JP2017536342A5 - - Google Patents
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- JP2017536342A5 JP2017536342A5 JP2017518848A JP2017518848A JP2017536342A5 JP 2017536342 A5 JP2017536342 A5 JP 2017536342A5 JP 2017518848 A JP2017518848 A JP 2017518848A JP 2017518848 A JP2017518848 A JP 2017518848A JP 2017536342 A5 JP2017536342 A5 JP 2017536342A5
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- JP
- Japan
- Prior art keywords
- group
- compound
- phenyl
- hydrogen atom
- alkyl group
- 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.)
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 19
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 230000005764 inhibitory process Effects 0.000 claims description 10
- 230000013823 prenylation Effects 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- -1 indol-3-ylacetyl Chemical group 0.000 claims description 5
- 230000006806 disease prevention Effects 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- FFLLURWCCBLIPK-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound ClC1=CC=C(C=C1)C1(CCN(CC1)C1=NC=CC(=N1)C(C#N)C1=NC=CC=C1)O FFLLURWCCBLIPK-UHFFFAOYSA-N 0.000 claims 3
- 210000004072 lung Anatomy 0.000 claims 3
- SLIHKZMEBDTISW-UHFFFAOYSA-N 2-[2-(4-benzoylpiperidin-1-yl)pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound C(C1=CC=CC=C1)(=O)C1CCN(CC1)C1=NC=CC(=N1)C(C#N)C1=NC=CC=C1 SLIHKZMEBDTISW-UHFFFAOYSA-N 0.000 claims 2
- WWVUFIARDMUQAF-UHFFFAOYSA-N 2-[2-(4-benzyl-4-hydroxypiperidin-1-yl)pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound C(C1=CC=CC=C1)C1(CCN(CC1)C1=NC=CC(=N1)C(C#N)C1=NC=CC=C1)O WWVUFIARDMUQAF-UHFFFAOYSA-N 0.000 claims 2
- UDVVLWUWXAYAPQ-UHFFFAOYSA-N 2-[2-[4-[(2,4-difluorophenyl)methyl]piperazin-1-yl]pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound FC1=C(CN2CCN(CC2)C2=NC=CC(=N2)C(C#N)C2=NC=CC=C2)C=CC(=C1)F UDVVLWUWXAYAPQ-UHFFFAOYSA-N 0.000 claims 2
- CTAXMXBMTOKFLM-UHFFFAOYSA-N 2-[2-[4-[(2-fluorophenyl)methyl]piperazin-1-yl]pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound FC1=C(CN2CCN(CC2)C2=NC=CC(=N2)C(C#N)C2=NC=CC=C2)C=CC=C1 CTAXMXBMTOKFLM-UHFFFAOYSA-N 0.000 claims 2
- OGSGYMROCHYIAT-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methyl]piperazin-1-yl]pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound FC=1C=C(CN2CCN(CC2)C2=NC=CC(=N2)C(C#N)C2=NC=CC=C2)C=CC=1 OGSGYMROCHYIAT-UHFFFAOYSA-N 0.000 claims 2
- JKBLQQZBPDYGLK-UHFFFAOYSA-N 2-[2-[4-[(3-methylphenyl)methyl]piperazin-1-yl]pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound CC=1C=C(CN2CCN(CC2)C2=NC=CC(=N2)C(C#N)C2=NC=CC=C2)C=CC=1 JKBLQQZBPDYGLK-UHFFFAOYSA-N 0.000 claims 2
- UFXQRLHSTCELGP-UHFFFAOYSA-N 2-[2-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound FC1=CC=C(CN2CCN(CC2)C2=NC=CC(=N2)C(C#N)C2=NC=CC=C2)C=C1 UFXQRLHSTCELGP-UHFFFAOYSA-N 0.000 claims 2
