UA77181C2 - 1-phenylsulfonyl-1,3-dihydro-2h-indol-2-on derivatives, their production and therapeutic use - Google Patents
1-phenylsulfonyl-1,3-dihydro-2h-indol-2-on derivatives, their production and therapeutic use Download PDFInfo
- Publication number
- UA77181C2 UA77181C2 UA20031212069A UA20031212069A UA77181C2 UA 77181 C2 UA77181 C2 UA 77181C2 UA 20031212069 A UA20031212069 A UA 20031212069A UA 20031212069 A UA20031212069 A UA 20031212069A UA 77181 C2 UA77181 C2 UA 77181C2
- Authority
- UA
- Ukraine
- Prior art keywords
- mixture
- dihydro
- chloro
- indol
- compound
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 230000001225 therapeutic effect Effects 0.000 title description 3
- HBORMJBGPGQHSF-UHFFFAOYSA-N 1-(benzenesulfonyl)-3h-indol-2-one Chemical class O=C1CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 HBORMJBGPGQHSF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 544
- 238000000034 method Methods 0.000 claims abstract description 126
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- 239000012453 solvate Substances 0.000 claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 5
- 229940079593 drug Drugs 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 441
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 100
- -1 ethoxyl Chemical group 0.000 claims description 54
- JYGFTBXVXVMTGB-UHFFFAOYSA-N Oxindol Natural products C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 23
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 19
- 239000011707 mineral Substances 0.000 claims description 19
- IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 15
- 150000004677 hydrates Chemical class 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 150000007522 mineralic acids Chemical class 0.000 claims description 13
- 150000007524 organic acids Chemical class 0.000 claims description 13
- 235000005985 organic acids Nutrition 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 9
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 6
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
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- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- XSCAGNLSEVMMSV-UHFFFAOYSA-N 1H-indol-3-yl 4-pyridin-4-ylpiperazine-1-carboxylate Chemical compound N1C=C(C2=CC=CC=C12)OC(=O)N1CCN(CC1)C1=CC=NC=C1 XSCAGNLSEVMMSV-UHFFFAOYSA-N 0.000 claims 1
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- 244000203593 Piper nigrum Species 0.000 claims 1
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- 239000011148 porous material Substances 0.000 claims 1
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- 238000012876 topography Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 91
- 239000002253 acid Substances 0.000 abstract description 19
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 abstract description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 348
- 239000000047 product Substances 0.000 description 207
- 239000002904 solvent Substances 0.000 description 163
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 136
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 103
- 239000012074 organic phase Substances 0.000 description 103
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 91
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- 238000002425 crystallisation Methods 0.000 description 87
- 230000008025 crystallization Effects 0.000 description 87
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 75
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- 229910002027 silica gel Inorganic materials 0.000 description 75
