TWI606049B - 新穎激酶抑制劑 - Google Patents

Info

Publication number

TWI606049B

TWI606049B TW101114348A TW101114348A TWI606049B TW I606049 B TWI606049 B TW I606049B TW 101114348 A TW101114348 A TW 101114348A TW 101114348 A TW101114348 A TW 101114348A TW I606049 B TWI606049 B TW I606049B

Authority

TW

Taiwan

Prior art keywords

pyrazolo

pyrimidin

phenyl

amine

amino

Prior art date

2011-04-21

Links

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• Global Dossier
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• 229940043355 kinase inhibitor Drugs 0.000 title 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
• -1 NMe 2 Chemical group 0.000 claims description 211
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
• 125000004432 carbon atom Chemical group C* 0.000 claims description 69
• 229910052757 nitrogen Inorganic materials 0.000 claims description 66
• 229910052760 oxygen Inorganic materials 0.000 claims description 63
• 125000006413 ring segment Chemical group 0.000 claims description 60
• 229910052717 sulfur Inorganic materials 0.000 claims description 59
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
• 125000001072 heteroaryl group Chemical group 0.000 claims description 52
• 125000000217 alkyl group Chemical group 0.000 claims description 48
• 150000001875 compounds Chemical class 0.000 claims description 44
• 125000003118 aryl group Chemical group 0.000 claims description 41
• 125000005842 heteroatom Chemical group 0.000 claims description 41
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 40
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 35
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 34
• 125000003342 alkenyl group Chemical group 0.000 claims description 29
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 201000010099 disease Diseases 0.000 claims description 21
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 20
• 239000001301 oxygen Substances 0.000 claims description 20
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 16
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
• 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 16
• 229910052801 chlorine Inorganic materials 0.000 claims description 15
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
• 239000000460 chlorine Substances 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 239000011593 sulfur Substances 0.000 claims description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 11
• 206010028980 Neoplasm Diseases 0.000 claims description 10
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 9
• 239000005711 Benzoic acid Substances 0.000 claims description 9
• 206010020751 Hypersensitivity Diseases 0.000 claims description 9
• 235000010233 benzoic acid Nutrition 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• 239000011737 fluorine Substances 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 238000011282 treatment Methods 0.000 claims description 7
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
• 229930192474 thiophene Natural products 0.000 claims description 6
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 208000020084 Bone disease Diseases 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
• 230000002757 inflammatory effect Effects 0.000 claims description 4
• 208000030159 metabolic disease Diseases 0.000 claims description 4
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 3
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 3
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
• 208000026278 immune system disease Diseases 0.000 claims description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
