JP2011526610A5 - - Google Patents
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- Publication number
- JP2011526610A5 JP2011526610A5 JP2011515526A JP2011515526A JP2011526610A5 JP 2011526610 A5 JP2011526610 A5 JP 2011526610A5 JP 2011515526 A JP2011515526 A JP 2011515526A JP 2011515526 A JP2011515526 A JP 2011515526A JP 2011526610 A5 JP2011526610 A5 JP 2011526610A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydropyrrolo
- carbazole
- optionally substituted
- group
- carbaldehyde
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 13
- -1 sulfophenyl group Chemical group 0.000 claims 11
- 150000002825 nitriles Chemical class 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 3
- VWNCOFUKBTYAON-UHFFFAOYSA-N 1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound C12=CC=CC=C2NC2=C1C=CC1=C2NC=C1C=O VWNCOFUKBTYAON-UHFFFAOYSA-N 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000001118 alkylidene group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- BPHGZSRGCZJRGO-UHFFFAOYSA-N 1,10-dihydropyrrolo[2,3-a]carbazole Chemical compound C1=CC=C2NC3=C(NC=C4)C4=CC=C3C2=C1 BPHGZSRGCZJRGO-UHFFFAOYSA-N 0.000 claims 2
- IPZURMNMOLTFSU-UHFFFAOYSA-N 1-(1,10-dihydropyrrolo[2,3-a]carbazol-3-yl)-2,2,2-trifluoroethanone Chemical compound C12=CC=CC=C2NC2=C1C=CC1=C2NC=C1C(=O)C(F)(F)F IPZURMNMOLTFSU-UHFFFAOYSA-N 0.000 claims 2
- IYKWFKKDLTZONH-UHFFFAOYSA-N 6-bromo-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound C1=2C(Br)=CC=CC=2NC2=C1C=CC1=C2NC=C1C=O IYKWFKKDLTZONH-UHFFFAOYSA-N 0.000 claims 2
- BFWHRHJPPAUSLJ-UHFFFAOYSA-N 7-(2,4-difluorophenyl)-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound FC1=CC(F)=CC=C1C1=CC=C(NC=2C=3NC=C(C=O)C=3C=CC=22)C2=C1 BFWHRHJPPAUSLJ-UHFFFAOYSA-N 0.000 claims 2
- JRPUZUBQJFQSQO-UHFFFAOYSA-N 7-bromo-1,10-dihydropyrrolo[2,3-a]carbazole Chemical compound C12=CC(Br)=CC=C2NC2=C1C=CC1=C2NC=C1 JRPUZUBQJFQSQO-UHFFFAOYSA-N 0.000 claims 2
- KUIXBLRMWNOGNN-UHFFFAOYSA-N 7-bromo-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound C12=CC(Br)=CC=C2NC2=C1C=CC1=C2NC=C1C=O KUIXBLRMWNOGNN-UHFFFAOYSA-N 0.000 claims 2
- ZRRGYYZOLYHGAW-UHFFFAOYSA-N 9-ethyl-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound CCC1=CC=CC2=C1NC1=C2C=CC2=C1NC=C2C=O ZRRGYYZOLYHGAW-UHFFFAOYSA-N 0.000 claims 2
- VIRITAWLUCSUIP-UHFFFAOYSA-N 9-fluoro-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound FC1=CC=CC2=C1NC1=C2C=CC2=C1NC=C2C=O VIRITAWLUCSUIP-UHFFFAOYSA-N 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical group NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 2
- 229940067157 phenylhydrazine Drugs 0.000 claims 2
- MXZKCOUOYWSEKW-UHFFFAOYSA-N 1,10-dihydropyrrolo[2,3-a]carbazole-3-carboxamide Chemical compound C12=CC=CC=C2NC2=C1C=CC1=C2NC=C1C(=O)N MXZKCOUOYWSEKW-UHFFFAOYSA-N 0.000 claims 1
- OWWVHLWJKVVCTP-UHFFFAOYSA-N 1-(benzenesulfonyl)-5,6-dihydro-4h-indol-7-one Chemical group C1=2C(=O)CCCC=2C=CN1S(=O)(=O)C1=CC=CC=C1 OWWVHLWJKVVCTP-UHFFFAOYSA-N 0.000 claims 1
- PZBQSOWJBOUUIV-UHFFFAOYSA-N 6,8-dichloro-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound C=1C(Cl)=CC(Cl)=C2C=1NC1=C2C=CC2=C1NC=C2C=O PZBQSOWJBOUUIV-UHFFFAOYSA-N 0.000 claims 1
- MWJXEWYSFDLQRR-UHFFFAOYSA-N 7-fluoro-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound C12=CC(F)=CC=C2NC2=C1C=CC1=C2NC=C1C=O MWJXEWYSFDLQRR-UHFFFAOYSA-N 0.000 claims 1
- OGEKUJPOQMHESI-UHFFFAOYSA-N 8-methyl-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical group C=1C(C)=CC=C2C=1NC1=C2C=CC2=C1NC=C2C=O OGEKUJPOQMHESI-UHFFFAOYSA-N 0.000 claims 1
