SG192133A1 - 7-azaindole derivatives - Google Patents

Info

Publication number

SG192133A1

SG192133A1 SG2013056726A SG2013056726A SG192133A1 SG 192133 A1 SG192133 A1 SG 192133A1 SG 2013056726 A SG2013056726 A SG 2013056726A SG 2013056726 A SG2013056726 A SG 2013056726A SG 192133 A1 SG192133 A1 SG 192133A1

Authority

SG

Singapore

Prior art keywords

pyrrolo

pyridin

denotes

methyl

pyridine

Prior art date

2011-02-01

Links

• Espacenet
• Global Dossier
• Discuss

• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical class C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 168
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 44
• -1 2,7-naphthyridin-4-yl Chemical group 0.000 claims description 98
• 150000003839 salts Chemical class 0.000 claims description 75
• 239000000203 mixture Substances 0.000 claims description 58
• 238000011282 treatment Methods 0.000 claims description 33
• 238000002360 preparation method Methods 0.000 claims description 31
• 238000006243 chemical reaction Methods 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 14
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 13
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
• 125000004434 sulfur atom Chemical group 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 11
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
• 230000001028 anti-proliverative effect Effects 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 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
• 239000000262 estrogen Substances 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 102000027483 retinoid hormone receptors Human genes 0.000 claims description 5
• 108091008679 retinoid hormone receptors Proteins 0.000 claims description 5
• 239000000849 selective androgen receptor modulator Substances 0.000 claims description 5
• 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 4
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 4
• 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 4
• 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 4
• YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• IXXKRNPDCBGDGO-UHFFFAOYSA-N 4-(1h-pyrrolo[2,3-b]pyridin-3-yl)quinolin-2-amine Chemical compound C1=CC=CC2=NC(N)=CC(C=3C4=CC=CN=C4NC=3)=C21 IXXKRNPDCBGDGO-UHFFFAOYSA-N 0.000 claims description 3
• 206010027476 Metastases Diseases 0.000 claims description 3
• 239000002671 adjuvant Substances 0.000 claims description 3
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 230000012010 growth Effects 0.000 claims description 3
• 239000004030 hiv protease inhibitor Substances 0.000 claims description 3
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 238000001959 radiotherapy Methods 0.000 claims description 3
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 3
• 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
• 239000003558 transferase inhibitor Substances 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• PAPUJGVNROYWPB-UHFFFAOYSA-N 3-(1H-indazol-3-yl)-1H-pyrrolo[2,3-b]pyridine Chemical compound C1=CC=C2C(C=3C4=CC=CN=C4NC=3)=NNC2=C1 PAPUJGVNROYWPB-UHFFFAOYSA-N 0.000 claims description 2
• AGWCRZIQRIJNAL-UHFFFAOYSA-N 3-(1h-pyrrolo[2,3-b]pyridin-3-yl)-1h-pyrrolo[2,3-c]pyridine Chemical compound C1=CC=C2C(C=3C4=CC=NC=C4NC=3)=CNC2=N1 AGWCRZIQRIJNAL-UHFFFAOYSA-N 0.000 claims description 2
• QEKJMVPBZHTKHP-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-3-(1h-pyrrolo[2,3-c]pyridin-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=NN(C)C=C1C1=CN=C(NC=C2C=3C4=CC=NC=C4NC=3)C2=C1 QEKJMVPBZHTKHP-UHFFFAOYSA-N 0.000 claims description 2
• VSJOEPNUQOKSEI-UHFFFAOYSA-N 5-(1-methylpyrrolo[2,3-b]pyridin-3-yl)isoquinoline Chemical compound C12=CC=CN=C2N(C)C=C1C1=CC=CC2=CN=CC=C12 VSJOEPNUQOKSEI-UHFFFAOYSA-N 0.000 claims description 2
• 208000030507 AIDS Diseases 0.000 claims description 2
• 125000002619 bicyclic group Chemical group 0.000 claims description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• 229920006395 saturated elastomer Polymers 0.000 claims description 2
• 229940075993 receptor modulator Drugs 0.000 claims 4
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 2
• 229940122440 HIV protease inhibitor Drugs 0.000 claims 2
• 229940123468 Transferase inhibitor Drugs 0.000 claims 2
• IIFABEVHKXGAPS-UHFFFAOYSA-N 1-(1h-pyrrolo[2,3-b]pyridin-3-yl)-2,6-naphthyridine Chemical compound N1=CC=C2C(C=3C4=CC=CN=C4NC=3)=NC=CC2=C1 IIFABEVHKXGAPS-UHFFFAOYSA-N 0.000 claims 1
• XLKDJOPOOHHZAN-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine Chemical compound C1=NC=C2NC=CC2=C1 XLKDJOPOOHHZAN-UHFFFAOYSA-N 0.000 claims 1
• GCCFYOUSCICNCD-UHFFFAOYSA-N 2h-2,7-naphthyridin-1-one Chemical compound C1=NC=C2C(O)=NC=CC2=C1 GCCFYOUSCICNCD-UHFFFAOYSA-N 0.000 claims 1
• HQYZHGKYWQRPGY-UHFFFAOYSA-N 4-(1h-pyrrolo[2,3-b]pyridin-3-yl)-1,8-naphthyridine Chemical compound C1=CC=C2C(C=3C4=CC=CN=C4NC=3)=CC=NC2=N1 HQYZHGKYWQRPGY-UHFFFAOYSA-N 0.000 claims 1
• ANHJNCWVFWGART-UHFFFAOYSA-N 5-(6-methyl-1h-pyrrolo[2,3-b]pyridin-3-yl)-2,6-naphthyridin-1-amine Chemical compound N1=CC=C2C(C=3C4=CC=C(N=C4NC=3)C)=NC=CC2=C1N ANHJNCWVFWGART-UHFFFAOYSA-N 0.000 claims 1
• BUUCNPYMIJAGKL-UHFFFAOYSA-N 8-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrido[2,3-b]pyrazine Chemical compound C1=CN=C2C(C=3C4=CC=CN=C4NC=3)=CC=NC2=N1 BUUCNPYMIJAGKL-UHFFFAOYSA-N 0.000 claims 1
• 102100028644 Tenascin-R Human genes 0.000 claims 1
• YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims 1
• 108010020387 tenascin R Proteins 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 13
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• 101000600756 Homo sapiens 3-phosphoinositide-dependent protein kinase 1 Proteins 0.000 abstract 1
• 101001117146 Homo sapiens [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial Proteins 0.000 abstract 1
• 102100024148 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial Human genes 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• 235000013350 formula milk Nutrition 0.000 description 53
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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