SU1600632A3 - Способ получени производных гризеоловой кислоты - Google Patents
Способ получени производных гризеоловой кислоты Download PDFInfo
- Publication number
- SU1600632A3 SU1600632A3 SU843808501A SU3808501A SU1600632A3 SU 1600632 A3 SU1600632 A3 SU 1600632A3 SU 843808501 A SU843808501 A SU 843808501A SU 3808501 A SU3808501 A SU 3808501A SU 1600632 A3 SU1600632 A3 SU 1600632A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- singlet
- doublet
- formula
- graseoil
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- IAPZXUKYTCQQFE-QZKDJMESSA-N (2r,3r,3as,5s)-2-(6-aminopurin-9-yl)-5-[carboxy(hydroxy)methyl]-3-hydroxy-3,3a-dihydro-2h-furo[3,2-b]furan-5-carboxylic acid Chemical class NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@@H]2O[C@](C(O)=O)(C(O)C(O)=O)C=C2O1 IAPZXUKYTCQQFE-QZKDJMESSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 13
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229960000278 theophylline Drugs 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- -1 nitro, benzhydryl Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 abstract 1
- IAPZXUKYTCQQFE-UHFFFAOYSA-N Griseolic acid Natural products NC1=NC=NC2=C1N=CN2C1C(O)C2OC(C(O)=O)(C(O)C(O)=O)C=C2O1 IAPZXUKYTCQQFE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 6
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 1
- 235000013928 guanylic acid Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Insulating Materials (AREA)
- Fats And Perfumes (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58202362A JPS6094992A (ja) | 1983-10-28 | 1983-10-28 | グリゼオ−ル酸誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1600632A3 true SU1600632A3 (ru) | 1990-10-15 |
Family
ID=16456245
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843808501A SU1600632A3 (ru) | 1983-10-28 | 1984-10-26 | Способ получени производных гризеоловой кислоты |
| SU853960265A SU1604158A3 (ru) | 1983-10-28 | 1985-10-03 | Способ получени производных гризеоловой кислоты |
| SU853962054A SU1468422A3 (ru) | 1983-10-28 | 1985-10-03 | Способ получени производных гризеоловой кислоты |
| SU853961256A SU1468421A3 (ru) | 1983-10-28 | 1985-10-03 | Способ получени 6-дезамино-6-гризеоловой кислоты |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU853960265A SU1604158A3 (ru) | 1983-10-28 | 1985-10-03 | Способ получени производных гризеоловой кислоты |
| SU853962054A SU1468422A3 (ru) | 1983-10-28 | 1985-10-03 | Способ получени производных гризеоловой кислоты |
| SU853961256A SU1468421A3 (ru) | 1983-10-28 | 1985-10-03 | Способ получени 6-дезамино-6-гризеоловой кислоты |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4634706A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0143557B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS6094992A (cg-RX-API-DMAC7.html) |
| KR (1) | KR930000165B1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE39357T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1267408A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3475714D1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK166323C (cg-RX-API-DMAC7.html) |
| ES (4) | ES8604737A1 (cg-RX-API-DMAC7.html) |
| FI (1) | FI81357C (cg-RX-API-DMAC7.html) |
| NO (1) | NO164904C (cg-RX-API-DMAC7.html) |
| SU (4) | SU1600632A3 (cg-RX-API-DMAC7.html) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4783532A (en) * | 1983-10-28 | 1988-11-08 | Sankyo Company Limited | Process for preparing griseolic acid derivatives |
| IT1196261B (it) * | 1984-09-20 | 1988-11-16 | Pierrel Spa | Derivati nucleosidici e purinici 8-sostituiti |
| ATE48611T1 (de) | 1985-04-19 | 1989-12-15 | Sankyo Co | Griseolinsaeurederivate, ihre herstellung und ihre verwendung. |
| FI94133C (fi) * | 1985-04-19 | 1995-07-25 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten griseoliinihapon johdannaisten valmistamiseksi |
| JPH0631307B2 (ja) * | 1985-04-27 | 1994-04-27 | 三共株式会社 | グリゼオ−ル酸誘導体の製法 |
| US5214048A (en) * | 1987-05-19 | 1993-05-25 | Nippon Kayaku Kabushiki Kaisha | Oxetanocins |
| JPH0774229B2 (ja) * | 1987-12-02 | 1995-08-09 | 三共株式会社 | グリゼオール酸モノエステル誘導体 |
| US5091431A (en) * | 1988-02-08 | 1992-02-25 | Schering Corporation | Phosphodiesterase inhibitors |
| JPH0689020B2 (ja) * | 1988-06-30 | 1994-11-09 | 三共株式会社 | グリゼオール酸のモノエステル誘導体 |
| US4971972A (en) * | 1989-03-23 | 1990-11-20 | Schering Corporation | Phosphodiesterase inhibitors having an optionally substituted purine derivative portion and a benzo- or cyclopenta-furan portion |
