DE69133295T2 - 3,9-diazabicyclo-[3.3.1]-nonanylderivate, verfahren und intermediate für ihre darstellung und sie enthaltende pharmazeutische zusammensetzungen - Google Patents
3,9-diazabicyclo-[3.3.1]-nonanylderivate, verfahren und intermediate für ihre darstellung und sie enthaltende pharmazeutische zusammensetzungen Download PDFInfo
- Publication number
- DE69133295T2 DE69133295T2 DE69133295T DE69133295T DE69133295T2 DE 69133295 T2 DE69133295 T2 DE 69133295T2 DE 69133295 T DE69133295 T DE 69133295T DE 69133295 T DE69133295 T DE 69133295T DE 69133295 T2 DE69133295 T2 DE 69133295T2
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- Germany
- Prior art keywords
- methyl
- compound
- formula
- alkyl
- hydrogen
- Prior art date
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- Expired - Lifetime
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- -1 3,9-DIAZABICYCLO- [3.3.1] -NONANYL Chemical class 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 239000000543 intermediate Substances 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 206010047700 Vomiting Diseases 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 230000008673 vomiting Effects 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 208000015114 central nervous system disease Diseases 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- PRYMYEIFEZDNQM-UHFFFAOYSA-N 3-benzyl-9-methyl-3,9-diazabicyclo[3.3.1]nonan-7-one Chemical compound C1C(CC(=O)C2)N(C)C2CN1CC1=CC=CC=C1 PRYMYEIFEZDNQM-UHFFFAOYSA-N 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 3
- 208000009935 visceral pain Diseases 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 2
- RWTIGSVLCKEUPK-UHFFFAOYSA-N 3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonan-7-one Chemical compound C1C(=O)CC2CN(C)CC1N2C RWTIGSVLCKEUPK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 2
- 231100000869 headache Toxicity 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 abstract description 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- 229940113081 5 Hydroxytryptamine 3 receptor antagonist Drugs 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 208000018522 Gastrointestinal disease Diseases 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XAZVKFDMKFBCTG-UHFFFAOYSA-N 3-benzyl-9-methyl-3,9-diazabicyclo[3.3.1]nonane-7-carboxamide Chemical compound C(C1=CC=CC=C1)N1CC2CC(CC(C1)N2C)C(=O)N XAZVKFDMKFBCTG-UHFFFAOYSA-N 0.000 description 5
- 208000002193 Pain Diseases 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002464 receptor antagonist Substances 0.000 description 5
- 229940044551 receptor antagonist Drugs 0.000 description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- 0 *O*C(CC1)C2*C1C*C2 Chemical compound *O*C(CC1)C2*C1C*C2 0.000 description 2
- NPNWVMBPSINFBV-UHFFFAOYSA-N 1-methylindazole-3-carbonyl chloride Chemical compound C1=CC=C2N(C)N=C(C(Cl)=O)C2=C1 NPNWVMBPSINFBV-UHFFFAOYSA-N 0.000 description 2
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 2
- XMETVEKLDQDETR-UHFFFAOYSA-N 3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonane-7-carboxamide Chemical compound CN1CC2CC(CC(C1)N2C)C(=O)N XMETVEKLDQDETR-UHFFFAOYSA-N 0.000 description 2
- FGNBIFPAQZRPSH-UHFFFAOYSA-N 3-(cyclohexylmethyl)-9-methyl-3,9-diazabicyclo[3.3.1]nonane-7-carboxamide hydrochloride Chemical compound Cl.C1(CCCCC1)CN1CC2CC(CC(C1)N2C)C(=O)N FGNBIFPAQZRPSH-UHFFFAOYSA-N 0.000 description 2
- ORGOMICPFRWESB-UHFFFAOYSA-N 3-ethyl-9-methyl-3,9-diazabicyclo[3.3.1]nonane-7-carboxamide Chemical compound C(C)N1CC2CC(CC(C1)N2C)C(=O)N ORGOMICPFRWESB-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
