JP5213229B2 - キナーゼ調節因子および使用方法 - Google Patents

Info

Publication number

JP5213229B2

JP5213229B2 JP2007509678A JP2007509678A JP5213229B2 JP 5213229 B2 JP5213229 B2 JP 5213229B2 JP 2007509678 A JP2007509678 A JP 2007509678A JP 2007509678 A JP2007509678 A JP 2007509678A JP 5213229 B2 JP5213229 B2 JP 5213229B2

Authority

JP

Japan

Prior art keywords

pyrazolo

piperazin

pyrimidin

bromo

methyl

Prior art date

2004-04-23

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.)

Expired - Fee Related

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims description 76
• 108091000080 Phosphotransferase Proteins 0.000 title claims description 42
• 102000020233 phosphotransferase Human genes 0.000 title claims description 42
• -1 2,5-dioxopyrrolidin-1-yl Chemical group 0.000 claims description 286
• 150000001875 compounds Chemical class 0.000 claims description 208
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 184
• 239000000203 mixture Substances 0.000 claims description 145
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 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 88
• 239000011541 reaction mixture Substances 0.000 claims description 85
• 230000000694 effects Effects 0.000 claims description 61
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims description 54
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
• 229910052757 nitrogen Inorganic materials 0.000 claims description 45
• 125000004122 cyclic group Chemical group 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
• 201000010099 disease Diseases 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 27
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 26
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000003107 substituted aryl group Chemical group 0.000 claims description 21
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 20
• 239000003795 chemical substances by application Substances 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 102000001253 Protein Kinase Human genes 0.000 claims description 15
• 108060006633 protein kinase Proteins 0.000 claims description 15
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 14
• 230000001413 cellular effect Effects 0.000 claims description 13
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 125000002252 acyl group Chemical group 0.000 claims description 9
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
• 238000012216 screening Methods 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 238000012360 testing method Methods 0.000 claims description 9
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 7
• 230000002159 abnormal effect Effects 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• VXOGMIMOLDTFBZ-UHFFFAOYSA-N 3-bromo-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 VXOGMIMOLDTFBZ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 238000001727 in vivo Methods 0.000 claims description 5
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• YDCPJETYANMVFW-UHFFFAOYSA-N 2-[3-[4-[1-tert-butyl-3-(trifluoromethyl)pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-5-chloro-2-methylphenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NN(C=3N=CN=2)C(C)(C)C)C(F)(F)F)=C1C YDCPJETYANMVFW-UHFFFAOYSA-N 0.000 claims description 3
• FRSGTYFDKGJXNW-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)-5-(3,3,3-trifluoropropoxy)aniline Chemical compound C1=C(OCCC(F)(F)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 FRSGTYFDKGJXNW-UHFFFAOYSA-N 0.000 claims description 3
• OJSJVZOGAFBPJE-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C=NNC=3N=CN=2)CC1 OJSJVZOGAFBPJE-UHFFFAOYSA-N 0.000 claims description 3
• IYFFGVGWWQJVFY-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C IYFFGVGWWQJVFY-UHFFFAOYSA-N 0.000 claims description 3
• KFJYAVVIRNQQKI-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-propyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CCC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C KFJYAVVIRNQQKI-UHFFFAOYSA-N 0.000 claims description 3
• 208000035475 disorder Diseases 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 230000002062 proliferating effect Effects 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• CFDGOSRQZCDYHK-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazine-2-carboxylic acid Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1C(O)=O)CCN1C1=CC=CC(Cl)=C1 CFDGOSRQZCDYHK-UHFFFAOYSA-N 0.000 claims description 2
• OFDSSLFGGWSMMJ-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]butan-1-one Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)CCC)=CC=1NCCN1CCCC1 OFDSSLFGGWSMMJ-UHFFFAOYSA-N 0.000 claims description 2
• DCNODYHFBSBLGN-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]pentan-1-one Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)CCCC)=CC=1NCCN1CCCC1 DCNODYHFBSBLGN-UHFFFAOYSA-N 0.000 claims description 2
• HPIIDXXXXRXUCH-UHFFFAOYSA-N 1-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]isoquinoline Chemical compound C1=CC=C2C(N3CCN(CC3)C=3N=CN=C4NN=C(C=34)CC)=NC=CC2=C1 HPIIDXXXXRXUCH-UHFFFAOYSA-N 0.000 claims description 2
• TZFORYKWKFKQQB-UHFFFAOYSA-N 1-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methoxyphenyl]-n,n-dimethylmethanamine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(CN(C)C)=C1OC TZFORYKWKFKQQB-UHFFFAOYSA-N 0.000 claims description 2
• HRQVYTNMNDWJAQ-UHFFFAOYSA-N 2-chloro-4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-methylphenol Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=C(O)C=C1C HRQVYTNMNDWJAQ-UHFFFAOYSA-N 0.000 claims description 2
• AJWFNKDUKOFVSO-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(2-phenylethynyl)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(C#CC=2C=CC=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 AJWFNKDUKOFVSO-UHFFFAOYSA-N 0.000 claims description 2
• HGCQHRUBKWVKHA-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC1=NOC(C=2C=C(C(C)=C(NCCN3CCCC3)C=2)N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=N1 HGCQHRUBKWVKHA-UHFFFAOYSA-N 0.000 claims description 2
• YWUIVMBLSSVYOU-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-methylsulfonyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(S(C)(=O)=O)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 YWUIVMBLSSVYOU-UHFFFAOYSA-N 0.000 claims description 2
• DRFKNPFAXPCTQG-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2,2-dimethylpropoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC(C)(C)C)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 DRFKNPFAXPCTQG-UHFFFAOYSA-N 0.000 claims description 2
• BZWINHLDUBAFJC-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(3,3-dimethylbutyl)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(CCC(C)(C)C)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 BZWINHLDUBAFJC-UHFFFAOYSA-N 0.000 claims description 2
• MZMMBFATXSYGDE-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(cyclobutylmethoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC2CCC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 MZMMBFATXSYGDE-UHFFFAOYSA-N 0.000 claims description 2
• IYGKFXLAHMDZHD-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(cyclopentylmethoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC2CCCC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 IYGKFXLAHMDZHD-UHFFFAOYSA-N 0.000 claims description 2
• YYRHQZUDEOMFMB-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-[(2,2-difluorocyclopropyl)methoxy]-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC2C(C2)(F)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 YYRHQZUDEOMFMB-UHFFFAOYSA-N 0.000 claims description 2
• LYDIYXALBYBXDU-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-ethylsulfonyl-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(S(=O)(=O)CC)=CC=1NCCN1CCCC1 LYDIYXALBYBXDU-UHFFFAOYSA-N 0.000 claims description 2
• LWZBMXSUTVCFDI-UHFFFAOYSA-N 3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(2-methylpropoxy)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(OCC(C)C)=CC=1NCCN1CCCC1 LWZBMXSUTVCFDI-UHFFFAOYSA-N 0.000 claims description 2
• FVTGZBCGLSOVNH-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-yn-1-ol Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C#CCO)=NNC=3N=CN=2)CC1 FVTGZBCGLSOVNH-UHFFFAOYSA-N 0.000 claims description 2
• ITZRTIPTIGXEDC-UHFFFAOYSA-N 3-benzyl-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(CC=4C=CC=CC=4)=NNC=3N=CN=2)CC1 ITZRTIPTIGXEDC-UHFFFAOYSA-N 0.000 claims description 2
• ZXVQZHJGOFVOMR-UHFFFAOYSA-N 3-bromo-4-[4-(2,5-difluorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound FC1=CC=C(F)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 ZXVQZHJGOFVOMR-UHFFFAOYSA-N 0.000 claims description 2
• QTGCAQPANBHFRY-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1CCCN1CCCC1 QTGCAQPANBHFRY-UHFFFAOYSA-N 0.000 claims description 2
• LVCUTRIUEIMSSN-UHFFFAOYSA-N 3-bromo-5-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-n-phenylbenzamide Chemical compound C1=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C(Br)C=C1C(=O)NC1=CC=CC=C1 LVCUTRIUEIMSSN-UHFFFAOYSA-N 0.000 claims description 2
• ZUGWVLCGKRAMCK-UHFFFAOYSA-N 3-ethyl-4-(4-phenylpiperazin-1-yl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC=C1 ZUGWVLCGKRAMCK-UHFFFAOYSA-N 0.000 claims description 2
• ABCLBFFJWCINQC-UHFFFAOYSA-N 3-ethyl-4-[4-(3-methoxy-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC(OC)=C1C ABCLBFFJWCINQC-UHFFFAOYSA-N 0.000 claims description 2
• DSUZVNZHENWVEH-UHFFFAOYSA-N 3-ethyl-4-[4-(3-methoxyphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC(OC)=C1 DSUZVNZHENWVEH-UHFFFAOYSA-N 0.000 claims description 2
• NQGUYIIGRJFWGT-UHFFFAOYSA-N 3-methyl-4-[4-(2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(C)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC=C1C NQGUYIIGRJFWGT-UHFFFAOYSA-N 0.000 claims description 2
• SXKQDCIDBSRHGY-UHFFFAOYSA-N 4-(3-chlorophenyl)-1-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-n-methylpiperazine-2-carboxamide Chemical compound C=12C(CC)=NNC2=NC=NC=1N(C(C1)C(=O)NC)CCN1C1=CC=CC(Cl)=C1 SXKQDCIDBSRHGY-UHFFFAOYSA-N 0.000 claims description 2
• RPGYWHYWENYQGY-UHFFFAOYSA-N 4-(4-phenylpiperazin-1-yl)-1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C=2C=3C=NNC=3N=CN=2)CCN1C1=CC=CC=C1 RPGYWHYWENYQGY-UHFFFAOYSA-N 0.000 claims description 2
• DBHLLUYXGVGCBT-UHFFFAOYSA-N 4-[2-[2-chloro-4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]phenoxy]ethyl]morpholine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=C1Cl)=CC=C1OCCN1CCOCC1 DBHLLUYXGVGCBT-UHFFFAOYSA-N 0.000 claims description 2
• UQLMPDRFVRHEEC-UHFFFAOYSA-N 4-[4-(2,5-difluorophenyl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(F)=CC=C1F UQLMPDRFVRHEEC-UHFFFAOYSA-N 0.000 claims description 2
• HWUXRXXIRBYCNK-UHFFFAOYSA-N 4-[4-(2-methylphenyl)piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=CC=C1N1CCN(C=2C=3C=NNC=3N=CN=2)CC1 HWUXRXXIRBYCNK-UHFFFAOYSA-N 0.000 claims description 2
• OIQHXDDUNABRJN-UHFFFAOYSA-N 4-[4-(3,6-dimethylpyrazin-2-yl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=NC(C)=CN=C1C OIQHXDDUNABRJN-UHFFFAOYSA-N 0.000 claims description 2
• ZTTZSXXHUDNUPX-UHFFFAOYSA-N 4-[4-(3-bromo-2-chloro-5-fluorophenyl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(F)=CC(Br)=C1Cl ZTTZSXXHUDNUPX-UHFFFAOYSA-N 0.000 claims description 2
• XATAOMSNDMSGSO-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC(Cl)=C1 XATAOMSNDMSGSO-UHFFFAOYSA-N 0.000 claims description 2
• YXAQKJOQSNRGHK-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)piperazin-1-yl]-3-methyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(C)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC(Cl)=C1 YXAQKJOQSNRGHK-UHFFFAOYSA-N 0.000 claims description 2
• FFLJZUPHFGTAMD-UHFFFAOYSA-N 4-[4-(4,6-dimethylpyrimidin-2-yl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=NC(C)=CC(C)=N1 FFLJZUPHFGTAMD-UHFFFAOYSA-N 0.000 claims description 2
• TZRRXZFUOZMLHU-UHFFFAOYSA-N 4-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1OC TZRRXZFUOZMLHU-UHFFFAOYSA-N 0.000 claims description 2
• JDRLXIDHAYBNRM-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(2-methoxyethoxymethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(COCCOC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C JDRLXIDHAYBNRM-UHFFFAOYSA-N 0.000 claims description 2
• WSHLJCGMVSJNMB-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(2-methylpropyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC(C)C)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C WSHLJCGMVSJNMB-UHFFFAOYSA-N 0.000 claims description 2
• PEXFLFCCUBQENE-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-methylpiperazin-1-yl)-1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCN1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 PEXFLFCCUBQENE-UHFFFAOYSA-N 0.000 claims description 2
• BXXGWPDHOXTRRE-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)CC1 BXXGWPDHOXTRRE-UHFFFAOYSA-N 0.000 claims description 2
• HGNLAXAYDKLPAN-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-methyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(C)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C HGNLAXAYDKLPAN-UHFFFAOYSA-N 0.000 claims description 2
• QMRYFQJVJSUZLY-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-methyl-6-phenyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(C)=NNC2=NC(C=2C=CC=CC=2)=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C QMRYFQJVJSUZLY-UHFFFAOYSA-N 0.000 claims description 2
• DBBPQRUDHSGXGI-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-phenyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC=CC=4)=NNC=3N=CN=2)CC1 DBBPQRUDHSGXGI-UHFFFAOYSA-N 0.000 claims description 2
• GVPKPIYHQSAUFM-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-propan-2-yl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(C(C)C)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C GVPKPIYHQSAUFM-UHFFFAOYSA-N 0.000 claims description 2
• CUTHWLLCENKSGW-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-6-ethyl-1h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C=NNC2=NC(CC)=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C CUTHWLLCENKSGW-UHFFFAOYSA-N 0.000 claims description 2
• PRVDHIXOOBBJFD-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-6-methyl-1h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C=NNC2=NC(C)=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C PRVDHIXOOBBJFD-UHFFFAOYSA-N 0.000 claims description 2
• PZPHGLIZCQICOD-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-6-propan-2-yl-1h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C=NNC2=NC(C(C)C)=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C PZPHGLIZCQICOD-UHFFFAOYSA-N 0.000 claims description 2
• VUZSRKURYLGNGT-UHFFFAOYSA-N 4-[4-(5-chloro-3-methoxy-2-methylphenyl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(OC)=C1C VUZSRKURYLGNGT-UHFFFAOYSA-N 0.000 claims description 2
• MYAYFLXJENQGNP-UHFFFAOYSA-N 4-[4-(5-chloro-4-methoxy-2-methylphenyl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=C(OC)C=C1C MYAYFLXJENQGNP-UHFFFAOYSA-N 0.000 claims description 2
• MOWCFUDCJQIYNA-UHFFFAOYSA-N 4-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC2)C=2C=3C=NNC=3N=CN=2)=C1 MOWCFUDCJQIYNA-UHFFFAOYSA-N 0.000 claims description 2
• BJVXKHFOWCDPLN-UHFFFAOYSA-N 4-[4-[3-chloro-4-(2-piperidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=C1Cl)=CC=C1OCCN1CCCCC1 BJVXKHFOWCDPLN-UHFFFAOYSA-N 0.000 claims description 2
• PBHIIIVVBPIJSN-UHFFFAOYSA-N 4-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2H-pyrazolo[3,4-d]pyrimidin-3-yl]phenol Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(O)=CC=4)=NNC=3N=CN=2)CC1 PBHIIIVVBPIJSN-UHFFFAOYSA-N 0.000 claims description 2
• DARRPJUVNRFGQX-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[2-(1-methylpiperidin-4-yl)ethoxy]phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCC1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C DARRPJUVNRFGQX-UHFFFAOYSA-N 0.000 claims description 2
• UIIOSEYTZDZNAG-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[3-(4-methylpiperazin-1-yl)propyl]phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCN1CCCC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C UIIOSEYTZDZNAG-UHFFFAOYSA-N 0.000 claims description 2
• FRYZXWBIDBKNTC-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N1CC2CC1CN2C1=CC=CC(Cl)=C1 FRYZXWBIDBKNTC-UHFFFAOYSA-N 0.000 claims description 2
• ZEGDVMSZKIZCEO-UHFFFAOYSA-N 4-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]morpholine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1N1CCOCC1 ZEGDVMSZKIZCEO-UHFFFAOYSA-N 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• PHHJAFUIIRWPQI-UHFFFAOYSA-N 5-bromo-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylaniline Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Br)=CC(N)=C1C PHHJAFUIIRWPQI-UHFFFAOYSA-N 0.000 claims description 2
• OGKBRMWNHGMVFX-UHFFFAOYSA-N 5-chloro-2-methyl-n-(2-pyrrolidin-1-ylethyl)-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]aniline Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1NCCN1CCCC1 OGKBRMWNHGMVFX-UHFFFAOYSA-N 0.000 claims description 2
• BKYQHYYQDPBHJM-UHFFFAOYSA-N [5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methoxyphenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1OC)=CC(Cl)=CC=1C(=O)N1CCN(C)CC1 BKYQHYYQDPBHJM-UHFFFAOYSA-N 0.000 claims description 2
• XRLQDQSANHSNIL-UHFFFAOYSA-N [5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methoxyphenyl]methanol Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(CO)=C1OC XRLQDQSANHSNIL-UHFFFAOYSA-N 0.000 claims description 2
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• WYIZYVTVOHRTSK-UHFFFAOYSA-N n'-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(N(C)CCN(C)C)=C1C WYIZYVTVOHRTSK-UHFFFAOYSA-N 0.000 claims description 2
• UKRKRPLHUUSIOI-UHFFFAOYSA-N n,n-diethyl-2-[3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]ethanamine Chemical compound CCN(CC)CCOC1=CC=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C UKRKRPLHUUSIOI-UHFFFAOYSA-N 0.000 claims description 2
• QPJAQDDXUMCFFT-UHFFFAOYSA-N n-[3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-ynyl]acetamide Chemical compound C=12C(C#CCNC(=O)C)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C QPJAQDDXUMCFFT-UHFFFAOYSA-N 0.000 claims description 2
• IXQLYMMGMJNIFK-UHFFFAOYSA-N n-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C IXQLYMMGMJNIFK-UHFFFAOYSA-N 0.000 claims description 2
• CEWFUFAYEYMGEO-UHFFFAOYSA-N n-[[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methoxyphenyl]methyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(CNCCN(C)C)=C1OC CEWFUFAYEYMGEO-UHFFFAOYSA-N 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• OSZJZLURIWBTMR-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 OSZJZLURIWBTMR-UHFFFAOYSA-N 0.000 claims 3
• AGGZVELGCPADHT-UHFFFAOYSA-N N'-(2-pyrrolidin-1-ylethyl)benzohydrazide Chemical compound C(C1=CC=CC=C1)(=O)NNCCN1CCCC1 AGGZVELGCPADHT-UHFFFAOYSA-N 0.000 claims 3
• IJBZFRMMDXVGCU-SNAWJCMRSA-N (e)-3-[4-[4-[5-[2,3-difluoro-2-(fluoromethyl)propoxy]-2-methyl-3-(2-pyrrolidin-1-ylethylamino)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-enoic acid Chemical compound C1=C(OCC(F)(CF)CF)C=C(N2CCN(CC2)C=2C=3C(\C=C\C(O)=O)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 IJBZFRMMDXVGCU-SNAWJCMRSA-N 0.000 claims 2
• VEUAGFBTUOWMGS-UHFFFAOYSA-N 1-[2-[2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methylphenyl]phenoxy]ethyl]pyrrolidine-2,5-dione Chemical compound C1=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=CC=C1C1=CC=CC=C1OCCN1C(=O)CCC1=O VEUAGFBTUOWMGS-UHFFFAOYSA-N 0.000 claims 2
• IKBSEBRGSVFUHM-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]-4,4,4-trifluorobutan-1-one Chemical compound C1=C(C(=O)CCC(F)(F)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 IKBSEBRGSVFUHM-UHFFFAOYSA-N 0.000 claims 2
• AEPBFFNXZJQDMU-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]butan-1-ol Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(O)CCC)=CC=1NCCN1CCCC1 AEPBFFNXZJQDMU-UHFFFAOYSA-N 0.000 claims 2
• JPGSIPPBCGKIIU-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2-pyrrolidin-1-ylethylamino)phenyl]butan-1-one Chemical compound C=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)CCC)=CC=1NCCN1CCCC1 JPGSIPPBCGKIIU-UHFFFAOYSA-N 0.000 claims 2
• CXWRIIBHGFNKAV-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)-5-(2,2,2-trifluoroethoxy)aniline Chemical compound C1=C(OCC(F)(F)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 CXWRIIBHGFNKAV-UHFFFAOYSA-N 0.000 claims 2
• YJOVRFFTOQUZOT-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)-5-(2,2,2-trifluoroethoxymethyl)aniline Chemical compound C1=C(COCC(F)(F)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 YJOVRFFTOQUZOT-UHFFFAOYSA-N 0.000 claims 2
• ZFGPLQJDDUAPLD-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(1,1-difluorobutyl)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(F)(F)CCC)=CC=1NCCN1CCCC1 ZFGPLQJDDUAPLD-UHFFFAOYSA-N 0.000 claims 2
• XFVUESCLIPSCDS-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(ethoxymethyl)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(COCC)=CC=1NCCN1CCCC1 XFVUESCLIPSCDS-UHFFFAOYSA-N 0.000 claims 2
• DNEVYQASLHDDSQ-UHFFFAOYSA-N 3-[4-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-1-methyl-6-(trifluoromethyl)benzimidazol-2-yl]propan-1-ol Chemical compound C1=C(C(F)(F)F)C=C2N(C)C(CCCO)=NC2=C1N(CC1)CCN1C1=NC=NC2=C1C(Br)=NN2 DNEVYQASLHDDSQ-UHFFFAOYSA-N 0.000 claims 2
• SMNSMHSHWGBIFH-UHFFFAOYSA-N 3-[4-[4-[5-[2,3-difluoro-2-(fluoromethyl)propoxy]-2-methyl-3-(2-pyrrolidin-1-ylethylamino)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-yn-1-ol Chemical compound C1=C(OCC(F)(CF)CF)C=C(N2CCN(CC2)C=2C=3C(C#CCO)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 SMNSMHSHWGBIFH-UHFFFAOYSA-N 0.000 claims 2
• RAQLRASZPYFRHR-UHFFFAOYSA-N 3-bromo-4-[4-[2-chloro-5-[4-fluoro-2-(2-pyrrolidin-1-ylethoxy)phenyl]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=1C(F)=CC=C(C=2C=C(C(Cl)=CC=2)N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C=1OCCN1CCCC1 RAQLRASZPYFRHR-UHFFFAOYSA-N 0.000 claims 2
• NCUIHEKCQCSDGR-UHFFFAOYSA-N 3-bromo-4-[4-[5-[3-fluoro-2-(2-pyrrolidin-1-ylethoxy)phenyl]-2-methylphenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=CC=C1C1=CC=CC(F)=C1OCCN1CCCC1 NCUIHEKCQCSDGR-UHFFFAOYSA-N 0.000 claims 2
• MFCRUXWKACGBRB-UHFFFAOYSA-N 4-[3-[2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methylphenyl]phenoxy]propyl]morpholine Chemical compound C1=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=CC=C1C1=CC=CC=C1OCCCN1CCOCC1 MFCRUXWKACGBRB-UHFFFAOYSA-N 0.000 claims 2
• 239000004215 Carbon black (E152) Substances 0.000 claims 2
• URDNYNTUOXZTMC-UHFFFAOYSA-N [3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]-cyclopropylmethanone Chemical compound C1=C(C(=O)C2CC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 URDNYNTUOXZTMC-UHFFFAOYSA-N 0.000 claims 2
• 125000002393 azetidinyl group Chemical group 0.000 claims 2
• 125000001475 halogen functional group Chemical group 0.000 claims 2
• 229930195733 hydrocarbon Natural products 0.000 claims 2
• 150000002430 hydrocarbons Chemical class 0.000 claims 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
• UCHDIMBSVPCEED-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-n-methylpiperazine-2-carboxamide Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1C(=O)NC)CCN1C1=CC=CC(Cl)=C1 UCHDIMBSVPCEED-UHFFFAOYSA-N 0.000 claims 1
