CA2234609C - 2-amino-6-anilino-purine derivatives and processes for their preparation - Google Patents

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Publication number

CA2234609C

CA2234609C CA002234609A CA2234609A CA2234609C CA 2234609 C CA2234609 C CA 2234609C CA 002234609 A CA002234609 A CA 002234609A CA 2234609 A CA2234609 A CA 2234609A CA 2234609 C CA2234609 C CA 2234609C

Authority

CA

Canada

Prior art keywords

amino

ethyl

phenyl

purine

chloro

Prior art date

1995-11-01

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

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• AWRCGEJILTVONY-UHFFFAOYSA-N 6-n-phenyl-7h-purine-2,6-diamine Chemical class C=12NC=NC2=NC(N)=NC=1NC1=CC=CC=C1 AWRCGEJILTVONY-UHFFFAOYSA-N 0.000 title claims abstract description 7
• 238000000034 method Methods 0.000 title claims description 32
• 230000008569 process Effects 0.000 title claims description 23
• 238000002360 preparation method Methods 0.000 title claims description 21
• -1 piperazin-1-yl-carbonyl Chemical group 0.000 claims abstract description 751
• 150000001875 compounds Chemical class 0.000 claims abstract description 119
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 99
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 96
• 150000003839 salts Chemical class 0.000 claims abstract description 67
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 65
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 53
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 52
• 239000001257 hydrogen Substances 0.000 claims abstract description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 45
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 31
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 30
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 26
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 17
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
• 239000001301 oxygen Substances 0.000 claims abstract description 17
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 125000002252 acyl group Chemical group 0.000 claims abstract description 15
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
• 125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 12
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 12
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 12
• 239000011593 sulfur Substances 0.000 claims abstract description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 11
• 125000004423 acyloxy group Chemical group 0.000 claims abstract description 7
• 150000003254 radicals Chemical class 0.000 claims description 53
• 125000001424 substituent group Chemical group 0.000 claims description 33
• 125000006239 protecting group Chemical group 0.000 claims description 32
• 150000002367 halogens Chemical group 0.000 claims description 29
• 125000000524 functional group Chemical group 0.000 claims description 26
• 125000003277 amino group Chemical group 0.000 claims description 21
