NO323607B1 - Nye 1,3-dihydro-2H-indol-2-on-derivater, fremgangsmate for deres fremstilling samt farmasoytisk preparat. - Google Patents
Nye 1,3-dihydro-2H-indol-2-on-derivater, fremgangsmate for deres fremstilling samt farmasoytisk preparat. Download PDFInfo
- Publication number
- NO323607B1 NO323607B1 NO20023510A NO20023510A NO323607B1 NO 323607 B1 NO323607 B1 NO 323607B1 NO 20023510 A NO20023510 A NO 20023510A NO 20023510 A NO20023510 A NO 20023510A NO 323607 B1 NO323607 B1 NO 323607B1
- Authority
- NO
- Norway
- Prior art keywords
- dihydro
- indol
- oxo
- dimethoxyphenyl
- compound
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 156
- 238000000034 method Methods 0.000 title claims description 51
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 336
- 239000000203 mixture Substances 0.000 claims description 241
- -1 trifluoromethoxy radical Chemical class 0.000 claims description 71
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 20
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
- 150000007513 acids Chemical class 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 12
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 12
- 239000011707 mineral Substances 0.000 claims description 12
- 235000005985 organic acids Nutrition 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000004677 hydrates Chemical class 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- NJXZWIIMWNEOGJ-SKOIZEAASA-N (2s,4r)-1-[5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O NJXZWIIMWNEOGJ-SKOIZEAASA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- SPRCUXTZMGDNBL-XZCJNAJTSA-N (2s,4r)-1-[5-chloro-3-(2-chlorophenyl)-1-(2,4-dimethoxyphenyl)sulfonyl-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=CC=CC=2)Cl)C1=O SPRCUXTZMGDNBL-XZCJNAJTSA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 2
- XDFLWOGIYWRKOA-MUUVGFCSSA-N (2s,4r)-1-[1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-n,n-dimethyl-4-(2-morpholin-4-yl-2-oxoethoxy)pyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(N2[C@@H](C[C@H](C2)OCC(=O)N2CCOCC2)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O XDFLWOGIYWRKOA-MUUVGFCSSA-N 0.000 claims description 2
- YGEWINJEZZTCMB-OFINDPKTSA-N (2s,4r)-1-[1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-5-methyl-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(C)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O YGEWINJEZZTCMB-OFINDPKTSA-N 0.000 claims description 2
- PGMHTTXEKSSCBM-LDHGLFKHSA-N (2s,4r)-1-[3-(1,3-benzodioxol-4-yl)-5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C=3OCOC=3C=CC=2)C1=O PGMHTTXEKSSCBM-LDHGLFKHSA-N 0.000 claims description 2
- OYYHXQDBUWFRKD-OCEHLNNUSA-N (2s,4r)-1-[3-(2-chlorophenyl)-1-(2,4-dimethoxyphenyl)sulfonyl-5,6-dimethyl-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC(C)=C(C)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=CC=CC=2)Cl)C1=O OYYHXQDBUWFRKD-OCEHLNNUSA-N 0.000 claims description 2
- ARUVGFCZTISCCH-COPKTGQBSA-N (2s,4r)-1-[5,6-dichloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC(Cl)=C(Cl)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O ARUVGFCZTISCCH-COPKTGQBSA-N 0.000 claims description 2
- LEKCNLVBHMHCPW-YXSPYMROSA-N (2s,4r)-1-[5,6-dichloro-3-(2-chlorophenyl)-1-(2,4-dimethoxyphenyl)sulfonyl-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC(Cl)=C(Cl)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=CC=CC=2)Cl)C1=O LEKCNLVBHMHCPW-YXSPYMROSA-N 0.000 claims description 2
- TXRGWMYGRUQNKV-WJUPYNHCSA-N (2s,4r)-1-[5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-4-ethoxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound C1[C@H](OCC)C[C@@H](C(=O)N(C)C)N1C1(C=2C(=CC=CC=2)OC)C2=CC(Cl)=CC=C2N(S(=O)(=O)C=2C(=CC(OC)=CC=2)OC)C1=O TXRGWMYGRUQNKV-WJUPYNHCSA-N 0.000 claims description 2
- 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 description 2
