NO316756B1 - Indolinderivater, deres fremstilling og anvendelse, og farmasoytiske preparater inneholdende dem - Google Patents
Indolinderivater, deres fremstilling og anvendelse, og farmasoytiske preparater inneholdende dem Download PDFInfo
- Publication number
- NO316756B1 NO316756B1 NO19985970A NO985970A NO316756B1 NO 316756 B1 NO316756 B1 NO 316756B1 NO 19985970 A NO19985970 A NO 19985970A NO 985970 A NO985970 A NO 985970A NO 316756 B1 NO316756 B1 NO 316756B1
- Authority
- NO
- Norway
- Prior art keywords
- pyridin
- hydrogen
- ylmethyloxy
- compound
- formula
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 14
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- DMTYWFWKUOCEKE-UHFFFAOYSA-N n-[6-(pyridin-2-ylmethoxy)pyridin-3-yl]-5-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(C(F)(F)F)=CC=C2N1C(=O)NC(C=N1)=CC=C1OCC1=CC=CC=N1 DMTYWFWKUOCEKE-UHFFFAOYSA-N 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- QFPXEFZKXYSMPH-UHFFFAOYSA-N 5-methyl-n-[5-methyl-6-(pyridin-2-ylmethoxy)pyridin-3-yl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound CC1=CC(NC(=O)N2C3=CC(=C(C)C=C3CC2)C(F)(F)F)=CN=C1OCC1=CC=CC=N1 QFPXEFZKXYSMPH-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- QYQQPOAMTVZFQL-UHFFFAOYSA-N n-[6-(pyridin-2-ylmethoxy)pyridin-3-yl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C12=CC(C(F)(F)F)=CC=C2CCN1C(=O)NC(C=N1)=CC=C1OCC1=CC=CC=N1 QYQQPOAMTVZFQL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- -1 phenoxy, phenylthio Chemical group 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- QHJGYLHCSJDUOF-UHFFFAOYSA-N 3-methyl-5-nitro-2-(pyridin-2-ylmethoxy)pyridine Chemical compound CC1=CC([N+]([O-])=O)=CN=C1OCC1=CC=CC=N1 QHJGYLHCSJDUOF-UHFFFAOYSA-N 0.000 description 3
- LCFDJWUYKUPBJM-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-indole Chemical compound FC(F)(F)C1=CC=C2NC=CC2=C1 LCFDJWUYKUPBJM-UHFFFAOYSA-N 0.000 description 3
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 description 1
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 1
- QEDCHCLHHGGYBT-UHFFFAOYSA-N 5-bromo-2,3-dihydro-1h-indole Chemical compound BrC1=CC=C2NCCC2=C1 QEDCHCLHHGGYBT-UHFFFAOYSA-N 0.000 description 1
- IFTLUSMGMNIWMV-UHFFFAOYSA-N 5-nitro-2-(pyridin-2-ylmethoxy)pyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1OCC1=CC=CC=N1 IFTLUSMGMNIWMV-UHFFFAOYSA-N 0.000 description 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 1
- WWBVZCBWSHFMLP-UHFFFAOYSA-N 6-(trifluoromethyl)-2,3-dihydro-1h-indole Chemical compound FC(F)(F)C1=CC=C2CCNC2=C1 WWBVZCBWSHFMLP-UHFFFAOYSA-N 0.000 description 1
- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 101000761348 Homo sapiens 5-hydroxytryptamine receptor 2C Proteins 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 101000761350 Rattus norvegicus 5-hydroxytryptamine receptor 2C Proteins 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000027288 circadian rhythm Effects 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000002476 indolines Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
- C07D401/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9612885.5A GB9612885D0 (en) | 1996-06-20 | 1996-06-20 | Novel compounds |
PCT/EP1997/003157 WO1997048700A1 (en) | 1996-06-20 | 1997-06-16 | Indoline derivatives useful as 5-ht-2c receptor antagonists |
Publications (3)
Publication Number | Publication Date |
---|---|
NO985970L NO985970L (no) | 1998-12-18 |
NO985970D0 NO985970D0 (no) | 1998-12-18 |
NO316756B1 true NO316756B1 (no) | 2004-04-26 |
Family
ID=10795577
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19985970A NO316756B1 (no) | 1996-06-20 | 1998-12-18 | Indolinderivater, deres fremstilling og anvendelse, og farmasoytiske preparater inneholdende dem |
Country Status (28)
Country | Link |
---|---|
US (2) | US6313145B1 (zh) |
EP (1) | EP0912556B1 (zh) |
JP (1) | JP2000512644A (zh) |
KR (1) | KR20040101563A (zh) |
CN (1) | CN1147485C (zh) |
AR (1) | AR008244A1 (zh) |
AT (1) | ATE196766T1 (zh) |
AU (1) | AU718000B2 (zh) |
BR (1) | BR9709982A (zh) |
CA (1) | CA2258559A1 (zh) |
CO (1) | CO4870758A1 (zh) |
CZ (1) | CZ289799B6 (zh) |
DE (1) | DE69703242T2 (zh) |
DK (1) | DK0912556T3 (zh) |
ES (1) | ES2152682T3 (zh) |
GB (1) | GB9612885D0 (zh) |
GR (1) | GR3034847T3 (zh) |
HK (1) | HK1019744A1 (zh) |
HU (1) | HUP9903480A3 (zh) |
IL (1) | IL127304A (zh) |
NO (1) | NO316756B1 (zh) |
