CN101945867A - 作为细胞周期抑制剂的稠合吡啶、嘧啶和三嗪化合物 - Google Patents
作为细胞周期抑制剂的稠合吡啶、嘧啶和三嗪化合物 Download PDFInfo
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- CN101945867A CN101945867A CN2008801270640A CN200880127064A CN101945867A CN 101945867 A CN101945867 A CN 101945867A CN 2008801270640 A CN2008801270640 A CN 2008801270640A CN 200880127064 A CN200880127064 A CN 200880127064A CN 101945867 A CN101945867 A CN 101945867A
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- alkylidene group
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 32
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 16
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 9
- 150000003918 triazines Chemical class 0.000 title abstract 2
- 229940123587 Cell cycle inhibitor Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 378
- 238000000034 method Methods 0.000 claims abstract description 58
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 31
- 201000011510 cancer Diseases 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- -1 dihydropyridine ketone Chemical class 0.000 claims description 212
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 150000003839 salts Chemical class 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 38
- 125000000304 alkynyl group Chemical group 0.000 claims description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 239000003153 chemical reaction reagent Substances 0.000 claims description 34
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 34
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 32
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 150000003851 azoles Chemical class 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 11
- 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 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002460 imidazoles Chemical class 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000005936 piperidyl group Chemical group 0.000 claims description 8
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 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
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
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- 108010050904 Interferons Proteins 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
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- 229940079322 interferon Drugs 0.000 claims description 4
- 150000003233 pyrroles Chemical class 0.000 claims description 4
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- 230000001399 anti-metabolic effect Effects 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims description 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 2
- 150000004881 2H-pyrans Chemical class 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 150000004867 thiadiazoles Chemical class 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 abstract description 8
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 abstract description 8
- 230000001404 mediated effect Effects 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 397
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 279
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 258
- 239000000243 solution Substances 0.000 description 183
- 239000002585 base Substances 0.000 description 164
- 238000005160 1H NMR spectroscopy Methods 0.000 description 145
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 138
- 239000007787 solid Substances 0.000 description 123
- 238000006243 chemical reaction Methods 0.000 description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 100