- GGXNHJCJOSYILY-XJHDQSROSA-N (2s,4r)-1-[5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-6-methyl-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC(C)=C(Cl)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O GGXNHJCJOSYILY-XJHDQSROSA-N 0.000 claims description 2
- BOZNTEYPVWIJMN-KDYYCBBQSA-N (2s,4r)-1-[5-chloro-3-(2,3-difluorophenyl)-1-(2,4-dimethoxyphenyl)sulfonyl-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=C(F)C=CC=2)F)C1=O BOZNTEYPVWIJMN-KDYYCBBQSA-N 0.000 claims description 2
- UOEOYFKUZQPERI-KLYJSIMZSA-N (2s,4r)-1-[5-chloro-3-(2,3-dimethoxyphenyl)-1-(2,4-dimethoxyphenyl)sulfonyl-2-oxoindol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=C(OC)C=CC=2)OC)C1=O UOEOYFKUZQPERI-KLYJSIMZSA-N 0.000 claims description 2
- XZLVMYJWPCPBCQ-NYUADOPNSA-N (2s,4r)-1-[5-chloro-3-(2,3-dimethoxyphenyl)-1-(2,4-dimethoxyphenyl)sulfonyl-2-oxoindol-3-yl]-4-methoxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound C1[C@H](OC)C[C@@H](C(=O)N(C)C)N1C1(C=2C(=C(OC)C=CC=2)OC)C2=CC(Cl)=CC=C2N(S(=O)(=O)C=2C(=CC(OC)=CC=2)OC)C1=O XZLVMYJWPCPBCQ-NYUADOPNSA-N 0.000 claims description 2
- CESREZNYNNXKAO-AYAVOSLBSA-N (2s,4r)-1-[6-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-5-methyl-2-oxoindol-3-yl]-4-methoxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound C1[C@H](OC)C[C@@H](C(=O)N(C)C)N1C1(C=2C(=CC=CC=2)OC)C2=CC(C)=C(Cl)C=C2N(S(=O)(=O)C=2C(=CC(OC)=CC=2)OC)C1=O CESREZNYNNXKAO-AYAVOSLBSA-N 0.000 claims description 2
- ZMTPQDAOWQAMKA-NYUADOPNSA-N 2-[(3r,5s)-1-[5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-5-(dimethylcarbamoyl)pyrrolidin-3-yl]oxyacetic acid Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(N2[C@@H](C[C@H](C2)OCC(O)=O)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O ZMTPQDAOWQAMKA-NYUADOPNSA-N 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims description 2
- AMXBARSXKOEJKM-LBTBCUSVSA-N methyl (2s,4r)-1-[5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-4-methoxypyrrolidine-2-carboxylate Chemical compound C1[C@H](OC)C[C@@H](C(=O)OC)N1C1(C=2C(=CC=CC=2)OC)C2=CC(Cl)=CC=C2N(S(=O)(=O)C=2C(=CC(OC)=CC=2)OC)C1=O AMXBARSXKOEJKM-LBTBCUSVSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- OXCWTDNWUZLPQS-RGEVILCCSA-N tert-butyl 2-[(3r,5s)-1-[5-chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-5-(dimethylcarbamoyl)pyrrolidin-3-yl]oxyacetate Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(N2[C@@H](C[C@H](C2)OCC(=O)OC(C)(C)C)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O OXCWTDNWUZLPQS-RGEVILCCSA-N 0.000 claims description 2
- JJNTYUAMTWOIEC-HLFJGWCOSA-N (2s,4r)-1-[1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxo-5-(trifluoromethoxy)indol-3-yl]-4-hydroxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC(F)(F)F)C=C2C(N2[C@@H](C[C@@H](O)C2)C(=O)N(C)C)(C=2C(=CC=CC=2)OC)C1=O JJNTYUAMTWOIEC-HLFJGWCOSA-N 0.000 claims 1
- YFWACMZACKJZOU-XJHDQSROSA-N (2s,4r)-1-[5-chloro-3-(2-chlorophenyl)-1-(2,4-dimethoxyphenyl)sulfonyl-6-methoxy-2-oxoindol-3-yl]-4-methoxy-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound C1[C@H](OC)C[C@@H](C(=O)N(C)C)N1C1(C=2C(=CC=CC=2)Cl)C2=CC(Cl)=C(OC)C=C2N(S(=O)(=O)C=2C(=CC(OC)=CC=2)OC)C1=O YFWACMZACKJZOU-XJHDQSROSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 348
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
- 239000000243 solution Substances 0.000 description 145
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 128
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 104
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
- 239000000047 product Substances 0.000 description 95
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- 239000002904 solvent Substances 0.000 description 81
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
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- 239000000460 chlorine Substances 0.000 description 73