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
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- 235000019439 ethyl acetate Nutrition 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
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- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
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- 238000006243 chemical reaction Methods 0.000 description 29
- AYGZKRRIULCJKC-UHFFFAOYSA-N 2,4-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C(OC)=C1 AYGZKRRIULCJKC-UHFFFAOYSA-N 0.000 description 27
- OQZBAQXTXNIPRA-UHFFFAOYSA-N 1-pyridin-4-ylpiperazine Chemical compound C1CNCCN1C1=CC=NC=C1 OQZBAQXTXNIPRA-UHFFFAOYSA-N 0.000 description 26
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
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- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 25
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- 238000009835 boiling Methods 0.000 description 23
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 23
- 239000012047 saturated solution Substances 0.000 description 22
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 19
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
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- 239000011734 sodium Substances 0.000 description 16
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- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 9
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
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- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
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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
- C07D401/14—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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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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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0110359A FR2827604B1 (fr) | 2001-07-17 | 2001-07-17 | Nouveaux derives de 1-phenylsulfonyl-1,3-dihydro-2h-indol-2- one, un procede pour leur preparation et les compositions pharmaceutiques en contenant |
PCT/FR2002/002500 WO2003008407A2 (fr) | 2001-07-17 | 2002-07-15 | Derives de 1-phenylsulfonyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique |
Publications (1)
Publication Number | Publication Date |
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UA77181C2 true UA77181C2 (en) | 2006-11-15 |
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ID=8866211
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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UA20031212069A UA77181C2 (en) | 2001-07-17 | 2002-07-15 | 1-phenylsulfonyl-1,3-dihydro-2h-indol-2-on derivatives, their production and therapeutic use |
Country Status (32)
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US (1) | US7119086B2 (de) |
EP (1) | EP1419150B1 (de) |
JP (1) | JP4262088B2 (de) |
KR (1) | KR20040017325A (de) |
CN (1) | CN1224623C (de) |
AR (1) | AR034792A1 (de) |
AT (1) | ATE294171T1 (de) |
AU (1) | AU2002340999B2 (de) |
BR (1) | BR0211284A (de) |
CA (1) | CA2450437A1 (de) |
CO (1) | CO5550440A2 (de) |
DE (1) | DE60203917T2 (de) |
DK (1) | DK1419150T3 (de) |
EA (1) | EA006019B1 (de) |
ES (1) | ES2240814T3 (de) |
FR (1) | FR2827604B1 (de) |
HK (1) | HK1061679A1 (de) |
HR (1) | HRP20040027A2 (de) |
HU (1) | HUP0401461A3 (de) |
IL (1) | IL159275A0 (de) |
IS (1) | IS2485B (de) |
MA (1) | MA27049A1 (de) |
ME (1) | MEP24508A (de) |
