JP2016519147A5 - - Google Patents
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- Publication number
- JP2016519147A5 JP2016519147A5 JP2016514126A JP2016514126A JP2016519147A5 JP 2016519147 A5 JP2016519147 A5 JP 2016519147A5 JP 2016514126 A JP2016514126 A JP 2016514126A JP 2016514126 A JP2016514126 A JP 2016514126A JP 2016519147 A5 JP2016519147 A5 JP 2016519147A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- acceptable salt
- compound
- bipyrazol
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 68
- 150000003839 salts Chemical class 0.000 claims 54
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 50
- -1 H 2 N— Chemical group 0.000 claims 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims 28
- 125000001424 substituent group Chemical group 0.000 claims 20
- 239000003814 drug Substances 0.000 claims 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 10
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 206010028537 myelofibrosis Diseases 0.000 claims 7
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 6
- 208000003476 primary myelofibrosis Diseases 0.000 claims 6
- MSGYSFWCPOBHEV-AWEZNQCLSA-N 4-[3-(cyanomethyl)-3-[4-(3,5-dimethyl-1h-pyrazol-4-yl)pyrazol-1-yl]azetidin-1-yl]-2,5-difluoro-n-[(2s)-1,1,1-trifluoropropan-2-yl]benzamide Chemical compound C1=C(F)C(C(=O)N[C@@H](C)C(F)(F)F)=CC(F)=C1N1CC(CC#N)(N2N=CC(=C2)C2=C(NN=C2C)C)C1 MSGYSFWCPOBHEV-AWEZNQCLSA-N 0.000 claims 5
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000006601 (C1-C3) alkylcarbamyl group Chemical group 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 3
- 208000009527 Refractory anemia Diseases 0.000 claims 3
- 206010072684 Refractory cytopenia with unilineage dysplasia Diseases 0.000 claims 3
- 208000017733 acquired polycythemia vera Diseases 0.000 claims 3
- 208000037244 polycythemia vera Diseases 0.000 claims 3
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 3
- 208000017520 skin disease Diseases 0.000 claims 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 206010058314 Dysplasia Diseases 0.000 claims 2
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims 2
- 206010048643 Hypereosinophilic syndrome Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 206010033661 Pancytopenia Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 208000024389 cytopenia Diseases 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- IADHQAYOJSDLQB-UHFFFAOYSA-N 4-[3-(cyanomethyl)-3-[4-(5-methyl-1H-pyrazol-4-yl)pyrazol-1-yl]azetidin-1-yl]-N-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)c1ccc(cc1)N1CC(CC#N)(C1)n1cc(cn1)-c1c[nH]nc1C IADHQAYOJSDLQB-UHFFFAOYSA-N 0.000 claims 1
- WDEZBQCRCIAJPW-UHFFFAOYSA-N 5-[3-(cyanomethyl)-3-[3-methyl-4-(1H-pyrazol-4-yl)pyrazol-1-yl]azetidin-1-yl]-N-propan-2-ylpyrazine-2-carboxamide Chemical compound CC(C)NC(=O)c1cnc(cn1)N1CC(CC#N)(C1)n1cc(c(C)n1)-c1cn[nH]c1 WDEZBQCRCIAJPW-UHFFFAOYSA-N 0.000 claims 1
- UVNZXZQWOUVYIS-UHFFFAOYSA-N 5-[3-(cyanomethyl)-3-[3-methyl-4-(5-methyl-1H-pyrazol-4-yl)pyrazol-1-yl]azetidin-1-yl]-N-propan-2-ylpyrazine-2-carboxamide Chemical compound CC(C)NC(=O)c1cnc(cn1)N1CC(CC#N)(C1)n1cc(c(C)n1)-c1c[nH]nc1C UVNZXZQWOUVYIS-UHFFFAOYSA-N 0.000 claims 1
- JFFRGYYXQJTLOG-UHFFFAOYSA-N 5-[3-(cyanomethyl)-3-[4-(3,5-dimethyl-1H-pyrazol-4-yl)pyrazol-1-yl]azetidin-1-yl]-N-propan-2-ylpyrazine-2-carboxamide Chemical compound CC(C)NC(=O)c1cnc(cn1)N1CC(CC#N)(C1)n1cc(cn1)-c1c(C)n[nH]c1C JFFRGYYXQJTLOG-UHFFFAOYSA-N 0.000 claims 1
- ZNDIFOVCUNVGNF-UHFFFAOYSA-N 5-[3-(cyanomethyl)-3-[4-(5-methyl-1H-pyrazol-4-yl)pyrazol-1-yl]azetidin-1-yl]-N-propan-2-ylpyrazine-2-carboxamide Chemical compound CC(C)NC(=O)c1cnc(cn1)N1CC(CC#N)(C1)n1cc(cn1)-c1c[nH]nc1C ZNDIFOVCUNVGNF-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000005024 Castleman disease Diseases 0.000 claims 1
- 206010008805 Chromosomal abnormalities Diseases 0.000 claims 1
- 208000031404 Chromosome Aberrations Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 208000010201 Exanthema Diseases 0.000 claims 1
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 claims 1
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 1
- 108060003951 Immunoglobulin Proteins 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 101100095974 Mus musculus Smc3 gene Proteins 0.000 claims 1
- AYNNRIXQAVTECA-ZETCQYMHSA-N N-[(2S)-1,1,1-trifluoropropan-2-yl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)N[C@H](C(F)(F)F)C AYNNRIXQAVTECA-ZETCQYMHSA-N 0.000 claims 1