• 239000000460 chlorine Substances 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 19
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
• 241001465754 Metazoa Species 0.000 claims description 15
• 150000005840 aryl radicals Chemical class 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
• 150000001412 amines Chemical class 0.000 claims description 13
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 11
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 10
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 7
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
• JNPVNIHVQDAPGV-UHFFFAOYSA-N 2-[[9-ethyl-6-(4-fluoroanilino)purin-2-yl]amino]ethanol Chemical compound N1=C(NCCO)N=C2N(CC)C=NC2=C1NC1=CC=C(F)C=C1 JNPVNIHVQDAPGV-UHFFFAOYSA-N 0.000 claims description 4
• LJNGHQATEXHFTP-UHFFFAOYSA-N 3-[[9-ethyl-6-[3-(trifluoromethyl)anilino]purin-2-yl]amino]propan-1-ol Chemical compound N1=C(NCCCO)N=C2N(CC)C=NC2=C1NC1=CC=CC(C(F)(F)F)=C1 LJNGHQATEXHFTP-UHFFFAOYSA-N 0.000 claims description 4
• LLKNJDANISFMJC-UHFFFAOYSA-N benzyl n-[4-[[9-ethyl-2-(2-hydroxyethylamino)purin-6-yl]amino]phenyl]carbamate Chemical compound N1=C(NCCO)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1NC(=O)OCC1=CC=CC=C1 LLKNJDANISFMJC-UHFFFAOYSA-N 0.000 claims description 4
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• CQYKZYZOSSGEEV-CYBMUJFWSA-N (2r)-1-[6-(3-chloroanilino)-9-ethylpurin-2-yl]pyrrolidine-2-carboxamide Chemical compound N1=C(N2[C@H](CCC2)C(N)=O)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 CQYKZYZOSSGEEV-CYBMUJFWSA-N 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical group CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 3
• DIEYJCDILBBDAH-UHFFFAOYSA-N 2-n-(2-aminoethyl)-9-ethyl-6-n-[3-(trifluoromethyl)phenyl]purine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=CC(C(F)(F)F)=C1 DIEYJCDILBBDAH-UHFFFAOYSA-N 0.000 claims description 3
• UTBSBSOBZHXMHI-HUUCEWRRSA-N 2-n-[(1r,2r)-2-aminocyclohexyl]-6-n-(3-chlorophenyl)-9-ethylpurine-2,6-diamine Chemical compound N1=C(N[C@H]2[C@@H](CCCC2)N)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 UTBSBSOBZHXMHI-HUUCEWRRSA-N 0.000 claims description 3
• UTBSBSOBZHXMHI-LSDHHAIUSA-N 2-n-[(1r,2s)-2-aminocyclohexyl]-6-n-(3-chlorophenyl)-9-ethylpurine-2,6-diamine Chemical compound N1=C(N[C@H]2[C@H](CCCC2)N)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 UTBSBSOBZHXMHI-LSDHHAIUSA-N 0.000 claims description 3
• ZJIUJMWBIVKNFS-UHFFFAOYSA-N 2-n-[2-(2-aminoethylamino)ethyl]-6-n-(3-chlorophenyl)-9-ethylpurine-2,6-diamine Chemical compound N1=C(NCCNCCN)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 ZJIUJMWBIVKNFS-UHFFFAOYSA-N 0.000 claims description 3
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 3
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
• VTBDWFOWRXMHTO-UHFFFAOYSA-N ethyl 3-[(2-chloro-7h-purin-6-yl)amino]-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2C=3NC=NC=3N=C(Cl)N=2)=C1C VTBDWFOWRXMHTO-UHFFFAOYSA-N 0.000 claims description 3
