CA2781915A1 - Triazolopyridines - Google Patents
Triazolopyridines Download PDFInfo
- Publication number
- CA2781915A1 CA2781915A1 CA2781915A CA2781915A CA2781915A1 CA 2781915 A1 CA2781915 A1 CA 2781915A1 CA 2781915 A CA2781915 A CA 2781915A CA 2781915 A CA2781915 A CA 2781915A CA 2781915 A1 CA2781915 A1 CA 2781915A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkoxy
- halo
- nr8r7
- phenyl
- 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.)
- Abandoned
Links
- 150000008523 triazolopyridines Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 271
- 238000000034 method Methods 0.000 claims abstract description 91
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 51
- 238000002360 preparation method Methods 0.000 claims abstract description 50
- 238000011282 treatment Methods 0.000 claims abstract description 34
- 201000010099 disease Diseases 0.000 claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 238000011321 prophylaxis Methods 0.000 claims abstract description 14
- -1 hydroxyl- Chemical group 0.000 claims description 308
- 239000000203 mixture Substances 0.000 claims description 153
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 134
- 206010028980 Neoplasm Diseases 0.000 claims description 67
- 125000005843 halogen group Chemical group 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 27
- 239000012453 solvate Substances 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 150000001204 N-oxides Chemical class 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 230000004663 cell proliferation Effects 0.000 claims description 19
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 206010027476 Metastases Diseases 0.000 claims description 16
- 230000024932 T cell mediated immunity Effects 0.000 claims description 16
- 230000001413 cellular effect Effects 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 230000028709 inflammatory response Effects 0.000 claims description 16
- 230000004083 survival effect Effects 0.000 claims description 16
- 230000010261 cell growth Effects 0.000 claims description 15
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
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- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 7
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000001502 aryl halides Chemical class 0.000 claims description 6
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
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- 230000001404 mediated effect Effects 0.000 claims description 6
- 210000002307 prostate Anatomy 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 206010059282 Metastases to central nervous system Diseases 0.000 claims description 5
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 5
- 206010029098 Neoplasm skin Diseases 0.000 claims description 5
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 4
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- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 4
- 229930012538 Paclitaxel Natural products 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 4
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- 108010006654 Bleomycin Proteins 0.000 claims description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims description 3
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims description 3
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 3
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- 229960004679 doxorubicin Drugs 0.000 claims description 3
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- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims description 3
- 229960002074 flutamide Drugs 0.000 claims description 3
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 claims description 3
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- 229960001101 ifosfamide Drugs 0.000 claims description 3
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 3
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 3
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- 229960001156 mitoxantrone Drugs 0.000 claims description 3
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims description 3
- 229960000624 procarbazine Drugs 0.000 claims description 3
- 229960003087 tioguanine Drugs 0.000 claims description 3
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims description 3
- 229960004528 vincristine Drugs 0.000 claims description 3
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- BYOWPAFNUFYUGB-UHFFFAOYSA-N 1-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)NC=4C=NC=CC=4)C=CC=3)C=CC2=N1 BYOWPAFNUFYUGB-UHFFFAOYSA-N 0.000 claims description 2
- GMSHWFIJJKGZLZ-UHFFFAOYSA-N 1-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)NC=4C=CN=CC=4)C=CC=3)C=CC2=N1 GMSHWFIJJKGZLZ-UHFFFAOYSA-N 0.000 claims description 2
