UA73163C2 - Indilyn-2-one derivatives, method for obtaining thereof and use as ligands of oxytocin receptor - Google Patents
Indilyn-2-one derivatives, method for obtaining thereof and use as ligands of oxytocin receptor Download PDFInfo
- Publication number
- UA73163C2 UA73163C2 UA2002097763A UA2002097763A UA73163C2 UA 73163 C2 UA73163 C2 UA 73163C2 UA 2002097763 A UA2002097763 A UA 2002097763A UA 2002097763 A UA2002097763 A UA 2002097763A UA 73163 C2 UA73163 C2 UA 73163C2
- Authority
- UA
- Ukraine
- Prior art keywords
- chloro
- methyl
- dimethoxybenzyl
- oxoindolin
- alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 64
- 102000004279 Oxytocin receptors Human genes 0.000 title claims description 13
- 108090000876 Oxytocin receptors Proteins 0.000 title claims description 13
- 239000003446 ligand Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 307
- 238000002360 preparation method Methods 0.000 claims abstract description 24
- 101800000989 Oxytocin Proteins 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 70
- -1 1, 3-dioxolan-2-yl Chemical group 0.000 claims description 69
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 66
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000005936 piperidyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 150000004677 hydrates Chemical class 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 claims description 12
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 12
- 229960001723 oxytocin Drugs 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
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- 125000001424 substituent group Chemical group 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 claims description 6
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- 125000005843 halogen group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004429 atom Chemical group 0.000 claims description 4
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
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- 239000011737 fluorine Substances 0.000 claims description 3
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- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
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- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 1
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- 238000012876 topography Methods 0.000 claims 1
- 102400000050 Oxytocin Human genes 0.000 abstract 1
- 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 abstract 1
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- BWQXMLQIHNWGGW-UHFFFAOYSA-N ethyl 5-chloro-3-(2-chlorophenyl)-1-[(2,4-dimethoxyphenyl)methyl]-2-oxoindole-3-carboxylate Chemical compound C(C)OC(=O)C1(C(N(C2=CC=C(C=C12)Cl)CC1=C(C=C(C=C1)OC)OC)=O)C1=C(C=CC=C1)Cl BWQXMLQIHNWGGW-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
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- 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
- C07D401/10—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 carbon chain containing aromatic rings
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- 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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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0004193A FR2807038B1 (fr) | 2000-04-03 | 2000-04-03 | Nouveaux derives d'indolin-2-one, leur preparation et les compositions pharmaceutiques les contenant |
PCT/FR2001/000980 WO2001074775A1 (fr) | 2000-04-03 | 2001-04-02 | Derives d'indolin-2-one et leur utilisation en tant que ligands des recepteurs de l'ocytocine |
Publications (1)
Publication Number | Publication Date |
---|---|
UA73163C2 true UA73163C2 (en) | 2005-06-15 |
Family
ID=8848777
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA2002097763A UA73163C2 (en) | 2000-04-03 | 2001-02-04 | Indilyn-2-one derivatives, method for obtaining thereof and use as ligands of oxytocin receptor |
Country Status (35)
Country | Link |
