JPWO2020214853A5 - - Google Patents
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- Publication number
- JPWO2020214853A5 JPWO2020214853A5 JP2021561778A JP2021561778A JPWO2020214853A5 JP WO2020214853 A5 JPWO2020214853 A5 JP WO2020214853A5 JP 2021561778 A JP2021561778 A JP 2021561778A JP 2021561778 A JP2021561778 A JP 2021561778A JP WO2020214853 A5 JPWO2020214853 A5 JP WO2020214853A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- hydroxy
- pharmaceutically acceptable
- cyclopenta
- oxy
- 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 amino, carboxy Chemical group 0.000 claims description 116
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
- 229940127084 other anti-cancer agent Drugs 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002147 L01XE04 - Sunitinib Substances 0.000 claims description 2
- 239000005511 L01XE05 - Sorafenib Substances 0.000 claims description 2
- 239000003798 L01XE11 - Pazopanib Substances 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 229960000397 bevacizumab Drugs 0.000 claims description 2
- ONIQOQHATWINJY-UHFFFAOYSA-N cabozantinib Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 ONIQOQHATWINJY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229960000639 pazopanib Drugs 0.000 claims description 2
- CUIHSIWYWATEQL-UHFFFAOYSA-N pazopanib Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CUIHSIWYWATEQL-UHFFFAOYSA-N 0.000 claims description 2
- 229960003787 sorafenib Drugs 0.000 claims description 2
- 229960001796 sunitinib Drugs 0.000 claims description 2
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 2
- 229950009791 durvalumab Drugs 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 201000010260 leiomyoma Diseases 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 208000006542 von Hippel-Lindau disease Diseases 0.000 claims 2
- RGJOJUGRHPQXGF-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1COC1)C2 RGJOJUGRHPQXGF-INIZCTEOSA-N 0.000 claims 1
- RGHYDLZMTYDBDT-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1H-pyrazol-5-yl)-7-pyrido[2,3-d]pyrimidinone Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=CNN=1 RGHYDLZMTYDBDT-UHFFFAOYSA-N 0.000 claims 1
- RHXHGRAEPCAFML-UHFFFAOYSA-N 7-cyclopentyl-n,n-dimethyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C2N(C3CCCC3)C(C(=O)N(C)C)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 RHXHGRAEPCAFML-UHFFFAOYSA-N 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- OODVFXIPGYPXET-UHFFFAOYSA-N C1(C)(CC2(C(C(C3=CC=C(OC4=CC(=CC(F)=C4)C#N)C1=C23)(F)F)(F)F)O)O Chemical compound C1(C)(CC2(C(C(C3=CC=C(OC4=CC(=CC(F)=C4)C#N)C1=C23)(F)F)(F)F)O)O OODVFXIPGYPXET-UHFFFAOYSA-N 0.000 claims 1
- TYVPHOZZGJZVKU-UHFFFAOYSA-N C1(C2=C(OC3=CC(=CC(F)=C3)C#N)C=CC=3C(F)(F)C(F)(F)C(O)(C1)C2=3)O Chemical compound C1(C2=C(OC3=CC(=CC(F)=C3)C#N)C=CC=3C(F)(F)C(F)(F)C(O)(C1)C2=3)O TYVPHOZZGJZVKU-UHFFFAOYSA-N 0.000 claims 1
- ANLMMGGKZQBCOT-UHFFFAOYSA-N C1(C2=C(OC3=CC(=CN=C3)F)C=CC=3C(F)(F)C(F)(C(O)(C1)C2=3)F)F Chemical compound C1(C2=C(OC3=CC(=CN=C3)F)C=CC=3C(F)(F)C(F)(C(O)(C1)C2=3)F)F ANLMMGGKZQBCOT-UHFFFAOYSA-N 0.000 claims 1
- NJPWONPTKHVKTD-UHFFFAOYSA-N C1(C2=C(OC3=CC(F)=CC(C#N)=C3)C=CC=3C(F)(F)C(F)(F)C(N)(C1)C2=3)F Chemical compound C1(C2=C(OC3=CC(F)=CC(C#N)=C3)C=CC=3C(F)(F)C(F)(F)C(N)(C1)C2=3)F NJPWONPTKHVKTD-UHFFFAOYSA-N 0.000 claims 1
