CA2563699C - Kinase modulators and method of use - Google Patents

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Publication number

CA2563699C

CA2563699C CA2563699A CA2563699A CA2563699C CA 2563699 C CA2563699 C CA 2563699C CA 2563699 A CA2563699 A CA 2563699A CA 2563699 A CA2563699 A CA 2563699A CA 2563699 C CA2563699 C CA 2563699C

Authority

CA

Canada

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

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• 238000000034 method Methods 0.000 title claims abstract description 82
• 108091000080 Phosphotransferase Proteins 0.000 title claims abstract description 48
• 102000020233 phosphotransferase Human genes 0.000 title claims abstract description 48
• 150000001875 compounds Chemical class 0.000 claims abstract description 254
• 230000000694 effects Effects 0.000 claims abstract description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 40
• 201000010099 disease Diseases 0.000 claims abstract description 36
• 230000001413 cellular effect Effects 0.000 claims abstract description 10
• -1 4-(4-(5-chloro-2-methyl-3-[(2-pyrrolidin-1-ylethyl)oxy]phenyl}piperazin-1-yl)-(trifluoromethyl)-1H-pyrazolo [3,4-d]pyrimidine Chemical compound 0.000 claims description 242
• 239000000203 mixture Substances 0.000 claims description 167
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
• 239000003795 chemical substances by application Substances 0.000 claims description 73
• 125000000217 alkyl group Chemical group 0.000 claims description 59
• 125000000623 heterocyclic group Chemical group 0.000 claims description 56
• 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 54
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 37
• 125000004122 cyclic group Chemical group 0.000 claims description 35
• 125000003107 substituted aryl group Chemical group 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 26
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 20
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 239000000651 prodrug Substances 0.000 claims description 10
• 229940002612 prodrug Drugs 0.000 claims description 10
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 10
• 230000002159 abnormal effect Effects 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 238000001727 in vivo Methods 0.000 claims description 8
• 238000012216 screening Methods 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 230000005764 inhibitory process Effects 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
• 238000000338 in vitro Methods 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 230000002062 proliferating effect Effects 0.000 claims description 3
• 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
• 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
• TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 2
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 3
• 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
• 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 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
• TVFXHYIMTMBBRN-UHFFFAOYSA-N 4-[2-[2-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methylphenyl]phenoxy]ethyl]morpholine Chemical compound C1=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=CC=C1C1=CC=CC=C1OCCN1CCOCC1 TVFXHYIMTMBBRN-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
• RZOWKJSGXXYLBF-UHFFFAOYSA-N 5-bromo-3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(Br)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 RZOWKJSGXXYLBF-UHFFFAOYSA-N 0.000 claims 2
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
• LEDWWWTZELHRQW-SNAWJCMRSA-N (e)-3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]prop-2-enoic acid Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(\C=C\C(O)=O)=NNC=3N=CN=2)CC1 LEDWWWTZELHRQW-SNAWJCMRSA-N 0.000 claims 1
• FQPXLXBETNISGH-VOTSOKGWSA-N (e)-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-enoic acid Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(\C=C\C(O)=O)=NNC=3N=CN=2)C(C)=C1CCCN1CCCC1 FQPXLXBETNISGH-VOTSOKGWSA-N 0.000 claims 1
• ZFCXABQUJNZWQJ-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-n-(1-methylpiperidin-4-yl)piperazine-2-carboxamide Chemical compound C=12C(CC)=NNC2=NC=NC=1N(C1)CCN(C=2C=C(Cl)C=CC=2)C1C(=O)NC1CCN(C)CC1 ZFCXABQUJNZWQJ-UHFFFAOYSA-N 0.000 claims 1
• ROKURXRPRCIPKT-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)-n-(2-morpholin-4-ylethyl)piperazine-2-carboxamide Chemical compound C=12C(CC)=NNC2=NC=NC=1N(C1)CCN(C=2C=C(Cl)C=CC=2)C1C(=O)NCCN1CCOCC1 ROKURXRPRCIPKT-UHFFFAOYSA-N 0.000 claims 1
• 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
• 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 1
• LFFNFWLFYKQSNU-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-[2-(dimethylamino)ethyl]-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazine-2-carboxamide Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1C(=O)NCCN(C)C)CCN1C1=CC=CC(Cl)=C1 LFFNFWLFYKQSNU-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 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
• 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 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
• 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 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
• 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 1
• IFFLKGMDBKQMAH-UHFFFAOYSA-N 2,4-diaminopyridine Chemical compound NC1=CC=NC(N)=C1 IFFLKGMDBKQMAH-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
• 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 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
• ACYZJWLNTOYYEJ-UHFFFAOYSA-N 2-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]pyridine-3-carboxamide Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=NC=CC=C1C(N)=O ACYZJWLNTOYYEJ-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
