KR20140014158A - 7-아자인돌 유도체 - Google Patents

Info

Publication number

KR20140014158A

KR20140014158A KR1020137022887A KR20137022887A KR20140014158A KR 20140014158 A KR20140014158 A KR 20140014158A KR 1020137022887 A KR1020137022887 A KR 1020137022887A KR 20137022887 A KR20137022887 A KR 20137022887A KR 20140014158 A KR20140014158 A KR 20140014158A

Authority

KR

South Korea

Prior art keywords

atoms

pyrrolo

compound

pyridin

stereoisomers

Prior art date

2011-02-01

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.)

Withdrawn

Links

• Espacenet
• Global Dossier
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• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical class C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 161
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 40
• 238000011282 treatment Methods 0.000 claims abstract description 32
• -1 2,7-naphthyridin-4-yl Chemical group 0.000 claims description 125
• 150000003839 salts Chemical class 0.000 claims description 73
• 239000000203 mixture Substances 0.000 claims description 58
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
• 125000004434 sulfur atom Chemical group 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 230000001028 anti-proliverative effect Effects 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 230000002062 proliferating effect Effects 0.000 claims description 6
• 230000004614 tumor growth Effects 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 229940127089 cytotoxic agent Drugs 0.000 claims description 5
• 239000002254 cytotoxic agent Substances 0.000 claims description 5
• 231100000599 cytotoxic agent Toxicity 0.000 claims description 5
• 239000002834 estrogen receptor modulator Substances 0.000 claims description 5
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• 239000000849 selective androgen receptor modulator Substances 0.000 claims description 5
• 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 239000004030 hiv protease inhibitor Substances 0.000 claims description 3
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• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
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• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
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• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
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• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
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• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims description 2
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• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
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• VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical group O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims 2
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• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 11
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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