• PTSASSOBZROJTE-UHFFFAOYSA-N ethyl 3-[(2-chloro-9-ethylpurin-6-yl)amino]-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2C=3N=CN(CC)C=3N=C(Cl)N=2)=C1C PTSASSOBZROJTE-UHFFFAOYSA-N 0.000 claims description 3
• LCZSHGMYRQOQDU-SNVBAGLBSA-N (2r)-1-[[6-(3-chloroanilino)-9-ethylpurin-2-yl]amino]propan-2-ol Chemical compound N1=C(NC[C@@H](C)O)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 LCZSHGMYRQOQDU-SNVBAGLBSA-N 0.000 claims description 2
• ZBNSIWHRSJGXPO-GFCCVEGCSA-N (2r)-2-[[6-(4-aminoanilino)-9-ethylpurin-2-yl]amino]butan-1-ol Chemical compound C=12N=CN(CC)C2=NC(N[C@@H](CO)CC)=NC=1NC1=CC=C(N)C=C1 ZBNSIWHRSJGXPO-GFCCVEGCSA-N 0.000 claims description 2
• HSUHYEDVZHVJCJ-GFCCVEGCSA-N (2r)-2-[[6-[3,5-bis(trifluoromethyl)anilino]-9-ethylpurin-2-yl]amino]butan-1-ol Chemical compound C=12N=CN(CC)C2=NC(N[C@@H](CO)CC)=NC=1NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HSUHYEDVZHVJCJ-GFCCVEGCSA-N 0.000 claims description 2
• LUOFSIVXWNTHHG-SNVBAGLBSA-N (2r)-2-[[6-[4-chloro-3-(trifluoromethyl)anilino]-9-ethylpurin-2-yl]amino]butan-1-ol Chemical compound C=12N=CN(CC)C2=NC(N[C@@H](CO)CC)=NC=1NC1=CC=C(Cl)C(C(F)(F)F)=C1 LUOFSIVXWNTHHG-SNVBAGLBSA-N 0.000 claims description 2
• AMYQMTWPMGMMTQ-GFCCVEGCSA-N (2r)-2-[[9-ethyl-6-(3-fluoroanilino)purin-2-yl]amino]butan-1-ol Chemical compound C=12N=CN(CC)C2=NC(N[C@@H](CO)CC)=NC=1NC1=CC=CC(F)=C1 AMYQMTWPMGMMTQ-GFCCVEGCSA-N 0.000 claims description 2
• GWFQWQACPHMODW-GFCCVEGCSA-N (2r)-2-[[9-ethyl-6-(4-fluoroanilino)purin-2-yl]amino]butan-1-ol Chemical compound C=12N=CN(CC)C2=NC(N[C@@H](CO)CC)=NC=1NC1=CC=C(F)C=C1 GWFQWQACPHMODW-GFCCVEGCSA-N 0.000 claims description 2
• YDYNWPUQOWJFTO-GFCCVEGCSA-N (2r)-2-[[9-ethyl-6-[3-(trifluoromethyl)anilino]purin-2-yl]amino]butan-1-ol Chemical compound C=12N=CN(CC)C2=NC(N[C@@H](CO)CC)=NC=1NC1=CC=CC(C(F)(F)F)=C1 YDYNWPUQOWJFTO-GFCCVEGCSA-N 0.000 claims description 2
• LFDBCEZGMORVGP-GFCCVEGCSA-N (2r)-2-[[9-ethyl-6-[4-(trifluoromethyl)anilino]purin-2-yl]amino]butan-1-ol Chemical compound C=12N=CN(CC)C2=NC(N[C@@H](CO)CC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 LFDBCEZGMORVGP-GFCCVEGCSA-N 0.000 claims description 2
• LCZSHGMYRQOQDU-JTQLQIEISA-N (2s)-1-[[6-(3-chloroanilino)-9-ethylpurin-2-yl]amino]propan-2-ol Chemical compound N1=C(NC[C@H](C)O)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 LCZSHGMYRQOQDU-JTQLQIEISA-N 0.000 claims description 2
• IEYKKOSGFKCDCK-UHFFFAOYSA-N 1-[[6-(3-chloroanilino)-9-ethylpurin-2-yl]-methylamino]cyclohexan-1-ol Chemical compound N1=C(N(C)C2(O)CCCCC2)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 IEYKKOSGFKCDCK-UHFFFAOYSA-N 0.000 claims description 2
• VDCPEHPHPJICCB-CQSZACIVSA-N 2-[(2r)-2-(aminomethyl)pyrrolidin-1-yl]-n-(3-chlorophenyl)-9-ethylpurin-6-amine Chemical compound N1=C(N2[C@H](CCC2)CN)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 VDCPEHPHPJICCB-CQSZACIVSA-N 0.000 claims description 2
