JP7241542B2 - テトラヒドロイソキノリン エストロゲン受容体モジュレーター及びその使用 - Google Patents

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Publication number

JP7241542B2

JP7241542B2 JP2018552850A JP2018552850A JP7241542B2 JP 7241542 B2 JP7241542 B2 JP 7241542B2 JP 2018552850 A JP2018552850 A JP 2018552850A JP 2018552850 A JP2018552850 A JP 2018552850A JP 7241542 B2 JP7241542 B2 JP 7241542B2

Authority

JP

Japan

Prior art keywords

compound

phenyl

azetidin

ethoxy

fluoromethyl

Prior art date

2016-04-08

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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• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title description 5
• 239000002834 estrogen receptor modulator Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 381
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 147
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 140
• -1 1-methylazetidin-3-yl Chemical group 0.000 claims description 133
• 206010028980 Neoplasm Diseases 0.000 claims description 100
• 238000000034 method Methods 0.000 claims description 70
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
• 239000003814 drug Substances 0.000 claims description 55
• 201000011510 cancer Diseases 0.000 claims description 53
• 108010038795 estrogen receptors Proteins 0.000 claims description 46
• 201000010099 disease Diseases 0.000 claims description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims description 30
• 229940124597 therapeutic agent Drugs 0.000 claims description 30
• 206010006187 Breast cancer Diseases 0.000 claims description 29
• 208000026310 Breast neoplasm Diseases 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 229910020008 S(O) Inorganic materials 0.000 claims description 24
• 208000035475 disorder Diseases 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 239000003795 chemical substances by application Substances 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 239000002246 antineoplastic agent Substances 0.000 claims description 17
• 229910052801 chlorine Inorganic materials 0.000 claims description 15
• 229940127089 cytotoxic agent Drugs 0.000 claims description 15
• 229910052740 iodine Inorganic materials 0.000 claims description 15
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 14
• 239000003085 diluting agent Substances 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 9
• 125000002393 azetidinyl group Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000003566 oxetanyl group Chemical group 0.000 claims description 8
• 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 7
• 239000000314 lubricant Substances 0.000 claims description 7
• 230000001404 mediated effect Effects 0.000 claims description 7
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
• 206010033128 Ovarian cancer Diseases 0.000 claims description 6
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
• LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• 206010014733 Endometrial cancer Diseases 0.000 claims description 5
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• 206010060862 Prostate cancer Diseases 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 5
• 201000005202 lung cancer Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 206010046766 uterine cancer Diseases 0.000 claims description 5
• BKBDCKCPOHJNMA-WAIKUNEKSA-N (1R,3R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N([C@@H](CC2=CC(=CC=C12)O)C)CC(F)(F)F BKBDCKCPOHJNMA-WAIKUNEKSA-N 0.000 claims description 4
