으로 허용되는 염을 제조하는 방법.상기 식에서, R은 수소 또는 하기 일반식으로 나타내는 아실 그룹이고 :여기서 R′는 다음 구조식으로 나타내는 5- 또는 6-원의 헤테로사이클릭환이며 :R″는 수소, 탄소수 1 내지 4의 알킬, 하기 일반식으로 나타내는 카복시-치환알킬 또는 카복시-치환사이클로알킬그룹이거나[여기서 N은 0 내지 3이며, a 및 b 각각으로는 독립적으로 수소 또는 탄소수 1 내지 3의 알킬이거나, 이들이 부착된 탄소와 함께는 탄소수 3 내지 7의 카보사이클릭환을 이루며; R″′는 하이드록시, 아미노, 탄소수 1 내지 4의 알콕시, 또는 OR0인데, R0는 카복시-보호에스테르 그룹이다. 하기 일반식으로 나타내는 카바모일 그룹이며(여기서 R″″는 탄소수 1 내지 4의 알킬, 페닐 또는 페닐로 치환된 탄소수 1 내지 3의 알킬이다);+R1은 다음 구조식으로 나타내는 티에노피리디늄 그룹 또는다음 구조식으로 나타내는 푸로피리디늄 그룹중에서, 선택된 이환성의 피리디늄 그룹이다.[여기서 헤테로환중 하나 또는 둘 다, 탄소수 1 내지 4의 알킬, 할로겐, 트리플루오로메틸, 카복시, 카바모일, -SO3H 하이드록시, 탄소수 1 내지 4의 알콕시, 아미노, 모노-탄소수 1 내지 4의 알킬아미노, 디-탄소수 1 내지 5의 -알킬아미노, 탄소수 2 내지 4의 알카노일아미노, 아미노설포닐, 시아노, 탄소수 1내지 4이 알콕시카보닐 또는 하기 일반식의 그룹중에서 독립적으로 선택된 하나 또는 두 개의 치환기로 임의 치환된다.(여기서 R5및 R6는 독립적으로 수소 또는 탄소수 1 내지 4의 알킬이다)].
- 제1항에 있어서, R이 다음과 같은 제조방법.(여기서 옥심은 씬-배위를 갖는다).
- 제1 또는 2항에 있어서, 티에노-또는 푸로피리디늄환 중 어느 하나 또는 둘 다 탄소수 1 내지 4의 알킬, 플루오로, 클로로, 브로모, 카복시, 카바모일 또는 탄소수 1-4의 알콕시카보닐그룹 중 선택된 하나 또는 두 개의 치환기로 임의 치환되는 제조방법.
- 제3항에 있어서, 티에노-또는 푸로피리디늄환의 어느 하나 또는 둘 다 카복시로 치환된 제조방법.
- 제4항에 있어서, 씬-7-[2-(2-아미노티아졸-4-일)-2-메톡시아미노아세트아미도]-3-(2-카복시티에노[3, 2-C]피리디늄-5-일메틸)-3-세펨-4-카복실레이트를 제조하는 방법.
- 제1 또는 2항에 있어서,+R1이 비치환된 티에노피리디늄 그룹인 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30035781A | 1981-09-08 | 1981-09-08 | |
| US300357 | 1981-09-08 | ||
| US3406228 | 1982-01-09 | ||
| US34062882A | 1982-01-19 | 1982-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840001585A true KR840001585A (ko) | 1984-05-07 |
Family
ID=26971737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019820004043A KR840001585A (ko) | 1981-09-08 | 1982-09-07 | 티에노 및 푸로피리디늄-치환 세팔로스포린 유도체의 제조방법 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0074268A3 (ko) |
| KR (1) | KR840001585A (ko) |
| CS (1) | CS232735B2 (ko) |
| DD (1) | DD209633A5 (ko) |
| DK (1) | DK399282A (ko) |
| ES (2) | ES8404361A1 (ko) |
| FI (1) | FI823088L (ko) |
| GB (1) | GB2105719A (ko) |
| GR (1) | GR76701B (ko) |
| HU (1) | HU187575B (ko) |
| IL (1) | IL66726A0 (ko) |
| NZ (1) | NZ201833A (ko) |
| PH (1) | PH19756A (ko) |
| PL (1) | PL238158A1 (ko) |
| PT (1) | PT75518B (ko) |
| RO (1) | RO84456B (ko) |
| SU (1) | SU1169542A3 (ko) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE30724T1 (de) * | 1982-06-28 | 1987-11-15 | Bristol Myers Co | Cephalosporinderivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen die sie enthalten. |
| US4480098A (en) * | 1982-11-12 | 1984-10-30 | Eli Lilly And Company | Preparation of alkali metal thieno(furo)pyridines |
| US4525473A (en) * | 1983-03-30 | 1985-06-25 | Bristol-Myers Company | Cephalosporins |
| EP0137442A3 (de) * | 1983-10-08 | 1986-01-15 | Hoechst Aktiengesellschaft | Cephalosporinderivate und Verfahren zu ihrer Herstellung |
| EP0138552A3 (en) * | 1983-10-17 | 1986-03-19 | Eli Lilly And Company | Improvements on or relating to 3-bicyclicpyridinium-methyl cephalosporins |
| US4868173A (en) * | 1984-11-20 | 1989-09-19 | Ici Pharma | Cephalosporin derivatives |
| EP0187456A1 (en) * | 1984-11-29 | 1986-07-16 | Ici Pharma | Cephalosporin derivatives |
| ATE89826T1 (de) * | 1985-03-01 | 1993-06-15 | Takeda Chemical Industries Ltd | Antibakterielle verbindungen, ihre herstellung und verwendung. |
| US4703118A (en) * | 1985-04-08 | 1987-10-27 | Eli Lilly And Company | Synthesis of 3-iodomethyl cephalosporins |
| US4714760A (en) * | 1985-08-20 | 1987-12-22 | Bristol-Myers Company | Cephalosporin intermediates |
| GB8626245D0 (en) * | 1985-11-27 | 1986-12-03 | Ici Pharma | Cephalosporin compounds |