• JEWJTXCLTYTKGJ-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]ethanone Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)C)=CC=1NCCN1CCCC1 JEWJTXCLTYTKGJ-UHFFFAOYSA-N 0.000 claims 1
• DEJZGAXRKVTAOI-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]propan-1-one Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)CC)=CC=1NCCN1CCCC1 DEJZGAXRKVTAOI-UHFFFAOYSA-N 0.000 claims 1
• NWBMPJUVBNMTAZ-UHFFFAOYSA-N 1-[3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]pentan-1-one Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=CC(C(=O)CCCC)=CC=1NCCN1CCCC1 NWBMPJUVBNMTAZ-UHFFFAOYSA-N 0.000 claims 1
• BWMAIJPCEMKYSE-UHFFFAOYSA-N 1-[4-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 BWMAIJPCEMKYSE-UHFFFAOYSA-N 0.000 claims 1
• ANPOOPNQKGKSJT-UHFFFAOYSA-N 2-[2-chloro-4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-methylphenoxy]-n,n-dimethylethanamine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=C(OCCN(C)C)C=C1C ANPOOPNQKGKSJT-UHFFFAOYSA-N 0.000 claims 1
• AQSFKKRGCGBYMT-UHFFFAOYSA-N 2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C AQSFKKRGCGBYMT-UHFFFAOYSA-N 0.000 claims 1
• YTWXXVFTSISDIU-UHFFFAOYSA-N 2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]phenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 YTWXXVFTSISDIU-UHFFFAOYSA-N 0.000 claims 1
• QACFEEHLDHOROZ-UHFFFAOYSA-N 2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]phenoxy]-n-cyclopropylacetamide Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C(C=1)=CC=CC=1OCC(=O)NC1CC1 QACFEEHLDHOROZ-UHFFFAOYSA-N 0.000 claims 1
• SGXWCNICGLRKLH-UHFFFAOYSA-N 2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]phenoxy]-n-ethylacetamide Chemical compound CCNC(=O)COC1=CC=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 SGXWCNICGLRKLH-UHFFFAOYSA-N 0.000 claims 1
• UGBZDDLNHZCSGD-UHFFFAOYSA-N 2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]pyrazin-2-yl]oxy-n,n-dimethylethanamine Chemical compound CN(C)CCOC1=NC=CN=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 UGBZDDLNHZCSGD-UHFFFAOYSA-N 0.000 claims 1
• LQLOZXZBBRYWKZ-UHFFFAOYSA-N 2-[3-chloro-5-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]phenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1 LQLOZXZBBRYWKZ-UHFFFAOYSA-N 0.000 claims 1
• ZREYJYHNHLWXMG-UHFFFAOYSA-N 2-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-3,5,6-trifluoro-n-(3-methylbutyl)pyridin-4-amine Chemical compound CC(C)CCNC1=C(F)C(F)=NC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1F ZREYJYHNHLWXMG-UHFFFAOYSA-N 0.000 claims 1
• BYPWKEYKDJFHMZ-UHFFFAOYSA-N 2-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n,n-diethylpyrimidin-4-amine Chemical compound CCN(CC)C1=CC=NC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=N1 BYPWKEYKDJFHMZ-UHFFFAOYSA-N 0.000 claims 1
• HXUGITZLWUIORI-UHFFFAOYSA-N 2-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]benzonitrile Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC=C1C#N HXUGITZLWUIORI-UHFFFAOYSA-N 0.000 claims 1
• DJMBORBQCHGPTO-UHFFFAOYSA-N 2-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=NC=CC=C1C#N DJMBORBQCHGPTO-UHFFFAOYSA-N 0.000 claims 1
• NCQPMNLBSXIPKR-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C NCQPMNLBSXIPKR-UHFFFAOYSA-N 0.000 claims 1
• JJPWYGOOLUCARP-UHFFFAOYSA-N 2-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methoxyphenoxy]-n,n-dimethylethanamine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(OCCN(C)C)=C1OC JJPWYGOOLUCARP-UHFFFAOYSA-N 0.000 claims 1
• ZQWOIHWHSIPTIE-UHFFFAOYSA-N 2-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C ZQWOIHWHSIPTIE-UHFFFAOYSA-N 0.000 claims 1
• VEMYRWOPVSXONW-UHFFFAOYSA-N 2-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]-n,n-dimethylethanamine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(OCCN(C)C)=C1C VEMYRWOPVSXONW-UHFFFAOYSA-N 0.000 claims 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
• GTVUGPOLOIQVEI-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole-2-carboxylic acid Chemical compound C1CCC2CN(C(=O)O)CC21 GTVUGPOLOIQVEI-UHFFFAOYSA-N 0.000 claims 1
• IHRWZYGUYZIWKE-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C5OCOC5=CC=4)=NNC=3N=CN=2)CC1 IHRWZYGUYZIWKE-UHFFFAOYSA-N 0.000 claims 1
• RCPMWFKCKLHIEK-UHFFFAOYSA-N 3-(azetidin-3-ylidenemethyl)-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=C4CNC4)=NNC=3N=CN=2)CC1 RCPMWFKCKLHIEK-UHFFFAOYSA-N 0.000 claims 1
• SMJDOACCIIQIIV-GOSISDBHSA-N 3-[(2r)-4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-2-(hydroxymethyl)piperazin-1-yl]-4-methyl-n-phenylbenzamide Chemical compound C1=C(N2[C@H](CN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)CO)C(C)=CC=C1C(=O)NC1=CC=CC=C1 SMJDOACCIIQIIV-GOSISDBHSA-N 0.000 claims 1
• WLEVNSDEDNVUGR-INIZCTEOSA-N 3-[(2s)-4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-2-methylpiperazin-1-yl]-4-methyl-n-phenylbenzamide Chemical compound C([C@@H]1C)N(C=2C=3C(Br)=NNC=3N=CN=2)CCN1C(C(=CC=1)C)=CC=1C(=O)NC1=CC=CC=C1 WLEVNSDEDNVUGR-INIZCTEOSA-N 0.000 claims 1
• ODPLRDPJKWWTHJ-UHFFFAOYSA-N 3-[2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methylphenyl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCOC1=CC=CC=C1C1=CC=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 ODPLRDPJKWWTHJ-UHFFFAOYSA-N 0.000 claims 1
• DLMKOVRFSWGSNZ-UHFFFAOYSA-N 3-[2-chloro-4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-methylphenoxy]-n,n-dimethylpropan-1-amine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=C(OCCCN(C)C)C=C1C DLMKOVRFSWGSNZ-UHFFFAOYSA-N 0.000 claims 1
• IKUFFDDVPUPTCG-UHFFFAOYSA-N 3-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenoxy]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C IKUFFDDVPUPTCG-UHFFFAOYSA-N 0.000 claims 1
• SQMYBMIVKNUFRI-UHFFFAOYSA-N 3-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenyl]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C SQMYBMIVKNUFRI-UHFFFAOYSA-N 0.000 claims 1
• ASLBGEXQSXSLDI-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-2-oxopiperazin-1-yl]-4-methyl-n-phenylbenzamide Chemical compound C1=C(N2C(CN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=O)C(C)=CC=C1C(=O)NC1=CC=CC=C1 ASLBGEXQSXSLDI-UHFFFAOYSA-N 0.000 claims 1
• VWBUFACHINJXSO-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(2-methylpropoxy)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCC(C)C)=CC=1NCCN1CCCC1 VWBUFACHINJXSO-UHFFFAOYSA-N 0.000 claims 1
• JUZOYDZYOULNAP-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(2-phenylethyl)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(CCC=2C=CC=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 JUZOYDZYOULNAP-UHFFFAOYSA-N 0.000 claims 1
• WDWOGDISXRDAPH-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(3-methylbutoxy)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCCC(C)C)=CC=1NCCN1CCCC1 WDWOGDISXRDAPH-UHFFFAOYSA-N 0.000 claims 1
• XELODWMJEHJNGC-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound O1C(C)=NC(C=2C=C(C(C)=C(NCCN3CCCC3)C=2)N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=N1 XELODWMJEHJNGC-UHFFFAOYSA-N 0.000 claims 1
• BKZVKDVSFQWXCI-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(oxolan-2-ylmethoxy)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC2OCCC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 BKZVKDVSFQWXCI-UHFFFAOYSA-N 0.000 claims 1
• IHQZZYDEVZEHEN-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-phenyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(C=2C=CC=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 IHQZZYDEVZEHEN-UHFFFAOYSA-N 0.000 claims 1
• HEWBPXZYOYWXGF-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-propan-2-yloxy-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OC(C)C)=CC=1NCCN1CCCC1 HEWBPXZYOYWXGF-UHFFFAOYSA-N 0.000 claims 1
• CQAFUDZJKLZILE-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-propoxy-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCCC)=CC=1NCCN1CCCC1 CQAFUDZJKLZILE-UHFFFAOYSA-N 0.000 claims 1
• FQCOMPCVEBMBGQ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)-5-(1,3-thiazol-2-yl)aniline Chemical compound C1=C(C=2SC=CN=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 FQCOMPCVEBMBGQ-UHFFFAOYSA-N 0.000 claims 1
• HUSVBQWJEQARSD-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)-5-(2-trimethylsilylethyl)aniline Chemical compound C1=C(CC[Si](C)(C)C)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 HUSVBQWJEQARSD-UHFFFAOYSA-N 0.000 claims 1
• DAGQTIZIUNGONJ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)benzoic acid Chemical compound C1=C(C(O)=O)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 DAGQTIZIUNGONJ-UHFFFAOYSA-N 0.000 claims 1
• HJFUGUJMYAFXJJ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-n-phenylbenzamide Chemical compound C1=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=CC=C1C(=O)NC1=CC=CC=C1 HJFUGUJMYAFXJJ-UHFFFAOYSA-N 0.000 claims 1
• GKNWWGIEHPFKIG-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2-ethylbutoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCC(CC)CC)=CC=1NCCN1CCCC1 GKNWWGIEHPFKIG-UHFFFAOYSA-N 0.000 claims 1
• HROXMNKAOQUZSJ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2-fluoro-2-methylpropoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC(C)(C)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 HROXMNKAOQUZSJ-UHFFFAOYSA-N 0.000 claims 1
• FNHNYWBZBHUBPV-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2-methoxyethoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCCOC)=CC=1NCCN1CCCC1 FNHNYWBZBHUBPV-UHFFFAOYSA-N 0.000 claims 1
• GMJSCDCMWJNAQQ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(cyclopropylmethoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC2CC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 GMJSCDCMWJNAQQ-UHFFFAOYSA-N 0.000 claims 1
• AHLOJMPYPHADTE-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(difluoromethoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OC(F)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 AHLOJMPYPHADTE-UHFFFAOYSA-N 0.000 claims 1
• GIBOSPRQHDUWQU-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(difluoromethoxymethyl)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(COC(F)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 GIBOSPRQHDUWQU-UHFFFAOYSA-N 0.000 claims 1
• LDUJWILZFQEFOV-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-[2,3-difluoro-2-(fluoromethyl)propoxy]-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC(F)(CF)CF)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 LDUJWILZFQEFOV-UHFFFAOYSA-N 0.000 claims 1
• QQHQZRLEXUVJBO-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-[2-(dimethylamino)ethylamino]-4-methyl-n-phenylbenzamide Chemical compound C=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C(C)C(NCCN(C)C)=CC=1C(=O)NC1=CC=CC=C1 QQHQZRLEXUVJBO-UHFFFAOYSA-N 0.000 claims 1
• NFYLJFNABIOBQQ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-butoxy-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCCCC)=CC=1NCCN1CCCC1 NFYLJFNABIOBQQ-UHFFFAOYSA-N 0.000 claims 1
• IFJNCEJQABLDMF-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(Cl)=CC=1NCCN1CCCC1 IFJNCEJQABLDMF-UHFFFAOYSA-N 0.000 claims 1
• HNGORDVZNLENER-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-ethoxy-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCC)=CC=1NCCN1CCCC1 HNGORDVZNLENER-UHFFFAOYSA-N 0.000 claims 1
• UQPLUMXNXTZQMI-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-methoxy-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OC)=CC=1NCCN1CCCC1 UQPLUMXNXTZQMI-UHFFFAOYSA-N 0.000 claims 1
• SUPTVDNUUOFKOU-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n,4-dimethylbenzamide Chemical compound CNC(=O)C1=CC=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 SUPTVDNUUOFKOU-UHFFFAOYSA-N 0.000 claims 1
• XIQYNIPNCGZIBX-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n,n,4-trimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 XIQYNIPNCGZIBX-UHFFFAOYSA-N 0.000 claims 1
• SIODQEWTENYBSI-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-[2-(dimethylamino)ethyl]-4-methylbenzamide Chemical compound CN(C)CCNC(=O)C1=CC=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 SIODQEWTENYBSI-UHFFFAOYSA-N 0.000 claims 1
• ZYNKXHMLHGWMFA-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]pyrazine-2-carbonitrile Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=NC=CN=C1C#N ZYNKXHMLHGWMFA-UHFFFAOYSA-N 0.000 claims 1
• VGZTWRCQVSHEPS-UHFFFAOYSA-N 3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-phenylmethoxy-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C(=C(NCCN1CCCC1)C=1)C)=CC=1OCC1=CC=CC=C1 VGZTWRCQVSHEPS-UHFFFAOYSA-N 0.000 claims 1
• SVAZQZBAUSXFFJ-UHFFFAOYSA-N 3-[4-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-chloro-5-methylpyrimidin-2-yl]oxy-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCOC1=NC(Cl)=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=N1 SVAZQZBAUSXFFJ-UHFFFAOYSA-N 0.000 claims 1
• HBAHCSKBUFIZHI-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]aniline Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C(N)C=CC=4)=NNC=3N=CN=2)CC1 HBAHCSKBUFIZHI-UHFFFAOYSA-N 0.000 claims 1
• OSZPLABAQXTERJ-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C(C=CC=4)C(O)=O)=NNC=3N=CN=2)CC1 OSZPLABAQXTERJ-UHFFFAOYSA-N 0.000 claims 1
• DUZXKKRUOUCQRH-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]phenol Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C(O)C=CC=4)=NNC=3N=CN=2)CC1 DUZXKKRUOUCQRH-UHFFFAOYSA-N 0.000 claims 1
• MMMKUWNVQFPSJD-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]propan-1-ol Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(CCCO)=NNC=3N=CN=2)CC1 MMMKUWNVQFPSJD-UHFFFAOYSA-N 0.000 claims 1
• UGTLNWHSTJEXDT-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]propanoic acid Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(CCC(O)=O)=NNC=3N=CN=2)CC1 UGTLNWHSTJEXDT-UHFFFAOYSA-N 0.000 claims 1
• FZGQSPDGZYNZTQ-UHFFFAOYSA-N 3-[4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-yn-1-ol Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(C#CCO)=NNC=3N=CN=2)C(C)=C1CCCN1CCCC1 FZGQSPDGZYNZTQ-UHFFFAOYSA-N 0.000 claims 1
• HJONXTKKZWWBEI-UHFFFAOYSA-N 3-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenoxy]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C HJONXTKKZWWBEI-UHFFFAOYSA-N 0.000 claims 1
• WTMZIIWPBNLGSU-UHFFFAOYSA-N 3-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenyl]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C WTMZIIWPBNLGSU-UHFFFAOYSA-N 0.000 claims 1
• RZCJHYLETSBGLY-UHFFFAOYSA-N 3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C RZCJHYLETSBGLY-UHFFFAOYSA-N 0.000 claims 1
• JNHVUMXNINQBHC-UHFFFAOYSA-N 3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C JNHVUMXNINQBHC-UHFFFAOYSA-N 0.000 claims 1
• BPORTURMMAXOII-UHFFFAOYSA-N 3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n,n-dimethylprop-2-yn-1-amine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(C#CCN(C)C)=C1C BPORTURMMAXOII-UHFFFAOYSA-N 0.000 claims 1
• KVKOQBRWNARWNE-UHFFFAOYSA-N 3-[6-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-chloro-5-methylpyrimidin-4-yl]oxy-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCOC1=NC(Cl)=NC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C KVKOQBRWNARWNE-UHFFFAOYSA-N 0.000 claims 1
• CMNVIOXBVGGMHC-UHFFFAOYSA-N 3-bromo-4-(4-phenylpiperazin-1-yl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC=C1 CMNVIOXBVGGMHC-UHFFFAOYSA-N 0.000 claims 1
• BNTQQSCEOKZDMO-UHFFFAOYSA-N 3-bromo-4-(4-pyrazin-2-ylpiperazin-1-yl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=CN=CC=N1 BNTQQSCEOKZDMO-UHFFFAOYSA-N 0.000 claims 1
• QAZBUEIOUQSTLE-UHFFFAOYSA-N 3-bromo-4-(4-pyridin-2-ylpiperazin-1-yl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=CC=N1 QAZBUEIOUQSTLE-UHFFFAOYSA-N 0.000 claims 1
• ZNZOVFHYHATGSO-UHFFFAOYSA-N 3-bromo-4-(4-pyrimidin-2-ylpiperazin-1-yl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=NC=CC=N1 ZNZOVFHYHATGSO-UHFFFAOYSA-N 0.000 claims 1
• KHQIGQVSEDRIKJ-LLVKDONJSA-N 3-bromo-4-[(3r)-4-(5-chloro-2-methylphenyl)-3-methylpiperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C([C@H]1C)N(C=2C=3C(Br)=NNC=3N=CN=2)CCN1C1=CC(Cl)=CC=C1C KHQIGQVSEDRIKJ-LLVKDONJSA-N 0.000 claims 1
• KHQIGQVSEDRIKJ-NSHDSACASA-N 3-bromo-4-[(3s)-4-(5-chloro-2-methylphenyl)-3-methylpiperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C([C@@H]1C)N(C=2C=3C(Br)=NNC=3N=CN=2)CCN1C1=CC(Cl)=CC=C1C KHQIGQVSEDRIKJ-NSHDSACASA-N 0.000 claims 1
• HXDBVSLKASWNMX-UHFFFAOYSA-N 3-bromo-4-[3-methyl-4-(3-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1CN(C=2C=3C(Br)=NNC=3N=CN=2)CCN1C1=CC=CC(C)=C1 HXDBVSLKASWNMX-UHFFFAOYSA-N 0.000 claims 1
• HVADNQGYIAOGEP-UHFFFAOYSA-N 3-bromo-4-[4-(2,3-dichlorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=CC=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1Cl HVADNQGYIAOGEP-UHFFFAOYSA-N 0.000 claims 1
• RLQHIEAYRBMRRQ-UHFFFAOYSA-N 3-bromo-4-[4-(2,4-dichlorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=CC(Cl)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 RLQHIEAYRBMRRQ-UHFFFAOYSA-N 0.000 claims 1
• OTFFWCPPHHIFJB-UHFFFAOYSA-N 3-bromo-4-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound COC1=CC(OC)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 OTFFWCPPHHIFJB-UHFFFAOYSA-N 0.000 claims 1
• ZBVYWTDRJLQJFB-UHFFFAOYSA-N 3-bromo-4-[4-(2,4-dimethylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC(C)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 ZBVYWTDRJLQJFB-UHFFFAOYSA-N 0.000 claims 1
• GWRUURCRUCYCEF-UHFFFAOYSA-N 3-bromo-4-[4-(2,5-dichlorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=CC=C(Cl)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 GWRUURCRUCYCEF-UHFFFAOYSA-N 0.000 claims 1
• QKVBHDNWWHXBKQ-UHFFFAOYSA-N 3-bromo-4-[4-(2,6-dimethylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=CC(C)=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 QKVBHDNWWHXBKQ-UHFFFAOYSA-N 0.000 claims 1
• DWTODKDOZLKTNN-UHFFFAOYSA-N 3-bromo-4-[4-(2-ethylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CCC1=CC=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 DWTODKDOZLKTNN-UHFFFAOYSA-N 0.000 claims 1
• CQXAPCMYRSTDGK-UHFFFAOYSA-N 3-bromo-4-[4-(2-methoxyphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=C(Br)NN=C3N=CN=2)CC1 CQXAPCMYRSTDGK-UHFFFAOYSA-N 0.000 claims 1
• XFIJPNZKILCLOW-UHFFFAOYSA-N 3-bromo-4-[4-(2-nitrophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound [O-][N+](=O)C1=CC=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 XFIJPNZKILCLOW-UHFFFAOYSA-N 0.000 claims 1
• PZENQFNUARUTTQ-UHFFFAOYSA-N 3-bromo-4-[4-(3,4-dichlorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 PZENQFNUARUTTQ-UHFFFAOYSA-N 0.000 claims 1
• XOTIGRBKZQTNHN-UHFFFAOYSA-N 3-bromo-4-[4-(3,4-difluorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(F)C(F)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 XOTIGRBKZQTNHN-UHFFFAOYSA-N 0.000 claims 1
• IGLANVDJAXSNRA-UHFFFAOYSA-N 3-bromo-4-[4-(3,4-dimethylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(C)C(C)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 IGLANVDJAXSNRA-UHFFFAOYSA-N 0.000 claims 1
• VUOHNLSILKQOGZ-UHFFFAOYSA-N 3-bromo-4-[4-(3,5-dichlorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 VUOHNLSILKQOGZ-UHFFFAOYSA-N 0.000 claims 1
• NMMXPVBLDKUDAW-UHFFFAOYSA-N 3-bromo-4-[4-(3,5-dimethoxyphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 NMMXPVBLDKUDAW-UHFFFAOYSA-N 0.000 claims 1
• YKAMPLLTQDGYHQ-UHFFFAOYSA-N 3-bromo-4-[4-(3-chloro-4-fluorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C(F)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 YKAMPLLTQDGYHQ-UHFFFAOYSA-N 0.000 claims 1
• NJUZQTKLBLLKNB-UHFFFAOYSA-N 3-bromo-4-[4-(3-chlorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=CC=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 NJUZQTKLBLLKNB-UHFFFAOYSA-N 0.000 claims 1
• XKKYDENFHXAFLA-UHFFFAOYSA-N 3-bromo-4-[4-(3-methoxyphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound COC1=CC=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 XKKYDENFHXAFLA-UHFFFAOYSA-N 0.000 claims 1
• AJETWHHIDCIIFF-UHFFFAOYSA-N 3-bromo-4-[4-(3-methoxypyrazin-2-yl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound COC1=NC=CN=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 AJETWHHIDCIIFF-UHFFFAOYSA-N 0.000 claims 1
• GJFGRMNSKDWZCR-UHFFFAOYSA-N 3-bromo-4-[4-(4-bromophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=C(Br)C=C1 GJFGRMNSKDWZCR-UHFFFAOYSA-N 0.000 claims 1
• OARRIXBHAFQNGW-UHFFFAOYSA-N 3-bromo-4-[4-(4-ethoxyphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=CC(OCC)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 OARRIXBHAFQNGW-UHFFFAOYSA-N 0.000 claims 1
• CONWTRAMVJTTNB-UHFFFAOYSA-N 3-bromo-4-[4-(4-fluorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=CC(F)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 CONWTRAMVJTTNB-UHFFFAOYSA-N 0.000 claims 1
• CMSOTWVWWGTOCD-UHFFFAOYSA-N 3-bromo-4-[4-(4-nitrophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 CMSOTWVWWGTOCD-UHFFFAOYSA-N 0.000 claims 1
• MJTYOEDASCWGNL-UHFFFAOYSA-N 3-bromo-4-[4-(4-phenylmethoxyphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C(C=C1)=CC=C1OCC1=CC=CC=C1 MJTYOEDASCWGNL-UHFFFAOYSA-N 0.000 claims 1
• SHZNSNDAIKQSQV-UHFFFAOYSA-N 3-bromo-4-[4-[2-(trifluoromethyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound FC(F)(F)C1=CC=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 SHZNSNDAIKQSQV-UHFFFAOYSA-N 0.000 claims 1
• DCAOYMUUNJOKSB-UHFFFAOYSA-N 3-bromo-4-[4-[2-methyl-5-(2-methylpropoxy)-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCC(C)C)=CC=1CCCN1CCCC1 DCAOYMUUNJOKSB-UHFFFAOYSA-N 0.000 claims 1
• GZQAOQAIVFTXBT-UHFFFAOYSA-N 3-bromo-4-[4-[2-methyl-5-phenyl-3-(3-pyridin-1-ium-1-ylpropyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(C=2C=CC=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1CCC[N+]1=CC=CC=C1 GZQAOQAIVFTXBT-UHFFFAOYSA-N 0.000 claims 1
• JZMNQCWLQJMJJQ-UHFFFAOYSA-N 3-bromo-4-[4-[3-(2-piperidin-1-ylethoxy)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C(C=1)=CC=CC=1OCCN1CCCCC1 JZMNQCWLQJMJJQ-UHFFFAOYSA-N 0.000 claims 1
• GHUFQOINANIXTK-UHFFFAOYSA-N 3-bromo-4-[4-[3-(2-piperidin-1-ylethoxy)pyrazin-2-yl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=NC=CN=C1OCCN1CCCCC1 GHUFQOINANIXTK-UHFFFAOYSA-N 0.000 claims 1
• JLMAYHBMKURLET-UHFFFAOYSA-N 3-bromo-4-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 JLMAYHBMKURLET-UHFFFAOYSA-N 0.000 claims 1
• ULNFDXASZYQCIC-UHFFFAOYSA-N 3-bromo-4-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 ULNFDXASZYQCIC-UHFFFAOYSA-N 0.000 claims 1
• DGKZAYJXHQGDRL-UHFFFAOYSA-N 3-bromo-4-[4-[3-[(3-methylphenyl)methoxy]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=CC(COC=2C=C(C=CC=2)N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 DGKZAYJXHQGDRL-UHFFFAOYSA-N 0.000 claims 1
• WSFCJBDCDVWWPR-UHFFFAOYSA-N 3-bromo-4-[4-[3-bromo-5-[2,3-difluoro-2-(fluoromethyl)propoxy]-2-methylphenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=C(Br)C=C(OCC(F)(CF)CF)C=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 WSFCJBDCDVWWPR-UHFFFAOYSA-N 0.000 claims 1
• VBHFWMSSEZZUDB-UHFFFAOYSA-N 3-bromo-4-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=CC(C(F)(F)F)=CN=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 VBHFWMSSEZZUDB-UHFFFAOYSA-N 0.000 claims 1
• WTRRDUPRZHYBMD-UHFFFAOYSA-N 3-bromo-4-[4-[4-(furan-2-yl)pyrimidin-2-yl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C(N=1)=NC=CC=1C1=CC=CO1 WTRRDUPRZHYBMD-UHFFFAOYSA-N 0.000 claims 1
