IL95440A - N-(2-substituted phenyl)-n'-azabicycloalkyl ureas, their preparation and pharmaceutical compositions containing them - Google Patents
N-(2-substituted phenyl)-n'-azabicycloalkyl ureas, their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL95440A IL95440A IL9544090A IL9544090A IL95440A IL 95440 A IL95440 A IL 95440A IL 9544090 A IL9544090 A IL 9544090A IL 9544090 A IL9544090 A IL 9544090A IL 95440 A IL95440 A IL 95440A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- endo
- azabicyclo
- added
- urea
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000003672 ureas Chemical class 0.000 title abstract description 5
- 235000013877 carbamide Nutrition 0.000 title description 36
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical class FC(F)(F)* 0.000 claims abstract description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 71
- 239000004202 carbamide Substances 0.000 claims description 39
- -1 urea compound Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 abstract description 3
- 206010047700 Vomiting Diseases 0.000 abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 102
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 78
- 239000000203 mixture Substances 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000000047 product Substances 0.000 description 53
- 229940073584 methylene chloride Drugs 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- 229940086542 triethylamine Drugs 0.000 description 34
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 26
- 239000003921 oil Substances 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 229960001866 silicon dioxide Drugs 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 8
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- 229960004373 acetylcholine Drugs 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- YRJCXPFMFZIXRI-UHFFFAOYSA-N nonan-3-amine Chemical compound CCCCCCC(N)CC YRJCXPFMFZIXRI-UHFFFAOYSA-N 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KDAUQEANDYWNNO-UHFFFAOYSA-N NC1=C(C=CC=C1)C=NOC(C)C Chemical compound NC1=C(C=CC=C1)C=NOC(C)C KDAUQEANDYWNNO-UHFFFAOYSA-N 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
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- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 210000003405 ileum Anatomy 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 description 2
- LJXJUCWPADUBSQ-UHFFFAOYSA-N 2-(3-butyl-1,2,4-oxadiazol-5-yl)aniline Chemical compound CCCCC1=NOC(C=2C(=CC=CC=2)N)=N1 LJXJUCWPADUBSQ-UHFFFAOYSA-N 0.000 description 2
- BEKMTRPOJAKFPZ-UHFFFAOYSA-N 2-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline Chemical compound NC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NO1 BEKMTRPOJAKFPZ-UHFFFAOYSA-N 0.000 description 2
- WDAHLGJFOJQXAA-UHFFFAOYSA-N 2-(ethoxyiminomethyl)aniline Chemical compound CCON=CC1=CC=CC=C1N WDAHLGJFOJQXAA-UHFFFAOYSA-N 0.000 description 2
- PCCFZEKGUORCII-UHFFFAOYSA-N 2-(methoxyiminomethyl)aniline Chemical compound CON=CC1=CC=CC=C1N PCCFZEKGUORCII-UHFFFAOYSA-N 0.000 description 2
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- MAQWLSRVNSPIGX-UHFFFAOYSA-N n-methoxy-1-(2-nitrophenyl)methanimine Chemical compound CON=CC1=CC=CC=C1[N+]([O-])=O MAQWLSRVNSPIGX-UHFFFAOYSA-N 0.000 description 2
- JASMWYNKLTULAN-UHFFFAOYSA-N octan-3-amine Chemical compound CCCCCC(N)CC JASMWYNKLTULAN-UHFFFAOYSA-N 0.000 description 2
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- REUAXQZIRFXQML-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1CC2C(N)CN1CC2 REUAXQZIRFXQML-UHFFFAOYSA-N 0.000 description 1
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- HTZWHTQVHWHSHN-UHFFFAOYSA-N 9-methyl-9-azabicyclo[3.3.1]nonan-3-amine Chemical compound C1CCC2CC(N)CC1N2C HTZWHTQVHWHSHN-UHFFFAOYSA-N 0.000 description 1
