BG60762B2 - Заместени имидазолови производни и тяхното получаване и приложение - Google Patents
Заместени имидазолови производни и тяхното получаване и приложение Download PDFInfo
- Publication number
- BG60762B2 BG60762B2 BG098378A BG9837894A BG60762B2 BG 60762 B2 BG60762 B2 BG 60762B2 BG 098378 A BG098378 A BG 098378A BG 9837894 A BG9837894 A BG 9837894A BG 60762 B2 BG60762 B2 BG 60762B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- imidazole
- dihydro
- inden
- compound
- methyl
- Prior art date
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- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 106
- 238000000034 method Methods 0.000 claims abstract description 48
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 6
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 6
- 239000003937 drug carrier Substances 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 3
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 52
- -1 2,3-dihydro-2-ethyl-5-methyl- 1 H-inden-2-yl Chemical group 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 26
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 22
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 230000026030 halogenation Effects 0.000 claims description 5
- 238000005658 halogenation reaction Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- KBHBZXLVSVKQLI-UHFFFAOYSA-N 2-imidazol-1-yl-2,3-dihydro-1h-inden-1-ol Chemical compound C1C2=CC=CC=C2C(O)C1N1C=CN=C1 KBHBZXLVSVKQLI-UHFFFAOYSA-N 0.000 claims 1
- BUJXACDGHOVJSB-UHFFFAOYSA-N C1C(CC2=C1C=CC(=C2)Br)N3C=CN=C3 Chemical compound C1C(CC2=C1C=CC(=C2)Br)N3C=CN=C3 BUJXACDGHOVJSB-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229920000137 polyphosphoric acid Polymers 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
- 238000005481 NMR spectroscopy Methods 0.000 description 65
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000000203 mixture Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- JXMXDKHEZLKQPB-UHFFFAOYSA-N detomidine Chemical compound CC1=CC=CC(CC=2[N]C=NC=2)=C1C JXMXDKHEZLKQPB-UHFFFAOYSA-N 0.000 description 19
- 229960001894 detomidine Drugs 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000005557 antagonist Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000012043 crude product Substances 0.000 description 10
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 125000001246 bromo group Chemical group Br* 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000556 agonist Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 6
- OJGQVOARYFNMJA-UHFFFAOYSA-N 2-ethyl-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1=CC=C2CC(CC)(C(O)=O)CCC2=C1 OJGQVOARYFNMJA-UHFFFAOYSA-N 0.000 description 6
- TUKGSBTVYWYLDH-UHFFFAOYSA-N 3,7-dimethyl-1h-indene-2-carboxylic acid Chemical compound C1=CC=C(C)C2=C1C(C)=C(C(O)=O)C2 TUKGSBTVYWYLDH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 229960002748 norepinephrine Drugs 0.000 description 6
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 6
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 5
- 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 5
- RBEKONHDQBHXEG-UHFFFAOYSA-N 2-bromo-1-(2-bromo-1-methyl-1,3-dihydroinden-2-yl)ethanone Chemical compound C1=CC=C2CC(C(=O)CBr)(Br)C(C)C2=C1 RBEKONHDQBHXEG-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XUDCMQBOWOLYCF-UHFFFAOYSA-N 2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)CC2=C1 XUDCMQBOWOLYCF-UHFFFAOYSA-N 0.000 description 4