NZ (1) | NZ332840A (zh) |
PL (1) | PL186885B1 (zh) |
PT (1) | PT912556E (zh) |
TR (1) | TR199802552T2 (zh) |
TW (1) | TW360650B (zh) |
WO (1) | WO1997048700A1 (zh) |
ZA (1) | ZA975416B (zh) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9710523D0 (en) * | 1997-05-23 | 1997-07-16 | Smithkline Beecham Plc | Novel compounds |
WO1999043650A2 (en) * | 1998-02-25 | 1999-09-02 | Smithkline Beecham Plc | Process(es) for the preparation of 6-trifluoromethyl-indoline derivatives |
GB0019950D0 (en) * | 2000-08-12 | 2000-09-27 | Smithkline Beecham Plc | Compounds |
US20030008880A1 (en) * | 2001-05-02 | 2003-01-09 | Pfizer Inc. | 4-(2-Pyridyl) piperizines having 5HT7 receptor agonist activity |
JP2005535560A (ja) | 2001-11-28 | 2005-11-24 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 治療用の化合物 |
GB0200283D0 (en) * | 2002-01-08 | 2002-02-20 | Smithkline Beecham Plc | Compounds |
MXPA04008517A (es) | 2002-03-04 | 2005-08-19 | Pharmacia & Upjohn Co Llc | Compuestos terapeuticos. |
JP2005529117A (ja) * | 2002-04-19 | 2005-09-29 | グラクソ グループ リミテッド | 5HT2c受容体に対する親和性を有する化合物及びその治療における使用 |
GB0305024D0 (en) * | 2003-03-05 | 2003-04-09 | Glaxo Group Ltd | Compounds |
GB0305553D0 (en) * | 2003-03-11 | 2003-04-16 | Glaxo Group Ltd | Compounds |
KR101062376B1 (ko) * | 2008-04-10 | 2011-09-06 | 한국화학연구원 | 신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물 |
CN102348798A (zh) | 2009-01-16 | 2012-02-08 | 麻省理工学院 | 孤独症谱系障碍的诊断和治疗 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU4704693A (en) * | 1992-08-20 | 1994-03-15 | Smithkline Beecham Plc | Condensed indole derivatives as 5HT-2C and 5HT-2B antagonists |
GB9313913D0 (en) * | 1993-07-06 | 1993-08-18 | Smithkline Beecham Plc | Novel compounds |
EP0807104A2 (en) | 1995-02-02 | 1997-11-19 | Smithkline Beecham Plc | Heterocyclic compounds possessing 5ht 2c? receptor antagonist activity |
EA000304B1 (ru) | 1995-02-02 | 1999-04-29 | Смитклайн Бичам Плс | Производные индола как антагонисты рецептора 5-ht |
GB9607219D0 (en) | 1996-04-04 | 1996-06-12 | Smithkline Beecham Plc | Novel compounds |
US6028055A (en) | 1996-10-22 | 2000-02-22 | Genetech, Inc. | Receptor selective BNP |
-
1996
- 1996-06-20 GB GBGB9612885.5A patent/GB9612885D0/en active Pending
-
1997
- 1997-06-16 IL IL12730497A patent/IL127304A/xx not_active IP Right Cessation
- 1997-06-16 CN CNB971955395A patent/CN1147485C/zh not_active Expired - Fee Related
- 1997-06-16 AU AU33396/97A patent/AU718000B2/en not_active Ceased
- 1997-06-16 JP JP10502260A patent/JP2000512644A/ja not_active Ceased
- 1997-06-16 US US09/202,772 patent/US6313145B1/en not_active Expired - Fee Related
- 1997-06-16 DK DK97929202T patent/DK0912556T3/da active
- 1997-06-16 PL PL97330708A patent/PL186885B1/pl not_active IP Right Cessation
- 1997-06-16 DE DE69703242T patent/DE69703242T2/de not_active Expired - Fee Related
- 1997-06-16 CA CA002258559A patent/CA2258559A1/en not_active Abandoned
- 1997-06-16 AT AT97929202T patent/ATE196766T1/de not_active IP Right Cessation
- 1997-06-16 ES ES97929202T patent/ES2152682T3/es not_active Expired - Lifetime
- 1997-06-16 TR TR1998/02552T patent/TR199802552T2/xx unknown
- 1997-06-16 HU HU9903480A patent/HUP9903480A3/hu not_active Application Discontinuation
- 1997-06-16 CZ CZ19984204A patent/CZ289799B6/cs not_active IP Right Cessation
- 1997-06-16 WO PCT/EP1997/003157 patent/WO1997048700A1/en active IP Right Grant
- 1997-06-16 PT PT97929202T patent/PT912556E/pt unknown
- 1997-06-16 EP EP97929202A patent/EP0912556B1/en not_active Expired - Lifetime
- 1997-06-16 BR BR9709982A patent/BR9709982A/pt not_active Application Discontinuation
- 1997-06-16 NZ NZ332840A patent/NZ332840A/xx unknown
- 1997-06-16 KR KR10-2004-7017304A patent/KR20040101563A/ko active IP Right Grant
- 1997-06-18 AR ARP970102675A patent/AR008244A1/es active IP Right Grant
- 1997-06-19 ZA ZA975416A patent/ZA975416B/xx unknown
- 1997-06-19 TW TW086108550A patent/TW360650B/zh active
- 1997-06-20 CO CO97034433A patent/CO4870758A1/es unknown
-
1998
- 1998-12-18 NO NO19985970A patent/NO316756B1/no unknown
-
1999
- 1999-11-02 HK HK99104963A patent/HK1019744A1/xx not_active IP Right Cessation
-
2000
- 2000-11-14 GR GR20000402536T patent/GR3034847T3/el not_active IP Right Cessation
-
2001
- 2001-09-06 US US09/948,289 patent/US20020035134A1/en not_active Abandoned
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