- IYKHSNHPHQJOJT-UHFFFAOYSA-N 1-[4-[2-(2-cyanoanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-3-phenylurea Chemical compound C=1C=C(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)C=CC=1NC(=O)NC1=CC=CC=C1 IYKHSNHPHQJOJT-UHFFFAOYSA-N 0.000 claims description 2
- WCUJJQNTRQICDW-UHFFFAOYSA-N 1-cyclopropyl-3-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]urea Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)NC4CC4)C=CC=3)C=CC2=N1 WCUJJQNTRQICDW-UHFFFAOYSA-N 0.000 claims description 2
- VJYWUMCIEQFWOZ-UHFFFAOYSA-N 2-[[6-[3-(4-methylpiperazine-1-carbonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzonitrile Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)=C1 VJYWUMCIEQFWOZ-UHFFFAOYSA-N 0.000 claims description 2
- HZXUEKUQMUGYND-UHFFFAOYSA-N 2-amino-2-phenyl-n-[4-[2-[2-(trifluoromethyl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]acetamide Chemical compound C=1C=CC=CC=1C(N)C(=O)NC(C=C1)=CC=C1C(=CN1N=2)C=CC1=NC=2NC1=CC=CC=C1C(F)(F)F HZXUEKUQMUGYND-UHFFFAOYSA-N 0.000 claims description 2
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- GJNZQIYIBHONFC-UHFFFAOYSA-N 2-phenyl-n-[4-[2-[2-(trifluoromethyl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC=CC=4)=CC=3)C=CC2=N1 GJNZQIYIBHONFC-UHFFFAOYSA-N 0.000 claims description 2
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- GINCZLFUPXTESW-UHFFFAOYSA-N 3-[2-(2-cyanoanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-n-cyclopentylbenzamide Chemical compound C=1C=CC(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)=CC=1C(=O)NC1CCCC1 GINCZLFUPXTESW-UHFFFAOYSA-N 0.000 claims description 2
- KGCRBQXVXUNBQF-UHFFFAOYSA-N 3-[2-(2-cyanoanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-n-cyclopropylbenzamide Chemical compound C=1C=CC(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)=CC=1C(=O)NC1CC1 KGCRBQXVXUNBQF-UHFFFAOYSA-N 0.000 claims description 2
- PHQATLHJAVUULF-UHFFFAOYSA-N 4-(dimethylamino)-n-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]piperidine-1-carboxamide Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)N4CCC(CC4)N(C)C)C=CC=3)C=CC2=N1 PHQATLHJAVUULF-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP09075535.6 | 2009-11-30 | ||
| EP09075535A EP2343297A1 (en) | 2009-11-30 | 2009-11-30 | Triazolopyridines |
| PCT/EP2010/006994 WO2011063908A1 (en) | 2009-11-30 | 2010-11-17 | Triazolopyridines |
Publications (1)
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| CA2781915A1 true CA2781915A1 (en) | 2011-06-03 |
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Country Status (36)
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| EP2343297A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| EP2343294A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
| UY33452A (es) * | 2010-06-16 | 2012-01-31 | Bayer Schering Pharma Ag | Triazolopiridinas sustituidas |
| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| CA2821817A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | Substituted 6-imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| US20130303532A1 (en) | 2010-12-17 | 2013-11-14 | Bayer Intellectual Property Gmbh | Imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment hyperproliferative disorders |
| US20140135319A1 (en) | 2010-12-17 | 2014-05-15 | Bayer Intellectual Property Gmbh | 6-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| JP5822944B2 (ja) | 2010-12-17 | 2015-11-25 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 過剰増殖性障害の治療におけるｍｐｓ−１およびｔｋｋ阻害剤として使用するための２置換イミダゾピラジン |
| CA2821827A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | 6-thio-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| EP2651950A1 (en) | 2010-12-17 | 2013-10-23 | Bayer Intellectual Property GmbH | 6 substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| US9388140B2 (en) | 2011-03-31 | 2016-07-12 | Bayer Intellectual Property Gmbh | Substituted benzimidazoles |
| JP5951750B2 (ja) | 2011-04-06 | 2016-07-13 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾピリジン類およびその中間体 |
| AU2012244859B2 (en) * | 2011-04-21 | 2017-06-08 | Bayer Intellectual Property Gmbh | Triazolopyridines |
| WO2012160029A1 (en) | 2011-05-23 | 2012-11-29 | Bayer Intellectual Property Gmbh | Substituted triazolopyridines |
| UA112096C2 (uk) * | 2011-12-12 | 2016-07-25 | Байєр Інтеллектуал Проперті Гмбх | Заміщені триазолопіридини та їх застосування як інгібіторів ttk |
| CA2867061A1 (en) | 2012-03-14 | 2013-09-19 | Bayer Intellectual Property Gmbh | Substituted imidazopyridazines |
| JP6238979B2 (ja) * | 2012-07-10 | 2017-11-29 | バイエル・ファルマ・アクティエンゲゼルシャフト | 置換トリアゾロピリジンを調製する方法 |
| 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 |
| US9682995B2 (en) | 2013-01-30 | 2017-06-20 | Bayer Pharma Aktiengesellschaft | Amino-substituted isothiazoles |