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 95
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 85
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 64
- 239000000203 mixture Substances 0.000 description 63
- 238000001035 drying Methods 0.000 description 59
- 238000010828 elution Methods 0.000 description 58
- YVVMIGRXQRPSIY-UHFFFAOYSA-N 7-deaza-2-aminopurine Chemical compound N1C(N)=NC=C2C=CN=C21 YVVMIGRXQRPSIY-UHFFFAOYSA-N 0.000 description 56
- 150000001335 aliphatic alkanes Chemical class 0.000 description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 55
- 238000003756 stirring Methods 0.000 description 55
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 52
- 238000010898 silica gel chromatography Methods 0.000 description 48
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 44
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 43
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
- 150000001721 carbon Chemical group 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
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- 239000002253 acid Substances 0.000 description 32
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 239000003921 oil Substances 0.000 description 29
- 235000019198 oils Nutrition 0.000 description 29
- 238000010926 purge Methods 0.000 description 29
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 29
- 125000003545 alkoxy group Chemical group 0.000 description 27
- 229910052786 argon Inorganic materials 0.000 description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
- 229920006395 saturated elastomer Polymers 0.000 description 26
- 239000011734 sodium Substances 0.000 description 25
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
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- 238000005481 NMR spectroscopy Methods 0.000 description 23
- HAKVNWBUOCSHTR-UHFFFAOYSA-N (9,9-dimethylxanthen-1-yl)-diphenylphosphane Chemical compound C=12C(C)(C)C3=CC=CC=C3OC2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 HAKVNWBUOCSHTR-UHFFFAOYSA-N 0.000 description 22
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
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- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 22
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Classifications
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- C07D471/12—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 three hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- A61K31/535—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 oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- A61K31/5386—1,4-Oxazines, e.g. morpholine spiro-condensed or forming part of bridged ring systems
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| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| JP2022519772A (ja) | 2019-02-15 | 2022-03-24 | インサイト・コーポレイション | サイクリン依存性キナーゼ2バイオマーカー及びその使用 |
| US11472791B2 (en) | 2019-03-05 | 2022-10-18 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as CDK2 inhibitors |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| US11447494B2 (en) | 2019-05-01 | 2022-09-20 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| CN114364675A (zh) | 2019-05-05 | 2022-04-15 | 上海齐鲁锐格医药研发有限公司 | Cdk抑制剂 |
| EP3738593A1 (en) | 2019-05-14 | 2020-11-18 | Amgen, Inc | Dosing of kras inhibitor for treatment of cancers |
| CA3225293A1 (en) | 2019-05-21 | 2020-11-26 | Amgen Inc. | Solid state forms |
