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) | EP2255801B1 (https=) |
| JP (1) | JP5116201B2 (https=) |
| CN (1) | CN1325497C (https=) |
| AT (4) | ATE357913T1 (https=) |
| AU (2) | AU782409B2 (https=) |
| CA (1) | CA2392081C (https=) |
| CY (2) | CY1107610T1 (https=) |
| DE (1) | DE60034139T2 (https=) |
| DK (2) | DK2263669T3 (https=) |
| ES (4) | ES2380574T3 (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=) |
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|---|---|---|---|---|
| US6429221B1 (en) | 1994-12-30 | 2002-08-06 | Celgene Corporation | Substituted imides |
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| CN110003084B (zh) * | 2019-03-15 | 2022-08-02 | 华南师范大学 | 一种同时具有力致发光和聚集诱导发光特性的有机圆偏振发光材料及其制备方法与应用 |
| CN111170925B (zh) * | 2020-01-09 | 2023-01-17 | 常州大学 | 作为pde2/4双重抑制剂的邻苯二甲酰亚胺类化合物及其制备方法 |
| TW202237580A (zh) * | 2020-12-14 | 2022-10-01 | 美商拜歐斯瑞克斯公司 | Pde4降解劑、醫藥組合物及治療應用 |
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-
2000
- 2000-11-08 US US09/708,199 patent/US6667316B1/en not_active Expired - Lifetime
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- 2000-11-09 CA CA002392081A patent/CA2392081C/en not_active Expired - Fee Related
- 2000-11-09 PT PT10176420T patent/PT2263669E/pt unknown
- 2000-11-09 ES ES10176420T patent/ES2380574T3/es not_active Expired - Lifetime
- 2000-11-09 AT AT00977095T patent/ATE357913T1/de active
- 2000-11-09 EP EP10176420A patent/EP2263669B1/en not_active Expired - Lifetime
- 2000-11-09 AT AT10176420T patent/ATE544452T1/de active
- 2000-11-09 SI SI200030951T patent/SI1228071T1/sl unknown
- 2000-11-09 WO PCT/US2000/030770 patent/WO2001034606A1/en not_active Ceased
- 2000-11-09 CN CNB00818254XA patent/CN1325497C/zh not_active Expired - Fee Related
- 2000-11-09 JP JP2001536553A patent/JP5116201B2/ja not_active Expired - Fee Related
- 2000-11-09 ES ES00977095T patent/ES2282147T3/es not_active Expired - Lifetime
- 2000-11-09 NZ NZ519459A patent/NZ519459A/en not_active IP Right Cessation
- 2000-11-09 DK DK10176420.7T patent/DK2263669T3/da active
- 2000-11-09 AU AU14780/01A patent/AU782409B2/en not_active Ceased
- 2000-11-09 AT AT10176390T patent/ATE544451T1/de active
- 2000-11-09 ES ES10176390T patent/ES2381174T3/es not_active Expired - Lifetime
- 2000-11-09 ES ES06009632T patent/ES2363933T3/es not_active Expired - Lifetime
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- 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 HK HK03100819.6A patent/HK1049158A1/zh unknown
- 2000-11-09 DK DK00977095T patent/DK1228071T3/da active
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2002
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- 2002-05-10 FI FI20020892A patent/FI119931B/fi not_active IP Right Cessation
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