KR930004312A - 세팔로스포린의 제조방법 및 이 방법에서의 중간체 - Google Patents
세팔로스포린의 제조방법 및 이 방법에서의 중간체 Download PDFInfo
- Publication number
- KR930004312A KR930004312A KR1019920014890A KR920014890A KR930004312A KR 930004312 A KR930004312 A KR 930004312A KR 1019920014890 A KR1019920014890 A KR 1019920014890A KR 920014890 A KR920014890 A KR 920014890A KR 930004312 A KR930004312 A KR 930004312A
- Authority
- KR
- South Korea
- Prior art keywords
- iii
- compound
- formula
- protecting group
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 6
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 239000001257 hydrogen Substances 0.000 claims abstract 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 239000012038 nucleophile Substances 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- -1 alkyl radical Chemical class 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 239000012336 iodinating agent Substances 0.000 claims 2
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical group 0.000 claims 1
- ZYLDQHILNOZKIF-IOJJLOCKSA-N (6R)-7-amino-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class CC=CC1=C(N2[C@H](SC1)C(N)C2=O)C(O)=O ZYLDQHILNOZKIF-IOJJLOCKSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 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
-
- 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
-
- 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- (ⅰ)하기 일반식(Ⅸ)의 화합물을 3′-위치에서의 친핵성 교환 반응에 적용시키는 단계, 및 임의로 실릴 보호그룹을 제거하는 단계를 포함함을 특징으로 하여 하기 일반식(Ⅰ)의 3′-치환된 7-아미노-3-프로페닐-4-세펨-카복실산 유도체 및 이의 산 부가염을 제조하는 방법.상기식에서, R1은 수소 또는 보호그룹이고, R0는 수소 또는 메톡시이며, X는 친핵체의 라디칼이고, R은 수소, 실릴 보호 그를 또는 음전하이며, R6는 실릴 보호 그룹이다.
- 제1항에 있어서, 일반식(Ⅸ)의 화합물이 (ⅱ)하기 일반식(Ⅷ)의 화합물을 요오드화제와 반응시키는 단계에 의해 제조되는 방법.상기식에서, R0및 R6는 제1항에서 정의한 바와 같고, R10은 실릴 보호 그룹, 임의로 치환된 직쇄 또는 측쇄알킬 라디칼, 임의로 치환된 아릴 라디칼 또는 아실 라디칼이다.
- 제2항에 있어서, 일반식(Ⅷ)의 화합물이 (ⅲ)하기 일반식(Ⅶ)의 화합물을 실릴화시키는 단계에 의해 제조되는 방법.상기식에서, R0는 제1항에서 정의한 바와 같고, R9은 수소, 임의로 치환된 직쇄 또는 측쇄 알킬 라디칼, 임의로 치환된 아릴 라디칼 또는 아실 라디칼이다.
- 제2항 또는 제3항에 있어서, 제1항, 제2항 및 제3항에서 정의된 바와 같은 단계 (ⅰ), (ⅱ) 및 (ⅲ)을 동일한 반응 용기내에서 수행시키는 방법.
- 하기 일반식(Ⅸ)의 화합물.상기식에서, R0는 수소 또는 메톡시이고, R6는 실릴 보호 그룹이다.
- 7-트리메틸실릴아미노-3-(3-요오도-1-프로펜-1-일)-3-세펨-4-카복실산 트리메틸실릴 에스테르.
- (ⅱ)하기 일반식(Ⅷ)의 화합물을 요오드화제와 반응시키는 단계를 포함함을 특징으로 하여 하기 일반식(Ⅸ)의 화합물을 제조하는 방법.상기식에서, R6는 실릴 보호그룹이고, R0는 수소 또는 메톡시이며, R10은 실릴 보호그룹, 임의로 치환된 직쇄 또는 측쇄 알킬 라디칼, 임의로 치환된 아릴 라디칼 또는 아실 라디칼이다.
