CA2979024C - Fused bicyclic heteroaryl derivatives having activity as phd inhibitors - Google Patents
Fused bicyclic heteroaryl derivatives having activity as phd inhibitors Download PDFInfo
- Publication number
- CA2979024C CA2979024C CA2979024A CA2979024A CA2979024C CA 2979024 C CA2979024 C CA 2979024C CA 2979024 A CA2979024 A CA 2979024A CA 2979024 A CA2979024 A CA 2979024A CA 2979024 C CA2979024 C CA 2979024C
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- CA
- Canada
- Prior art keywords
- triazolo
- pyridin
- benzonitrile
- cyano
- fluoro
- Prior art date
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- 230000000694 effects Effects 0.000 title description 8
- 239000003112 inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 255
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 206010019280 Heart failures Diseases 0.000 claims abstract description 12
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 11
- 208000009304 Acute Kidney Injury Diseases 0.000 claims abstract description 9
- 208000033626 Renal failure acute Diseases 0.000 claims abstract description 9
- 201000011040 acute kidney failure Diseases 0.000 claims abstract description 9
- 206010007556 Cardiac failure acute Diseases 0.000 claims abstract description 8
- 208000020832 chronic kidney disease Diseases 0.000 claims abstract description 8
- 208000030613 peripheral artery disease Diseases 0.000 claims abstract description 8
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims abstract description 5
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims abstract description 5
- 229940121649 protein inhibitor Drugs 0.000 claims abstract 2
- 239000012268 protein inhibitor Substances 0.000 claims abstract 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 754
- 229910052757 nitrogen Inorganic materials 0.000 claims description 120
- 125000001424 substituent group Chemical group 0.000 claims description 114
- -1 Cl-C6 alkyl Chemical group 0.000 claims description 96
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 80
- 125000000623 heterocyclic group Chemical group 0.000 claims description 80
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 63
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 61
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 57
- 150000002367 halogens Chemical group 0.000 claims description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 48
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 44
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 125000004043 oxo group Chemical group O=* 0.000 claims description 37
- 239000011737 fluorine Substances 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 150000002431 hydrogen Chemical group 0.000 claims description 26
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Chemical group 0.000 claims description 24
- 239000001301 oxygen Chemical group 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000003566 oxetanyl group Chemical group 0.000 claims description 11
- 125000005475 oxolanyl group Chemical group 0.000 claims description 11
- 229940124530 sulfonamide Drugs 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- OQNYMAJNLRQKJB-UHFFFAOYSA-N triazolo[1,5-a]pyridine-7-carboxamide Chemical compound NC(=O)C1=CC=CC2=CN=NN12 OQNYMAJNLRQKJB-UHFFFAOYSA-N 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 229910052702 rhenium Inorganic materials 0.000 claims description 6
- 229910052701 rubidium Inorganic materials 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- NJYYWQHQUOODDL-UHFFFAOYSA-N oxetane-3-carboxamide Chemical compound NC(=O)C1COC1 NJYYWQHQUOODDL-UHFFFAOYSA-N 0.000 claims description 3
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- TYXLWIGNDNJNFS-UHFFFAOYSA-N 4-([1,2,4]triazolo[1,5-c]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=NC=CC2=NC=NN12 TYXLWIGNDNJNFS-UHFFFAOYSA-N 0.000 claims description 2
- KHGDXQZJKLJOIK-UHFFFAOYSA-N 4-[7-[(2,2,2-trifluoroethylamino)methyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound FC(F)(F)CNCC1=CC2=NC=NN2C(=C1)C1=CC=C(C=C1)C#N KHGDXQZJKLJOIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
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- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 9
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- QMHVUOAGWLRDPP-UHFFFAOYSA-N 4-(7-amino-6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound NC1=CC=2N(C(=C1F)C1=CC=C(C#N)C=C1)N=CN=2 QMHVUOAGWLRDPP-UHFFFAOYSA-N 0.000 claims 1
- HNUCQKUWOZDYFO-UHFFFAOYSA-N 4-(7-benzylsulfanyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(SCC2=CC=CC=C2)=CC2=NC=NN12 HNUCQKUWOZDYFO-UHFFFAOYSA-N 0.000 claims 1
- ULZXKIMTJAMTGW-UHFFFAOYSA-N 4-[7-[(oxolan-3-ylamino)methyl]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]benzonitrile Chemical compound N#CC1=CC=C(C=C1)C1=CC(CNC2CCOC2)=CC2=NC=NN12 ULZXKIMTJAMTGW-UHFFFAOYSA-N 0.000 claims 1
