JP2014503521A5 - - Google Patents
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- Publication number
- JP2014503521A5 JP2014503521A5 JP2013543704A JP2013543704A JP2014503521A5 JP 2014503521 A5 JP2014503521 A5 JP 2014503521A5 JP 2013543704 A JP2013543704 A JP 2013543704A JP 2013543704 A JP2013543704 A JP 2013543704A JP 2014503521 A5 JP2014503521 A5 JP 2014503521A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- amino
- pyrazin
- cyclopropyl
- benzamide
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- -1 2-hydroxy-2-methylpropyl Chemical group 0.000 claims 24
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 23
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- YUHKXKGPLTYXSO-UHFFFAOYSA-N n-cyclopropyl-4-[8-(thiophen-2-ylmethylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1C=C(C=2N3C=CN=C(NCC=4SC=CC=4)C3=NC=2)C=CC=1C(=O)NC1CC1 YUHKXKGPLTYXSO-UHFFFAOYSA-N 0.000 claims 2
- 125000006308 propyl amino group Chemical group 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- HIYJEHMJWYCULU-UHFFFAOYSA-N 2-chloro-4-[8-[(5-chlorothiophen-2-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound S1C(Cl)=CC=C1CNC1=NC=CN2C1=NC=C2C(C=C1Cl)=CC=C1C(=O)NC1CC1 HIYJEHMJWYCULU-UHFFFAOYSA-N 0.000 claims 1
- DUVOMWZVHYOJEE-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-(ethylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC)=NC=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 DUVOMWZVHYOJEE-UHFFFAOYSA-N 0.000 claims 1
- MCGKKBSOGWKPMH-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(O)C(F)(F)F)=NC=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 MCGKKBSOGWKPMH-UHFFFAOYSA-N 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims 1
- UFDGHUSWKBEXSW-UHFFFAOYSA-N 4-[8-(2-acetamidoethylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCCNC(=O)C)=NC=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 UFDGHUSWKBEXSW-UHFFFAOYSA-N 0.000 claims 1
- MJCRQRQSDZYDPF-UHFFFAOYSA-N 4-[8-(2-cyanoethylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCCC#N)C3=NC=2)=CC=C1C(=O)NC1CC1 MJCRQRQSDZYDPF-UHFFFAOYSA-N 0.000 claims 1
- SKRFUWYONYPJMR-UHFFFAOYSA-N 4-[8-(butylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCCCC)=NC=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 SKRFUWYONYPJMR-UHFFFAOYSA-N 0.000 claims 1
- UODNTVGGJJCGDE-UHFFFAOYSA-N 4-[8-[(5-chlorothiophen-2-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCC=4SC(Cl)=CC=4)C3=NC=2)=CC=C1C(=O)NC1CC1 UODNTVGGJJCGDE-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- RZOSGONDPNDPKL-UHFFFAOYSA-N n-cyclopropyl-2-hydroxy-4-[8-(propylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCC)=NC=CN2C=1C(C=C1O)=CC=C1C(=O)NC1CC1 RZOSGONDPNDPKL-UHFFFAOYSA-N 0.000 claims 1
- FCLYKQGCTKSYSA-UHFFFAOYSA-N n-cyclopropyl-2-hydroxy-4-[8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(O)C(F)(F)F)=NC=CN2C=1C(C=C1O)=CC=C1C(=O)NC1CC1 FCLYKQGCTKSYSA-UHFFFAOYSA-N 0.000 claims 1
- DLCRZBSBOCYDKN-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(3-methylsulfonylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCCCS(C)(=O)=O)C3=NC=2)=CC=C1C(=O)NC1CC1 DLCRZBSBOCYDKN-UHFFFAOYSA-N 0.000 claims 1
- YLNSOVZKDITAJC-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(propylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCC)=NC=CN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 YLNSOVZKDITAJC-UHFFFAOYSA-N 0.000 claims 1
- ROKREJRMVRGYEL-UHFFFAOYSA-N n-cyclopropyl-3-methyl-4-[8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC=CN2C=1C(C(=C1)C)=CC=C1C(=O)NC1CC1 ROKREJRMVRGYEL-UHFFFAOYSA-N 0.000 claims 1
- QTOFVYOMOKYCEQ-UHFFFAOYSA-N n-cyclopropyl-4-[8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 QTOFVYOMOKYCEQ-UHFFFAOYSA-N 0.000 claims 1
- VKMQPNMNSDSJRV-UHFFFAOYSA-N n-cyclopropyl-4-[8-(3-hydroxypropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCCCO)C3=NC=2)=CC=C1C(=O)NC1CC1 VKMQPNMNSDSJRV-UHFFFAOYSA-N 0.000 claims 1
- KYPBWUWXWHYHAG-UHFFFAOYSA-N n-cyclopropyl-4-[8-(4-hydroxybutylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCCCCO)C3=NC=2)=CC=C1C(=O)NC1CC1 KYPBWUWXWHYHAG-UHFFFAOYSA-N 0.000 claims 1
- GBJJEOMGAISHBT-UHFFFAOYSA-N n-cyclopropyl-4-[8-(pentylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCCCC)=NC=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 GBJJEOMGAISHBT-UHFFFAOYSA-N 0.000 claims 1
