SU1424736A3 - Способ получени замещенных производных имидазола или их нетоксичных аддитивных солей с кислотами - Google Patents
Способ получени замещенных производных имидазола или их нетоксичных аддитивных солей с кислотами Download PDFInfo
- Publication number
- SU1424736A3 SU1424736A3 SU853979907A SU3979907A SU1424736A3 SU 1424736 A3 SU1424736 A3 SU 1424736A3 SU 853979907 A SU853979907 A SU 853979907A SU 3979907 A SU3979907 A SU 3979907A SU 1424736 A3 SU1424736 A3 SU 1424736A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compound
- imidazole
- general formula
- acids
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 4
- 150000003839 salts Chemical class 0.000 title claims abstract description 4
- 239000002253 acid Substances 0.000 title claims abstract 3
- 150000007513 acids Chemical class 0.000 title claims abstract 3
- 239000000654 additive Substances 0.000 title claims abstract 3
- 230000000996 additive effect Effects 0.000 title claims abstract 3
- 231100000252 nontoxic Toxicity 0.000 title claims abstract 3
- 230000003000 nontoxic effect Effects 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 230000026030 halogenation Effects 0.000 claims abstract 2
- 238000005658 halogenation reaction Methods 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims abstract 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 2
- HPMRFMKYPGXPEP-UHFFFAOYSA-N idazoxan Chemical compound N1CCN=C1C1OC2=CC=CC=C2OC1 HPMRFMKYPGXPEP-UHFFFAOYSA-N 0.000 claims 1
- 229950001476 idazoxan Drugs 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 125000006519 CCH3 Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000005557 antagonist Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JXMXDKHEZLKQPB-UHFFFAOYSA-N detomidine Chemical compound CC1=CC=CC(CC=2[N]C=NC=2)=C1C JXMXDKHEZLKQPB-UHFFFAOYSA-N 0.000 description 6
- 229960001894 detomidine Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000004118 muscle contraction Effects 0.000 description 2
- 210000001747 pupil Anatomy 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- -1 2,3-Dihydro-1H-inden-2-yl Chemical group 0.000 description 1
- VXZBYIWNGKSFOJ-UHFFFAOYSA-N 2-[4-[5-(2,3-dihydro-1H-inden-2-ylamino)pyrazin-2-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC=1N=CC(=NC=1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 VXZBYIWNGKSFOJ-UHFFFAOYSA-N 0.000 description 1
- QUIWSCUJFRGKMD-UHFFFAOYSA-N 2-acetyl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(C(=O)C)CC2=C1 QUIWSCUJFRGKMD-UHFFFAOYSA-N 0.000 description 1
- YAENKTFGFXAVKD-UHFFFAOYSA-N 2-acetyl-2-ethyl-3h-inden-1-one Chemical compound C1=CC=C2C(=O)C(CC)(C(C)=O)CC2=C1 YAENKTFGFXAVKD-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N deuterated acetone Substances [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 238000002086 displacement chromatography Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FZJCXIDLUFPGPP-UHFFFAOYSA-N propan-2-ol;toluene Chemical compound CC(C)O.CC1=CC=CC=C1 FZJCXIDLUFPGPP-UHFFFAOYSA-N 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Resins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Dental Preparations (AREA)
- Golf Clubs (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LV920316A LV5064A3 (lv) | 1984-11-23 | 1992-12-17 | Aizvietotu imidazola atvasinajumu vai to netoksisku skabju-aditivo salu iegusanas metode |
| LTRP768A LT2220B (lt) | 1984-11-23 | 1993-07-07 | Pavaduotu imidazolo dariniu ir ju netoksiniu drusku gavimo budas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08429578A GB2167408B (en) | 1984-11-23 | 1984-11-23 | Substituted imidazole derivatives and their preparation and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1424736A3 true SU1424736A3 (ru) | 1988-09-15 |
Family
ID=10570140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU853979907A SU1424736A3 (ru) | 1984-11-23 | 1985-11-22 | Способ получени замещенных производных имидазола или их нетоксичных аддитивных солей с кислотами |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4689339A (enExample) |
| EP (2) | EP0310745B1 (enExample) |
| JP (1) | JPH064597B2 (enExample) |
| KR (1) | KR930004673B1 (enExample) |
| AT (2) | ATE85050T1 (enExample) |
| AU (2) | AU586839B2 (enExample) |