- CMILZUZLXJQSGJ-UHFFFAOYSA-N 9-bromo-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde Chemical compound BrC1=CC=CC2=C1NC1=C2C=CC2=C1NC=C2C=O CMILZUZLXJQSGJ-UHFFFAOYSA-N 0.000 claims 1
- DAQVEWBELJFYBE-UHFFFAOYSA-N 9h-carbazole-3-carboxamide Chemical compound C1=CC=C2C3=CC(C(=O)N)=CC=C3NC2=C1 DAQVEWBELJFYBE-UHFFFAOYSA-N 0.000 claims 1
- 101100297652 Coturnix japonica PIM3 gene Proteins 0.000 claims 1
- 101001001649 Danio rerio Serine/threonine-protein kinase pim-2 Proteins 0.000 claims 1
- VLDUOBZGODDWME-UHFFFAOYSA-N FC=1C=C2C3=CC=C4C(=C3NC2=CC1)NC=C4C=O.BrC=4C=CC=C1C2=CC=C3C(=C2NC41)NC=C3C=O Chemical compound FC=1C=C2C3=CC=C4C(=C3NC2=CC1)NC=C4C=O.BrC=4C=CC=C1C2=CC=C3C(=C2NC41)NC=C3C=O VLDUOBZGODDWME-UHFFFAOYSA-N 0.000 claims 1
- 101100297651 Mus musculus Pim2 gene Proteins 0.000 claims 1
- PCLHDMUPSIFJKW-UHFFFAOYSA-L [Cl-].OCC[N+](C)(C)C.[Cl-].[Zn+] Chemical compound [Cl-].OCC[N+](C)(C)C.[Cl-].[Zn+] PCLHDMUPSIFJKW-UHFFFAOYSA-L 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000002608 ionic liquid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0803752A FR2933409B1 (fr) | 2008-07-03 | 2008-07-03 | NOUVEAUX PYRROLO °2,3-a! CARBAZOLES ET LEUR UTILISATION COMME INHIBITEURS DES KINASES PIM |
| FR0803752 | 2008-07-03 | ||
| PCT/FR2009/000788 WO2010000978A1 (fr) | 2008-07-03 | 2009-06-25 | NOUVEAUX PYRROLO [2,3-a] CARBAZOLES ET LEUR UTILISATION COMME INHIBITEURS DES KINASES PIM |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011526610A JP2011526610A (ja) | 2011-10-13 |
| JP2011526610A5 true JP2011526610A5 (https=) | 2012-08-02 |
| JP5663476B2 JP5663476B2 (ja) | 2015-02-04 |
Family
ID=40328682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011515526A Expired - Fee Related JP5663476B2 (ja) | 2008-07-03 | 2009-06-25 | 新規ピロロ［２，３−ａ］カルバゾールおよびＰＩＭキナーゼ阻害剤としてのそれらの使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8481586B2 (https=) |
| EP (1) | EP2326649B1 (https=) |
| JP (1) | JP5663476B2 (https=) |
| AT (1) | ATE551344T1 (https=) |
| CA (1) | CA2729690A1 (https=) |
| FR (1) | FR2933409B1 (https=) |
| WO (1) | WO2010000978A1 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2455382B1 (en) | 2005-12-13 | 2016-10-26 | Incyte Holdings Corporation | Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors |
| EP3070090B1 (en) | 2007-06-13 | 2018-12-12 | Incyte Holdings Corporation | Use of salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h- pyrazol-1-yl)-3- cyclopentylpropanenitrile |
| SG176111A1 (en) | 2009-05-22 | 2011-12-29 | Incyte Corp | 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]octane- or heptane-nitrile as jak inhibitors |
| JP5775070B2 (ja) | 2009-05-22 | 2015-09-09 | インサイト・コーポレイションＩｎｃｙｔｅ Ｃｏｒｐｏｒａｔｉｏｎ | ヤヌスキナーゼ阻害剤としてのピラゾール−４−イル−ピロロ［２，３−ｄ］ピリミジンおよびピロール−３−イル−ピロロ［２，３−ｄ］ピリミジンのＮ−（ヘテロ）アリール−ピロリジン誘導体 |
| AR078012A1 (es) | 2009-09-01 | 2011-10-05 | Incyte Corp | Derivados heterociclicos de las pirazol-4-il- pirrolo (2,3-d) pirimidinas como inhibidores de la quinasa janus |
| PT3354652T (pt) | 2010-03-10 | 2020-07-20 | Incyte Holdings Corp | Derivados de piperidin-4-ilazetidina como inibidores de jak1 |
| RS54824B1 (sr) | 2010-05-21 | 2016-10-31 | Incyte Holdings Corp | Topikalna formulacija za inhibiciju jak-a |
| CA2818542A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| WO2012068440A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as jak inhibitors |
| MY165963A (en) | 2011-06-20 | 2018-05-18 | Incyte Holdings Corp | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as jak inhibitors |
