JP2004500346A5 - - Google Patents
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- JP2004500346A5 JP2004500346A5 JP2001536553A JP2001536553A JP2004500346A5 JP 2004500346 A5 JP2004500346 A5 JP 2004500346A5 JP 2001536553 A JP2001536553 A JP 2001536553A JP 2001536553 A JP2001536553 A JP 2001536553A JP 2004500346 A5 JP2004500346 A5 JP 2004500346A5
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- ethoxy
- methoxyphenyl
- alkyl
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000004432 carbon atom Chemical group C* 0.000 claims 85
- 150000001875 compounds Chemical class 0.000 claims 44
- 125000000217 alkyl group Chemical group 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 29
- 239000001257 hydrogen Substances 0.000 claims 29
- -1 N- substituted carbamoyl Chemical group 0.000 claims 22
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000004663 dialkyl amino group Chemical group 0.000 claims 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical group 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 125000001589 carboacyl group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 6
- JTAPIZGDGUNKHP-UHFFFAOYSA-N 3-[4-[[2-(dimethylamino)acetyl]amino]-1,3-dioxoisoindol-2-yl]-3-(3-ethoxy-4-methoxyphenyl)-n,n-dimethylpropanamide;hydrochloride Chemical compound Cl.C1=C(OC)C(OCC)=CC(C(CC(=O)N(C)C)N2C(C3=C(NC(=O)CN(C)C)C=CC=C3C2=O)=O)=C1 JTAPIZGDGUNKHP-UHFFFAOYSA-N 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- CZVNIGALSIBARE-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2=O)=O)=C1 CZVNIGALSIBARE-UHFFFAOYSA-N 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- FXSJRFSDOVESKN-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-pyrrol-1-ylisoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(C=CC=C3C2=O)N2C=CC=C2)=O)=C1 FXSJRFSDOVESKN-UHFFFAOYSA-N 0.000 claims 3
- NAKSEFFBNWKUJH-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]-4-(1h-pyrrol-2-ylmethyl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CC(C)=O)N2C(C3=C(CC=4NC=CC=4)C=CC=C3C2=O)=O)=C1 NAKSEFFBNWKUJH-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001118 alkylidene group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- QDZOBXFRIVOQBR-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 QDZOBXFRIVOQBR-UHFFFAOYSA-N 0.000 claims 3
- HHSCRXUCPLPVQX-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(C)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 HHSCRXUCPLPVQX-UHFFFAOYSA-N 0.000 claims 3
- XCCGODHJXOPFSU-UHFFFAOYSA-N n-[2-[3-(dimethylamino)-1-(3-ethoxy-4-methoxyphenyl)-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)N(C)C)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 XCCGODHJXOPFSU-UHFFFAOYSA-N 0.000 claims 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- VEGYJRRNNSDCEL-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]-4-pyrrol-1-ylisoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CC(C)=O)N2C(C3=C(C=CC=C3C2=O)N2C=CC=C2)=O)=C1 VEGYJRRNNSDCEL-UHFFFAOYSA-N 0.000 claims 2
- PAOZAMACNXMCIB-UHFFFAOYSA-N N-[2-[1-(3,4-dimethoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CS(C)(=O)=O)N1C(=O)C2=C(NC(=O)C3CC3)C=CC=C2C1=O PAOZAMACNXMCIB-UHFFFAOYSA-N 0.000 claims 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- MVFSISZBKOLEKN-UHFFFAOYSA-N n-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-oxobutyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound COC1=CC=C(C(CC(C)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)C=C1OC1CCCC1 MVFSISZBKOLEKN-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- HPNGOUOSHMENJP-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-(1h-pyrrol-2-ylmethyl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(CC=4NC=CC=4)C=CC=C3C2=O)=O)=C1 HPNGOUOSHMENJP-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims 1
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003972 antineoplastic antibiotic Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000007972 injectable composition Substances 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 125000002345 steroid group Chemical group 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16516899P | 1999-11-12 | 1999-11-12 | |