• DABPJEVISFOUNE-QMHKHESXSA-N (1R,4R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-4-methyl-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(C[C@@H](C2=CC(=CC=C12)O)C)S(=O)(=O)C DABPJEVISFOUNE-QMHKHESXSA-N 0.000 claims description 4
• DABPJEVISFOUNE-WAIKUNEKSA-N (1R,4S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-4-methyl-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(C[C@H](C2=CC(=CC=C12)O)C)S(=O)(=O)C DABPJEVISFOUNE-WAIKUNEKSA-N 0.000 claims description 4
• DABPJEVISFOUNE-MWTRTKDXSA-N (1S,4S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-4-methyl-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(C[C@H](C2=CC(=CC=C12)O)C)S(=O)(=O)C DABPJEVISFOUNE-MWTRTKDXSA-N 0.000 claims description 4
• IWCNMGHVEYTYJN-YHAMSUFESA-N FC1=C(C(=CC(=C1)OCCN1CC(C1)CF)F)[C@@H]1N([C@H](CC2=C3C(=CC=C12)NN=C3)C)CC(C)(C)F Chemical compound FC1=C(C(=CC(=C1)OCCN1CC(C1)CF)F)[C@@H]1N([C@H](CC2=C3C(=CC=C12)NN=C3)C)CC(C)(C)F IWCNMGHVEYTYJN-YHAMSUFESA-N 0.000 claims description 4
• IWCNMGHVEYTYJN-DXPJPUQTSA-N FC1=C(C(=CC(=C1)OCCN1CC(C1)CF)F)[C@H]1N([C@@H](CC2=C3C(=CC=C12)NN=C3)C)CC(C)(C)F Chemical compound FC1=C(C(=CC(=C1)OCCN1CC(C1)CF)F)[C@H]1N([C@@H](CC2=C3C(=CC=C12)NN=C3)C)CC(C)(C)F IWCNMGHVEYTYJN-DXPJPUQTSA-N 0.000 claims description 4
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 208000014951 hematologic disease Diseases 0.000 claims description 4
• 208000019423 liver disease Diseases 0.000 claims description 4
• JWUOZESJFTULNI-AREMUKBSSA-N (1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2-fluoro-2-methylpropyl)-1-methyl-3,4-dihydroisoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@]1(N(CCC2=CC(=CC=C12)O)CC(C)(C)F)C JWUOZESJFTULNI-AREMUKBSSA-N 0.000 claims description 3
• GYPXHXYCRMGLOU-HSZRJFAPSA-N (1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3,3-dimethyl-2-(2,2,2-trifluoroethyl)-1,4-dihydroisoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(C(CC2=CC(=CC=C12)O)(C)C)CC(F)(F)F GYPXHXYCRMGLOU-HSZRJFAPSA-N 0.000 claims description 3
• KTLXJZWWYPXZBP-UZUQRXQVSA-N (1R,3R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N([C@@H](CC2=CC=CC=C12)C)CC(F)(F)F KTLXJZWWYPXZBP-UZUQRXQVSA-N 0.000 claims description 3
• VOYGBWDJGBJHDH-WAIKUNEKSA-N (1R,3R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline-6-carboxylic acid Chemical compound C[C@@H]1CC2=C(C=CC(=C2)C(O)=O)[C@H](N1CC(F)(F)F)C1=CC=C(OCCN2CC(CF)C2)C=C1 VOYGBWDJGBJHDH-WAIKUNEKSA-N 0.000 claims description 3
• JMKZMWGLYQTHCM-MZNJEOGPSA-N (1R,3R)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FC(CN1[C@@H](C2=CC=C(C=C2C[C@H]1C)O)C1=CC=C(C=C1)OCCN1CC(C1)CF)(CO)F JMKZMWGLYQTHCM-MZNJEOGPSA-N 0.000 claims description 3
• PTNXVMQCPOSHGP-MZNJEOGPSA-N (1R,3R)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound C[C@@H]1CC2=C([C@H](N1CC(F)(F)CO)C1=CC=C(OCCN3CC(CF)C3)C=C1)C(O)=CC=C2 PTNXVMQCPOSHGP-MZNJEOGPSA-N 0.000 claims description 3
• KUSGGKASIHPZQJ-MZNJEOGPSA-N (1R,3R)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-3,4-dihydro-1H-isoquinoline-6-sulfonamide Chemical compound C[C@@H]1CC2=C(C=CC(=C2)S(N)(=O)=O)[C@H](N1CC(F)(F)CO)C1=CC=C(OCCN2CC(CF)C2)C=C1 KUSGGKASIHPZQJ-MZNJEOGPSA-N 0.000 claims description 3
• JWUOZESJFTULNI-SANMLTNESA-N (1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2-fluoro-2-methylpropyl)-1-methyl-3,4-dihydroisoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@]1(N(CCC2=CC(=CC=C12)O)CC(C)(C)F)C JWUOZESJFTULNI-SANMLTNESA-N 0.000 claims description 3