MX (1) | MXPA04000507A (de) |
NO (1) | NO20040219L (de) |
NZ (1) | NZ530144A (de) |
PL (1) | PL366829A1 (de) |
PT (1) | PT1419150E (de) |
RS (1) | RS204A (de) |
UA (1) | UA77181C2 (de) |
WO (1) | WO2003008407A2 (de) |
ZA (1) | ZA200309717B (de) |
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WO2005021534A1 (ja) | 2003-08-28 | 2005-03-10 | Taisho Pharmaceutical Co., Ltd. | 1,3−ジヒドロ−2h−インドール−2−オン誘導体 |
US8580842B2 (en) * | 2003-09-30 | 2013-11-12 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
US20050070718A1 (en) * | 2003-09-30 | 2005-03-31 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
AU2005237520B2 (en) | 2004-04-27 | 2012-01-19 | Wyeth | Purification of progesterone receptor modulators |
DE102004033834A1 (de) * | 2004-07-13 | 2006-02-02 | Abbott Gmbh & Co. Kg | Substituierte Oxindol-Derivate und diese enthaltende Arzneimittel |
JPWO2006070742A1 (ja) * | 2004-12-27 | 2008-08-07 | 国立大学法人京都大学 | 麻薬性鎮痛剤の耐性形成抑制剤 |
WO2006080574A1 (ja) * | 2005-01-28 | 2006-08-03 | Taisho Pharmaceutical Co., Ltd. | 1,3-ジヒドロ-2h-インドール-2-オン化合物、及び芳香族複素環が縮合したピロリジン-2-オン化合物 |
MX2007011693A (es) | 2005-03-24 | 2008-03-11 | Abbott Gmbh & Co Kg | Derivados de oxindoles sustituidos, farmacos que contienen dichos derivados y uso de los mismos. |
DE102005014904A1 (de) * | 2005-03-26 | 2007-02-01 | Abbott Gmbh & Co. Kg | Substituierte Oxindol-Derivate, diese enthaltende Arzneimittel und deren Verwendung |
DE102005014936A1 (de) * | 2005-03-24 | 2006-12-14 | Abbott Gmbh & Co. Kg | Substituierte Oxindol-Derivate, diese enthaltende Arzneimittel und deren Verwendung |
US7576082B2 (en) | 2005-06-24 | 2009-08-18 | Hoffman-La Roche Inc. | Oxindole derivatives |
SG132540A1 (en) | 2005-11-25 | 2007-06-28 | Matsushita Electric Ind Co Ltd | Magnetic trap for ferrous contaminants in lubricant |
US8044079B2 (en) | 2005-12-02 | 2011-10-25 | Abbott Gmbh & Co. Kg | Substituted oxindole derivatives, medicaments containing said derivatives and use thereof |
MX2009002125A (es) * | 2006-08-26 | 2009-03-09 | Abbott Gmbh & Co Kg | Derivados de benzimidazolona sustituidos, medicamentos que los comprenden y su uso. |
DE102006040915A1 (de) * | 2006-08-26 | 2008-03-20 | Abbott Gmbh & Co. Kg | Substituierte Oxindol-Derivate, diese enthaltende Arzneimittel und deren Verwendung |
US8486979B2 (en) | 2006-12-12 | 2013-07-16 | Abbvie Inc. | 1,2,4 oxadiazole compounds and methods of use thereof |
US20080167286A1 (en) | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
RU2461556C2 (ru) * | 2006-12-30 | 2012-09-20 | Эбботт Гмбх Унд Ко. Кг | Замещенные производные оксидола и их применение в качестве лигандов рецептора вазопрессина |
CL2007003878A1 (es) * | 2006-12-30 | 2008-07-04 | Basf Ag | Compuestos derivados de 2-oxo-indol sustituido, moduladores del receptor de vasopresina; proceso de preparacion; composicion farmaceutica; y uso en el tratamiento y/o profilaxis de enfermedades tales como diabetes, resistencia a la insulina, incontin |
UY30846A1 (es) | 2006-12-30 | 2008-07-31 | Abbott Gmbh & Amp | Derivados de oxindol sustituidos, medicamentos que los comprenden y uso de los mismos |
US8486931B2 (en) * | 2007-03-02 | 2013-07-16 | Abbott Gmbh & Co. Kg | Substituted oxindole compounds |
FR2920023B1 (fr) * | 2007-08-16 | 2013-02-08 | Sanofi Aventis | Derives de l'indol-2-one disubstitues en 3, leur preparation et leur application en therapeutique |
CN101952276B (zh) | 2007-12-07 | 2014-10-22 | Abbvie德国有限责任两合公司 | 5-卤素取代的羟吲哚衍生物和其用于治疗加压素依赖性疾病的用途 |
CA2707671C (en) | 2007-12-07 | 2016-02-02 | Abbott Gmbh & Co. Kg | 5,6-disubstituted oxindole-derivatives and use thereof for treating vasopressine-dependent diseases |