- ZIEZRTWLAIDXDH-BLLLJJGKSA-N C1(OC2=CC(=CC(F)=C2)C#N)=CC=C2C(F)(F)C(F)(F)[C@]3(C[C@@H](C1=C23)F)O Chemical compound C1(OC2=CC(=CC(F)=C2)C#N)=CC=C2C(F)(F)C(F)(F)[C@]3(C[C@@H](C1=C23)F)O ZIEZRTWLAIDXDH-BLLLJJGKSA-N 0.000 claims 1
- ZIEZRTWLAIDXDH-MLGOLLRUSA-N C1(OC2=CC(=CC(F)=C2)C#N)=CC=C2C(F)(F)C(F)(F)[C@]3(C[C@@H](F)C1=C23)O Chemical compound C1(OC2=CC(=CC(F)=C2)C#N)=CC=C2C(F)(F)C(F)(F)[C@]3(C[C@@H](F)C1=C23)O ZIEZRTWLAIDXDH-MLGOLLRUSA-N 0.000 claims 1
- TYVPHOZZGJZVKU-MLGOLLRUSA-N C1[C@H](C2=C(C=CC3=C2[C@]1(C(C3(F)F)(F)F)O)OC4=CC(=CC(=C4)C#N)F)O Chemical compound C1[C@H](C2=C(C=CC3=C2[C@]1(C(C3(F)F)(F)F)O)OC4=CC(=CC(=C4)C#N)F)O TYVPHOZZGJZVKU-MLGOLLRUSA-N 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000030808 Clear cell renal carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 claims 1
- VDGWINQLIBYLHJ-UHFFFAOYSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)(C)F)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)(C)F)(C(C2(F)F)(F)F)O VDGWINQLIBYLHJ-UHFFFAOYSA-N 0.000 claims 1
- SFUJTROTJGXRCU-UHFFFAOYSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)=C)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)=C)(C(C2(F)F)(F)F)O SFUJTROTJGXRCU-UHFFFAOYSA-N 0.000 claims 1
- WTGKATVMPRYLQK-UHFFFAOYSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)=O)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)=O)(C(C2(F)F)(F)F)O WTGKATVMPRYLQK-UHFFFAOYSA-N 0.000 claims 1
- YRMGJHHSFVBPEQ-UHFFFAOYSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)C)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)C)(C(C2(F)F)(F)F)O YRMGJHHSFVBPEQ-UHFFFAOYSA-N 0.000 claims 1
- ZIEZRTWLAIDXDH-UHFFFAOYSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)F)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC(C1=3)F)(C(C2(F)F)(F)F)O ZIEZRTWLAIDXDH-UHFFFAOYSA-N 0.000 claims 1
- FJODMIGZWNEGQW-UHFFFAOYSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC4(CC4)C1=3)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CC4(CC4)C1=3)(C(C2(F)F)(F)F)O FJODMIGZWNEGQW-UHFFFAOYSA-N 0.000 claims 1
- XDKNYRDERWIFMY-UHFFFAOYSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CCC1=3)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3C(CCC1=3)(C(C2(F)F)(F)F)O XDKNYRDERWIFMY-UHFFFAOYSA-N 0.000 claims 1
- SFUJTROTJGXRCU-KRWDZBQOSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3[C@@](CC(C1=3)=C)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3[C@@](CC(C1=3)=C)(C(C2(F)F)(F)F)O SFUJTROTJGXRCU-KRWDZBQOSA-N 0.000 claims 1
- ZIEZRTWLAIDXDH-WBMJQRKESA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3[C@@](C[C@H](C1=3)F)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3[C@@](C[C@H](C1=3)F)(C(C2(F)F)(F)F)O ZIEZRTWLAIDXDH-WBMJQRKESA-N 0.000 claims 1
- WTGKATVMPRYLQK-MRXNPFEDSA-N FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3[C@](CC(C1=3)=O)(C(C2(F)F)(F)F)O Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=CC=C2C=3[C@](CC(C1=3)=O)(C(C2(F)F)(F)F)O WTGKATVMPRYLQK-MRXNPFEDSA-N 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 239000002118 L01XE12 - Vandetanib Substances 0.000 claims 1
- 208000018142 Leiomyosarcoma Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000033383 Neuroendocrine tumor of pancreas Diseases 0.000 claims 1