• MVPBFQKBNPPHJD-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 Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1Cl)=CC(F)=CC=1NCCN1CCCC1 MVPBFQKBNPPHJD-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-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
• XOOIIPHBBUZFOP-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 Chemical compound ClC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(F)=CC=1NCCN1CCCC1 XOOIIPHBBUZFOP-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
• 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 1
• 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 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
• 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 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
• 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 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
• 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 1
• 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 1
• OTROXNUGLUHDPM-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-(4,4,4-trifluoro-1,1-dimethoxybutyl)aniline Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(CCC(F)(F)F)(OC)OC)=CC=1NCCN1CCCC1 OTROXNUGLUHDPM-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
• CSWJHPQUGVGBIV-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-n-phenyl-5-(2-pyrrolidin-1-ylethylamino)benzamide Chemical compound C1=C(C(=O)NC=2C=CC=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 CSWJHPQUGVGBIV-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
• QNWLCNHMFYUSEU-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-n-pyridin-3-yl-5-(2-pyrrolidin-1-ylethylamino)benzamide Chemical compound C1=C(C(=O)NC=2C=NC=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 QNWLCNHMFYUSEU-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 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
• YBPFAYRBOUOWEW-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-(3,3-dimethylbut-1-ynyl)-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(C#CC(C)(C)C)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 YBPFAYRBOUOWEW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• OFIYBNFGPNSUBZ-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 Chemical compound C1=C(OCC2CCCCC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 OFIYBNFGPNSUBZ-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• 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 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
• SUHQXAOVYOYYQL-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-[2-(dimethylamino)ethylamino]-4-methyl-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC(NCCN(C)C)=C(C)C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1 SUHQXAOVYOYYQL-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
• VPUFQSGUFCOEEC-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 VPUFQSGUFCOEEC-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
• PYBBUIDGGUYWIF-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 Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(CC)=CC=1NCCN1CCCC1 PYBBUIDGGUYWIF-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• CYJZDLQSTXXZFE-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 Chemical compound C1=C(C#C)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 CYJZDLQSTXXZFE-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
• WCYZKEXUAINNCJ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n,4-dimethyl-5-(2-pyrrolidin-1-ylethylamino)benzamide Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)NC)=CC=1NCCN1CCCC1 WCYZKEXUAINNCJ-UHFFFAOYSA-N 0.000 claims 1
• RQZSAMQVTOQRIM-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n,4-dimethyl-n-propan-2-yl-5-(2-pyrrolidin-1-ylethylamino)benzamide Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)N(C)C(C)C)=CC=1NCCN1CCCC1 RQZSAMQVTOQRIM-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
• QDWCHVXMAABYCV-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n,n,4-trimethyl-5-(2-pyrrolidin-1-ylethylamino)benzamide Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)N(C)C)=CC=1NCCN1CCCC1 QDWCHVXMAABYCV-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
• ZBDHUMHGEAVULE-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-(4-chlorophenyl)-4-methyl-5-(2-pyrrolidin-1-ylethylamino)benzamide Chemical compound C1=C(C(=O)NC=2C=CC(Cl)=CC=2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 ZBDHUMHGEAVULE-UHFFFAOYSA-N 0.000 claims 1
• NXXUGYSAECRKOJ-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-(cyclopropylmethoxy)-4-methyl-5-(2-pyrrolidin-1-ylethylamino)benzamide Chemical compound C1=C(C(=O)NOCC2CC2)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1NCCN1CCCC1 NXXUGYSAECRKOJ-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
• DLSVCPCULIRHJL-UHFFFAOYSA-N 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-ethyl-4-methyl-5-(2-pyrrolidin-1-ylethylamino)benzamide Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)NCC)=CC=1NCCN1CCCC1 DLSVCPCULIRHJL-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
• RPVYHDOYPUWJGW-UHFFFAOYSA-N 3-[4-(3-chloro-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-n-(2-methylpropyl)benzamide Chemical compound CC(C)CNC(=O)C1=CC=C(C)C(N2CCN(CC2)C=2C=3C(Cl)=NNC=3N=CN=2)=C1 RPVYHDOYPUWJGW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• UBLLVZQZRNGUJQ-UHFFFAOYSA-N 3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-fluoro-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(F)=CC=1NCCN1CCCC1 UBLLVZQZRNGUJQ-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
• ZRENRORAOHMBRV-UHFFFAOYSA-N 3-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]-n,n-diethylprop-2-yn-1-amine Chemical compound C=12C(C#CCN(CC)CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C ZRENRORAOHMBRV-UHFFFAOYSA-N 0.000 claims 1
