KR840009114A - 세팔로스포린에서 유도된 항생화합물 제조방법 - Google Patents
세팔로스포린에서 유도된 항생화합물 제조방법 Download PDFInfo
- Publication number
- KR840009114A KR840009114A KR1019840002913A KR840002913A KR840009114A KR 840009114 A KR840009114 A KR 840009114A KR 1019840002913 A KR1019840002913 A KR 1019840002913A KR 840002913 A KR840002913 A KR 840002913A KR 840009114 A KR840009114 A KR 840009114A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- formula
- compound
- acid
- atom
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 8
- 229930186147 Cephalosporin Natural products 0.000 title claims 2
- 230000003115 biocidal effect Effects 0.000 title claims 2
- 229940124587 cephalosporin Drugs 0.000 title claims 2
- 150000001780 cephalosporins Chemical class 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims 6
- -1 amine salt Chemical class 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 150000003573 thiols Chemical group 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 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
- C07D501/36—Methylene radicals, substituted by 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
-
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Professional, Industrial, Or Sporting Protective Garments (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 하기 일반식 Ⅱ의 4-터시오부틸-7-아미노-3-브로모메틸-3-세펨카르복실레이트 1-S-옥사이드를하기 일반식의 Ⅲ산으로 아실화 시켜 하기 일반식 Ⅳ를 얻고(1),일반식 Ⅳ의 화합물에 산 B-(CH2)n-COOH 또는 티오산 B-(CH2)n-COSH를 (식중에서, B는 하기에 정의한 바와 같고, 아민기는 미리 보호되었다.)첨가하여 하기 일반식 Ⅴ의 화합물을 형성하고(2),아민과 카르복시기의 보호기를 제거하여 A가 수소인 하기 일반식 Ⅰ의 화합물을 얻고(3),얻은 위의 화합물 Ⅰ을 무기 또는 유기염기로 반응시키거나 에스테르화시켜 A가 수소가 아닌 일반식 Ⅰ의 환합물로 임의 전환 시키거나(4),얻은 위의 화합물 Ⅰ을 약학적으로 허용 가능한 산과 반응시켜 이들의 염으로 임의 전환시킴(5)을 특징으로 하는 하기 일반식 의 세팔로스포린에서 유도된 항생화합물의 제조방법.식중에서, 4위치에서 COOA기는 산 라디칼 또는 알칼리 또는 알칼리 또는 알칼리토염 또는 트리에틸아만 또는 에탄올아민과 같은 아민염 또는 용이하게 가수분해되거나 대사가 불안정하고 약학적으로 허용 가능한 에스테르 라디칼이다.. X는 산소원자 또는 황원자이다.. n은 0또는 1이다.. R1과 R2는 각각 수소 또는 저급 알킬기, 바람직하기로는 메틸기이거나,. R1과 R2는 탄소원자로 결합되어 시클로부틸 또는 시클로펜틸 핵을 형성한다.. B는 하기 기들에서 선택한 1차 또는 2차 아민의 잔유물이다;-Z-NH-R(식중에서, Z는 황원자로 임의 중단되고, 히드록실, 티올, 메틸티오, 아미노, 아세트아미도, 카르바모일, 페닐, 히드록시페닐 또는 이미다졸일기로 임의 치환된 2 내지 7탄소 원자를 갖는 직쇄 또는 층쇄 알킬렌기이다. Z는 또한 시클로 펜틸리덴 또는 시클로헥실리덴기가 될 수 있다. R은 수소원자 또는 1 내지 3탄소원자를 갖는 알킬기이다.)-Z′-Alk-NH-R(식중에서, Z′는 하나의 할로겐원자 또는 1또는 2의 메톡시기 1,2 또는 3메틸기로 임의 치환된 1,2-페닐렌 또는 1,3-페닐렌 또는 1,4-페닐렌기이거나, Z′는 1,2-시클로 헥실렌, 1,3-시클로헥실렌 또는 1,4-시클로헥실렌기이다. Alk는 1 내지 3탄소원자를 갖는 직쇄 또는 측쇄 알킬기이다. R은 위에서 정의한 바와 같다)(식중에서, Z′는 위에서 정의한 바와 같다. Y는 m=0,1,2,3 또는 4인 알킬기(CH2)m이고, 2 또는 3탄소원자를 갖는 측쇄 알킬기이거나 Y와 NH-R″는고리이다 (R′와 R″는 같거나 다르고, 상기의 R과 동일한 의미를 갖는다),-Z″-NH-R(식중에서 Z″는 1,3-시클로헥실렌 또는 1,4-시클로헥실렌기이고, R은 전술한 바와 같다.)(식중에서, R3은 수소원자 또는 메틸기이다. n은 0 또는 1이고, Alk와 R은 이던에 정의한 바와 같다.)-CO-Alk-NH2기(Alk는 이전에 정의한 바와 같다.)또는로 질소원자에 임의 치환된 2-피페리딜, 3-피페리딜 또는 4-피페리딜기이다.식중에서, T2는 트리틸기, tBu는 터시오부틸기이고 R1과 R2는 상기에서 정의했다.식중에서, T2, R1, R2,n은 상기에서 정의했고 B′는 아민기가 보호된 B기를 나타낸다.
