CA2803467A1 - New aminopyrazoloquinazolines - Google Patents
New aminopyrazoloquinazolines Download PDFInfo
- Publication number
- CA2803467A1 CA2803467A1 CA2803467A CA2803467A CA2803467A1 CA 2803467 A1 CA2803467 A1 CA 2803467A1 CA 2803467 A CA2803467 A CA 2803467A CA 2803467 A CA2803467 A CA 2803467A CA 2803467 A1 CA2803467 A1 CA 2803467A1
- Authority
- CA
- Canada
- Prior art keywords
- denotes
- 6alkyl
- 4alkyl
- independently selected
- hydrogen
- 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.)
- Abandoned
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- SUOYKOLHSZCPPT-UHFFFAOYSA-N C1=CC2=NN=CC2=C2NC(N)=NC=C21 Chemical class C1=CC2=NN=CC2=C2NC(N)=NC=C21 SUOYKOLHSZCPPT-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 6
- -1 1-aza-bicyclo[2.2.2]octyl Chemical group 0.000 claims description 226
- 238000000034 method Methods 0.000 claims description 190
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 239000001257 hydrogen Substances 0.000 claims description 76
- 125000000623 heterocyclic group Chemical group 0.000 claims description 69
- 229910052736 halogen Inorganic materials 0.000 claims description 67
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 206010028980 Neoplasm Diseases 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 239000013543 active substance Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 201000011510 cancer Diseases 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 10
- 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 10
- 230000002265 prevention Effects 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 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 8
- 239000000969 carrier Substances 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 7
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
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- ARWPUMUNJQFGGQ-HNNXBMFYSA-N (5s)-n-[1-(2-methoxyethyl)pyrazol-3-yl]-5,8-dimethyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(N(C)N=C4C[C@H](C)C3=CN=2)C=2C=CC=CC=2)=N1 ARWPUMUNJQFGGQ-HNNXBMFYSA-N 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
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- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 231100000433 cytotoxic Toxicity 0.000 claims description 3
- 230000001472 cytotoxic effect Effects 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- DVKCGYZMPSNIFZ-UHFFFAOYSA-N 1-[4-[4-[[9-[4-(difluoromethoxy)phenyl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-yl]amino]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1N1N=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC(OC(F)F)=CC=2)=C1 DVKCGYZMPSNIFZ-UHFFFAOYSA-N 0.000 claims description 2
- QXNWQMXMRDSICW-UHFFFAOYSA-N 8-methyl-9-phenyl-n-[1-(2-pyrrolidin-1-ylethyl)pyrazol-3-yl]-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound N1=C2C3=C(C=4C=CC=CC=4)N(C)N=C3CCC2=CN=C1NC(=N1)C=CN1CCN1CCCC1 QXNWQMXMRDSICW-UHFFFAOYSA-N 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims description 2
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- 230000004054 inflammatory process Effects 0.000 claims description 2
- ARWPUMUNJQFGGQ-UHFFFAOYSA-N n-[1-(2-methoxyethyl)pyrazol-3-yl]-5,8-dimethyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CC(C)C3=CN=2)C=2C=CC=CC=2)=N1 ARWPUMUNJQFGGQ-UHFFFAOYSA-N 0.000 claims description 2
- LWQUHXAZSAMKHS-UHFFFAOYSA-N n-[1-(2-methoxyethyl)pyrazol-3-yl]-8-methyl-9-[(3-methylphenyl)methyl]-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(CC=5C=C(C)C=CC=5)N(C)N=C4CCC3=CN=2)=N1 LWQUHXAZSAMKHS-UHFFFAOYSA-N 0.000 claims description 2
- DRJYVDSVFZZZEI-UHFFFAOYSA-N n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-5,8-dimethyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound N=1C=C2C(C)CC3=NN(C)C(C=4C=CC=CC=4)=C3C2=NC=1NC=1C=CN(CCN(C)C)N=1 DRJYVDSVFZZZEI-UHFFFAOYSA-N 0.000 claims description 2
- QKFHSJDLWFPOMT-UHFFFAOYSA-N n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-8-methyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CN(C)CCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC=CC=2)=N1 QKFHSJDLWFPOMT-UHFFFAOYSA-N 0.000 claims description 2
- LOFUVYKJPBSYDP-UHFFFAOYSA-N n-[1-[2-[2-methoxyethyl(methyl)amino]ethyl]pyrazol-3-yl]-8-methyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN(C)CCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC=CC=2)=N1 LOFUVYKJPBSYDP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 42
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 4
- SXALUXHTCNSKEQ-UHFFFAOYSA-N 9-[4-(difluoromethoxy)phenyl]-n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CN(C)CCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC(OC(F)F)=CC=2)=N1 SXALUXHTCNSKEQ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Landscapes