• CDYHYTPKRKNVFO-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 Chemical compound C=12C(CCCN(CC)CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC=C1C CDYHYTPKRKNVFO-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
• 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 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
• FFEQLBRPPNNIIS-UHFFFAOYSA-N 3-[4-[4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidin-3-yl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 FFEQLBRPPNNIIS-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
• 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
• 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 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-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
• JUTQDMDUNSWDQG-UHFFFAOYSA-N 3-bromo-4-[4-(4-chlorophenyl)piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=CC(Cl)=CC=C1N1CCN(C=2C=3C(Br)=NNC=3N=CN=2)CC1 JUTQDMDUNSWDQG-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
• 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 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
• DYGAFJNIWKKLRO-UHFFFAOYSA-N 3-bromo-4-[4-[2-chloro-5-[2-(2-pyrrolidin-1-ylethoxy)phenyl]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(Cl)=CC=C1C1=CC=CC=C1OCCN1CCCC1 DYGAFJNIWKKLRO-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• WBNGOBJGEOGHKO-UHFFFAOYSA-N 3-bromo-4-[4-[2-methyl-5-[2-(2-pyrrolidin-1-ylethoxy)phenyl]phenyl]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=C1OCCN1CCCC1 WBNGOBJGEOGHKO-UHFFFAOYSA-N 0.000 claims 1
• APSONKVXTVHOIR-UHFFFAOYSA-N 3-bromo-4-[4-[2-methyl-5-[3-(2-pyrrolidin-1-ylethoxy)phenyl]phenyl]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=C1C(C=1)=CC=CC=1OCCN1CCCC1 APSONKVXTVHOIR-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
• 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
• 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
• 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 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
• VIDMYEJOBBYUIX-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropoxy)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)=C1OCCCN1CCCCC1 VIDMYEJOBBYUIX-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
• NHBAOYDFPBHMMK-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropoxy)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)=C1OCCCN1CCCC1 NHBAOYDFPBHMMK-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• PGMCBJLKJSZOQM-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 Chemical compound C1CN(C)CCN1CCCOC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C PGMCBJLKJSZOQM-UHFFFAOYSA-N 0.000 claims 1
• AYSQAXKKEIXBFU-UHFFFAOYSA-N 3-bromo-4-[4-[5-chloro-2-methyl-3-[3-(4-methylpiperazin-1-yl)propyl]phenyl]piperazin-1-yl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCN1CCCC1=CC(Cl)=CC(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=C1C AYSQAXKKEIXBFU-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
• 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 1
• 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 1
• 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 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
• 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 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
• 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 1
• 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 1
• YOMXRYXICGNVKI-UHFFFAOYSA-N 4-(4-phenylpiperazin-1-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CCN1C1=CC=CC=C1 YOMXRYXICGNVKI-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• 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
• ONOIINDAHSHWOI-UHFFFAOYSA-N 4-[3-[3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenoxy]propyl]morpholine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C(C)=C1OCCCN1CCOCC1 ONOIINDAHSHWOI-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
• RKQYJHUYDPMEBV-UHFFFAOYSA-N 4-[3-[5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylphenoxy]propyl]morpholine Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCCCN1CCOCC1 RKQYJHUYDPMEBV-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
• 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 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 claims 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 claims 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 claims 1
• 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 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 claims 1
• 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 1
• 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 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
• YIDPQUCBGBVPJQ-UHFFFAOYSA-N 4-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methylquinoline Chemical compound C1=CC=CC2=NC(C)=CC(N3CCN(CC3)C=3C=4C(Br)=NNC=4N=CN=3)=C21 YIDPQUCBGBVPJQ-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
• 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 claims 1
• 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 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 claims 1
• 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 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 claims 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 claims 1
• 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 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
• 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 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
• 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 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
• WGCZFRRJTKPHPH-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-(3-pyrrolidin-1-ylprop-1-ynyl)-2h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C=2C=3C(C#CCN4CCCC4)=NNC=3N=CN=2)CC1 WGCZFRRJTKPHPH-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
