RU96122784A - CEFALOSPORIN SYNTHESIS - Google Patents

CEFALOSPORIN SYNTHESIS

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Publication number
RU96122784A
RU96122784A RU96122784/04A RU96122784A RU96122784A RU 96122784 A RU96122784 A RU 96122784A RU 96122784/04 A RU96122784/04 A RU 96122784/04A RU 96122784 A RU96122784 A RU 96122784A RU 96122784 A RU96122784 A RU 96122784A
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RU
Russia
Prior art keywords
formula
compound
denotes
group
hydrogen
Prior art date
Application number
RU96122784/04A
Other languages
Russian (ru)
Other versions
RU2150471C1 (en
Inventor
Герд Ашер
Йоганнес Лудешер
Губерт Штурм
Йозеф ВИЗЕР
Original Assignee
Биокеми Гезелльшафт м.б.Х.
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Priority claimed from AT85794A external-priority patent/AT402927B/en
Priority claimed from AT0085894A external-priority patent/AT402072B/en
Priority claimed from AT0106694A external-priority patent/AT402929B/en
Application filed by Биокеми Гезелльшафт м.б.Х. filed Critical Биокеми Гезелльшафт м.б.Х.
Publication of RU96122784A publication Critical patent/RU96122784A/en
Application granted granted Critical
Publication of RU2150471C1 publication Critical patent/RU2150471C1/en

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Claims (9)

1. Соединение формулы IA
Figure 00000001

в которой
α) Ra обозначает водород или силильную группу; Rb обозначает группу формулы -ORe, в которой Re обозначает водород или алкил; а Rc и Rd вместе обозначают связь; или
β) Ra и Rd обозначает водород или силильную группу; а Rb и Rc совместно обозначают иминогруппу формулы =N-Y, в которой Y обозначает алкил, арил или гетероциклил;
γ) Rd обозначает водород или силильную группу; Ra обозначает водород, если Rd обозначает водород; либо Ra обозначает водород или силильную группу, если Rd обозначает силильную группу;
Rb и Rc совместно обозначают оксогруппу;
в свободной форме или в форме соли.1. The compound of formula IA
Figure 00000001

wherein
α) R a denotes hydrogen or silyl group; R b denotes a group of the formula —OR e , in which R e denotes hydrogen or alkyl; and R c and R d together represent a bond; or
β) R a and R d denotes hydrogen or a silyl group; and R b and R c together denote an imino group of the formula = NY, in which Y is alkyl, aryl or heterocyclyl;
γ) R d denotes hydrogen or silyl group; R a denotes hydrogen, if R d denotes hydrogen; or R a denotes hydrogen or a silyl group, if R d denotes a silyl group;
R b and R c together denote an oxo group;
in free form or in salt form. 2. Соединение формулы IA по п. 1, отличающееся тем, что оно имеет формулу I
Figure 00000002

в которой X- обозначает анион неорганической или органической кислоты, а R1 обозначает водород или алкильную группу.2. The compound of formula IA under item 1, characterized in that it has the formula I
Figure 00000002

in which X - denotes the anion of an inorganic or organic acid, and R 1 denotes hydrogen or an alkyl group. 3. Соединение формулы I по п. 2, отличающееся тем, что R1 обозначает водород.3. The compound of formula I according to claim 2, wherein R 1 denotes hydrogen. 4. Соединение формулы I по п. 2, отличающееся тем, что оно выбрано из группы, состоящей из 3H,7H-ацето[2,1-b]фуро[3,4-d][1,3]тиазин-1,7(4H)-дион, 6-амино-5а, 6-дигидро-3-гидрокси-гидрохлорида, 3H,7H-ацето[2,1-b]фуро[3,4-d] [1,3] тиазин-1,7(4H)-дион, 6-амино-5а,6-дигидро-3-гидрокси-толуолсульфоната, 3H, 7H-ацето[2,1-b] фуро[3,4-d] [1,3]тиазин-1,7(4H)-дион,6-амино-5а,6-дигидро-3-метокси-гидрохлорида и 3H, 7H-ацето[2,1-b] фуро[3,4-d] [1,3] тиазин-1,7(4H)-дион,6-амино-5а,6-дигидро-3-метокси-толуолсульфоната. 4. The compound of formula I according to claim 2, characterized in that it is selected from the group consisting of 3H, 7H-aceto [2,1-b] furo [3,4-d] [1,3] thiazin-1, 7 (4H) -dione, 6-amino-5a, 6-dihydro-3-hydroxy-hydrochloride, 3H, 7H-aceto [2,1-b] furo [3,4-d] [1,3] thiazine- 1.7 (4H) -dione, 6-amino-5a, 6-dihydro-3-hydroxy-toluenesulfonate, 3H, 7H-aceto [2,1-b] furo [3,4-d] [1,3] thiazin-1,7 (4H) -dione, 6-amino-5a, 6-dihydro-3-methoxy-hydrochloride and 3H, 7H-aceto [2,1-b] furo [3,4-d] [1, 3] thiazin-1,7 (4H) -dione, 6-amino-5a, 6-dihydro-3-methoxy-toluenesulfonate. 5. Соединение формулы IA по п. 1, отличающееся тем, что оно имеет формулу
Figure 00000003