- BISZGLXXDZHLIN-FJXQXJEOSA-N P(O)(O)(O)=O.C(C1=CC=CC=C1)(=O)N[C@H](C(F)(F)F)C Chemical compound P(O)(O)(O)=O.C(C1=CC=CC=C1)(=O)N[C@H](C(F)(F)F)C BISZGLXXDZHLIN-FJXQXJEOSA-N 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010070834 Sensitisation Diseases 0.000 claims 1
- 206010040880 Skin irritation Diseases 0.000 claims 1
- 206010070835 Skin sensitisation Diseases 0.000 claims 1
- 201000008736 Systemic mastocytosis Diseases 0.000 claims 1
- 208000005485 Thrombocytosis Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 claims 1
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000010928 autoimmune thyroid disease Diseases 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- DDAMPNWYDILDPV-UHFFFAOYSA-N benzamide;phosphoric acid Chemical compound OP(O)(O)=O.NC(=O)C1=CC=CC=C1 DDAMPNWYDILDPV-UHFFFAOYSA-N 0.000 claims 1
- HLWOEQNDJYGYJV-UHFFFAOYSA-N benzamide;sulfuric acid Chemical compound OS(O)(=O)=O.NC(=O)C1=CC=CC=C1 HLWOEQNDJYGYJV-UHFFFAOYSA-N 0.000 claims 1
- 210000000601 blood cell Anatomy 0.000 claims 1
- 210000001185 bone marrow Anatomy 0.000 claims 1
- 208000019664 bone resorption disease Diseases 0.000 claims 1
- 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 201000005884 exanthem Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 102000018358 immunoglobulin Human genes 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 210000004165 myocardium Anatomy 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 206010037844 rash Diseases 0.000 claims 1
- 230000008313 sensitization Effects 0.000 claims 1
- 230000036556 skin irritation Effects 0.000 claims 1
- 231100000475 skin irritation Toxicity 0.000 claims 1
- 231100000046 skin rash Toxicity 0.000 claims 1
- 231100000370 skin sensitisation Toxicity 0.000 claims 1
- 208000009996 subepithelial mucinous corneal dystrophy Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361824683P | 2013-05-17 | 2013-05-17 | |
| US61/824,683 | 2013-05-17 | ||
| PCT/US2014/038388 WO2014186706A1 (en) | 2013-05-17 | 2014-05-16 | Bipyrazole derivatives as jak inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018187613A Division JP6775560B2 (ja) | 2013-05-17 | 2018-10-02 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016519147A JP2016519147A (ja) | 2016-06-30 |
| JP2016519147A5 true JP2016519147A5 (enExample) | 2017-06-29 |
| JP6415543B2 JP6415543B2 (ja) | 2018-10-31 |
Family
ID=50983151
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016514126A Active JP6415543B2 (ja) | 2013-05-17 | 2014-05-16 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
| JP2018187613A Active JP6775560B2 (ja) | 2013-05-17 | 2018-10-02 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
| JP2020168950A Active JP7126741B2 (ja) | 2013-05-17 | 2020-10-06 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
| JP2022128042A Pending JP2022163162A (ja) | 2013-05-17 | 2022-08-10 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
| JP2024079435A Pending JP2024105557A (ja) | 2013-05-17 | 2024-05-15 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018187613A Active JP6775560B2 (ja) | 2013-05-17 | 2018-10-02 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
| JP2020168950A Active JP7126741B2 (ja) | 2013-05-17 | 2020-10-06 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
| JP2022128042A Pending JP2022163162A (ja) | 2013-05-17 | 2022-08-10 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
| JP2024079435A Pending JP2024105557A (ja) | 2013-05-17 | 2024-05-15 | Ｊａｋ阻害剤としてのビピラゾール誘導体 |
Country Status (36)
Families Citing this family (77)
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| DK3184526T3 (en) | 2005-12-13 | 2019-01-14 | Incyte Holdings Corp | PYRROLO [2,3-D] PYRIMIDINE DERIVATIVES AS A JANUS-KINASE INHIBITOR |
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| ES2487542T3 (es) | 2009-05-22 | 2014-08-21 | Incyte Corporation | Derivados de N-(hetero)aril-pirrolidina de pirazol-4-il-pirrolo[2,3-d]pirimidinas y pirrol-3-il-pirrolo[2,3-d]pirimidinas como inhibidores de cinasas Janus |
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| PE20120493A1 (es) | 2009-06-29 | 2012-05-20 | Incyte Corp | Pirimidinonas como inhibidores de pi3k |
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| CN118453493A (zh) | 2015-05-29 | 2024-08-09 | 西德奈克西斯公司 | D2o稳定化的药物制剂 |
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| WO2017120194A1 (en) | 2016-01-05 | 2017-07-13 | Incyte Corporation | Pyridine and pyridimine compounds as pi3k-gamma inhibitors |
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| CN107759623B (zh) * | 2016-08-23 | 2020-08-14 | 苏州旺山旺水生物医药有限公司 | Jak抑制剂的中间体及其制备方法 |
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