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- 230000000284 resting effect Effects 0.000 description 1
- 229940021384 salt irrigating solution Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Treating Waste Gases (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Lubricants (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK443489A DK443489D0 (da) | 1989-09-08 | 1989-09-08 | Substituerede urinstofforbindelser, deres fremstilling og anvendelse |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL95440A0 IL95440A0 (en) | 1991-06-30 |
| IL95440A true IL95440A (en) | 1994-07-31 |
Family
ID=8133482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9544090A IL95440A (en) | 1989-09-08 | 1990-08-21 | N-(2-substituted phenyl)-n'-azabicycloalkyl ureas, their preparation and pharmaceutical compositions containing them |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5330990A (es) |
| EP (2) | EP0491770A1 (es) |
| JP (1) | JPH05505171A (es) |
| AT (1) | ATE106885T1 (es) |
| AU (1) | AU639487B2 (es) |
| CA (1) | CA2066696A1 (es) |
| DE (1) | DE69009646T2 (es) |
| DK (2) | DK443489D0 (es) |
| ES (1) | ES2054309T3 (es) |
| FI (1) | FI921005A0 (es) |
| HU (1) | HU208433B (es) |
| IE (1) | IE69266B1 (es) |
| IL (1) | IL95440A (es) |
| NO (1) | NO300460B1 (es) |
| NZ (1) | NZ235117A (es) |
| PT (1) | PT95248B (es) |
| WO (1) | WO1991003475A1 (es) |
| ZA (1) | ZA907111B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8922622D0 (en) * | 1989-10-07 | 1989-11-22 | Wyeth John & Brother Ltd | Aroylureas |
| DK40890D0 (da) * | 1990-02-16 | 1990-02-16 | Ferrosan As | Substituerede urinstofforbindelser, deres fremstilling og anvendelse |
| GB9106571D0 (en) * | 1991-03-27 | 1991-05-15 | Erba Carlo Spa | Derivatives of substituted imidazol-2-one and process for their preparation |
| FR2677019B1 (fr) * | 1991-05-27 | 1994-11-25 | Pf Medicament | Nouvelles piperidines disubstituees-1,4, leur preparation et leur application en therapeutique. |
| GB9120628D0 (en) * | 1991-09-27 | 1991-11-06 | Fujisawa Pharmaceutical Co | Pyrrolobenzoxazine derivatives and process for preparation thereof |
| GB9121835D0 (en) * | 1991-10-15 | 1991-11-27 | Smithkline Beecham Plc | Pharmaceuticals |
| GB9206989D0 (en) * | 1992-03-31 | 1992-05-13 | Glaxo Group Ltd | Chemical compounds |
| EP0640081B1 (en) * | 1992-03-31 | 2000-01-12 | Glaxo Group Limited | Substituted phenylcarbamates and phenylureas, their preparation and their use as 5-ht4 antagonists |
| GB9214184D0 (en) * | 1992-07-03 | 1992-08-12 | Smithkline Beecham Plc | Pharmaceuticals |
| GB9307400D0 (en) * | 1993-04-08 | 1993-06-02 | Smithkline Beecham Plc | Compounds |
| US5773459A (en) * | 1995-06-07 | 1998-06-30 | Sugen, Inc. | Urea- and thiourea-type compounds |
| CA2249410C (en) * | 1996-03-20 | 2007-06-12 | Wake Forest University | Sigma-2 receptors as biomarkers of tumor cell proliferation |
| US6676925B1 (en) | 1996-03-20 | 2004-01-13 | Wake Forest University | Sigma-2 receptors as biomarkers of tumor cell proliferation |
| DE19643037A1 (de) * | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| US6660529B2 (en) * | 1998-07-28 | 2003-12-09 | Pe Corporation | Heteroaryl substituted benzothiazole dioxetanes |
| US6693202B1 (en) | 1999-02-16 | 2004-02-17 | Theravance, Inc. | Muscarinic receptor antagonists |
| UA73543C2 (uk) | 1999-12-07 | 2005-08-15 | Тераванс, Інк. | Похідні сечовини, фармацевтична композиція та застосування похідного при приготуванні лікарського засобу для лікування захворювання, яке опосередковується мускариновим рецептором |