в которой R обозначает водород или силильную группу.5. The compound of formula IA under item 1, characterized in that it has the formula
Figure 00000003

in which R denotes a hydrogen or silyl group. 6. Соединение формулы IA по п. 1, отличающееся тем, что оно имеет формулу
Figure 00000004

в которой Y имеет значение, определенное в п. 1, а R имеет значение, определенное в п. 5, в свободной форме или в форме соли.6. The compound of formula IA under item 1, characterized in that it has the formula
Figure 00000004

in which Y has the meaning given in claim 1, and R has the meaning given in claim 5, in free form or in salt form. 7. Соединение формулы II по п. 6, отличающееся тем, что Y обозначает возможно амино-, диалкиламино-, гидрокси-, алкокси-, алкил-, нитро-, гало-, карбалкокси- или карбамидо-замещенный алкил, арил или гетероциклил, а R такое как определено в п. 5. 7. A compound of formula II according to claim 6, wherein Y is optionally amino, dialkylamino, hydroxy, alkoxy, alkyl, nitro, halo, carbalkoxy or carbamido substituted alkyl, aryl or heterocyclyl, and R is as defined in clause 5. 8. Соединение формулы II по п. 6, отличающееся тем, что оно представляет собой 7-амино-3-(N-фенилимино)метил-3-цефем-4-карбоновую кислоту. 8. The compound of formula II according to claim 6, characterized in that it is a 7-amino-3- (N-phenylimino) methyl-3-cephem-4-carboxylic acid. 9. Способ получения цефалоспорина, при которой соединение формулы
Figure 00000005
VI
в которой R5 и R6 одинаковы или различны и обозначают водород или органическую группу, либо R5 и R6 вместе обозначают замещенное или незамещенное кольцо,
получают путем взаимодействия соединения формулы
Figure 00000006
Ia
в которой R обозначает силильную группу,
с соединением формулы
Figure 00000007
XI
или соединением формулы
Figure 00000008
XII
в которой R5 и R6 определены выше, R10 обозначает арил или низший алкил, а Cat+ обозначает катион щелочного металла или протонированную форму сильного органического основания, с образованием соединения формулы
Figure 00000009
XIII
в которой R, R5 и R6 определены выше, и десилилируют соединение формулы XIII с образованием соединения формулы VI и превращают соединение формулы VI в другой цефалоспорин.9. The method of obtaining cephalosporin, in which the compound of the formula
Figure 00000005
VI
in which R 5 and R 6 are the same or different and represent hydrogen or an organic group, or R 5 and R 6 together represent a substituted or unsubstituted ring,
obtained by reacting a compound of the formula
Figure 00000006
Ia
in which R denotes a silyl group,
with compound of formula
Figure 00000007
Xi
or a compound of the formula
Figure 00000008
Xii
in which R 5 and R 6 defined above, R 10 denotes aryl or lower alkyl, and Cat + denotes an alkali metal cation or protonated form of a strong organic base, with the formation of the compounds of the formula
Figure 00000009
XIII
in which R, R 5 and R 6 are as defined above, and the compound of formula XIII is desilylated to form a compound of formula VI and the compound of formula VI is converted to another cephalosporin.
RU96122784/04A 1994-04-25 1995-04-24 Intermediate derivative of cephalosporin and method of synthesis of cephalosporin RU2150471C1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
ATA858/94 1994-04-25
AT85794A AT402927B (en) 1994-04-25 1994-04-25 Novel cephalosporin derivatives, process for their preparation and their use
AT0085894A AT402072B (en) 1994-04-25 1994-04-25 Cephem derivatives and process for their preparation
ATA857/94 1994-04-25
ATA1066/94 1994-05-25
AT0106694A AT402929B (en) 1994-05-25 1994-05-25 Novel cephalosporin derivatives, process for their preparation and their use

