RU2056425C1 - Производные цефалоспорина или их фармацевтически приемлемые кислотно-аддитивные соли и способы их получения - Google Patents
Производные цефалоспорина или их фармацевтически приемлемые кислотно-аддитивные соли и способы их получения Download PDFInfo
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- RU2056425C1 RU2056425C1 SU853878102A SU3878102A RU2056425C1 RU 2056425 C1 RU2056425 C1 RU 2056425C1 SU 853878102 A SU853878102 A SU 853878102A SU 3878102 A SU3878102 A SU 3878102A RU 2056425 C1 RU2056425 C1 RU 2056425C1
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- 238000000034 method Methods 0.000 title claims abstract description 36
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 10
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- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 9
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- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 5
- 239000000654 additive Substances 0.000 title 1
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 48
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 28
- 125000006239 protecting group Chemical group 0.000 claims description 26
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 9
- 239000003242 anti bacterial agent Substances 0.000 abstract description 3
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 201
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- 125000000217 alkyl group Chemical group 0.000 description 95
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- 238000002360 preparation method Methods 0.000 description 60
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 52
- 230000002829 reductive effect Effects 0.000 description 51
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 48
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
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- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 150000002431 hydrogen Chemical class 0.000 description 22
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 235000019341 magnesium sulphate Nutrition 0.000 description 22
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
- 239000012071 phase Substances 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 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 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 229910052736 halogen Inorganic materials 0.000 description 19
- 150000002367 halogens Chemical class 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 230000002441 reversible effect Effects 0.000 description 19
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- 239000002904 solvent Substances 0.000 description 19
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 125000003342 alkenyl group Chemical group 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
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- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000004484 Briquette Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
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- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
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- 238000005406 washing Methods 0.000 description 11
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- 0 NC1SCC(CC(C2)*2C(C2)(*CC2=O)S)C1 Chemical compound NC1SCC(CC(C2)*2C(C2)(*CC2=O)S)C1 0.000 description 8
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- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 101150065749 Churc1 gene Proteins 0.000 description 7
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
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- HQKIQQSTJMDYIA-NBXNUCLWSA-N benzhydryl (6R)-7-[[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-3-(3-iodoprop-1-enyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound NC1=NC(=NS1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)C=CCI)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O)=NOC HQKIQQSTJMDYIA-NBXNUCLWSA-N 0.000 description 5
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- WKHGDPZRLXDVMJ-UHFFFAOYSA-N tert-butyl n-pyridin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CN=C1 WKHGDPZRLXDVMJ-UHFFFAOYSA-N 0.000 description 1
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Images
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59794184A | 1984-04-09 | 1984-04-09 | |
| US597941 | 1984-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2056425C1 true RU2056425C1 (ru) | 1996-03-20 |
Family
ID=24393575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU853878102A RU2056425C1 (ru) | 1984-04-09 | 1985-04-08 | Производные цефалоспорина или их фармацевтически приемлемые кислотно-аддитивные соли и способы их получения |
Country Status (31)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61145186A (ja) * | 1984-12-20 | 1986-07-02 | Meiji Seika Kaisha Ltd | 新規セフエム化合物及びその製造法 |
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| ATE114657T1 (de) * | 1985-12-26 | 1994-12-15 | Eisai Co Ltd | Cephalosporin-verbindungen. |
| AU614723B2 (en) * | 1986-10-13 | 1991-09-12 | Eisai Co. Ltd. | 3-propenylcephem derivative |
| IL84128A (en) * | 1986-10-13 | 1992-12-01 | Eisai Co Ltd | 3-propenylcephem derivatives, their preparation and pharmaceutical compositions containing them |
| JPH085897B2 (ja) * | 1986-11-06 | 1996-01-24 | エーザイ株式会社 | ３−プロペニルセフェム誘導体 |
| 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 |
| JPH0699449B2 (ja) * | 1988-03-16 | 1994-12-07 | エーザイ株式会社 | セフェム誘導体の合成中間体 |
| CA1339738C (en) * | 1988-03-16 | 1998-03-17 | Takashi Kamiya | Process for the preparation of cephem derivatives and entermediates therefor |
