SU932986A3 - Способ получени 7-/2-(2-аминотиазолил-4)-2-оксииминоацетамидо/-3/ацетоксиметил-3-цефем-4-карбоновой кислоты или ее солей с щелочными металлами - Google Patents

Способ получени 7-/2-(2-аминотиазолил-4)-2-оксииминоацетамидо/-3/ацетоксиметил-3-цефем-4-карбоновой кислоты или ее солей с щелочными металлами Download PDF

Info

Publication number: SU932986A3
Authority: SU; USSR - Soviet Union
Prior art keywords: acid; product; hydrogenolysis; isomer; water
Prior art date: 1977-03-11

Application number

SU802949072A

Other languages

English (en)

Russian (ru)

Inventor

Эйме Рене

Лютц Андре

Original Assignee

Руссель-Юклаф (Фирма)

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.)

1977-03-11

Filing date

1980-07-21

Publication date

1982-05-30

1977-03-11 Priority claimed from FR7707307A external-priority patent/FR2383188A2/fr

1980-07-21 Application filed by Руссель-Юклаф (Фирма) filed Critical Руссель-Юклаф (Фирма)

1982-05-30 Application granted granted Critical

1982-05-30 Publication of SU932986A3 publication Critical patent/SU932986A3/ru

1994-09-08 Priority to MD94-0269A priority Critical patent/MD228C2/ro

Links

229910052783 alkali metal Inorganic materials 0.000 title claims description 3
-1 alkali metal salts Chemical class 0.000 title description 12
238000000034 method Methods 0.000 title description 4
239000002253 acid Substances 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 17
238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 13
238000007327 hydrogenolysis reaction Methods 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims abstract description 3
239000003795 chemical substances by application Substances 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 2
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims 1
229950003476 aminothiazole Drugs 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract description 7
238000006243 chemical reaction Methods 0.000 abstract description 6
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract 2
125000000217 alkyl group Chemical group 0.000 abstract 2
125000000304 alkynyl group Chemical group 0.000 abstract 2
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 abstract 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
239000003242 anti bacterial agent Substances 0.000 abstract 1
229940088710 antibiotic agent Drugs 0.000 abstract 1
230000001580 bacterial effect Effects 0.000 abstract 1
125000004432 carbon atom Chemical group C* 0.000 abstract 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
239000000047 product Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
239000000243 solution Substances 0.000 description 17
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 15
159000000000 sodium salts Chemical class 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
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 8
238000003756 stirring Methods 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000012453 solvate Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 4
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 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 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
230000009466 transformation Effects 0.000 description 2
125000006000 trichloroethyl group Chemical group 0.000 description 2
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 2
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
JHXOAXMCYMGJLQ-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazol-2-amine Chemical compound NC1NC=CS1 JHXOAXMCYMGJLQ-UHFFFAOYSA-N 0.000 description 1
FJPNAQRDSFZHJM-UHFFFAOYSA-N 2-(oxan-2-yloxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound C=1SC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C(C(=O)O)=NOC1CCCCO1 FJPNAQRDSFZHJM-UHFFFAOYSA-N 0.000 description 1
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
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 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
YCRZCIAGZISABO-UHFFFAOYSA-N butanoic acid ethanol hydrate Chemical compound O.CCO.CCCC(O)=O YCRZCIAGZISABO-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
DRWMGJONTCWKES-UHFFFAOYSA-N chloroform;hydrochloride Chemical compound Cl.ClC(Cl)Cl DRWMGJONTCWKES-UHFFFAOYSA-N 0.000 description 1
239000012141 concentrate Substances 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
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
150000005332 diethylamines Chemical class 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
KKFBLNMRJSAFAA-UHFFFAOYSA-N ethyl 2-hydroxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=NO)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 KKFBLNMRJSAFAA-UHFFFAOYSA-N 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
229910052722 tritium Inorganic materials 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

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
- C07D501/26—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)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU802949072A 1977-01-18 1980-07-21 Способ получени 7-/2-(2-аминотиазолил-4)-2-оксииминоацетамидо/-3/ацетоксиметил-3-цефем-4-карбоновой кислоты или ее солей с щелочными металлами SU932986A3 (ru)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
MD94-0269A MD228C2 (ro)	1977-01-18	1994-09-08	Procedeu de obţinere a acidului 7-ő2-(2-aminotiazolil-4)-2-oximiinoacetamidoo-3-acetoximetil-3-cefem-4-carbonic sau a sărurilor lui cu metale alcaline

