CA2802641C - Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators - Google Patents
Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators Download PDFInfo
- Publication number
- CA2802641C CA2802641C CA2802641A CA2802641A CA2802641C CA 2802641 C CA2802641 C CA 2802641C CA 2802641 A CA2802641 A CA 2802641A CA 2802641 A CA2802641 A CA 2802641A CA 2802641 C CA2802641 C CA 2802641C
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- phenyl
- chloro
- pyrimidine
- carboxylic acid
- 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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- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 title description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 230000001404 mediated effect Effects 0.000 claims abstract description 14
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims abstract description 13
- 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims abstract description 12
- -1 hydroxy, amino Chemical group 0.000 claims description 556
- 239000000203 mixture Substances 0.000 claims description 286
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 144
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 125000003386 piperidinyl group Chemical group 0.000 claims description 67
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 66
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 50
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
- 201000010099 disease Diseases 0.000 claims description 37
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 30
- PUWCNAHJTYTHKV-UHFFFAOYSA-N thieno[3,2-d]pyrimidine-7-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=CSC2=C1 PUWCNAHJTYTHKV-UHFFFAOYSA-N 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000004193 piperazinyl group Chemical group 0.000 claims description 27
- 125000003725 azepanyl group Chemical group 0.000 claims description 25
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 23
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 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 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 206010003246 arthritis Diseases 0.000 claims description 9
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 230000002757 inflammatory effect Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 208000023504 respiratory system disease Diseases 0.000 claims description 7
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 208000019693 Lung disease Diseases 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- PCHWCLBVSAKTKO-UHFFFAOYSA-N 3-(2-amino-4-chlorophenoxy)propan-1-ol Chemical compound NC1=CC(Cl)=CC=C1OCCCO PCHWCLBVSAKTKO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- FIKOGHBRNAAIAL-UHFFFAOYSA-N 4-(2-amino-4-chlorophenoxy)cyclohexan-1-ol Chemical compound NC1=CC(Cl)=CC=C1OC1CCC(O)CC1 FIKOGHBRNAAIAL-UHFFFAOYSA-N 0.000 claims description 4
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 4
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- 206010006482 Bronchospasm Diseases 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- 230000001363 autoimmune Effects 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 230000000414 obstructive effect Effects 0.000 claims description 4
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- OKAAFIKHHROVHN-UHFFFAOYSA-N 6-bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(Br)C=NC2=C(C(=O)O)C=NN21 OKAAFIKHHROVHN-UHFFFAOYSA-N 0.000 claims description 2
- INIORSSITPVKJU-UHFFFAOYSA-N [3-(2-amino-4-chlorophenoxy)cyclopentyl]methanol Chemical compound NC1=CC(Cl)=CC=C1OC1CC(CO)CC1 INIORSSITPVKJU-UHFFFAOYSA-N 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- RKBDEYDDNCNVHV-UHFFFAOYSA-N [1-(2-amino-4-chlorophenyl)piperidin-4-yl]methanol Chemical compound NC1=CC(Cl)=CC=C1N1CCC(CO)CC1 RKBDEYDDNCNVHV-UHFFFAOYSA-N 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- UCIHGIGRCAGUSD-UHFFFAOYSA-N 2-[4-(aminomethyl)piperidin-1-yl]-5-chloroaniline Chemical compound C1CC(CN)CCN1C1=CC=C(Cl)C=C1N UCIHGIGRCAGUSD-UHFFFAOYSA-N 0.000 claims 3