| AR096469A1 (es) * | 2013-06-06 | 2015-12-30 | Bayer Pharma AG | Composiciones farmacéuticas que comprenden compuestos del tipo triazolpiridinas |
| US9670202B2 (en) * | 2013-06-07 | 2017-06-06 | Bayer Pharma Aktiengesellschaft | Substituted triazolopyridines |
| DK3008062T3 (en) | 2013-06-11 | 2017-06-12 | Bayer Pharma AG | PRODRUG DERIVATIVES OF SUBSTITUTED TRIAZOLOPYRIDINES |
| US20160128988A1 (en) | 2013-06-11 | 2016-05-12 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer comprising a mps-1 kinase inhibitor and a mitotic inhibitor |
| EP2980088A1 (en) | 2014-07-28 | 2016-02-03 | Bayer Pharma Aktiengesellschaft | Amino-substituted isothiazoles |
| WO2015155042A1 (en) | 2014-04-07 | 2015-10-15 | Netherlands Translational Research Center B.V. | (5,6-dihydro)pyrimido[4,5-e]indolizines |
| EP2977375A1 (en) | 2014-07-25 | 2016-01-27 | Bayer Pharma Aktiengesellschaft | Amino-substituted isoxazoles |
| EP2977377A1 (en) | 2014-07-25 | 2016-01-27 | Bayer Pharma Aktiengesellschaft | Amino-substituted isoxazoles |
| EP2977376A1 (en) | 2014-07-25 | 2016-01-27 | Bayer Pharma Aktiengesellschaft | Amino-substituted isoxazoles |
| US11208696B2 (en) | 2015-04-17 | 2021-12-28 | Netherlands Translational Research Center B.V. | Prognostic biomarkers for TTK inhibitor chemotherapy |
| KR101686411B1 (ko) * | 2015-12-28 | 2016-12-14 | 한국원자력의학원 | 피리딘계 유도체를 포함하는 암 예방 또는 치료용 조성물 |
| CN107641118B (zh) * | 2016-07-22 | 2020-11-06 | 爱科诺生物医药股份有限公司 | 具有细胞坏死抑制活性的化合物及其组合物和应用 |
| EP3492500B1 (en) | 2017-12-01 | 2023-09-20 | Daikin Industries, Ltd. | Use of a crosslinked product of a fluorine-containing amorphous elastomer |
| EP3877371A4 (en) * | 2018-11-07 | 2022-07-27 | Dana-Farber Cancer Institute, Inc. | IMIDAZOPYRIDINE DERIVATIVES AND AZA-IMIDAZOPYRIDINE DERIVATIVES USED AS JANUS KINASE 2 INHIBITORS AND ASSOCIATED USES |
| EP3876939A4 (en) | 2018-11-07 | 2022-08-10 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| BR112022022409A2 (pt) | 2020-05-06 | 2023-02-07 | Ajax Therapeutics Inc | 6-heteroarilóxi benzimidazóis e azabenzimidazóis como inibidores de jak2 |
| EP4267574B1 (en) | 2020-12-23 | 2025-04-23 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| WO2022178340A2 (en) * | 2021-02-22 | 2022-08-25 | Orgenesis Inc. | Pharmaceutical compositions comprising ranpirnase |
| WO2023086320A1 (en) | 2021-11-09 | 2023-05-19 | Ajax Therapeutics, Inc. | Forms and compositions of inhibitors of jak2 |
| US11970494B2 (en) | 2021-11-09 | 2024-04-30 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as JAK2 inhibitors |
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| US6514989B1 (en) | 2001-07-20 | 2003-02-04 | Hoffmann-La Roche Inc. | Aromatic and heteroaromatic substituted 1,2,4-triazolo pyridine derivatives |
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| JP2008515874A (ja) | 2004-10-07 | 2008-05-15 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 抗菌薬 |
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| NZ573015A (en) | 2006-05-31 | 2010-11-26 | Galapagos Nv | Triazolopyrazine compounds useful for the treatment of degenerative & inflammatory diseases |
| MX2009002171A (es) | 2006-08-30 | 2009-05-28 | Cellzome Ltd | Derivados de triazol como inhibidores de cinasas. |
| AU2008277628B2 (en) * | 2007-07-18 | 2012-03-15 | Novartis Ag | Bicyclic heteroaryl compounds and their use as kinase inhibitors |
| CN103298814A (zh) * | 2007-08-23 | 2013-09-11 | 阿斯利康(瑞典)有限公司 | 作为治疗增殖性疾病的ttk/mps1抑制剂的2-苯胺基嘌呤-8-酮 |
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| EP2424537B1 (en) | 2009-04-29 | 2015-07-08 | Bayer Intellectual Property GmbH | Substituted imidazoquinoxalines |
| EP2473498A1 (en) | 2009-09-04 | 2012-07-11 | Bayer Pharma Aktiengesellschaft | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
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| US9145399B2 (en) | 2010-01-15 | 2015-09-29 | Janssen Pharmaceuticals, Inc. | Substituted bicyclic triazole derivatives as gamma secretase modulators |
| US20110190269A1 (en) | 2010-02-01 | 2011-08-04 | Karlheinz Baumann | Gamma secretase modulators |
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- 2012-05-25 TN TNP2012000265A patent/TN2012000265A1/en unknown
- 2012-05-28 MA MA34899A patent/MA33768B1/fr unknown
- 2012-05-30 DO DO2012000150A patent/DOP2012000150A/es unknown
- 2012-05-30 EC ECSP12011935 patent/ECSP12011935A/es unknown
- 2012-05-30 CR CR20120295A patent/CR20120295A/es unknown
- 2012-05-30 GT GT201200165A patent/GT201200165A/es unknown
- 2012-05-30 HN HN2012001162A patent/HN2012001162A/es unknown
- 2012-05-30 CL CL2012001391A patent/CL2012001391A1/es unknown
-
2014
- 2014-11-21 CY CY20141100970T patent/CY1115866T1/el unknown
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20150914 |
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| FZDE | Discontinued |
Effective date: 20190517 |