• YJLADFAOINOYCZ-QFIPXVFZSA-N (1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(CCC2=CC(=CC=C12)O)S(=O)(=O)C YJLADFAOINOYCZ-QFIPXVFZSA-N 0.000 claims description 3
• BKBDCKCPOHJNMA-HJPURHCSSA-N (1S,3S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N([C@H](CC2=CC(=CC=C12)O)C)CC(F)(F)F BKBDCKCPOHJNMA-HJPURHCSSA-N 0.000 claims description 3
• KTLXJZWWYPXZBP-SBUREZEXSA-N (1S,3S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N([C@H](CC2=CC=CC=C12)C)CC(F)(F)F KTLXJZWWYPXZBP-SBUREZEXSA-N 0.000 claims description 3
• JMKZMWGLYQTHCM-XDHUDOTRSA-N (1S,3S)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound C[C@H]1CC2=C(C=CC(O)=C2)[C@@H](N1CC(F)(F)CO)C1=CC=C(OCCN2CC(CF)C2)C=C1 JMKZMWGLYQTHCM-XDHUDOTRSA-N 0.000 claims description 3
• PTNXVMQCPOSHGP-XDHUDOTRSA-N (1S,3S)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound FC(CN1[C@H](C2=C(C=CC=C2C[C@@H]1C)O)C1=CC=C(C=C1)OCCN1CC(C1)CF)(CO)F PTNXVMQCPOSHGP-XDHUDOTRSA-N 0.000 claims description 3
• KUSGGKASIHPZQJ-XDHUDOTRSA-N (1S,3S)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-3,4-dihydro-1H-isoquinoline-6-sulfonamide Chemical compound FC(CN1[C@H](C2=CC=C(C=C2C[C@@H]1C)S(=O)(=O)N)C1=CC=C(C=C1)OCCN1CC(C1)CF)(CO)F KUSGGKASIHPZQJ-XDHUDOTRSA-N 0.000 claims description 3
• DABPJEVISFOUNE-HJPURHCSSA-N (1S,4R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-4-methyl-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(C[C@@H](C2=CC(=CC=C12)O)C)S(=O)(=O)C DABPJEVISFOUNE-HJPURHCSSA-N 0.000 claims description 3
• QCHUCQIQMVKSPC-WXTAPIANSA-N 1-[(1R,3R)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-3,4-dihydro-1H-isoquinolin-6-yl]ethanone Chemical compound C[C@@H]1CC2=C(C=CC(=C2)C(C)=O)[C@H](N1CC(F)(F)CO)C1=CC=C(OCCN2CC(CF)C2)C=C1 QCHUCQIQMVKSPC-WXTAPIANSA-N 0.000 claims description 3
• ZKQHQMPYZQYLCG-BVZFJXPGSA-N 2,2-difluoro-3-[(1S,3S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-6-(hydroxymethyl)-3-methyl-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-ol Chemical compound FC(CO)(CN1[C@H](C2=CC=C(C=C2C[C@@H]1C)CO)C1=CC=C(C=C1)OCCN1CC(C1)CF)F ZKQHQMPYZQYLCG-BVZFJXPGSA-N 0.000 claims description 3
• RNWOGOMXTBTLNW-BVZFJXPGSA-N 2-[(1S,3S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-yl]propan-2-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N([C@H](CC2=CC(=CC=C12)C(C)(C)O)C)CC(F)(F)F RNWOGOMXTBTLNW-BVZFJXPGSA-N 0.000 claims description 3
• HAWGBQHBOGNATE-HSZRJFAPSA-N 2-fluoro-1-[(1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-6-hydroxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-methylpropan-1-one Chemical compound FC(C(=O)N1[C@@H](C2=CC=C(C=C2CC1)O)C1=CC=C(C=C1)OCCN1CC(C1)CF)(C)C HAWGBQHBOGNATE-HSZRJFAPSA-N 0.000 claims description 3
• HAWGBQHBOGNATE-QHCPKHFHSA-N 2-fluoro-1-[(1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-6-hydroxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-methylpropan-1-one Chemical compound CC(C)(F)C(=O)N1CCC2=C(C=CC(O)=C2)[C@@H]1C1=CC=C(OCCN2CC(CF)C2)C=C1 HAWGBQHBOGNATE-QHCPKHFHSA-N 0.000 claims description 3
• LPSWHJANNYROHR-SANMLTNESA-N FC([C@]1(N(CCC2=CC(=CC=C12)O)CC(C)(C)F)C1=CC=C(C=C1)OCCN1CC(C1)CF)F Chemical compound FC([C@]1(N(CCC2=CC(=CC=C12)O)CC(C)(C)F)C1=CC=C(C=C1)OCCN1CC(C1)CF)F LPSWHJANNYROHR-SANMLTNESA-N 0.000 claims description 3
• GYPXHXYCRMGLOU-QHCPKHFHSA-N FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(C(CC2=CC(=CC=C12)O)(C)C)CC(F)(F)F Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(C(CC2=CC(=CC=C12)O)(C)C)CC(F)(F)F GYPXHXYCRMGLOU-QHCPKHFHSA-N 0.000 claims description 3