| US60/165,168 | 1999-11-12 | ||
| US59034400A | 2000-06-08 | 2000-06-08 | |
| US09/590,344 | 2000-06-08 | ||
| US09/708,199 | 2000-11-08 | ||
| US09/708,199 US6667316B1 (en) | 1999-11-12 | 2000-11-08 | Pharmaceutically active isoindoline derivatives |
| PCT/US2000/030770 WO2001034606A1 (en) | 1999-11-12 | 2000-11-09 | Pharmaceutically active isoindoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004500346A JP2004500346A (ja) | 2004-01-08 |
| JP2004500346A5 true JP2004500346A5 (https=) | 2005-01-06 |
| JP5116201B2 JP5116201B2 (ja) | 2013-01-09 |
Family
ID=27389110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001536553A Expired - Fee Related JP5116201B2 (ja) | 1999-11-12 | 2000-11-09 | 薬剤活性のあるイソインドリン誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6667316B1 (https=) |
| EP (4) | EP1228071B8 (https=) |
| JP (1) | JP5116201B2 (https=) |
| CN (1) | CN1325497C (https=) |
| AT (4) | ATE506058T1 (https=) |
| AU (2) | AU782409B2 (https=) |
| CA (1) | CA2392081C (https=) |
| CY (2) | CY1107610T1 (https=) |
| DE (1) | DE60034139T2 (https=) |
| DK (2) | DK1228071T3 (https=) |
| ES (4) | ES2282147T3 (https=) |
| FI (1) | FI119931B (https=) |
| HK (1) | HK1049158A1 (https=) |
| MX (1) | MXPA02004793A (https=) |
| NO (2) | NO323633B1 (https=) |
| NZ (1) | NZ519459A (https=) |
| PT (2) | PT1228071E (https=) |
| SI (1) | SI1228071T1 (https=) |
| WO (1) | WO2001034606A1 (https=) |
Families Citing this family (75)
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|---|---|---|---|---|
| US6429221B1 (en) | 1994-12-30 | 2002-08-06 | Celgene Corporation | Substituted imides |
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-
2000
- 2000-11-08 US US09/708,199 patent/US6667316B1/en not_active Expired - Lifetime
- 2000-11-09 CN CNB00818254XA patent/CN1325497C/zh not_active Expired - Fee Related
- 2000-11-09 ES ES00977095T patent/ES2282147T3/es not_active Expired - Lifetime
- 2000-11-09 AT AT06009632T patent/ATE506058T1/de not_active IP Right Cessation
- 2000-11-09 EP EP00977095A patent/EP1228071B8/en not_active Expired - Lifetime
- 2000-11-09 MX MXPA02004793A patent/MXPA02004793A/es active IP Right Grant
- 2000-11-09 ES ES06009632T patent/ES2363933T3/es not_active Expired - Lifetime
- 2000-11-09 ES ES10176420T patent/ES2380574T3/es not_active Expired - Lifetime
- 2000-11-09 EP EP10176420A patent/EP2263669B1/en not_active Expired - Lifetime
- 2000-11-09 DK DK00977095T patent/DK1228071T3/da active
- 2000-11-09 CA CA002392081A patent/CA2392081C/en not_active Expired - Fee Related
- 2000-11-09 NZ NZ519459A patent/NZ519459A/en not_active IP Right Cessation
- 2000-11-09 JP JP2001536553A patent/JP5116201B2/ja not_active Expired - Fee Related
- 2000-11-09 DE DE60034139T patent/DE60034139T2/de not_active Expired - Lifetime
- 2000-11-09 AU AU14780/01A patent/AU782409B2/en not_active Ceased
- 2000-11-09 DK DK10176420.7T patent/DK2263669T3/da active
- 2000-11-09 AT AT10176390T patent/ATE544451T1/de active
- 2000-11-09 AT AT00977095T patent/ATE357913T1/de active
- 2000-11-09 EP EP10176390A patent/EP2255801B1/en not_active Expired - Lifetime
- 2000-11-09 SI SI200030951T patent/SI1228071T1/sl unknown
- 2000-11-09 PT PT00977095T patent/PT1228071E/pt unknown
- 2000-11-09 ES ES10176390T patent/ES2381174T3/es not_active Expired - Lifetime
- 2000-11-09 PT PT10176420T patent/PT2263669E/pt unknown
- 2000-11-09 HK HK03100819.6A patent/HK1049158A1/zh unknown
- 2000-11-09 AT AT10176420T patent/ATE544452T1/de active
- 2000-11-09 WO PCT/US2000/030770 patent/WO2001034606A1/en not_active Ceased
- 2000-11-09 EP EP06009632A patent/EP1698334B1/en not_active Expired - Lifetime
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2002
- 2002-05-08 NO NO20022223A patent/NO323633B1/no not_active IP Right Cessation
- 2002-05-10 FI FI20020892A patent/FI119931B/fi not_active IP Right Cessation
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2005
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