| JP3645580B2 (ja) * | 1993-10-22 | 2005-05-11 | 株式会社フジモト・ブラザーズ | グルコースエステル誘導体を含有する脳代謝改善剤 |
| US6291516B1 (en) * | 1999-01-13 | 2001-09-18 | Curis, Inc. | Regulators of the hedgehog pathway, compositions and uses related thereto |
| EP1312363A1 (en) * | 2001-09-28 | 2003-05-21 | Pfizer Products Inc. | Methods of treatment and kits comprising a growth hormone secretagogue |
| US7342884B2 (en) * | 2002-03-13 | 2008-03-11 | Harmonic, Inc. | Method and apparatus for one directional communications in bidirectional communications channel |
| US20110190192A1 (en) * | 2009-12-15 | 2011-08-04 | Cebix Inc. | Methods for treating erectile dysfunction in patients with insulin-dependent diabetes |
| EP4163000B1 (en) * | 2021-02-19 | 2024-04-10 | Anhui Jinhe Industrial Co., Ltd. | Production apparatus and production method for sucrose-6-ester |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862189A (en) * | 1973-08-14 | 1975-01-21 | Warner Lambert Co | Aralkyl-substituted purines and pyrimidines as antianginal bronchodilator agents |
| GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
| US4138562A (en) * | 1977-02-09 | 1979-02-06 | The Regents Of The University Of Minnesota | Adenosine deaminase resistant antiviral purine nucleosides and method of preparation |
| JPS5668695A (en) * | 1979-11-10 | 1981-06-09 | Sankyo Co Ltd | Enzyme inhibitor griseolic acid and its preparation |
| DE3028273A1 (de) * | 1980-07-25 | 1982-02-25 | Fa. Dr. Willmar Schwabe, 7500 Karlsruhe | Durch purinbasen substituierte 1.4;3.6-dianhydro-hexit-nitrate |
| JPS60246396A (ja) * | 1984-05-22 | 1985-12-06 | Sankyo Co Ltd | 酵素阻害物質ジヒドロデスオキシグリゼオ−ル酸及びその塩類 |
-
1983
- 1983-10-28 JP JP58202362A patent/JPS6094992A/ja active Granted
-
1984
- 1984-10-25 US US06/664,866 patent/US4634706A/en not_active Expired - Fee Related
- 1984-10-26 DK DK513384A patent/DK166323C/da not_active IP Right Cessation
- 1984-10-26 SU SU843808501A patent/SU1600632A3/ru active
- 1984-10-26 ES ES537154A patent/ES8604737A1/es not_active Expired
- 1984-10-26 FI FI844225A patent/FI81357C/fi not_active IP Right Cessation
- 1984-10-27 KR KR1019840006706A patent/KR930000165B1/ko not_active Expired - Fee Related
- 1984-10-29 AT AT84307436T patent/ATE39357T1/de not_active IP Right Cessation
- 1984-10-29 DE DE8484307436T patent/DE3475714D1/de not_active Expired
- 1984-10-29 CA CA000466527A patent/CA1267408A/en not_active Expired - Fee Related
- 1984-10-29 EP EP84307436A patent/EP0143557B1/en not_active Expired
- 1984-10-29 NO NO844291A patent/NO164904C/no unknown
-
1985
- 1985-09-25 ES ES547291A patent/ES8701193A1/es not_active Expired
- 1985-09-25 ES ES547292A patent/ES8604981A1/es not_active Expired
- 1985-09-26 ES ES547347A patent/ES8700673A1/es not_active Expired
- 1985-10-03 SU SU853960265A patent/SU1604158A3/ru active
- 1985-10-03 SU SU853962054A patent/SU1468422A3/ru active
- 1985-10-03 SU SU853961256A patent/SU1468421A3/ru active
Non-Patent Citations (1)
| Title |
|---|
| Вейганд-Хильгетаг. Современные методы эксперимента в органической химии. М.: Хими , 1964, с.432. * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6094992A (ja) | 1985-05-28 |
| FI81357B (fi) | 1990-06-29 |
| DK513384A (da) | 1985-04-29 |
| NO164904B (no) | 1990-08-20 |
| ES547292A0 (es) | 1986-02-16 |
| ES8700673A1 (es) | 1986-10-16 |
| DK513384D0 (da) | 1984-10-26 |
| FI844225A0 (fi) | 1984-10-26 |
| ATE39357T1 (de) | 1989-01-15 |
| EP0143557B1 (en) | 1988-12-21 |
| SU1468421A3 (ru) | 1989-03-23 |
| ES8701193A1 (es) | 1986-11-16 |
| KR850003415A (ko) | 1985-06-17 |
| US4634706A (en) | 1987-01-06 |
| DK166323B (da) | 1993-04-05 |
| FI844225L (fi) | 1985-04-29 |
| CA1267408A (en) | 1990-04-03 |
| JPH0432837B2 (cg-RX-API-DMAC7.html) | 1992-06-01 |
| ES547291A0 (es) | 1986-11-16 |
| EP0143557A2 (en) | 1985-06-05 |
| ES537154A0 (es) | 1985-12-01 |
| KR930000165B1 (ko) | 1993-01-11 |
| ES547347A0 (es) | 1986-10-16 |
| SU1604158A3 (ru) | 1990-10-30 |
| ES8604737A1 (es) | 1985-12-01 |
| FI81357C (fi) | 1990-10-10 |
| DE3475714D1 (en) | 1989-01-26 |
| SU1468422A3 (ru) | 1989-03-23 |
| DK166323C (da) | 1993-08-30 |
| ES8604981A1 (es) | 1986-02-16 |
| EP0143557A3 (en) | 1985-07-03 |
| NO844291L (no) | 1985-04-29 |
| NO164904C (no) | 1990-11-28 |
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