US8703774B2 (en) * | 2007-12-07 | 2014-04-22 | AbbVie Deutschland GmbH & Co. KG | Carbamate-substituted oxindole derivatives and use thereof for the treatment of vasopressin-dependent diseases |
MX2010006202A (es) | 2007-12-07 | 2011-03-04 | Abbott Gmbh & Co Kg | Derivados de oxindol substituidos por amidometil y el uso de los mismos para el tratamiento de enfermedades dependientes de la vasopresina. |
WO2009071691A2 (de) * | 2007-12-07 | 2009-06-11 | Abbott Gmbh & Co. Kg | Oxindol-derivate und ihre verwendung als medikament |
EP2227463B1 (de) * | 2007-12-27 | 2016-08-17 | AbbVie Deutschland GmbH & Co KG | Substituierte oxindol-derivate und ihre verwendung zur behandlung von vasopressin-abhängigen erkrankungen |
FR2927625B1 (fr) * | 2008-02-19 | 2010-03-12 | Sanofi Aventis | Nouveaux derives de 3-aminoalkyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique |
FR2930249B1 (fr) * | 2008-04-21 | 2010-05-14 | Sanofi Aventis | Nouveaux derives de 3-aminoalkyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique. |
WO2010017827A1 (en) * | 2008-08-14 | 2010-02-18 | European Molecular Biology Laboratory | 6-substituted 1-sulfonyl-2, 3-dihydro-indole derivatives for the treatment of proliferative diseases |
EP3228320B1 (de) | 2008-10-17 | 2019-12-18 | Sanofi-Aventis Deutschland GmbH | Kombination von einem insulin und einem glp-1-agonisten |
FR2941946B1 (fr) | 2009-02-12 | 2011-03-25 | Sanofi Aventis | Derives de 3-benzofuranyl-indol-2-one-3-acetamidopiperazines substitues, leur preparation et leur application en therapeutique |
FR2941947B1 (fr) | 2009-02-12 | 2011-03-25 | Sanofi Aventis | Derives de 3-benzofuranyl-indol-2-one subtitues en 3, leur preparation et leur application en therapeutique |
EP2435080A2 (de) | 2009-05-29 | 2012-04-04 | Abbott Laboratories | Pharmazeutische zusammensetzungen zur schmerzbehandlung |
CA2763931A1 (en) * | 2009-06-10 | 2010-12-16 | Abbott Gmbh & Co. Kg | Use of substituted oxindole derivatives for the treatment and prophylaxis of pain |
AR080669A1 (es) | 2009-11-13 | 2012-05-02 | Sanofi Aventis Deutschland | Composicion farmaceutica que comprende un agonista de glp-1, una insulina y metionina |
UY33025A (es) | 2009-11-13 | 2011-06-30 | Sanofi Aventis Deustschland Gmbh | Composicion farmaceutica que comprende un agonista de glp-1 metionina |
US8088815B2 (en) | 2009-12-02 | 2012-01-03 | Hoffman-La Roche Inc. | Spiroindolinone pyrrolidines |
US8288431B2 (en) | 2010-02-17 | 2012-10-16 | Hoffmann-La Roche Inc. | Substituted spiroindolinones |
US8217044B2 (en) | 2010-04-28 | 2012-07-10 | Hoffmann-La Roche Inc. | Spiroindolinone pyrrolidines |
AU2011202239C1 (en) | 2010-05-19 | 2017-03-16 | Sanofi | Long-acting formulations of insulins |
MX339614B (es) | 2010-08-30 | 2016-06-02 | Sanofi - Aventis Deutschland GmbH | Uso de ave0010 para la fabricacion de un medicamento para el tratamiento de la diabetes mellitus tipo 2. |
EP2655360B1 (de) | 2010-12-21 | 2016-04-20 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von n-sulfonylsubstituierten oxindolen |
US9821032B2 (en) | 2011-05-13 | 2017-11-21 | Sanofi-Aventis Deutschland Gmbh | Pharmaceutical combination for improving glycemic control as add-on therapy to basal insulin |
RU2650616C2 (ru) | 2011-08-29 | 2018-04-16 | Санофи-Авентис Дойчланд Гмбх | Фармацевтическая комбинация для применения при гликемическом контроле у пациентов с сахарным диабетом 2 типа |
TWI559929B (en) | 2011-09-01 | 2016-12-01 | Sanofi Aventis Deutschland | Pharmaceutical composition for use in the treatment of a neurodegenerative disease |