• RQVHKXWGBFPZNU-UHFFFAOYSA-N 3-bromo-4-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 RQVHKXWGBFPZNU-UHFFFAOYSA-N 0.000 claims 1
• NVNDCSVWPGQNIH-UHFFFAOYSA-N 3-bromo-4-[4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound FC(F)(F)C1=CC=NC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 NVNDCSVWPGQNIH-UHFFFAOYSA-N 0.000 claims 1
• GTOPXVPNCNNXLW-UHFFFAOYSA-N 3-bromo-4-[4-[4-(trifluoromethyl)pyrimidin-2-yl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound FC(F)(F)C1=CC=NC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=N1 GTOPXVPNCNNXLW-UHFFFAOYSA-N 0.000 claims 1
• UQXOTKGBLBLLEJ-UHFFFAOYSA-N 3-bromo-4-[4-[4-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C=C1OCCN1CCCC1 UQXOTKGBLBLLEJ-UHFFFAOYSA-N 0.000 claims 1
• FDYRBFONKISFFU-UHFFFAOYSA-N 3-bromo-4-[4-[4-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C=C1CCCN1CCCC1 FDYRBFONKISFFU-UHFFFAOYSA-N 0.000 claims 1
• JBRKDJZHLSVLLA-UHFFFAOYSA-N 3-bromo-4-[4-[5-[2,3-difluoro-2-(fluoromethyl)propoxy]-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(OCC(F)(CF)CF)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1CCCN1CCCC1 JBRKDJZHLSVLLA-UHFFFAOYSA-N 0.000 claims 1
• UOALCMPNVGOVDK-UHFFFAOYSA-N 3-bromo-4-[4-[5-[2,3-difluoro-2-(fluoromethyl)propoxy]-2-methylphenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(OCC(F)(CF)CF)C=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 UOALCMPNVGOVDK-UHFFFAOYSA-N 0.000 claims 1
• JHITWGOEXOEWQD-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-(2-piperidin-1-ylethoxy)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1OCCN1CCCCC1 JHITWGOEXOEWQD-UHFFFAOYSA-N 0.000 claims 1
• XPZWAIMVIPQEMM-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1OCCN1CCCC1 XPZWAIMVIPQEMM-UHFFFAOYSA-N 0.000 claims 1
• BKEGNPFOPJZHEG-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1CCCN1CCCCC1 BKEGNPFOPJZHEG-UHFFFAOYSA-N 0.000 claims 1
• MGZUHAQRVCAGIQ-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-[(1-methylpiperidin-4-yl)methoxy]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCC1COC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C MGZUHAQRVCAGIQ-UHFFFAOYSA-N 0.000 claims 1
• BWKXOAKSFYCWNB-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-[2-(1-methylpiperidin-4-yl)ethoxy]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCC1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C BWKXOAKSFYCWNB-UHFFFAOYSA-N 0.000 claims 1
• BXUHUHGWLOFGKA-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C BXUHUHGWLOFGKA-UHFFFAOYSA-N 0.000 claims 1
• RZIMJZUGEXCLDX-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-3-[2-(4-ethylpiperazin-1-yl)ethoxy]-2-methylphenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(CC)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C RZIMJZUGEXCLDX-UHFFFAOYSA-N 0.000 claims 1
• UZQJMNDBBURGNW-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-3-[3-(4-ethylpiperazin-1-yl)propoxy]-2-methylphenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(CC)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C UZQJMNDBBURGNW-UHFFFAOYSA-N 0.000 claims 1
• JRCOATCNMDGXOI-UHFFFAOYSA-N 3-bromo-4-[4-[5-fluoro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1CCCN1CCCC1 JRCOATCNMDGXOI-UHFFFAOYSA-N 0.000 claims 1
• MBYGSMUFVUTPIB-UHFFFAOYSA-N 3-bromo-5-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C(C=1)=CC(Br)=CC=1NCCN1CCCC1 MBYGSMUFVUTPIB-UHFFFAOYSA-N 0.000 claims 1
• RQVCBFVLFOELEY-UHFFFAOYSA-N 3-bromo-5-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-n-phenylbenzamide Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C(=C(Br)C=1)C)=CC=1C(=O)NC1=CC=CC=C1 RQVCBFVLFOELEY-UHFFFAOYSA-N 0.000 claims 1
• HYDOMGRCFKLOMU-UHFFFAOYSA-N 3-ethyl-4-[4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(C(F)(F)F)=CC=N1 HYDOMGRCFKLOMU-UHFFFAOYSA-N 0.000 claims 1
• CVMGWJJUNNHKEO-UHFFFAOYSA-N 3-methyl-4-[4-[4-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(C)=NNC2=NC=NC=1N(CC1)CCN1C(C=1)=CC=C(C)C=1OCCN1CCCC1 CVMGWJJUNNHKEO-UHFFFAOYSA-N 0.000 claims 1
• YIZQSXLPFSEWNO-UHFFFAOYSA-N 4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-1-(5-chloro-2-methylphenyl)piperazin-2-one Chemical compound CC1=CC=C(Cl)C=C1N1C(=O)CN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 YIZQSXLPFSEWNO-UHFFFAOYSA-N 0.000 claims 1
• VGARQGDBXVXNBU-UHFFFAOYSA-N 4-[2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenoxy]ethyl]morpholine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1OCCN1CCOCC1 VGARQGDBXVXNBU-UHFFFAOYSA-N 0.000 claims 1
• DDSNBPYIVBWXGB-UHFFFAOYSA-N 4-[2-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenoxy]ethyl]morpholine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1OCCN1CCOCC1 DDSNBPYIVBWXGB-UHFFFAOYSA-N 0.000 claims 1
• SDTLVFOPJADHPB-UHFFFAOYSA-N 4-[2-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]ethyl]morpholine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCOCC1 SDTLVFOPJADHPB-UHFFFAOYSA-N 0.000 claims 1
• XYOGGDREGYYWPA-UHFFFAOYSA-N 4-[3-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenyl]propyl]morpholine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1CCCN1CCOCC1 XYOGGDREGYYWPA-UHFFFAOYSA-N 0.000 claims 1
• HGBLQEPBGGAPAW-UHFFFAOYSA-N 4-[3-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenoxy]propyl]morpholine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1OCCCN1CCOCC1 HGBLQEPBGGAPAW-UHFFFAOYSA-N 0.000 claims 1
• ISQYTURYBKUOTA-UHFFFAOYSA-N 4-[3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]propyl]morpholine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1CCCN1CCOCC1 ISQYTURYBKUOTA-UHFFFAOYSA-N 0.000 claims 1
• KNOFIZHBESOPPI-UHFFFAOYSA-N 4-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-(trifluoromethyl)quinoline Chemical compound C1=CC=CC2=NC(C(F)(F)F)=CC(N3CCN(CC3)C=3C=4C(Br)=NNC=4N=CN=3)=C21 KNOFIZHBESOPPI-UHFFFAOYSA-N 0.000 claims 1
• TXVYVJXMZMPYMX-UHFFFAOYSA-N 4-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]benzonitrile Chemical compound C=12C(Br)=NNC2=NC=NC=1N(CC1)CCN1C1=CC=C(C#N)C=C1 TXVYVJXMZMPYMX-UHFFFAOYSA-N 0.000 claims 1
• LVOGLFHZHNTLSS-UHFFFAOYSA-N 4-[4-(3-bromo-5-chloro-2-methylphenyl)piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=C(Br)C=C(Cl)C=C1N1CCN(C=2C=3C=NNC=3N=C(N)N=2)CC1 LVOGLFHZHNTLSS-UHFFFAOYSA-N 0.000 claims 1
• BQQTTYBDFMEOIC-UHFFFAOYSA-N 4-[4-(3-chloro-5-methoxyphenyl)piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(OC)=C1 BQQTTYBDFMEOIC-UHFFFAOYSA-N 0.000 claims 1
• BVGJVMGHJXIGBN-UHFFFAOYSA-N 4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6,7-dimethoxyquinazoline Chemical compound COC1=C(OC)C=C2C(N3CCN(CC3)C=3N=CN=C4NN=C(C=34)CC)=NC=NC2=C1 BVGJVMGHJXIGBN-UHFFFAOYSA-N 0.000 claims 1
• WENXGABSSNOICL-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C=NNC=3N=C(N)N=2)CC1 WENXGABSSNOICL-UHFFFAOYSA-N 0.000 claims 1
• UWHHNRRWMAAGMX-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(1,2,3,6-tetrahydropyridin-4-yl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4CCNCC=4)=NNC=3N=CN=2)CC1 UWHHNRRWMAAGMX-UHFFFAOYSA-N 0.000 claims 1
• RFBBUGWLRAJCHK-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(2-methoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound COC1=CC=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 RFBBUGWLRAJCHK-UHFFFAOYSA-N 0.000 claims 1
• WSQDXQLVVHANFN-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-chloropyridin-4-yl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C(=CN=CC=4)Cl)=NNC=3N=CN=2)CC1 WSQDXQLVVHANFN-UHFFFAOYSA-N 0.000 claims 1
• VVEVCMUDDUYAPL-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-fluoropyridin-4-yl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C(=CN=CC=4)F)=NNC=3N=CN=2)CC1 VVEVCMUDDUYAPL-UHFFFAOYSA-N 0.000 claims 1
• ZKJQPYPFCFCZHX-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-methoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound COC1=CC=CC(C=2C3=C(N4CCN(CC4)C=4C(=CC=C(Cl)C=4)C)N=CN=C3NN=2)=C1 ZKJQPYPFCFCZHX-UHFFFAOYSA-N 0.000 claims 1
• OFGPMXXPBQRGQG-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-methylbut-2-enyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC=C(C)C)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C OFGPMXXPBQRGQG-UHFFFAOYSA-N 0.000 claims 1
• BMZLXAUYUKVRBT-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-phenylmethoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C(OCC=5C=CC=CC=5)C=CC=4)=NNC=3N=CN=2)CC1 BMZLXAUYUKVRBT-UHFFFAOYSA-N 0.000 claims 1
• WSDIKTCRDBJNEZ-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-pyrrolidin-1-ylpropyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(CCCN4CCCC4)=NNC=3N=CN=2)CC1 WSDIKTCRDBJNEZ-UHFFFAOYSA-N 0.000 claims 1
• WXIKPYIDNAJYKS-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-fluorophenyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(F)=CC=4)=NNC=3N=CN=2)CC1 WXIKPYIDNAJYKS-UHFFFAOYSA-N 0.000 claims 1
• HEMUMKTZPWGNKZ-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-methoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 HEMUMKTZPWGNKZ-UHFFFAOYSA-N 0.000 claims 1
• JKYFXFLTMOYKHE-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-methylphenyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 JKYFXFLTMOYKHE-UHFFFAOYSA-N 0.000 claims 1
• SABZWXMHVIATPL-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-phenoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(OC=5C=CC=CC=5)=CC=4)=NNC=3N=CN=2)CC1 SABZWXMHVIATPL-UHFFFAOYSA-N 0.000 claims 1
• WGLZMPRVECRUGN-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(piperidin-4-ylmethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(CC4CCNCC4)=NNC=3N=CN=2)CC1 WGLZMPRVECRUGN-UHFFFAOYSA-N 0.000 claims 1
• QZPJJGRIIWFHNP-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-[4-(piperidin-4-ylmethoxy)phenyl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(OCC5CCNCC5)=CC=4)=NNC=3N=CN=2)CC1 QZPJJGRIIWFHNP-UHFFFAOYSA-N 0.000 claims 1
• NNMOENYDTWNVJF-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-piperazin-1-yl-1h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(N4CCNCC4)=NNC=3N=CN=2)CC1 NNMOENYDTWNVJF-UHFFFAOYSA-N 0.000 claims 1
• LRXQPIKTVGCSCD-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-pyridin-4-yl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CN=CC=4)=NNC=3N=CN=2)CC1 LRXQPIKTVGCSCD-UHFFFAOYSA-N 0.000 claims 1
• BQVOBOKTPDRMQV-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-thiophen-2-yl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4SC=CC=4)=NNC=3N=CN=2)CC1 BQVOBOKTPDRMQV-UHFFFAOYSA-N 0.000 claims 1
• SFSIFSMOSDIXGP-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-n-phenyl-2h-pyrazolo[3,4-d]pyrimidin-3-amine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(NC=4C=CC=CC=4)=NNC=3N=CN=2)CC1 SFSIFSMOSDIXGP-UHFFFAOYSA-N 0.000 claims 1
• MXHFMCMHQFKAME-UHFFFAOYSA-N 4-[4-[2-chloro-5-(trifluoromethyl)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(C(F)(F)F)=CC=C1Cl MXHFMCMHQFKAME-UHFFFAOYSA-N 0.000 claims 1
• FVXRHCYOLHMKEG-UHFFFAOYSA-N 4-[4-[3-bromo-5-[2,3-difluoro-2-(fluoromethyl)propoxy]-2-methylphenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(OCC(F)(CF)CF)=CC(Br)=C1C FVXRHCYOLHMKEG-UHFFFAOYSA-N 0.000 claims 1
• BWDRROCFMQDWRM-UHFFFAOYSA-N 4-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]benzonitrile Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(=CC=4)C#N)=NNC=3N=CN=2)CC1 BWDRROCFMQDWRM-UHFFFAOYSA-N 0.000 claims 1
• PHMKLEPFJAIHGK-UHFFFAOYSA-N 4-[4-[4-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(N2CCN(CC2)C=2C=3C=NNC=3N=CN=2)C=C1OCCN1CCCC1 PHMKLEPFJAIHGK-UHFFFAOYSA-N 0.000 claims 1
• FIBUNCPXQUWYHP-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-piperidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1OCCN1CCCCC1 FIBUNCPXQUWYHP-UHFFFAOYSA-N 0.000 claims 1
• JFIJGHSUNBWBAL-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-piperidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCCC1 JFIJGHSUNBWBAL-UHFFFAOYSA-N 0.000 claims 1
• SWUHHIRFMYRIJB-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C=NNC=3N=CN=2)C(C)=C1OCCN1CCCC1 SWUHHIRFMYRIJB-UHFFFAOYSA-N 0.000 claims 1
• UPRIVIWOZLARIH-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-(2-methylpropyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC(C)C)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCC1 UPRIVIWOZLARIH-UHFFFAOYSA-N 0.000 claims 1
• BPGKERZGJLJMED-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1OCCN1CCCC1 BPGKERZGJLJMED-UHFFFAOYSA-N 0.000 claims 1
• VAPICOZQFYVJCT-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCC1 VAPICOZQFYVJCT-UHFFFAOYSA-N 0.000 claims 1
• WMDNCMBKBRUWNI-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-methyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(C)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCC1 WMDNCMBKBRUWNI-UHFFFAOYSA-N 0.000 claims 1
• IXFLVBJXEDPMNN-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-propan-2-yl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(C(C)C)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCC1 IXFLVBJXEDPMNN-UHFFFAOYSA-N 0.000 claims 1
• XBGWSDJSVVDITQ-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1OCCCN1CCCCC1 XBGWSDJSVVDITQ-UHFFFAOYSA-N 0.000 claims 1
• HFMZMDXFDNLWCB-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropyl)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1CCCN1CCCCC1 HFMZMDXFDNLWCB-UHFFFAOYSA-N 0.000 claims 1
• CCMZHPLGQJCYTC-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropyl)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1CCCN1CCCCC1 CCMZHPLGQJCYTC-UHFFFAOYSA-N 0.000 claims 1
• YNEHNQLNJHUVNL-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1OCCCN1CCCC1 YNEHNQLNJHUVNL-UHFFFAOYSA-N 0.000 claims 1
• MAWNYUYBGKUWRX-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C=NNC=3N=CN=2)C(C)=C1CCCN1CCCC1 MAWNYUYBGKUWRX-UHFFFAOYSA-N 0.000 claims 1
• ASGJAACMIIQVBB-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1CCCN1CCCC1 ASGJAACMIIQVBB-UHFFFAOYSA-N 0.000 claims 1
• KWKGHSHSXVOIQU-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1CCCN1CCCC1 KWKGHSHSXVOIQU-UHFFFAOYSA-N 0.000 claims 1
• LYIFKMWHZVCOEB-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[(1-methylpiperidin-4-yl)methoxy]phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCC1COC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C LYIFKMWHZVCOEB-UHFFFAOYSA-N 0.000 claims 1
• XCOVTQGGVHMDFB-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[2-(1-methylpiperidin-4-yl)ethoxy]phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCC1CCN(C)CC1 XCOVTQGGVHMDFB-UHFFFAOYSA-N 0.000 claims 1
• MREHXQMHLRHSEM-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C MREHXQMHLRHSEM-UHFFFAOYSA-N 0.000 claims 1
• XCFTYDOZRKVXNM-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCN(C)CC1 XCFTYDOZRKVXNM-UHFFFAOYSA-N 0.000 claims 1
• NMYJCDPLLFGHEJ-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C NMYJCDPLLFGHEJ-UHFFFAOYSA-N 0.000 claims 1
• RHHDBYUITDSZOI-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCCN1CCN(C)CC1 RHHDBYUITDSZOI-UHFFFAOYSA-N 0.000 claims 1
• IEGMLOPFLQNVPN-UHFFFAOYSA-N 4-[4-[5-chloro-3-[2-(4-ethylpiperazin-1-yl)ethoxy]-2-methylphenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(CC)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C IEGMLOPFLQNVPN-UHFFFAOYSA-N 0.000 claims 1
• DZFNNPOBVMURRI-UHFFFAOYSA-N 4-[4-[5-chloro-3-[2-(4-ethylpiperazin-1-yl)ethoxy]-2-methylphenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(CC)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C DZFNNPOBVMURRI-UHFFFAOYSA-N 0.000 claims 1
• ORHSSASUVVWACH-UHFFFAOYSA-N 4-[4-[5-chloro-3-[3-(4-ethylpiperazin-1-yl)propoxy]-2-methylphenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(CC)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C ORHSSASUVVWACH-UHFFFAOYSA-N 0.000 claims 1
• AFQIYWYPUWYCCT-UHFFFAOYSA-N 4-[4-[5-chloro-3-[3-(4-ethylpiperazin-1-yl)propoxy]-2-methylphenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(CC)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C AFQIYWYPUWYCCT-UHFFFAOYSA-N 0.000 claims 1
• YCUQWQAJXMRFNN-UHFFFAOYSA-N 5-[2,3-difluoro-2-(fluoromethyl)propoxy]-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(OCC(F)(CF)CF)=CC=1NCCN1CCCC1 YCUQWQAJXMRFNN-UHFFFAOYSA-N 0.000 claims 1
• JTLPCDMHGTVANG-UHFFFAOYSA-N 5-chloro-2-methyl-3-[4-(1h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 JTLPCDMHGTVANG-UHFFFAOYSA-N 0.000 claims 1
• CABOYHXJYNGXSR-UHFFFAOYSA-N 5-chloro-2-methyl-3-[4-(3-propan-2-yl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=12C(C(C)C)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1NCCN1CCCC1 CABOYHXJYNGXSR-UHFFFAOYSA-N 0.000 claims 1
• WVSOMLBCFGPONC-UHFFFAOYSA-N 5-chloro-2-methyl-3-[4-[3-(2-methylpropyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=12C(CC(C)C)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1NCCN1CCCC1 WVSOMLBCFGPONC-UHFFFAOYSA-N 0.000 claims 1
• ICZBXKGLNSAERJ-UHFFFAOYSA-N 5-chloro-3-[4-(3-cyclopropyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(C4CC4)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 ICZBXKGLNSAERJ-UHFFFAOYSA-N 0.000 claims 1
• IPSGJJMTWOHXNA-UHFFFAOYSA-N 5-fluoro-2-methyl-n-(2-pyrrolidin-1-ylethyl)-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]aniline Chemical compound C1=C(F)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1NCCN1CCCC1 IPSGJJMTWOHXNA-UHFFFAOYSA-N 0.000 claims 1
• FUZOXHWXAYGCHT-UHFFFAOYSA-N 6-[2-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]pyrimidin-4-yl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(C=3C=CN=C(N=3)N3CCN(CC3)C=3N=CN=C4NN=C(C=34)Br)=CC=C21 FUZOXHWXAYGCHT-UHFFFAOYSA-N 0.000 claims 1
• NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
• FTDNIAMWPZPKLR-UHFFFAOYSA-N [1-(3-chlorophenyl)-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-2-yl]methanol Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1CO)CCN1C1=CC=CC(Cl)=C1 FTDNIAMWPZPKLR-UHFFFAOYSA-N 0.000 claims 1
• QMSVBRCEGLXJLU-UHFFFAOYSA-N [3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]-phenylmethanone Chemical compound C1=C(C(=O)C=2C=CC=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 QMSVBRCEGLXJLU-UHFFFAOYSA-N 0.000 claims 1
• VQXJMCMQYVZVKB-UHFFFAOYSA-N [3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]-pyrrolidin-1-ylmethanone Chemical compound C1=C(C(=O)N2CCCC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 VQXJMCMQYVZVKB-UHFFFAOYSA-N 0.000 claims 1
• KXAKPLZFCFFJSW-UHFFFAOYSA-N [3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]methanol Chemical compound C1=C(CO)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 KXAKPLZFCFFJSW-UHFFFAOYSA-N 0.000 claims 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
• 150000002431 hydrogen Chemical class 0.000 claims 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
• PRGBKZSNTIVFOY-UHFFFAOYSA-N methyl 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 PRGBKZSNTIVFOY-UHFFFAOYSA-N 0.000 claims 1
• DUAMSJLUECLRIC-UHFFFAOYSA-N methyl 3-bromo-5-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC(Br)=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 DUAMSJLUECLRIC-UHFFFAOYSA-N 0.000 claims 1
• USXFGRUIDBDIFV-UHFFFAOYSA-N n,n-diethyl-2-[3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]phenoxy]ethanamine Chemical compound CCN(CC)CCOC1=CC=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1 USXFGRUIDBDIFV-UHFFFAOYSA-N 0.000 claims 1
• PMYOVPDVCABZJD-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(2-methylpropoxy)phenyl]-n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCNC1=CC(OCC(C)C)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C PMYOVPDVCABZJD-UHFFFAOYSA-N 0.000 claims 1
• OJFLWUQRQWXTTQ-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(2-methylpropoxy)phenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CC(C)COC1=CC(NCCN(C)C)=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 OJFLWUQRQWXTTQ-UHFFFAOYSA-N 0.000 claims 1
• GKIKAXFTSTUNIZ-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2-fluoro-2-methylpropoxy)-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC(OCC(C)(C)F)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C GKIKAXFTSTUNIZ-UHFFFAOYSA-N 0.000 claims 1
• JQNWZNUXLMFBJM-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-[2,3-difluoro-2-(fluoromethyl)propoxy]-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC(OCC(F)(CF)CF)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C JQNWZNUXLMFBJM-UHFFFAOYSA-N 0.000 claims 1
• HWKCACYJOZRVLP-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenyl]-n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C HWKCACYJOZRVLP-UHFFFAOYSA-N 0.000 claims 1
• GPNUVUGMFDKAJH-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C GPNUVUGMFDKAJH-UHFFFAOYSA-N 0.000 claims 1
• IBCUWWNXHJWZJO-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenyl]-n'-methyl-n'-propan-2-ylethane-1,2-diamine Chemical compound CC(C)N(C)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C IBCUWWNXHJWZJO-UHFFFAOYSA-N 0.000 claims 1
• CXRSSJQLJNMMKA-UHFFFAOYSA-N n-[4-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 CXRSSJQLJNMMKA-UHFFFAOYSA-N 0.000 claims 1
• ITLDDBHNZHKWPN-UHFFFAOYSA-N n-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenyl]-n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C ITLDDBHNZHKWPN-UHFFFAOYSA-N 0.000 claims 1
• BTHYNSZFAHGSOX-UHFFFAOYSA-N n-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C BTHYNSZFAHGSOX-UHFFFAOYSA-N 0.000 claims 1
• ACXREQVXILYMKB-UHFFFAOYSA-N n-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(NCCN(C)C)=C1C ACXREQVXILYMKB-UHFFFAOYSA-N 0.000 claims 1
• SPRYQHWIDYANOC-UHFFFAOYSA-N n-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n'-ethyl-n'-methylethane-1,2-diamine Chemical compound CCN(C)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C SPRYQHWIDYANOC-UHFFFAOYSA-N 0.000 claims 1
• OBOJJQBWMAPELI-UHFFFAOYSA-N n-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n'-methyl-n'-propan-2-ylethane-1,2-diamine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(NCCN(C)C(C)C)=C1C OBOJJQBWMAPELI-UHFFFAOYSA-N 0.000 claims 1
• LKQUCICFTHBFAL-UHFFFAOYSA-N n-benzylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NCC1=CC=CC=C1 LKQUCICFTHBFAL-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 379
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 374
• 238000005481 NMR spectroscopy Methods 0.000 description 304
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 140
• 235000019439 ethyl acetate Nutrition 0.000 description 128
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 108
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 91
• 239000000243 solution Substances 0.000 description 87
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
• 239000007787 solid Substances 0.000 description 78
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 77
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 69
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 66
• 229910052938 sodium sulfate Inorganic materials 0.000 description 65
• 235000011152 sodium sulphate Nutrition 0.000 description 65
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• 238000004440 column chromatography Methods 0.000 description 61
• 239000000377 silicon dioxide Substances 0.000 description 60
• 239000012267 brine Substances 0.000 description 55
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 55
• 239000012044 organic layer Substances 0.000 description 54