• 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• ZMOZOYWHMMQBSE-UHFFFAOYSA-N 1-[4-[4-[[5-[3-(2h-tetrazol-5-yl)phenyl]-1h-pyrazolo[4,3-d]pyrimidin-7-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C(C=CC=2)C2=NNN=N2)=NC2=C1NN=C2 ZMOZOYWHMMQBSE-UHFFFAOYSA-N 0.000 claims description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• VLQMHJSEIMDRFY-UHFFFAOYSA-N 2,2-dimethyl-n-(5-thiophen-2-yl-1h-pyrazolo[4,3-d]pyrimidin-7-yl)-3,4-dihydro-1,4-benzothiazin-6-amine Chemical compound C=1C=C2SC(C)(C)CNC2=CC=1NC(C=1NN=CC=1N=1)=NC=1C1=CC=CS1 VLQMHJSEIMDRFY-UHFFFAOYSA-N 0.000 claims description 2
• JOOJVWJTRVOZHI-UHFFFAOYSA-N 2-[3-[7-[4-(4-methylpiperazin-1-yl)anilino]-1h-pyrazolo[4,3-d]pyrimidin-5-yl]phenyl]acetic acid Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C(CC(O)=O)C=CC=2)=NC2=C1NN=C2 JOOJVWJTRVOZHI-UHFFFAOYSA-N 0.000 claims description 2
• HUSHCEIUYCRXNA-UHFFFAOYSA-N 2-[7-[4-(4-methylpiperazin-1-yl)anilino]-1H-pyrazolo[4,3-d]pyrimidin-5-yl]phenol Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(C=2C(=CC=CC=2)O)=NC2=C1NN=C2 HUSHCEIUYCRXNA-UHFFFAOYSA-N 0.000 claims description 2
• XLSRABHWVWRRES-UHFFFAOYSA-N 2-methyl-2-[4-[(5-thiophen-2-yl-1h-pyrazolo[4,3-d]pyrimidin-7-yl)amino]phenyl]propanenitrile Chemical compound C1=CC(C(C)(C#N)C)=CC=C1NC1=NC(C=2SC=CC=2)=NC2=C1NN=C2 XLSRABHWVWRRES-UHFFFAOYSA-N 0.000 claims description 2
• GVLPORMJXSLDMG-UHFFFAOYSA-N 2-n-(5-thiophen-3-yl-1h-pyrazolo[4,3-d]pyrimidin-7-yl)cyclohexane-1,2-diamine Chemical compound NC1CCCCC1NC1=NC(C2=CSC=C2)=NC2=C1NN=C2 GVLPORMJXSLDMG-UHFFFAOYSA-N 0.000 claims description 2
• BJFKKVRLEGVAKM-UHFFFAOYSA-N 3-[(5-phenyl-1h-pyrazolo[4,3-d]pyrimidin-7-yl)amino]phenol Chemical compound OC1=CC=CC(NC=2C=3NN=CC=3N=C(N=2)C=2C=CC=CC=2)=C1 BJFKKVRLEGVAKM-UHFFFAOYSA-N 0.000 claims description 2
• UUUXBAWGROXTHD-UHFFFAOYSA-N 3-[(5-thiophen-2-yl-1h-pyrazolo[4,3-d]pyrimidin-7-yl)amino]phenol Chemical compound OC1=CC=CC(NC=2C=3NN=CC=3N=C(N=2)C=2SC=CC=2)=C1 UUUXBAWGROXTHD-UHFFFAOYSA-N 0.000 claims description 2
• UGDXVJJVZGBZIC-UHFFFAOYSA-N 3-[(5-thiophen-3-yl-1h-pyrazolo[4,3-d]pyrimidin-7-yl)amino]phenol Chemical compound OC1=CC=CC(NC=2C=3NN=CC=3N=C(N=2)C2=CSC=C2)=C1 UGDXVJJVZGBZIC-UHFFFAOYSA-N 0.000 claims description 2
• WTWWKDKVSHMLLR-UHFFFAOYSA-N 3-[7-(3,4-dimethoxyanilino)-1h-pyrazolo[4,3-d]pyrimidin-5-yl]benzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=CC=2)C(O)=O)=NC2=C1NN=C2 WTWWKDKVSHMLLR-UHFFFAOYSA-N 0.000 claims description 2
• ZDLAGFMFYMBVLW-UHFFFAOYSA-N 3-[7-[(2-oxo-3,4-dihydro-1h-quinolin-7-yl)amino]-1h-pyrazolo[4,3-d]pyrimidin-5-yl]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C=2N=C3C=NNC3=C(NC=3C=C4NC(=O)CCC4=CC=3)N=2)=C1 ZDLAGFMFYMBVLW-UHFFFAOYSA-N 0.000 claims description 2
• ATBLYBCGVAOBGB-UHFFFAOYSA-N 3-[[5-(1-methylpiperidin-4-yl)-1h-pyrazolo[4,3-d]pyrimidin-7-yl]amino]phenol Chemical compound C1CN(C)CCC1C1=NC(NC=2C=C(O)C=CC=2)=C(NN=C2)C2=N1 ATBLYBCGVAOBGB-UHFFFAOYSA-N 0.000 claims description 2
• KJXDTALIIDWUOL-UHFFFAOYSA-N 3-[[5-(3-methoxyphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-yl]amino]phenol Chemical compound COC1=CC=CC(C=2N=C3C=NNC3=C(NC=3C=C(O)C=CC=3)N=2)=C1 KJXDTALIIDWUOL-UHFFFAOYSA-N 0.000 claims description 2
• OTFXOQFBYNEWEL-UHFFFAOYSA-N 4-[(5-phenyl-1h-pyrazolo[4,3-d]pyrimidin-7-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1NN=C2 OTFXOQFBYNEWEL-UHFFFAOYSA-N 0.000 claims description 2
• BMTLOXCGFRDZBC-UHFFFAOYSA-N 4-[7-(3,4-dimethoxyanilino)-1h-pyrazolo[4,3-d]pyrimidin-5-yl]benzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=CC(=CC=2)C(O)=O)=NC2=C1NN=C2 BMTLOXCGFRDZBC-UHFFFAOYSA-N 0.000 claims description 2