- 235000019439 ethyl acetate Nutrition 0.000 description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
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- 239000000741 silica gel Substances 0.000 description 53
- 229910002027 silica gel Inorganic materials 0.000 description 53
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- 238000010828 elution Methods 0.000 description 46
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 44
- 239000011734 sodium Substances 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 35
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
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- 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 description 26
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Classifications
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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
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- 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
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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 (3)
Publication Number | Publication Date |
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NO20023510D0 NO20023510D0 (no) | 2002-07-23 |
NO20023510L NO20023510L (no) | 2002-09-25 |
NO323607B1 true NO323607B1 (no) | 2007-06-18 |
Family
ID=8846307
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20023510A NO323607B1 (no) | 2000-01-25 | 2002-07-23 | Nye 1,3-dihydro-2H-indol-2-on-derivater, fremgangsmate for deres fremstilling samt farmasoytisk preparat. |
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EP (1) | EP1255751B1 (hu) |
JP (1) | JP3992498B2 (hu) |
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CN (1) | CN1193025C (hu) |
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AT (1) | ATE269326T1 (hu) |
AU (1) | AU778196B2 (hu) |
BG (1) | BG65796B1 (hu) |
BR (1) | BR0107807B1 (hu) |
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DK (1) | DK1255751T3 (hu) |
EA (1) | EA004628B1 (hu) |
EE (1) | EE04779B1 (hu) |
ES (1) | ES2222342T3 (hu) |
FR (1) | FR2804114B1 (hu) |
HK (1) | HK1050900A1 (hu) |
HR (1) | HRP20020626B1 (hu) |
HU (1) | HU229081B1 (hu) |
IL (2) | IL150539A0 (hu) |
IS (1) | IS2313B (hu) |
ME (1) | MEP17308A (hu) |
MX (1) | MXPA02007259A (hu) |
NO (1) | NO323607B1 (hu) |
PL (1) | PL204160B1 (hu) |
PT (1) | PT1255751E (hu) |
RS (1) | RS50290B (hu) |
SI (1) | SI1255751T1 (hu) |
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TR (1) | TR200402344T4 (hu) |
TW (1) | TWI283672B (hu) |
UA (1) | UA74354C2 (hu) |
WO (1) | WO2001055130A2 (hu) |
ZA (1) | ZA200205224B (hu) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
EP1659121A4 (en) | 2003-08-28 | 2008-11-26 | Taisho Pharmaceutical Co Ltd | D RIV OF 1,3-DIHYDRO-2H-INDOL-2-ONE |
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 |
US20080227802A1 (en) * | 2004-12-27 | 2008-09-18 | Kyoto University | Agent For Suppressing Development of Tolerance to Narcotic Analgesics |
JP2008526702A (ja) * | 2004-12-31 | 2008-07-24 | アボット ゲーエムベーハー ウント カンパニー カーゲー | 置換オキシインドール誘導体、該誘導体を含んでいる薬物及びそれらの使用 |
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 |
TW200643015A (en) | 2005-03-11 | 2006-12-16 | Akzo Nobel Nv | 2-(4-oxo-4H-quinazolin-3-yl)acetamide derivatives |
CN101258134B (zh) * | 2005-03-11 | 2011-10-12 | 欧加农股份有限公司 | 2-(4-氧代-4h-喹唑啉-3-基)乙酰胺衍生物及其作为加压素v3拮抗剂的用途 |
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 |
EP1861392A2 (de) * | 2005-03-24 | 2007-12-05 | Abbott GmbH & Co. KG | Substituierte oxindol-derivate, diese enthaltende arzneimittel und deren verwendung |
EP1890697B1 (en) | 2005-06-07 | 2015-03-04 | Pharmacopeia, LLC | Azinone and diazinone v3 inhibitors for depression and stress disorders |
US7576082B2 (en) | 2005-06-24 | 2009-08-18 | Hoffman-La Roche Inc. | Oxindole derivatives |