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7707307A FR2383188A2 (fr)	1976-01-23	1977-03-11	Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments

Publications (1)

Publication Number	Publication Date
SU932986A3 true SU932986A3 (ru)	1982-05-30

Family

ID=9187972

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU802949072A SU932986A3 (ru)	1977-01-18	1980-07-21	Способ получени 7-/2-(2-аминотиазолил-4)-2-оксииминоацетамидо/-3/ацетоксиметил-3-цефем-4-карбоновой кислоты или ее солей с щелочными металлами

Country Status (14)

Country	Link
AT (1)	AT357672B (de)
AU (1)	AU511864B2 (de)
CH (1)	CH619234A5 (de)
CS (1)	CS207576B2 (de)
EG (1)	EG12997A (de)
GE (1)	GEP19960530B (de)
IT (1)	IT1115958B (de)
MX (1)	MX4959E (de)
NL (1)	NL7703615A (de)
PL (1)	PL124946B3 (de)
SE (1)	SE7703776L (de)
SU (1)	SU932986A3 (de)
YU (1)	YU89877A (de)
ZA (1)	ZA772331B (de)

1977
- 1977-03-22 CH CH361877A patent/CH619234A5/fr not_active IP Right Cessation
- 1977-03-31 SE SE7703776A patent/SE7703776L/xx unknown
- 1977-03-31 IT IT48771/77A patent/IT1115958B/it active
- 1977-04-01 PL PL1977197138A patent/PL124946B3/pl unknown
- 1977-04-01 NL NL7703615A patent/NL7703615A/xx not_active Application Discontinuation
- 1977-04-04 EG EG186/77A patent/EG12997A/xx active
- 1977-04-05 YU YU00898/77A patent/YU89877A/xx unknown
- 1977-04-18 ZA ZA00772331A patent/ZA772331B/xx unknown
- 1977-04-26 MX MX775661U patent/MX4959E/es unknown
- 1977-10-12 AU AU29622/77A patent/AU511864B2/en not_active Expired
1978
- 1978-03-11 CS CS781544A patent/CS207576B2/cs unknown
- 1978-04-14 AT AT263478A patent/AT357672B/de not_active IP Right Cessation
1980
- 1980-07-21 SU SU802949072A patent/SU932986A3/ru active
1993
- 1993-07-31 GE GEAP19931356A patent/GEP19960530B/en unknown

Also Published As

Publication number	Publication date
IT1115958B (it)	1986-02-10
SE7703776L (sv)	1978-09-12
PL124946B3 (en)	1983-03-31
NL7703615A (nl)	1978-09-13
AU511864B2 (en)	1980-09-11
ATA263478A (de)	1979-12-15
CH619234A5 (en)	1980-09-15
AU2962277A (en)	1979-04-26
CS207576B2 (en)	1981-08-31
PL197138A1 (pl)	1979-09-10
MX4959E (es)	1983-01-18
AT357672B (de)	1980-07-25
YU89877A (en)	1983-10-31
EG12997A (en)	1981-03-31
ZA772331B (en)	1978-06-28
GEP19960530B (en)	1996-07-19

Publication	Publication Date	Title
SU795482A3 (ru)	1981-01-07	Способ получени производных7-/2-(2-АМиНОТиАзОлил-4)-2-АлКОКСи-иМиНОАцЕТАМидО/-3-ТиОМЕТил-3-цЕфЕМ- 4-КАРбОНОВОй КиСлОТы B ВидЕ СиН- изОМЕРОВ
MC1921A1 (fr)	1989-04-06	Derives acyles
JPH0362711B2 (de)	1991-09-26
GB1599722A (en)	1981-10-07	Cephalosporin derivatives
US3840531A (en)	1974-10-08	Process for preparing 7-(alpha-hydroxy-alpha-phenyl)acetamido-3-(1-methyl-1h-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and derivatives thereof
EP0763043A1 (de)	1997-03-19	Verfahren zur herstellung von cefixime trihydrat
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