- BFOQYOCNAFPILH-UHFFFAOYSA-N 5-chloro-2-piperidin-1-ylaniline Chemical compound NC1=CC(Cl)=CC=C1N1CCCCC1 BFOQYOCNAFPILH-UHFFFAOYSA-N 0.000 claims 2
- QVTMXACHOQRSAX-UHFFFAOYSA-N (3-amino-4-piperidin-1-ylphenyl)methanol Chemical compound NC1=CC(CO)=CC=C1N1CCCCC1 QVTMXACHOQRSAX-UHFFFAOYSA-N 0.000 claims 1
- CZBXTHMRCUGAHE-UHFFFAOYSA-N 1-(2-amino-4-chlorophenyl)piperidin-4-amine Chemical compound NC1CCN(CC1)c1ccc(Cl)cc1N CZBXTHMRCUGAHE-UHFFFAOYSA-N 0.000 claims 1
- LTHFHPRRYKAMNS-UHFFFAOYSA-N 1-(2-amino-4-chlorophenyl)piperidin-4-ol Chemical compound NC1=CC(Cl)=CC=C1N1CCC(O)CC1 LTHFHPRRYKAMNS-UHFFFAOYSA-N 0.000 claims 1
- CPOALQAOZYXUPJ-UHFFFAOYSA-N 1-(2-amino-4-chlorophenyl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC=C(Cl)C=C1N CPOALQAOZYXUPJ-UHFFFAOYSA-N 0.000 claims 1
- FZGRDZYPVPZTIW-UHFFFAOYSA-N 1-[1-(2-amino-4-chlorophenyl)pyrrolidin-3-yl]ethanol Chemical compound C1C(C(O)C)CCN1C1=CC=C(Cl)C=C1N FZGRDZYPVPZTIW-UHFFFAOYSA-N 0.000 claims 1
- ZBRZYIHPBZPHJY-UHFFFAOYSA-N 2-(2-amino-4-chlorophenoxy)ethanol Chemical compound NC1=CC(Cl)=CC=C1OCCO ZBRZYIHPBZPHJY-UHFFFAOYSA-N 0.000 claims 1
- FRWWOTCTTUUMFK-UHFFFAOYSA-N 2-[4-(1-aminoethyl)piperidin-1-yl]-5-chloroaniline Chemical compound C1CC(C(N)C)CCN1C1=CC=C(Cl)C=C1N FRWWOTCTTUUMFK-UHFFFAOYSA-N 0.000 claims 1
- VDVPKUCZXPCBJE-UHFFFAOYSA-N 3-(2-amino-4-chlorophenoxy)cyclopentan-1-ol Chemical compound NC1=CC(Cl)=CC=C1OC1CC(O)CC1 VDVPKUCZXPCBJE-UHFFFAOYSA-N 0.000 claims 1
- YXQUGGJCURTCJR-UHFFFAOYSA-N 5-chloro-2-[4-(methylaminomethyl)piperidin-1-yl]aniline Chemical compound CNCC1CCN(CC1)c1ccc(Cl)cc1N YXQUGGJCURTCJR-UHFFFAOYSA-N 0.000 claims 1
- GZAFTZKFOXXEHE-UHFFFAOYSA-N 5-chloro-2-[4-[(dimethylamino)methyl]piperidin-1-yl]aniline Chemical compound C1CC(CN(C)C)CCN1C1=CC=C(Cl)C=C1N GZAFTZKFOXXEHE-UHFFFAOYSA-N 0.000 claims 1
- MWDWRKMVOHRBHW-UHFFFAOYSA-N 5-chloro-2-pyrrolidin-1-ylaniline Chemical compound NC1=CC(Cl)=CC=C1N1CCCC1 MWDWRKMVOHRBHW-UHFFFAOYSA-N 0.000 claims 1
- VYZUBHRSGQAROM-UHFFFAOYSA-N 5-fluoro-2-methoxyaniline Chemical compound COC1=CC=C(F)C=C1N VYZUBHRSGQAROM-UHFFFAOYSA-N 0.000 claims 1
- RPZAHRQFGVSMOO-UHFFFAOYSA-N [4-(2-amino-4-chlorophenyl)phenyl]methanol Chemical compound NC1=CC(Cl)=CC=C1C1=CC=C(CO)C=C1 RPZAHRQFGVSMOO-UHFFFAOYSA-N 0.000 claims 1
- JVOWUKRCRGTNNZ-UHFFFAOYSA-N n-(7-methoxyquinolin-6-yl)-2-(propan-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N1=C(NC(C)C)N=C2C(C(=O)NC3=CC4=CC=CN=C4C=C3OC)=CSC2=C1 JVOWUKRCRGTNNZ-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 306
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 304
- 230000015572 biosynthetic process Effects 0.000 description 276
- 238000003786 synthesis reaction Methods 0.000 description 275
- 239000007787 solid Substances 0.000 description 186
- 230000002829 reductive effect Effects 0.000 description 181
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 148
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 139
- 238000000034 method Methods 0.000 description 123
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 122
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- 239000000243 solution Substances 0.000 description 110
- 239000000843 powder Substances 0.000 description 106
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 103
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 88
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- HNYVPKNVKSTVJO-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=NC2=C(C(=O)O)C=NN21 HNYVPKNVKSTVJO-UHFFFAOYSA-N 0.000 description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- 125000000217 alkyl group Chemical group 0.000 description 60