- 제1항에 있어서, 산 B-(CH2)n-COOH의 나트륨 또는 칼륨염을 중간체로 사용하여 비양자성 극성 용매에 첨가시킴을 특징으로 하는 방법.
- 제1항에 있어서, 티오산 B′-(CH2)N-COSH의 나트륨 또는 칼륨염을 사용하여 비극성용매에 첨가시킴을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8308862 | 1983-05-27 | ||
| FR83-08862 | 1983-05-27 | ||
| FR8308862A FR2546520B1 (fr) | 1983-05-27 | 1983-05-27 | Nouveaux composes antibiotiques derives des cephalosporines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840009114A true KR840009114A (ko) | 1984-12-24 |
| KR910004302B1 KR910004302B1 (ko) | 1991-06-25 |
Family
ID=9289271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840002913A KR910004302B1 (ko) | 1983-05-27 | 1984-05-26 | 세팔로스포린에서 유도된 항생 화합물 제조방법 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4656166A (ko) |
| EP (1) | EP0127543B1 (ko) |
| JP (1) | JPS59227886A (ko) |
| KR (1) | KR910004302B1 (ko) |
| AT (1) | ATE46339T1 (ko) |
| AU (1) | AU570973B2 (ko) |
| CA (1) | CA1247596A (ko) |
| CS (1) | CS241546B2 (ko) |
| DD (1) | DD219773A5 (ko) |
| DE (1) | DE3479733D1 (ko) |
| DK (1) | DK255684A (ko) |
| ES (1) | ES532805A0 (ko) |
| FI (1) | FI842042A (ko) |
| FR (1) | FR2546520B1 (ko) |
| GR (1) | GR82042B (ko) |
| HU (1) | HU191658B (ko) |
| IL (1) | IL71933A (ko) |
| MA (1) | MA20126A1 (ko) |
| NO (1) | NO163408C (ko) |
| NZ (1) | NZ208275A (ko) |
| OA (1) | OA07777A (ko) |
| PH (1) | PH20389A (ko) |
| PL (1) | PL144003B1 (ko) |
| PT (1) | PT78635B (ko) |
| SU (1) | SU1282817A3 (ko) |
| YU (1) | YU90684A (ko) |
| ZA (1) | ZA843995B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2546520B1 (fr) * | 1983-05-27 | 1985-08-30 | Sanofi Sa | Nouveaux composes antibiotiques derives des cephalosporines |
| FR2570702B1 (fr) * | 1984-09-27 | 1987-01-09 | Sanofi Sa | Derives des cephalosporines, procedes d'obtention et leur application a titre d'antibiotiques |
| JPS61207822A (ja) * | 1985-03-12 | 1986-09-16 | Toyota Motor Corp | 吸気管長可変式吸気装置の吸気制御弁の制御方法 |
| US4783443A (en) * | 1986-03-03 | 1988-11-08 | The University Of Chicago | Amino acyl cephalosporin derivatives |
| US5147871A (en) * | 1986-07-03 | 1992-09-15 | Hoffmann La-Roche, Inc. | Anti-bacterial cephalosporin compounds |
| FR2621589B1 (fr) * | 1987-10-08 | 1990-03-02 | Sanofi Sa | Derives des cephalosporines a pharmacocinetique amelioree, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2607135B1 (fr) * | 1986-11-20 | 1989-04-28 | Sanofi Sa | Nouveaux derives des cephalosporines a pharmacocinetique amelioree, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US5189157A (en) * | 1987-06-16 | 1993-02-23 | Hoffmann La Roche Inc. | Antibacterial cephalosporin compounds |
| US5336768A (en) * | 1988-05-24 | 1994-08-09 | Hoffmann-La Roche Inc. | Antibacterial cephalosporin compounds |
| CS273349B2 (en) * | 1988-03-31 | 1991-03-12 | Hoffmann La Roche | Method of cephalosporin's new derivatives production |
| DE10134478B4 (de) * | 2001-07-16 | 2007-10-31 | Priaton Gmbh | Verfahren zur Darstellung von thiazolsubstituierten β-Lactamen |
| FR2842523A1 (fr) * | 2002-07-17 | 2004-01-23 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur application en therapeutique |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338438A (en) * | 1970-06-16 | 1982-07-06 | Merck & Co., Inc. | Cephalosporin antibiotics |
| BE768844A (en) * | 1971-06-22 | 1971-12-22 | Fujisawa Pharmaceutical Co | 7-(2-acyloxy-acetamido)-3-cephem-4-carboxylic acid derivs - - antibacterials |