| US4868294A (en) * | 1986-07-11 | 1989-09-19 | Bristol-Myers Company | Process for preparing cephalosporin intermediates |
| US4918067A (en) * | 1986-07-24 | 1990-04-17 | Beecham Group P.L.C. | Heterocyclic substituted penicillin antibiotics |
| TW526202B (en) | 1998-11-27 | 2003-04-01 | Shionogi & Amp Co | Broad spectrum cephem having benzo[4,5-b]pyridium methyl group of antibiotic activity |
| NZ520696A (en) * | 2000-02-10 | 2004-03-26 | Upjohn Co | Piperazine amide substituted oxazolidinone thioamides useful for treating bacteria infections |
| US6642238B2 (en) | 2000-02-10 | 2003-11-04 | Pharmacia And Upjohn Company | Oxazolidinone thioamides with piperazine amide substituents |
| EP1618114B1 (en) | 2003-04-16 | 2010-07-14 | Sandoz AG | Processes for the preparations of cefepime |
| US7847093B2 (en) | 2003-04-16 | 2010-12-07 | Sandoz Ag | Processes for the preparations of cefepime |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| GR63088B (en) * | 1976-04-14 | 1979-08-09 | Takeda Chemical Industries Ltd | Preparation process of novel cephalosporins |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| FR2440738A1 (fr) * | 1978-11-13 | 1980-06-06 | Parcor | Medicament a base de derives des thieno (2,3-c) et (3,2-c) pyridines |
| DE3118732A1 (de) * | 1981-05-12 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| DE3207840A1 (de) * | 1982-03-04 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | "cephalosporinderivate und verfahren zu ihrer herstellung" |
-
1982
- 1982-09-06 GR GR69206A patent/GR76701B/el unknown
- 1982-09-06 RO RO108573A patent/RO84456B/ro unknown
- 1982-09-06 SU SU823485553A patent/SU1169542A3/ru active
- 1982-09-06 IL IL66726A patent/IL66726A0/xx unknown
- 1982-09-06 PL PL23815882A patent/PL238158A1/xx unknown
- 1982-09-07 FI FI823088A patent/FI823088L/fi not_active Application Discontinuation
- 1982-09-07 ES ES515548A patent/ES8404361A1/es not_active Expired
- 1982-09-07 NZ NZ201833A patent/NZ201833A/xx unknown
- 1982-09-07 GB GB08225403A patent/GB2105719A/en not_active Withdrawn
- 1982-09-07 PT PT75518A patent/PT75518B/pt unknown
- 1982-09-07 EP EP82304674A patent/EP0074268A3/en not_active Withdrawn
- 1982-09-07 DK DK399282A patent/DK399282A/da not_active Application Discontinuation
- 1982-09-07 PH PH27833A patent/PH19756A/en unknown
- 1982-09-07 KR KR1019820004043A patent/KR840001585A/ko unknown
- 1982-09-07 HU HU822856A patent/HU187575B/hu unknown
- 1982-09-07 DD DD82243071A patent/DD209633A5/de unknown
- 1982-09-08 CS CS826505A patent/CS232735B2/cs unknown
-
1983
- 1983-12-02 ES ES527763A patent/ES527763A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8505374A1 (es) | 1985-05-16 |
| GB2105719A (en) | 1983-03-30 |
| DK399282A (da) | 1983-03-09 |
| FI823088A0 (fi) | 1982-09-07 |
| HU187575B (en) | 1986-01-28 |
| EP0074268A3 (en) | 1984-05-23 |
| ES515548A0 (es) | 1984-04-16 |
| RO84456A (ro) | 1984-06-21 |
| ES8404361A1 (es) | 1984-04-16 |
| PT75518A (en) | 1982-10-01 |
| DD209633A5 (de) | 1984-05-16 |
| NZ201833A (en) | 1985-09-13 |
| CS650582A2 (en) | 1984-06-18 |
| IL66726A0 (en) | 1982-12-31 |
| FI823088L (fi) | 1983-03-09 |
| RO84456B (ro) | 1984-08-30 |
| PL238158A1 (en) | 1984-11-19 |
| GR76701B (ko) | 1984-08-29 |
| CS232735B2 (en) | 1985-02-14 |
| SU1169542A3 (ru) | 1985-07-23 |
| PT75518B (en) | 1985-11-12 |
| PH19756A (en) | 1986-06-26 |
| ES527763A0 (es) | 1985-05-16 |
| EP0074268A2 (en) | 1983-03-16 |
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