- 239000012267 brine Substances 0.000 description 59
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 239000000284 extract Substances 0.000 description 47
- 239000012044 organic layer Substances 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
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- KCQYKVZIORIDPZ-UHFFFAOYSA-N pyrazolo[1,5-c]pyrimidine-3-carboxylic acid Chemical compound C1=NC=CC2=C(C(=O)O)C=NN21 KCQYKVZIORIDPZ-UHFFFAOYSA-N 0.000 description 39
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Classifications
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- C07—ORGANIC CHEMISTRY
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Applications Claiming Priority (5)
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| US36385510P | 2010-07-13 | 2010-07-13 | |
| US61/363,855 | 2010-07-13 | ||
| US201161485145P | 2011-05-12 | 2011-05-12 | |
| US61/485,145 | 2011-05-12 | ||
| PCT/EP2011/061598 WO2012007375A1 (en) | 2010-07-13 | 2011-07-08 | Pyrazolo [1, 5a] pyrimidine and thieno [3, 2b] pyrimidine derivatives as irak4 modulators |
Publications (2)
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| CA2802641A1 CA2802641A1 (en) | 2012-01-19 |
| CA2802641C true CA2802641C (en) | 2019-03-12 |
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| KR101483215B1 (ko) * | 2010-01-29 | 2015-01-16 | 한미약품 주식회사 | 단백질 키나아제 저해활성을 갖는 비시클릭 헤테로아릴 유도체 |
| MX358682B (es) * | 2010-07-13 | 2018-08-31 | Hoffmann La Roche | Derivados de pirazolo [1,5a]pirimidina y de tieno[3,2b] pirimidina como moduladores de la cinasa asociada al receptor de la interleucina 4 (irak4). |
| EP2663312B1 (en) | 2011-01-10 | 2017-10-11 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| EP2688872A4 (en) * | 2011-03-22 | 2014-08-27 | Merck Sharp & Dohme | AMIDOPYRAZOLHEMMER OF INTERLEUKIN RECEPTOR-MEDIATED KINASES |
| JP2014517079A (ja) | 2011-06-22 | 2014-07-17 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| UA109614C2 (uk) * | 2011-12-30 | 2015-09-10 | ПОХІДНІ ТІЄНО[3,2-d]ПІРИМІДИНУ, ЩО МАЮТЬ ІНГІБУЮЧУ АКТИВНІСТЬ ВІДНОСНО ПРОТЕЇНКІНАЗ | |
| HK1209632A1 (en) * | 2012-01-10 | 2016-04-08 | 林伯士艾瑞斯公司 | Irak inhibitors and uses thereof |
| CN104159904B (zh) * | 2012-01-10 | 2016-12-14 | 霍夫曼-拉罗奇有限公司 | 噻吩并嘧啶化合物 |
| WO2014003483A1 (en) * | 2012-06-29 | 2014-01-03 | Hanmi Pharm. Co., Ltd. | Fused pyrimidine derivatives having inhibitory activity on fms kinases |
| RU2015104123A (ru) | 2012-07-10 | 2016-08-27 | Арес Трейдинг С.А. | Производные пиримидинпиразолила |
| WO2014011911A2 (en) * | 2012-07-11 | 2014-01-16 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| CN104902959A (zh) | 2012-07-11 | 2015-09-09 | 林伯士艾瑞斯公司 | Irak抑制剂和其用途 |
| EP2872144A4 (en) | 2012-07-11 | 2015-12-02 | Nimbus Iris Inc | IRAQ INHIBITOR AND USES THEREOF |
| EP3418281B1 (en) | 2012-12-07 | 2020-09-30 | Vertex Pharmaceuticals Inc. | Pyrazolo[1,5-a]pyrimidines useful as inhibitors of atr kinase for the treatment of cancer diseases |
| BR112015014034A2 (pt) | 2013-01-10 | 2017-07-11 | Nimbus Iris Inc | inibidores de irak e usos dos mesmos |
| WO2014110574A1 (en) | 2013-01-14 | 2014-07-17 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as pim kinase inhibitors |
| UA121098C2 (uk) | 2013-01-15 | 2020-04-10 | Інсайт Холдинґс Корпорейшн | Тіазолкарбоксаміди і піридинкарбоксаміди, які використовуються як інгібітори рім-кінази |
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| MX340490B (es) | 2016-07-11 |
| AR082154A1 (es) | 2012-11-14 |
| MX2013000390A (es) | 2013-03-08 |
| RU2013103539A (ru) | 2014-08-20 |
| US10023589B2 (en) | 2018-07-17 |
| CN102985426B (zh) | 2015-10-07 |
| BR112013000868A2 (pt) | 2016-05-17 |
| HK1183029A1 (zh) | 2013-12-13 |
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