- XSIWERFBBSWXKP-UHFFFAOYSA-N 2-[2-[4-[(6-fluoro-4H-1,3-benzodioxin-8-yl)methyl]piperazin-1-yl]pyrimidin-4-yl]-2-pyridin-2-ylacetonitrile Chemical compound FC=1C=C(C2=C(COCO2)C=1)CN1CCN(CC1)C1=NC=CC(=N1)C(C#N)C1=NC=CC=C1 XSIWERFBBSWXKP-UHFFFAOYSA-N 0.000 claims 2
- LKBMGMLGAVDVQH-UHFFFAOYSA-N 2-pyridin-4-yl-2-[6-[4-(thiophene-2-carbonyl)piperazin-1-yl]pyrimidin-4-yl]acetonitrile Chemical compound N1=CC=C(C=C1)C(C#N)C1=NC=NC(=C1)N1CCN(CC1)C(=O)C=1SC=CC=1 LKBMGMLGAVDVQH-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 229940072107 ascorbate Drugs 0.000 claims 2
- 235000010323 ascorbic acid Nutrition 0.000 claims 2
- 239000011668 ascorbic acid Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 229940095064 tartrate Drugs 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010063493 Premature ageing Diseases 0.000 claims 1
- 208000032038 Premature aging Diseases 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- LDACQIXSCLBKTN-UHFFFAOYSA-N [4-[6-(N,3-dimethylanilino)pyrimidin-4-yl]piperazin-1-yl]-(1-phenyl-5-propylpyrazol-4-yl)methanone Chemical compound CN(C1=CC(=NC=N1)N1CCN(CC1)C(=O)C=1C=NN(C=1CCC)C1=CC=CC=C1)C=1C=C(C=CC=1)C LDACQIXSCLBKTN-UHFFFAOYSA-N 0.000 claims 1
- 210000004100 adrenal gland Anatomy 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 208000026106 cerebrovascular disease Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 229940049920 malate Drugs 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 208000012268 mitochondrial disease Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 230000009759 skin aging Effects 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 210000001215 vagina Anatomy 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 0 *N1CCNCC1 Chemical compound *N1CCNCC1 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- BLDNWXVISIXWKZ-UHFFFAOYSA-N CCc(cc1)ccc1F Chemical compound CCc(cc1)ccc1F BLDNWXVISIXWKZ-UHFFFAOYSA-N 0.000 description 1
- JTQKFJWXQHKANB-UHFFFAOYSA-N CCc(cc1F)ccc1F Chemical compound CCc(cc1F)ccc1F JTQKFJWXQHKANB-UHFFFAOYSA-N 0.000 description 1
- GGLWSLBFZLEDEF-UHFFFAOYSA-N CCc(ccc(F)c1)c1F Chemical compound CCc(ccc(F)c1)c1F GGLWSLBFZLEDEF-UHFFFAOYSA-N 0.000 description 1
- NWKUOCHFUQGXNS-UHFFFAOYSA-N CCc1cc(F)cc2c1COCO2 Chemical compound CCc1cc(F)cc2c1COCO2 NWKUOCHFUQGXNS-UHFFFAOYSA-N 0.000 description 1
- ZEWGMOQWTWMZMZ-UHFFFAOYSA-N CCc1cccc(F)c1 Chemical compound CCc1cccc(F)c1 ZEWGMOQWTWMZMZ-UHFFFAOYSA-N 0.000 description 1
- VZJYRFYOYJFCMV-UHFFFAOYSA-N CN(CC1)CCC1(C=O)c1ccccc1 Chemical compound CN(CC1)CCC1(C=O)c1ccccc1 VZJYRFYOYJFCMV-UHFFFAOYSA-N 0.000 description 1
- DDRCHUGHUHZNKZ-UHFFFAOYSA-N O=C(C1CCNCC1)c1ccccc1 Chemical compound O=C(C1CCNCC1)c1ccccc1 DDRCHUGHUHZNKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14306578 | 2014-10-08 | ||
| EP14306578.7 | 2014-10-08 | ||
| PCT/EP2015/073141 WO2016055517A1 (en) | 2014-10-08 | 2015-10-07 | Novel aminopyridine compounds useful as inhibitors of protein prenylation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017536342A JP2017536342A (ja) | 2017-12-07 |