• VDCPEHPHPJICCB-AWEZNQCLSA-N 2-[(2s)-2-(aminomethyl)pyrrolidin-1-yl]-n-(3-chlorophenyl)-9-ethylpurin-6-amine Chemical compound N1=C(N2[C@@H](CCC2)CN)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 VDCPEHPHPJICCB-AWEZNQCLSA-N 0.000 claims description 2
• FZQOIYJBNKTLLI-UHFFFAOYSA-N 2-[2-[[6-(3-chloroanilino)-9-ethylpurin-2-yl]amino]ethyl]guanidine Chemical compound N1=C(NCCNC(N)=N)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 FZQOIYJBNKTLLI-UHFFFAOYSA-N 0.000 claims description 2
• QGWQYKMWGDJLPU-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperazin-1-yl]-n-(3-chlorophenyl)-9-ethylpurin-6-amine Chemical compound N1=C(N2CCN(CCN)CC2)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 QGWQYKMWGDJLPU-UHFFFAOYSA-N 0.000 claims description 2
• BJGHBTLRFUFYBS-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperidin-1-yl]-n-(3-chlorophenyl)-9-ethylpurin-6-amine Chemical compound N1=C(N2CCC(CCN)CC2)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 BJGHBTLRFUFYBS-UHFFFAOYSA-N 0.000 claims description 2
• PSCCDYUWFQSBBR-UHFFFAOYSA-N 2-[[6-(3-fluoroanilino)-9-propan-2-ylpurin-2-yl]amino]ethanol Chemical compound N1=C(NCCO)N=C2N(C(C)C)C=NC2=C1NC1=CC=CC(F)=C1 PSCCDYUWFQSBBR-UHFFFAOYSA-N 0.000 claims description 2
• GQDAOWXYXYPSEB-UHFFFAOYSA-N 2-[[6-[3,5-bis(trifluoromethyl)anilino]-9-ethylpurin-2-yl]amino]ethanol Chemical compound N1=C(NCCO)N=C2N(CC)C=NC2=C1NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GQDAOWXYXYPSEB-UHFFFAOYSA-N 0.000 claims description 2
• AXPFCBGHNKFCGY-UHFFFAOYSA-N 2-[[6-[4-chloro-3-(trifluoromethyl)anilino]-9-ethylpurin-2-yl]amino]ethanol Chemical compound N1=C(NCCO)N=C2N(CC)C=NC2=C1NC1=CC=C(Cl)C(C(F)(F)F)=C1 AXPFCBGHNKFCGY-UHFFFAOYSA-N 0.000 claims description 2
• IRGRXPXBLYTVKS-UHFFFAOYSA-N 2-[[9-ethyl-2-(2-hydroxyethylamino)purin-6-yl]amino]ethanol Chemical compound N1=C(NCCO)N=C2N(CC)C=NC2=C1NCCO IRGRXPXBLYTVKS-UHFFFAOYSA-N 0.000 claims description 2
• RYMVLPRCPUDOKH-UHFFFAOYSA-N 2-[[9-ethyl-6-(3-fluoroanilino)purin-2-yl]amino]ethanol Chemical compound N1=C(NCCO)N=C2N(CC)C=NC2=C1NC1=CC=CC(F)=C1 RYMVLPRCPUDOKH-UHFFFAOYSA-N 0.000 claims description 2
• PLYHQMXPVPPNDY-UHFFFAOYSA-N 2-[[9-ethyl-6-[4-(trifluoromethyl)anilino]purin-2-yl]amino]ethanol Chemical compound N1=C(NCCO)N=C2N(CC)C=NC2=C1NC1=CC=C(C(F)(F)F)C=C1 PLYHQMXPVPPNDY-UHFFFAOYSA-N 0.000 claims description 2
• QYHLOXVYPZVXLV-UHFFFAOYSA-N 2-n-(1-adamantyl)-6-n-(3-chlorophenyl)-9-ethylpurine-2,6-diamine Chemical compound N1=C(NC23CC4CC(CC(C4)C2)C3)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 QYHLOXVYPZVXLV-UHFFFAOYSA-N 0.000 claims description 2
• MANPEIPVNZSOJW-UHFFFAOYSA-N 2-n-(2-aminoethyl)-6-n-(3-chlorophenyl)-9-ethylpurine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 MANPEIPVNZSOJW-UHFFFAOYSA-N 0.000 claims description 2
• VSEFWWDZTWPHSY-UHFFFAOYSA-N 2-n-(2-aminoethyl)-6-n-(3-chlorophenyl)-9-propan-2-ylpurine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(C(C)C)C=NC2=C1NC1=CC=CC(Cl)=C1 VSEFWWDZTWPHSY-UHFFFAOYSA-N 0.000 claims description 2