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- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (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)
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| TW201343648A (zh) * | 2012-01-23 | 2013-11-01 | Boehringer Ingelheim Int | 作為ｉｇｆ－１ｒ／ｉｒ抑制劑之新５，８－二氫－６ｈ－吡唑并［３，４－ｈ］喹唑啉 |
| US9376437B2 (en) | 2013-03-13 | 2016-06-28 | Oncoceutics, Inc | 7-benzyl-4-(2-methylbenzyl)-2,4,6,7,8,9-hexahydroimidazo[1,2-a]pyrido[3,4-e]pyrimidin-5(1H)-one, salts thereof and methods of using the same in combination therapy |
| PT3068401T (pt) * | 2013-11-15 | 2019-06-04 | Oncoceutics Inc | 7-benzil-4-(2-metilbenzil)-2,4,6,7,7,8,9-hexaidroimidazo[1,2- a]pirido[3,4-e]pirimidin-5(1h)-ona, seus sais e métodos de uso |
| PT3805222T (pt) | 2015-01-30 | 2025-03-10 | Oncoceutics Inc | Derivados de 7-benzil-4-(2-metilbenzil)-2,4,6,7,8,9-hexa-hidroimidazo[1,2-a]pirido[3,4-e]pirimidin-5(1h)-ona, seus sais e sua utilização em terapia |
| US10414769B2 (en) | 2015-05-13 | 2019-09-17 | Boehringer Ingelheim International Gmbh | 5,8-dimethyl-9-phenyl-5,8-dihydro-6H-pyrazolo[3,4-h]quinazolin-2-yl)-(1H-pyrazol-3-yl)-amines as IGF-1R/IR inhibitors |
| JP6905069B2 (ja) * | 2016-11-11 | 2021-07-21 | 上海海雁醫藥科技有限公司 | ピリジルアミノ置換へテロ三環式化合物並びにその製造方法及び医薬用途 |
| DK3632904T3 (da) * | 2017-05-26 | 2022-07-25 | Jiangsu Atom Bioscience And Pharmaceutical Co Ltd | URAT1-inhibitorer til at fremme urinsyreudskillelse |
| CN107383019B (zh) * | 2017-07-28 | 2019-10-15 | 江苏艾凡生物医药有限公司 | 吡唑并[4,3-h]喹唑啉类化合物及其用途 |
| WO2019206154A1 (zh) | 2018-04-24 | 2019-10-31 | 上海海雁医药科技有限公司 | Cdk4/6抑制剂及其药学上可接受的盐和多晶型物及其应用 |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| EP3873431A1 (en) | 2018-11-02 | 2021-09-08 | Fount Bio, Inc. | Crosslinked materials |
| US20220098214A1 (en) * | 2019-01-30 | 2022-03-31 | Yale University | Compounds, compositions, and methods for treating fibrosis |
| US11384083B2 (en) | 2019-02-15 | 2022-07-12 | Incyte Corporation | Substituted spiro[cyclopropane-1,5′-pyrrolo[2,3-d]pyrimidin]-6′(7′h)-ones as CDK2 inhibitors |
| WO2020180959A1 (en) | 2019-03-05 | 2020-09-10 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| US20220144822A1 (en) * | 2019-03-07 | 2022-05-12 | BioNTech SE | Process for the preparation of a substituted imidazoquinoline |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| JP7650817B2 (ja) * | 2019-04-19 | 2025-03-25 | ファウント バイオ， インコーポレイテッド | 皮膚内への活性剤の送達および保持 |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| WO2020223469A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | N-(1-(methylsulfonyl)piperidin-4-yl)-4,5-di hydro-1h-imidazo[4,5-h]quinazolin-8-amine derivatives and related compounds as cyclin-dependent kinase 2 (cdk2) inhibitors for treating cancer |
| AU2020328025A1 (en) | 2019-08-14 | 2022-03-03 | Incyte Corporation | Imidazolyl pyrimidinylamine compounds as CDK2 inhibitors |
| JOP20220087A1 (ar) | 2019-10-11 | 2023-01-30 | Incyte Corp | أمينات ثنائية الحلقة كمثبطات لـ cdk2 |
| IL298760A (en) | 2020-06-05 | 2023-02-01 | Kinnate Biopharma Inc | Fibroblast growth factor receptor kinase inhibitors |
| CN111960974A (zh) * | 2020-08-28 | 2020-11-20 | 山东潍坊润丰化工股份有限公司 | 一种烯草酮中间体的合成方法 |
| WO2022166725A1 (zh) * | 2021-02-08 | 2022-08-11 | 南京明德新药研发有限公司 | 5，6-二氢噻吩并[3，4-h]喹唑啉类化合物 |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
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| ATE222892T1 (de) * | 1995-10-02 | 2002-09-15 | Hoffmann La Roche | Pyrimidinderivate als 5ht2c-rezeptorantagonisten |
| BRPI0410563B8 (pt) | 2003-05-22 | 2021-05-25 | Nerviano Medical Sciences Srl | compostos de pirazol-quinazolina, seus processos de preparação e composições farmacêuticas |
| CN1897950A (zh) * | 2003-10-14 | 2007-01-17 | 惠氏公司 | 稠合芳基和杂芳基衍生物及其使用方法 |
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| TW201217380A (en) | 2012-05-01 |
| EA201201661A1 (ru) | 2013-07-30 |
| WO2012010704A1 (en) | 2012-01-26 |
| MA34389B1 (fr) | 2013-07-03 |
| JP5991974B2 (ja) | 2016-09-14 |
| UY33526A (es) | 2012-02-29 |
| AU2011281504A1 (en) | 2013-01-10 |
| US20120238542A1 (en) | 2012-09-20 |
| BR112013000107A2 (pt) | 2016-05-17 |
| AR082850A1 (es) | 2013-01-16 |
| KR20130132394A (ko) | 2013-12-04 |
| EP2595987A1 (en) | 2013-05-29 |
| JP2013532652A (ja) | 2013-08-19 |
| PH12013500152A1 (en) | 2013-02-18 |
| CO6670575A2 (es) | 2013-05-15 |
| MX2013000821A (es) | 2013-05-30 |
| CL2012003745A1 (es) | 2013-05-31 |
| SG187548A1 (en) | 2013-03-28 |
| AP2012006640A0 (en) | 2012-12-31 |
| ECSP13012448A (es) | 2013-03-28 |
| EP2595987B1 (en) | 2018-04-18 |
| GEP20156289B (en) | 2015-05-25 |
| US8735386B2 (en) | 2014-05-27 |
| PE20131143A1 (es) | 2013-10-23 |
| CN103097388A (zh) | 2013-05-08 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20121220 |
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| FZDE | Discontinued |
Effective date: 20160722 |