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 108010013238 70-kDa Ribosomal Protein S6 Kinases Proteins 0.000 description 43
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 43
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
• 125000001072 heteroaryl group Chemical group 0.000 description 38
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
• 239000003153 chemical reaction reagent Substances 0.000 description 35
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 30
• 239000003921 oil Substances 0.000 description 29
• 235000019198 oils Nutrition 0.000 description 29
• 230000027455 binding Effects 0.000 description 27
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 26
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
• 102000004169 proteins and genes Human genes 0.000 description 26
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
• 229910052799 carbon Inorganic materials 0.000 description 25
• 239000010410 layer Substances 0.000 description 25
• 235000018102 proteins Nutrition 0.000 description 25
• 108090000623 proteins and genes Proteins 0.000 description 25
• 125000005843 halogen group Chemical group 0.000 description 23
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
• 101100441092 Danio rerio crlf3 gene Proteins 0.000 description 20
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 20
• 206010028980 Neoplasm Diseases 0.000 description 19
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
• 235000019341 magnesium sulphate Nutrition 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 150000003254 radicals Chemical class 0.000 description 18
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 17
• 210000004027 cell Anatomy 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 17
• 239000000126 substance Substances 0.000 description 17
• 125000000753 cycloalkyl group Chemical group 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 16
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
• 239000000460 chlorine Substances 0.000 description 15
• 238000006467 substitution reaction Methods 0.000 description 15
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
• 125000004429 atom Chemical group 0.000 description 14
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 14
• 229910000024 caesium carbonate Inorganic materials 0.000 description 14
• 235000019441 ethanol Nutrition 0.000 description 14
• 239000003446 ligand Substances 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
• 238000000746 purification Methods 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
• 201000011510 cancer Diseases 0.000 description 12
• 238000004007 reversed phase HPLC Methods 0.000 description 12
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
• 235000017557 sodium bicarbonate Nutrition 0.000 description 12
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• 201000009030 Carcinoma Diseases 0.000 description 11
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
• 238000003556 assay Methods 0.000 description 11
• 108020001756 ligand binding domains Proteins 0.000 description 11
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 11
• 239000003814 drug Substances 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• 208000009956 adenocarcinoma Diseases 0.000 description 9
• 239000012230 colorless oil Substances 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 102000005962 receptors Human genes 0.000 description 9
• 108020003175 receptors Proteins 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• 206010039491 Sarcoma Diseases 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 125000002947 alkylene group Chemical group 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 8
• 229940079593 drug Drugs 0.000 description 8
• 125000004043 oxo group Chemical group O=* 0.000 description 8
• 229940002612 prodrug Drugs 0.000 description 8
• 239000000651 prodrug Substances 0.000 description 8
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 8
• 238000011282 treatment Methods 0.000 description 8
• 206010025323 Lymphomas Diseases 0.000 description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• 125000001118 alkylidene group Chemical group 0.000 description 7
• 235000015165 citric acid Nutrition 0.000 description 7
• 238000005094 computer simulation Methods 0.000 description 7
• 206010016629 fibroma Diseases 0.000 description 7
• QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• FVDJRHNUZNLRJC-UHFFFAOYSA-N 1-(5-chloro-2-methylphenyl)piperazine Chemical compound CC1=CC=C(Cl)C=C1N1CCNCC1 FVDJRHNUZNLRJC-UHFFFAOYSA-N 0.000 description 6
• WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 6
• QIXXACAFRCQPFS-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)piperazin-1-yl]-7h-purine Chemical class ClC1=CC=CC(N2CCN(CC2)C=2C=3NC=NC=3N=CN=2)=C1 QIXXACAFRCQPFS-UHFFFAOYSA-N 0.000 description 6
• MBRQCVJHJOVNLO-UHFFFAOYSA-N 6-[4-(4-fluorophenyl)piperazin-1-yl]-7h-purine Chemical compound C1=CC(F)=CC=C1N1CCN(C=2C=3NC=NC=3N=CN=2)CC1 MBRQCVJHJOVNLO-UHFFFAOYSA-N 0.000 description 6
• ICAARADRKONXBF-UHFFFAOYSA-N 6-[4-(4-methoxyphenyl)piperazin-1-yl]-7h-purine Chemical class C1=CC(OC)=CC=C1N1CCN(C=2C=3NC=NC=3N=CN=2)CC1 ICAARADRKONXBF-UHFFFAOYSA-N 0.000 description 6
• 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 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• 239000007821 HATU Substances 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 238000004590 computer program Methods 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 239000012065 filter cake Substances 0.000 description 6
• 238000013508 migration Methods 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 125000005415 substituted alkoxy group Chemical group 0.000 description 6
• 230000004614 tumor growth Effects 0.000 description 6
• LCGMENDABLGZBC-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)piperazin-1-yl]-1h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=CC=CC(N2CCN(CC2)C=2C=3C=NNC=3N=CN=2)=C1 LCGMENDABLGZBC-UHFFFAOYSA-N 0.000 description 5
• WAIMQUPDNQRLKD-UHFFFAOYSA-N 4-chloro-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC(Cl)=C2C(CC)=NNC2=N1 WAIMQUPDNQRLKD-UHFFFAOYSA-N 0.000 description 5
• HCGWOUNUNZPMMV-UHFFFAOYSA-N 6-(4-pyrimidin-2-ylpiperazin-1-yl)-7h-purine Chemical compound C1CN(C=2C=3NC=NC=3N=CN=2)CCN1C1=NC=CC=N1 HCGWOUNUNZPMMV-UHFFFAOYSA-N 0.000 description 5
• SSXSBIJYAWHOSQ-UHFFFAOYSA-N 6-[4-(2,5-dimethylphenyl)piperazin-1-yl]-7h-purine Chemical compound CC1=CC=C(C)C(N2CCN(CC2)C=2C=3NC=NC=3N=CN=2)=C1 SSXSBIJYAWHOSQ-UHFFFAOYSA-N 0.000 description 5
• ZMJKIUCPJALXPF-UHFFFAOYSA-N 6-[4-(2-fluorophenyl)piperazin-1-yl]-7h-purine Chemical class FC1=CC=CC=C1N1CCN(C=2C=3NC=NC=3N=CN=2)CC1 ZMJKIUCPJALXPF-UHFFFAOYSA-N 0.000 description 5
• QVBFELMJIOAJLK-UHFFFAOYSA-N 6-[4-(3,4-dichlorophenyl)piperazin-1-yl]-7h-purine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCN(C=2C=3NC=NC=3N=CN=2)CC1 QVBFELMJIOAJLK-UHFFFAOYSA-N 0.000 description 5
• AQKCWTXVJVQGDX-UHFFFAOYSA-N 6-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]-7h-purine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC2)C=2C=3NC=NC=3N=CN=2)=C1 AQKCWTXVJVQGDX-UHFFFAOYSA-N 0.000 description 5
• 241000124008 Mammalia Species 0.000 description 5
• 201000004681 Psoriasis Diseases 0.000 description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 5
• 229960000583 acetic acid Drugs 0.000 description 5
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 5
• 230000004071 biological effect Effects 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 230000010261 cell growth Effects 0.000 description 5
• 230000004663 cell proliferation Effects 0.000 description 5
• 239000000284 extract Substances 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 239000006260 foam Substances 0.000 description 5
• 239000005457 ice water Substances 0.000 description 5
• 238000004519 manufacturing process Methods 0.000 description 5
• 208000030159 metabolic disease Diseases 0.000 description 5
• 239000002207 metabolite Substances 0.000 description 5
• WAVOFQCBZGBMFX-UHFFFAOYSA-N methanesulfonic acid;6-[4-(2-methoxyphenyl)piperazin-1-yl]-7h-purine Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(C=2C=3NC=NC=3N=CN=2)CC1 WAVOFQCBZGBMFX-UHFFFAOYSA-N 0.000 description 5
• 230000005012 migration Effects 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 230000035755 proliferation Effects 0.000 description 5
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 5
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 5
• 230000011664 signaling Effects 0.000 description 5
• 239000011780 sodium chloride Substances 0.000 description 5
• 125000003003 spiro group Chemical group 0.000 description 5
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 4
• KDYPEARPZJFJBV-UHFFFAOYSA-N 6-[4-(2-chlorophenyl)piperazin-1-yl]-7h-purine Chemical compound ClC1=CC=CC=C1N1CCN(C=2C=3NC=NC=3N=CN=2)CC1 KDYPEARPZJFJBV-UHFFFAOYSA-N 0.000 description 4
• KWLXRQFZEOGTIH-UHFFFAOYSA-N 6-[4-(2-methoxyphenyl)piperazin-1-yl]-7h-purine Chemical compound COC1=CC=CC=C1N1CCN(C=2C=3NC=NC=3N=CN=2)CC1 KWLXRQFZEOGTIH-UHFFFAOYSA-N 0.000 description 4
• LTKVADSFDKAFCU-UHFFFAOYSA-N 6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-7h-purine Chemical compound FC(F)(F)C1=CC=CN=C1N1CCN(C=2C=3NC=NC=3N=CN=2)CC1 LTKVADSFDKAFCU-UHFFFAOYSA-N 0.000 description 4
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
• 239000005711 Benzoic acid Substances 0.000 description 4
• 229910014265 BrCl Inorganic materials 0.000 description 4
• 102000004190 Enzymes Human genes 0.000 description 4
• 108090000790 Enzymes Proteins 0.000 description 4
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
• 241000282412 Homo Species 0.000 description 4
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
• 102000038030 PI3Ks Human genes 0.000 description 4
• 108091007960 PI3Ks Proteins 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 4
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 4
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 4
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 4
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 4
• 239000002671 adjuvant Substances 0.000 description 4
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
• 235000008206 alpha-amino acids Nutrition 0.000 description 4
• 235000010233 benzoic acid Nutrition 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 4
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
• 150000001721 carbon Chemical class 0.000 description 4
• 230000001419 dependent effect Effects 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 230000014509 gene expression Effects 0.000 description 4
• 235000011187 glycerol Nutrition 0.000 description 4
• 201000011066 hemangioma Diseases 0.000 description 4
• 238000011534 incubation Methods 0.000 description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 230000004060 metabolic process Effects 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 239000002480 mineral oil Substances 0.000 description 4
• 235000010446 mineral oil Nutrition 0.000 description 4
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
• 229910052760 oxygen Inorganic materials 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• 206010041823 squamous cell carcinoma Diseases 0.000 description 4
• 229910052717 sulfur Inorganic materials 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• 239000006188 syrup Substances 0.000 description 4
• 235000020357 syrup Nutrition 0.000 description 4
• 229960004441 tyrosine Drugs 0.000 description 4
• 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 4
• YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 description 3
• JHIWJXNUTCUPEF-UHFFFAOYSA-N 6-(4-phenylpiperazin-1-yl)-7h-purine Chemical compound C1CN(C=2C=3NC=NC=3N=CN=2)CCN1C1=CC=CC=C1 JHIWJXNUTCUPEF-UHFFFAOYSA-N 0.000 description 3
• WTNDAPKCZINZQI-UHFFFAOYSA-N 6-(4-pyridin-2-ylpiperazin-1-yl)-7h-purine Chemical compound C1CN(C=2C=3NC=NC=3N=CN=2)CCN1C1=CC=CC=N1 WTNDAPKCZINZQI-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 206010012689 Diabetic retinopathy Diseases 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 108700020796 Oncogene Proteins 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 description 3
• 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 3
• 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 3
• 239000002202 Polyethylene glycol Substances 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
• 229920002472 Starch Polymers 0.000 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• 206010043276 Teratoma Diseases 0.000 description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
• 125000004414 alkyl thio group Chemical group 0.000 description 3
• 125000000304 alkynyl group Chemical group 0.000 description 3
• 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 3
• 150000001408 amides Chemical group 0.000 description 3
• 230000033115 angiogenesis Effects 0.000 description 3
• 230000006907 apoptotic process Effects 0.000 description 3
• 239000012298 atmosphere Substances 0.000 description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 3
• 229960002903 benzyl benzoate Drugs 0.000 description 3
• 239000011230 binding agent Substances 0.000 description 3
• 230000036983 biotransformation Effects 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 235000008504 concentrate Nutrition 0.000 description 3
• 239000012141 concentrate Substances 0.000 description 3
• 235000005911 diet Nutrition 0.000 description 3
• 230000037213 diet Effects 0.000 description 3
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 229940000406 drug candidate Drugs 0.000 description 3
• 238000009510 drug design Methods 0.000 description 3
• 239000003995 emulsifying agent Substances 0.000 description 3
• 230000001605 fetal effect Effects 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 239000012362 glacial acetic acid Substances 0.000 description 3
• 125000001188 haloalkyl group Chemical group 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
• YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 3
• 239000003112 inhibitor Substances 0.000 description 3
• 230000005764 inhibitory process Effects 0.000 description 3
• 238000002372 labelling Methods 0.000 description 3
• 206010027191 meningioma Diseases 0.000 description 3
• 229940098779 methanesulfonic acid Drugs 0.000 description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
• 208000008798 osteoma Diseases 0.000 description 3
• 230000003647 oxidation Effects 0.000 description 3
• 238000007254 oxidation reaction Methods 0.000 description 3
• 239000001301 oxygen Substances 0.000 description 3
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
• 230000026731 phosphorylation Effects 0.000 description 3
• 238000006366 phosphorylation reaction Methods 0.000 description 3
• 239000006187 pill Substances 0.000 description 3
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
• 108090000765 processed proteins & peptides Proteins 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• 239000007909 solid dosage form Substances 0.000 description 3
• 235000019698 starch Nutrition 0.000 description 3
• 239000008107 starch Substances 0.000 description 3
• 229940032147 starch Drugs 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• 239000000829 suppository Substances 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
• 108010072897 transcription factor Brn-2 Proteins 0.000 description 3
• 230000014616 translation Effects 0.000 description 3
• 239000000080 wetting agent Substances 0.000 description 3
• YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
• ANSSPNJBAYQWRK-UHFFFAOYSA-N (3-bromo-5-chloro-2-methoxyphenyl)methanol Chemical compound COC1=C(Br)C=C(Cl)C=C1CO ANSSPNJBAYQWRK-UHFFFAOYSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• HCSPSOHASPVBNM-UHFFFAOYSA-N 1,3-dibromo-5-(2-ethylbutoxy)-2-methylbenzene Chemical compound CCC(CC)COC1=CC(Br)=C(C)C(Br)=C1 HCSPSOHASPVBNM-UHFFFAOYSA-N 0.000 description 2
• YWTLSQDOONKMOJ-UHFFFAOYSA-N 1,3-dibromo-5-ethylsulfonyl-2-methylbenzene Chemical compound CCS(=O)(=O)C1=CC(Br)=C(C)C(Br)=C1 YWTLSQDOONKMOJ-UHFFFAOYSA-N 0.000 description 2
• LZWVTQKAHFBVJA-UHFFFAOYSA-N 1,3-dichloro-5-phenylmethoxybenzene Chemical compound ClC1=CC(Cl)=CC(OCC=2C=CC=CC=2)=C1 LZWVTQKAHFBVJA-UHFFFAOYSA-N 0.000 description 2
• LLKMJMQVKKJDAT-UHFFFAOYSA-N 1-(2-methyl-3-phenylmethoxyphenyl)piperazine Chemical compound C1=CC=C(N2CCNCC2)C(C)=C1OCC1=CC=CC=C1 LLKMJMQVKKJDAT-UHFFFAOYSA-N 0.000 description 2
• GMWFVNNUKZUKHT-UHFFFAOYSA-N 1-(3-chloro-4-phenylmethoxyphenyl)piperazine Chemical compound ClC1=CC(N2CCNCC2)=CC=C1OCC1=CC=CC=C1 GMWFVNNUKZUKHT-UHFFFAOYSA-N 0.000 description 2
• YKCMSKWIWGCSLG-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-[(2-methylpropan-2-yl)oxycarbonyl]piperazine-2-carboxylic acid Chemical compound OC(=O)C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC(Cl)=C1 YKCMSKWIWGCSLG-UHFFFAOYSA-N 0.000 description 2
• AYGSSBGDRWWJRM-UHFFFAOYSA-N 1-(5-chloro-2-methyl-4-phenylmethoxyphenyl)piperazine Chemical compound ClC=1C=C(N2CCNCC2)C(C)=CC=1OCC1=CC=CC=C1 AYGSSBGDRWWJRM-UHFFFAOYSA-N 0.000 description 2
• UXKTVCRKUQMRIM-UHFFFAOYSA-N 1-(5-chloro-3-iodo-2-methylphenyl)piperazine Chemical compound CC1=C(I)C=C(Cl)C=C1N1CCNCC1 UXKTVCRKUQMRIM-UHFFFAOYSA-N 0.000 description 2
• VNSZFUHIYFCNBA-UHFFFAOYSA-N 1-[3-piperazin-1-yl-5-(2-pyrrolidin-1-ylethylamino)phenyl]butan-1-one;hydrochloride Chemical compound Cl.C=1C(N2CCNCC2)=CC(C(=O)CCC)=CC=1NCCN1CCCC1 VNSZFUHIYFCNBA-UHFFFAOYSA-N 0.000 description 2
• GNJFDVMDZRSYSH-UHFFFAOYSA-N 1-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazine Chemical compound C1=C(Cl)C=C(N2CCNCC2)C(C)=C1CCCN1CCCC1 GNJFDVMDZRSYSH-UHFFFAOYSA-N 0.000 description 2
• HHQMROZCVARUAG-UHFFFAOYSA-N 1-bromopropane;magnesium Chemical compound [Mg].CCCBr HHQMROZCVARUAG-UHFFFAOYSA-N 0.000 description 2
• LGJGKSIGZJWWOU-UHFFFAOYSA-N 1-chloro-4-methyl-5-nitroso-2-phenylmethoxybenzene Chemical compound C1=C(N=O)C(C)=CC(OCC=2C=CC=CC=2)=C1Cl LGJGKSIGZJWWOU-UHFFFAOYSA-N 0.000 description 2
• IYFXPOWQFWHFNO-UHFFFAOYSA-N 1-chloro-4-methyl-6-phenylmethoxycyclohexa-2,4-dien-1-amine Chemical compound NC1(Cl)C=CC(C)=CC1OCC1=CC=CC=C1 IYFXPOWQFWHFNO-UHFFFAOYSA-N 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• LRRBSBYKUDBUCC-UHFFFAOYSA-N 1-tert-butyl-4-chloro-3-(trifluoromethyl)pyrazolo[3,4-d]pyrimidine Chemical compound N1=CN=C2N(C(C)(C)C)N=C(C(F)(F)F)C2=C1Cl LRRBSBYKUDBUCC-UHFFFAOYSA-N 0.000 description 2
• JQNOTRRYTBGTRR-UHFFFAOYSA-N 2-(1-hydroxybutylidene)propanedinitrile Chemical compound CCCC(O)=C(C#N)C#N JQNOTRRYTBGTRR-UHFFFAOYSA-N 0.000 description 2
• HNNJMJWOSXHEJJ-UHFFFAOYSA-N 2-(1-methoxybutylidene)propanedinitrile Chemical compound CCCC(OC)=C(C#N)C#N HNNJMJWOSXHEJJ-UHFFFAOYSA-N 0.000 description 2
• VEXSEQYCQCWPKC-UHFFFAOYSA-N 2-(3-bromo-5-chloro-2-methoxyphenoxy)-n,n-dimethylethanamine Chemical compound COC1=C(Br)C=C(Cl)C=C1OCCN(C)C VEXSEQYCQCWPKC-UHFFFAOYSA-N 0.000 description 2
• AHGXQMBEGNIIFZ-UHFFFAOYSA-N 2-(5-chloro-2-methoxy-3-piperazin-1-ylphenoxy)-n,n-dimethylethanamine Chemical compound COC1=C(OCCN(C)C)C=C(Cl)C=C1N1CCNCC1 AHGXQMBEGNIIFZ-UHFFFAOYSA-N 0.000 description 2
• UTKFOTINIHYUNG-UHFFFAOYSA-N 2-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.CN(C)CCOC1=CC(Cl)=CC(N2CCNCC2)=C1C UTKFOTINIHYUNG-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• GQRCTVZXQLUDBU-UHFFFAOYSA-N 2-[1-methoxy-2-(2-methoxyethoxy)ethylidene]propanedinitrile Chemical compound COCCOCC(OC)=C(C#N)C#N GQRCTVZXQLUDBU-UHFFFAOYSA-N 0.000 description 2
• FXECOYYRPDGOQB-UHFFFAOYSA-N 2-chloro-4-piperazin-1-ylphenol Chemical compound C1=C(Cl)C(O)=CC=C1N1CCNCC1 FXECOYYRPDGOQB-UHFFFAOYSA-N 0.000 description 2
• GRDWXOLMJKVABV-UHFFFAOYSA-N 2-chloro-5-methyl-4-piperazin-1-ylphenol Chemical compound CC1=CC(O)=C(Cl)C=C1N1CCNCC1 GRDWXOLMJKVABV-UHFFFAOYSA-N 0.000 description 2
• RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 2
• LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 2
• PBSZHNXXFIYDBU-UHFFFAOYSA-N 2-methyl-1-nitro-3-phenylmethoxybenzene Chemical compound C1=CC=C([N+]([O-])=O)C(C)=C1OCC1=CC=CC=C1 PBSZHNXXFIYDBU-UHFFFAOYSA-N 0.000 description 2
• IHMXLABJHKKMTC-UHFFFAOYSA-N 2-methyl-3-phenylmethoxyaniline Chemical compound CC1=C(N)C=CC=C1OCC1=CC=CC=C1 IHMXLABJHKKMTC-UHFFFAOYSA-N 0.000 description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• LOWZPOSKBWZMFN-UHFFFAOYSA-N 3,5-dibromo-4-methylbenzenethiol Chemical compound CC1=C(Br)C=C(S)C=C1Br LOWZPOSKBWZMFN-UHFFFAOYSA-N 0.000 description 2
• SVMOURXLHJYDSL-UHFFFAOYSA-N 3-(2-methoxyethoxymethyl)-1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC(O)=C2C(COCCOC)=NNC2=N1 SVMOURXLHJYDSL-UHFFFAOYSA-N 0.000 description 2
• YAZKUAAGEAVPOX-UHFFFAOYSA-N 3-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CCCC1=CC(Cl)=CC(N2CCNCC2)=C1C YAZKUAAGEAVPOX-UHFFFAOYSA-N 0.000 description 2
• WRNMWJANSIWPSO-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2-ethylbutoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCC(CC)CC)=CC=1NCCN1CCCC1 WRNMWJANSIWPSO-UHFFFAOYSA-N 0.000 description 2
• PIKTZPAJHCXGGM-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]propan-1-ol;2,2,2-trifluoroacetic acid Chemical class OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C3=C(CCCO)NN=C3N=CN=2)CC1 PIKTZPAJHCXGGM-UHFFFAOYSA-N 0.000 description 2
• QFXGCRQDTNRNMY-UHFFFAOYSA-N 3-amino-5-(2-methoxyethoxymethyl)-1h-pyrazole-4-carbonitrile Chemical compound COCCOCC1=NNC(N)=C1C#N QFXGCRQDTNRNMY-UHFFFAOYSA-N 0.000 description 2
• YWRKFBPYSYYYMN-UHFFFAOYSA-N 3-amino-5-propyl-1h-pyrazole-4-carbonitrile Chemical compound CCCC1=NNC(N)=C1C#N YWRKFBPYSYYYMN-UHFFFAOYSA-N 0.000 description 2
• DGAWZKMBSUKIKI-UHFFFAOYSA-N 3-bromo-4-methyl-5-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]benzoic acid Chemical compound CC1=C(Br)C=C(C(O)=O)C=C1N1CCN(C(=O)OC(C)(C)C)CC1 DGAWZKMBSUKIKI-UHFFFAOYSA-N 0.000 description 2
• LVLKZFYISQEUFL-UHFFFAOYSA-N 3-bromo-4-methyl-n-phenyl-5-piperazin-1-ylbenzamide;hydrochloride Chemical compound Cl.CC1=C(Br)C=C(C(=O)NC=2C=CC=CC=2)C=C1N1CCNCC1 LVLKZFYISQEUFL-UHFFFAOYSA-N 0.000 description 2
• WMHPXUMZJOUCSK-UHFFFAOYSA-N 3-bromo-5-chloro-2-methoxybenzaldehyde Chemical compound COC1=C(Br)C=C(Cl)C=C1C=O WMHPXUMZJOUCSK-UHFFFAOYSA-N 0.000 description 2
• ZCIWNGLMYMAPGX-UHFFFAOYSA-N 3-bromo-5-chloro-2-methoxyphenol Chemical compound COC1=C(O)C=C(Cl)C=C1Br ZCIWNGLMYMAPGX-UHFFFAOYSA-N 0.000 description 2
• PTKLDNPKLLKELG-UHFFFAOYSA-N 3-chloro-5-piperazin-1-ylphenol Chemical compound OC1=CC(Cl)=CC(N2CCNCC2)=C1 PTKLDNPKLLKELG-UHFFFAOYSA-N 0.000 description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• XFQRTMDBKVVAHL-UHFFFAOYSA-N 3-propyl-1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC(O)=C2C(CCC)=NNC2=N1 XFQRTMDBKVVAHL-UHFFFAOYSA-N 0.000 description 2
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• RGNRJRKMSRGMHQ-UHFFFAOYSA-N 4-[2-(2-chloro-4-piperazin-1-ylphenoxy)ethyl]morpholine;hydrochloride Chemical compound Cl.ClC1=CC(N2CCNCC2)=CC=C1OCCN1CCOCC1 RGNRJRKMSRGMHQ-UHFFFAOYSA-N 0.000 description 2
• ZWXDAGFKCZMYTQ-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-piperazin-1-yl-1h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(N4CCNCC4)=NNC=3N=CN=2)CC1 ZWXDAGFKCZMYTQ-UHFFFAOYSA-N 0.000 description 2
• RUVDUIQMBVBZFS-UHFFFAOYSA-N 4-bromo-2-chloro-1-phenylmethoxybenzene Chemical compound ClC1=CC(Br)=CC=C1OCC1=CC=CC=C1 RUVDUIQMBVBZFS-UHFFFAOYSA-N 0.000 description 2