| JP2017536342A5 true JP2017536342A5 (enExample) | 2018-09-13 |
Family
ID=51799057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017518848A Pending JP2017536342A (ja) | 2014-10-08 | 2015-10-07 | タンパク質のプレニル化の阻害剤として有用な新規アミノピリジン化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10654838B2 (enExample) |
| EP (1) | EP3204380B1 (enExample) |
| JP (1) | JP2017536342A (enExample) |
| CN (1) | CN107001315A (enExample) |
| BR (1) | BR112017007178A2 (enExample) |
| DK (1) | DK3204380T3 (enExample) |
| ES (1) | ES2751623T3 (enExample) |
| IL (1) | IL251568A0 (enExample) |
| WO (1) | WO2016055517A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL283592B2 (en) | 2018-12-17 | 2025-08-01 | Vertex Pharma | Inhibitors of apol1 and methods of using same |
| EP4097083A1 (en) | 2020-01-29 | 2022-12-07 | Vertex Pharmaceuticals Incorporated | Inhibitors of apol1 and methods of using same |
| CN115209894B (zh) | 2020-03-06 | 2025-05-02 | 弗特克斯药品有限公司 | 治疗apol-1依赖性局灶节段性肾小球硬化的方法 |
| CN116157393A (zh) | 2020-06-12 | 2023-05-23 | 弗特克斯药品有限公司 | Apol1的抑制剂及其用途 |
| EP4165036A1 (en) | 2020-06-12 | 2023-04-19 | Vertex Pharmaceuticals Incorporated | Solid forms of apol1 inhibitor and using the same |
| UY39395A (es) | 2020-08-26 | 2022-03-31 | Vertex Pharma | Inhibidores de apol1 y métodos para usar los mismos |
| WO2023067550A1 (en) * | 2021-10-20 | 2023-04-27 | Yousef Najajreh | Allosteric inhibitor compounds for overcoming cancer resistance |
| US12612379B2 (en) | 2021-11-30 | 2026-04-28 | Vertex Pharmaceuticals Incorporated | Inhibitors of APOL1 and methods of using same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1110957A1 (en) * | 1999-12-24 | 2001-06-27 | Applied Research Systems ARS Holding N.V. | Benzazole derivatives and their use as JNK modulators |
| CA2524161C (en) | 2003-05-08 | 2013-01-15 | Applied Research Systems Ars Holding N.V. | Pyridinyl acetonitriles |
| JP2007522233A (ja) | 2004-02-11 | 2007-08-09 | アムジエン・インコーポレーテツド | バニロイド受容体リガンド及び治療におけるそれらの使用 |
| US20060281755A1 (en) | 2005-06-10 | 2006-12-14 | Baumann Christian A | Synergistic modulation of flt3 kinase using aminopyrimidines kinase modulators |
-
2015
- 2015-10-07 ES ES15775223T patent/ES2751623T3/es active Active
- 2015-10-07 CN CN201580062475.6A patent/CN107001315A/zh active Pending
- 2015-10-07 EP EP15775223.9A patent/EP3204380B1/en active Active
- 2015-10-07 DK DK15775223T patent/DK3204380T3/da active
- 2015-10-07 BR BR112017007178A patent/BR112017007178A2/pt not_active IP Right Cessation
- 2015-10-07 JP JP2017518848A patent/JP2017536342A/ja active Pending
- 2015-10-07 WO PCT/EP2015/073141 patent/WO2016055517A1/en not_active Ceased
- 2015-10-07 US US15/518,127 patent/US10654838B2/en active Active
-
2017
- 2017-04-05 IL IL251568A patent/IL251568A0/en unknown