| CA2392028C (en) | 1999-12-07 | 2009-08-18 | Theravance, Inc. | Carbamate derivatives having muscarinic receptor antagonist activity |
| WO2001080905A2 (en) | 2000-04-27 | 2001-11-01 | Wake Forest University Health Sciences | Sigma-2 receptors as biomarkers of tumor cell proliferation |
| US20050069976A1 (en) * | 2001-02-14 | 2005-03-31 | Peter Lind | Protein-coupled receptor |
| PE20040950A1 (es) | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
| US7345060B2 (en) | 2003-11-21 | 2008-03-18 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| GB0602778D0 (en) | 2006-02-10 | 2006-03-22 | Glaxo Group Ltd | Novel compound |
| KR20230043024A (ko) | 2020-07-24 | 2023-03-30 | 젠자임 코포레이션 | 벤글루스타트를 포함하는 제약 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158265A2 (en) | 1984-04-13 | 1985-10-16 | Beecham Group Plc | Benzamide and anilide derivatives |
| EP0235878A3 (en) * | 1986-01-16 | 1989-06-14 | Beecham Group Plc | Novel compounds |
| AU611976B2 (en) * | 1987-12-24 | 1991-06-27 | John Wyeth & Brother Limited | Aroyl urea and carbamic acid derivatives of azabicyclo compounds |
| DK40890D0 (da) * | 1990-02-16 | 1990-02-16 | Ferrosan As | Substituerede urinstofforbindelser, deres fremstilling og anvendelse |
-
1989
- 1989-09-08 DK DK443489A patent/DK443489D0/da not_active Application Discontinuation
-
1990
- 1990-08-21 IL IL9544090A patent/IL95440A/en not_active IP Right Cessation
- 1990-08-24 IE IE308290A patent/IE69266B1/en not_active IP Right Cessation
- 1990-08-31 NZ NZ235117A patent/NZ235117A/en unknown
- 1990-09-06 JP JP2512602A patent/JPH05505171A/ja active Pending
- 1990-09-06 WO PCT/DK1990/000232 patent/WO1991003475A1/en not_active Application Discontinuation
- 1990-09-06 CA CA002066696A patent/CA2066696A1/en not_active Abandoned
- 1990-09-06 DE DE69009646T patent/DE69009646T2/de not_active Expired - Fee Related
- 1990-09-06 ZA ZA907111A patent/ZA907111B/xx unknown
- 1990-09-06 EP EP90913477A patent/EP0491770A1/en active Pending
- 1990-09-06 HU HU92776A patent/HU208433B/hu not_active IP Right Cessation
- 1990-09-06 EP EP90610056A patent/EP0419397B1/en not_active Expired - Lifetime
- 1990-09-06 AT AT90610056T patent/ATE106885T1/de not_active IP Right Cessation
- 1990-09-06 ES ES90610056T patent/ES2054309T3/es not_active Expired - Lifetime
- 1990-09-06 DK DK90610056.5T patent/DK0419397T3/da active
- 1990-09-06 AU AU63414/90A patent/AU639487B2/en not_active Ceased
- 1990-09-07 PT PT95248A patent/PT95248B/pt not_active IP Right Cessation
-
1992
- 1992-03-03 NO NO920833A patent/NO300460B1/no unknown
- 1992-03-06 FI FI921005A patent/FI921005A0/fi not_active Application Discontinuation
- 1992-09-17 US US07/947,073 patent/US5330990A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0491770A1 (en) | 1992-07-01 |
| IE903082A1 (en) | 1991-03-13 |
| CA2066696A1 (en) | 1991-03-09 |
| NO920833L (no) | 1992-03-03 |
| HUT61019A (en) | 1992-11-30 |
| PT95248B (pt) | 1997-06-30 |
| AU6341490A (en) | 1991-04-08 |
| ATE106885T1 (de) | 1994-06-15 |
| EP0419397B1 (en) | 1994-06-08 |
| JPH05505171A (ja) | 1993-08-05 |
| IE69266B1 (en) | 1996-08-21 |
| DE69009646D1 (de) | 1994-07-14 |
| AU639487B2 (en) | 1993-07-29 |
| PT95248A (pt) | 1991-05-22 |
| DE69009646T2 (de) | 1995-01-12 |
| NO920833D0 (no) | 1992-03-03 |
| ES2054309T3 (es) | 1994-08-01 |
| DK0419397T3 (da) | 1994-10-10 |
| US5330990A (en) | 1994-07-19 |
| IL95440A0 (en) | 1991-06-30 |
| FI921005A0 (fi) | 1992-03-06 |
| NZ235117A (en) | 1993-02-25 |
| HU9200776D0 (en) | 1992-08-28 |
| DK443489D0 (da) | 1989-09-08 |
| WO1991003475A1 (en) | 1991-03-21 |
| EP0419397A1 (en) | 1991-03-27 |
| NO300460B1 (no) | 1997-06-02 |
| HU208433B (en) | 1993-10-28 |
| ZA907111B (en) | 1991-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| RH | Patent void |