| BG (1) | BG60762B2 (enExample) |
| CA (1) | CA1268770C (enExample) |
| DD (1) | DD258230A1 (enExample) |
| DE (2) | DE3587045T2 (enExample) |
| DK (2) | DK164903C (enExample) |
| ES (2) | ES8704462A1 (enExample) |
| FI (1) | FI80264C (enExample) |
| GB (1) | GB2167408B (enExample) |
| GR (1) | GR852817B (enExample) |
| HK (1) | HK3592A (enExample) |
| HU (1) | HU195189B (enExample) |
| IE (1) | IE58165B1 (enExample) |
| IL (1) | IL77111A (enExample) |
| NO (1) | NO166585C (enExample) |
| NZ (1) | NZ214258A (enExample) |
| PH (1) | PH22016A (enExample) |
| PT (1) | PT81542B (enExample) |
| SG (1) | SG106891G (enExample) |
| SU (1) | SU1424736A3 (enExample) |
| ZA (1) | ZA858942B (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4891431A (en) * | 1986-01-28 | 1990-01-02 | Mitsui Petrochemical Industries, Ltd. | Process for preparing 2-unsubstituted imidazoles |
| FI862039A0 (fi) * | 1986-05-15 | 1986-05-15 | Farmos Oy | Nytt foerfarande foer framstaellning av 4(5)-substituerade imidazolderivat. |
| FI81092C (fi) * | 1986-05-15 | 1990-09-10 | Farmos Oy | Foerfarande foer framstaellning av terapeutiskt aktiva 4(5)-(2,3-dihydro-1h-inden-2-yl)-imidazolderivat. |
| JP2576493B2 (ja) * | 1987-03-20 | 1997-01-29 | アイシン精機株式会社 | 原稿読取り装置に用いられる原稿トレ− |
| FR2621327B1 (fr) * | 1987-10-06 | 1990-01-05 | Commissariat Energie Atomique | Procede de production et d'extraction de polysaccharides a partir d'une culture de porphyridium cruentum et dispositif pour la mise en oeuvre du procede |
| GB2225782A (en) * | 1988-12-09 | 1990-06-13 | Farmos Group Limited | Imidazole derivatives useful for treatment of diabetes |
| GB8903437D0 (en) * | 1989-02-15 | 1989-04-05 | Erba Carlo Spa | Imidazolyl derivatives of 3,4-dihydro-2h-1-benzothiopyran |
| CA1321751C (en) * | 1989-02-21 | 1993-08-31 | Eugene C. Crichlow | Mechanism mediating ruminal stasis in ruminal lactic acidosis |
| DK344489D0 (da) * | 1989-07-12 | 1989-07-12 | Novo Nordisk As | Substituerede 2-imidazoliner og fremstilling og anvendelse deraf |
| GB2244431A (en) * | 1990-05-31 | 1991-12-04 | Farmos Oy | Treatment of age related memory impairment and other cognitive disorders |
| GB2256135B (en) | 1991-05-31 | 1995-01-18 | Orion Yhtymae Oy | Transdermal administration of 4-substituted imidazoles |
| US5541211A (en) * | 1991-06-18 | 1996-07-30 | Orion-Yhtyma Oy | Administration of atipamezole to elicit a yohimbine-like alpha-adrenoreceptor antagonistic noradrenergic transmission |
| CZ287406B6 (cs) * | 1991-11-05 | 2000-11-15 | Smithkline Beecham Corporation | Indanové a indenové deriváty, způsob jejich výroby a farmaceutické prostředky s jejich obsahem |
| GB9127050D0 (en) * | 1991-12-20 | 1992-02-19 | Orion Yhtymae Oy | Substituted imidazole derivatives and their preparation and use |
| GB9127430D0 (en) * | 1991-12-27 | 1992-02-19 | Scras | Benzofuranylimidazole derivatives |
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- 1985-11-20 AU AU50083/85A patent/AU586839B2/en not_active Expired
- 1985-11-20 DD DD85283044A patent/DD258230A1/de not_active IP Right Cessation
- 1985-11-21 EP EP88106210A patent/EP0310745B1/en not_active Expired - Lifetime
- 1985-11-21 KR KR1019850008704A patent/KR930004673B1/ko not_active Expired - Fee Related
- 1985-11-21 EP EP85308491A patent/EP0183492B1/en not_active Expired
- 1985-11-21 AT AT88106210T patent/ATE85050T1/de not_active IP Right Cessation
- 1985-11-21 US US06/800,192 patent/US4689339A/en not_active Expired - Lifetime
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- 1985-11-21 PH PH33077A patent/PH22016A/en unknown
- 1985-11-21 ZA ZA858942A patent/ZA858942B/xx unknown
- 1985-11-21 GR GR852817A patent/GR852817B/el unknown
- 1985-11-21 DE DE8888106210T patent/DE3587045T2/de not_active Expired - Fee Related
- 1985-11-21 DE DE8585308491T patent/DE3574252D1/de not_active Expired
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- 1985-11-22 DK DK540485A patent/DK164903C/da not_active IP Right Cessation
- 1985-11-22 SU SU853979907A patent/SU1424736A3/ru active
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- 1985-11-22 JP JP60263586A patent/JPH064597B2/ja not_active Expired - Lifetime
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