• IJLPCRAVOLBSOO-JOCHJYFZSA-N FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCC2=CC(=CC=C12)O)CC(F)(F)F Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCC2=CC(=CC=C12)O)CC(F)(F)F IJLPCRAVOLBSOO-JOCHJYFZSA-N 0.000 claims description 3
• GJTGISRLQSHKNA-HSZRJFAPSA-N FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCCC2=C1C=CC(=C2)O)CC(F)(F)F Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCCC2=C1C=CC(=C2)O)CC(F)(F)F GJTGISRLQSHKNA-HSZRJFAPSA-N 0.000 claims description 3
• 208000029462 Immunodeficiency disease Diseases 0.000 claims description 3
• BSUFGZPLIVGYCD-UHFFFAOYSA-N OC1=CC2=C(C=C1)C(N(CC2)C1=CC=CC=C1)C1=CC=C(OC2CN(CCCF)C2)C=C1 Chemical compound OC1=CC2=C(C=C1)C(N(CC2)C1=CC=CC=C1)C1=CC=C(OC2CN(CCCF)C2)C=C1 BSUFGZPLIVGYCD-UHFFFAOYSA-N 0.000 claims description 3
• IJLPCRAVOLBSOO-QFIPXVFZSA-N OC1=CC2=C(C=C1)[C@@H](N(CC(F)(F)F)CC2)C1=CC=C(OCCN2CC(CF)C2)C=C1 Chemical compound OC1=CC2=C(C=C1)[C@@H](N(CC(F)(F)F)CC2)C1=CC=C(OCCN2CC(CF)C2)C=C1 IJLPCRAVOLBSOO-QFIPXVFZSA-N 0.000 claims description 3
• APHXUUHZAZJKAK-QHCPKHFHSA-N [(1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-yl]methanol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(CCC2=CC(=CC=C12)CO)CC(F)(F)F APHXUUHZAZJKAK-QHCPKHFHSA-N 0.000 claims description 3
• 239000003443 antiviral agent Substances 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 102000015694 estrogen receptors Human genes 0.000 claims description 3
• 230000000508 neurotrophic effect Effects 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• LPSWHJANNYROHR-AREMUKBSSA-N (1R)-1-(difluoromethyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2-fluoro-2-methylpropyl)-3,4-dihydroisoquinolin-6-ol Chemical compound FC([C@@]1(N(CCC2=CC(=CC=C12)O)CC(C)(C)F)C1=CC=C(C=C1)OCCN1CC(C1)CF)F LPSWHJANNYROHR-AREMUKBSSA-N 0.000 claims description 2
• GJTGISRLQSHKNA-QHCPKHFHSA-N (1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-7-ol Chemical compound OC1=CC2=C(C=C1)[C@@H](N(CC(F)(F)F)CCC2)C1=CC=C(OCCN2CC(CF)C2)C=C1 GJTGISRLQSHKNA-QHCPKHFHSA-N 0.000 claims description 2
• ZKQHQMPYZQYLCG-IQGLISFBSA-N 2,2-difluoro-3-[(1R,3R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-6-(hydroxymethyl)-3-methyl-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-ol Chemical compound FC(CO)(CN1[C@@H](C2=CC=C(C=C2C[C@H]1C)CO)C1=CC=C(C=C1)OCCN1CC(C1)CF)F ZKQHQMPYZQYLCG-IQGLISFBSA-N 0.000 claims description 2
• QFDWEGJPSMCKDG-UHFFFAOYSA-N OC1=CC2=C(C=C1)C(N(CC2)C1=CC=CC=C1)C1=CC=C(OCCN2CC(CF)C2)C=C1 Chemical compound OC1=CC2=C(C=C1)C(N(CC2)C1=CC=CC=C1)C1=CC=C(OCCN2CC(CF)C2)C=C1 QFDWEGJPSMCKDG-UHFFFAOYSA-N 0.000 claims description 2
• APHXUUHZAZJKAK-HSZRJFAPSA-N [(1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-yl]methanol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCC2=CC(=CC=C12)CO)CC(F)(F)F APHXUUHZAZJKAK-HSZRJFAPSA-N 0.000 claims description 2
• DFVXEZWOASLALX-JOCHJYFZSA-N (1R)-1-[2,6-difluoro-4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FC1=C(C(=CC(=C1)OCCN1CC(C1)CF)F)[C@@H]1N(CCC2=CC(=CC=C12)O)CC(F)(F)F DFVXEZWOASLALX-JOCHJYFZSA-N 0.000 claims 2
• VLOSTMAVKBAZEM-HSZRJFAPSA-N (1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-1-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@]1(N(CCC2=CC(=CC=C12)O)CC(F)(F)F)C VLOSTMAVKBAZEM-HSZRJFAPSA-N 0.000 claims 2
• DWFGIGKAFDWCKR-JOCHJYFZSA-N (1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCC2=CC(=CC=C12)C(=O)N)CC(F)(F)F DWFGIGKAFDWCKR-JOCHJYFZSA-N 0.000 claims 2