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- DEVJSKAXZHHBAB-UHFFFAOYSA-N 9-methyl-3-propan-2-yl-3,9-diazabicyclo[3.3.1]nonane-7-carboxamide Chemical compound C(C)(C)N1CC2CC(CC(C1)N2C)C(=O)N DEVJSKAXZHHBAB-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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- 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
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (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)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909020927A GB9020927D0 (en) | 1990-09-26 | 1990-09-26 | Pharmaceuticals |
| GB9020927 | 1990-09-26 | ||
| PCT/GB1991/001629 WO1992005174A1 (en) | 1990-09-26 | 1991-09-23 | 3,9-diazabicyclo (3.3.1) nonan-7-yl derivatives, process and intermediates for their preparation and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69133295D1 DE69133295D1 (de) | 2003-08-21 |
| DE69133295T2 true DE69133295T2 (de) | 2004-03-18 |
Family
ID=10682769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69133295T Expired - Lifetime DE69133295T2 (de) | 1990-09-26 | 1991-09-23 | 3,9-diazabicyclo-[3.3.1]-nonanylderivate, verfahren und intermediate für ihre darstellung und sie enthaltende pharmazeutische zusammensetzungen |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0550550B1 (https=) |
| JP (1) | JP2831464B2 (https=) |
| KR (1) | KR100200438B1 (https=) |
| AT (1) | ATE245157T1 (https=) |
| AU (1) | AU652187B2 (https=) |
| CA (1) | CA2092431C (https=) |
| CY (1) | CY2387B1 (https=) |
| DE (1) | DE69133295T2 (https=) |
| DK (1) | DK0550550T3 (https=) |
| ES (1) | ES2203609T3 (https=) |
| GB (1) | GB9020927D0 (https=) |
| IE (1) | IE913352A1 (https=) |
| MX (1) | MX9101236A (https=) |
| NZ (1) | NZ239915A (https=) |
| PT (1) | PT99028B (https=) |
| TW (1) | TW240227B (https=) |
| WO (1) | WO1992005174A1 (https=) |
| ZA (1) | ZA917606B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9121170D0 (en) * | 1991-10-05 | 1991-11-20 | Smithkline Beecham Plc | Pharmaceuticals |
| US5344831A (en) * | 1992-01-31 | 1994-09-06 | Nisshin Flour Milling Co., Ltd. | Diazabicyclo derivatives |
| GB9214184D0 (en) * | 1992-07-03 | 1992-08-12 | Smithkline Beecham Plc | Pharmaceuticals |
| US5514690A (en) * | 1992-11-17 | 1996-05-07 | E. R. Squibb & Sons, Inc. | Aminocarbonyl (thiocarbonyl) and cyanoguanidine derivatives of quinoline and indoline |
| US5869478A (en) * | 1995-06-07 | 1999-02-09 | Bristol-Myers Squibb Company | Sulfonamido substituted benzopyran derivatives |
| US5629429A (en) * | 1995-06-07 | 1997-05-13 | Bristol-Myers Squibb Company | Process for preparing 4-arylamino-benzopyran and related compounds |
| US5612370A (en) * | 1995-06-07 | 1997-03-18 | Bristol-Myers Squibb Company | Phenylglycine and phenylalaninen amido benzopyran derivatives |
| US5612323A (en) * | 1995-06-07 | 1997-03-18 | Bristol-Myers Squibb Company | Phosphinic ester substituted benzopyran derivatives |
| GB9721139D0 (en) | 1997-10-07 | 1997-12-03 | Glaxo Group Ltd | Medicaments |
| HRP20041132A2 (en) | 2002-04-29 | 2006-07-31 | Actelion Pharmaceuticals Ltd. | 7-aryl-3, 9-diazabicyclo (3.3.1) non-6-ene derivatives and their use as renin inhibitors in the treatment of hypertension, cardiovascular or renal diseases |
| EP1678176A1 (en) * | 2003-10-13 | 2006-07-12 | Actelion Pharmaceuticals Ltd. | Diazabicyclononene derivatives and their use as renin inhibitors |