• YJRHYVPXUHHHCC-UHFFFAOYSA-N 4-[7-(4-morpholin-4-ylanilino)-1h-pyrazolo[4,3-d]pyrimidin-5-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C(NN=C2)C2=N1 YJRHYVPXUHHHCC-UHFFFAOYSA-N 0.000 claims description 2
• CKNIUJVDSZXOPD-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-(5-phenyl-1h-pyrazolo[4,3-d]pyrimidin-7-yl)benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1NN=C2 CKNIUJVDSZXOPD-UHFFFAOYSA-N 0.000 claims description 2
• MROKWHQGWVNHON-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-[5-(6-pyrrolidin-1-ylpyridin-3-yl)-1h-pyrazolo[4,3-d]pyrimidin-7-yl]benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC(C=2C=NC(=CC=2)N2CCCC2)=NC2=C1NN=C2 MROKWHQGWVNHON-UHFFFAOYSA-N 0.000 claims description 2
• XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims description 2
• AJONMINAUOUCMS-UHFFFAOYSA-N 5-(1,3-benzothiazol-2-yl)-n-(3,4-dimethoxyphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2SC3=CC=CC=C3N=2)=NC2=C1NN=C2 AJONMINAUOUCMS-UHFFFAOYSA-N 0.000 claims description 2
• FTLPHZRAZNCVCS-UHFFFAOYSA-N 5-(1-methylpiperidin-4-yl)-n-(1h-pyrazol-5-yl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCC1C1=NC(NC2=NNC=C2)=C(NN=C2)C2=N1 FTLPHZRAZNCVCS-UHFFFAOYSA-N 0.000 claims description 2
• WPMQHPVSNTWSNG-UHFFFAOYSA-N 5-(1-methylpiperidin-4-yl)-n-(4-pyrrolidin-1-ylphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCC1C1=NC(NC=2C=CC(=CC=2)N2CCCC2)=C(NN=C2)C2=N1 WPMQHPVSNTWSNG-UHFFFAOYSA-N 0.000 claims description 2
• PNXQPEWUDIQAMP-UHFFFAOYSA-N 5-(1h-imidazol-2-yl)-n-[4-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(C=2NC=CN=2)=NC2=C1NN=C2 PNXQPEWUDIQAMP-UHFFFAOYSA-N 0.000 claims description 2
• RATWJNUMMDMKQC-UHFFFAOYSA-N 5-(1h-imidazol-5-yl)-n-[4-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(C=2NC=NC=2)=NC2=C1NN=C2 RATWJNUMMDMKQC-UHFFFAOYSA-N 0.000 claims description 2
• XQSUPQBYRKCANC-UHFFFAOYSA-N 5-(2,4-difluorophenyl)-n-(3,4-dimethoxyphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C(=CC(F)=CC=2)F)=NC2=C1NN=C2 XQSUPQBYRKCANC-UHFFFAOYSA-N 0.000 claims description 2
• ZIZAAGLVLUDWDA-UHFFFAOYSA-N 5-(2,6-difluorophenyl)-n-(3,4-dimethoxyphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C(=CC=CC=2F)F)=NC2=C1NN=C2 ZIZAAGLVLUDWDA-UHFFFAOYSA-N 0.000 claims description 2
• HFTIILIOIRLSCC-UHFFFAOYSA-N 5-(2,6-difluorophenyl)-n-(4-morpholin-4-ylphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound FC1=CC=CC(F)=C1C1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C(NN=C2)C2=N1 HFTIILIOIRLSCC-UHFFFAOYSA-N 0.000 claims description 2
• JDAIVYIVJDUUMB-UHFFFAOYSA-N 5-(2-fluorophenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(C=2C(=CC=CC=2)F)=NC2=C1NN=C2 JDAIVYIVJDUUMB-UHFFFAOYSA-N 0.000 claims description 2
• AQXIEFXSWOAZIU-UHFFFAOYSA-N 5-(2-fluorophenyl)-n-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(NC=3C=4NN=CC=4N=C(N=3)C=3C(=CC=CC=3)F)=CC=2)CC1 AQXIEFXSWOAZIU-UHFFFAOYSA-N 0.000 claims description 2
• DZOZUWJSHMBZNX-UHFFFAOYSA-N 5-(2-methoxyphenyl)-n-(4-morpholin-4-ylphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound COC1=CC=CC=C1C1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C(NN=C2)C2=N1 DZOZUWJSHMBZNX-UHFFFAOYSA-N 0.000 claims description 2
• BGRPDEUVYDPLTP-UHFFFAOYSA-N 5-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)-n-(3,4-dimethoxyphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=NC2=C1NN=C2 BGRPDEUVYDPLTP-UHFFFAOYSA-N 0.000 claims description 2
