KR940002257A - 세팔로스포린 중간체의 제조방법 - Google Patents
세팔로스포린 중간체의 제조방법 Download PDFInfo
- Publication number
- KR940002257A KR940002257A KR1019930013578A KR930013578A KR940002257A KR 940002257 A KR940002257 A KR 940002257A KR 1019930013578 A KR1019930013578 A KR 1019930013578A KR 930013578 A KR930013578 A KR 930013578A KR 940002257 A KR940002257 A KR 940002257A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- cycloalkane
- optionally substituted
- equivalent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 7
- 229930186147 Cephalosporin Natural products 0.000 title abstract 3
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 150000001780 cephalosporins Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims 24
- 150000001924 cycloalkanes Chemical class 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- PASACJUCYZVYOQ-UHFFFAOYSA-N [I].C[SiH](C)C Chemical compound [I].C[SiH](C)C PASACJUCYZVYOQ-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical group CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 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
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 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
- 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
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cephalosporin Compounds (AREA)
Abstract
본 발명은 △2이성체가 실제로 없으며, 광범위 스펙트럼 페팔로스포린 항생제로 전환될 수 있는 다음식의 안정한, 결정체 세팔로스포린 중간체의 제조방법을 제공한다.
상기식에서 X는 Hl, HCI 토는 H2SO4이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 한가지 또는 두가지의 (저급)알킬에 의해 임의로 치환된 C5-8시클로알칸내에서 다음식(Ⅱ)의 화합물을 (저급)알칸올로서 처리하여 실릴기를 제거하고, 이어서 산성화반응시켜 다음식(Ⅰ)의 화합물을 제조하는 단계로 이루어진, 실제로 △2이성체가 없는 다음식(Ⅰ)을 가진 안정한, 결정체 화합물의 제조방법:상기식에서 X는 Hl, HCI 토는 H2SO4이다.
- 제1항에 있어서, 한가지 또는 두가지의 (저급)알킬에 의해 임의로 치환된 C5-8시클로알칸내에서 다음식(Ⅲ)의 화합물을 다음식의 화합물과 반응시킴으로서 △2이성체가 실제로 없는 식(Ⅱ)의 화합물의 제조 단계를 추가로 구성한 것이 특징인 제조방법.
- 제2항에 있어서, 한가지 또는 두가지의 (저급)알킬에 의해 임의로 치환된 C5-8시클로알칸내에서 다음식(Ⅳ)의 화합물을 화합물(Ⅳ)의 당량당 요오드트리메틸실란 적어도 1당량으로 처리함으로서 △2이성체가 실제로 없는 식(Ⅲ)의 화합물의 제조 단계를 추가로 구성한 것이 특징인 제조방법.
- 제3항에 있어서, 한가지 또는 두가지의 (저급)알킬에 의해 임의로 치환된 C5-8시클로알칸내에서 다음식(Ⅴ)의 화합물을 화합물(Ⅴ)의 당량당 헥사메틸디실라잔 적어도 1당량 및 촉매량의 요오드트리메틸실란으로서 처리함으로서 △2이성체가 실제로 없는 식(Ⅳ)의 화합물의 제조 단게를 추가로 구성한 것이 특징인 제조방법.
- 한가지 또는 두가지의 (저급)알킬에 의해 임의로 치환된 C5-8시클로알칸내에서 다음식(Ⅳ)의 화합물을 화합물(Ⅳ)의 당량당 다음식의 화합물 적어도 1당량 그후 요오드트리메틸실란 적어도 1당량으로서 처리하고 이어서 (저급)알칸올로서 처리하여 실릴기를 제거하고, 산성화시켜 식(Ⅰ)의 화합물을 제조하는 단계로 이루어진, 실제로 △2이성체가 없는 다음식(Ⅰ)의 안정한, 결정체 화합물의 제조방법.(상기식에서 X는 Hl, HCI 토는 H2SO4이다)
- 한가지 또는 두가지의 (저급)알킬에 의해 임의로 치환된 C5-8시클로알칸내에서 다음식(Ⅵ)의 화합물을 한가지 또는 두가지의 (저급)알킬에 의해 임의로 치환된 C5-8시클로알칸내에서 다음식(Ⅵ)의 화합물로서 처리하고, 이어서 (저급)알칸올로서 처리하여 실릴기를 제거하고, 산성화시켜 식(Ⅰ)의 화합물을 제조하는 단계로 이루어진 실제로 △2이성체가 없는 다음식(Ⅰ)의 안정한, 결정체 화합물의 제조방법.(상기식에서 X는 Hl, HCI 토는 H2SO4이다)
- 제6항에 있어서, 한가지 또는 두가지의 (저급)알킬에 의해 임의로 치환된 C5-8시클로알칸내에서 다음식(Ⅴ)의 화합물을 화합물(Ⅴ)의 당량당 헥사메틸디실라잔 적어도 1당량의 촉매량의 요오드트리메틸실란잔으로서 처리함으로 △2이성체가 없는 식(Ⅳ)의 화합물의 제조 단계를 추가로 구성한 것이 특징인 제조방법.
- 제1,5 또는 6항에 있어서, (저급)알칸올이 메탄올 또는 2-프로판올인 것이 특징인 제조방법.
- 제1,5 또는 6항에 있어서, C5-8시클로알칸이 시클로펜탄 또는 시클로헥산인 것이 특징인 제조방법.