| TW202112767A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之胺基吡啶衍生物 |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| AU2020319875A1 (en) | 2019-08-01 | 2022-02-17 | Incyte Corporation | A dosing regimen for an IDO inhibitor |
| BR112022002698A2 (pt) | 2019-08-14 | 2022-07-19 | Incyte Corp | Compostos de imidazolil pirimidinilamina como inibidores de cdk2 |
| US12122767B2 (en) | 2019-10-01 | 2024-10-22 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| AU2020364007A1 (en) | 2019-10-11 | 2022-04-28 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| WO2021076602A1 (en) | 2019-10-14 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076655A1 (en) | 2019-10-15 | 2021-04-22 | Amgen Inc. | Combination therapy of kras inhibitor and shp2 inhibitor for treatment of cancers |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| KR20220131900A (ko) | 2019-12-04 | 2022-09-29 | 인사이트 코포레이션 | Fgfr 억제제의 유도체 |
| JP7720840B2 (ja) | 2019-12-04 | 2025-08-08 | インサイト・コーポレイション | Fgfr阻害剤としての三環式複素環 |
| US20230028414A1 (en) | 2019-12-16 | 2023-01-26 | Amgen Inc. | Dosing regimen of kras g12c inhibitor |
| WO2021133886A1 (en) | 2019-12-23 | 2021-07-01 | Accutar Biotechnology | Combinations of estrogen receptor degraders and cyclin-dependent kinase inhibitors for treating cancer |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| JP2023516441A (ja) | 2020-03-06 | 2023-04-19 | インサイト・コーポレイション | Axl/mer阻害剤及びpd-1/pd-l1阻害剤を含む併用療法 |
| IL297165A (en) | 2020-04-16 | 2022-12-01 | Incyte Corp | Soysag tricyclic CRS inhibitors |
| US11739102B2 (en) | 2020-05-13 | 2023-08-29 | Incyte Corporation | Fused pyrimidine compounds as KRAS inhibitors |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| US11999752B2 (en) | 2020-08-28 | 2024-06-04 | Incyte Corporation | Vinyl imidazole compounds as inhibitors of KRAS |
| US11767320B2 (en) | 2020-10-02 | 2023-09-26 | Incyte Corporation | Bicyclic dione compounds as inhibitors of KRAS |
| WO2022155941A1 (en) | 2021-01-25 | 2022-07-28 | Qilu Regor Therapeutics Inc. | Cdk2 inhibitors |
| PE20231939A1 (es) * | 2021-03-01 | 2023-12-05 | Orion Corp | Proceso para la preparacion de un inhibidor de cyp11a1 y sus intermedios |
| WO2022206888A1 (en) | 2021-03-31 | 2022-10-06 | Qilu Regor Therapeutics Inc. | Cdk2 inhibitors and use thereof |
| CA3215903A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| WO2022261159A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| EP4352059A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US12441727B2 (en) | 2021-07-07 | 2025-10-14 | Incyte Corporation | Tricyclic compounds as inhibitors of KRAS |
| JP2024529347A (ja) | 2021-07-14 | 2024-08-06 | インサイト・コーポレイション | Krasの阻害剤としての三環式化合物 |
| CA3229855A1 (en) | 2021-08-31 | 2023-03-09 | Incyte Corporation | Naphthyridine compounds as inhibitors of kras |
| WO2023049697A1 (en) | 2021-09-21 | 2023-03-30 | Incyte Corporation | Hetero-tricyclic compounds as inhibitors of kras |
| WO2023056421A1 (en) | 2021-10-01 | 2023-04-06 | Incyte Corporation | Pyrazoloquinoline kras inhibitors |
| KR20240101561A (ko) | 2021-10-14 | 2024-07-02 | 인사이트 코포레이션 | Kras의 저해제로서의 퀴놀린 화합물 |
| CA3239205A1 (en) | 2021-11-22 | 2023-05-25 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a kras inhibitor |
| US20230203010A1 (en) | 2021-12-03 | 2023-06-29 | Incyte Corporation | Bicyclic amine cdk12 inhibitors |
| US12084453B2 (en) | 2021-12-10 | 2024-09-10 | Incyte Corporation | Bicyclic amines as CDK12 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| AU2022418585A1 (en) | 2021-12-22 | 2024-07-11 | Incyte Corporation | Salts and solid forms of an fgfr inhibitor and processes of preparing thereof |