• ALHSDDHUURUUFF-XMMPIXPASA-N (1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2-fluoro-2-methylpropyl)-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FC(CN1[C@@H](C2=CC=C(C=C2CC1)O)C1=CC=C(C=C1)OCCN1CC(C1)CF)(C)C ALHSDDHUURUUFF-XMMPIXPASA-N 0.000 claims 2
• YJLADFAOINOYCZ-JOCHJYFZSA-N (1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCC2=CC(=CC=C12)O)S(=O)(=O)C YJLADFAOINOYCZ-JOCHJYFZSA-N 0.000 claims 2
• WIWAYAMYPZKARF-RUZDIDTESA-N (1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-6-(1H-pyrazol-4-yl)-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCC2=CC(=CC=C12)C=1C=NNC=1)CC(F)(F)F WIWAYAMYPZKARF-RUZDIDTESA-N 0.000 claims 2
• RSKNBOQWVOURBD-RUZDIDTESA-N (1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-6-(1H-pyrazol-5-yl)-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCC2=CC(=CC=C12)C1=NNC=C1)CC(F)(F)F RSKNBOQWVOURBD-RUZDIDTESA-N 0.000 claims 2
• CLVNGZILSMJZDX-XMMPIXPASA-N (1R)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-1-methyl-3,4-dihydroisoquinolin-6-ol Chemical compound FC(CN1[C@](C2=CC=C(C=C2CC1)O)(C)C1=CC=C(C=C1)OCCN1CC(C1)CF)(CO)F CLVNGZILSMJZDX-XMMPIXPASA-N 0.000 claims 2
• BNQXMOBIGDCFOW-NFQMXDRXSA-N (1R)-2-(2-fluoro-2-methylpropyl)-1-methyl-1-[4-[2-[(3R)-3-methylpyrrolidin-1-yl]ethoxy]phenyl]-3,4-dihydroisoquinolin-6-ol Chemical compound FC(CN1[C@@](C2=CC=C(C=C2CC1)O)(C1=CC=C(C=C1)OCCN1C[C@@H](CC1)C)C)(C)C BNQXMOBIGDCFOW-NFQMXDRXSA-N 0.000 claims 2
• DFVXEZWOASLALX-QFIPXVFZSA-N (1S)-1-[2,6-difluoro-4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FC1=C(C(=CC(=C1)OCCN1CC(C1)CF)F)[C@H]1N(CCC2=CC(=CC=C12)O)CC(F)(F)F DFVXEZWOASLALX-QFIPXVFZSA-N 0.000 claims 2
• DWFGIGKAFDWCKR-QFIPXVFZSA-N (1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(CCC2=CC(=CC=C12)C(=O)N)CC(F)(F)F DWFGIGKAFDWCKR-QFIPXVFZSA-N 0.000 claims 2
• WIWAYAMYPZKARF-VWLOTQADSA-N (1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-6-(1H-pyrazol-4-yl)-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(CCC2=CC(=CC=C12)C=1C=NNC=1)CC(F)(F)F WIWAYAMYPZKARF-VWLOTQADSA-N 0.000 claims 2
• CLVNGZILSMJZDX-DEOSSOPVSA-N (1S)-2-(2,2-difluoro-3-hydroxypropyl)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-1-methyl-3,4-dihydroisoquinolin-6-ol Chemical compound FC(CN1[C@@](C2=CC=C(C=C2CC1)O)(C)C1=CC=C(C=C1)OCCN1CC(C1)CF)(CO)F CLVNGZILSMJZDX-DEOSSOPVSA-N 0.000 claims 2
• BNQXMOBIGDCFOW-HRFSGMKKSA-N (1S)-2-(2-fluoro-2-methylpropyl)-1-methyl-1-[4-[2-[(3R)-3-methylpyrrolidin-1-yl]ethoxy]phenyl]-3,4-dihydroisoquinolin-6-ol Chemical compound FC(CN1[C@](C2=CC=C(C=C2CC1)O)(C1=CC=C(C=C1)OCCN1C[C@@H](CC1)C)C)(C)C BNQXMOBIGDCFOW-HRFSGMKKSA-N 0.000 claims 2
• UEMRZFLCPNBOQA-MWTRTKDXSA-N (1S,3R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N([C@@H](CC2=CC(=CC=C12)O)C)S(=O)(=O)C UEMRZFLCPNBOQA-MWTRTKDXSA-N 0.000 claims 2
• VOYGBWDJGBJHDH-HJPURHCSSA-N (1S,3S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline-6-carboxylic acid Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N([C@H](CC2=CC(=CC=C12)C(=O)O)C)CC(F)(F)F VOYGBWDJGBJHDH-HJPURHCSSA-N 0.000 claims 2
• UEMRZFLCPNBOQA-HJPURHCSSA-N (1S,3S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N([C@H](CC2=CC(=CC=C12)O)C)S(=O)(=O)C UEMRZFLCPNBOQA-HJPURHCSSA-N 0.000 claims 2
• AFHJGLYEFXWNLI-UHFFFAOYSA-N 1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-1-methyl-2-methylsulfonyl-3,4-dihydroisoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)C1(N(CCC2=CC(=CC=C12)O)S(=O)(=O)C)C AFHJGLYEFXWNLI-UHFFFAOYSA-N 0.000 claims 2
