IL92810A - תהליך אצילציה של תולדות צפם וחומר ביניים לתהליך זה - Google Patents

תהליך אצילציה של תולדות צפם וחומר ביניים לתהליך זה

Info

Publication number: IL92810A
Authority: IL; Israel
Prior art keywords: compound; formula; acid; nucleus; mixed
Prior art date: 1988-12-27

Application number

IL9281089A

Other languages

English (en)

Original Assignee

Lilly Co Eli

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-12-27

Filing date

1989-12-20

Publication date

1994-12-29

1989-12-20 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1994-12-29 Publication of IL92810A publication Critical patent/IL92810A/he

Links

238000000034 method Methods 0.000 title claims description 32
230000010933 acylation Effects 0.000 title description 15
238000005917 acylation reaction Methods 0.000 title description 15
238000002360 preparation method Methods 0.000 title description 5
150000001782 cephems Chemical class 0.000 title description 2
150000008064 anhydrides Chemical class 0.000 claims description 33
-1 amino pyridinium compound Chemical class 0.000 claims description 10
239000003960 organic solvent Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000005059 halophenyl group Chemical group 0.000 claims description 6
125000003944 tolyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
229910019142 PO4 Inorganic materials 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
239000010452 phosphate Substances 0.000 claims description 2
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims 1
ORFOPKXBNMVMKC-CEZXYXJGSA-N (6S,7S)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CC(C)(O\N=C(/C(=O)N[C@@H]1[C@@H]2SCC(C[n+]3ccccc3)=C(N2C1=O)C([O-])=O)c1csc(N)n1)C(O)=O ORFOPKXBNMVMKC-CEZXYXJGSA-N 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
229960000484 ceftazidime Drugs 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000012453 solvate Substances 0.000 description 9
239000002002 slurry Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
230000003115 biocidal effect Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
238000010268 HPLC based assay Methods 0.000 description 4
230000006181 N-acylation Effects 0.000 description 4
229960004132 diethyl ether Drugs 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZSIAANIILFGLQH-UHFFFAOYSA-N C1(=CC=CC=C1)[ClH]P(=O)(Cl)[ClH]C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)[ClH]P(=O)(Cl)[ClH]C1=CC=CC=C1 ZSIAANIILFGLQH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 1
NCLIGEZQAPUUQU-UHFFFAOYSA-N 2-silylacetamide Chemical compound NC(=O)C[SiH3] NCLIGEZQAPUUQU-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
PHIMQSCHTGNBCG-UHFFFAOYSA-N 3-trimethylsilyl-1,3-oxazolidin-2-id-4-one Chemical compound C[Si](N1[CH-]OCC1=O)(C)C PHIMQSCHTGNBCG-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
TVMUHOAONWHJBV-UHFFFAOYSA-N dehydroglycine Chemical compound OC(=O)C=N TVMUHOAONWHJBV-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
CKQQMPJQZXIYMJ-UHFFFAOYSA-N dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl CKQQMPJQZXIYMJ-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
LHMRVAWTCGBZLK-UHFFFAOYSA-N n-trityl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)NC1=NC=CS1 LHMRVAWTCGBZLK-UHFFFAOYSA-N 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical class BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical class BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003513 tertiary aromatic amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 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 description 1
238000005303 weighing Methods 0.000 description 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
- C07D501/38—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
- C07D501/46—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 with the 7-amino radical acylated by carboxylic acids containing hetero rings
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Cephalosporin Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

IL9281089A 1988-12-27 1989-12-20 תהליך אצילציה של תולדות צפם וחומר ביניים לתהליך זה IL92810A (he)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US29068088A	1988-12-27	1988-12-27

Publications (1)

Publication Number	Publication Date
IL92810A true IL92810A (he)	1994-12-29

Family

ID=23117097

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9281089A IL92810A (he)	1988-12-27	1989-12-20	תהליך אצילציה של תולדות צפם וחומר ביניים לתהליך זה

Country Status (5)

