JP5805653B2 - トリアゾロピリジン - Google Patents
トリアゾロピリジン Download PDFInfo
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- JP5805653B2 JP5805653B2 JP2012541336A JP2012541336A JP5805653B2 JP 5805653 B2 JP5805653 B2 JP 5805653B2 JP 2012541336 A JP2012541336 A JP 2012541336A JP 2012541336 A JP2012541336 A JP 2012541336A JP 5805653 B2 JP5805653 B2 JP 5805653B2
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- Prior art keywords
- alkyl
- alkoxy
- halo
- group
- compound
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- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 title 1
- -1 hydroxyl- Chemical group 0.000 claims description 335
- 150000001875 compounds Chemical class 0.000 claims description 254
- 239000000203 mixture Substances 0.000 claims description 151
- 125000005843 halogen group Chemical group 0.000 claims description 73
- 150000003839 salts Chemical class 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 31
- 201000010099 disease Diseases 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 239000012453 solvate Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 150000001502 aryl halides Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 241000255925 Diptera Species 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 88
- 239000000243 solution Substances 0.000 description 78
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000000543 intermediate Substances 0.000 description 58
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 238000004519 manufacturing process Methods 0.000 description 42
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
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- 238000010898 silica gel chromatography Methods 0.000 description 22
- 229910052786 argon Inorganic materials 0.000 description 21
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- 239000002253 acid Substances 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 16
- 238000005859 coupling reaction Methods 0.000 description 16
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 230000005778 DNA damage Effects 0.000 description 11
- 231100000277 DNA damage Toxicity 0.000 description 11
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
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- 150000001204 N-oxides Chemical class 0.000 description 9
- 239000012317 TBTU Substances 0.000 description 9
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 9
- 125000002619 bicyclic group Chemical group 0.000 description 9
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (3)
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| JP2013512264A JP2013512264A (ja) | 2013-04-11 |
| JP2013512264A5 JP2013512264A5 (enExample) | 2013-12-26 |
| JP5805653B2 true JP5805653B2 (ja) | 2015-11-04 |
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| JP2012541336A Expired - Fee Related JP5805653B2 (ja) | 2009-11-30 | 2010-11-17 | トリアゾロピリジン |
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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 |
| CN103370322B (zh) | 2010-12-17 | 2016-02-10 | 拜耳知识产权有限责任公司 | 在过度增殖性病症的治疗中用作mps-1和tkk抑制剂的2-取代的咪唑并吡嗪 |
| JP2013545779A (ja) | 2010-12-17 | 2013-12-26 | 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 | 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６置換イミダゾピラジン |
| US20140187548A1 (en) | 2010-12-17 | 2014-07-03 | Bayer Intellectual Property Gmbh | 6 substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| JP2014503521A (ja) | 2010-12-17 | 2014-02-13 | 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 | 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 |
| ES2556458T3 (es) | 2010-12-17 | 2016-01-18 | Bayer Intellectual Property Gmbh | 6-Imidazopirazinas sustituidas para uso como inhibidores de Mps-1 y TKK en el tratamiento de trastornos hiperproliferativos |
| US9212184B2 (en) | 2010-12-17 | 2015-12-15 | Bayer Intellectual Property Gmbh | 6-thio-substituted imidazo[1,2-a]pyrazines as Mps-1 inhibitors |
| CN103582632B (zh) | 2011-03-31 | 2015-08-19 | 拜耳知识产权有限责任公司 | 取代的苯并咪唑 |
| WO2012136531A1 (en) | 2011-04-06 | 2012-10-11 | Bayer Pharma Aktiengesellschaft | Substituted imidazopyridines and intermediates thereof |
| EP2699575B1 (en) | 2011-04-21 | 2015-03-25 | 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 |
| JP6166289B2 (ja) | 2012-03-14 | 2017-07-19 | 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 | 置換イミダゾピリダジン |
| EA027544B1 (ru) | 2012-07-10 | 2017-08-31 | Байер Фарма Акциенгезельшафт | Способ получения замещенных триазолопиридинов |
| 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 |
| HK1215250A1 (zh) | 2013-01-30 | 2016-08-19 | Bayer Pharma Aktiengesellschaft | 氨基取代的异噻唑 |
| AR096469A1 (es) * | 2013-06-06 | 2015-12-30 | Bayer Pharma AG | Composiciones farmacéuticas que comprenden compuestos del tipo triazolpiridinas |
| CA2914516A1 (en) * | 2013-06-07 | 2014-12-11 | Bayer Pharma Aktiengesellschaft | Substituted triazolopyridines |
| RS56034B1 (sr) * | 2013-06-11 | 2017-09-29 | Bayer Pharma AG | Derivati prolekova supstituisanih triazolopiridina |
| EA201600003A1 (ru) | 2013-06-11 | 2016-06-30 | Байер Фарма Акциенгезельшафт | КОМБИНАЦИИ ДЛЯ ЛЕЧЕНИЯ РАКА, СОДЕРЖАЩИЕ ИНГИБИТОР Mps-1 КИНАЗЫ И ИНГИБИТОР МИТОЗА |
| EP2980088A1 (en) | 2014-07-28 | 2016-02-03 | Bayer Pharma Aktiengesellschaft | Amino-substituted isothiazoles |
| PT3129374T (pt) | 2014-04-07 | 2019-03-25 | Netherlands Translational Res Center B V | (5,6-dihidro)pirimido[4,5-e] indolizinas |
| 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 |
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| 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 |
| JP7023217B2 (ja) | 2017-12-01 | 2022-02-21 | ダイキン工業株式会社 | アルカリ接触する表面を有する構成要素 |
| EP3876930A4 (en) | 2018-11-07 | 2022-07-20 | Dana-Farber Cancer Institute, Inc. | BENZIMIDAZOLE DERIVATIVES AND AZA-BENZIMIDAZOLE DERIVATIVES AS JANUS KINASE 2 INHIBITORS AND THEIR USES |
| 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 |
| US12415816B2 (en) | 2018-11-07 | 2025-09-16 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| WO2021226261A1 (en) | 2020-05-06 | 2021-11-11 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| EP4267574B1 (en) | 2020-12-23 | 2025-04-23 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| US20240123043A1 (en) * | 2021-02-22 | 2024-04-18 | Orgenesis Inc. | Pharmaceutical compositions comprising ranpirnase |
| WO2023086320A1 (en) | 2021-11-09 | 2023-05-19 | Ajax Therapeutics, Inc. | Forms and compositions of inhibitors of jak2 |
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| EP2343294A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
| 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 |
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