| GB1425933A (en) * | 1972-03-13 | 1976-02-25 | Astra Laekemedel Ab | Cephalosporins |
| OA05033A (fr) * | 1974-07-01 | 1980-12-31 | Rhone Poulenc Ind | Nouveaux dérivés de la céphalosporine et leur préparation. |
| FR2342733A1 (fr) * | 1976-01-14 | 1977-09-30 | Roussel Uclaf | Derives de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| DE2760484C2 (ko) * | 1976-04-14 | 1992-12-03 | Takeda Chemical Industries, Ltd., Osaka, Jp | |
| DE2716677C2 (de) * | 1977-04-15 | 1985-10-10 | Hoechst Ag, 6230 Frankfurt | Cephemderivate und Verfahren zu ihrer Herstellung |
| US4341775A (en) * | 1978-09-11 | 1982-07-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4409215A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
| FR2501209B1 (fr) * | 1981-03-03 | 1986-07-04 | Sanofi Sa | Nouveaux derives des cephalosporines et medicaments antibiotiques contenant lesdits derives |
| FR2485540A1 (fr) * | 1980-06-30 | 1981-12-31 | Sanofi Sa | Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant |
| DE3177090D1 (en) * | 1980-12-31 | 1989-09-28 | Fujisawa Pharmaceutical Co | 7-acylaminocephalosporanic acid derivatives and processes for the preparation thereof |
| FR2506307A1 (fr) * | 1981-05-22 | 1982-11-26 | Roussel Uclaf | Nouveaux derives substitues de l'acide 2-(2-amino 4-thiazolyl) 2-hydroxyimino acetique et leur procede de preparation |
| US4396619A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin betaines |
| FR2546520B1 (fr) * | 1983-05-27 | 1985-08-30 | Sanofi Sa | Nouveaux composes antibiotiques derives des cephalosporines |
-
1983
- 1983-05-27 FR FR8308862A patent/FR2546520B1/fr not_active Expired
-
1984
- 1984-05-22 US US06/612,896 patent/US4656166A/en not_active Ceased
- 1984-05-22 FI FI842042A patent/FI842042A/fi not_active Application Discontinuation
- 1984-05-22 CA CA000454824A patent/CA1247596A/en not_active Expired
- 1984-05-24 PT PT78635A patent/PT78635B/pt not_active IP Right Cessation
- 1984-05-24 DD DD84263344A patent/DD219773A5/de not_active IP Right Cessation
- 1984-05-24 AU AU28582/84A patent/AU570973B2/en not_active Ceased
- 1984-05-24 PH PH30714A patent/PH20389A/en unknown
- 1984-05-24 GR GR74812A patent/GR82042B/el unknown
- 1984-05-24 DK DK255684A patent/DK255684A/da not_active Application Discontinuation
- 1984-05-25 DE DE8484401080T patent/DE3479733D1/de not_active Expired
- 1984-05-25 NZ NZ208275A patent/NZ208275A/en unknown
- 1984-05-25 EP EP84401080A patent/EP0127543B1/fr not_active Expired
- 1984-05-25 SU SU843749939A patent/SU1282817A3/ru active
- 1984-05-25 AT AT84401080T patent/ATE46339T1/de not_active IP Right Cessation
- 1984-05-25 NO NO842091A patent/NO163408C/no unknown
- 1984-05-25 IL IL71933A patent/IL71933A/xx unknown
- 1984-05-25 ZA ZA843995A patent/ZA843995B/xx unknown
- 1984-05-25 ES ES532805A patent/ES532805A0/es active Granted
- 1984-05-25 PL PL1984247843A patent/PL144003B1/pl unknown
- 1984-05-25 YU YU00906/84A patent/YU90684A/xx unknown
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- 1984-05-25 OA OA58304A patent/OA07777A/xx unknown
- 1984-05-25 MA MA20348A patent/MA20126A1/fr unknown
- 1984-05-26 KR KR1019840002913A patent/KR910004302B1/ko active IP Right Grant
- 1984-05-28 JP JP59108253A patent/JPS59227886A/ja active Pending
- 1984-05-28 CS CS843997A patent/CS241546B2/cs unknown
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