| US7737163B2 (en) | 2004-06-15 | 2010-06-15 | Pfizer Inc. | Benzimidazolone carboxylic acid derivatives |
| WO2005123718A2 (en) | 2004-06-15 | 2005-12-29 | Pfizer Japan Inc. | Benzimidazolone carboxylic acid derivatives |
| AP2007004067A0 (en) | 2005-02-22 | 2007-08-31 | Pfizer | Oxyindole derivatives as 5HT4 receptor agonists |
| US8129538B1 (en) | 2007-03-28 | 2012-03-06 | Takeda Pharmaceutical Company Limited | Renin inhibitors |
| GB201511382D0 (en) | 2015-06-29 | 2015-08-12 | Imp Innovations Ltd | Novel compounds and their use in therapy |
| JP2025530213A (ja) | 2022-09-09 | 2025-09-11 | ミリックス ファーマ リミテッド | Ｎｍｔ阻害剤を含む抗体薬物コンジュゲート及びその使用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3687080T2 (de) * | 1985-04-27 | 1993-03-25 | Beecham Group Plc | Azabicyclononyl-indazol-carboxamid mit 5-ht-antagonistischer wirkung. |
| HU895334D0 (en) * | 1986-07-30 | 1990-01-28 | Sandoz Ag | Process for the preparation of nasal pharmaceutical compositions |
| US4920227A (en) * | 1988-11-29 | 1990-04-24 | Rorer Pharmaceutical Corp. | Benzobicyclic carboxamide 5-HT3 antagonists |
| US4920219A (en) * | 1988-11-29 | 1990-04-24 | Rorer Pharmaceutical Corp. | Substituted saturated and unsaturated indole quinoline and benzazepine carboxamides and their use as pharmacological agents |
-
1990
- 1990-09-26 GB GB909020927A patent/GB9020927D0/en active Pending
-
1991
- 1991-09-23 ES ES91916973T patent/ES2203609T3/es not_active Expired - Lifetime
- 1991-09-23 DE DE69133295T patent/DE69133295T2/de not_active Expired - Lifetime
- 1991-09-23 EP EP91916973A patent/EP0550550B1/en not_active Expired - Lifetime
- 1991-09-23 DK DK91916973T patent/DK0550550T3/da active
- 1991-09-23 CA CA002092431A patent/CA2092431C/en not_active Expired - Lifetime
- 1991-09-23 AU AU86244/91A patent/AU652187B2/en not_active Expired
- 1991-09-23 WO PCT/GB1991/001629 patent/WO1992005174A1/en not_active Ceased
- 1991-09-23 AT AT91916973T patent/ATE245157T1/de not_active IP Right Cessation
- 1991-09-23 JP JP3515796A patent/JP2831464B2/ja not_active Expired - Lifetime
- 1991-09-24 NZ NZ239915A patent/NZ239915A/xx not_active IP Right Cessation
- 1991-09-24 MX MX9101236A patent/MX9101236A/es unknown
- 1991-09-24 PT PT99028A patent/PT99028B/pt not_active IP Right Cessation
- 1991-09-24 ZA ZA917606A patent/ZA917606B/xx unknown
- 1991-09-24 IE IE335291A patent/IE913352A1/en not_active Application Discontinuation
- 1991-09-26 TW TW080107616A patent/TW240227B/zh active
-
1993
- 1993-03-26 KR KR1019930700921A patent/KR100200438B1/ko not_active Expired - Lifetime
-
2003
- 2003-10-17 CY CY0300069A patent/CY2387B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2203609T3 (es) | 2004-04-16 |
| JP2831464B2 (ja) | 1998-12-02 |
| IE913352A1 (en) | 1992-04-08 |
| CA2092431A1 (en) | 1992-03-27 |
| EP0550550B1 (en) | 2003-07-16 |
| AU652187B2 (en) | 1994-08-18 |
| AU8624491A (en) | 1992-04-15 |
| CY2387B1 (en) | 2004-09-10 |
| HK1012356A1 (en) | 1999-07-30 |
| MX9101236A (es) | 1992-05-04 |
| ATE245157T1 (de) | 2003-08-15 |
| WO1992005174A1 (en) | 1992-04-02 |
| NZ239915A (en) | 1993-11-25 |
| PT99028B (pt) | 1999-02-26 |
| JPH06501256A (ja) | 1994-02-10 |
| GB9020927D0 (en) | 1990-11-07 |
| TW240227B (https=) | 1995-02-11 |
| EP0550550A1 (en) | 1993-07-14 |
| KR100200438B1 (ko) | 1999-06-15 |
| PT99028A (pt) | 1993-10-29 |
| CA2092431C (en) | 2002-12-10 |
| KR930702345A (ko) | 1993-09-08 |
| DE69133295D1 (de) | 2003-08-21 |
| DK0550550T3 (da) | 2003-09-08 |
| ZA917606B (en) | 1992-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |