NZ530824A - 4-amino-6-phenyl-pyrrolo[2,3-d]pyrimidine derivatives - Google Patents

Info

Publication number

NZ530824A

NZ530824A NZ530824A NZ53082402A NZ530824A NZ 530824 A NZ530824 A NZ 530824A NZ 530824 A NZ530824 A NZ 530824A NZ 53082402 A NZ53082402 A NZ 53082402A NZ 530824 A NZ530824 A NZ 530824A

Authority

NZ

New Zealand

Prior art keywords

phenyl

pyrrolo

amine

ylmethyl

pyrimidin

Prior art date

2001-08-07

Links

• Espacenet
• Global Dossier
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• JSLCFLYSDVRTNX-UHFFFAOYSA-N 6-phenyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C=1C2=C(N)N=CNC2=NC=1C1=CC=CC=C1 JSLCFLYSDVRTNX-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 300
• 150000003839 salts Chemical class 0.000 claims abstract description 71
• 238000000034 method Methods 0.000 claims abstract description 70
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 37
• 239000001257 hydrogen Substances 0.000 claims abstract description 35
• 230000008569 process Effects 0.000 claims abstract description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 30
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
• 239000001301 oxygen Substances 0.000 claims abstract description 23
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
• 239000011593 sulfur Substances 0.000 claims abstract description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
• 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 162
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 98
• -1 tetrahydro-pyran-4-ylamino Chemical group 0.000 claims description 85
• 239000000203 mixture Substances 0.000 claims description 70
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 42
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• 238000011282 treatment Methods 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 238000002360 preparation method Methods 0.000 claims description 19
• 150000002367 halogens Chemical group 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 239000007858 starting material Substances 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
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• 125000002757 morpholinyl group Chemical group 0.000 claims description 12
• 125000005936 piperidyl group Chemical group 0.000 claims description 12
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 125000006239 protecting group Chemical group 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000005605 benzo group Chemical group 0.000 claims description 7
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• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000000524 functional group Chemical group 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
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• 239000003638 chemical reducing agent Substances 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• AORUSTUPGHKJIB-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-[(6-methoxypyridin-3-yl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC=C1CNC1=NC=NC2=C1C=C(C=1C=CC(CN(C)C)=CC=1)N2 AORUSTUPGHKJIB-UHFFFAOYSA-N 0.000 claims description 2
• 229910006715 Li—O Inorganic materials 0.000 claims description 2
• 239000000460 chlorine Substances 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
• IMZVRJHLNIWPNE-UHFFFAOYSA-N 6-[4-(diethylaminomethyl)phenyl]-n-(4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 IMZVRJHLNIWPNE-UHFFFAOYSA-N 0.000 claims 1
• CHADASGQTPDJDR-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-[(2-methoxypyridin-4-yl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC(CNC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN(C)C)=CC=2)=C1 CHADASGQTPDJDR-UHFFFAOYSA-N 0.000 claims 1
• 101100383992 Arabidopsis thaliana CLC-C gene Proteins 0.000 claims 1
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• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
• JSPLIDXVBSWCRT-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C5OCOC5=CC=4)=C3C=2)C=C1 JSPLIDXVBSWCRT-UHFFFAOYSA-N 0.000 claims 1
• QNTMOGBXCJRMMV-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[3-(pyrrolidin-1-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=C(CN3CCCC3)C=CC=1)N2 QNTMOGBXCJRMMV-UHFFFAOYSA-N 0.000 claims 1
• UZVDJBUBADEWMP-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-(diethylaminomethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(F)C(Cl)=C1 UZVDJBUBADEWMP-UHFFFAOYSA-N 0.000 claims 1
• UPRIQUXRYGPJPL-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)-6-[4-(pyrrolidin-1-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CCCC1 UPRIQUXRYGPJPL-UHFFFAOYSA-N 0.000 claims 1
• GVVZLZCGXVRPOC-UHFFFAOYSA-N n-[(3-methylphenyl)methyl]-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC=4C=C(C)C=CC=4)=C3C=2)C=C1 GVVZLZCGXVRPOC-UHFFFAOYSA-N 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 abstract description 4
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• 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
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• 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
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