ZA200207802B - Indolin-2-one derivatives, preparation and their use as ocytocin receptor ligands. - Google Patents
Indolin-2-one derivatives, preparation and their use as ocytocin receptor ligands. Download PDFInfo
- Publication number
- ZA200207802B ZA200207802B ZA200207802A ZA200207802A ZA200207802B ZA 200207802 B ZA200207802 B ZA 200207802B ZA 200207802 A ZA200207802 A ZA 200207802A ZA 200207802 A ZA200207802 A ZA 200207802A ZA 200207802 B ZA200207802 B ZA 200207802B
- Authority
- ZA
- South Africa
- Prior art keywords
- chloro
- group
- methyl
- dimethoxybenzyl
- oxoindolin
- Prior art date
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- 101800000989 Oxytocin Proteins 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000003446 ligand Substances 0.000 title description 5
- 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 title description 5
- 102400000050 Oxytocin Human genes 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000005936 piperidyl group Chemical group 0.000 claims description 24
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- -1 1,3-dioxan-2-yl group Chemical group 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 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 8
- 102000004279 Oxytocin receptors Human genes 0.000 claims description 8
- 108090000876 Oxytocin receptors Proteins 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 150000004677 hydrates Chemical class 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 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 5
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 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 5
- 229960001723 oxytocin Drugs 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 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 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000008602 contraction Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 2
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 210000004291 uterus Anatomy 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 5
- 239000005557 antagonist Substances 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims 2
- 108010004977 Vasopressins Proteins 0.000 claims 2
- 102000002852 Vasopressins Human genes 0.000 claims 2
- 210000000481 breast Anatomy 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 229960003726 vasopressin Drugs 0.000 claims 2
- BBZCPUCZKLTAJQ-UHFFFAOYSA-N 3-methyloxindole Chemical compound C1=CC=C2C(C)C(=O)NC2=C1 BBZCPUCZKLTAJQ-UHFFFAOYSA-N 0.000 claims 1
- HPQXRPLWWKMJCD-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-[2-(dimethylamino)ethyl]-n-ethylbenzamide;hydrochloride Chemical compound Cl.CN(C)CCN(CC)C(=O)C1=CC=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=C1 HPQXRPLWWKMJCD-UHFFFAOYSA-N 0.000 claims 1
- CSIXWVUSWKNWLT-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-cyclohexylbenzamide Chemical compound COC1=CC(OC)=CC=C1CN1C2=CC=C(Cl)C=C2C(C)(C=2C(=CC=C(C=2)C(=O)NC2CCCCC2)Cl)C1=O CSIXWVUSWKNWLT-UHFFFAOYSA-N 0.000 claims 1
- IPLZBDKITWXMGQ-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-ethyl-n-(2,2,2-trifluoroethyl)benzamide Chemical compound FC(F)(F)CN(CC)C(=O)C1=CC=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=C1 IPLZBDKITWXMGQ-UHFFFAOYSA-N 0.000 claims 1
- UNXXCZFYIHQYQB-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-ethyl-n-(2-methoxyethyl)benzamide Chemical compound COCCN(CC)C(=O)C1=CC=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=C1 UNXXCZFYIHQYQB-UHFFFAOYSA-N 0.000 claims 1
- BVEQNGQPIKHAKT-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-ethyl-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=CC=1C(=O)N(CC)CCN1CCOCC1 BVEQNGQPIKHAKT-UHFFFAOYSA-N 0.000 claims 1
- JGGSPPHCUXMITN-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-ethyl-n-(2-piperidin-1-ylethyl)benzamide;hydrochloride Chemical compound Cl.C=1C=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=CC=1C(=O)N(CC)CCN1CCCCC1 JGGSPPHCUXMITN-UHFFFAOYSA-N 0.000 claims 1
- KSMBBFQCJXVCDF-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-ethyl-n-(2-pyridin-4-ylethyl)benzamide;hydrochloride Chemical compound Cl.C=1C=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=CC=1C(=O)N(CC)CCC1=CC=NC=C1 KSMBBFQCJXVCDF-UHFFFAOYSA-N 0.000 claims 1