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US (2) | US20040059132A1 (et) |
EP (1) | EP1272468B1 (et) |
JP (1) | JP2003529586A (et) |
KR (1) | KR100765028B1 (et) |
CN (1) | CN1224614C (et) |
AR (1) | AR034547A1 (et) |
AT (1) | ATE282593T1 (et) |
AU (2) | AU2001246671B2 (et) |
BR (1) | BR0109814A (et) |
CA (1) | CA2404592A1 (et) |
CZ (1) | CZ20023297A3 (et) |
DE (1) | DE60107221T2 (et) |
DK (1) | DK1272468T3 (et) |
EA (1) | EA005093B1 (et) |
EE (1) | EE05002B1 (et) |
ES (1) | ES2232610T3 (et) |
FR (1) | FR2807038B1 (et) |
HK (1) | HK1050004A1 (et) |
HU (1) | HUP0303109A3 (et) |
IL (1) | IL152085A0 (et) |
IS (1) | IS2458B (et) |
ME (1) | MEP24308A (et) |
MX (1) | MXPA02009773A (et) |
NO (1) | NO324314B1 (et) |
NZ (1) | NZ521617A (et) |
PL (1) | PL358222A1 (et) |
PT (1) | PT1272468E (et) |
SI (1) | SI1272468T1 (et) |
SK (1) | SK14272002A3 (et) |
TR (1) | TR200202288T2 (et) |
TW (1) | TWI225860B (et) |
UA (1) | UA73163C2 (et) |
WO (1) | WO2001074775A1 (et) |
YU (1) | YU80902A (et) |
ZA (1) | ZA200207802B (et) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE477811T1 (de) * | 2002-10-03 | 2010-09-15 | Neuropharmacology Services Llc | Oxytocin zur behandlung von autismus und asperger-syndrom |
TWI289141B (en) | 2003-03-11 | 2007-11-01 | Hoffmann La Roche F. Ag. | Quinolinone derivatives and uses thereof |
FR2875499B1 (fr) * | 2004-09-20 | 2006-10-27 | Sanofi Aventis Sa | Nouveaux derives pyridiniques d'indolin-2-one, leur preparation et leur application en therapeutique |
AR053710A1 (es) | 2005-04-11 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos espiroheterociclicos y sus usos como agentes terapeuticos |
AR056968A1 (es) | 2005-04-11 | 2007-11-07 | Xenon Pharmaceuticals Inc | Compuestos espiro-oxindol y composiciones farmacéuticas |
AR056317A1 (es) * | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
RU2385735C2 (ru) * | 2005-05-10 | 2010-04-10 | Ферринг Интернэшнл Сентер С.А. | Применение антагонистов окситоцина при вспомогательной репродукции |
WO2007063123A1 (de) * | 2005-12-02 | 2007-06-07 | Abbott Gmbh & Co. Kg | Substituierte oxindol-derivate, diese enthaltende arzneimittel und deren verwendung |
US7855194B2 (en) | 2006-03-27 | 2010-12-21 | Hoffmann-La Roche Inc. | Pyrimidine, quinazoline, pteridine and triazine derivatives |
WO2007120102A1 (en) * | 2006-04-19 | 2007-10-25 | Astrazeneca Ab | New substituted oxindole derivatives |
MX2009003876A (es) | 2006-10-12 | 2009-05-11 | Xenon Pharmaceuticals Inc | Uso de compuestos de espiro-oxindol como agentes terapeuticos. |
WO2008046083A2 (en) * | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Use of oxindole compounds as therapeutic agents |
FR2909668B1 (fr) * | 2006-12-12 | 2009-01-23 | Sanofi Aventis Sa | Derives de 5-alkyloxy-indolin-2-one,leur preparation et leurs applications en therapeutique |
CA2741024A1 (en) | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
KR101286323B1 (ko) | 2008-10-17 | 2013-07-15 | 제논 파마슈티칼스 인크. | 스피로-옥스인돌 화합물 및 치료제로서의 그의 용도 |
AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
MY165579A (en) | 2009-10-14 | 2018-04-05 | Xenon Pharmaceuticals Inc | Synthetic methods for spiro-oxindole compounds |
CN105726531A (zh) | 2010-02-26 | 2016-07-06 | 泽农医药公司 | 用于局部给药的螺-羟吲哚化合物的药物组合物及其作为治疗剂的用途 |
CN103623268B (zh) * | 2013-12-04 | 2015-07-15 | 张国显 | 神经康复再造丸及其制备方法 |
CN103830666B (zh) * | 2014-02-14 | 2016-02-10 | 孔祥英 | 一种治疗高血压的中药足浴组合物 |
CN104402886B (zh) * | 2014-09-18 | 2017-01-25 | 陕西科技大学 | 一种具有抗肿瘤活性的7‑氮杂靛红类双螺环化合物及其合成方法 |
CN104230786B (zh) * | 2014-09-26 | 2017-03-22 | 陕西科技大学 | 一种具有抗肿瘤活性的含吲哚结构的化合物及其合成方法 |
WO2016127068A1 (en) | 2015-02-05 | 2016-08-11 | Teva Pharmaceuticals International Gmbh | Methods of treating postherpetic neuralgia with a topical formulation of a spiro-oxindole compound |
CA3002489C (en) | 2015-11-06 | 2023-11-07 | F.Hoffmann-La Roche Ag | Indolin-2-one derivatives |
US20170204087A1 (en) * | 2016-01-20 | 2017-07-20 | Chemocentryx, Inc. | 2-oxindole compounds |
CN109232290A (zh) * | 2018-11-07 | 2019-01-18 | 陕西科技大学 | 一种含氟酰胺及其制备方法 |