Related Child Applications (1)

Application Number Title Priority Date Filing Date
RU99124184/04A Division RU2225411C2 (en) 1994-04-25 1995-04-24 Intermediate derivatives of cephalosporin and method for preparing cephalosporin

Publications (2)

Publication Number Publication Date
RU96122784A true RU96122784A (en) 1999-01-27
RU2150471C1 RU2150471C1 (en) 2000-06-10

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RU99124184/04A RU2225411C2 (en) 1994-04-25 1995-04-24 Intermediate derivatives of cephalosporin and method for preparing cephalosporin

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US (4) US5856474A (en)
EP (2) EP1340762B1 (en)
JP (1) JP3302369B2 (en)
KR (1) KR100487833B1 (en)
CN (3) CN1145628C (en)
AT (2) ATE498627T1 (en)
AU (1) AU686380B2 (en)
BR (1) BR9507512A (en)
CA (2) CA2533837A1 (en)
CY (1) CY2494B1 (en)
CZ (1) CZ297565B6 (en)
DE (2) DE69536140D1 (en)
DK (1) DK0757691T3 (en)
ES (1) ES2202362T3 (en)
FI (1) FI963761A (en)
HU (3) HU0102725D0 (en)
MX (1) MX9604353A (en)
NO (1) NO318020B1 (en)
NZ (2) NZ285084A (en)
PL (2) PL184773B1 (en)
PT (1) PT757691E (en)
RU (2) RU2150471C1 (en)
SI (1) SI0757691T1 (en)
SK (1) SK285948B6 (en)
TW (1) TW427992B (en)
WO (1) WO1995029182A1 (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248881B1 (en) * 1991-03-08 2001-06-19 Biochemie Gmbh Intermediates and process for the production of 3-vinyl cephalosporins
US5856474A (en) * 1994-04-25 1999-01-05 Biochemie Gesellschaft, M.B.H. Cephalosporin synthesis
DE60035925T2 (en) * 1999-07-05 2008-05-15 Basilea Pharmaceutica Ag Process for the preparation of cephalosporin derivatives
US6544555B2 (en) 2000-02-24 2003-04-08 Advancis Pharmaceutical Corp. Antibiotic product, use and formulation thereof
AU6701101A (en) 2000-06-21 2002-01-02 Cubist Pharm Inc Compositions and methods to improve the oral absorption of antimicrobial agents
US7527807B2 (en) * 2000-06-21 2009-05-05 Cubist Pharmaceuticals, Inc. Compositions and methods for increasing the oral absorption of antimicrobials
US20020068078A1 (en) 2000-10-13 2002-06-06 Rudnic Edward M. Antifungal product, use and formulation thereof
AU2004258944B2 (en) 2003-07-21 2011-02-10 Shionogi, Inc. Antibiotic product, use and formulation thereof
CA2533292C (en) 2003-07-21 2013-12-31 Advancis Pharmaceutical Corporation Antibiotic product, use and formulation thereof
CA2533178C (en) 2003-07-21 2014-03-11 Advancis Pharmaceutical Corporation Antibiotic product, use and formulation thereof
EP1653925A1 (en) 2003-08-11 2006-05-10 Advancis Pharmaceutical Corporation Robust pellet
JP2007502294A (en) 2003-08-12 2007-02-08 アドバンシス ファーマスーティカル コーポレイション Antibiotic preparations, their use and preparation
WO2005023184A2 (en) 2003-08-29 2005-03-17 Advancis Pharmaceuticals Corporation Antibiotic product, use and formulation thereof
CA2538064C (en) 2003-09-15 2013-12-17 Advancis Pharmaceutical Corporation Antibiotic product, use and formulation thereof
EP1771158A4 (en) 2004-07-02 2008-03-12 Advancis Pharmaceutical Corp Tablet for pulsed delivery
US8968781B2 (en) * 2005-04-29 2015-03-03 Cubist Pharmaceuticals, Inc. Therapeutic compositions
US8778924B2 (en) 2006-12-04 2014-07-15 Shionogi Inc. Modified release amoxicillin products
US8357394B2 (en) 2005-12-08 2013-01-22 Shionogi Inc. Compositions and methods for improved efficacy of penicillin-type antibiotics
US8299052B2 (en) 2006-05-05 2012-10-30 Shionogi Inc. Pharmaceutical compositions and methods for improved bacterial eradication
WO2010136422A1 (en) * 2009-05-25 2010-12-02 Sandoz Ag Method for the production of ceftobiprole medocaril
ITMI20131820A1 (en) * 2013-11-04 2015-05-05 Laboratorio Chimico Int Spa PROCEDURE FOR THE PREPARATION OF OLOPATADIN
CN109180704B (en) * 2018-11-19 2020-06-05 齐鲁安替制药有限公司 Synthesis method of cefditoren pivoxil
WO2021043973A1 (en) 2019-09-06 2021-03-11 Nabriva Therapeutics GmbH Siderophore cephalosporin conjugates and uses thereof