• IOMPADPEBLABRM-UHFFFAOYSA-N 4-chloro-3-(2-methoxyethoxymethyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC(Cl)=C2C(COCCOC)=NNC2=N1 IOMPADPEBLABRM-UHFFFAOYSA-N 0.000 description 2
• XFDFMJYQFBHDMF-UHFFFAOYSA-N 4-chloro-3-methyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC(Cl)=C2C(C)=NNC2=N1 XFDFMJYQFBHDMF-UHFFFAOYSA-N 0.000 description 2
• ZUCMUUMUEOALJU-UHFFFAOYSA-N 4-chloro-3-phenyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=2C(Cl)=NC=NC=2NN=C1C1=CC=CC=C1 ZUCMUUMUEOALJU-UHFFFAOYSA-N 0.000 description 2
• FMJNJDVLTSSZHB-UHFFFAOYSA-N 4-chloro-3-propyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC(Cl)=C2C(CCC)=NNC2=N1 FMJNJDVLTSSZHB-UHFFFAOYSA-N 0.000 description 2
• PMZODXFLGOEQQR-UHFFFAOYSA-N 4-chloro-n-phenyl-2h-pyrazolo[3,4-d]pyrimidin-3-amine Chemical compound C1=2C(Cl)=NC=NC=2NN=C1NC1=CC=CC=C1 PMZODXFLGOEQQR-UHFFFAOYSA-N 0.000 description 2
• FUQMYXHATNHEBU-UHFFFAOYSA-N 4-methyl-3-[2-pyrrolidin-1-ylethyl-(2,2,2-trifluoroacetyl)amino]-5-[4-(2,2,2-trifluoroacetyl)piperazin-1-yl]benzoyl fluoride Chemical compound CC1=C(N(CCN2CCCC2)C(=O)C(F)(F)F)C=C(C(F)=O)C=C1N1CCN(C(=O)C(F)(F)F)CC1 FUQMYXHATNHEBU-UHFFFAOYSA-N 0.000 description 2
• GEBSWXYSAYUCIK-UHFFFAOYSA-N 5-(3,3-dimethylbutyl)-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(CCC(C)(C)C)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 GEBSWXYSAYUCIK-UHFFFAOYSA-N 0.000 description 2
• ICDORFVGVBPTPQ-UHFFFAOYSA-N 5-(3,5-dibromo-4-methylphenyl)-3-phenyl-1,2,4-oxadiazole Chemical compound C1=C(Br)C(C)=C(Br)C=C1C1=NC(C=2C=CC=CC=2)=NO1 ICDORFVGVBPTPQ-UHFFFAOYSA-N 0.000 description 2
• HQLVDQVRDDXAPF-UHFFFAOYSA-N 5-chloro-3-iodo-2-methylaniline Chemical compound CC1=C(N)C=C(Cl)C=C1I HQLVDQVRDDXAPF-UHFFFAOYSA-N 0.000 description 2
• OCEQBYVMMNGTIV-UHFFFAOYSA-N 6-methyl-1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound O=C1N=C(C)N=C2NNC=C21 OCEQBYVMMNGTIV-UHFFFAOYSA-N 0.000 description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
• 208000003200 Adenoma Diseases 0.000 description 2
• 206010001233 Adenoma benign Diseases 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
• 201000003076 Angiosarcoma Diseases 0.000 description 2
• 239000004475 Arginine Substances 0.000 description 2
• YWSPAMZYNRZEPH-UHFFFAOYSA-N CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)Cl)CCC=O Chemical compound CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)Cl)CCC=O YWSPAMZYNRZEPH-UHFFFAOYSA-N 0.000 description 2
• HMKHIMBBYPWFNR-UHFFFAOYSA-N CC1=CC(=C(C=C1OC(=O)N2CCNCC2)Cl)O Chemical compound CC1=CC(=C(C=C1OC(=O)N2CCNCC2)Cl)O HMKHIMBBYPWFNR-UHFFFAOYSA-N 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 206010007275 Carcinoid tumour Diseases 0.000 description 2
• 208000024172 Cardiovascular disease Diseases 0.000 description 2
• 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 2
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
• 102000009024 Epidermal Growth Factor Human genes 0.000 description 2
• 201000008808 Fibrosarcoma Diseases 0.000 description 2
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• 239000004471 Glycine Substances 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 208000001258 Hemangiosarcoma Diseases 0.000 description 2
• 206010061218 Inflammation Diseases 0.000 description 2
• 206010022489 Insulin Resistance Diseases 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
• XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
• QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 2
• 208000018142 Leiomyosarcoma Diseases 0.000 description 2
• 206010024612 Lipoma Diseases 0.000 description 2
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
• 239000004472 Lysine Substances 0.000 description 2
• 208000034578 Multiple myelomas Diseases 0.000 description 2
• 201000004404 Neurofibroma Diseases 0.000 description 2
• 208000008589 Obesity Diseases 0.000 description 2
• 235000019502 Orange oil Nutrition 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
• 206010035226 Plasma cell myeloma Diseases 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• OXNXUKTUQPCUSV-UHFFFAOYSA-N S-(3,5-dibromo-4-methylphenyl) N,N-dimethylcarbamothioate Chemical compound CN(C)C(=O)SC1=CC(Br)=C(C)C(Br)=C1 OXNXUKTUQPCUSV-UHFFFAOYSA-N 0.000 description 2
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• 235000002597 Solanum melongena Nutrition 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 101800004564 Transforming growth factor alpha Proteins 0.000 description 2
• 102400001320 Transforming growth factor alpha Human genes 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 125000004442 acylamino group Chemical group 0.000 description 2
• 239000008272 agar Substances 0.000 description 2
• 235000010419 agar Nutrition 0.000 description 2
• 235000004279 alanine Nutrition 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 125000004103 aminoalkyl group Chemical group 0.000 description 2
• 235000011114 ammonium hydroxide Nutrition 0.000 description 2
• 239000003242 anti bacterial agent Substances 0.000 description 2
• 238000003782 apoptosis assay Methods 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 125000005140 aralkylsulfonyl group Chemical group 0.000 description 2
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
• 125000003435 aroyl group Chemical group 0.000 description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
• 125000005116 aryl carbamoyl group Chemical group 0.000 description 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
• 125000000732 arylene group Chemical group 0.000 description 2
• 125000004104 aryloxy group Chemical group 0.000 description 2
• 230000001580 bacterial effect Effects 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• WZORUWZCRWIYSR-UHFFFAOYSA-N benzyl 3,5-dibromo-4-methylbenzoate Chemical compound C1=C(Br)C(C)=C(Br)C=C1C(=O)OCC1=CC=CC=C1 WZORUWZCRWIYSR-UHFFFAOYSA-N 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 230000000975 bioactive effect Effects 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 210000000988 bone and bone Anatomy 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 229910052792 caesium Inorganic materials 0.000 description 2
• TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
• 229960001948 caffeine Drugs 0.000 description 2
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 238000004422 calculation algorithm Methods 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
• 125000005518 carboxamido group Chemical group 0.000 description 2
• 208000002458 carcinoid tumor Diseases 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 230000004709 cell invasion Effects 0.000 description 2
• 230000012292 cell migration Effects 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
• 229960001231 choline Drugs 0.000 description 2
• GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 2
• 230000000295 complement effect Effects 0.000 description 2
• 238000007796 conventional method Methods 0.000 description 2
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
• QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
• 239000013058 crude material Substances 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• 235000018417 cysteine Nutrition 0.000 description 2
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
• 235000014113 dietary fatty acids Nutrition 0.000 description 2
• 230000004069 differentiation Effects 0.000 description 2
• 229960005156 digoxin Drugs 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 239000006185 dispersion Substances 0.000 description 2
• CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 2
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 230000032050 esterification Effects 0.000 description 2
• 238000005886 esterification reaction Methods 0.000 description 2
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
• 229930195729 fatty acid Natural products 0.000 description 2
• 239000000194 fatty acid Substances 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 235000019253 formic acid Nutrition 0.000 description 2
• 125000000524 functional group Chemical group 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 229940080856 gleevec Drugs 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 125000005549 heteroarylene group Chemical group 0.000 description 2
• 125000005553 heteroaryloxy group Chemical group 0.000 description 2
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
• 150000004678 hydrides Chemical class 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 230000006872 improvement Effects 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
• 230000004054 inflammatory process Effects 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
• 230000003993 interaction Effects 0.000 description 2
• 230000003834 intracellular effect Effects 0.000 description 2
• 230000009545 invasion Effects 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
• 201000010260 leiomyoma Diseases 0.000 description 2
• 239000008297 liquid dosage form Substances 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• 210000004185 liver Anatomy 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• 235000018977 lysine Nutrition 0.000 description 2
• 208000002780 macular degeneration Diseases 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
• 230000001404 mediated effect Effects 0.000 description 2
• 201000001441 melanoma Diseases 0.000 description 2
• 230000002503 metabolic effect Effects 0.000 description 2
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
• 229930014626 natural product Natural products 0.000 description 2
• 208000015122 neurodegenerative disease Diseases 0.000 description 2
• ZPSVEMAMMZJGAE-UHFFFAOYSA-N o-(3,5-dibromo-4-methylphenyl) n,n-dimethylcarbamothioate Chemical compound CN(C)C(=S)OC1=CC(Br)=C(C)C(Br)=C1 ZPSVEMAMMZJGAE-UHFFFAOYSA-N 0.000 description 2
• 235000020824 obesity Nutrition 0.000 description 2
• 235000008390 olive oil Nutrition 0.000 description 2
• 239000004006 olive oil Substances 0.000 description 2
• 230000000771 oncological effect Effects 0.000 description 2
• 239000010502 orange oil Substances 0.000 description 2
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• 230000001575 pathological effect Effects 0.000 description 2
• COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• 239000011574 phosphorus Chemical group 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 2
• 150000004885 piperazines Chemical class 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 230000005522 programmed cell death Effects 0.000 description 2
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
• 125000005551 pyridylene group Chemical group 0.000 description 2
• 230000002285 radioactive effect Effects 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 238000006722 reduction reaction Methods 0.000 description 2
• 238000011160 research Methods 0.000 description 2
• 201000009410 rhabdomyosarcoma Diseases 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 238000007423 screening assay Methods 0.000 description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 230000019491 signal transduction Effects 0.000 description 2
• 229940126586 small molecule drug Drugs 0.000 description 2
• 239000012453 solvate Substances 0.000 description 2
• 230000009870 specific binding Effects 0.000 description 2
• 239000007921 spray Substances 0.000 description 2
• 210000000130 stem cell Anatomy 0.000 description 2
• 239000000758 substrate Substances 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 230000002195 synergetic effect Effects 0.000 description 2
• AJDDAQMHYYXFRS-UHFFFAOYSA-N tert-butyl 4-(3-chloro-4-hydroxyphenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(O)C(Cl)=C1 AJDDAQMHYYXFRS-UHFFFAOYSA-N 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 238000013519 translation Methods 0.000 description 2
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
• 238000001665 trituration Methods 0.000 description 2
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
• 210000003932 urinary bladder Anatomy 0.000 description 2
• 210000001215 vagina Anatomy 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• GCJYUUCHJZQFLE-JQWIXIFHSA-N (2s)-2-[[2-[[(2s)-2-aminopropanoyl]amino]acetyl]amino]-n-[2-[2-(1h-imidazol-5-yl)ethylamino]acetyl]pentanediamide Chemical compound C[C@H](N)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)NC(=O)CNCCC1=CN=CN1 GCJYUUCHJZQFLE-JQWIXIFHSA-N 0.000 description 1
• YYXFJSDMOVHLMJ-UHFFFAOYSA-N (4-hydroxyphenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(O)C=C1 YYXFJSDMOVHLMJ-UHFFFAOYSA-N 0.000 description 1
• 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• PHWHUBAFWLAZGF-FXRZFVDSSA-N (e)-3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-enoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C3=C(\C=C\C(O)=O)NN=C3N=CN=2)CC1 PHWHUBAFWLAZGF-FXRZFVDSSA-N 0.000 description 1
• ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
• UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• XLOVPKCQAPHUKK-UHFFFAOYSA-N 1,2,3,4,4a,5,8,8a-octahydronaphthalene Chemical compound C1C=CCC2CCCCC21 XLOVPKCQAPHUKK-UHFFFAOYSA-N 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• ZROTYBDROASODD-UHFFFAOYSA-N 1,3-dibromo-5-ethylsulfanyl-2-methylbenzene Chemical compound CCSC1=CC(Br)=C(C)C(Br)=C1 ZROTYBDROASODD-UHFFFAOYSA-N 0.000 description 1
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
• WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 1
• CZZKIHOJCVOFHG-UHFFFAOYSA-N 1-(3-bromo-2-chloro-5-fluorophenyl)piperazine Chemical compound FC1=CC(Br)=C(Cl)C(N2CCNCC2)=C1 CZZKIHOJCVOFHG-UHFFFAOYSA-N 0.000 description 1
• RLTQWHLFGHJVFI-UHFFFAOYSA-N 1-(3-chloro-5-methoxyphenyl)piperazine Chemical compound COC1=CC(Cl)=CC(N2CCNCC2)=C1 RLTQWHLFGHJVFI-UHFFFAOYSA-N 0.000 description 1
• FUSRAMJWPKVNRA-UHFFFAOYSA-N 1-(3-chlorophenyl)-1,4-diazepane Chemical compound ClC1=CC=CC(N2CCNCCC2)=C1 FUSRAMJWPKVNRA-UHFFFAOYSA-N 0.000 description 1
• ZXDSDMHARDHNNZ-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-n-methylpiperazine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12C(CC)=NNC2=NC=NC=1N(CC1C(=O)NC)CCN1C1=CC=CC(Cl)=C1 ZXDSDMHARDHNNZ-UHFFFAOYSA-N 0.000 description 1
• OHIRPXMQOZVSBD-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-(1-methylpiperidin-4-yl)piperazine-2-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1N(C=2C=C(Cl)C=CC=2)CCNC1 OHIRPXMQOZVSBD-UHFFFAOYSA-N 0.000 description 1
• BSMMCZCMFLVTSV-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-[2-(dimethylamino)ethyl]piperazine-2-carboxamide Chemical compound CN(C)CCNC(=O)C1CNCCN1C1=CC=CC(Cl)=C1 BSMMCZCMFLVTSV-UHFFFAOYSA-N 0.000 description 1
• HLDYTCJMGQUHOX-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-methylpiperazine-2-carboxamide Chemical compound CNC(=O)C1CNCCN1C1=CC=CC(Cl)=C1 HLDYTCJMGQUHOX-UHFFFAOYSA-N 0.000 description 1
• RDTAAIKRENMWAE-UHFFFAOYSA-N 1-(5-chloro-3-methoxy-2-methylphenyl)piperazine Chemical compound COC1=CC(Cl)=CC(N2CCNCC2)=C1C RDTAAIKRENMWAE-UHFFFAOYSA-N 0.000 description 1
• UTJQWTYCZMVNGD-UHFFFAOYSA-N 1-(5-chloro-4-methoxy-2-methylphenyl)piperazine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C(OC)=CC(C)=C1N1CCNCC1 UTJQWTYCZMVNGD-UHFFFAOYSA-N 0.000 description 1
• VLZRARREIQDNHX-UHFFFAOYSA-N 1-(oxan-2-yl)pyrazolo[3,4-d]pyrimidine Chemical compound O1CCCCC1N1C2=NC=NC=C2C=N1 VLZRARREIQDNHX-UHFFFAOYSA-N 0.000 description 1
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
• FNSRDZSZLGZKCM-UHFFFAOYSA-N 1-[2-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)ethyl]-4-ethylpiperazine Chemical compound C1CN(CC)CCN1CCOC1=CC(Cl)=CC(N2CCNCC2)=C1C FNSRDZSZLGZKCM-UHFFFAOYSA-N 0.000 description 1
• LGNQJWUDGZGYQN-UHFFFAOYSA-N 1-[2-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)ethyl]-4-methylpiperazine;hydrochloride Chemical compound Cl.C1CN(C)CCN1CCOC1=CC(Cl)=CC(N2CCNCC2)=C1C LGNQJWUDGZGYQN-UHFFFAOYSA-N 0.000 description 1
• MEFLKSADQOHPFZ-UHFFFAOYSA-N 1-[3-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)propyl]-4-ethylpiperazine Chemical compound C1CN(CC)CCN1CCCOC1=CC(Cl)=CC(N2CCNCC2)=C1C MEFLKSADQOHPFZ-UHFFFAOYSA-N 0.000 description 1
• SVQBXJZDAGXPOT-UHFFFAOYSA-N 1-[3-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC1=CC(Cl)=CC(N2CCNCC2)=C1C SVQBXJZDAGXPOT-UHFFFAOYSA-N 0.000 description 1
• QNIHNXZWIZTTCG-UHFFFAOYSA-N 1-[3-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)propyl]-4-methylpiperazine;hydrochloride Chemical compound Cl.C1CN(C)CCN1CCCC1=CC(Cl)=CC(N2CCNCC2)=C1C QNIHNXZWIZTTCG-UHFFFAOYSA-N 0.000 description 1
• KAYXZTXFDYAUHP-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]-4,4,4-trifluorobutan-1-one;hydrochloride Chemical compound Cl.C1=C(C(=O)CCC(F)(F)F)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 KAYXZTXFDYAUHP-UHFFFAOYSA-N 0.000 description 1
• OYECUJHTGCCYCS-UHFFFAOYSA-N 1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]ethanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)C)=CC=1NCCN1CCCC1 OYECUJHTGCCYCS-UHFFFAOYSA-N 0.000 description 1
• ACSPARFTZCIAPK-UHFFFAOYSA-N 1-[4-methyl-3-piperazin-1-yl-5-(2-pyrrolidin-1-ylethylamino)phenyl]pentan-1-one;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(C(=O)CCCC)=CC=1NCCN1CCCC1 ACSPARFTZCIAPK-UHFFFAOYSA-N 0.000 description 1
• ZWAHUEXJZPIPFV-UHFFFAOYSA-N 1-[4-methyl-3-piperazin-1-yl-5-(2-pyrrolidin-1-ylethylamino)phenyl]propan-1-one;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(C(=O)CC)=CC=1NCCN1CCCC1 ZWAHUEXJZPIPFV-UHFFFAOYSA-N 0.000 description 1
• FHCHAWMBEYOCHR-UHFFFAOYSA-N 1-[5-chloro-2-methyl-3-(2-piperidin-1-ylethoxy)phenyl]piperazine Chemical compound C1=C(Cl)C=C(N2CCNCC2)C(C)=C1OCCN1CCCCC1 FHCHAWMBEYOCHR-UHFFFAOYSA-N 0.000 description 1
• MBTCMEMTPCBHQG-UHFFFAOYSA-N 1-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazine Chemical compound C1=C(Cl)C=C(N2CCNCC2)C(C)=C1OCCN1CCCC1 MBTCMEMTPCBHQG-UHFFFAOYSA-N 0.000 description 1
• QZGJRDFHUSXJMZ-UHFFFAOYSA-N 1-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropoxy)phenyl]piperazine Chemical compound C1=C(Cl)C=C(N2CCNCC2)C(C)=C1OCCCN1CCCCC1 QZGJRDFHUSXJMZ-UHFFFAOYSA-N 0.000 description 1
• HMKHZGQQZUYGOX-UHFFFAOYSA-N 1-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropoxy)phenyl]piperazine Chemical compound C1=C(Cl)C=C(N2CCNCC2)C(C)=C1OCCCN1CCCC1 HMKHZGQQZUYGOX-UHFFFAOYSA-N 0.000 description 1
• LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
• JRGGUPZKKTVKOV-UHFFFAOYSA-N 1-bromo-3-chlorobenzene Chemical compound ClC1=CC=CC(Br)=C1 JRGGUPZKKTVKOV-UHFFFAOYSA-N 0.000 description 1
• DKVJRZYMFJNVOD-UHFFFAOYSA-N 1-ethyl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CNC(=O)C2=C1N(CC)N=C2 DKVJRZYMFJNVOD-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 1
• MKTPOHXUXWUJNO-UHFFFAOYSA-N 1-tert-butyl-3-(trifluoromethyl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CN=C2N(C(C)(C)C)N=C(C(F)(F)F)C2=C1O MKTPOHXUXWUJNO-UHFFFAOYSA-N 0.000 description 1
• WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 1
• UZURTQHPMXADGG-UHFFFAOYSA-N 2,3,3a,4,7,7a-hexahydro-1h-indene Chemical compound C1C=CCC2CCCC21 UZURTQHPMXADGG-UHFFFAOYSA-N 0.000 description 1
• PHXGAJLBHUUAKB-UHFFFAOYSA-N 2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound O1CCC2OCCC21 PHXGAJLBHUUAKB-UHFFFAOYSA-N 0.000 description 1
• OZJZCCMIOZPPIT-UHFFFAOYSA-N 2-(2-methoxyethoxy)acetyl chloride Chemical compound COCCOCC(Cl)=O OZJZCCMIOZPPIT-UHFFFAOYSA-N 0.000 description 1
• GPMRZLROSLBOST-UHFFFAOYSA-N 2-(3-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptane;hydrochloride Chemical compound Cl.ClC1=CC=CC(N2C3CC(NC3)C2)=C1 GPMRZLROSLBOST-UHFFFAOYSA-N 0.000 description 1
• WITNOYWFEMOXJQ-UHFFFAOYSA-N 2-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC(Cl)=CC(N2CCNCC2)=C1C WITNOYWFEMOXJQ-UHFFFAOYSA-N 0.000 description 1
• NKCYQDGFDPORHX-UHFFFAOYSA-N 2-[1-hydroxy-2-(2-methoxyethoxy)ethylidene]propanedinitrile Chemical compound COCCOCC(O)=C(C#N)C#N NKCYQDGFDPORHX-UHFFFAOYSA-N 0.000 description 1
• DPBXZBAFJZFNEU-UHFFFAOYSA-N 2-[2-chloro-4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-methylphenoxy]-n,n-dimethylethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C1=CC(Cl)=C(OCCN(C)C)C=C1C DPBXZBAFJZFNEU-UHFFFAOYSA-N 0.000 description 1
• KXFPRYJZNFUBAI-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenoxy]-n,n-diethylethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCN(CC)CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C3=C(NN=C3N=CN=2)C(F)(F)F)=C1C KXFPRYJZNFUBAI-UHFFFAOYSA-N 0.000 description 1
• ROLRVFVPEUIBKU-UHFFFAOYSA-N 2-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methoxyphenoxy]-n,n-dimethylethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C1=CC(Cl)=CC(OCCN(C)C)=C1OC ROLRVFVPEUIBKU-UHFFFAOYSA-N 0.000 description 1
• HRFVAWXEZPKKKI-UHFFFAOYSA-N 2-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]-n,n-diethylethanamine;hydrochloride Chemical compound Cl.CCN(CC)CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C HRFVAWXEZPKKKI-UHFFFAOYSA-N 0.000 description 1
• ZSLSTFJDDMMQET-UHFFFAOYSA-N 2-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(OCCN(C)C)=C1C ZSLSTFJDDMMQET-UHFFFAOYSA-N 0.000 description 1
• MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
• OHQCOWQNKVFADT-UHFFFAOYSA-N 2-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-fluoro-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1Cl)=CC(F)=CC=1NCCN1CCCC1 OHQCOWQNKVFADT-UHFFFAOYSA-N 0.000 description 1
• LMKQEPXWBDAMIA-UHFFFAOYSA-N 2-chloro-5-fluoro-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound ClC=1C(N2CCNCC2)=CC(F)=CC=1NCCN1CCCC1 LMKQEPXWBDAMIA-UHFFFAOYSA-N 0.000 description 1
• BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
• 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
• ZMFGJDMBUKOPBV-UHFFFAOYSA-N 2-methyl-3-piperazin-1-yl-5-propan-2-yloxy-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(OC(C)C)=CC=1NCCN1CCCC1 ZMFGJDMBUKOPBV-UHFFFAOYSA-N 0.000 description 1
• BLPUNWQGIQUFNC-UHFFFAOYSA-N 2-methyl-3-piperazin-1-yl-5-propoxy-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(OCCC)=CC=1NCCN1CCCC1 BLPUNWQGIQUFNC-UHFFFAOYSA-N 0.000 description 1
• DFJHHZMJCJHNHH-UHFFFAOYSA-N 2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)-5-(2-trimethylsilylethyl)aniline Chemical compound C1=C(CC[Si](C)(C)C)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 DFJHHZMJCJHNHH-UHFFFAOYSA-N 0.000 description 1
• OVLBJMSFGAKMSF-UHFFFAOYSA-N 2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)-5-(3,3,3-trifluoropropoxy)aniline;hydrochloride Chemical compound Cl.C1=C(OCCC(F)(F)F)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 OVLBJMSFGAKMSF-UHFFFAOYSA-N 0.000 description 1
• DKNNPBSTUKJQAG-UHFFFAOYSA-N 2-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl]piperazine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCNC(C)(C(O)=O)C1 DKNNPBSTUKJQAG-UHFFFAOYSA-N 0.000 description 1
• ZUAWCLGUHKNAIA-UHFFFAOYSA-N 2-methyl-5-(2-methylpropoxy)-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(OCC(C)C)=CC=1NCCN1CCCC1 ZUAWCLGUHKNAIA-UHFFFAOYSA-N 0.000 description 1
• ZYKQWDMKJZVYIU-UHFFFAOYSA-N 2-methyl-5-(2-phenylethyl)-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(CCC=2C=CC=CC=2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 ZYKQWDMKJZVYIU-UHFFFAOYSA-N 0.000 description 1