- 206010061534 Oesophageal squamous cell carcinoma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010067517 Pancreatic neuroendocrine tumour Diseases 0.000 claims 1
- 206010061332 Paraganglion neoplasm Diseases 0.000 claims 1
- 208000007913 Pituitary Neoplasms Diseases 0.000 claims 1
- 208000031306 Rare hereditary hemochromatosis Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- 208000016624 Retinal neoplasm Diseases 0.000 claims 1
- 206010041329 Somatostatinoma Diseases 0.000 claims 1
- 208000036765 Squamous cell carcinoma of the esophagus Diseases 0.000 claims 1
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 1
- LNFBAYSBVQBKFR-UHFFFAOYSA-N [7-(6-aminopyridin-3-yl)-3,5-dihydro-2h-1,4-benzoxazepin-4-yl]-(3-fluoro-2-methyl-4-methylsulfonylphenyl)methanone Chemical compound CC1=C(F)C(S(C)(=O)=O)=CC=C1C(=O)N1CC2=CC(C=3C=NC(N)=CC=3)=CC=C2OCC1 LNFBAYSBVQBKFR-UHFFFAOYSA-N 0.000 claims 1
- 229950001573 abemaciclib Drugs 0.000 claims 1
- 229960002833 aflibercept Drugs 0.000 claims 1
- 108010081667 aflibercept Proteins 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 1
- 229960003852 atezolizumab Drugs 0.000 claims 1
- 229960003005 axitinib Drugs 0.000 claims 1
- RITAVMQDGBJQJZ-FMIVXFBMSA-N axitinib Chemical compound CNC(=O)C1=CC=CC=C1SC1=CC=C(C(\C=C\C=2N=CC=CC=2)=NN2)C2=C1 RITAVMQDGBJQJZ-FMIVXFBMSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 206010073251 clear cell renal cell carcinoma Diseases 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- JOGKUKXHTYWRGZ-UHFFFAOYSA-N dactolisib Chemical compound O=C1N(C)C2=CN=C3C=CC(C=4C=C5C=CC=CC5=NC=4)=CC3=C2N1C1=CC=C(C(C)(C)C#N)C=C1 JOGKUKXHTYWRGZ-UHFFFAOYSA-N 0.000 claims 1
- 229950006418 dactolisib Drugs 0.000 claims 1
- 208000007276 esophageal squamous cell carcinoma Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229960005167 everolimus Drugs 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
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- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 201000002222 hemangioblastoma Diseases 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 229960003784 lenvatinib Drugs 0.000 claims 1
- WOSKHXYHFSIKNG-UHFFFAOYSA-N lenvatinib Chemical compound C=12C=C(C(N)=O)C(OC)=CC2=NC=CC=1OC(C=C1Cl)=CC=C1NC(=O)NC1CC1 WOSKHXYHFSIKNG-UHFFFAOYSA-N 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 claims 1
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- UZWDCWONPYILKI-UHFFFAOYSA-N n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]-5-fluoro-4-(7-fluoro-2-methyl-3-propan-2-ylbenzimidazol-5-yl)pyrimidin-2-amine Chemical compound C1CN(CC)CCN1CC(C=N1)=CC=C1NC1=NC=C(F)C(C=2C=C3N(C(C)C)C(C)=NC3=C(F)C=2)=N1 UZWDCWONPYILKI-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000011330 nonpapillary renal cell carcinoma Diseases 0.000 claims 1
- 229960004390 palbociclib Drugs 0.000 claims 1
- AHJRHEGDXFFMBM-UHFFFAOYSA-N palbociclib Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 AHJRHEGDXFFMBM-UHFFFAOYSA-N 0.000 claims 1
- 208000021010 pancreatic neuroendocrine tumor Diseases 0.000 claims 1
- 208000007312 paraganglioma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000028591 pheochromocytoma Diseases 0.000 claims 1
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- 201000008933 retinal cancer Diseases 0.000 claims 1