| TW202341982A (zh) | 2021-12-24 | 2023-11-01 | 大陸商上海齊魯銳格醫藥研發有限公司 | Cdk2抑制劑及其用途 |
| WO2023168686A1 (en) | 2022-03-11 | 2023-09-14 | Qilu Regor Therapeutics Inc. | Substituted cyclopentanes as cdk2 inhibitors |
| CA3253781A1 (en) | 2022-03-07 | 2023-09-14 | Incyte Corp | SOLIDS, SALTS AND PROCESSES FOR PREPARING A CDK2 INHIBITOR |
| US20250353842A1 (en) | 2022-06-22 | 2025-11-20 | Incyte Corporation | Bicyclic amine cdk12 inhibitors |
| WO2024015731A1 (en) | 2022-07-11 | 2024-01-18 | Incyte Corporation | Fused tricyclic compounds as inhibitors of kras g12v mutants |
| WO2024220645A1 (en) | 2023-04-18 | 2024-10-24 | Incyte Corporation | 2-azabicyclo[2.2.1]heptane kras inhibitors |
| WO2024220532A1 (en) | 2023-04-18 | 2024-10-24 | Incyte Corporation | Pyrrolidine kras inhibitors |
| WO2024254245A1 (en) | 2023-06-09 | 2024-12-12 | Incyte Corporation | Bicyclic amines as cdk2 inhibitors |
| US20250163079A1 (en) | 2023-11-01 | 2025-05-22 | Incyte Corporation | Kras inhibitors |
| WO2025129002A1 (en) | 2023-12-13 | 2025-06-19 | Incyte Corporation | Bicyclooctane kras inhibitors |
| CN120398832B (zh) * | 2025-06-30 | 2025-09-23 | 浙江九洲药业股份有限公司 | 一种瑞博西尼中间体及其制备方法 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1168290A (en) * | 1964-08-27 | 1969-10-22 | Allen & Hanburys Ltd | Novel Heterocyclic Compounds |
| IT1153216B (it) | 1981-10-16 | 1987-01-14 | Schering Ag | Procedimento per la preparazione di composti cianoeterociclici |
| US6498163B1 (en) | 1997-02-05 | 2002-12-24 | Warner-Lambert Company | Pyrido[2,3-D]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation |
| KR20020075805A (ko) | 2000-03-06 | 2002-10-05 | 워너-램버트 캄파니 | 5-알킬피리도[2,3-d]피리미딘 타이로신 카이나제 억제제 |
| MXPA02007981A (es) | 2000-03-15 | 2004-04-05 | Aventis Pharma Gmbh | Beta-carbolinas sustituidas con actividad que inhibe la ikb-cinasa. |
| GB0007371D0 (en) | 2000-03-28 | 2000-05-17 | Astrazeneca Uk Ltd | Chemical compounds |
| EP1295878B1 (en) | 2000-06-30 | 2004-09-15 | Banyu Pharmaceutical Co., Ltd. | Pyrazinone derivatives |
| KR20060111716A (ko) | 2002-01-22 | 2006-10-27 | 워너-램버트 캄파니 엘엘씨 | 2-(피리딘-2-일아미노)-피리도[2,3-d]피리미딘-7-온 |
| WO2003062246A1 (en) | 2002-01-22 | 2003-07-31 | Warner-Lambert Company Llc | 2-thia-1,6,8-triaza-naphtalene-2,2-dioxides as cdk inhibitors |
| US20030199525A1 (en) | 2002-03-21 | 2003-10-23 | Hirst Gavin C. | Kinase inhibitors |
| US7563798B2 (en) | 2002-09-04 | 2009-07-21 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| MXPA05007503A (es) | 2003-01-17 | 2005-09-21 | Warner Lambert Co | Heterociclicos 2-aminopiridina sustituidos como inhibidores de proliferacion celular. |
| US7482354B2 (en) | 2003-05-22 | 2009-01-27 | Nerviano Medical Sciences S.R.L. | Pyrazolo-quinazoline derivatives, process for their preparation and their use as kinase inhibitors |
| PL1648889T3 (pl) | 2003-07-11 | 2009-03-31 | Warner Lambert Co | Sól izetionian selektywnego inhibitora CDK4 |
| EP1678149A2 (en) | 2003-10-31 | 2006-07-12 | Neurogen Corporation | 4-amino(aza)quinoline derivatives as capsaicin receptor agonists |
| GB0329214D0 (en) | 2003-12-17 | 2004-01-21 | Glaxo Group Ltd | Novel compounds |
| GB0403606D0 (en) | 2004-02-18 | 2004-03-24 | Novartis Ag | Organic compounds |
| BRPI0507852A (pt) | 2004-02-18 | 2007-07-10 | Warner Lambert Co | 2-(piridin-3-ilamino)-pirido[2,3-d]pirimidin-7-onas |
| WO2005094830A1 (en) | 2004-03-30 | 2005-10-13 | Pfizer Products Inc. | Combinations of signal transduction inhibitors |
