JP2014527997A5 - - Google Patents
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- JP2014527997A5 JP2014527997A5 JP2014532500A JP2014532500A JP2014527997A5 JP 2014527997 A5 JP2014527997 A5 JP 2014527997A5 JP 2014532500 A JP2014532500 A JP 2014532500A JP 2014532500 A JP2014532500 A JP 2014532500A JP 2014527997 A5 JP2014527997 A5 JP 2014527997A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- bis
- amino
- cyclopropylmethyl
- trifluoromethyl
- 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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- -1 1H-pyrazol-3-yl Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 20
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 16
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims description 12
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 102000015779 HDL Lipoproteins Human genes 0.000 claims description 8
- 108010010234 HDL Lipoproteins Proteins 0.000 claims description 8
- 102000007330 LDL Lipoproteins Human genes 0.000 claims description 8
- 108010007622 LDL Lipoproteins Proteins 0.000 claims description 8
- 235000012000 cholesterol Nutrition 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- UGJOSZKALSQWAA-UHFFFAOYSA-N 1-[2-[[6-[bis(cyclopropylmethyl)amino]-1,3-dimethylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]ethanone Chemical compound N1=CC(C(=O)C)=CN=C1N(CC=1C(=NC=2N(C)N=C(C)C=2C=1)N(CC1CC1)CC1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UGJOSZKALSQWAA-UHFFFAOYSA-N 0.000 claims description 2
- JJJVBMWJSLUPPC-UHFFFAOYSA-N 1-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]ethanone Chemical compound N1=CC(C(=O)C)=CN=C1N(CC=1C(=NC=2N(N=C(C)C=2C=1)C(C)(C)C)N(CC1CC1)CC1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JJJVBMWJSLUPPC-UHFFFAOYSA-N 0.000 claims description 2
- ZLFJEQSWPOUTQE-UHFFFAOYSA-N 1-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]pyrrolidin-2-one Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)N1C(CCC1)=O)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 ZLFJEQSWPOUTQE-UHFFFAOYSA-N 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 2
- QWIUVXSCUCYBRI-UHFFFAOYSA-N 3-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]-1,3-oxazolidin-2-one Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)N1C(OCC1)=O)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 QWIUVXSCUCYBRI-UHFFFAOYSA-N 0.000 claims description 2
- YSGNECRJOZOTJS-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-morpholin-4-ylpyrimidin-2-yl)amino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)N1CCOCC1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 YSGNECRJOZOTJS-UHFFFAOYSA-N 0.000 claims description 2
- OZJFYIOMAVRCBY-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-morpholin-4-ylpyrimidin-2-yl)amino]methyl]-n,n-bis(cyclopropylmethyl)-1,3-dimethylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)N1CCOCC1)CC=1C=C2C(C)=NN(C)C2=NC=1N(CC1CC1)CC1CC1 OZJFYIOMAVRCBY-UHFFFAOYSA-N 0.000 claims description 2
- DNQNMROHXBGNDH-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-[5-(1-methylpyrazol-3-yl)pyrimidin-2-yl]amino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)C1=NN(C)C=C1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 DNQNMROHXBGNDH-UHFFFAOYSA-N 0.000 claims description 2
- MQHAGAOYVLUYIK-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-[5-(1h-pyrazol-5-yl)pyrimidin-2-yl]amino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)C1=NNC=C1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 MQHAGAOYVLUYIK-UHFFFAOYSA-N 0.000 claims description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 2
- MJBWDEQAUQTVKK-IAGOWNOFSA-N aflatoxin M1 Chemical compound C=1([C@]2(O)C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O MJBWDEQAUQTVKK-IAGOWNOFSA-N 0.000 claims description 2
- VKKOLUVFLBZUIU-UHFFFAOYSA-N ethyl 2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-4-methylpyrimidine-5-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CN=C1N(CC=1C(=NC=2N(N=C(C)C=2C=1)C(C)(C)C)N(CC1CC1)CC1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VKKOLUVFLBZUIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- SUIVDHPMVHDPTR-UHFFFAOYSA-N n-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]-2-methylpropanamide Chemical compound N1=CC(NC(=O)C(C)C)=CN=C1N(CC=1C(=NC=2N(N=C(C)C=2C=1)C(C)(C)C)N(CC1CC1)CC1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SUIVDHPMVHDPTR-UHFFFAOYSA-N 0.000 claims description 2