Country	Link
EP (1)	EP0377987A3 (he)
JP (1)	JP3068143B2 (he)
KR (2)	KR0159760B1 (he)
CA (1)	CA2006341A1 (he)
IL (1)	IL92810A (he)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR950013578B1 (ko) *	1993-04-10	1995-11-09	주식회사럭키	신규 티아(디아)졸 초산의 반응성 티오포스페이트 유도체 및 그의 제조방법
EP0791596A1 (en) *	1996-02-21	1997-08-27	Lupin Laboratories Limited	Method for manufacture of cephalosporins and intermediates thereof
EP0791597B1 (en) *	1996-02-21	2000-07-12	Lupin Laboratories Limited	Method for manufacture of cephalosporins and intermediates thereof
US5831085A (en) *	1997-01-16	1998-11-03	Lupin Laboratories Limited	Process for manufacture of cephalosporin such as ceftazidime and intermediate thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR229883A1 (es) *	1978-05-26	1983-12-30	Glaxo Group Ltd	Procedimiento para la preparacion de antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)-acetamido)-3-(1-piridinometil)-cef-3-em-4-carboxilato
FR2439785A1 (fr) *	1978-10-23	1980-05-23	Roussel Uclaf	Nouveau procede de preparation des produits derives de l'acide 7-amino-thiazolyl acetamido cephalosporanique
FR2462439A1 (fr) *	1979-07-26	1981-02-13	Roussel Uclaf	Nouveau procede de preparation de produits derives de l'acide 7-/(2-aryl) 2-hydroxyimino acetamido/cephalosporanique
DE3419015A1 (de) *	1984-05-22	1985-11-28	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von cephalosporinen
DE3542644A1 (de) *	1985-12-03	1987-06-04	Hoechst Ag	Verfahren zur herstellung von cefodizim

1989
- 1989-12-20 KR KR1019890019012A patent/KR0159760B1/ko not_active IP Right Cessation
- 1989-12-20 IL IL9281089A patent/IL92810A/he unknown
- 1989-12-20 EP EP19890313373 patent/EP0377987A3/en not_active Withdrawn
- 1989-12-21 CA CA002006341A patent/CA2006341A1/en not_active Abandoned
- 1989-12-22 JP JP1334678A patent/JP3068143B2/ja not_active Expired - Lifetime
1998
- 1998-04-25 KR KR1019980014866A patent/KR0180907B1/ko not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0377987A2 (en)	1990-07-18
KR0159760B1 (ko)	1998-12-01
EP0377987A3 (en)	1991-08-28
CA2006341A1 (en)	1990-06-27
KR900009658A (ko)	1990-07-05
JPH02215786A (ja)	1990-08-28
JP3068143B2 (ja)	2000-07-24
KR0180907B1 (ko)	1999-10-01

Legal Events

Date	Code	Title	Description
2000-06-01	KB	Patent renewed

Publication	Publication Date	Title
EP0286145A2 (en)	1988-10-12	3-Heterocyclylthiomethyl cephalosporins
CS247081B2 (en)	1986-11-13	Production method of cefemderivatives
EP0188255A2 (en)	1986-07-23	Cephem derivatives
IL92810A (he)	1994-12-29	תהליך אצילציה של תולדות צפם וחומר ביניים לתהליך זה
EP0175814B1 (en)	1990-05-23	Process for preparing cephem derivatives
US5502200A (en)	1996-03-26	Reactive thiophosphate derivatives of thia(dia)zole acetic acid and process for preparing the same
EP0533047B1 (en)	2003-05-07	Preparation of a cephalosporin antibiotic using the synisomer of a thiazolyl intermediate
EP0246603B1 (en)	1992-12-30	4-halogeno-2-oxyimino-3-oxobutyric acids
FI109127B (fi)	2002-05-31	Menetelmä kefepiimidihydrokloridihydraattiantibiootin valmistamiseksi
EP0613480B1 (en)	1999-03-31	Process for the preparation of cephem derivatives
WO1991009037A1 (en)	1991-06-27	Process for producing 3-substituted thio-3-cephem compound
JP2905775B2 (ja)	1999-06-14	セファロスポリン誘導体の製造のための反応試薬
US5159071A (en)	1992-10-27	Process for the manufacture of 7-amino-3-exomethylene-3-cepham-4-carboxylic acid ester
EP0117872A1 (en)	1984-09-12	Process for preparing cephalosporin compounds
US5563264A (en)	1996-10-08	Preparation of βlactam compounds
KR0161351B1 (ko)	1998-12-01	신규 티아(디아)졸 초산의 반응성 포스페이트 유도체 및 그의 제조방법
KR0129567B1 (ko)	1998-04-09	반응성 유기산 유도체로부터 세팔로스포린 화합물의 제조방법
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EP0253507B1 (en)	1994-03-23	Process for the preparation of cephalosporins
EP0045717B1 (en)	1985-09-25	New cephalosporin derivatives, their production and their use
US5831085A (en)	1998-11-03	Process for manufacture of cephalosporin such as ceftazidime and intermediate thereof
KR20010002705A (ko)	2001-01-15	신규 티아졸 초산의 반응성 포스페이트 유도체의 제조방법
KR950013571B1 (ko)	1995-11-09	(6r, 7r)-7-[(z)-2-(2-아미노티아졸-4-일)-2-(2-카르복시프로프-2-옥시이미노)아세트아미도]-3-(1-피리디늄메틸)세프-3-엠-4-카르복실레이트 이염산염의 제조방법
US4665168A (en)	1987-05-12	Cephalosporin intermediate
KR870001333B1 (ko)	1987-07-18	세펨 유도체의 간단한 제조방법