- 제1,5 또는 6항에 있어서, C5-8시클로알칸이 메틸시클로펜탄 또는 메틸시클로헥산인 것이 특징인 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US92023292A | 1992-07-24 | 1992-07-24 | |
US920,232 | 1992-07-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR940002257A true KR940002257A (ko) | 1994-02-17 |
KR100290519B1 KR100290519B1 (ko) | 2001-09-17 |
Family
ID=25443394
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019930013578A KR100290519B1 (ko) | 1992-07-24 | 1993-07-19 | 세팔로스포린중간체의제조방법 |
Country Status (14)
Country | Link |
---|---|
US (1) | US5594131A (ko) |
EP (1) | EP0581220B1 (ko) |
JP (1) | JP3406653B2 (ko) |
KR (1) | KR100290519B1 (ko) |
AT (1) | ATE184608T1 (ko) |
CA (1) | CA2099692C (ko) |
DE (1) | DE69326400T2 (ko) |
DK (1) | DK0581220T3 (ko) |
ES (1) | ES2137211T3 (ko) |
GR (1) | GR3032045T3 (ko) |
HU (1) | HU213399B (ko) |
IL (1) | IL106388A (ko) |
MX (1) | MX9304433A (ko) |
TW (1) | TW232695B (ko) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IN184516B (ko) * | 1996-01-19 | 2000-09-02 | Lupin Laoratories Ltd | |
ATE244248T1 (de) * | 1996-04-12 | 2003-07-15 | Takeda Chemical Industries Ltd | Herstellung von amino cephalosporansäurederivaten |
JP4616844B2 (ja) * | 2003-12-23 | 2011-01-19 | サンド・ゲーエムベーハー | セファロスポリン合成に使用するための中間体の生成プロセス |
US20070111980A1 (en) | 2004-07-16 | 2007-05-17 | Bandi Parthasaradhi Reddy | Process for preparing pure cephalosporine intermediates |
WO2006075244A2 (en) * | 2005-01-17 | 2006-07-20 | Orchid Chemicals & Pharmaceuticals Ltd | Improved process for the preparation of cephalosporin antibiotic intermediate |
WO2008010042A2 (en) * | 2006-07-18 | 2008-01-24 | Orchid Chemicals & Pharmaceuticals Limited | Improved process for the preparation of cefepime intermediate |
WO2009004463A1 (en) * | 2007-07-04 | 2009-01-08 | Orchid Chemicals & Pharmaceuticals Limited | Improved process for the preparation of cefepime intermediate |
CN107201391B (zh) * | 2017-07-04 | 2020-07-07 | 吉林省爱诺德生物工程有限公司 | 一种盐酸头孢吡肟的合成方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4406899A (en) * | 1982-03-04 | 1983-09-27 | Bristol-Myers Company | Cephalosporins |
US4574052A (en) * | 1984-05-31 | 1986-03-04 | Richardson-Vicks Inc. | Crackling aerosol foam |
US4910301A (en) * | 1985-08-05 | 1990-03-20 | Bristol-Myers Company | Cefepime cephalosporin salts |
US4659812A (en) * | 1985-08-20 | 1987-04-21 | Bristol-Myers Company | Cephalosporin intermediates |
US4714760A (en) * | 1985-08-20 | 1987-12-22 | Bristol-Myers Company | Cephalosporin intermediates |
US4868294A (en) * | 1986-07-11 | 1989-09-19 | Bristol-Myers Company | Process for preparing cephalosporin intermediates |
-
1993
- 1993-06-29 TW TW082105173A patent/TW232695B/zh not_active IP Right Cessation
- 1993-06-29 CA CA002099692A patent/CA2099692C/en not_active Expired - Fee Related
- 1993-07-09 JP JP22041193A patent/JP3406653B2/ja not_active Expired - Lifetime
- 1993-07-19 KR KR1019930013578A patent/KR100290519B1/ko not_active IP Right Cessation
- 1993-07-19 IL IL10638893A patent/IL106388A/en not_active IP Right Cessation
- 1993-07-22 MX MX9304433A patent/MX9304433A/es unknown
- 1993-07-23 ES ES93111880T patent/ES2137211T3/es not_active Expired - Lifetime
- 1993-07-23 AT AT93111880T patent/ATE184608T1/de not_active IP Right Cessation
- 1993-07-23 DE DE69326400T patent/DE69326400T2/de not_active Expired - Lifetime
- 1993-07-23 EP EP93111880A patent/EP0581220B1/en not_active Expired - Lifetime
- 1993-07-23 DK DK93111880T patent/DK0581220T3/da active
- 1993-07-23 HU HU9302145A patent/HU213399B/hu not_active IP Right Cessation
-
1995
- 1995-02-02 US US08/382,556 patent/US5594131A/en not_active Expired - Lifetime
-
1999
- 1999-12-06 GR GR990403132T patent/GR3032045T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
TW232695B (ko) | 1994-10-21 |
KR100290519B1 (ko) | 2001-09-17 |
DK0581220T3 (da) | 1999-12-20 |
IL106388A (en) | 1999-10-28 |
GR3032045T3 (en) | 2000-03-31 |
ATE184608T1 (de) | 1999-10-15 |
JPH06184161A (ja) | 1994-07-05 |
HU213399B (en) | 1997-06-30 |
CA2099692A1 (en) | 1994-01-25 |
DE69326400D1 (de) | 1999-10-21 |
HUT64963A (en) | 1994-03-28 |
HU9302145D0 (en) | 1993-10-28 |
JP3406653B2 (ja) | 2003-05-12 |
MX9304433A (es) | 1994-02-28 |
CA2099692C (en) | 2003-09-30 |
EP0581220A2 (en) | 1994-02-02 |
IL106388A0 (en) | 1993-11-15 |
US5594131A (en) | 1997-01-14 |
ES2137211T3 (es) | 1999-12-16 |
EP0581220B1 (en) | 1999-09-15 |
EP0581220A3 (en) | 1994-05-18 |
DE69326400T2 (de) | 2000-05-18 |
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