• OVJNRSLJOAJKEE-UHFFFAOYSA-N 2-methyl-5-(2-phenylethynyl)-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(C#CC=2C=CC=CC=2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 OVJNRSLJOAJKEE-UHFFFAOYSA-N 0.000 description 1
• JZGASZBCHPZJHD-UHFFFAOYSA-N 2-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC1=NOC(C=2C=C(C(C)=C(NCCN3CCCC3)C=2)N2CCNCC2)=N1 JZGASZBCHPZJHD-UHFFFAOYSA-N 0.000 description 1
• BDWVGFUBSJWIHS-UHFFFAOYSA-N 2-methyl-5-(3-methylbutoxy)-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(OCCC(C)C)=CC=1NCCN1CCCC1 BDWVGFUBSJWIHS-UHFFFAOYSA-N 0.000 description 1
• CVVNTEJYPAXKCF-UHFFFAOYSA-N 2-methyl-5-(3-phenyl-1,2,4-oxadiazol-5-yl)-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(C=2ON=C(N=2)C=2C=CC=CC=2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 CVVNTEJYPAXKCF-UHFFFAOYSA-N 0.000 description 1
• XAFANKYUWHODAK-UHFFFAOYSA-N 2-methyl-5-(oxolan-2-ylmethoxy)-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(OCC2OCCC2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 XAFANKYUWHODAK-UHFFFAOYSA-N 0.000 description 1
• KKTJBKMAHMUXSN-UHFFFAOYSA-N 2-methyl-5-methylsulfonyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(S(C)(=O)=O)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 KKTJBKMAHMUXSN-UHFFFAOYSA-N 0.000 description 1
• SGNVAYIPRSEKFH-UHFFFAOYSA-N 2-methyl-5-phenylmethoxy-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC=2C=CC=CC=2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 SGNVAYIPRSEKFH-UHFFFAOYSA-N 0.000 description 1
• BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
• 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• CGNJNFZTDWGNSF-UHFFFAOYSA-N 2h-pyrimidin-1-amine Chemical compound NN1CN=CC=C1 CGNJNFZTDWGNSF-UHFFFAOYSA-N 0.000 description 1
• PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 description 1
• HUWLDUMHTSHONZ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C3=C(C=4C=C5OCOC5=CC=4)NN=C3N=CN=2)CC1 HUWLDUMHTSHONZ-UHFFFAOYSA-N 0.000 description 1
• GAUUCHYDLVWVTQ-UHFFFAOYSA-N 3-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCOC1=CC(Cl)=CC(N2CCNCC2)=C1C GAUUCHYDLVWVTQ-UHFFFAOYSA-N 0.000 description 1
• RGGPCUABEGXGQB-UHFFFAOYSA-N 3-(azetidin-3-ylidenemethyl)-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C3=C(C=C4CNC4)NN=C3N=CN=2)CC1 RGGPCUABEGXGQB-UHFFFAOYSA-N 0.000 description 1
• KKGUMGWNFARLSL-UHFFFAOYSA-N 3-(bromomethyl)pentane Chemical compound CCC(CC)CBr KKGUMGWNFARLSL-UHFFFAOYSA-N 0.000 description 1
• RZAHIWXBDWFJID-UHFFFAOYSA-N 3-[2-chloro-4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-methylphenoxy]-n,n-dimethylpropan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C1=CC(Cl)=C(OCCCN(C)C)C=C1C RZAHIWXBDWFJID-UHFFFAOYSA-N 0.000 description 1
• UXCHHUGMTOICBK-UHFFFAOYSA-N 3-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenoxy]-n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C UXCHHUGMTOICBK-UHFFFAOYSA-N 0.000 description 1
• REMJBFLHUDUAAB-UHFFFAOYSA-N 3-[4-(3-bromo-2H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-N-(2-pyrrolidin-1-ylethyl)-5-(2-trimethylsilylethyl)aniline 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(CC[Si](C)(C)C)C=C(N2CCN(CC2)C=2C3=C(Br)NN=C3N=CN=2)C(C)=C1NCCN1CCCC1 REMJBFLHUDUAAB-UHFFFAOYSA-N 0.000 description 1
• DXRQWKMABDCEPQ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-chloro-5-fluoro-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.ClC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(F)=CC=1NCCN1CCCC1 DXRQWKMABDCEPQ-UHFFFAOYSA-N 0.000 description 1
• HNXHTZJWDDEAPU-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(3-methylbutoxy)-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCCC(C)C)=CC=1NCCN1CCCC1 HNXHTZJWDDEAPU-UHFFFAOYSA-N 0.000 description 1
• PGVQMDPVMHGBQK-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(3-phenyl-1,2,4-oxadiazol-5-yl)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(C=2ON=C(N=2)C=2C=CC=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 PGVQMDPVMHGBQK-UHFFFAOYSA-N 0.000 description 1
• WBOUCZBCMVVFCT-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-propan-2-yloxy-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OC(C)C)=CC=1NCCN1CCCC1 WBOUCZBCMVVFCT-UHFFFAOYSA-N 0.000 description 1
• OQKYBAPVQVRKNQ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2-methoxyethoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCCOC)=CC=1NCCN1CCCC1 OQKYBAPVQVRKNQ-UHFFFAOYSA-N 0.000 description 1
• SHPKPYILMUKFEL-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(cyclohexylmethoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(OCC2CCCCC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 SHPKPYILMUKFEL-UHFFFAOYSA-N 0.000 description 1
• IXVIFKUANGTJCC-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(cyclopropylmethoxy)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(OCC2CC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 IXVIFKUANGTJCC-UHFFFAOYSA-N 0.000 description 1
• OVASKJWVAVYOBN-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-ethoxy-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(OCC)=CC=1NCCN1CCCC1 OVASKJWVAVYOBN-UHFFFAOYSA-N 0.000 description 1
• OPOIVVNFQFPRCR-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-ethyl-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC=1C(N2CCN(CC2)C=2C3=C(Br)NN=C3N=CN=2)=CC(CC)=CC=1NCCN1CCCC1 OPOIVVNFQFPRCR-UHFFFAOYSA-N 0.000 description 1
• HMOJRYPCFXCCOD-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-ethynyl-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C#C)C=C(N2CCN(CC2)C=2C3=C(Br)NN=C3N=CN=2)C(C)=C1NCCN1CCCC1 HMOJRYPCFXCCOD-UHFFFAOYSA-N 0.000 description 1
• MMEGZVSPBZFNNO-UHFFFAOYSA-N 3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(2-methylpropoxy)-n-(2-pyrrolidin-1-ylethyl)aniline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C(C=1C)=CC(OCC(C)C)=CC=1NCCN1CCCC1 MMEGZVSPBZFNNO-UHFFFAOYSA-N 0.000 description 1
• VAVUERYYXDBTAO-UHFFFAOYSA-N 3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-phenylmethoxy-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C(=C(NCCN1CCCC1)C=1)C)=CC=1OCC1=CC=CC=C1 VAVUERYYXDBTAO-UHFFFAOYSA-N 0.000 description 1
• RUQUXSJOPZLPKC-UHFFFAOYSA-N 3-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]-5-(2-pyrrolidin-1-ylethylamino)benzoic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC(NCCN2CCCC2)=CC(C(O)=O)=C1 RUQUXSJOPZLPKC-UHFFFAOYSA-N 0.000 description 1
• YMLMLJNFVOKXBP-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-1-(oxan-2-yl)pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-yn-1-ol Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C#CCO)=NN(C=3N=CN=2)C2OCCCC2)CC1 YMLMLJNFVOKXBP-UHFFFAOYSA-N 0.000 description 1
• WMIMZCRRUJOOLF-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]-n,n-diethylpropan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CCCN(CC)CC)NN=C2N=CN=C1N(CC1)CCN1C1=CC(Cl)=CC=C1C WMIMZCRRUJOOLF-UHFFFAOYSA-N 0.000 description 1
• JJOUSWZGGIWTQV-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]aniline;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C(N)C=CC=4)=NNC=3N=CN=2)CC1 JJOUSWZGGIWTQV-UHFFFAOYSA-N 0.000 description 1
• KUXRYMPTTGNOEI-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C(C=CC=4)C(O)=O)=NNC=3N=CN=2)CC1 KUXRYMPTTGNOEI-UHFFFAOYSA-N 0.000 description 1
• HNWRGXBWEZEZMH-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]phenol;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C(O)C=CC=4)=NNC=3N=CN=2)CC1 HNWRGXBWEZEZMH-UHFFFAOYSA-N 0.000 description 1
• HKEJFUHECWPQKD-UHFFFAOYSA-N 3-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenoxy]-n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C HKEJFUHECWPQKD-UHFFFAOYSA-N 0.000 description 1
• FJHDRIZZFXDPIZ-UHFFFAOYSA-N 3-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenyl]-n,n-diethylpropan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCN(CC)CCCC1=CC(Cl)=CC(N2CCN(CC2)C=2C3=C(NN=C3N=CN=2)C(F)(F)F)=C1C FJHDRIZZFXDPIZ-UHFFFAOYSA-N 0.000 description 1
• QUEZQNSZWRZLCB-UHFFFAOYSA-N 3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]-n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C QUEZQNSZWRZLCB-UHFFFAOYSA-N 0.000 description 1
• LVAYWLZOLMFGOM-UHFFFAOYSA-N 3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CCCC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C LVAYWLZOLMFGOM-UHFFFAOYSA-N 0.000 description 1
• RAXMUHNCMQAQSH-UHFFFAOYSA-N 3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n,n-dimethylprop-2-yn-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C1=CC(Cl)=CC(C#CCN(C)C)=C1C RAXMUHNCMQAQSH-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• YSEOWINAKUGZSZ-UHFFFAOYSA-N 3-bromo-4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-1-(oxan-2-yl)pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(Br)=NN(C=3N=CN=2)C2OCCCC2)CC1 YSEOWINAKUGZSZ-UHFFFAOYSA-N 0.000 description 1
• CSXVQPBQDYAKDK-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-[(1-methylpiperidin-4-yl)methoxy]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(C)CCC1COC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C CSXVQPBQDYAKDK-UHFFFAOYSA-N 0.000 description 1
• HIWHRYZBEQXNCL-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-[2-(1-methylpiperidin-4-yl)ethoxy]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(C)CCC1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C HIWHRYZBEQXNCL-UHFFFAOYSA-N 0.000 description 1
• TYKANOSYGXUPIU-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(C)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C TYKANOSYGXUPIU-UHFFFAOYSA-N 0.000 description 1
• LTPIFSNYAGAFQP-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(C)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C LTPIFSNYAGAFQP-UHFFFAOYSA-N 0.000 description 1
• FGJFTFJHSPZCLV-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-3-[2-(4-ethylpiperazin-1-yl)ethoxy]-2-methylphenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(CC)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C FGJFTFJHSPZCLV-UHFFFAOYSA-N 0.000 description 1
• AFRSPPDYILFHIW-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-3-[3-(4-ethylpiperazin-1-yl)propoxy]-2-methylphenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(CC)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C AFRSPPDYILFHIW-UHFFFAOYSA-N 0.000 description 1
• DVECOUBXTSYIFO-UHFFFAOYSA-N 3-bromo-5-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-n-phenylbenzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C(=C(Br)C=1)C)=CC=1C(=O)NC1=CC=CC=C1 DVECOUBXTSYIFO-UHFFFAOYSA-N 0.000 description 1
• KCPLJPHQKPGNHT-UHFFFAOYSA-N 3-phenyl-1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=2C(O)=NC=NC=2NN=C1C1=CC=CC=C1 KCPLJPHQKPGNHT-UHFFFAOYSA-N 0.000 description 1
• ALUSQWKDVGPZPB-UHFFFAOYSA-N 4,4,4-trifluoro-1-[4-methyl-3-piperazin-1-yl-5-(2-pyrrolidin-1-ylethylamino)phenyl]butan-1-one;hydrochloride Chemical compound Cl.C1=C(C(=O)CCC(F)(F)F)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 ALUSQWKDVGPZPB-UHFFFAOYSA-N 0.000 description 1
• NBJHDLKSWUDGJG-UHFFFAOYSA-N 4-(2-chloroethyl)morpholin-4-ium;chloride Chemical compound Cl.ClCCN1CCOCC1 NBJHDLKSWUDGJG-UHFFFAOYSA-N 0.000 description 1
• IYWKLFKURTWJFJ-UHFFFAOYSA-N 4-(3-chlorophenyl)-n-methylpiperazine-2-carboxamide Chemical compound C1CNC(C(=O)NC)CN1C1=CC=CC(Cl)=C1 IYWKLFKURTWJFJ-UHFFFAOYSA-N 0.000 description 1
• GMUPYKQZMBLHEB-UHFFFAOYSA-N 4-(4-phenylpiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CCC1C1=CC=CC=C1 GMUPYKQZMBLHEB-UHFFFAOYSA-N 0.000 description 1
• RBIGGFXRTIGRON-UHFFFAOYSA-N 4-[2-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)ethyl]morpholine Chemical compound C1=C(Cl)C=C(N2CCNCC2)C(C)=C1OCCN1CCOCC1 RBIGGFXRTIGRON-UHFFFAOYSA-N 0.000 description 1
• JTMHRIMHYBXMQR-UHFFFAOYSA-N 4-[2-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenoxy]ethyl]morpholine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C(N2CCN(CC2)C=2C3=C(NN=C3N=CN=2)C(F)(F)F)C(C)=C1OCCN1CCOCC1 JTMHRIMHYBXMQR-UHFFFAOYSA-N 0.000 description 1
• CILVJYXWYQSTCB-UHFFFAOYSA-N 4-[2-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]ethyl]morpholine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCOCC1 CILVJYXWYQSTCB-UHFFFAOYSA-N 0.000 description 1
• VYHIONPWWCKWOF-UHFFFAOYSA-N 4-[3-(5-chloro-2-methyl-3-piperazin-1-ylphenoxy)propyl]morpholine Chemical compound C1=C(Cl)C=C(N2CCNCC2)C(C)=C1OCCCN1CCOCC1 VYHIONPWWCKWOF-UHFFFAOYSA-N 0.000 description 1
• CCVDVJXNLXZBAN-UHFFFAOYSA-N 4-[3-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenoxy]propyl]morpholine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C(N2CCN(CC2)C=2C3=C(NN=C3N=CN=2)C(F)(F)F)C(C)=C1OCCCN1CCOCC1 CCVDVJXNLXZBAN-UHFFFAOYSA-N 0.000 description 1
• POEJPYMKOSSIGK-UHFFFAOYSA-N 4-[3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]propyl]morpholine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1CCCN1CCOCC1 POEJPYMKOSSIGK-UHFFFAOYSA-N 0.000 description 1
• GPCOCFSLOGRFHR-UHFFFAOYSA-N 4-[3-bromo-2-methyl-5-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl]piperazine-1-carboxylic acid Chemical compound CC1=C(Br)C=C(C=2ON=C(N=2)C=2C=CC=CC=2)C=C1N1CCN(C(O)=O)CC1 GPCOCFSLOGRFHR-UHFFFAOYSA-N 0.000 description 1
• YRKKQVKSWQLXBZ-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=CC=CC=C1N1CCN(C=2C=3C=CNC=3N=CN=2)CC1 YRKKQVKSWQLXBZ-UHFFFAOYSA-N 0.000 description 1
• IBXALBYOWBTGRR-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound FC1=CC=CC=C1N1CCN(C=2C=3C=CNC=3N=CN=2)CC1 IBXALBYOWBTGRR-UHFFFAOYSA-N 0.000 description 1
• PNKDJCFGTHLQCJ-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=CC=C1N1CCN(C=2C=3C=CNC=3N=CN=2)CC1 PNKDJCFGTHLQCJ-UHFFFAOYSA-N 0.000 description 1
• CTJVUQNXXFJPAN-UHFFFAOYSA-N 4-[4-(2-methylphenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC=C1N1CCN(C=2C=3C=CNC=3N=CN=2)CC1 CTJVUQNXXFJPAN-UHFFFAOYSA-N 0.000 description 1
• ZIYLOLUWFBWXIH-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)-1,4-diazepan-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCCN1C1=CC=CC(Cl)=C1 ZIYLOLUWFBWXIH-UHFFFAOYSA-N 0.000 description 1
• WUWSJZJZLJLZJJ-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=CC=CC(N2CCN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 WUWSJZJZLJLZJJ-UHFFFAOYSA-N 0.000 description 1
• YCDVPZJRYIIRMM-UHFFFAOYSA-N 4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6,7-dimethoxyquinazoline;hydrochloride Chemical compound Cl.COC1=C(OC)C=C2C(N3CCN(CC3)C=3N=CN=C4NN=C(C=34)CC)=NC=NC2=C1 YCDVPZJRYIIRMM-UHFFFAOYSA-N 0.000 description 1
• FWECWZKFGBIJMK-UHFFFAOYSA-N 4-[4-(3-methoxyphenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=CC(N2CCN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 FWECWZKFGBIJMK-UHFFFAOYSA-N 0.000 description 1
• BKUPEAMZZKHYFG-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(Cl)=CC=C1N1CCN(C=2C=3C=CNC=3N=CN=2)CC1 BKUPEAMZZKHYFG-UHFFFAOYSA-N 0.000 description 1
• MGAUNJWDDNBFEB-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(F)=CC=C1N1CCN(C=2C=3C=CNC=3N=CN=2)CC1 MGAUNJWDDNBFEB-UHFFFAOYSA-N 0.000 description 1
• AAICARCSHFYCBL-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=3C=CNC=3N=CN=2)CC1 AAICARCSHFYCBL-UHFFFAOYSA-N 0.000 description 1
• ACZXBVMTGYCNEN-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(2-methoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 ACZXBVMTGYCNEN-UHFFFAOYSA-N 0.000 description 1
• ALWXPUXBRVQMDL-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-chloropyridin-4-yl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C3=C(C=4C(=CN=CC=4)Cl)NN=C3N=CN=2)CC1 ALWXPUXBRVQMDL-UHFFFAOYSA-N 0.000 description 1
• ADJZJDJUQKXOMS-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-fluoropyridin-4-yl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C3=C(C=4C(=CN=CC=4)F)NN=C3N=CN=2)CC1 ADJZJDJUQKXOMS-UHFFFAOYSA-N 0.000 description 1
• OMCCPHMUSBKOEW-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-methoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C2=C3C(N4CCN(CC4)C=4C(=CC=C(Cl)C=4)C)=NC=NC3=NN2)=C1 OMCCPHMUSBKOEW-UHFFFAOYSA-N 0.000 description 1
• RDZNVJSIJFRQLN-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-methylbut-2-enyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C=12C(CC=C(C)C)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C RDZNVJSIJFRQLN-UHFFFAOYSA-N 0.000 description 1
• CFGPESOSYCRXJM-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-phenylmethoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=C(OCC=5C=CC=CC=5)C=CC=4)=NNC=3N=CN=2)CC1 CFGPESOSYCRXJM-UHFFFAOYSA-N 0.000 description 1
• ADBQQNVNDJBSPR-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-pyrrolidin-1-ylpropyl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C3=C(CCCN4CCCC4)NN=C3N=CN=2)CC1 ADBQQNVNDJBSPR-UHFFFAOYSA-N 0.000 description 1
• WUGZCLZJRNBWGH-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-fluorophenyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(F)=CC=4)=NNC=3N=CN=2)CC1 WUGZCLZJRNBWGH-UHFFFAOYSA-N 0.000 description 1
• MZFQSBSBOCXURY-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-methoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 MZFQSBSBOCXURY-UHFFFAOYSA-N 0.000 description 1
• PYAXKDBTDYPILG-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-methylphenyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 PYAXKDBTDYPILG-UHFFFAOYSA-N 0.000 description 1
• PSQXKUZZVBIEGS-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(4-phenoxyphenyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(OC=5C=CC=CC=5)=CC=4)=NNC=3N=CN=2)CC1 PSQXKUZZVBIEGS-UHFFFAOYSA-N 0.000 description 1
• LCTJNACRHLPHCC-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(piperidin-4-ylmethyl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C3=C(CC4CCNCC4)NN=C3N=CN=2)CC1 LCTJNACRHLPHCC-UHFFFAOYSA-N 0.000 description 1
• JPIRECAMUSZVHI-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-[4-(piperidin-4-ylmethoxy)phenyl]-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(OCC5CCNCC5)=CC=4)=NNC=3N=CN=2)CC1 JPIRECAMUSZVHI-UHFFFAOYSA-N 0.000 description 1
• LJTNPOMRKDRDDX-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-pyridin-4-yl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CN=CC=4)=NNC=3N=CN=2)CC1 LJTNPOMRKDRDDX-UHFFFAOYSA-N 0.000 description 1
• JAQCOIIUEBIFCE-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-thiophen-2-yl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4SC=CC=4)=NNC=3N=CN=2)CC1 JAQCOIIUEBIFCE-UHFFFAOYSA-N 0.000 description 1
• HRFDNZHBOSXNJX-UHFFFAOYSA-N 4-[4-[2-chloro-5-(trifluoromethyl)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C1=CC(C(F)(F)F)=CC=C1Cl HRFDNZHBOSXNJX-UHFFFAOYSA-N 0.000 description 1
• YISGVHBBSBDPLQ-UHFFFAOYSA-N 4-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 YISGVHBBSBDPLQ-UHFFFAOYSA-N 0.000 description 1
• ADNQTKKLFYIXOD-UHFFFAOYSA-N 4-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]benzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C=4C=CC(=CC=4)C#N)=NNC=3N=CN=2)CC1 ADNQTKKLFYIXOD-UHFFFAOYSA-N 0.000 description 1
• HQEDABRUWZCNLW-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-piperidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1OCCN1CCCCC1 HQEDABRUWZCNLW-UHFFFAOYSA-N 0.000 description 1
• VKQQVRILEOLGGH-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-piperidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCCC1 VKQQVRILEOLGGH-UHFFFAOYSA-N 0.000 description 1
• CFUYCXAVBBYTOY-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-(2-methylpropyl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC(C)C)NN=C2N=CN=C1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCC1 CFUYCXAVBBYTOY-UHFFFAOYSA-N 0.000 description 1
• VUYPARZAFPXXRA-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C(N2CCN(CC2)C=2C3=C(NN=C3N=CN=2)C(F)(F)F)C(C)=C1OCCN1CCCC1 VUYPARZAFPXXRA-UHFFFAOYSA-N 0.000 description 1
• BKVWBBPEOOUCSR-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCC1 BKVWBBPEOOUCSR-UHFFFAOYSA-N 0.000 description 1
• GUUIFYHFFRHFBZ-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-propan-2-yl-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(C(C)C)NN=C2N=CN=C1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCCC1 GUUIFYHFFRHFBZ-UHFFFAOYSA-N 0.000 description 1
• XGYIRABXHUEQMY-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C(N2CCN(CC2)C=2C3=C(NN=C3N=CN=2)C(F)(F)F)C(C)=C1OCCCN1CCCCC1 XGYIRABXHUEQMY-UHFFFAOYSA-N 0.000 description 1
• OIWSVSQGOROZBB-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropyl)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C(N2CCN(CC2)C=2C3=C(NN=C3N=CN=2)C(F)(F)F)C(C)=C1CCCN1CCCCC1 OIWSVSQGOROZBB-UHFFFAOYSA-N 0.000 description 1
• QEGYOIPCNDGRJA-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropyl)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1CCCN1CCCCC1 QEGYOIPCNDGRJA-UHFFFAOYSA-N 0.000 description 1
• FAGYIQZPQWAMIH-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C(N2CCN(CC2)C=2C3=C(NN=C3N=CN=2)C(F)(F)F)C(C)=C1OCCCN1CCCC1 FAGYIQZPQWAMIH-UHFFFAOYSA-N 0.000 description 1
• FWMXCFUMSBFAAI-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)C(C)=C1CCCN1CCCC1 FWMXCFUMSBFAAI-UHFFFAOYSA-N 0.000 description 1
• UMAHJFYRLZKLOT-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropyl)phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1CCCN1CCCC1 UMAHJFYRLZKLOT-UHFFFAOYSA-N 0.000 description 1
• HFXWHWGFDJBVQH-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[(1-methylpiperidin-4-yl)methoxy]phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(C)CCC1COC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C HFXWHWGFDJBVQH-UHFFFAOYSA-N 0.000 description 1
• MNSFYCKQACUVJB-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[(1-methylpiperidin-4-yl)methoxy]phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCC1CCN(C)CC1 MNSFYCKQACUVJB-UHFFFAOYSA-N 0.000 description 1
• JOIVONGZLVWEHI-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[2-(1-methylpiperidin-4-yl)ethoxy]phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCC1CCN(C)CC1 JOIVONGZLVWEHI-UHFFFAOYSA-N 0.000 description 1
• JYWUNYPUTQRCHE-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(C)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C JYWUNYPUTQRCHE-UHFFFAOYSA-N 0.000 description 1
• IPFGHGNLNCWHKN-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCN1CCN(C)CC1 IPFGHGNLNCWHKN-UHFFFAOYSA-N 0.000 description 1
• HBRFNDKRWBFTPH-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCCN1CCN(C)CC1 HBRFNDKRWBFTPH-UHFFFAOYSA-N 0.000 description 1
• UPZLGMPAYVCPFC-UHFFFAOYSA-N 4-[4-[5-chloro-3-[2-(4-ethylpiperazin-1-yl)ethoxy]-2-methylphenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(CC)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C UPZLGMPAYVCPFC-UHFFFAOYSA-N 0.000 description 1
• XKNJFTICVUXZNU-UHFFFAOYSA-N 4-[4-[5-chloro-3-[2-(4-ethylpiperazin-1-yl)ethoxy]-2-methylphenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(CC)CCN1CCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C XKNJFTICVUXZNU-UHFFFAOYSA-N 0.000 description 1
• APEXOLLBPUHHJU-UHFFFAOYSA-N 4-[4-[5-chloro-3-[3-(4-ethylpiperazin-1-yl)propoxy]-2-methylphenyl]piperazin-1-yl]-3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(CC)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C APEXOLLBPUHHJU-UHFFFAOYSA-N 0.000 description 1
• AWFYCBLBBLZBBT-UHFFFAOYSA-N 4-[4-[5-chloro-3-[3-(4-ethylpiperazin-1-yl)propoxy]-2-methylphenyl]piperazin-1-yl]-3-ethyl-2h-pyrazolo[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CN(CC)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(CC)=NNC=3N=CN=2)=C1C AWFYCBLBBLZBBT-UHFFFAOYSA-N 0.000 description 1