AU2006270039B2 (en) * | 2005-07-19 | 2013-07-04 | Azevan Pharmaceuticals, Inc. | Beta-lactamyl phenylalanine, cysteine, and serine vasopressin antagonists |
CN101336239A (zh) | 2005-12-02 | 2008-12-31 | 艾博特股份有限两合公司 | 经取代的羟吲哚衍生物,含有该衍生物的药物及其用途 |
CN101033209B (zh) * | 2006-03-09 | 2014-08-27 | 上海医药工业研究院 | 药物中间体(2s,4r)-4-羟基-n,n-二甲基-2-吡咯烷甲酰胺的制备方法 |
DE102006040915A1 (de) | 2006-08-26 | 2008-03-20 | Abbott Gmbh & Co. Kg | Substituierte Oxindol-Derivate, diese enthaltende Arzneimittel und deren Verwendung |
MX2009002125A (es) | 2006-08-26 | 2009-03-09 | Abbott Gmbh & Co Kg | Derivados de benzimidazolona sustituidos, medicamentos que los comprenden y su uso. |
US7820649B2 (en) | 2006-09-11 | 2010-10-26 | N.V. Organon | Quinazolinone and isoquinolinone acetamide derivatives |
US7427008B2 (en) * | 2006-10-25 | 2008-09-23 | Black & Decker Inc. | Depth adjusting device for a power tool |
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 |
MX2009006313A (es) | 2006-12-13 | 2009-06-23 | Organon Nv | Antagonistas v3 para el tratamiento o prevencion de dolor cronico. |
UY30846A1 (es) | 2006-12-30 | 2008-07-31 | Abbott Gmbh & Amp | Derivados de oxindol sustituidos, medicamentos que los comprenden y uso de los mismos |
JP5701607B2 (ja) | 2007-12-07 | 2015-04-15 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | アミドメチル置換オキシインドール誘導体およびバソプレッシン依存性疾患の治療へのこれらの使用 |
MX2010006204A (es) | 2007-12-07 | 2011-03-16 | Abbott Gmbh & Co Kg | Derivados de oxindol 5,6-disubstituidos y el uso de los mismos para el tratamiento de enfermedades dependientes de la vasopresina. |
WO2010009775A1 (de) | 2007-12-07 | 2010-01-28 | Abbott Gmbh & Co. Kg | Carbamat-substituierte oxindol-derivate und ihre verwendung zur behandlung von vasopressin-abhängigen erkrankungen |
NZ586651A (en) * | 2007-12-07 | 2012-06-29 | Abbott Gmbh & Co Kg | 5-halogen-substituted oxindole derivatives and use thereof for treating vasopressine-dependent diseases |
US8629148B2 (en) | 2007-12-27 | 2014-01-14 | AbbVie Deutschland GmbH & Co. KG | Substituted oxindole-derivatives and the use thereof for the treatment of vasopressin-dependent illnesses |
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. |
WO2009140484A1 (en) * | 2008-05-15 | 2009-11-19 | Sanofi-Aventis | Processes for preparing amorphous drug substance |
WO2009140479A1 (en) * | 2008-05-15 | 2009-11-19 | Sanofi-Aventis | Amorphous solid dispersions |
EP2435080A2 (en) | 2009-05-29 | 2012-04-04 | Abbott Laboratories | Pharmaceutical compositions for the treatment of pain |
RU2566754C2 (ru) | 2010-10-01 | 2015-10-27 | Тайсо Фармасьютикал Ко., Лтд. | Производное 1,2,4-триазолона |
WO2013062027A1 (ja) | 2011-10-27 | 2013-05-02 | 大正製薬株式会社 | アゾール誘導体 |
US20150045551A1 (en) | 2012-03-30 | 2015-02-12 | Taisho Pharmaceutical Co., Ltd | Fused azole derivative |
CN103342672B (zh) * | 2013-07-02 | 2015-12-23 | 扬州大学 | 取代吡咯烷-2-酮的新合成方法 |
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US5338755A (en) * | 1990-07-31 | 1994-08-16 | Elf Sanofi | N-sulfonylindoline derivatives, their preparation and the pharmaceutical compositions in which they are present |
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. |
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 |
FR2810320B1 (fr) * | 2000-06-19 | 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 |
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2000
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2001
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- 2001-01-24 PL PL357553A patent/PL204160B1/pl not_active IP Right Cessation
- 2001-01-24 RS YUP-523/02A patent/RS50290B/sr unknown
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- 2001-01-24 EP EP01907685A patent/EP1255751B1/fr not_active Expired - Lifetime
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