| CA2566158A1 (en) | 2004-05-14 | 2005-11-24 | Abbott Laboratories | Kinase inhibitors as therapeutic agents |
| CA2569277A1 (en) | 2004-06-04 | 2005-12-15 | Pfizer Products Inc. | Method for treating abnormal cell growth |
| EP1781293A1 (en) | 2004-06-04 | 2007-05-09 | Amphora Discovery Corporation | Quinoline- and isoquinoline-based compounds exhibiting atp-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| WO2006021547A1 (de) | 2004-08-26 | 2006-03-02 | Boehringer Ingelheim International Gmbh | Pteridinone als plk (polo like kinase) inhibitoren |
| WO2006042102A2 (en) | 2004-10-05 | 2006-04-20 | Neurogen Corporation | Pyrrolo-pyridine, pyrrolo-pyrimidine and related heterocyclic compounds |
| WO2006044425A2 (en) | 2004-10-13 | 2006-04-27 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| US20060142312A1 (en) | 2004-12-23 | 2006-06-29 | Pfizer Inc | C6-aryl and heteroaryl substituted pyrido[2,3-D] pyrimidin-7-ones |
| US7947695B2 (en) | 2005-01-14 | 2011-05-24 | Janssen Pharmaceutica Nv | 5-membered annelated heterocyclic pyrimidines as kinase inhibitors |
| WO2006077428A1 (en) | 2005-01-21 | 2006-07-27 | Astex Therapeutics Limited | Pharmaceutical compounds |
| JP2008542433A (ja) * | 2005-06-09 | 2008-11-27 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | CDK−1インヒビターとしてのα−カルボリン |
| MX2008002365A (es) | 2005-08-19 | 2008-03-18 | Schering Corp | Antagonistas triciclicos fusionados del receptor glutamato metabotropico 1 como agentes terapeuticos. |
| WO2007024680A1 (en) | 2005-08-22 | 2007-03-01 | Amgen Inc. | Pyrazolopyridine and pyrazolopyrimidine compounds useful as kinase enzymes modulators |
| BRPI0616985B1 (pt) | 2005-10-06 | 2021-10-26 | Merck Sharp & Dohme Corp. | Composto de pirazolo[1,5-a]pirimidina, e, uso de um composto |
| ATE542823T1 (de) | 2006-04-12 | 2012-02-15 | Vertex Pharma | 4,5-dihydro-ä1,2,4ütriazoloä4,3-füpteridine als plk1-proteinkinasehemmer zur behandlung proliferativer erkrankungen |
| WO2007125405A2 (en) | 2006-05-01 | 2007-11-08 | Pfizer Products Inc. | Substituted 2-amino-fused heterocyclic compounds |
| US20090142337A1 (en) | 2006-05-08 | 2009-06-04 | Astex Therapeutics Limited | Pharmaceutical Combinations of Diazole Derivatives for Cancer Treatment |
| US7893058B2 (en) | 2006-05-15 | 2011-02-22 | Janssen Pharmaceutica Nv | Imidazolopyrazine compounds useful for the treatment of degenerative and inflammatory diseases |
| US20070270362A1 (en) | 2006-05-18 | 2007-11-22 | The University Of Washington | Methods and compositions for prevention or treatment of inflammatory-related diseases and disorders |
| TWI398252B (zh) * | 2006-05-26 | 2013-06-11 | Novartis Ag | 吡咯并嘧啶化合物及其用途 |
| EP2035436B1 (en) | 2006-06-26 | 2011-05-25 | UCB Pharma S.A. | Fused thiazole derivatives as kinase inhibitors |
| KR20090052385A (ko) | 2006-09-08 | 2009-05-25 | 화이자 프로덕츠 인크. | 2-(피리딘-2-일아미노)-피리도[2,3-d]피리미딘-7-온의합성 |
| JP2010513317A (ja) | 2006-12-14 | 2010-04-30 | パナシー ファーマシューティカルズ インコーポレーティッド | サイクリン依存性キナーゼの阻害による神経保護方法 |
| US20100298314A1 (en) | 2006-12-20 | 2010-11-25 | Schering Corporation | Novel jnk inhibitors |
| US20080234262A1 (en) | 2007-03-21 | 2008-09-25 | Wyeth | Pyrazolopyrimidine analogs and their use as mtor kinase and pi3 kinase inhibitors |
| US20090030005A1 (en) | 2007-07-19 | 2009-01-29 | Amgen Inc. | Combinations for the treatment of cancer |
| US7982035B2 (en) | 2007-08-27 | 2011-07-19 | Duquesne University Of The Holy Spirit | Tricyclic compounds having antimitotic and/or antitumor activity and methods of use thereof |
