HU181961B - Process for producing new oxime derivatives of 3-thiadiazolythio-methyl-7-aminothiazolylacetamido-ceph-3-eme-4-carboxylic acids - Google Patents
Process for producing new oxime derivatives of 3-thiadiazolythio-methyl-7-aminothiazolylacetamido-ceph-3-eme-4-carboxylic acids Download PDFInfo
- Publication number
- HU181961B HU181961B HU78RO963A HURO000963A HU181961B HU 181961 B HU181961 B HU 181961B HU 78RO963 A HU78RO963 A HU 78RO963A HU RO000963 A HURO000963 A HU RO000963A HU 181961 B HU181961 B HU 181961B
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- compound
- methoxy
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- acid
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- 238000000034 method Methods 0.000 title claims description 17
- 150000002923 oximes Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 73
- -1 2-amino-4-thiazolyl Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 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 claims description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 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 claims description 3
- 238000004458 analytical method Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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- 239000000203 mixture Substances 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- 208000015181 infectious disease Diseases 0.000 description 6
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- 238000003828 vacuum filtration Methods 0.000 description 4
- FUWXWRNWTLNQGG-UHFFFAOYSA-N 3-methoxy-2h-1,2,4-thiadiazole-5-thione Chemical compound COC1=NC(=S)SN1 FUWXWRNWTLNQGG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
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- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 3
- 229930182566 Gentamicin Natural products 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
- 241000607142 Salmonella Species 0.000 description 3
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- 239000002585 base Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
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- 229910052749 magnesium Inorganic materials 0.000 description 3
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- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- COOBWTPWNZVKKV-WCRCJTMVSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(3-methoxy-1,2,4-thiadiazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NC(=NS2)OC)C(=O)O)C1=O)=NOC COOBWTPWNZVKKV-WCRCJTMVSA-N 0.000 description 2
- BWXZKORFJLHYBP-XCGJVMPOSA-N (6R)-7-amino-3-[(3-methoxy-1,2,4-thiadiazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC1[C@@H]2N(C(=C(CS2)CSC2=NC(=NS2)OC)C(=O)O)C1=O BWXZKORFJLHYBP-XCGJVMPOSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
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- 206010035664 Pneumonia Diseases 0.000 description 2
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
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- 239000004098 Tetracycline Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
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- 102000006635 beta-lactamase Human genes 0.000 description 2
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- 239000007903 gelatin capsule Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
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- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- PKPGSMOHYWOGJR-UHFFFAOYSA-N 2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound CON=C(C(O)=O)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 PKPGSMOHYWOGJR-UHFFFAOYSA-N 0.000 description 1
- GYGNJEASCVSRLC-UHFFFAOYSA-N 5-chloro-3-methoxy-1,2,4-thiadiazole Chemical compound COC1=NSC(Cl)=N1 GYGNJEASCVSRLC-UHFFFAOYSA-N 0.000 description 1
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- DSODRWWHAUGSGD-UHFFFAOYSA-N [5-(carbamimidoylsulfanylmethyl)thiophen-2-yl]methyl carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.NC(=N)SCC1=CC=C(CSC(N)=N)S1 DSODRWWHAUGSGD-UHFFFAOYSA-N 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7704745A FR2381053A1 (fr) | 1977-02-18 | 1977-02-18 | Nouvelles oximes derivees de l'acide 3-thiadiazolyl thiomethyl 7-aminothiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU181961B true HU181961B (en) | 1983-11-28 |
Family
ID=9186946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU78RO963A HU181961B (en) | 1977-02-18 | 1978-02-17 | Process for producing new oxime derivatives of 3-thiadiazolythio-methyl-7-aminothiazolylacetamido-ceph-3-eme-4-carboxylic acids |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS53108996A (en:Method) |
| AT (1) | AT355722B (en:Method) |
| AU (1) | AU516076B2 (en:Method) |
| BE (1) | BE864074A (en:Method) |
| CA (1) | CA1132537A (en:Method) |
| CH (1) | CH633016A5 (en:Method) |
| DE (1) | DE2806226A1 (en:Method) |
| DK (1) | DK68978A (en:Method) |
| ES (2) | ES467090A1 (en:Method) |
| FI (1) | FI69468C (en:Method) |
| FR (1) | FR2381053A1 (en:Method) |
| GB (1) | GB1575180A (en:Method) |
| GR (1) | GR71703B (en:Method) |
| HU (1) | HU181961B (en:Method) |
| IE (1) | IE46651B1 (en:Method) |
| IL (1) | IL54043A (en:Method) |
| LU (1) | LU79080A1 (en:Method) |
| NL (1) | NL7801834A (en:Method) |
| PT (1) | PT67673B (en:Method) |
| SE (1) | SE434268B (en:Method) |
| SU (1) | SU841590A3 (en:Method) |
| YU (1) | YU41583B (en:Method) |
| ZA (1) | ZA78847B (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE878433A (fr) * | 1978-08-31 | 1980-02-25 | Fujisawa Pharmaceutical Co | Procede de preparation de derives d'acide 3-cephem-4-carboxylique 3,7-disubstitue, nouveaux produits ainsi obtenus et leur utilisation pour leur activite antibacterienne |
| BE878514A (fr) * | 1978-09-04 | 1980-02-29 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3-cephem-4-carboxylique a disubstitution en positions 3 et 7, nouveaux produits ainsi obtenus et leur utilisation pour leur activite antibacterienne |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| US4341775A (en) * | 1978-09-11 | 1982-07-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| DE2945248A1 (de) * | 1978-11-13 | 1980-05-22 | Fujisawa Pharmaceutical Co | Cephem-verbindungen, verfahren zu ihrer herstellung und sie enthaltende antibakterielle pharmazeutische mittel |
| CH642957A5 (de) | 1980-02-18 | 1984-05-15 | Lonza Ag | Verfahren zur herstellung von (2-aminothiazol-4-yl)-essigsaeure-hydrochlorid. |
| US4399132A (en) * | 1980-08-11 | 1983-08-16 | American Cyanamid Company | 7-Beta-[alpha-syn-methoxyimino-alpha-(2-aminothiazol-4-yl)-acetamido]-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylic acid and C1 -C6 alkyl derivatives thereof |
| US4761409A (en) * | 1984-08-16 | 1988-08-02 | Sumitomo Pharmaceuticals Company, Limited | Cephem derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| 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 |
| DK162391C (da) * | 1976-04-12 | 1992-03-09 | Fujisawa Pharmaceutical Co | Analogifremgangsmaade til fremstilling af syn-isomerer af 3,7-disubstituerede 3-cephem-4-carboxylsyreforbindelser |
| DE2715385A1 (de) * | 1976-04-14 | 1977-11-10 | Takeda Chemical Industries Ltd | Cephalosporinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
-
1977
- 1977-02-18 FR FR7704745A patent/FR2381053A1/fr active Granted
-
1978
- 1978-01-23 SE SE7800790A patent/SE434268B/sv not_active IP Right Cessation
- 1978-02-10 FI FI780444A patent/FI69468C/fi not_active IP Right Cessation
- 1978-02-13 ZA ZA00780847A patent/ZA78847B/xx unknown
- 1978-02-13 IL IL54043A patent/IL54043A/xx unknown
- 1978-02-14 DE DE19782806226 patent/DE2806226A1/de not_active Withdrawn
- 1978-02-14 SU SU782578251A patent/SU841590A3/ru active
- 1978-02-14 YU YU336/78A patent/YU41583B/xx unknown
- 1978-02-16 DK DK68978A patent/DK68978A/da not_active Application Discontinuation
- 1978-02-16 GR GR55474A patent/GR71703B/el unknown
- 1978-02-17 JP JP1666578A patent/JPS53108996A/ja active Pending
- 1978-02-17 LU LU79080A patent/LU79080A1/xx unknown
- 1978-02-17 PT PT67673A patent/PT67673B/pt unknown
- 1978-02-17 CH CH178978A patent/CH633016A5/fr not_active IP Right Cessation
- 1978-02-17 AU AU33375/78A patent/AU516076B2/en not_active Expired
- 1978-02-17 ES ES467090A patent/ES467090A1/es not_active Expired
- 1978-02-17 CA CA297,248A patent/CA1132537A/fr not_active Expired
- 1978-02-17 BE BE185267A patent/BE864074A/xx not_active IP Right Cessation
- 1978-02-17 NL NL7801834A patent/NL7801834A/xx not_active Application Discontinuation
- 1978-02-17 HU HU78RO963A patent/HU181961B/hu unknown
- 1978-02-20 IE IE364/78A patent/IE46651B1/en unknown
- 1978-02-20 AT AT120978A patent/AT355722B/de not_active IP Right Cessation
- 1978-02-20 GB GB6621/78A patent/GB1575180A/en not_active Expired
- 1978-12-13 ES ES475956A patent/ES475956A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU79080A1 (fr) | 1978-09-28 |
| GR71703B (en:Method) | 1983-06-21 |
| ES467090A1 (es) | 1979-06-01 |
| DK68978A (da) | 1978-08-19 |
| SU841590A3 (ru) | 1981-06-23 |
| FR2381053B1 (en:Method) | 1979-06-01 |
| SE434268B (sv) | 1984-07-16 |
| GB1575180A (en) | 1980-09-17 |
| CA1132537A (fr) | 1982-09-28 |
| PT67673A (fr) | 1978-03-01 |
| SE7800790L (sv) | 1978-08-19 |
| IL54043A0 (en) | 1978-04-30 |
| NL7801834A (nl) | 1978-08-22 |
| AU516076B2 (en) | 1981-05-14 |
| FI780444A7 (fi) | 1978-08-19 |
| AU3337578A (en) | 1979-08-23 |
| IL54043A (en) | 1983-02-23 |
| ATA120978A (de) | 1979-08-15 |
| ZA78847B (en) | 1979-03-28 |
| ES475956A1 (es) | 1979-12-16 |
| FR2381053A1 (fr) | 1978-09-15 |
| BE864074A (fr) | 1978-08-17 |
| CH633016A5 (en) | 1982-11-15 |
| FI69468B (fi) | 1985-10-31 |
| JPS53108996A (en) | 1978-09-22 |
| FI69468C (fi) | 1986-02-10 |
| YU41583B (en) | 1987-10-31 |
| AT355722B (de) | 1980-03-25 |
| YU33678A (en) | 1983-01-21 |
| IE46651B1 (en) | 1983-08-10 |
| DE2806226A1 (de) | 1978-08-24 |
| PT67673B (fr) | 1980-03-03 |
| IE780364L (en) | 1978-08-18 |
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