- DIQWGVJRNIEHKI-UHFFFAOYSA-N n-[2-[[6-[bis(cyclopropylmethyl)amino]-1-tert-butyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]methyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-yl]cyclopropanecarboxamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(NC(=O)C2CC2)=CN=1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 DIQWGVJRNIEHKI-UHFFFAOYSA-N 0.000 claims description 2
- XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 claims description 2
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 2
- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 24
- 238000002560 therapeutic procedure Methods 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- WNSQSFXJJUQBBA-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-[5-(1,2-oxazol-3-yl)pyrimidin-2-yl]amino]methyl]-n,n-bis(cyclopropylmethyl)-1,3-dimethylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(=CN=1)C1=NOC=C1)CC=1C=C2C(C)=NN(C)C2=NC=1N(CC1CC1)CC1CC1 WNSQSFXJJUQBBA-UHFFFAOYSA-N 0.000 claims 1
- MZGWSZLPJKOQOK-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methylamino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CNCC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 MZGWSZLPJKOQOK-UHFFFAOYSA-N 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000000034 method Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- NNHRTHSVDJBLSL-UHFFFAOYSA-N 5-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-bromopyrimidin-2-yl)amino]methyl]-1-tert-butyl-n,n-bis(cyclopropylmethyl)-3-methylpyrazolo[3,4-b]pyridin-6-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C=1N=CC(Br)=CN=1)CC=1C=C2C(C)=NN(C(C)(C)C)C2=NC=1N(CC1CC1)CC1CC1 NNHRTHSVDJBLSL-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)Cc1ccc(CN(*)Cc2cc(c(*)n[n]3O*)c3nc2N(*)*)cc1 Chemical compound CC(C)Cc1ccc(CN(*)Cc2cc(c(*)n[n]3O*)c3nc2N(*)*)cc1 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3337/CHE/2011 | 2011-09-27 | ||
| IN3337CH2011 | 2011-09-27 | ||
| US201161558262P | 2011-11-10 | 2011-11-10 | |
| US61/558,262 | 2011-11-10 | ||
| PCT/IB2012/002435 WO2013046045A1 (en) | 2011-09-27 | 2012-09-27 | 5 - benzylaminomethyl - 6 - aminopyrazolo [3, 4 -b] pyridine derivatives as cholesteryl ester -transfer protein (cetp) inhibitors useful for the treatment of atherosclerosis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014527997A JP2014527997A (ja) | 2014-10-23 |
| JP2014527997A5 true JP2014527997A5 (OSRAM) | 2015-10-29 |
| JP6140168B2 JP6140168B2 (ja) | 2017-05-31 |
Family
ID=47994351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014532500A Expired - Fee Related JP6140168B2 (ja) | 2011-09-27 | 2012-09-27 | アテローム性動脈硬化症の処置のために有用なコレステリルエステル転送タンパク質（ｃｅｔｐ）インヒビターとしての５−ベンジルアミノメチル−６−アミノピラゾロ［３，４−ｂ］ピリジン誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9000007B2 (OSRAM) |
| EP (1) | EP2760864B1 (OSRAM) |
| JP (1) | JP6140168B2 (OSRAM) |
| KR (1) | KR101803866B1 (OSRAM) |
| CN (1) | CN103958511A (OSRAM) |
| AU (1) | AU2012313971B2 (OSRAM) |
| CA (1) | CA2850022C (OSRAM) |
| HK (1) | HK1197238A1 (OSRAM) |
| IN (1) | IN2014CN02290A (OSRAM) |
| MX (1) | MX352074B (OSRAM) |
| WO (1) | WO2013046045A1 (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3081864B2 (ja) | 1996-01-08 | 2000-08-28 | 三井化学株式会社 | 金属製接続部材付き合成樹脂製管継手及びその製造方法 |
| JPWO2014017569A1 (ja) * | 2012-07-26 | 2016-07-11 | 興和株式会社 | 血中ｌｄｌを低下させるための医薬 |
| JP2015054838A (ja) * | 2013-09-12 | 2015-03-23 | 興和株式会社 | 血中ｌｄｌコレステロールを低下させる医薬 |
| KR20160096612A (ko) * | 2013-12-13 | 2016-08-16 | 다이이찌 산쿄 가부시키가이샤 | 5-하이드록시-4-(트리플루오로메틸)피라졸로피리딘 유도체 |
| CN109956940A (zh) * | 2019-05-14 | 2019-07-02 | 上海贤鼎生物科技有限公司 | 一种帕博昔布中间体氰基化反应制备杂芳基氰化物的方法 |
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-
2012
- 2012-09-27 AU AU2012313971A patent/AU2012313971B2/en not_active Ceased
- 2012-09-27 KR KR1020147009133A patent/KR101803866B1/ko not_active Expired - Fee Related
- 2012-09-27 JP JP2014532500A patent/JP6140168B2/ja not_active Expired - Fee Related
- 2012-09-27 CA CA2850022A patent/CA2850022C/en not_active Expired - Fee Related
- 2012-09-27 EP EP12816102.3A patent/EP2760864B1/en not_active Not-in-force
- 2012-09-27 IN IN2290CHN2014 patent/IN2014CN02290A/en unknown
- 2012-09-27 US US14/347,519 patent/US9000007B2/en not_active Expired - Fee Related
- 2012-09-27 HK HK14110754.9A patent/HK1197238A1/xx unknown
- 2012-09-27 MX MX2014003660A patent/MX352074B/es active IP Right Grant
- 2012-09-27 CN CN201280057987.XA patent/CN103958511A/zh active Pending
- 2012-09-27 WO PCT/IB2012/002435 patent/WO2013046045A1/en not_active Ceased
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