| US7960400B2 (en) | 2007-08-27 | 2011-06-14 | Duquesne University Of The Holy Ghost | Tricyclic compounds having cytostatic and/or cytotoxic activity and methods of use thereof |
| JP2011503084A (ja) | 2007-11-07 | 2011-01-27 | シェーリング コーポレイション | 新規の細胞周期チェックポイント調節剤およびこれらの調節剤とチェックポイント阻害剤との併用 |
| US9259399B2 (en) | 2007-11-07 | 2016-02-16 | Cornell University | Targeting CDK4 and CDK6 in cancer therapy |
| CA2709202C (en) * | 2007-12-19 | 2013-04-23 | Amgen Inc. | Fused pyridine, pyrimidine and triazine compounds as cell cycle inhibitors |
| US20110014191A1 (en) | 2007-12-28 | 2011-01-20 | Ipsogen | Breast cancer expression profiling |
| AR070127A1 (es) | 2008-01-11 | 2010-03-17 | Novartis Ag | Pirrolo - pirimidinas y pirrolo -piridinas |
| KR20160035613A (ko) * | 2011-03-23 | 2016-03-31 | 암젠 인크 | Cdk 4/6 및 flt3의 융합된 트리사이클릭 이중 저해제 |
-
2008
- 2008-12-18 CA CA2709202A patent/CA2709202C/en not_active Expired - Fee Related
- 2008-12-18 NZ NZ586069A patent/NZ586069A/en not_active IP Right Cessation
- 2008-12-18 AU AU2008343932A patent/AU2008343932B2/en not_active Ceased
- 2008-12-18 WO PCT/US2008/013849 patent/WO2009085185A1/en not_active Ceased
- 2008-12-18 CN CN2008801270640A patent/CN101945867A/zh active Pending
- 2008-12-18 BR BRPI0821209A patent/BRPI0821209A2/pt not_active IP Right Cessation
- 2008-12-18 MX MX2010006457A patent/MX2010006457A/es not_active Application Discontinuation
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- 2008-12-18 US US12/808,621 patent/US8841312B2/en active Active
- 2008-12-18 EA EA201001030A patent/EA201001030A1/ru unknown
- 2008-12-18 JP JP2010539487A patent/JP5537439B2/ja not_active Expired - Fee Related
- 2008-12-18 KR KR1020107015936A patent/KR20100095020A/ko not_active Withdrawn
-
2010
- 2010-05-27 TN TN2010000236A patent/TN2010000236A1/fr unknown
- 2010-05-30 IL IL206070A patent/IL206070A0/en unknown
- 2010-07-02 ZA ZA2010/04668A patent/ZA201004668B/en unknown
- 2010-07-14 MA MA33013A patent/MA32014B1/fr unknown
- 2010-07-19 CO CO10087751A patent/CO6290648A2/es not_active Application Discontinuation
- 2010-07-19 CR CR11573A patent/CR11573A/es not_active Application Discontinuation
-
2011
- 2011-11-30 ZA ZA2011/08779A patent/ZA201108779B/en unknown
-
2014
- 2014-08-07 US US14/453,842 patent/US8980903B2/en active Active
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| CN114634521A (zh) * | 2020-12-15 | 2022-06-17 | 首药控股(北京)股份有限公司 | Dna-pk选择性抑制剂及其制备方法和用途 |
| WO2022228399A1 (zh) * | 2021-04-27 | 2022-11-03 | 山东轩竹医药科技有限公司 | 三并环类usp1抑制剂及其用途 |
| CN117355532A (zh) * | 2021-04-27 | 2024-01-05 | 山东轩竹医药科技有限公司 | 三并环类usp1抑制剂及其用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100095020A (ko) | 2010-08-27 |
| CO6290648A2 (es) | 2011-06-20 |
| TN2010000236A1 (en) | 2011-11-11 |
| AU2008343932A1 (en) | 2009-07-09 |
| WO2009085185A1 (en) | 2009-07-09 |
| AU2008343932B2 (en) | 2013-08-15 |
| EA201001030A1 (ru) | 2011-02-28 |
| US20110142796A1 (en) | 2011-06-16 |
| JP2011507849A (ja) | 2011-03-10 |
| MX2010006457A (es) | 2010-07-05 |
| MA32014B1 (fr) | 2011-01-03 |
| CA2709202A1 (en) | 2009-07-09 |
| US8841312B2 (en) | 2014-09-23 |
| EP2231656A1 (en) | 2010-09-29 |
| BRPI0821209A2 (pt) | 2019-09-24 |
| JP5537439B2 (ja) | 2014-07-02 |
| ZA201004668B (en) | 2012-03-28 |
| US20140350244A1 (en) | 2014-11-27 |
| NZ586069A (en) | 2012-05-25 |
| CA2709202C (en) | 2013-04-23 |
| US8980903B2 (en) | 2015-03-17 |
| ZA201108779B (en) | 2013-02-27 |
| IL206070A0 (en) | 2010-11-30 |
| CR11573A (es) | 2010-10-05 |
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