NO318206B1 - Nye cyklobutaindolkarboksamidforbindelser og farmasoytiske sammensetninger inneholdende dem - Google Patents
Nye cyklobutaindolkarboksamidforbindelser og farmasoytiske sammensetninger inneholdende dem Download PDFInfo
- Publication number
- NO318206B1 NO318206B1 NO20011863A NO20011863A NO318206B1 NO 318206 B1 NO318206 B1 NO 318206B1 NO 20011863 A NO20011863 A NO 20011863A NO 20011863 A NO20011863 A NO 20011863A NO 318206 B1 NO318206 B1 NO 318206B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- cyclobuta
- tetrahydro
- group
- indole
- Prior art date
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- -1 carboxamide compounds Chemical class 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 106
- CQILOHWHIWNQOE-UHFFFAOYSA-N indole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)C=CC2=C1 CQILOHWHIWNQOE-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000019022 Mood disease Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- PZBKLLRNMBWPCX-UHFFFAOYSA-N 5-cyano-5-phenylsulfanyl-N-pyridin-3-yl-9-azatricyclo[6.3.0.03,6]undeca-1,3(6),7-triene-9-carboxamide Chemical compound C1CC2=CC=3CC(SC=4C=CC=CC=4)(C#N)C=3C=C2N1C(=O)NC1=CC=CN=C1 PZBKLLRNMBWPCX-UHFFFAOYSA-N 0.000 claims description 3
- 206010013654 Drug abuse Diseases 0.000 claims description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
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- CDBZKPZBKKMJJD-UHFFFAOYSA-N C1CC=2C=C3C(CO)CC3=CC=2N1C(=O)NC1=CC=CN=C1 Chemical compound C1CC=2C=C3C(CO)CC3=CC=2N1C(=O)NC1=CC=CN=C1 CDBZKPZBKKMJJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 2
- 239000000047 product Substances 0.000 description 81
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- 238000002360 preparation method Methods 0.000 description 41
- 239000000243 solution Substances 0.000 description 36
- 238000002844 melting Methods 0.000 description 25
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 24
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- 239000011541 reaction mixture Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 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 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- YPYYEXCFVCKWPH-UHFFFAOYSA-N 6-cyano-6-cyclohexyl-n-(3-pyridyl)-2,3,5,6-tetrahydro-1h-cyclobuta[f]indole-1-carboxamide Chemical compound C1CC2=CC=3CC(C#N)(C4CCCCC4)C=3C=C2N1C(=O)NC1=CC=CN=C1 YPYYEXCFVCKWPH-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
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- 239000003826 tablet Substances 0.000 description 3
- 150000003512 tertiary amines Chemical group 0.000 description 3
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
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- LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 description 2
- ZTSSGZYHPYRJNV-UHFFFAOYSA-N 2,3,6,7-tetrahydro-1h-cyclobuta[g]indol-7-ylmethanol Chemical compound C1=C2CCNC2=C2C(CO)CC2=C1 ZTSSGZYHPYRJNV-UHFFFAOYSA-N 0.000 description 2
- XDZUHXBIGDNLOQ-UHFFFAOYSA-N 6-cyclohexyl-n-(3-pyridyl)-2,3,5,6-tetrahydro-1h-cyclobuta[f]indole-1-carboxamide Chemical compound C1CC2=CC=3CC(C4CCCCC4)C=3C=C2N1C(=O)NC1=CC=CN=C1 XDZUHXBIGDNLOQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 208000015114 central nervous system disease Diseases 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
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- 238000005303 weighing Methods 0.000 description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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- STHWAAKLFCZCNL-UHFFFAOYSA-N 5-phenylsulfanyl-9-azatricyclo[6.3.0.03,6]undeca-1,3(6),7-triene-5-carbonitrile Chemical compound C1C2=CC=3CCNC=3C=C2C1(C#N)SC1=CC=CC=C1 STHWAAKLFCZCNL-UHFFFAOYSA-N 0.000 description 1
- GYCUKFDCCFYATP-UHFFFAOYSA-N 6,7-dihydro-3h-cyclobuta[e]indole-7-carbonitrile Chemical compound C1=C2NC=CC2=C2C(C#N)CC2=C1 GYCUKFDCCFYATP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- 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
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- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- 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
Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Addiction (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0004743A FR2807754A1 (fr) | 2000-04-13 | 2000-04-13 | Nouveaux derives de cyclobuta-indole carboxamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20011863D0 NO20011863D0 (no) | 2001-04-11 |