| FR2655042B1 (fr) * | 1989-11-29 | 1994-01-21 | Adir Cie | Nouvelles benzothiazolinones substituees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2663332B1 (fr) * | 1990-06-15 | 1997-11-07 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 3 un radical propenyle substitue par un ammonium quaternaire, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. |
| US5126336A (en) * | 1990-08-23 | 1992-06-30 | Bristol-Myers Squibb Company | Antibiotic c-3 catechol-substituted cephalosporin compounds, compositions and method of use thereof |
| AT396108B (de) * | 1991-08-21 | 1993-06-25 | Biochemie Gmbh | Neues verfahren und neue zwischenprodukte zur herstellung von 7-aminocephalosporansaeurederivaten |
| JPH0741484A (ja) * | 1993-07-29 | 1995-02-10 | Katayama Seiyakushiyo:Kk | セフェム化合物及び抗菌剤 |
| KR100248851B1 (ko) * | 1994-08-16 | 2000-04-01 | 이치로 키타사토 | 신규 세펨 유도체 |
| TR200003807T2 (tr) | 1998-06-22 | 2001-06-21 | Basilea Pharmaceutica Ag | Propenil sefalosporin türevleri |
| EP1666483B1 (en) | 2003-09-09 | 2011-08-17 | Nippon Chemical Industrial Company Limited | Process for producing 3-chloromethyl-3-cephem derivative |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1342241A (en) * | 1970-01-23 | 1974-01-03 | Glaxo Lab Ltd | Cephalosporin compounds |
| US4390534A (en) * | 1978-12-29 | 1983-06-28 | Fujisawa Pharmaceutical Co., Ltd. | Cephem and cepham compounds |
| EP0025017A1 (de) * | 1979-08-28 | 1981-03-11 | Ciba-Geigy Ag | Polyazathiaverbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend solche Verbindungen und Verwendung von letzteren |
| US4409214A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| GR75644B (enrdf_load_stackoverflow) * | 1980-06-18 | 1984-08-02 | Fujisawa Pharmaceutical Co | |
| GR78245B (enrdf_load_stackoverflow) * | 1980-09-12 | 1984-09-26 | Ciba Geigy Ag | |
| US4521413A (en) * | 1981-09-14 | 1985-06-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
-
1985
- 1985-02-14 CA CA000474260A patent/CA1276929C/en not_active Expired - Lifetime
- 1985-03-25 ZA ZA852236A patent/ZA852236B/xx unknown
- 1985-04-02 AR AR85299945A patent/AR244694A1/es active
- 1985-04-02 NZ NZ211659A patent/NZ211659A/xx unknown
- 1985-04-03 DK DK155985A patent/DK155985A/da not_active Application Discontinuation
- 1985-04-03 SE SE8501680A patent/SE466205B/sv not_active IP Right Cessation
- 1985-04-03 DD DD85274832A patent/DD236735A5/de unknown
- 1985-04-03 DE DE19853512225 patent/DE3512225A1/de active Granted
- 1985-04-03 DD DD85287524A patent/DD249024A5/de unknown
- 1985-04-04 NL NL8501002A patent/NL192925C/nl not_active IP Right Cessation
- 1985-04-04 PT PT80246A patent/PT80246B/pt unknown
- 1985-04-04 FI FI851379A patent/FI84830C/fi not_active IP Right Cessation
- 1985-04-04 GB GB08508846A patent/GB2157293B/en not_active Expired
- 1985-04-04 CH CH1498/85A patent/CH669197A5/de not_active IP Right Cessation
- 1985-04-04 AU AU40862/85A patent/AU580990B2/en not_active Expired
- 1985-04-04 OA OA58561A patent/OA07985A/xx unknown
- 1985-04-04 IE IE86685A patent/IE58408B1/en not_active IP Right Cessation
- 1985-04-05 FR FR8505281A patent/FR2563832B1/fr not_active Expired
- 1985-04-05 IT IT20267/85A patent/IT1190353B/it active
- 1985-04-05 LU LU85840A patent/LU85840A1/fr unknown
- 1985-04-05 AT AT0103985A patent/AT388735B/de not_active IP Right Cessation
- 1985-04-05 IL IL74826A patent/IL74826A/xx not_active IP Right Cessation
- 1985-04-08 GR GR850883A patent/GR850883B/el not_active IP Right Cessation
- 1985-04-08 RU SU853878102A patent/RU2056425C1/ru active
- 1985-04-08 ES ES542013A patent/ES8607318A1/es not_active Expired
- 1985-04-09 KR KR1019850002383A patent/KR870002166B1/ko not_active Expired
- 1985-04-09 HU HU87151A patent/HU204277B/hu unknown
- 1985-04-09 YU YU60085A patent/YU46151B/sh unknown
- 1985-04-09 HU HU851299A patent/HU193750B/hu unknown
- 1985-04-09 BE BE0/214810A patent/BE902148A/fr not_active IP Right Cessation
- 1985-04-09 JP JP60075233A patent/JPS615084A/ja active Granted
- 1985-11-12 JP JP60252138A patent/JPS61143390A/ja active Granted
- 1985-11-12 JP JP60252139A patent/JPS61143391A/ja active Granted
- 1985-11-12 JP JP60252140A patent/JPS61143387A/ja active Granted
-
1986
- 1986-01-31 ES ES551550A patent/ES8706155A1/es not_active Expired
- 1986-01-31 ES ES551551A patent/ES8706694A1/es not_active Expired
- 1986-02-06 SU SU864019975A patent/SU1487814A3/ru active
- 1986-02-06 SU SU864018257A patent/SU1375140A3/ru active
- 1986-02-06 SU SU864023036A patent/SU1367858A3/ru active
- 1986-02-06 SU SU864020682A patent/SU1436882A3/ru active
- 1986-03-03 DD DD86287525A patent/DD251752A5/de unknown
- 1986-09-10 ES ES557060A patent/ES8800949A1/es not_active Expired
-
1987
- 1987-06-25 YU YU118987A patent/YU46213B/sh unknown
- 1987-09-10 GB GB08721347A patent/GB2194790B/en not_active Expired
- 1987-09-10 GB GB08721346A patent/GB2194789B/en not_active Expired
- 1987-10-01 MY MYPI87002761A patent/MY101940A/en unknown
-
1988
- 1988-11-11 AU AU25041/88A patent/AU610278B2/en not_active Expired
-
1989
- 1989-04-04 IE IE121089A patent/IE58403B1/en not_active IP Right Cessation
- 1989-04-06 SE SE8901226A patent/SE470260B/sv not_active IP Right Cessation
- 1989-04-06 SE SE8901224A patent/SE470259B/sv not_active IP Right Cessation
- 1989-04-06 SE SE8901225A patent/SE505256C2/sv not_active IP Right Cessation
-
1991
- 1991-08-12 CA CA000616143A patent/CA1340638C/en not_active Expired - Fee Related
- 1991-08-21 CA CA000616144A patent/CA1340672C/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 1. Европейская заявка N 0062321, кл. C 07D 501/46, 1982. 2. Европейская заявка N 0074653, кл. C 07D 501/46, 1983. 3. Заявка Японии Kokai N 57-112396, кл. C 07D 501/46, 1982. * |
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