- ZRPQJRBWZGCIQH-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-ethyl-n-(3-pyridin-4-ylpropyl)benzamide Chemical compound C=1C=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=CC=1C(=O)N(CC)CCCC1=CC=NC=C1 ZRPQJRBWZGCIQH-UHFFFAOYSA-N 0.000 claims 1
- ZOININUGJFMRSB-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-ethyl-n-(pyridin-2-ylmethyl)benzamide Chemical compound C=1C=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=CC=1C(=O)N(CC)CC1=CC=CC=N1 ZOININUGJFMRSB-UHFFFAOYSA-N 0.000 claims 1
- UENRBNCNIZQNTR-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-ethyl-n-(pyridin-3-ylmethyl)benzamide Chemical compound C=1C=C(Cl)C(C2(C)C3=CC(Cl)=CC=C3N(CC=3C(=CC(OC)=CC=3)OC)C2=O)=CC=1C(=O)N(CC)CC1=CC=CN=C1 UENRBNCNIZQNTR-UHFFFAOYSA-N 0.000 claims 1
- XFBVSPHCGXWSSQ-UHFFFAOYSA-N 4-chloro-3-[5-chloro-1-[(2,4-dimethoxyphenyl)methyl]-3-methyl-2-oxoindol-3-yl]-n-methyl-n-(2,2,2-trifluoroethyl)benzamide Chemical compound COC1=CC(OC)=CC=C1CN1C2=CC=C(Cl)C=C2C(C)(C=2C(=CC=C(C=2)C(=O)N(C)CC(F)(F)F)Cl)C1=O XFBVSPHCGXWSSQ-UHFFFAOYSA-N 0.000 claims 1
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- IEGUGOVZQRGHJA-UHFFFAOYSA-N 5-chloro-3-[2-chloro-5-(2-morpholin-4-ylethoxymethyl)phenyl]-1-[(2,4-dimethoxyphenyl)methyl]-3-methylindol-2-one Chemical compound COC1=CC(OC)=CC=C1CN1C2=CC=C(Cl)C=C2C(C)(C=2C(=CC=C(COCCN3CCOCC3)C=2)Cl)C1=O IEGUGOVZQRGHJA-UHFFFAOYSA-N 0.000 claims 1
- FHESHZAZRRMDPJ-UHFFFAOYSA-N 5-chloro-3-[2-chloro-5-(4-hydroxypiperidine-1-carbonyl)phenyl]-1-[(2,4-dimethoxyphenyl)methyl]-3-methylindol-2-one Chemical compound COC1=CC(OC)=CC=C1CN1C2=CC=C(Cl)C=C2C(C)(C=2C(=CC=C(C=2)C(=O)N2CCC(O)CC2)Cl)C1=O FHESHZAZRRMDPJ-UHFFFAOYSA-N 0.000 claims 1
- AKIOBCMXZTXYMF-UHFFFAOYSA-N 5-chloro-3-[2-chloro-5-(morpholin-4-ylmethyl)phenyl]-1-[(2,4-dimethoxyphenyl)methyl]-3-methylindol-2-one Chemical compound COC1=CC(OC)=CC=C1CN1C2=CC=C(Cl)C=C2C(C)(C=2C(=CC=C(CN3CCOCC3)C=2)Cl)C1=O AKIOBCMXZTXYMF-UHFFFAOYSA-N 0.000 claims 1
- RHIUILGNWPYRRX-UHFFFAOYSA-N 5-chloro-3-[2-chloro-5-(piperidine-1-carbonyl)phenyl]-1-[(2,4-dimethoxyphenyl)methyl]-3-methylindol-2-one Chemical compound COC1=CC(OC)=CC=C1CN1C2=CC=C(Cl)C=C2C(C)(C=2C(=CC=C(C=2)C(=O)N2CCCCC2)Cl)C1=O RHIUILGNWPYRRX-UHFFFAOYSA-N 0.000 claims 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- Pain & Pain Management (AREA)
- Addiction (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
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 |
Publications (1)
Publication Number | Publication Date |
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ZA200207802B true ZA200207802B (en) | 2003-09-29 |
Family
ID=8848777
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Application Number | Title | Priority Date | Filing Date |
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ZA200207802A ZA200207802B (en) | 2000-04-03 | 2002-09-27 | Indolin-2-one derivatives, preparation and their use as ocytocin receptor ligands. |
Country Status (35)
Country | Link |
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US (2) | US20040059132A1 (is) |
EP (1) | EP1272468B1 (is) |
JP (1) | JP2003529586A (is) |
KR (1) | KR100765028B1 (is) |
CN (1) | CN1224614C (is) |
AR (1) | AR034547A1 (is) |
AT (1) | ATE282593T1 (is) |
AU (2) | AU2001246671B2 (is) |
BR (1) | BR0109814A (is) |
CA (1) | CA2404592A1 (is) |
CZ (1) | CZ20023297A3 (is) |
DE (1) | DE60107221T2 (is) |
DK (1) | DK1272468T3 (is) |
EA (1) | EA005093B1 (is) |
EE (1) | EE05002B1 (is) |
ES (1) | ES2232610T3 (is) |
FR (1) | FR2807038B1 (is) |
HK (1) | HK1050004A1 (is) |
HU (1) | HUP0303109A3 (is) |
IL (1) | IL152085A0 (is) |
IS (1) | IS2458B (is) |
ME (1) | MEP24308A (is) |
MX (1) | MXPA02009773A (is) |
NO (1) | NO324314B1 (is) |
NZ (1) | NZ521617A (is) |
PL (1) | PL358222A1 (is) |
PT (1) | PT1272468E (is) |
SI (1) | SI1272468T1 (is) |
SK (1) | SK14272002A3 (is) |
TR (1) | TR200202288T2 (is) |
TW (1) | TWI225860B (is) |
UA (1) | UA73163C2 (is) |
WO (1) | WO2001074775A1 (is) |
YU (1) | YU80902A (is) |
ZA (1) | ZA200207802B (is) |
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 |
-
2000
- 2000-04-03 FR FR0004193A patent/FR2807038B1/fr not_active Expired - Fee Related
-
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/xx 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
-
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
-
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
-
2007
- 2007-05-03 US US11/744,003 patent/US20070203184A1/en not_active Abandoned
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