| NO20011863L NO20011863L (no) | 2001-10-15 |
| NO318206B1 true NO318206B1 (no) | 2005-02-14 |
Family
ID=8849213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20011863A NO318206B1 (no) | 2000-04-13 | 2001-04-11 | Nye cyklobutaindolkarboksamidforbindelser og farmasoytiske sammensetninger inneholdende dem |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US6452015B2 (xx) |
| EP (1) | EP1146044B1 (xx) |
| JP (1) | JP3396675B2 (xx) |
| KR (1) | KR100470691B1 (xx) |
| CN (1) | CN1323796A (xx) |
| AR (1) | AR042379A1 (xx) |
| AT (1) | ATE275140T1 (xx) |
| AU (1) | AU779366B2 (xx) |
| BR (1) | BR0101466A (xx) |
| CA (1) | CA2344108C (xx) |
| DE (1) | DE60105219T2 (xx) |
| DK (1) | DK1146044T3 (xx) |
| EA (1) | EA004738B1 (xx) |
| ES (1) | ES2227082T3 (xx) |
| FR (1) | FR2807754A1 (xx) |
| HK (1) | HK1040247A1 (xx) |
| HU (1) | HUP0101504A3 (xx) |
| NO (1) | NO318206B1 (xx) |
| NZ (1) | NZ511091A (xx) |
| PL (1) | PL347046A1 (xx) |
| PT (1) | PT1146044E (xx) |
| SI (1) | SI1146044T1 (xx) |
| TR (1) | TR200402685T4 (xx) |
| ZA (1) | ZA200103064B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2837823B1 (fr) * | 2002-03-27 | 2005-04-08 | Servier Lab | Nouveaux derives d'indoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2933975B1 (fr) * | 2008-07-17 | 2011-02-18 | Servier Lab | Nouveau procede de preparation de benzocyclobutenes fonctionnalises,et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| KR20220029900A (ko) * | 2020-09-02 | 2022-03-10 | 에스케이하이닉스 주식회사 | 버퍼 회로 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0656003A1 (en) * | 1992-08-20 | 1995-06-07 | Smithkline Beecham Plc | Condensed indole derivatives as 5ht2c and 5ht2b antagonists |
| GB9306460D0 (en) * | 1993-03-29 | 1993-05-19 | Smithkline Beecham Plc | Novel compounds |
| EP0757687A1 (en) * | 1994-04-23 | 1997-02-12 | Smithkline Beecham Plc | Tricyclic derivatives as 5ht 2c? and 5ht 2b? antagonists |
| SI0808312T1 (xx) * | 1995-02-02 | 2001-02-28 | Smithkline Beecham Plc | |
| CA2195346C (en) * | 1995-12-21 | 2007-04-10 | Zhi Yuan Wang | Benzocyclobutenones and polymers derived therefrom |
| EP1066036B1 (en) * | 1998-02-27 | 2006-04-26 | The Board Of Trustees Of The University Of Illinois | Agents with serotonin-related activity for the treatment for sleep apnea |
-
2000
- 2000-04-13 FR FR0004743A patent/FR2807754A1/fr active Pending
-
2001
- 2001-04-11 AR ARP010101714A patent/AR042379A1/es not_active Application Discontinuation
- 2001-04-11 BR BR0101466-8A patent/BR0101466A/pt not_active Application Discontinuation
- 2001-04-11 NO NO20011863A patent/NO318206B1/no unknown
- 2001-04-12 SI SI200130181T patent/SI1146044T1/xx unknown
- 2001-04-12 AT AT01400939T patent/ATE275140T1/de not_active IP Right Cessation
- 2001-04-12 TR TR2004/02685T patent/TR200402685T4/xx unknown
- 2001-04-12 AU AU35186/01A patent/AU779366B2/en not_active Ceased
- 2001-04-12 ZA ZA200103064A patent/ZA200103064B/xx unknown
- 2001-04-12 DE DE60105219T patent/DE60105219T2/de not_active Expired - Fee Related
- 2001-04-12 US US09/833,826 patent/US6452015B2/en not_active Expired - Fee Related
- 2001-04-12 EA EA200100344A patent/EA004738B1/ru not_active IP Right Cessation
- 2001-04-12 JP JP2001114261A patent/JP3396675B2/ja not_active Expired - Fee Related
- 2001-04-12 PT PT01400939T patent/PT1146044E/pt unknown
- 2001-04-12 DK DK01400939T patent/DK1146044T3/da active
- 2001-04-12 NZ NZ511091A patent/NZ511091A/en unknown
- 2001-04-12 PL PL01347046A patent/PL347046A1/xx not_active Application Discontinuation
- 2001-04-12 ES ES01400939T patent/ES2227082T3/es not_active Expired - Lifetime
- 2001-04-12 HU HU0101504A patent/HUP0101504A3/hu unknown
- 2001-04-12 EP EP01400939A patent/EP1146044B1/fr not_active Expired - Lifetime
- 2001-04-12 CA CA002344108A patent/CA2344108C/fr not_active Expired - Fee Related
- 2001-04-13 KR KR10-2001-0019839A patent/KR100470691B1/ko not_active IP Right Cessation
- 2001-04-13 CN CN01116387A patent/CN1323796A/zh active Pending
-
2002
- 2002-03-14 HK HK02101964.8A patent/HK1040247A1/zh unknown
- 2002-07-12 US US10/195,009 patent/US6743818B2/en not_active Expired - Fee Related
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