• RNWOGOMXTBTLNW-IQGLISFBSA-N 2-[(1R,3R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-yl]propan-2-ol Chemical compound C[C@@H]1CC2=C(C=CC(=C2)C(C)(C)O)[C@H](N1CC(F)(F)F)C1=CC=C(OCCN2CC(CF)C2)C=C1 RNWOGOMXTBTLNW-IQGLISFBSA-N 0.000 claims 2
• XUNUAWWTPDXMAL-AREMUKBSSA-N 4-[(1R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-yl]morpholine Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N(CCC2=CC(=CC=C12)N1CCOCC1)CC(F)(F)F XUNUAWWTPDXMAL-AREMUKBSSA-N 0.000 claims 2
• XUNUAWWTPDXMAL-SANMLTNESA-N 4-[(1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinolin-6-yl]morpholine Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(CCC2=CC(=CC=C12)N1CCOCC1)CC(F)(F)F XUNUAWWTPDXMAL-SANMLTNESA-N 0.000 claims 2
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 2
• 239000002955 immunomodulating agent Substances 0.000 claims 2
• 229940121354 immunomodulator Drugs 0.000 claims 2
• UEMRZFLCPNBOQA-WAIKUNEKSA-N (1R,3R)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N([C@@H](CC2=CC(=CC=C12)O)C)S(=O)(=O)C UEMRZFLCPNBOQA-WAIKUNEKSA-N 0.000 claims 1
• UEMRZFLCPNBOQA-QMHKHESXSA-N (1R,3S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3-methyl-2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@H]1N([C@H](CC2=CC(=CC=C12)O)C)S(=O)(=O)C UEMRZFLCPNBOQA-QMHKHESXSA-N 0.000 claims 1
• VLOSTMAVKBAZEM-QHCPKHFHSA-N (1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-1-methyl-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-6-ol Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@]1(N(CCC2=CC(=CC=C12)O)CC(F)(F)F)C VLOSTMAVKBAZEM-QHCPKHFHSA-N 0.000 claims 1
• ALHSDDHUURUUFF-DEOSSOPVSA-N (1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-2-(2-fluoro-2-methylpropyl)-3,4-dihydro-1H-isoquinolin-6-ol Chemical compound FC(CN1[C@H](C2=CC=C(C=C2CC1)O)C1=CC=C(C=C1)OCCN1CC(C1)CF)(C)C ALHSDDHUURUUFF-DEOSSOPVSA-N 0.000 claims 1
• RSKNBOQWVOURBD-VWLOTQADSA-N (1S)-1-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-6-(1H-pyrazol-5-yl)-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline Chemical compound FCC1CN(C1)CCOC1=CC=C(C=C1)[C@@H]1N(CCC2=CC(=CC=C12)C1=NNC=C1)CC(F)(F)F RSKNBOQWVOURBD-VWLOTQADSA-N 0.000 claims 1
• OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims 1
• PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims 1
• WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims 1
• GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims 1
• IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 claims 1
• RSGWJAIJNYLBMJ-UHFFFAOYSA-N 6-[2,6-difluoro-4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-3,7-bis(2-fluoro-2-methylpropyl)-8-methyl-8,9-dihydro-6H-pyrazolo[4,3-f]isoquinoline Chemical compound CC1CC2=C(C=CC3=C2C=NN3CC(C)(C)F)C(N1CC(C)(C)F)C1=C(F)C=C(OCCN2CC(CF)C2)C=C1F RSGWJAIJNYLBMJ-UHFFFAOYSA-N 0.000 claims 1
• IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims 1
• IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 claims 1
• BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 claims 1
• UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 claims 1
• LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 claims 1
• POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 claims 1
• QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims 1
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• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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• KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 1
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