CN110354255B (zh) | 2013-04-03 | 2024-05-14 | 赛诺菲 | 通过长效胰岛素制剂治疗糖尿病 |
CN107206058A (zh) | 2014-12-12 | 2017-09-26 | 赛诺菲-安万特德国有限公司 | 甘精胰岛素/利西拉来固定比率配制剂 |
TWI748945B (zh) | 2015-03-13 | 2021-12-11 | 德商賽諾菲阿凡提斯德意志有限公司 | 第2型糖尿病病患治療 |
TW201705975A (zh) | 2015-03-18 | 2017-02-16 | 賽諾菲阿凡提斯德意志有限公司 | 第2型糖尿病病患之治療 |
EP3912625A1 (de) * | 2020-05-20 | 2021-11-24 | Kaerus Bioscience Limited | Neuartige maxi-k-kaliumkanal-öffner zur behandlung von mit fragilem x assoziierten erkrankungen |
KR20230090589A (ko) * | 2021-12-15 | 2023-06-22 | 국립해양생물자원관 | 성게 유래 펩타이드 및 이의 용도 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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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. |
GB2326639A (en) * | 1997-06-18 | 1998-12-30 | Merck & Co Inc | Piperazine Oxytocin Receptor Antagonists |
US20050070718A1 (en) * | 2003-09-30 | 2005-03-31 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
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2001
- 2001-07-17 FR FR0110359A patent/FR2827604B1/fr not_active Expired - Fee Related
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2002
- 2002-07-15 EA EA200301306A patent/EA006019B1/ru not_active IP Right Cessation
- 2002-07-15 RS YU204A patent/RS204A/sr unknown
- 2002-07-15 DE DE60203917T patent/DE60203917T2/de not_active Expired - Lifetime
- 2002-07-15 NZ NZ530144A patent/NZ530144A/en not_active IP Right Cessation
- 2002-07-15 ES ES02774822T patent/ES2240814T3/es not_active Expired - Lifetime
- 2002-07-15 DK DK02774822T patent/DK1419150T3/da active
- 2002-07-15 WO PCT/FR2002/002500 patent/WO2003008407A2/fr active IP Right Grant
- 2002-07-15 MX MXPA04000507A patent/MXPA04000507A/es active IP Right Grant
- 2002-07-15 KR KR10-2004-7000787A patent/KR20040017325A/ko active IP Right Grant
- 2002-07-15 PL PL02366829A patent/PL366829A1/xx not_active Application Discontinuation
- 2002-07-15 CN CNB028142624A patent/CN1224623C/zh not_active Expired - Fee Related
- 2002-07-15 IL IL15927502A patent/IL159275A0/xx unknown
- 2002-07-15 HU HU0401461A patent/HUP0401461A3/hu unknown
- 2002-07-15 PT PT02774822T patent/PT1419150E/pt unknown
- 2002-07-15 AU AU2002340999A patent/AU2002340999B2/en not_active Ceased
- 2002-07-15 CA CA002450437A patent/CA2450437A1/en not_active Abandoned
- 2002-07-15 JP JP2003513966A patent/JP4262088B2/ja not_active Expired - Fee Related
- 2002-07-15 BR BR0211284-1A patent/BR0211284A/pt not_active IP Right Cessation
- 2002-07-15 ME MEP-245/08A patent/MEP24508A/xx unknown
- 2002-07-15 AT AT02774822T patent/ATE294171T1/de active
- 2002-07-15 UA UA20031212069A patent/UA77181C2/uk unknown
- 2002-07-15 US US10/484,370 patent/US7119086B2/en not_active Expired - Fee Related
- 2002-07-15 EP EP02774822A patent/EP1419150B1/de not_active Expired - Lifetime
- 2002-07-16 AR ARP020102655A patent/AR034792A1/es unknown
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2003
- 2003-12-15 IS IS7079A patent/IS2485B/is unknown
- 2003-12-15 ZA ZA200309717A patent/ZA200309717B/en unknown
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2004
- 2004-01-09 MA MA27476A patent/MA27049A1/fr unknown
- 2004-01-12 HR HR20040027A patent/HRP20040027A2/xx not_active Application Discontinuation
- 2004-01-14 CO CO04002002A patent/CO5550440A2/es not_active Application Discontinuation
- 2004-01-16 NO NO20040219A patent/NO20040219L/no not_active Application Discontinuation
- 2004-06-25 HK HK04104546A patent/HK1061679A1/xx not_active IP Right Cessation
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