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- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- JDQJVFORFISJLJ-UHFFFAOYSA-N N-[5-(4-cyano-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-3,3,3-trifluoropropanamide Chemical compound CC1=C(C=CC(=C1)C#N)C1=CC(NC(=O)CC(F)(F)F)=CC2=NC=NN12 JDQJVFORFISJLJ-UHFFFAOYSA-N 0.000 claims 1
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- OFQIHMZPWBHZJH-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-(oxetan-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)CC2COC2)=CC2=NC=NN12)C#N OFQIHMZPWBHZJH-UHFFFAOYSA-N 0.000 claims 1
- UHZBVANUVKROCY-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-cyclopropylacetamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)CC2CC2)=CC2=NC=NN12)C#N UHZBVANUVKROCY-UHFFFAOYSA-N 0.000 claims 1
- RBCCWUJRBHHFSC-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-3-fluorocyclobutane-1-carboxamide Chemical compound FC1CC(C1)C(=O)NC1=CC2=NC=NN2C(=C1)C1=CC(F)=C(C=C1)C#N RBCCWUJRBHHFSC-UHFFFAOYSA-N 0.000 claims 1
- KIDNTTIYEICQIJ-UHFFFAOYSA-N N-[5-(4-cyano-3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]cyclopropanecarboxamide Chemical compound FC1=C(C=CC(=C1)C1=CC(NC(=O)C2CC2)=CC2=NC=NN12)C#N KIDNTTIYEICQIJ-UHFFFAOYSA-N 0.000 claims 1
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- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
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Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1504565.1 | 2015-03-18 | ||
| GBGB1504565.1A GB201504565D0 (en) | 2015-03-18 | 2015-03-18 | Novel compounds |
| PCT/JP2016/059782 WO2016148306A1 (en) | 2015-03-18 | 2016-03-17 | Fused bicyclic heteroaryl derivatives having activity as phd inhibitors |
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| Publication Number | Publication Date |
|---|---|
| CA2979024A1 CA2979024A1 (en) | 2016-09-22 |
| CA2979024C true CA2979024C (en) | 2024-02-20 |
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| CA2979024A Active CA2979024C (en) | 2015-03-18 | 2016-03-17 | Fused bicyclic heteroaryl derivatives having activity as phd inhibitors |
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| AU2017222417B2 (en) | 2016-02-24 | 2020-07-09 | Pfizer Inc. | Pyrazolo[1,5-a]pyrazin-4-yl derivatives as JAK-inhibitors |
| US11254668B2 (en) | 2017-08-14 | 2022-02-22 | Pfizer Inc. | Pyrazolo[1,5-A]pyrazin-4-yl and related derivatives |
| IL281391B2 (en) | 2018-09-13 | 2025-04-01 | Kissei Pharmaceutical | Imidazopyridinone compound |
| CN110950806A (zh) * | 2019-11-14 | 2020-04-03 | 安庆博曼生物技术有限公司 | 四乙基氯化铵催化嘧啶环羟基氯代制备方法 |
| JP7504822B2 (ja) * | 2020-03-12 | 2024-06-24 | キッセイ薬品工業株式会社 | イミダゾピリジノン化合物を含む医薬組成物 |
| US11718622B2 (en) | 2020-03-16 | 2023-08-08 | Exelixis Inc. | Heterocyclic adenosine receptor antagonists |
| EP4122928A4 (en) * | 2020-04-20 | 2023-12-13 | Shenzhen TargetRx, Inc. | SOLID FORM OF PYRAZINE SUBSTITUTED NICOTINAMIDE AND PRODUCTION AND USE THEREOF |
| AR123848A1 (es) * | 2020-10-20 | 2023-01-18 | Amgen Inc | Compuestos espiro heterocíclicos y métodos de uso |
| US12492178B2 (en) | 2021-09-01 | 2025-12-09 | Empathbio, Inc. | Stable polymorph of R-MDMA HCl |
| TW202334134A (zh) | 2021-10-28 | 2023-09-01 | 香港商英矽智能科技知識產權有限公司 | 含脯胺醯羥化酶結構域之蛋白質(phd)抑制劑及其用途 |
| JP2025500892A (ja) * | 2021-12-17 | 2025-01-15 | アケビア セラピューティクス インコーポレイテッド | 選択的ｐｈｄ１阻害剤化合物、組成物、及び使用方法 |
| EP4457222A4 (en) | 2021-12-28 | 2025-12-24 | Empathbio Inc | MDA AND MDMA NITRIC OXIDE-RELEASING PROMEDICAMENTS |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209621A (en) | 1979-04-27 | 1980-06-24 | American Cyanamid Company | (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines |
| DK135184A (da) * | 1983-03-03 | 1984-10-10 | Riker Laboratories Inc | Triazol(4,3-c)- og triazol(1,5-c)pyrimidiner |
| US4572910A (en) * | 1983-03-03 | 1986-02-25 | Riker Laboratories, Inc. | Triazolo[1,5-c]pyrimidines substituted by nitrogen-containing heterocyclic rings |
| NZ523807A (en) | 2000-06-30 | 2004-09-24 | Wyeth Corp | Substituted-triazolopyrimidines as anticancer agents |
| JP2010065026A (ja) | 2008-08-13 | 2010-03-25 | Ishihara Sangyo Kaisha Ltd | ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤 |
| JP2010065024A (ja) | 2008-08-14 | 2010-03-25 | Ishihara Sangyo Kaisha Ltd | トリアゾロピリミジン誘導体又はその塩を含有する有害生物防除剤 |
| AR077417A1 (es) * | 2009-07-17 | 2011-08-24 | Japan Tobacco Inc | Compuesto triazolopiridina y su accion como inhibidor de prolil hidroxilasa o agente inductor de la produccion de eritropoyetina |
| JP2011168582A (ja) | 2010-01-21 | 2011-09-01 | Ishihara Sangyo Kaisha Ltd | トリアゾロピリジン誘導体又はその塩、それらの製造方法及びそれらを含有する有害生物防除剤 |
| US20150239889A1 (en) | 2012-08-23 | 2015-08-27 | Mitsubishi Tanabe Pharma Corporation | Pyrazolopyrimidine compound |
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