- OIKDESVHCFBNCU-UHFFFAOYSA-N 2-bromo-1-(3,7-dimethyl-1h-inden-2-yl)ethanone Chemical compound C1=CC=C(C)C2=C1C(C)=C(C(=O)CBr)C2 OIKDESVHCFBNCU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
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- 229960001802 phenylephrine Drugs 0.000 description 4
- 229960001289 prazosin Drugs 0.000 description 4
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- VQEDMDWIBFEVTB-UHFFFAOYSA-N 1-(2-ethyl-1-methyl-1,3-dihydroinden-2-yl)ethanone Chemical compound C1=CC=C2C(C)C(CC)(C(C)=O)CC2=C1 VQEDMDWIBFEVTB-UHFFFAOYSA-N 0.000 description 3
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- 150000003892 tartrate salts Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000002618 waking effect Effects 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)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Golf Clubs (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Dental Preparations (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Resins (AREA)
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 |
---|---|
BG60762B2 true BG60762B2 (bg) | 1996-02-29 |
Family
ID=10570140
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG098378A BG60762B2 (bg) | 1984-11-23 | 1994-01-18 | Заместени имидазолови производни и тяхното получаване и приложение |
Country Status (26)
Country | Link |
---|---|
US (1) | US4689339A (fr) |
EP (2) | EP0183492B1 (fr) |
JP (1) | JPH064597B2 (fr) |
KR (1) | KR930004673B1 (fr) |
AT (2) | ATE85050T1 (fr) |
AU (2) | AU586839B2 (fr) |
BG (1) | BG60762B2 (fr) |
CA (1) | CA1268770C (fr) |
DD (1) | DD258230A1 (fr) |
DE (2) | DE3587045T2 (fr) |
DK (2) | DK164903C (fr) |
ES (2) | ES8704462A1 (fr) |
FI (1) | FI80264C (fr) |
GB (1) | GB2167408B (fr) |
GR (1) | GR852817B (fr) |
HK (1) | HK3592A (fr) |
HU (1) | HU195189B (fr) |
IE (1) | IE58165B1 (fr) |
IL (1) | IL77111A (fr) |
NO (1) | NO166585C (fr) |
NZ (1) | NZ214258A (fr) |
PH (1) | PH22016A (fr) |
PT (1) | PT81542B (fr) |
SG (1) | SG106891G (fr) |
SU (1) | SU1424736A3 (fr) |
ZA (1) | ZA858942B (fr) |
Families Citing this family (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1987004431A1 (fr) * | 1986-01-28 | 1987-07-30 | Mitsui Petrochemical Industries, Ltd. | Procede de preparation de 2-imidazoles non substitues |
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. |
FI862039A0 (fi) * | 1986-05-15 | 1986-05-15 | Farmos Oy | Nytt foerfarande foer framstaellning av 4(5)-substituerade 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 (fr) * | 1989-02-21 | 1993-08-31 | Eugene C. Crichlow | Mecanisme mediatisant la stase ruminale dans l'acidose lactique ruminale |
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 |
AU669866B2 (en) * | 1991-11-05 | 1996-06-27 | Smithkline Beecham Corporation | Endothelin receptor antagonists |
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 |
GB9312669D0 (en) * | 1993-06-18 | 1993-08-04 | Orion Yhtymae Oy | New opticla isomers |
GB9425211D0 (en) * | 1994-12-14 | 1995-02-15 | Ucb Sa | Substituted 1H-imidazoles |
FR2733983B1 (fr) * | 1995-05-10 | 1997-08-01 | Pf Medicament | Procede de preparation d'un derive d'acide benzofurane carboxylque optiquement pur et son utilisation pour preparer l'efaroxan |
GB9520150D0 (en) * | 1995-10-03 | 1995-12-06 | Orion Yhtymae Oy | New imidazole derivatives |
FR2754709B1 (fr) | 1996-10-23 | 1999-03-05 | Sanofi Sa | Composition cosmetique contenant un antagoniste des recepteurs du neuropeptide gamma et alpha 2 antagonistes susceptibles d'etre incorpores dans une telle composition |