- 7-아실아미노-1-프로펜-1-일-3-세펨-4-카복실산의 제조를 위한 일반식(Ⅸ)의 화합물의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT0163691A AT396108B (de) | 1991-08-21 | 1991-08-21 | Neues verfahren und neue zwischenprodukte zur herstellung von 7-aminocephalosporansaeurederivaten |
ATA1636/91 | 1991-08-21 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019990053237A Division KR100286422B1 (ko) | 1991-08-21 | 1999-11-27 | 세팔로스포린의 제조방법 및 이 방법에서의 중간체 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR930004312A true KR930004312A (ko) | 1993-03-22 |
Family
ID=3517697
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019920014890A KR930004312A (ko) | 1991-08-21 | 1992-08-19 | 세팔로스포린의 제조방법 및 이 방법에서의 중간체 |
KR1019990053237A KR100286422B1 (ko) | 1991-08-21 | 1999-11-27 | 세팔로스포린의 제조방법 및 이 방법에서의 중간체 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019990053237A KR100286422B1 (ko) | 1991-08-21 | 1999-11-27 | 세팔로스포린의 제조방법 및 이 방법에서의 중간체 |
Country Status (9)
Country | Link |
---|---|
US (3) | US5686604A (ko) |
EP (1) | EP0528343B1 (ko) |
JP (1) | JP2561780B2 (ko) |
KR (2) | KR930004312A (ko) |
AT (2) | AT396108B (ko) |
DE (1) | DE69232776T2 (ko) |
ES (1) | ES2183804T3 (ko) |
PT (1) | PT528343E (ko) |
SG (1) | SG52784A1 (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR0164458B1 (ko) * | 1995-04-04 | 1999-01-15 | 김은영 | 암모니오세팔로스포린 계열 항생제 및 그의 제조방법 |
AT403161B (de) * | 1995-07-19 | 1997-11-25 | Biochemie Gmbh | Verfahren zur herstellung von cephemverbindungen |
US5872249A (en) * | 1995-09-01 | 1999-02-16 | Korea Institute Of Science And Technology | 3-ammoniopropenyl cephalosporin compounds as antibacterial agents and process for preparing the same |
US6011136A (en) * | 1995-11-21 | 2000-01-04 | Novartis Ag | Cyclopeptolides |
CN1173979C (zh) | 1998-06-22 | 2004-11-03 | 巴斯利尔药物股份公司 | 丙烯基头孢茵素衍生物 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
US4049806A (en) * | 1975-08-15 | 1977-09-20 | Syntex (U.S.A.) Inc. | Cephalosporin type antibacterials |
US4112087A (en) * | 1976-11-04 | 1978-09-05 | Syntex (U.S.A.) Inc. | Cephalosporin type antibacterials having a substituted propenyl group in the 3-position |
DE2659288A1 (de) * | 1976-12-29 | 1978-07-06 | Schering Ag | Mittel mit bakterizider und fungizider wirkung |
NL162387C (nl) * | 1977-09-06 | 1980-05-16 | Gist Brocades Nv | Werkwijze voor het bereiden van 6-(d-alpha-amino-p- -hydroxyfenylacetamido)penicillanzuur. |
US4640798A (en) * | 1982-05-26 | 1987-02-03 | Lilly Industries Ltd. | Intermediates for the preparation of penicillin and cephalosporin compounds |
ZA84584B (en) * | 1983-01-28 | 1984-09-26 | Bristol Myers Co | Substituted vinyl cephalosporins |
US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
CA1276929C (en) * | 1984-04-09 | 1990-11-27 | Masahisa Oka | Cephalosporin antibacterial agents |
JP2572382B2 (ja) * | 1984-11-23 | 1997-01-16 | ビオヘミ−・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | セフアロスポリン誘導体の新規製造方法 |
AT382873B (de) * | 1984-11-23 | 1987-04-27 | Biochemie Gmbh | Verfahren zur herstellung von cephalosporinderivaten |
US4703118A (en) * | 1985-04-08 | 1987-10-27 | Eli Lilly And Company | Synthesis of 3-iodomethyl cephalosporins |
WO1987003875A1 (en) * | 1985-12-26 | 1987-07-02 | Eisai Co., Ltd. | Cephalosporin derivatives |
IL84128A (en) * | 1986-10-13 | 1992-12-01 | Eisai Co Ltd | 3-propenylcephem derivatives, their preparation and pharmaceutical compositions containing them |
FR2622585B1 (fr) * | 1987-11-03 | 1991-04-19 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 3 un radical vinyle substitue, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
ES2013403A6 (es) * | 1988-03-16 | 1990-05-01 | Eisai Co Ltd | Procedimiento para preparar derivados de cefem. |