• GNJKZKUJSYNKJT-UHFFFAOYSA-N 2-n-(2-aminoethyl)-6-n-(3-fluorophenyl)-9-propan-2-ylpurine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(C(C)C)C=NC2=C1NC1=CC=CC(F)=C1 GNJKZKUJSYNKJT-UHFFFAOYSA-N 0.000 claims description 2
• CAHHCKPKIYTNPC-UHFFFAOYSA-N 2-n-(2-aminoethyl)-6-n-(3-methoxyphenyl)-9-propan-2-ylpurine-2,6-diamine Chemical compound COC1=CC=CC(NC=2C=3N=CN(C=3N=C(NCCN)N=2)C(C)C)=C1 CAHHCKPKIYTNPC-UHFFFAOYSA-N 0.000 claims description 2
• PWJIJHKNCPUMRZ-UHFFFAOYSA-N 2-n-(2-aminoethyl)-6-n-(4-aminophenyl)-9-ethylpurine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=C(N)C=C1 PWJIJHKNCPUMRZ-UHFFFAOYSA-N 0.000 claims description 2
• XEMOIXGIGBBIFS-UHFFFAOYSA-N 2-n-(2-aminoethyl)-6-n-(4-fluorophenyl)-9-propan-2-ylpurine-2,6-diamine;hydrochloride Chemical compound Cl.N1=C(NCCN)N=C2N(C(C)C)C=NC2=C1NC1=CC=C(F)C=C1 XEMOIXGIGBBIFS-UHFFFAOYSA-N 0.000 claims description 2
• JKZQHFFHKPVFPD-UHFFFAOYSA-N 2-n-(2-aminoethyl)-6-n-[3,5-bis(trifluoromethyl)phenyl]-9-ethylpurine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JKZQHFFHKPVFPD-UHFFFAOYSA-N 0.000 claims description 2
• YSTPGBRGMATTGI-UHFFFAOYSA-N 2-n-(2-aminoethyl)-6-n-[4-chloro-3-(trifluoromethyl)phenyl]-9-ethylpurine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=C(Cl)C(C(F)(F)F)=C1 YSTPGBRGMATTGI-UHFFFAOYSA-N 0.000 claims description 2
• WADPIXLSLDNKJV-UHFFFAOYSA-N 2-n-(2-aminoethyl)-9-ethyl-6-n-(3-fluorophenyl)purine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=CC(F)=C1 WADPIXLSLDNKJV-UHFFFAOYSA-N 0.000 claims description 2
• ILROIODVZDBFGX-UHFFFAOYSA-N 2-n-(2-aminoethyl)-9-ethyl-6-n-(3-fluorophenyl)purine-2,6-diamine;hydrochloride Chemical compound Cl.N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=CC(F)=C1 ILROIODVZDBFGX-UHFFFAOYSA-N 0.000 claims description 2
• HGYWOTOKOXQKSV-UHFFFAOYSA-N 2-n-(2-aminoethyl)-9-ethyl-6-n-(3-methoxyphenyl)purine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=CC(OC)=C1 HGYWOTOKOXQKSV-UHFFFAOYSA-N 0.000 claims description 2
• UWAPZEZKRLPWNK-UHFFFAOYSA-N 2-n-(2-aminoethyl)-9-ethyl-6-n-(4-fluorophenyl)purine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=C(F)C=C1 UWAPZEZKRLPWNK-UHFFFAOYSA-N 0.000 claims description 2
• JVQVEZLPGPPPNL-UHFFFAOYSA-N 2-n-(2-aminoethyl)-9-ethyl-6-n-[4-(trifluoromethyl)phenyl]purine-2,6-diamine Chemical compound N1=C(NCCN)N=C2N(CC)C=NC2=C1NC1=CC=C(C(F)(F)F)C=C1 JVQVEZLPGPPPNL-UHFFFAOYSA-N 0.000 claims description 2
• YCAODQVRNHYHTP-UHFFFAOYSA-N 2-n-(2-aminophenyl)-6-n-(3-chlorophenyl)-9-ethylpurine-2,6-diamine Chemical compound N1=C(NC=2C(=CC=CC=2)N)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 YCAODQVRNHYHTP-UHFFFAOYSA-N 0.000 claims description 2
• UROUSFPGLFJVLC-UHFFFAOYSA-N 2-n-(3-aminophenyl)-6-n-(3-chlorophenyl)-9-ethylpurine-2,6-diamine Chemical compound N1=C(NC=2C=C(N)C=CC=2)N=C2N(CC)C=NC2=C1NC1=CC=CC(Cl)=C1 UROUSFPGLFJVLC-UHFFFAOYSA-N 0.000 claims description 2
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