| EP2734205B1 (en) | 2011-07-21 | 2018-03-21 | Tolero Pharmaceuticals, Inc. | Heterocyclic protein kinase inhibitors |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| KR101488565B1 (ko) | 2011-12-07 | 2015-02-03 | 주식회사 두산 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
| TW201406761A (zh) | 2012-05-18 | 2014-02-16 | Incyte Corp | 做爲ｊａｋ抑制劑之哌啶基環丁基取代之吡咯并吡啶及吡咯并嘧啶衍生物 |
| KR101452579B1 (ko) | 2012-08-17 | 2014-10-21 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| KR101537436B1 (ko) * | 2012-08-17 | 2015-07-17 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| CN113384546A (zh) | 2012-11-15 | 2021-09-14 | 因赛特公司 | 鲁索利替尼的缓释剂型 |
| JP6437452B2 (ja) | 2013-01-14 | 2018-12-12 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉｍキナーゼ阻害剤として有用な二環式芳香族カルボキサミド化合物 |
| RS60244B1 (sr) | 2013-01-15 | 2020-06-30 | Incyte Holdings Corp | Jedinjenja tiazolkarboksamida i piridinkarboksamida korisna kao inhibitori pim kinaze |
| FR3001219A1 (fr) * | 2013-01-22 | 2014-07-25 | Centre Nat Rech Scient | Inhibiteurs de kinases |
| WO2014138168A1 (en) | 2013-03-06 | 2014-09-12 | Incyte Corporation | Processes and intermediates for making a jak inhibitor |
| SG10201801069QA (en) | 2013-08-07 | 2018-03-28 | Incyte Corp | Sustained release dosage forms for a jak1 inhibitor |
| CN105658653A (zh) | 2013-08-23 | 2016-06-08 | 因赛特公司 | 可用作pim激酶抑制剂的呋喃并-和噻吩并-吡啶甲酰胺化合物 |
| US9498467B2 (en) | 2014-05-30 | 2016-11-22 | Incyte Corporation | Treatment of chronic neutrophilic leukemia (CNL) and atypical chronic myeloid leukemia (aCML) by inhibitors of JAK1 |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| WO2016010897A1 (en) | 2014-07-14 | 2016-01-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as pim kinase inhibitors |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| TWI734699B (zh) | 2015-09-09 | 2021-08-01 | 美商英塞特公司 | Ｐｉｍ激酶抑制劑之鹽 |
| US9920032B2 (en) | 2015-10-02 | 2018-03-20 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| AR113922A1 (es) | 2017-12-08 | 2020-07-01 | Incyte Corp | Terapia de combinación de dosis baja para el tratamiento de neoplasias mieloproliferativas |
| EA202091830A1 (ru) | 2018-01-30 | 2020-12-29 | Инсайт Корпорейшн | Способы и промежуточные соединения для получения ингибитора jak |
| MD3773593T2 (ro) | 2018-03-30 | 2024-10-31 | Incyte Corp | Tratament hidradenitei supurative utilizând inhibitori ai JAK |
| CN117838695A (zh) | 2018-04-13 | 2024-04-09 | 住友制药肿瘤公司 | 用于治疗骨髓增殖性肿瘤和与癌症相关的纤维化的pim激酶抑制剂 |
| NZ778055A (en) | 2019-02-12 | 2025-11-28 | Sumitomo Pharma America Inc | Formulations comprising heterocyclic protein kinase inhibitors |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| EP4611753A1 (en) | 2022-10-31 | 2025-09-10 | Sumitomo Pharma America, Inc. | Pim1 inhibitor for treating myeloproliferative neoplasms |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101316847A (zh) * | 2005-10-06 | 2008-12-03 | 先灵公司 | 用作蛋白激酶抑制剂的吡唑并(1,5a)嘧啶化合物 |
| TW200804386A (en) * | 2005-11-10 | 2008-01-16 | Schering Corp | Imidazopyrazines as protein kinase inhibitors |
-
2008
- 2008-07-03 FR FR0803752A patent/FR2933409B1/fr not_active Expired - Fee Related
-
2009
- 2009-06-25 US US13/002,423 patent/US8481586B2/en not_active Expired - Fee Related
- 2009-06-25 EP EP09772661A patent/EP2326649B1/fr not_active Not-in-force
- 2009-06-25 CA CA2729690A patent/CA2729690A1/fr not_active Abandoned
- 2009-06-25 AT AT09772661T patent/ATE551344T1/de active
- 2009-06-25 JP JP2011515526A patent/JP5663476B2/ja not_active Expired - Fee Related
- 2009-06-25 WO PCT/FR2009/000788 patent/WO2010000978A1/fr not_active Ceased
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