CN109678781B (zh) * | 2018-12-20 | 2022-03-29 | 苏州麦迪耐斯医药科技有限公司 | 一种刺猬通路抑制剂 |
EP3912625A1 (en) | 2020-05-20 | 2021-11-24 | Kaerus Bioscience Limited | Novel maxi-k potassium channel openers for the treatment of fragile x associated disorders |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3529994A1 (de) * | 1985-08-22 | 1987-02-26 | Hoechst Ag | Indolinonderivate, verfahren zu ihrer herstellung, sie enthaltende arzneimittel und deren verwendung |
US5206261A (en) * | 1989-07-25 | 1993-04-27 | Taiho Pharmaceutical Company, Limited | Oxindole derivative |
US5686624A (en) * | 1992-01-30 | 1997-11-11 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
FR2708605A1 (fr) * | 1993-07-30 | 1995-02-10 | Sanofi Sa | Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
FR2714378B1 (fr) * | 1993-12-24 | 1996-03-15 | Sanofi Sa | Dérivés de l'indol-2-one substitués en 3 par un groupe azoté, leur préparation, les compositions pharmaceutiques en contenant. |
JPH10338672A (ja) * | 1996-07-16 | 1998-12-22 | Takeda Chem Ind Ltd | 排尿調節剤および2環性化合物 |
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2000
- 2000-04-03 FR FR0004193A patent/FR2807038B1/fr not_active Expired - Fee Related
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2001
- 2001-02-04 UA UA2002097763A patent/UA73163C2/uk unknown
- 2001-03-30 AR ARP010101541A patent/AR034547A1/es unknown
- 2001-04-02 HU HU0303109A patent/HUP0303109A3/hu unknown
- 2001-04-02 ME MEP-243/08A patent/MEP24308A/xx unknown
- 2001-04-02 EA EA200200912A patent/EA005093B1/ru not_active IP Right Cessation
- 2001-04-02 AT AT01919610T patent/ATE282593T1/de active
- 2001-04-02 TR TR2002/02288T patent/TR200202288T2/xx unknown
- 2001-04-02 PT PT01919610T patent/PT1272468E/pt unknown
- 2001-04-02 EP EP01919610A patent/EP1272468B1/fr not_active Expired - Lifetime
- 2001-04-02 SK SK1427-2002A patent/SK14272002A3/sk unknown
- 2001-04-02 IL IL15208501A patent/IL152085A0/xx not_active IP Right Cessation
- 2001-04-02 SI SI200130294T patent/SI1272468T1/xx unknown
- 2001-04-02 DE DE60107221T patent/DE60107221T2/de not_active Expired - Lifetime
- 2001-04-02 YU YU80902A patent/YU80902A/sh unknown
- 2001-04-02 CA CA002404592A patent/CA2404592A1/fr not_active Abandoned
- 2001-04-02 DK DK01919610T patent/DK1272468T3/da active
- 2001-04-02 BR BR0109814-4A patent/BR0109814A/pt not_active IP Right Cessation
- 2001-04-02 AU AU2001246671A patent/AU2001246671B2/en not_active Ceased
- 2001-04-02 JP JP2001572470A patent/JP2003529586A/ja active Pending
- 2001-04-02 PL PL01358222A patent/PL358222A1/xx not_active Application Discontinuation
- 2001-04-02 NZ NZ521617A patent/NZ521617A/en not_active IP Right Cessation
- 2001-04-02 WO PCT/FR2001/000980 patent/WO2001074775A1/fr active IP Right Grant
- 2001-04-02 EE EEP200200573A patent/EE05002B1/et not_active IP Right Cessation
- 2001-04-02 AU AU4667101A patent/AU4667101A/xx active Pending
- 2001-04-02 KR KR1020027013217A patent/KR100765028B1/ko not_active IP Right Cessation
- 2001-04-02 ES ES01919610T patent/ES2232610T3/es not_active Expired - Lifetime
- 2001-04-02 CN CNB018090303A patent/CN1224614C/zh not_active Expired - Fee Related
- 2001-04-02 CZ CZ20023297A patent/CZ20023297A3/cs unknown
- 2001-04-02 MX MXPA02009773A patent/MXPA02009773A/es active IP Right Grant
- 2001-04-03 TW TW090107916A patent/TWI225860B/zh not_active IP Right Cessation
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2002
- 2002-09-24 IS IS6566A patent/IS2458B/is unknown
- 2002-09-27 ZA ZA200207802A patent/ZA200207802B/en unknown
- 2002-10-02 NO NO20024749A patent/NO324314B1/no not_active IP Right Cessation
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2003
- 2003-03-26 HK HK03102206A patent/HK1050004A1/xx not_active IP Right Cessation
- 2003-09-03 US US10/654,060 patent/US20040059132A1/en not_active Abandoned
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2007
- 2007-05-03 US US11/744,003 patent/US20070203184A1/en not_active Abandoned
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