• UUOKJCIHYLEIBG-UHFFFAOYSA-N 5-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)-n-(4-morpholin-4-ylphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C2NCCOC2=CC=C1C(N=C1C=NNC1=1)=NC=1NC(C=C1)=CC=C1N1CCOCC1 UUOKJCIHYLEIBG-UHFFFAOYSA-N 0.000 claims description 2
• FWQOUBWDILYUPA-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-n-(1h-indazol-5-yl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(NC=2C=C3C=NNC3=CC=2)=C(NN=C2)C2=N1 FWQOUBWDILYUPA-UHFFFAOYSA-N 0.000 claims description 2
• SIDBWASODXNUNS-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-n-(1h-pyrazol-5-yl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(NC2=NNC=C2)=C(NN=C2)C2=N1 SIDBWASODXNUNS-UHFFFAOYSA-N 0.000 claims description 2
• NCNHBYZMCVDGPI-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-n-(4-pyrrolidin-1-ylphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(NC=2C=CC(=CC=2)N2CCCC2)=C(NN=C2)C2=N1 NCNHBYZMCVDGPI-UHFFFAOYSA-N 0.000 claims description 2
• UBXXXLDVMCSXSA-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-(3,4-dimethoxyphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(Cl)C=CC=2)=NC2=C1NN=C2 UBXXXLDVMCSXSA-UHFFFAOYSA-N 0.000 claims description 2
• ZIEAEWPLCARPDY-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-(4-morpholin-4-ylphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound ClC1=CC=CC(C=2N=C3C=NNC3=C(NC=3C=CC(=CC=3)N3CCOCC3)N=2)=C1 ZIEAEWPLCARPDY-UHFFFAOYSA-N 0.000 claims description 2
• JCFHDTLHHQQHRJ-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-(pyrrolidin-1-ylmethyl)phenyl]-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound COC1=CC=CC(C=2N=C3C=NNC3=C(NC=3C=CC(CN4CCCC4)=CC=3)N=2)=C1 JCFHDTLHHQQHRJ-UHFFFAOYSA-N 0.000 claims description 2
• SGUSHDKMLXNKKQ-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound COC1=CC=CC(C=2N=C3C=NNC3=C(NC=3C=CC(CN4CCN(C)CC4)=CC=3)N=2)=C1 SGUSHDKMLXNKKQ-UHFFFAOYSA-N 0.000 claims description 2
• MJANHHDQPLQYAE-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(4-morpholin-4-ylphenyl)-1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C(NN=C2)C2=N1 MJANHHDQPLQYAE-UHFFFAOYSA-N 0.000 claims description 2
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• IQJSYXZYUJASTE-UHFFFAOYSA-N 7-chloro-5-[3-(trifluoromethoxy)phenyl]-1h-pyrazolo[4,3-d]pyrimidine Chemical compound FC(F)(F)OC1=CC=CC(C2=NC3=CNN=C3C(Cl)=N2)=C1 IQJSYXZYUJASTE-UHFFFAOYSA-N 0.000 claims 1
• BEOLQNZIMHZMJT-UHFFFAOYSA-N 7-chloro-5-[3-(trifluoromethyl)phenyl]-1h-pyrazolo[4,3-d]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(C2=NC3=CNN=C3C(Cl)=N2)=C1 BEOLQNZIMHZMJT-UHFFFAOYSA-N 0.000 claims 1
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• ALPPGSBMHVCELA-WHUUVLPESA-N methyl (19E,21E,23E,25E,27E,29E,31E)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-17-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-1,3,5,7,9,13,37-heptahydroxy-18-methyl-11,15-dioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate methyl (19E,21E,23E,25E,27E,29E,31E)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,7,9,13,37-heptahydroxy-17-[5-hydroxy-7-[4-(methylamino)phenyl]-7-oxoheptan-2-yl]-18-methyl-11,15-dioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate Chemical compound CC1\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C(O[C@H]2[C@H]([C@@H](N)[C@H](O)[C@@H](C)O2)O)CC(O2)C(C(=O)OC)C(O)CC2(O)CC(O)CC(O)CC(O)CC(O)CC(=O)CC(O)CC(=O)OC1C(C)CCC(O)CC(=O)C1=CC=C(N)C=C1.C1=CC(NC)=CC=C1C(=O)CC(O)CCC(C)C1C(C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C(O[C@H]2[C@H]([C@@H](N)[C@H](O)[C@@H](C)O2)O)CC(O2)C(C(=O)OC)C(O)CC2(O)CC(O)CC(O)CC(O)CC(O)CC(=O)CC(O)CC(=O)O1 ALPPGSBMHVCELA-WHUUVLPESA-N 0.000 description 1
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