• 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 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
• 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 1
• MVAPPIZCVCEAMZ-UHFFFAOYSA-N 4-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-3-[3-(4-methylpiperazin-1-yl)prop-1-ynyl]-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCN1CC#CC1=NNC2=NC=NC(N3CCN(CC3)C=3C(=CC=C(Cl)C=3)C)=C12 MVAPPIZCVCEAMZ-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
• 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 1
• 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 1
• 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 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
• 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 1
• 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 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
• 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 1
• 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 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
• 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 1
• 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 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
• 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 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 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
• 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 1
• 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 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
• AQZAQRSOINDPNL-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(2-pyrrolidin-1-ylethoxy)phenyl]piperazin-1-yl]-3-cyclopropyl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=C(Cl)C=C(N2CCN(CC2)C=2C=3C(C4CC4)=NNC=3N=CN=2)C(C)=C1OCCN1CCCC1 AQZAQRSOINDPNL-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
• BYGOXDLLNRNBPG-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-piperidin-1-ylpropoxy)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=1OCCCN1CCCCC1 BYGOXDLLNRNBPG-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
• MUVXQJBLKUTUPZ-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-(3-pyrrolidin-1-ylpropoxy)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=1OCCCN1CCCC1 MUVXQJBLKUTUPZ-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
• WPMSKZBISRKCCA-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 Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1OCC1CCN(C)CC1 WPMSKZBISRKCCA-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• 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 1
• WYQXCFRWJKGILM-UHFFFAOYSA-N 4-[4-[5-chloro-2-methyl-3-[3-(4-methylpiperazin-1-yl)propyl]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=1CCCN1CCN(C)CC1 WYQXCFRWJKGILM-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
• 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
• 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 1
• 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 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
• CNANJBQGWVKXDT-UHFFFAOYSA-N 5-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methyl-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound CC1=CC=C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)C=C1NCCN1CCCC1 CNANJBQGWVKXDT-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• ASTYUTBLDLIZJL-UHFFFAOYSA-N 5-chloro-2-methyl-3-[4-(3-methyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)aniline Chemical compound C=12C(C)=NNC2=NC=NC=1N(CC1)CCN1C(C=1C)=CC(Cl)=CC=1NCCN1CCCC1 ASTYUTBLDLIZJL-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
• 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 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
• 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 claims 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 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
• 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 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
• 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 1
• 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 1
• BNUGLBWENYXRLR-UHFFFAOYSA-N ethyl 4-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C(F)(F)F)N=C1N1CCN(C=2C=3C(CC)=NNC=3N=CN=2)CC1 BNUGLBWENYXRLR-UHFFFAOYSA-N 0.000 claims 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
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• MHJODCMTBYFIEJ-UHFFFAOYSA-N methyl 1-(3-chlorophenyl)-4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazine-2-carboxylate Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1C(=O)OC)CCN1C1=CC=CC(Cl)=C1 MHJODCMTBYFIEJ-UHFFFAOYSA-N 0.000 claims 1
• UUZYXVMMMLOUNS-UHFFFAOYSA-N methyl 3-[4-(3-bromo-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-4-methyl-5-(2-pyrrolidin-1-ylethylamino)benzoate Chemical compound CC=1C(N2CCN(CC2)C=2C=3C(Br)=NNC=3N=CN=2)=CC(C(=O)OC)=CC=1NCCN1CCCC1 UUZYXVMMMLOUNS-UHFFFAOYSA-N 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
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• PXZRFXUTDHJZIR-UHFFFAOYSA-N methyl 5-chloro-3-[4-(3-ethyl-2h-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-2-methoxybenzoate Chemical compound C=12C(CC)=NNC2=NC=NC=1N(CC1)CCN1C1=CC(Cl)=CC(C(=O)OC)=C1OC PXZRFXUTDHJZIR-UHFFFAOYSA-N 0.000 claims 1
• 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 1
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• 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
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• 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
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• 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 1
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• 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 1
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• 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
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