EP0986530A1 (fr) | 1997-06-05 | 2000-03-22 | Venantius Limited | Composes d'indane et leur utilisation pharmaceutique |
WO1999051593A1 (fr) * | 1998-04-02 | 1999-10-14 | Ortho-Mcneil Pharmaceutical, Inc. | 4-thionaphtyl-1h-imidazoles ayant une activite recepteur alpha-2-adrenergique |
FR2784989B1 (fr) * | 1998-09-10 | 2002-09-27 | Fabre Pierre Sante | Derive d'ester d'acide 2-ethyl-2,3-dihydrobenzofurane- carboxylique, procede de preparation et utilisation pour la preparation de derives de l'efaroxan |
JP2002534511A (ja) * | 1999-01-18 | 2002-10-15 | ノボ ノルディスク アクティーゼルスカブ | 置換型イミダゾール、それらの調製及び使用 |
US6388090B2 (en) | 2000-01-14 | 2002-05-14 | Orion Corporation | Imidazole derivatives |
US6593324B2 (en) | 2000-03-01 | 2003-07-15 | Orion Corporation | Dervatives of quinoline as alpha-2 antagonists |
WO2001085698A1 (fr) | 2000-05-08 | 2001-11-15 | Orion Corporation | Indanylimidazoles polycycliques a activite alpha2 adrenergique |
US6503894B1 (en) | 2000-08-30 | 2003-01-07 | Unimed Pharmaceuticals, Inc. | Pharmaceutical composition and method for treating hypogonadism |
US6543389B2 (en) | 2001-06-26 | 2003-04-08 | Pfizer Inc. | Insecticidal pet collar |
PL372657A1 (en) | 2002-04-03 | 2005-07-25 | Orion Corporation | Polycyclic compounds as potent alpha2-adrenoceptor antagonists |
US8188126B2 (en) | 2002-05-16 | 2012-05-29 | Pierre Fabre Medicament | Imidazolic compounds and use thereof as alpha-2 adrenergic receptors |
FI116292B (fi) * | 2003-01-08 | 2005-10-31 | Juvantia Pharma Ltd Oy | Menetelmä substituoitujen imidatsolijohdannaisten valmistamiseksi ja menetelmässä käytettäviä välituotteita |
DE602004017347D1 (de) * | 2003-11-04 | 2008-12-04 | Intervet Int Bv | Azol-pestiziden |
FI20050657A0 (fi) * | 2005-06-17 | 2005-06-17 | Orion Corp | Atipametsolin kiteytysmenetelmä |
BRPI0617294B8 (pt) | 2005-10-12 | 2021-05-25 | Besins Healthcare Lu Sarl | composição farmacêutica em gel hidroalcóolico e uso de testosterona |
US7592461B2 (en) | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
ES2341138T3 (es) * | 2006-08-08 | 2010-06-15 | Intervet International Bv | Composicion con actividad antiparasitaria mejorada. |
TWI457122B (zh) | 2007-07-20 | 2014-10-21 | Orion Corp | 作為用於治療周邊和中央神經系統疾病之alpha2C拮抗劑的2,3-二氫苯並[1,4]戴奧辛-2-基甲基衍生物 |
CL2008003553A1 (es) * | 2007-12-05 | 2009-11-27 | Grindeks Jsc | Proceso para preparar atipamezol o clorhidrato de 5-(2-etil-2,3-dihidro-1h-inden-2-il)-1h-imidazol: y loa compuestos intermediarios considerados en el proceso |
PE20160849A1 (es) | 2013-11-05 | 2016-09-14 | 3M Innovative Properties Co | Formulaciones de inyeccion con base en aceite de sesamo |
TWI704145B (zh) | 2015-06-05 | 2020-09-11 | 芬蘭商奧利安公司 | 新醫藥化合物 |
WO2017079734A1 (fr) * | 2015-11-05 | 2017-05-11 | University Of Louisville Research Foundation, Inc. | Anesthésie et analgésie locales et régionales |
EA201990158A1 (ru) | 2016-06-29 | 2019-05-31 | Орион Корпорейшн | Производные бензодиоксана и их фармацевтическое применение |
US20220072107A1 (en) | 2018-12-21 | 2022-03-10 | Societe Des Produits Nestle S.A. | Nutritional composition for inducing a feeling of satiety, a better sleep and/or limiting nocturnal awaking in infants or young children |
CN111978254A (zh) * | 2019-05-22 | 2020-11-24 | 南京康德祥医药科技有限公司 | 一种阿替美唑盐酸盐的制备工艺 |
CN111925330A (zh) * | 2020-09-07 | 2020-11-13 | 上海阿达玛斯试剂有限公司 | 一种阿替美唑的制备方法 |
WO2024160908A1 (fr) | 2023-02-01 | 2024-08-08 | Univerza V Ljubljani | N, n-dialkyl-4-(2-éthylindan-2-yl)-1h-imidazole-1-carboxamides et composés apparentés pour le traitement de maladies neurodégénératives |
