KR20170068585A - 야누스 키나제 억제제로서의 에틸 N-Boc 피페리디닐 피라졸로 피리돈 - Google Patents
야누스 키나제 억제제로서의 에틸 N-Boc 피페리디닐 피라졸로 피리돈 Download PDFInfo
- Publication number
- KR20170068585A KR20170068585A KR1020177013258A KR20177013258A KR20170068585A KR 20170068585 A KR20170068585 A KR 20170068585A KR 1020177013258 A KR1020177013258 A KR 1020177013258A KR 20177013258 A KR20177013258 A KR 20177013258A KR 20170068585 A KR20170068585 A KR 20170068585A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridin
- carboxylate
- oxo
- alkyl
- piperidine
- 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.)
- Withdrawn
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims description 15
- 229940122245 Janus kinase inhibitor Drugs 0.000 title abstract description 4
- BQXMJSXVUDFLCQ-UHFFFAOYSA-N N1(CCCCC1)C1=NC2=C(C=C1)N=NC2=O Chemical class N1(CCCCC1)C1=NC2=C(C=C1)N=NC2=O BQXMJSXVUDFLCQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 238000000034 method Methods 0.000 claims abstract description 37
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- 208000006673 asthma Diseases 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 19
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- -1 1- C 6 haloalkyl Chemical group 0.000 claims description 293
- 125000000217 alkyl group Chemical group 0.000 claims description 183
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 98
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 71
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 69
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
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- 150000003839 salts Chemical class 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
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- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- DTRJMDAVHUVYAE-HSZRJFAPSA-N tert-butyl 4-[3-[4-[(1R)-1-(tert-butylamino)-2,2,2-trifluoroethyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C(C)(C)(C)N[C@@H](C(F)(F)F)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC DTRJMDAVHUVYAE-HSZRJFAPSA-N 0.000 claims description 2
- DTRJMDAVHUVYAE-QHCPKHFHSA-N tert-butyl 4-[3-[4-[(1S)-1-(tert-butylamino)-2,2,2-trifluoroethyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C(C)(C)(C)N[C@H](C(F)(F)F)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC DTRJMDAVHUVYAE-QHCPKHFHSA-N 0.000 claims description 2
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 claims 2
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- 230000000306 recurrent effect Effects 0.000 claims 1
- 208000037765 diseases and disorders Diseases 0.000 abstract description 3
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- 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
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- 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
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- 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
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- 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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- A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
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- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
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- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
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- Medicinal Chemistry (AREA)
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- Pulmonology (AREA)
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- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports 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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2014/089139 WO2016061751A1 (en) | 2014-10-22 | 2014-10-22 | Ethyl n-boc piperidinyl pyrazolo pyridones as janus kinase inhibitors |
| CNPCT/CN2014/089139 | 2014-10-22 | ||
| PCT/US2015/056541 WO2016064935A1 (en) | 2014-10-22 | 2015-10-21 | Ethyl n-boc piperidinyl pyrazolo pyridones as janus kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20170068585A true KR20170068585A (ko) | 2017-06-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177013258A Withdrawn KR20170068585A (ko) | 2014-10-22 | 2015-10-21 | 야누스 키나제 억제제로서의 에틸 N-Boc 피페리디닐 피라졸로 피리돈 |
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Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7034942B2 (ja) | 2016-05-05 | 2022-03-14 | エフ．ホフマン－ラ ロシュ アーゲー | ピラゾール誘導体、その組成物及び治療的使用 |
| CN106749081B (zh) * | 2016-11-21 | 2019-06-25 | 浙江嘉圣生物医药有限公司 | 一种(s)-(4-溴-2-甲苯)(3-甲基吗啉)甲酮的制备方法 |
| JP2020504711A (ja) | 2016-12-21 | 2020-02-13 | バイオセリックス， インコーポレイテッド | タンパク質を標的とすることにおいて使用するための、チエノピロール誘導体、その組成物、方法、および使用 |
| WO2018169777A1 (en) | 2017-03-14 | 2018-09-20 | Biotheryx, Inc. | Compounds targeting proteins, compositions, methods, and uses thereof |
| LT3728215T (lt) * | 2017-12-22 | 2021-12-10 | Siegfried Ag | Raceminio nikotino gavimo etilnikotinato reakcijoje su n-vinilpirolidonu, dalyvaujant natrio etanoliatui arba kalio etanoliatui, arba jų mišiniams, būdas, vykdant sintezę viename inde |
| CN111819181A (zh) * | 2018-05-10 | 2020-10-23 | 罗欣药业(上海)有限公司 | 苯并七元杂环类化合物、其制备方法、药物组合物及应用 |
| CN112752755A (zh) * | 2018-09-27 | 2021-05-04 | 豪夫迈·罗氏有限公司 | 用于治疗自身免疫性疾病的杂环基化合物 |
| CN114901659A (zh) | 2019-11-26 | 2022-08-12 | 施万生物制药研发Ip有限责任公司 | 作为jak抑制剂的稠合嘧啶吡啶酮化合物 |
| US12606556B2 (en) * | 2020-02-26 | 2026-04-21 | Beone Medicines I Gmbh | TYK-2 inhibitor |
| UY39569A (es) * | 2020-12-17 | 2022-07-29 | Astrazeneca Ab | N-(2-(4-cianotiazolidin-3-il)-2-oxoetil)- quinolin-4-carboxamidas |
| CN114644633B (zh) * | 2020-12-18 | 2026-02-03 | 北京诺诚健华医药科技有限公司 | 杂环类jak抑制剂 |
| CN114939349B (zh) * | 2022-05-03 | 2023-08-01 | 北京工业大学 | 一种用于气体分离的金属-有机空穴配合物混合基质膜的制备 |
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| UA111854C2 (uk) * | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| MX2015013419A (es) * | 2013-03-19 | 2016-07-19 | Merck Sharp & Dohme | Cianoetilpirazolo piridonas aciclicas como inhibidores de janus quinasa. |
| WO2014146249A1 (en) * | 2013-03-19 | 2014-09-25 | Merck Sharp & Dohme Corp. | Geminally substituted cyanoethylpyrazolo pyridones as janus kinase inhibitors |
| EP2976338B1 (en) * | 2013-03-19 | 2018-01-03 | Merck Sharp & Dohme Corp. | N-(2-cyano heterocyclyl)pyrazolo pyridones as janus kinase inhibitors |
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- 2015-10-21 JP JP2017521567A patent/JP2017531672A/ja not_active Withdrawn
- 2015-10-21 RU RU2017117248A patent/RU2017117248A/ru not_active Application Discontinuation
- 2015-10-21 BR BR112017008103A patent/BR112017008103A2/pt not_active Application Discontinuation
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| CN107106547A (zh) | 2017-08-29 |
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| JP2017531672A (ja) | 2017-10-26 |
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| EP3209296B1 (en) | 2019-07-10 |
| BR112017008103A2 (pt) | 2018-02-20 |
| US10072025B2 (en) | 2018-09-11 |
| EP3209296A4 (en) | 2018-04-11 |
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| US20170240567A1 (en) | 2017-08-24 |
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| AU2015336035A1 (en) | 2017-04-20 |
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