- MLIWMELHHJOIKZ-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 MLIWMELHHJOIKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229960000581 salicylamide Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 0 CCOc1c(C)c(C(*(C)(C)*)=O)c(*)c(*)c1 Chemical compound CCOc1c(C)c(C(*(C)(C)*)=O)c(*)c(*)c1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10195702 | 2010-12-17 | ||
| EP10195702.5 | 2010-12-17 | ||
| PCT/EP2011/072583 WO2012080229A1 (en) | 2010-12-17 | 2011-12-13 | Imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment hyperproliferative disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014503521A JP2014503521A (ja) | 2014-02-13 |
| JP2014503521A5 true JP2014503521A5 (https=) | 2015-01-15 |
Family
ID=45349508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013543704A Pending JP2014503521A (ja) | 2010-12-17 | 2011-12-13 | 過増殖性障害の処置におけるｍｐｓ−１およびｔｋｋ阻害剤としての使用のための、イミダゾピラジン類 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20130303532A1 (https=) |
| EP (1) | EP2651948A1 (https=) |
| JP (1) | JP2014503521A (https=) |
| CN (1) | CN103415518A (https=) |
| CA (1) | CA2821829A1 (https=) |
| WO (1) | WO2012080229A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| US9284317B2 (en) * | 2010-12-17 | 2016-03-15 | Bayer Intellectual Property Gmbh | Substituted imidazo[1,2-a]pyrazines as MPS-1 inhibitors |
| WO2014020043A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| WO2014020041A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| US9573954B2 (en) | 2012-11-16 | 2017-02-21 | University Health Network | Pyrazolopyrimidine compounds |
| JP6095857B2 (ja) * | 2013-11-15 | 2017-03-15 | ユニバーシティ・ヘルス・ネットワーク | ピラゾロピリミジン化合物 |
| US9856258B2 (en) | 2014-04-07 | 2018-01-02 | Netherlands Translational Research Center B.V. | (5,6-dihydro)pyrimido[4,5-E]indolizines |
| FI3283642T3 (fi) | 2015-04-17 | 2024-01-11 | Crossfire Oncology Holding B V | Prognostisia biomarkkereita ttk-inhibiittorikemoterapiaan |
| AU2017299850B2 (en) * | 2016-07-18 | 2021-05-27 | University Health Network | Solid forms of TTK inhibitor |
| KR102660894B1 (ko) * | 2021-09-17 | 2024-04-26 | 기초과학연구원 | 피리미딘-2-아민 화합물의 제조방법 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| IL127566A0 (en) | 1996-08-28 | 1999-10-28 | Pfizer | Substituted 6,5-hetero- bicyclic derivatives |
| US7186832B2 (en) * | 2003-02-20 | 2007-03-06 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| WO2007025090A2 (en) | 2005-08-25 | 2007-03-01 | Kalypsys, Inc. | Heterobicyclic and - tricyclic inhibitors of mapk/erk kinase |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| US20070078136A1 (en) | 2005-09-22 | 2007-04-05 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| US8268809B2 (en) * | 2006-09-05 | 2012-09-18 | Emory University | Kinase inhibitors for preventing or treating pathogen infection and method of use thereof |
| GB0716292D0 (en) * | 2007-08-21 | 2007-09-26 | Biofocus Dpi Ltd | Imidazopyrazine compounds |
| MX2010002115A (es) * | 2007-08-23 | 2010-06-01 | Aztrazeneca Ab | 2-anilinopurin-8-onas como inhibidores de ttk/mps1 para el tratamiento de trastornos .proliferativos. |
| TWI491610B (zh) | 2008-10-09 | 2015-07-11 | 必治妥美雅史谷比公司 | 作為激酶抑制劑之咪唑并嗒腈 |
| CN102413831B (zh) * | 2009-04-29 | 2014-06-04 | 拜耳知识产权有限责任公司 | 取代的咪唑并喹喔啉 |
| TW201107329A (en) | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| CA2772790C (en) | 2009-09-04 | 2017-06-27 | Benjamin Bader | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
| EP2343297A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| EP2343295A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridine derivates |
| EP2343294A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
-
2011
- 2011-12-13 CN CN2011800677581A patent/CN103415518A/zh active Pending
- 2011-12-13 JP JP2013543704A patent/JP2014503521A/ja active Pending
- 2011-12-13 CA CA2821829A patent/CA2821829A1/en not_active Abandoned
- 2011-12-13 WO PCT/EP2011/072583 patent/WO2012080229A1/en not_active Ceased
- 2011-12-13 US US13/994,865 patent/US20130303532A1/en not_active Abandoned
- 2011-12-13 EP EP11796995.6A patent/EP2651948A1/en not_active Withdrawn
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