LU103072B1 (en) | 2023-02-15 | 2024-08-19 | Univ Ljubljani | N,N-DIALKYL-4-(2-ETHYLINDAN-2-YL)-lH-IMIDAZOLE-l-CARBOXAMIDES AND RELATED COMPOUNDS FOR TREATMENT OF NEURODEGENERATIVE DISEASES |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2933962A1 (de) * | 1979-08-22 | 1981-03-26 | Hoechst Ag, 65929 Frankfurt | Verfahren zur herstellung von 4,5-dichlor-imidazolen. |
IL62122A0 (en) * | 1980-03-04 | 1981-03-31 | Erba Farmitalia | N-imidazolyl derivatives of 1-chroman,their preparation and pharmaceutical compositions containing them |
US4302469A (en) * | 1980-09-10 | 1981-11-24 | Syntex (U.S.A.) Inc. | 2-(1,4-Benzodioxan-2-ylalkyl)imidazoles useful as antidepressants |
ZW13782A1 (en) * | 1981-07-28 | 1982-10-06 | Reckitt & Colmann Prod Ltd | Imidazoline derivatives |
ES8503669A1 (es) * | 1982-07-05 | 1985-03-01 | Erba Farmitalia | Procedimiento para preparar derivados n-imidazolilicos de compuestos biciclicos. |
FR2539415B1 (fr) * | 1983-01-14 | 1985-09-13 | Adir | Derives de la d-2 imidazoline, leur preparation et leur application en therapeutique |
FR2542738A1 (fr) * | 1983-03-18 | 1984-09-21 | Synthelabo | Indanyl-2 d2-imidazoline, procede pour la preparer, et compositions pharmaceutiques qui la contiennent |
-
1984
- 1984-11-23 GB GB08429578A patent/GB2167408B/en not_active Expired
-
1985
- 1985-11-05 FI FI854335A patent/FI80264C/fi not_active IP Right Cessation
- 1985-11-18 CA CA 495608 patent/CA1268770C/fr not_active Expired - Lifetime
- 1985-11-20 AU AU50083/85A patent/AU586839B2/en not_active Expired
- 1985-11-20 NZ NZ214258A patent/NZ214258A/xx unknown
- 1985-11-20 DD DD85283044A patent/DD258230A1/de not_active IP Right Cessation
- 1985-11-20 IL IL77111A patent/IL77111A/xx not_active IP Right Cessation
- 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 US US06/800,192 patent/US4689339A/en not_active Expired - Lifetime
- 1985-11-21 AT AT88106210T patent/ATE85050T1/de not_active IP Right Cessation
- 1985-11-21 EP EP85308491A patent/EP0183492B1/fr not_active Expired
- 1985-11-21 EP EP88106210A patent/EP0310745B1/fr not_active Expired - Lifetime
- 1985-11-21 IE IE292985A patent/IE58165B1/en not_active IP Right Cessation
- 1985-11-21 KR KR1019850008704A patent/KR930004673B1/ko not_active IP Right Cessation
- 1985-11-21 ZA ZA858942A patent/ZA858942B/xx unknown
- 1985-11-21 PH PH33077A patent/PH22016A/en unknown
- 1985-11-21 DE DE8585308491T patent/DE3574252D1/de not_active Expired
- 1985-11-21 AT AT85308491T patent/ATE47997T1/de not_active IP Right Cessation
- 1985-11-22 JP JP60263586A patent/JPH064597B2/ja not_active Expired - Lifetime
- 1985-11-22 HU HU854471A patent/HU195189B/hu unknown
- 1985-11-22 NO NO854671A patent/NO166585C/no unknown
- 1985-11-22 SU SU853979907A patent/SU1424736A3/ru active
- 1985-11-22 PT PT81542A patent/PT81542B/pt unknown
- 1985-11-22 DK DK540485A patent/DK164903C/da not_active IP Right Cessation
- 1985-11-22 ES ES549178A patent/ES8704462A1/es not_active Expired
-
1986
- 1986-12-29 ES ES557268A patent/ES8801248A1/es not_active Expired
-
1989
- 1989-04-21 AU AU33329/89A patent/AU3332989A/en not_active Abandoned
-
1991
- 1991-12-17 SG SG1068/91A patent/SG106891G/en unknown
-
1992
- 1992-01-09 HK HK35/92A patent/HK3592A/xx not_active IP Right Cessation
- 1992-05-04 DK DK058292A patent/DK58292A/da not_active Application Discontinuation
-
1994
- 1994-01-18 BG BG098378A patent/BG60762B2/bg unknown
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