-
1991
- 1991-08-21 AT AT0163691A patent/AT396108B/de not_active IP Right Cessation
-
1992
- 1992-08-12 DE DE69232776T patent/DE69232776T2/de not_active Expired - Fee Related
- 1992-08-12 SG SG1996009489A patent/SG52784A1/en unknown
- 1992-08-12 AT AT92113715T patent/ATE224393T1/de not_active IP Right Cessation
- 1992-08-12 ES ES92113715T patent/ES2183804T3/es not_active Expired - Lifetime
- 1992-08-12 PT PT92113715T patent/PT528343E/pt unknown
- 1992-08-12 EP EP92113715A patent/EP0528343B1/en not_active Expired - Lifetime
- 1992-08-19 KR KR1019920014890A patent/KR930004312A/ko active Application Filing
- 1992-08-20 JP JP4221330A patent/JP2561780B2/ja not_active Expired - Fee Related
-
1995
- 1995-05-05 US US08/437,083 patent/US5686604A/en not_active Expired - Fee Related
- 1995-05-05 US US08/437,084 patent/US5644052A/en not_active Expired - Lifetime
-
1997
- 1997-10-08 US US08/947,215 patent/US6169180B1/en not_active Expired - Fee Related
-
1999
- 1999-11-27 KR KR1019990053237A patent/KR100286422B1/ko not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE69232776T2 (de) | 2003-04-30 |
EP0528343A3 (en) | 1993-03-10 |
DE69232776D1 (de) | 2002-10-24 |
ATE224393T1 (de) | 2002-10-15 |
US6169180B1 (en) | 2001-01-02 |
EP0528343A2 (en) | 1993-02-24 |
SG52784A1 (en) | 1998-09-28 |
EP0528343B1 (en) | 2002-09-18 |
PT528343E (pt) | 2002-12-31 |
AT396108B (de) | 1993-06-25 |
US5686604A (en) | 1997-11-11 |
ES2183804T3 (es) | 2003-04-01 |
JPH05194533A (ja) | 1993-08-03 |
KR100286422B1 (ko) | 2001-03-15 |
JP2561780B2 (ja) | 1996-12-11 |
US5644052A (en) | 1997-07-01 |
ATA163691A (de) | 1992-10-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR950701902A (ko) | 리그난계 화합물의 제조방법(process for producing lignan compound) | |
ES2000604A6 (es) | Un procedimiento para preparar aril-piperidin esteres | |
AU562802B2 (en) | Preparation of phosphorus-containing cyanohydrins | |
KR930004312A (ko) | 세팔로스포린의 제조방법 및 이 방법에서의 중간체 | |
KR870007881A (ko) | 신규 알킬렌디아민 유도체의 제조방법 | |
KR910006288A (ko) | 신규 제조방법 | |
KR870011080A (ko) | 4-할로게노-2-옥시이미노-3-옥소부티르산류의 제조방법 | |
EP0206765A3 (en) | Process for preparation of rooperol, hypoxoside and derivatives thereof | |
KR930023366A (ko) | β-카르볼린 유도체 | |
KR860008963A (ko) | 페놀 유도체의 제조방법 | |
KR870003055A (ko) | 살충성 화합물 | |
ATE18208T1 (de) | N-(4-hydroxyphenyl)essigsaeureamid-estern aus 5benzoyl-1-methylpyrrol-2-essigsaeure. | |
KR950701338A (ko) | 메탄디포스폰산 화합물의 제조방법(Process for producing methanediphosphonate compound) | |
ES8300777A1 (es) | Metodo de obtener nuevos compuestos citostaticos del tipo de la vinblastina y similares. | |
KR920002564A (ko) | N-알킬 티아졸리딘 유도체 | |
KR840009109A (ko) | 페니실란산 유도체의 제조방법 | |
PT84870A (pt) | Processo para a preparacao de derivados da cefalosporina | |
ES488385A0 (es) | Procedimiento de preparacion de derivados de la xantona | |
KR910000753A (ko) | 신규한 세펨 유도체 | |
ATE41151T1 (de) | 3,4-dihydro-2,5,7,8-tetramethyl-2h-1benzopyranderivate und verfahren zu ihrer herstellung. | |
KR890003744A (ko) | 아졸 유도체의 제조방법 | |
KR960022427A (ko) | 2-(4'치환 아릴)프로피온산의 새로운 제조방법 | |
KR930004294A (ko) | 퀴놀론 유도체의 제조 방법 | |
KR830007509A (ko) | 아미노산 유도체의 제조방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
AMND | Amendment | ||
E902 | Notification of reason for refusal | ||
AMND | Amendment | ||
E601 | Decision to refuse application | ||
J201 | Request for trial against refusal decision | ||
A107 | Divisional application of patent | ||
B601 | Maintenance of original decision after re-examination before a trial | ||
J301 | Trial decision |
Free format text: TRIAL DECISION FOR APPEAL AGAINST DECISION TO DECLINE REFUSAL REQUESTED 19991029 Effective date: 20001230 |