JP2005508336A5 - - Google Patents
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- Publication number
- JP2005508336A5 JP2005508336A5 JP2003530690A JP2003530690A JP2005508336A5 JP 2005508336 A5 JP2005508336 A5 JP 2005508336A5 JP 2003530690 A JP2003530690 A JP 2003530690A JP 2003530690 A JP2003530690 A JP 2003530690A JP 2005508336 A5 JP2005508336 A5 JP 2005508336A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidinyl
- piperazinyl
- alkyl
- morpholinyl
- pyridinyl
- 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.)
- Pending
Links
- -1 3-fluoropyrrolidinyl Chemical group 0.000 claims description 133
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 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 13
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 150000003568 thioethers Chemical class 0.000 claims description 6
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- ZCCPVTVGEQLONB-UHFFFAOYSA-N 1-(1,3-dioxolan-2-yl)-n-methylmethanamine Chemical compound CNCC1OCCO1 ZCCPVTVGEQLONB-UHFFFAOYSA-N 0.000 claims description 4
- QAFODUGVXFNLBE-UHFFFAOYSA-N 1-methoxybutan-2-amine Chemical compound CCC(N)COC QAFODUGVXFNLBE-UHFFFAOYSA-N 0.000 claims description 4
- ZUUQKDDUUOFCNP-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)-n-methylethanamine Chemical compound CNCCC1OCCO1 ZUUQKDDUUOFCNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 4
- RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 claims description 3
- IPBPLHNLRKRLPJ-UHFFFAOYSA-N oxan-4-ylmethanamine Chemical compound NCC1CCOCC1 IPBPLHNLRKRLPJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims 14
- 125000005647 linker group Chemical group 0.000 claims 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 230000002062 proliferating effect Effects 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 206010016654 Fibrosis Diseases 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 208000030159 metabolic disease Diseases 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 230000004761 fibrosis Effects 0.000 claims 4
- 210000003584 mesangial cell Anatomy 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 230000002792 vascular Effects 0.000 claims 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 206010064930 age-related macular degeneration Diseases 0.000 claims 3
- 125000006309 butyl amino group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 208000002780 macular degeneration Diseases 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010063209 Chronic allograft nephropathy Diseases 0.000 claims 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 2
- 208000034841 Thrombotic Microangiopathies Diseases 0.000 claims 2
- 208000031737 Tissue Adhesions Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000007882 cirrhosis Effects 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 201000009925 nephrosclerosis Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32581901P | 2001-09-27 | 2001-09-27 | |
| US32581501P | 2001-09-27 | 2001-09-27 | |
| PCT/US2002/030882 WO2003027102A1 (en) | 2001-09-27 | 2002-09-27 | 3-(arylamino)methylene-1, 3-dihydro-2h-indol-2-ones as kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010013326A Division JP2010116411A (ja) | 2001-09-27 | 2010-01-25 | キナーゼ阻害物質としての３−（アリールアミノ）メチレン−１，３−ジヒドロ−２ｈ−インドール−２−オン類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005508336A JP2005508336A (ja) | 2005-03-31 |
| JP2005508336A5 true JP2005508336A5 (enExample) | 2006-01-12 |
Family
ID=26985125
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003530690A Pending JP2005508336A (ja) | 2001-09-27 | 2002-09-27 | キナーゼ阻害物質としての３−（アリールアミノ）メチレン−１，３−ジヒドロ−２ｈ−インドール−２−オン類 |
| JP2010013326A Pending JP2010116411A (ja) | 2001-09-27 | 2010-01-25 | キナーゼ阻害物質としての３−（アリールアミノ）メチレン−１，３−ジヒドロ−２ｈ−インドール−２−オン類 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010013326A Pending JP2010116411A (ja) | 2001-09-27 | 2010-01-25 | キナーゼ阻害物質としての３−（アリールアミノ）メチレン−１，３−ジヒドロ−２ｈ−インドール−２−オン類 |
Country Status (6)
| Country | Link |
|---|---|
| US (7) | US6765012B2 (enExample) |
| EP (1) | EP1430048A1 (enExample) |
| JP (2) | JP2005508336A (enExample) |
| AU (1) | AU2002341881B2 (enExample) |
| CA (1) | CA2461812C (enExample) |
| WO (1) | WO2003027102A1 (enExample) |
Families Citing this family (80)
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| US7169936B2 (en) | 2002-07-23 | 2007-01-30 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Indolinone derivatives substituted in the 6-position, their preparation and their use as medicaments |
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| CA2994925C (en) | 2015-08-20 | 2023-08-29 | Eisai R&D Management Co., Ltd. | Tumor therapeutic agent |
| US12303505B2 (en) | 2017-02-08 | 2025-05-20 | Eisai R&D Management Co., Ltd. | Tumor-treating pharmaceutical composition |
| CN108822017A (zh) * | 2017-04-11 | 2018-11-16 | 中国医学科学院药物研究所 | 新型吲哚酮化合物及其制法和药物用途 |
| BR112019023064A2 (pt) | 2017-05-16 | 2020-06-09 | Eisai R&D Man Co Ltd | tratamento de carcinoma hepatocelular |
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| CN111285872B (zh) * | 2018-12-06 | 2022-05-17 | 北京志健金瑞生物医药科技有限公司 | 吲哚-2-酮衍生物及其制备方法与用途 |
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| US5217999A (en) * | 1987-12-24 | 1993-06-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Styryl compounds which inhibit EGF receptor protein tyrosine kinase |
| AT389506B (de) * | 1988-08-04 | 1989-12-27 | Voest Alpine Maschinenbau | Verfahren und vorrichtung zum graphitieren von kohlenstoffkoerpern |
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-
2002
- 2002-09-27 AU AU2002341881A patent/AU2002341881B2/en not_active Ceased
- 2002-09-27 CA CA2461812A patent/CA2461812C/en not_active Expired - Fee Related
- 2002-09-27 EP EP02776036A patent/EP1430048A1/en not_active Withdrawn
- 2002-09-27 US US10/256,879 patent/US6765012B2/en not_active Expired - Fee Related
- 2002-09-27 US US10/259,703 patent/US20030225152A1/en not_active Abandoned
- 2002-09-27 WO PCT/US2002/030882 patent/WO2003027102A1/en not_active Ceased
- 2002-09-27 JP JP2003530690A patent/JP2005508336A/ja active Pending
-
2004
- 2004-02-20 US US10/783,325 patent/US7015220B2/en not_active Expired - Lifetime
- 2004-07-06 US US10/886,213 patent/US7098236B2/en not_active Expired - Lifetime
-
2005
- 2005-09-16 US US11/228,780 patent/US20060025413A1/en not_active Abandoned
- 2005-11-15 US US11/274,681 patent/US7414054B2/en not_active Expired - Lifetime
-
2006
- 2006-03-31 US US11/396,036 patent/US20060194863A1/en not_active Abandoned
-
2010
- 2010-01-25 JP JP2010013326A patent/JP2010116411A/ja active Pending
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