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3351596A (en) * 1966-09-21 1967-11-07 Lilly Co Eli 3-formyl cephalosporins
CH556876A (en) * 1971-05-19 1974-12-13 Ciba Geigy Ag 3-Formyl-7-amino-ceph-3-em-4-oate esters - with cleavable ester gps., prepd. by sulphoxide-anhydride oxidn. of the 3-hydroxymethyl cpds.
CH546794A (en) * 1970-06-18 1974-03-15 Ciba Geigy Ag PROCESS FOR THE PRODUCTION OF CEPHALOSPORANIC ACID DERIVATIVES.
US3674784A (en) * 1970-07-27 1972-07-04 Lilly Co Eli 3-formyl cephalosporin sulfoxides
GB1368231A (en) * 1970-07-31 1974-09-25 Glaxo Lab Ltd Thio-substituted azetidinones and thiazolino azetidinones
US3880851A (en) * 1971-12-24 1975-04-29 Lilly Co Eli Antibiotic method
CA1109860A (en) * 1972-12-08 1981-09-29 Shinji Terao Process for producing lactol-type cephalosporins
JPS49109391A (en) * 1973-02-28 1974-10-17
JPS5093989A (en) * 1973-10-25 1975-07-26
JPS5071691A (en) * 1973-11-02 1975-06-13
JPS5129492A (en) * 1974-09-04 1976-03-12 Sankyo Co Sefuarosuhorinjudotai no seiho
GB1447959A (en) * 1975-02-27 1976-09-02 Shionogi & Co Process for preparing cephem aldehyde derivatives
US4101658A (en) * 1975-06-04 1978-07-18 Shionogi & Co., Ltd. Antibacterial hydrazono cephalosporins
GB8821797D0 (en) * 1988-09-16 1988-10-19 Beecham Group Plc Novel compounds
US5081116A (en) 1989-04-12 1992-01-14 Yamanouchi Pharmaceutical Co., Ltd. Cephalosporin derivatives
JP2895900B2 (en) * 1990-03-08 1999-05-24 大塚化学株式会社 Method for producing 3-formylsefm derivative
AT400436B (en) * 1992-11-10 1995-12-27 Biochemie Gmbh NEW METHOD FOR PRODUCING 3-VINYLCEPHALOSPORINE COMPOUNDS
DE69231815T2 (en) * 1991-03-08 2001-09-27 Biochemie Gmbh Process for the preparation of cephalosporins and intermediates in this process
ES2185634T3 (en) 1993-04-16 2003-05-01 Basilea Pharmaceutica Ag CEPHALOSPORINE DERIVATIVES
US5856474A (en) * 1994-04-25 1999-01-05 Biochemie Gesellschaft, M.B.H. Cephalosporin synthesis

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