SK286976B6 - Deriváty 1,3-dihydro-2H-indol-2-ónu, spôsob ich prípravy a farmaceutická kompozícia, ktorá ich obsahuje - Google Patents
Deriváty 1,3-dihydro-2H-indol-2-ónu, spôsob ich prípravy a farmaceutická kompozícia, ktorá ich obsahuje Download PDFInfo
- Publication number
- SK286976B6 SK286976B6 SK1083-2002A SK10832002A SK286976B6 SK 286976 B6 SK286976 B6 SK 286976B6 SK 10832002 A SK10832002 A SK 10832002A SK 286976 B6 SK286976 B6 SK 286976B6
- Authority
- SK
- Slovakia
- Prior art keywords
- dihydro
- oxo
- dimethoxyphenyl
- indol
- chloro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 345
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 181
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 239000012453 solvate Substances 0.000 claims abstract description 15
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 13
- 150000007524 organic acids Chemical class 0.000 claims abstract description 13
- 235000005985 organic acids Nutrition 0.000 claims abstract description 12
- 150000004677 hydrates Chemical class 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 157
- -1 chloro, methyl Chemical group 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 78
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 42
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 37
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
- 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 claims description 24
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
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- 101800001144 Arg-vasopressin Proteins 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 6
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 4
- BJCVXVGTRUOPRR-MUUVGFCSSA-N (2s,4r)-1-[5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-n,n-dimethyl-4-(2-oxo-2-piperazin-1-ylethoxy)pyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(N2[C@@H](C[C@H](C2)OCC(=O)N2CCNCC2)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O BJCVXVGTRUOPRR-MUUVGFCSSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- XLFKIFVDLHBTIA-UHFFFAOYSA-N n,1-dimethylpyrrolidine-2-carboxamide Chemical compound CNC(=O)C1CCCN1C XLFKIFVDLHBTIA-UHFFFAOYSA-N 0.000 claims 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
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Classifications
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0000957A FR2804114B1 (fr) | 2000-01-25 | 2000-01-25 | Nouveaux derives de 1,3-dihydro-2h-indol-2-one, un procede pour leur preparation et les compositions pharmaceutiques en contenant |
PCT/FR2001/000226 WO2001055130A2 (fr) | 2000-01-25 | 2001-01-24 | Derives de 1,3-dihydro-2h-indol-2-one et leur utilisation en tant que ligands des recepteurs v1b ou v1b et v1a de l'arginine-vasopressine |
Publications (2)
Publication Number | Publication Date |
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SK10832002A3 SK10832002A3 (sk) | 2003-03-04 |
SK286976B6 true SK286976B6 (sk) | 2009-08-06 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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SK1083-2002A SK286976B6 (sk) | 2000-01-25 | 2001-01-24 | Deriváty 1,3-dihydro-2H-indol-2-ónu, spôsob ich prípravy a farmaceutická kompozícia, ktorá ich obsahuje |
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US (3) | US6730695B2 (hr) |
EP (1) | EP1255751B1 (hr) |
JP (1) | JP3992498B2 (hr) |
KR (1) | KR100689922B1 (hr) |
CN (1) | CN1193025C (hr) |
AR (1) | AR027263A1 (hr) |
AT (1) | ATE269326T1 (hr) |
AU (1) | AU778196B2 (hr) |
BG (1) | BG65796B1 (hr) |
BR (1) | BR0107807B1 (hr) |
CA (1) | CA2396814C (hr) |
CZ (1) | CZ300917B6 (hr) |
DE (1) | DE60103853T2 (hr) |
DK (1) | DK1255751T3 (hr) |
EA (1) | EA004628B1 (hr) |
EE (1) | EE04779B1 (hr) |
ES (1) | ES2222342T3 (hr) |
FR (1) | FR2804114B1 (hr) |
HK (1) | HK1050900A1 (hr) |
HR (1) | HRP20020626B1 (hr) |
HU (1) | HU229081B1 (hr) |
IL (2) | IL150539A0 (hr) |
IS (1) | IS2313B (hr) |
ME (1) | MEP17308A (hr) |
MX (1) | MXPA02007259A (hr) |
NO (1) | NO323607B1 (hr) |
PL (1) | PL204160B1 (hr) |
PT (1) | PT1255751E (hr) |
RS (1) | RS50290B (hr) |
SI (1) | SI1255751T1 (hr) |
SK (1) | SK286976B6 (hr) |
TR (1) | TR200402344T4 (hr) |
TW (1) | TWI283672B (hr) |
UA (1) | UA74354C2 (hr) |
WO (1) | WO2001055130A2 (hr) |
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Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2804114B1 (fr) * | 2000-01-25 | 2002-03-08 | Sanofi Synthelabo | Nouveaux derives de 1,3-dihydro-2h-indol-2-one, un procede pour leur preparation et les compositions pharmaceutiques en contenant |
FR2805536B1 (fr) * | 2000-02-25 | 2002-08-23 | Sanofi Synthelabo | Nouveaux derives de 1,3-dihydro-2h-indol-2-one, un procede pour leur preparation et les compositions pharmaceutiques en contenant |
FR2842527B1 (fr) * | 2002-07-19 | 2005-01-28 | Sanofi Synthelabo | Derives d'acyloxypyrolidine, leur preparation et leur application en therapeutique |
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 |
US20050070718A1 (en) * | 2003-09-30 | 2005-03-31 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
US8580842B2 (en) | 2003-09-30 | 2013-11-12 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
US20050165082A1 (en) * | 2003-12-16 | 2005-07-28 | Wyeth | Methods of treating vasomotor symptoms |
US7517899B2 (en) | 2004-03-30 | 2009-04-14 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
US7414052B2 (en) | 2004-03-30 | 2008-08-19 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
WO2006038119A1 (en) * | 2004-10-08 | 2006-04-13 | Warner-Lambert Company Llc | Stereoselective synthesis of n-protected alkoxy prolines |
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 |
EP1831197A2 (de) * | 2004-12-31 | 2007-09-12 | Abbott GmbH & Co. KG | Substituierte oxindol-derivate, diese enthaltende arzneimittel und deren verwendung |
JP5125501B2 (ja) * | 2005-01-28 | 2013-01-23 | 大正製薬株式会社 | 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 |
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MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20130124 |