- 229950003687 ribociclib Drugs 0.000 claims 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims 1
- 229960000235 temsirolimus Drugs 0.000 claims 1
- QFJCIRLUMZQUOT-UHFFFAOYSA-N temsirolimus Natural products C1CC(O)C(OC)CC1CC(C)C1OC(=O)C2CCCCN2C(=O)C(=O)C(O)(O2)C(C)CCC2CC(OC)C(C)=CC=CC=CC(C)CC(C)C(=O)C(OC)C(O)C(C)=CC(C)C(=O)C1 QFJCIRLUMZQUOT-UHFFFAOYSA-N 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 201000007954 uterine fibroid Diseases 0.000 claims 1
- 229960000241 vandetanib Drugs 0.000 claims 1
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| CA3235013A1 (en) * | 2021-10-18 | 2023-04-27 | Jing Lu | Hypoxia inducible factor-2(alpha) inhibitors for the treatment of bladder cancer |
| WO2023070483A1 (en) | 2021-10-29 | 2023-05-04 | Nikang Therapeutics, Inc. | PROCESSES OF MAKING 3-FLUORO-5- ( ( (1R, 2S, 2aS) -1, 2, 3, 3, 4, 4-HEXAFLUORO-2A-HYDROXY-2, 2A, 3, 4-TETRAHYDRO-1H-CYCLOPENTA [CD] INDEN-7-YL) -OXY) -BENZONITRILE AND POLYMORPHS THEREOF |
| WO2024240240A1 (zh) * | 2023-05-24 | 2024-11-28 | 江苏恩华药业股份有限公司 | 一种咪唑衍生物、中间体、制备方法及其应用 |
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| WO2025230942A1 (en) | 2024-05-03 | 2025-11-06 | Nikang Therapeutics, Inc. | Pharmaceutical compositions of 3-fluoro-5-(((ls,2ar)-l,3,3,4,4-pentafluoro-2a-hydroxy-2,2a,3,4-tetrahydro-1h-cyclopenta[cd]inden-7-yl)oxy)-benzonitrile |
| WO2025235034A1 (en) * | 2024-05-04 | 2025-11-13 | Nikang Therapeutics, Inc. | 3-fluoro-5-(((ls,2ar)-1,3,3,4, 4-pentafluoro-2a-hydroxy-2,2a, 3,4-tetrahydro-lh-cyclopenta[cd]inden-7- yl)oxy)- benzonitrile dosing regimen for use in the treatment of cancer |
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2020
- 2020-04-16 IL IL287258A patent/IL287258B2/en unknown
- 2020-04-16 KR KR1020217037203A patent/KR20210154191A/ko active Pending
- 2020-04-16 SG SG11202111118YA patent/SG11202111118YA/en unknown
- 2020-04-16 CA CA3136650A patent/CA3136650A1/en active Pending
- 2020-04-16 US US16/851,018 patent/US20200361855A1/en not_active Abandoned
- 2020-04-16 MX MX2021012549A patent/MX2021012549A/es unknown
- 2020-04-16 JP JP2021561778A patent/JP7581236B2/ja active Active
- 2020-04-16 WO PCT/US2020/028579 patent/WO2020214853A1/en not_active Ceased
- 2020-04-16 EP EP20733066.3A patent/EP3956299A1/en active Pending
- 2020-04-16 AU AU2020260130A patent/AU2020260130C1/en active Active
- 2020-04-16 UA UAA202105642A patent/UA128792C2/uk unknown
- 2020-04-16 CN CN202411099450.0A patent/CN118993938A/zh active Pending
- 2020-04-16 CN CN202411099453.4A patent/CN118993939A/zh active Pending
- 2020-04-16 CN CN202080027716.4A patent/CN113874350B/zh active Active
- 2020-04-17 TW TW109113096A patent/TWI871313B/zh active
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2021
- 2021-03-30 US US17/218,129 patent/US11267782B2/en active Active
- 2021-07-15 US US17/377,356 patent/US20210347729A1/en not_active Abandoned
- 2021-10-26 ZA ZA2021/08270A patent/ZA202108270B/en unknown
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2022
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2023
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2025
- 2025-07-15 US US19/270,361 patent/US20250340508A1/en active Pending
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