• OUWGWVYCIKZPJZ-UHFFFAOYSA-N 4-[5-(2-ethylbutoxy)-2-methyl-3-(2-pyrrolidin-1-ylethylamino)phenyl]piperazine-1-carboxylic acid Chemical compound CCC(CC)COC1=CC(=C(C(=C1)N2CCN(CC2)C(=O)O)C)NCCN3CCCC3 OUWGWVYCIKZPJZ-UHFFFAOYSA-N 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• VIBJPUXLAKVICD-UHFFFAOYSA-N 4-bromo-2-chlorophenol Chemical compound OC1=CC=C(Br)C=C1Cl VIBJPUXLAKVICD-UHFFFAOYSA-N 0.000 description 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
• CVFQKJBAFPUOOE-UHFFFAOYSA-N 4-methyl-3-[2-pyrrolidin-1-ylethyl-(2,2,2-trifluoroacetyl)amino]-5-[4-(2,2,2-trifluoroacetyl)piperazin-1-yl]benzoic acid Chemical compound CC1=C(N(CCN2CCCC2)C(=O)C(F)(F)F)C=C(C(O)=O)C=C1N1CCN(C(=O)C(F)(F)F)CC1 CVFQKJBAFPUOOE-UHFFFAOYSA-N 0.000 description 1
• PBIOBGXIHSGZEZ-UHFFFAOYSA-N 4-methyl-3-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]-5-(2-pyrrolidin-1-ylethylamino)benzoic acid Chemical compound C1=C(C(O)=O)C=C(N2CCN(CC2)C(=O)OC(C)(C)C)C(C)=C1NCCN1CCCC1 PBIOBGXIHSGZEZ-UHFFFAOYSA-N 0.000 description 1
• UPIPEVYDDHOZJJ-UHFFFAOYSA-N 5-(2,2-dimethylpropoxy)-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(OCC(C)(C)C)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 UPIPEVYDDHOZJJ-UHFFFAOYSA-N 0.000 description 1
• KJGKXCRDIOPBQR-UHFFFAOYSA-N 5-(2-ethylbutoxy)-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(OCC(CC)CC)=CC=1NCCN1CCCC1 KJGKXCRDIOPBQR-UHFFFAOYSA-N 0.000 description 1
• YCMKEWPJERHVGV-UHFFFAOYSA-N 5-(2-methoxyethoxy)-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(OCCOC)=CC=1NCCN1CCCC1 YCMKEWPJERHVGV-UHFFFAOYSA-N 0.000 description 1
• DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
• RJRXXFWGGQCTAJ-UHFFFAOYSA-N 5-(cyclobutylmethoxy)-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(OCC2CCC2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 RJRXXFWGGQCTAJ-UHFFFAOYSA-N 0.000 description 1
• HTZKMBJOSMXQBG-UHFFFAOYSA-N 5-(cyclohexylmethoxy)-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(OCC2CCCCC2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 HTZKMBJOSMXQBG-UHFFFAOYSA-N 0.000 description 1
• HBWVVLFIYSFTDP-UHFFFAOYSA-N 5-(cyclopentylmethoxy)-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(OCC2CCCC2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 HBWVVLFIYSFTDP-UHFFFAOYSA-N 0.000 description 1
• GEMJHKMQCUNCOZ-UHFFFAOYSA-N 5-(cyclopropylmethoxy)-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(OCC2CC2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 GEMJHKMQCUNCOZ-UHFFFAOYSA-N 0.000 description 1
• MTEKHXNKEDKMHO-UHFFFAOYSA-N 5-[(2,2-difluorocyclopropyl)methoxy]-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(OCC2C(C2)(F)F)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 MTEKHXNKEDKMHO-UHFFFAOYSA-N 0.000 description 1
• VHYFWRJMROZALU-UHFFFAOYSA-N 5-bromo-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(Br)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 VHYFWRJMROZALU-UHFFFAOYSA-N 0.000 description 1
• FKAJOXHDKWTYQZ-UHFFFAOYSA-N 5-butoxy-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(OCCCC)=CC=1NCCN1CCCC1 FKAJOXHDKWTYQZ-UHFFFAOYSA-N 0.000 description 1
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
• MYVSNTMBLBJVAR-UHFFFAOYSA-N 5-chloro-2-methoxy-3-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]benzoic acid Chemical compound C1=C(Cl)C=C(C(O)=O)C(OC)=C1N1CCN(C(=O)OC(C)(C)C)CC1 MYVSNTMBLBJVAR-UHFFFAOYSA-N 0.000 description 1
• ANFXMRFYWDHHHT-UHFFFAOYSA-N 5-chloro-2-methyl-3-[4-(3-propan-2-yl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)aniline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(C(C)C)NN=C2N=CN=C1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1NCCN1CCCC1 ANFXMRFYWDHHHT-UHFFFAOYSA-N 0.000 description 1
• WOLNFTWSDNSDEN-UHFFFAOYSA-N 5-chloro-2-methyl-3-[4-[3-(2-methylpropyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)aniline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC(C)C)NN=C2N=CN=C1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1NCCN1CCCC1 WOLNFTWSDNSDEN-UHFFFAOYSA-N 0.000 description 1
• WUJBPUKAUVTGRW-UHFFFAOYSA-N 5-chloro-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C1=C(Cl)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 WUJBPUKAUVTGRW-UHFFFAOYSA-N 0.000 description 1
• NUCGEMSYYFGJRC-UHFFFAOYSA-N 5-chloro-3-[4-(3-cyclopropyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C(N2CCN(CC2)C=2C3=C(C4CC4)NN=C3N=CN=2)C(C)=C1NCCN1CCCC1 NUCGEMSYYFGJRC-UHFFFAOYSA-N 0.000 description 1
• QCXASTMRNOVYOP-UHFFFAOYSA-N 5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1NCCN1CCCC1 QCXASTMRNOVYOP-UHFFFAOYSA-N 0.000 description 1
• SQYMZORQAUTURP-UHFFFAOYSA-N 5-ethoxy-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(OCC)=CC=1NCCN1CCCC1 SQYMZORQAUTURP-UHFFFAOYSA-N 0.000 description 1
• JPGPPHISZFDACG-UHFFFAOYSA-N 5-ethyl-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC=1C(N2CCNCC2)=CC(CC)=CC=1NCCN1CCCC1 JPGPPHISZFDACG-UHFFFAOYSA-N 0.000 description 1
• HCTCMHHQMDCVGD-UHFFFAOYSA-N 5-ethylsulfonyl-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline;hydrochloride Chemical compound Cl.CC=1C(N2CCNCC2)=CC(S(=O)(=O)CC)=CC=1NCCN1CCCC1 HCTCMHHQMDCVGD-UHFFFAOYSA-N 0.000 description 1
• RJMAPNOOJUQGCI-UHFFFAOYSA-N 5-ethynyl-2-methyl-3-piperazin-1-yl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(C#C)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 RJMAPNOOJUQGCI-UHFFFAOYSA-N 0.000 description 1
• KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 description 1
• ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 1
• MWRLTPXFGZXUKB-UHFFFAOYSA-N 6-[4-(2-methylphenyl)piperazin-1-yl]-7h-purine Chemical compound CC1=CC=CC=C1N1CCN(C=2C=3N=CNC=3N=CN=2)CC1 MWRLTPXFGZXUKB-UHFFFAOYSA-N 0.000 description 1
• IQFNNPBWPNNACU-UHFFFAOYSA-N 6-[4-(4-chlorophenyl)piperazin-1-yl]-7h-purine Chemical compound C1=CC(Cl)=CC=C1N1CCN(C=2C=3N=CNC=3N=CN=2)CC1 IQFNNPBWPNNACU-UHFFFAOYSA-N 0.000 description 1
• FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
• SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 208000013824 Acidemia Diseases 0.000 description 1
• 208000010444 Acidosis Diseases 0.000 description 1
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
• 108010088751 Albumins Proteins 0.000 description 1
• 102000009027 Albumins Human genes 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• 102000007299 Amphiregulin Human genes 0.000 description 1
• 108010033760 Amphiregulin Proteins 0.000 description 1
• DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
• 102400001242 Betacellulin Human genes 0.000 description 1
• 101800001382 Betacellulin Proteins 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 206010073106 Bone giant cell tumour malignant Diseases 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
• NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
• LZTAFOFVUWLZLV-UHFFFAOYSA-N C(O)CN.CN(C)C Chemical compound C(O)CN.CN(C)C LZTAFOFVUWLZLV-UHFFFAOYSA-N 0.000 description 1
• NLTYMRXEVHKXQJ-UHFFFAOYSA-N C1=NN(C2=C1C(=NC=N2)Cl)Br Chemical compound C1=NN(C2=C1C(=NC=N2)Cl)Br NLTYMRXEVHKXQJ-UHFFFAOYSA-N 0.000 description 1
• HIHDQUDZEYDANU-UHFFFAOYSA-N C1CN(CCC1C2=CC=CC=C2)C3=NC=NC4=C3C=NN4 Chemical compound C1CN(CCC1C2=CC=CC=C2)C3=NC=NC4=C3C=NN4 HIHDQUDZEYDANU-UHFFFAOYSA-N 0.000 description 1
• FBRXHYNGRXFQLH-UHFFFAOYSA-N CC(CCC#CC1=CC=CC=C1)C2=CC3=CC=CC=C3C=C2 Chemical compound CC(CCC#CC1=CC=CC=C1)C2=CC3=CC=CC=C3C=C2 FBRXHYNGRXFQLH-UHFFFAOYSA-N 0.000 description 1
• YTCHPCFFGGHTIH-UHFFFAOYSA-N CC1=C(C=C(C=C1N(CCN2CCCC2)C(=O)C(F)(F)F)OC(=O)N)N3CCN(CC3)C(=O)C(F)(F)F Chemical compound CC1=C(C=C(C=C1N(CCN2CCCC2)C(=O)C(F)(F)F)OC(=O)N)N3CCN(CC3)C(=O)C(F)(F)F YTCHPCFFGGHTIH-UHFFFAOYSA-N 0.000 description 1
• FOKLBIQRIMWIBL-UHFFFAOYSA-N CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)C(=O)N(C)OC)NCCN3CCCC3 Chemical compound CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)C(=O)N(C)OC)NCCN3CCCC3 FOKLBIQRIMWIBL-UHFFFAOYSA-N 0.000 description 1
• WCMVKPQWWVOFJU-UHFFFAOYSA-N CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)CCC(C)(C)C)NCCN3CCCC3 Chemical compound CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)CCC(C)(C)C)NCCN3CCCC3 WCMVKPQWWVOFJU-UHFFFAOYSA-N 0.000 description 1
• MQDNXMKFOBGNPE-UHFFFAOYSA-N CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)Cl)NCCN(C)C Chemical compound CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)Cl)NCCN(C)C MQDNXMKFOBGNPE-UHFFFAOYSA-N 0.000 description 1
• CWFRZJSUDFCKNL-UHFFFAOYSA-N CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)OS(=O)(=O)C(F)(F)F)NCCN3CCCC3 Chemical compound CC1=C(C=C(C=C1N2CCN(CC2)C(=O)O)OS(=O)(=O)C(F)(F)F)NCCN3CCCC3 CWFRZJSUDFCKNL-UHFFFAOYSA-N 0.000 description 1
• GOTZFIBGBBDDJY-UHFFFAOYSA-N CC1=C(I)C=C(Cl)C=C1N1CCN(C(O)=O)CC1 Chemical compound CC1=C(I)C=C(Cl)C=C1N1CCN(C(O)=O)CC1 GOTZFIBGBBDDJY-UHFFFAOYSA-N 0.000 description 1
• AYTGGFYAQLGIAP-UHFFFAOYSA-N CCC1=C2C(=NN1)N=CN=C2N3CCN(CC3)C4=CC(=CC(=C4OC)C(=O)O)Cl Chemical compound CCC1=C2C(=NN1)N=CN=C2N3CCN(CC3)C4=CC(=CC(=C4OC)C(=O)O)Cl AYTGGFYAQLGIAP-UHFFFAOYSA-N 0.000 description 1
• ASBYUYDCVPGWJR-UHFFFAOYSA-N CCN(CC)C(C)OC1=CC(=CC(=C1C)N2CCNCC2)Cl Chemical compound CCN(CC)C(C)OC1=CC(=CC(=C1C)N2CCNCC2)Cl ASBYUYDCVPGWJR-UHFFFAOYSA-N 0.000 description 1
• 102000038625 CMGCs Human genes 0.000 description 1
• 108091007913 CMGCs Proteins 0.000 description 1
• LUYKTXSJCPPLHD-UHFFFAOYSA-N CN(C(=O)C1=CC(=CC(=C1)N2CCN(CC2)C(=O)O)NCCN3CCCC3)OC Chemical compound CN(C(=O)C1=CC(=CC(=C1)N2CCN(CC2)C(=O)O)NCCN3CCCC3)OC LUYKTXSJCPPLHD-UHFFFAOYSA-N 0.000 description 1
• YSXPUAUXTOXTGT-UHFFFAOYSA-N CN(C(=O)C1=CC(=CC(=C1)N2CCNCC2)NCCN3CCCC3)OC Chemical compound CN(C(=O)C1=CC(=CC(=C1)N2CCNCC2)NCCN3CCCC3)OC YSXPUAUXTOXTGT-UHFFFAOYSA-N 0.000 description 1
• JOKBTBYKTFJMTE-UHFFFAOYSA-N CN(C)CCNC(=O)C1=C(C(=CC(=C1)Cl)N2CCNCC2)OC Chemical compound CN(C)CCNC(=O)C1=C(C(=CC(=C1)Cl)N2CCNCC2)OC JOKBTBYKTFJMTE-UHFFFAOYSA-N 0.000 description 1
• BDQHKOFICQVUPE-UHFFFAOYSA-N COC(=O)C1=CC(=CC(=C1)N2CCN(CC2)C(=O)O)NCCN3CCCC3 Chemical compound COC(=O)C1=CC(=CC(=C1)N2CCN(CC2)C(=O)O)NCCN3CCCC3 BDQHKOFICQVUPE-UHFFFAOYSA-N 0.000 description 1
• 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 description 1
• 102100022789 Calcium/calmodulin-dependent protein kinase type IV Human genes 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• 208000005623 Carcinogenesis Diseases 0.000 description 1
• 208000009458 Carcinoma in Situ Diseases 0.000 description 1
• 206010008263 Cervical dysplasia Diseases 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 201000005262 Chondroma Diseases 0.000 description 1
• 208000005243 Chondrosarcoma Diseases 0.000 description 1
• 201000009047 Chordoma Diseases 0.000 description 1
• 208000006332 Choriocarcinoma Diseases 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• 206010048832 Colon adenoma Diseases 0.000 description 1
• 208000035473 Communicable disease Diseases 0.000 description 1
• 206010010356 Congenital anomaly Diseases 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 1
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
• 206010061818 Disease progression Diseases 0.000 description 1
• 101100291385 Drosophila melanogaster p38a gene Proteins 0.000 description 1
• 206010013710 Drug interaction Diseases 0.000 description 1
• 208000000471 Dysplastic Nevus Syndrome Diseases 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 206010014967 Ependymoma Diseases 0.000 description 1
• 101800003838 Epidermal growth factor Proteins 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 208000006168 Ewing Sarcoma Diseases 0.000 description 1
• 101000933374 Gallus gallus Brain-specific homeobox/POU domain protein 3 Proteins 0.000 description 1
• 208000021309 Germ cell tumor Diseases 0.000 description 1
• 208000007569 Giant Cell Tumors Diseases 0.000 description 1
• 201000005409 Gliomatosis cerebri Diseases 0.000 description 1
• 206010018404 Glucagonoma Diseases 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 206010018691 Granuloma Diseases 0.000 description 1
• 239000007818 Grignard reagent Substances 0.000 description 1
• 108010009202 Growth Factor Receptors Proteins 0.000 description 1
• 102000009465 Growth Factor Receptors Human genes 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 208000002927 Hamartoma Diseases 0.000 description 1
• 101800001649 Heparin-binding EGF-like growth factor Proteins 0.000 description 1
• 102400001369 Heparin-binding EGF-like growth factor Human genes 0.000 description 1
• 102100021866 Hepatocyte growth factor Human genes 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 101100287682 Homo sapiens CAMK2G gene Proteins 0.000 description 1
• 101100126883 Homo sapiens CAMK4 gene Proteins 0.000 description 1
• 101000898034 Homo sapiens Hepatocyte growth factor Proteins 0.000 description 1
• 101001076408 Homo sapiens Interleukin-6 Proteins 0.000 description 1
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
• 101000868152 Homo sapiens Son of sevenless homolog 1 Proteins 0.000 description 1
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
• PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
• 208000031226 Hyperlipidaemia Diseases 0.000 description 1
• 206010061598 Immunodeficiency Diseases 0.000 description 1
• 208000029462 Immunodeficiency disease Diseases 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 0.000 description 1
• 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
• 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 1
• 108010044467 Isoenzymes Proteins 0.000 description 1
• 208000002260 Keloid Diseases 0.000 description 1
• 206010023330 Keloid scar Diseases 0.000 description 1
• 208000008839 Kidney Neoplasms Diseases 0.000 description 1
• SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
• ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
• DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• JTTHKOPSMAVJFE-VIFPVBQESA-N L-homophenylalanine Chemical compound OC(=O)[C@@H](N)CCC1=CC=CC=C1 JTTHKOPSMAVJFE-VIFPVBQESA-N 0.000 description 1
• UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
• AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
• JZKXXXDKRQWDET-QMMMGPOBSA-N L-m-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(O)=C1 JZKXXXDKRQWDET-QMMMGPOBSA-N 0.000 description 1
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
• SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
• LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 1
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
• QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
• 241001313288 Labia Species 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 239000012448 Lithium borohydride Substances 0.000 description 1
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
• 108091054455 MAP kinase family Proteins 0.000 description 1
• 102000043136 MAP kinase family Human genes 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 201000009906 Meningitis Diseases 0.000 description 1
• 208000001145 Metabolic Syndrome Diseases 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 101100268066 Mus musculus Zap70 gene Proteins 0.000 description 1
• 201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
• 208000014767 Myeloproliferative disease Diseases 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 125000000815 N-oxide group Chemical group 0.000 description 1
• CGSZIBVFODKETF-UHFFFAOYSA-N NC(=O)c1c[nH]nc1N.Cc1nc(N2CCN(CC2)c2cc(Cl)ccc2C)c2cn[nH]c2n1 Chemical compound NC(=O)c1c[nH]nc1N.Cc1nc(N2CCN(CC2)c2cc(Cl)ccc2C)c2cn[nH]c2n1 CGSZIBVFODKETF-UHFFFAOYSA-N 0.000 description 1
• 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 description 1
• 102400000058 Neuregulin-1 Human genes 0.000 description 1
• 108090000556 Neuregulin-1 Proteins 0.000 description 1
• 206010029260 Neuroblastoma Diseases 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
• 101710163270 Nuclease Proteins 0.000 description 1
• 108091005461 Nucleic proteins Chemical group 0.000 description 1
• 208000022873 Ocular disease Diseases 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 201000010133 Oligodendroglioma Diseases 0.000 description 1
• 108091034117 Oligonucleotide Proteins 0.000 description 1
• 102000015636 Oligopeptides Human genes 0.000 description 1
• 108010038807 Oligopeptides Proteins 0.000 description 1
• BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
• 208000000035 Osteochondroma Diseases 0.000 description 1
• 206010031252 Osteomyelitis Diseases 0.000 description 1
• 206010033128 Ovarian cancer Diseases 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 102100026450 POU domain, class 3, transcription factor 4 Human genes 0.000 description 1
• 101710133389 POU domain, class 3, transcription factor 4 Proteins 0.000 description 1
• 208000031481 Pathologic Constriction Diseases 0.000 description 1
• 208000034038 Pathologic Neovascularization Diseases 0.000 description 1
• 101150003085 Pdcl gene Proteins 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
• 235000011613 Pinus brutia Nutrition 0.000 description 1
• 241000018646 Pinus brutia Species 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
• 101710098940 Pro-epidermal growth factor Proteins 0.000 description 1
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 description 1
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 description 1
• 108091005682 Receptor kinases Proteins 0.000 description 1
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
• 102100029986 Receptor tyrosine-protein kinase erbB-3 Human genes 0.000 description 1
• 101710100969 Receptor tyrosine-protein kinase erbB-3 Proteins 0.000 description 1
• 102100029981 Receptor tyrosine-protein kinase erbB-4 Human genes 0.000 description 1
• 101710100963 Receptor tyrosine-protein kinase erbB-4 Proteins 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 201000000582 Retinoblastoma Diseases 0.000 description 1
• 102000002278 Ribosomal Proteins Human genes 0.000 description 1
• 108010000605 Ribosomal Proteins Proteins 0.000 description 1
• 208000000097 Sertoli-Leydig cell tumor Diseases 0.000 description 1
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
• 239000005708 Sodium hypochlorite Substances 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
• SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
• 241000590876 Steroma Species 0.000 description 1
• 108010090804 Streptavidin Proteins 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 1
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 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 description 1
• AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
• 239000004473 Threonine Substances 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
• 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 description 1
• KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
• 108010053096 Vascular Endothelial Growth Factor Receptor-1 Proteins 0.000 description 1
• 102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 description 1
• 235000009754 Vitis X bourquina Nutrition 0.000 description 1
• 235000012333 Vitis X labruscana Nutrition 0.000 description 1
• 240000006365 Vitis vinifera Species 0.000 description 1
• 235000014787 Vitis vinifera Nutrition 0.000 description 1
• 208000008383 Wilms tumor Diseases 0.000 description 1
• 206010052428 Wound Diseases 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• 206010048214 Xanthoma Diseases 0.000 description 1
• 206010048215 Xanthomatosis Diseases 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
• XLRXYRAUOHNGIX-UHFFFAOYSA-N [1-(3-chlorophenyl)-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-2-yl]methanol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1CO)CCN1C1=CC=CC(Cl)=C1 XLRXYRAUOHNGIX-UHFFFAOYSA-N 0.000 description 1
• CSXVULNEGWUJTI-UHFFFAOYSA-N [1-(3-chlorophenyl)piperazin-2-yl]methanol Chemical compound OCC1CNCCN1C1=CC=CC(Cl)=C1 CSXVULNEGWUJTI-UHFFFAOYSA-N 0.000 description 1
• SBCJBPYSEVWVHA-UHFFFAOYSA-N [3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]-cyclopropylmethanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C(=O)C2CC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 SBCJBPYSEVWVHA-UHFFFAOYSA-N 0.000 description 1
• JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
• WHQMWRNYGCEIGG-UHFFFAOYSA-N [4-methyl-3-piperazin-1-yl-5-(2-pyrrolidin-1-ylethylamino)phenyl]-phenylmethanone;hydrochloride Chemical compound Cl.C1=C(C(=O)C=2C=CC=CC=2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 WHQMWRNYGCEIGG-UHFFFAOYSA-N 0.000 description 1
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
• 230000001594 aberrant effect Effects 0.000 description 1
• 230000005856 abnormality Effects 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• MTZVPMQRZJBIJM-UHFFFAOYSA-N acetic acid;1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)phenyl]propan-1-one Chemical compound CC(O)=O.CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)CC)=CC=1NCCN1CCCC1 MTZVPMQRZJBIJM-UHFFFAOYSA-N 0.000 description 1
• CBJTZQYOVHNMDH-UHFFFAOYSA-N acetic acid;1-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(2-pyrrolidin-1-ylethylamino)phenyl]butan-1-one Chemical compound CC(O)=O.C=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)CCC)=CC=1NCCN1CCCC1 CBJTZQYOVHNMDH-UHFFFAOYSA-N 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• MZQDCTLURFUBTB-UHFFFAOYSA-N acetic acid;3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(2-phenylethyl)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC(O)=O.C1=C(CCC=2C=CC=CC=2)C=C(N2CCN(CC2)C=2C3=C(Br)NN=C3N=CN=2)C(C)=C1NCCN1CCCC1 MZQDCTLURFUBTB-UHFFFAOYSA-N 0.000 description 1
• MXZXALUWZPADSD-UHFFFAOYSA-N acetic acid;3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-(oxolan-2-ylmethoxy)-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC(O)=O.C1=C(OCC2OCCC2)C=C(N2CCN(CC2)C=2C3=C(Br)NN=C3N=CN=2)C(C)=C1NCCN1CCCC1 MXZXALUWZPADSD-UHFFFAOYSA-N 0.000 description 1
• DDQLGSVUJGRGMU-UHFFFAOYSA-N acetic acid;3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-5-propoxy-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC(O)=O.CC=1C(N2CCN(CC2)C=2C3=C(Br)NN=C3N=CN=2)=CC(OCCC)=CC=1NCCN1CCCC1 DDQLGSVUJGRGMU-UHFFFAOYSA-N 0.000 description 1
• RLRZQKOLHYZQCB-UHFFFAOYSA-N acetic acid;3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC(O)=O.C=1C(N2CCN(CC2)C=2C3=C(Br)NN=C3N=CN=2)=CC(Cl)=CC=1NCCN1CCCC1 RLRZQKOLHYZQCB-UHFFFAOYSA-N 0.000 description 1
• MSHQLYVBLWUOPH-UHFFFAOYSA-N acetic acid;3-bromo-5-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC(O)=O.C12=C(Br)NN=C2N=CN=C1N(CC1)CCN1C(C=1)=CC(Br)=CC=1NCCN1CCCC1 MSHQLYVBLWUOPH-UHFFFAOYSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 239000012042 active reagent Substances 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 239000002313 adhesive film Substances 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 239000003463 adsorbent Substances 0.000 description 1
• 206010064930 age-related macular degeneration Diseases 0.000 description 1
• 229940072056 alginate Drugs 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
• 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 1
• 125000002877 alkyl aryl group Chemical group 0.000 description 1
• 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 1
• 150000001371 alpha-amino acids Chemical class 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 230000009435 amidation Effects 0.000 description 1
• 238000007112 amidation reaction Methods 0.000 description 1
• 229940024606 amino acid Drugs 0.000 description 1
• 235000001014 amino acid Nutrition 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 125000002431 aminoalkoxy group Chemical group 0.000 description 1
• BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000001099 ammonium carbonate Substances 0.000 description 1
• 235000012501 ammonium carbonate Nutrition 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 230000003042 antagnostic effect Effects 0.000 description 1
• 238000011122 anti-angiogenic therapy Methods 0.000 description 1
• 230000009949 anti-apoptotic pathway Effects 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 230000001028 anti-proliverative effect Effects 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
• 150000005840 aryl radicals Chemical class 0.000 description 1
• 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
• 125000005110 aryl thio group Chemical group 0.000 description 1
• 235000009582 asparagine Nutrition 0.000 description 1
• 229960001230 asparagine Drugs 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 238000011914 asymmetric synthesis Methods 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
• 230000003796 beauty Effects 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• PJHUABJTDFXYRQ-UHFFFAOYSA-N benzoyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CC=CC=C1 PJHUABJTDFXYRQ-UHFFFAOYSA-N 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• 229930008407 benzylideneacetone Natural products 0.000 description 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 229960003237 betaine Drugs 0.000 description 1
• 239000012867 bioactive agent Substances 0.000 description 1
• 238000002306 biochemical method Methods 0.000 description 1
• 229960002685 biotin Drugs 0.000 description 1
• 235000020958 biotin Nutrition 0.000 description 1
• 239000011616 biotin Substances 0.000 description 1
• 239000012455 biphasic mixture Substances 0.000 description 1
• IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
• 239000007844 bleaching agent Substances 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 230000036760 body temperature Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 201000002143 bronchus adenoma Diseases 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 239000004067 bulking agent Substances 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
• 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
• DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 230000036952 cancer formation Effects 0.000 description 1
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
• 125000001589 carboacyl group Chemical group 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 150000001720 carbohydrates Chemical class 0.000 description 1
• 231100000504 carcinogenesis Toxicity 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 235000019438 castor oil Nutrition 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 230000022131 cell cycle Effects 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 230000003833 cell viability Effects 0.000 description 1
• 230000019522 cellular metabolic process Effects 0.000 description 1
• 230000033077 cellular process Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 208000019065 cervical carcinoma Diseases 0.000 description 1
• 210000003679 cervix uteri Anatomy 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 125000003636 chemical group Chemical group 0.000 description 1
• 238000007385 chemical modification Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000012069 chiral reagent Substances 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• JECOSSASMXAXFV-UHFFFAOYSA-N chloroethane;hydrochloride Chemical compound Cl.CCCl JECOSSASMXAXFV-UHFFFAOYSA-N 0.000 description 1
• 201000005217 chondroblastoma Diseases 0.000 description 1
• 238000003200 chromosome mapping Methods 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229960004106 citric acid Drugs 0.000 description 1
• 229940061631 citric acid acetate Drugs 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 238000012875 competitive assay Methods 0.000 description 1
• 230000009137 competitive binding Effects 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 239000000039 congener Substances 0.000 description 1
• 239000012059 conventional drug carrier Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 208000029078 coronary artery disease Diseases 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 229960001681 croscarmellose sodium Drugs 0.000 description 1
• 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
• 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
• VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
• 239000004914 cyclooctane Substances 0.000 description 1
• URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
• 239000004913 cyclooctene Substances 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• XNDLVUWJVLBZQV-UHFFFAOYSA-N cyclopropyl-[4-methyl-3-piperazin-1-yl-5-(2-pyrrolidin-1-ylethylamino)phenyl]methanone;hydrochloride Chemical compound Cl.C1=C(C(=O)C2CC2)C=C(N2CCNCC2)C(C)=C1NCCN1CCCC1 XNDLVUWJVLBZQV-UHFFFAOYSA-N 0.000 description 1
• 208000002445 cystadenocarcinoma Diseases 0.000 description 1
• 230000003436 cytoskeletal effect Effects 0.000 description 1
• 125000005507 decahydroisoquinolyl group Chemical group 0.000 description 1
• 239000007857 degradation product Substances 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 230000030609 dephosphorylation Effects 0.000 description 1
• 238000006209 dephosphorylation reaction Methods 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 230000003831 deregulation Effects 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 239000003599 detergent Substances 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 206010012601 diabetes mellitus Diseases 0.000 description 1
• 229940039227 diagnostic agent Drugs 0.000 description 1
• 239000000032 diagnostic agent Substances 0.000 description 1
• WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• LWJYMKDMGMOTSB-UHFFFAOYSA-L dichlorotin;hydrate Chemical compound O.Cl[Sn]Cl LWJYMKDMGMOTSB-UHFFFAOYSA-L 0.000 description 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000029087 digestion Effects 0.000 description 1
• LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
• LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
• 125000004982 dihaloalkyl group Chemical group 0.000 description 1
• 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
• UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
• IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
• XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
• XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
• IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
• 125000005879 dioxolanyl group Chemical group 0.000 description 1
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
• 230000005750 disease progression Effects 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• QGBQGMHXBSLYLZ-UHFFFAOYSA-N ditert-butyl-(1-naphthalen-1-ylnaphthalen-2-yl)phosphane Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3P(C(C)(C)C)C(C)(C)C)=CC=CC2=C1 QGBQGMHXBSLYLZ-UHFFFAOYSA-N 0.000 description 1
• PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
• 238000007876 drug discovery Methods 0.000 description 1
• 230000002500 effect on skin Effects 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 229940116977 epidermal growth factor Drugs 0.000 description 1
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 1
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• CPDKCEYBTQSMGI-UHFFFAOYSA-N ethyl 2-cyano-4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)C(C#N)C(=O)C(F)(F)F CPDKCEYBTQSMGI-UHFFFAOYSA-N 0.000 description 1
• MFDCAYVUEFZJPH-UHFFFAOYSA-N ethyl 5-amino-1-tert-butyl-3-(trifluoromethyl)pyrazole-4-carboxylate Chemical compound CCOC(=O)C1=C(N)N(C(C)(C)C)N=C1C(F)(F)F MFDCAYVUEFZJPH-UHFFFAOYSA-N 0.000 description 1
• 229940093499 ethyl acetate Drugs 0.000 description 1
• 229940012017 ethylenediamine Drugs 0.000 description 1
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
• 210000003527 eukaryotic cell Anatomy 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 239000003885 eye ointment Substances 0.000 description 1
• 235000019197 fats Nutrition 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 108091071773 flk family Proteins 0.000 description 1
• 238000007667 floating Methods 0.000 description 1
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 239000003205 fragrance Substances 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 238000002825 functional assay Methods 0.000 description 1
• 230000002538 fungal effect Effects 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 238000001030 gas--liquid chromatography Methods 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 description 1
• 201000000052 gastrinoma Diseases 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 229940014259 gelatin Drugs 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 210000004907 gland Anatomy 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
• 229960002743 glutamine Drugs 0.000 description 1
• YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
• SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 239000003102 growth factor Substances 0.000 description 1
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 125000003106 haloaryl group Chemical group 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 208000006359 hepatoblastoma Diseases 0.000 description 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 1
• 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 238000013537 high throughput screening Methods 0.000 description 1
• 210000005260 human cell Anatomy 0.000 description 1
• 239000003906 humectant Substances 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 125000001183 hydrocarbyl group Chemical group 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
• 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 229960002591 hydroxyproline Drugs 0.000 description 1
• 201000001421 hyperglycemia Diseases 0.000 description 1
• 229960003685 imatinib mesylate Drugs 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 208000026278 immune system disease Diseases 0.000 description 1
• 238000003018 immunoassay Methods 0.000 description 1
• 230000007813 immunodeficiency Effects 0.000 description 1
• 201000004933 in situ carcinoma Diseases 0.000 description 1
• 238000012750 in vivo screening Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 206010022498 insulinoma Diseases 0.000 description 1
• 230000004068 intracellular signaling Effects 0.000 description 1
• 201000010985 invasive ductal carcinoma Diseases 0.000 description 1
• 229910052740 iodine Chemical group 0.000 description 1
• 239000011630 iodine Chemical group 0.000 description 1
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 229960000310 isoleucine Drugs 0.000 description 1
• AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 210000001117 keloid Anatomy 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 210000002429 large intestine Anatomy 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 231100001231 less toxic Toxicity 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 206010024627 liposarcoma Diseases 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 208000014018 liver neoplasm Diseases 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 239000008176 lyophilized powder Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 239000006249 magnetic particle Substances 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 201000004593 malignant giant cell tumor Diseases 0.000 description 1
• 201000000289 malignant teratoma Diseases 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• JZKXXXDKRQWDET-UHFFFAOYSA-N meta-tyrosine Natural products OC(=O)C(N)CC1=CC=CC(O)=C1 JZKXXXDKRQWDET-UHFFFAOYSA-N 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 230000001617 migratory effect Effects 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 239000003226 mitogen Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000003607 modifier Substances 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
• 208000010492 mucinous cystadenocarcinoma Diseases 0.000 description 1
• 238000007040 multi-step synthesis reaction Methods 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 208000025113 myeloid leukemia Diseases 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• 208000009091 myxoma Diseases 0.000 description 1
• ZVVXHWDADZXWBK-UHFFFAOYSA-N n'-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)C1=CC(Cl)=CC(N2CCNCC2)=C1C ZVVXHWDADZXWBK-UHFFFAOYSA-N 0.000 description 1
• GLNUVXISAQTTEO-UHFFFAOYSA-N n,n-diethyl-2-(2-methyl-3-piperazin-1-ylphenoxy)ethanamine;hydrochloride Chemical compound Cl.CCN(CC)CCOC1=CC=CC(N2CCNCC2)=C1C GLNUVXISAQTTEO-UHFFFAOYSA-N 0.000 description 1
• FUKWXUVCBRMHMG-UHFFFAOYSA-N n,n-diethyl-2-(3-piperazin-1-ylphenoxy)ethanamine;hydrochloride Chemical compound Cl.CCN(CC)CCOC1=CC=CC(N2CCNCC2)=C1 FUKWXUVCBRMHMG-UHFFFAOYSA-N 0.000 description 1
• PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
• ILBIXZPOMJFOJP-UHFFFAOYSA-N n,n-dimethylprop-2-yn-1-amine Chemical compound CN(C)CC#C ILBIXZPOMJFOJP-UHFFFAOYSA-N 0.000 description 1
• KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
• RKJGMXLKNOGMHW-UHFFFAOYSA-N n-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-n',n'-dimethylethane-1,2-diamine;hydrochloride Chemical compound Cl.CN(C)CCNC1=CC(Cl)=CC(N2CCNCC2)=C1C RKJGMXLKNOGMHW-UHFFFAOYSA-N 0.000 description 1
• OQWONLSUJJURJK-UHFFFAOYSA-N n-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-n'-ethyl-n'-methylethane-1,2-diamine Chemical compound CCN(C)CCNC1=CC(Cl)=CC(N2CCNCC2)=C1C OQWONLSUJJURJK-UHFFFAOYSA-N 0.000 description 1
• YNGIHIMHWBYNMM-UHFFFAOYSA-N n-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-n'-methyl-n'-propan-2-ylethane-1,2-diamine Chemical compound CC(C)N(C)CCNC1=CC(Cl)=CC(N2CCNCC2)=C1C YNGIHIMHWBYNMM-UHFFFAOYSA-N 0.000 description 1
• TTWBJIUVOHVAKS-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN(C)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C3=C(Br)NN=C3N=CN=2)=C1C TTWBJIUVOHVAKS-UHFFFAOYSA-N 0.000 description 1
• KBNOWZFLZPHXIY-UHFFFAOYSA-N n-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenyl]-n'-methyl-n'-propan-2-ylethane-1,2-diamine;hydrochloride Chemical compound Cl.CC(C)N(C)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C KBNOWZFLZPHXIY-UHFFFAOYSA-N 0.000 description 1
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 1
• ZYFWXHCSAMMYTM-UHFFFAOYSA-N n-[4-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]acetamide;hydrochloride Chemical compound Cl.C1=CC(NC(=O)C)=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 ZYFWXHCSAMMYTM-UHFFFAOYSA-N 0.000 description 1
• IPGFGIIRPVVRGH-UHFFFAOYSA-N n-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenyl]-n',n'-diethylethane-1,2-diamine;hydrochloride Chemical compound Cl.CCN(CC)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C IPGFGIIRPVVRGH-UHFFFAOYSA-N 0.000 description 1
• OQTCXSMHKFCLSO-UHFFFAOYSA-N n-[5-chloro-2-methyl-3-[4-[3-(trifluoromethyl)-2h-pyrazolo[3,4-d]pyrimidin-4-yl]piperazin-1-yl]phenyl]-n',n'-dimethylethane-1,2-diamine;hydrochloride Chemical compound Cl.CN(C)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(=NNC=3N=CN=2)C(F)(F)F)=C1C OQTCXSMHKFCLSO-UHFFFAOYSA-N 0.000 description 1
• AOQFWLLHXULMFU-UHFFFAOYSA-N n-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine;hydrochloride Chemical compound Cl.C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(NCCN(C)C)=C1C AOQFWLLHXULMFU-UHFFFAOYSA-N 0.000 description 1
• MDUURHLHERLXHI-UHFFFAOYSA-N n-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n'-ethyl-n'-methylethane-1,2-diamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCN(C)CCNC1=CC(Cl)=CC(N2CCN(CC2)C=2C3=C(CC)NN=C3N=CN=2)=C1C MDUURHLHERLXHI-UHFFFAOYSA-N 0.000 description 1
• GMNMSTOAHVFJKE-UHFFFAOYSA-N n-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenyl]-n'-methyl-n'-propan-2-ylethane-1,2-diamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(CC)NN=C2N=CN=C1N(CC1)CCN1C1=CC(Cl)=CC(NCCN(C)C(C)C)=C1C GMNMSTOAHVFJKE-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 239000013642 negative control Substances 0.000 description 1
• 201000008026 nephroblastoma Diseases 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 208000007538 neurilemmoma Diseases 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 208000004649 neutrophil actin dysfunction Diseases 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• 125000004433 nitrogen atom Chemical group N* 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 1
• 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 108020004707 nucleic acids Proteins 0.000 description 1
• 102000039446 nucleic acids Human genes 0.000 description 1
• 150000007523 nucleic acids Chemical group 0.000 description 1
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
• 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
• 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 238000011275 oncology therapy Methods 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 238000005457 optimization Methods 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
• 201000008482 osteoarthritis Diseases 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 1
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 1
• 239000006179 pH buffering agent Substances 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 208000021255 pancreatic insulinoma Diseases 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 238000003566 phosphorylation assay Methods 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 238000000053 physical method Methods 0.000 description 1
• 229920000768 polyamine Polymers 0.000 description 1
• 108091033319 polynucleotide Proteins 0.000 description 1
• 102000040430 polynucleotide Human genes 0.000 description 1
• 239000002157 polynucleotide Substances 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• 229920000137 polyphosphoric acid Polymers 0.000 description 1
• 229920001282 polysaccharide Polymers 0.000 description 1
• 239000005017 polysaccharide Substances 0.000 description 1
• 150000004804 polysaccharides Chemical class 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 239000013641 positive control Substances 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• 229910000160 potassium phosphate Inorganic materials 0.000 description 1
• 235000011009 potassium phosphates Nutrition 0.000 description 1
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 150000003140 primary amides Chemical class 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 230000004647 pro-inflammatory pathway Effects 0.000 description 1
• 108010035114 procamine Proteins 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 229960002429 proline Drugs 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• IAHIMVFWYADCJJ-UHFFFAOYSA-N prop-1-enylcyclohexane Chemical group CC=CC1CCCCC1 IAHIMVFWYADCJJ-UHFFFAOYSA-N 0.000 description 1
• TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
• 229960004063 propylene glycol Drugs 0.000 description 1
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 238000000159 protein binding assay Methods 0.000 description 1
• 238000001243 protein synthesis Methods 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 208000002815 pulmonary hypertension Diseases 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 230000008707 rearrangement Effects 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 230000000306 recurrent effect Effects 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 208000029922 reticulum cell sarcoma Diseases 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 206010039667 schwannoma Diseases 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 229910000077 silane Inorganic materials 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 229960002930 sirolimus Drugs 0.000 description 1
• 210000003625 skull Anatomy 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000001587 sorbitan monostearate Substances 0.000 description 1
• 235000011076 sorbitan monostearate Nutrition 0.000 description 1
• 229940035048 sorbitan monostearate Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 238000001179 sorption measurement Methods 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 230000036262 stenosis Effects 0.000 description 1
• 208000037804 stenosis Diseases 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 230000009211 stress pathway Effects 0.000 description 1
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 150000003462 sulfoxides Chemical class 0.000 description 1
• 125000004434 sulfur atom Chemical group 0.000 description 1
• XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical group S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 230000004083 survival effect Effects 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 230000009897 systematic effect Effects 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229960000235 temsirolimus Drugs 0.000 description 1
• 208000001608 teratocarcinoma Diseases 0.000 description 1
• ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
• ZXLIKOLOLSXZNT-UHFFFAOYSA-N tert-butyl-[3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-1-(oxan-2-yl)pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-ynoxy]-dimethylsilane Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C#CCO[Si](C)(C)C(C)(C)C)=NN(C=3N=CN=2)C2OCCCC2)CC1 ZXLIKOLOLSXZNT-UHFFFAOYSA-N 0.000 description 1
• 210000001550 testis Anatomy 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
• 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 229960004559 theobromine Drugs 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
• 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 description 1
• 125000002769 thiazolinyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000005309 thioalkoxy group Chemical group 0.000 description 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
• BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 102000027257 transmembrane receptors Human genes 0.000 description 1
• 108091008578 transmembrane receptors Proteins 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• XEFRYQPTIWSVGI-UHFFFAOYSA-N tributyl(2-methylbut-3-en-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C(C)C XEFRYQPTIWSVGI-UHFFFAOYSA-N 0.000 description 1
• 229940117013 triethanolamine oleate Drugs 0.000 description 1
• 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• 229960004799 tryptophan Drugs 0.000 description 1
• 208000022271 tubular adenoma Diseases 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
• 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• 208000010576 undifferentiated carcinoma Diseases 0.000 description 1
• 210000003708 urethra Anatomy 0.000 description 1
• VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
• 210000004291 uterus Anatomy 0.000 description 1
• 238000001291 vacuum drying Methods 0.000 description 1
• 239000004474 valine Substances 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 238000009736 wetting Methods 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1