HRP20031069A2 - Azaindoles - Google Patents
AzaindolesInfo
- Publication number
- HRP20031069A2 HRP20031069A2 HR20031069A HRP20031069A HRP20031069A2 HR P20031069 A2 HRP20031069 A2 HR P20031069A2 HR 20031069 A HR20031069 A HR 20031069A HR P20031069 A HRP20031069 A HR P20031069A HR P20031069 A2 HRP20031069 A2 HR P20031069A2
- Authority
- HR
- Croatia
- Prior art keywords
- pyrrolo
- methyl
- indol
- pyridin
- methoxy
- Prior art date
Links
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 712
- 125000000217 alkyl group Chemical group 0.000 claims description 175
- 238000000034 method Methods 0.000 claims description 140
- -1 cyclic acetal Chemical class 0.000 claims description 121
- 125000001072 heteroaryl group Chemical group 0.000 claims description 118
- 229910052739 hydrogen Inorganic materials 0.000 claims description 109
- 239000001257 hydrogen Substances 0.000 claims description 108
- 125000003118 aryl group Chemical group 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 97
- 150000001204 N-oxides Chemical class 0.000 claims description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 81
- 239000000651 prodrug Substances 0.000 claims description 79
- 229940002612 prodrug Drugs 0.000 claims description 79
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 74
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 125000005843 halogen group Chemical group 0.000 claims description 61
- 239000012453 solvate Substances 0.000 claims description 59
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 56
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 41
- 150000002431 hydrogen Chemical group 0.000 claims description 40
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 38
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 37
- 238000002360 preparation method Methods 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 230000002378 acidificating effect Effects 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 28
- 150000004677 hydrates Chemical class 0.000 claims description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- 125000001475 halogen functional group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000001041 indolyl group Chemical group 0.000 claims description 23
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- NCODGTKJFCNVAH-UHFFFAOYSA-N 1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 NCODGTKJFCNVAH-UHFFFAOYSA-N 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- CVDGAVDNVQNYQT-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 CVDGAVDNVQNYQT-UHFFFAOYSA-N 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 230000003197 catalytic effect Effects 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 14
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 14
- RVHRALDRJAGLNN-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-6-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2N(C)C=C1C1=CC2=CC=CN=C2N1 RVHRALDRJAGLNN-UHFFFAOYSA-N 0.000 claims description 12
- 108090000461 Aurora Kinase A Proteins 0.000 claims description 12
- 102100032311 Aurora kinase A Human genes 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 230000001976 improved effect Effects 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 claims description 10
- 229910014033 C-OH Inorganic materials 0.000 claims description 10
- 229910014570 C—OH Inorganic materials 0.000 claims description 10
- 108091000080 Phosphotransferase Proteins 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 102000020233 phosphotransferase Human genes 0.000 claims description 10
- 235000019260 propionic acid Nutrition 0.000 claims description 10
- AZEKOCYKHUJNKS-UHFFFAOYSA-N 1-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxycyclobutane-1-carboxylic acid Chemical compound C=1C=C2N(C)C=C(C=3NC4=NC=CC=C4C=3)C2=CC=1OC1(C(O)=O)CCC1 AZEKOCYKHUJNKS-UHFFFAOYSA-N 0.000 claims description 9
- RPOHBQMVRIVWKP-UHFFFAOYSA-N 1-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropan-2-ol Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OCC(O)C)=CC2=C1 RPOHBQMVRIVWKP-UHFFFAOYSA-N 0.000 claims description 9
- XCLJFTFBHKDRHP-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(O)=O XCLJFTFBHKDRHP-UHFFFAOYSA-N 0.000 claims description 9
- MIJMZVTYIXYSDK-UHFFFAOYSA-N 6-(5-methoxy-1-methylindol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=N1 MIJMZVTYIXYSDK-UHFFFAOYSA-N 0.000 claims description 9
- 125000006414 CCl Chemical group ClC* 0.000 claims description 9
- 229940080818 propionamide Drugs 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- FTJGHPGHUSLQAK-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carbonitrile Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C#N FTJGHPGHUSLQAK-UHFFFAOYSA-N 0.000 claims description 8
- QSZHVPFODMPGOS-UHFFFAOYSA-N 2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=C1C(O)=O QSZHVPFODMPGOS-UHFFFAOYSA-N 0.000 claims description 8
- SWSNYMMQZWVXAI-UHFFFAOYSA-N 3-(4-chloro-1h-pyrrolo[2,3-b]pyridin-2-yl)-1-methylindole-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2N(C)C=C1C1=CC2=C(Cl)C=CN=C2N1 SWSNYMMQZWVXAI-UHFFFAOYSA-N 0.000 claims description 8
- LIZDNKRMTCXMAV-UHFFFAOYSA-N 3-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-2-yl]-1-methylindole-5-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC=NC2=C1C=C(C=1C3=CC(=CC=C3N(C)C=1)C(O)=O)N2 LIZDNKRMTCXMAV-UHFFFAOYSA-N 0.000 claims description 8
- NWCNXQNJIZEBTG-UHFFFAOYSA-N 3-[6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propanoic acid Chemical compound N1C2=NC=CN=C2C(CCC(=O)O)=C1C1=CC=C(O)C=C1 NWCNXQNJIZEBTG-UHFFFAOYSA-N 0.000 claims description 8
- NUKABDWWQOLSDM-UHFFFAOYSA-N 6-(4-tert-butylphenyl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC2=NC=CN=C2N1 NUKABDWWQOLSDM-UHFFFAOYSA-N 0.000 claims description 8
- UGHVSNVFYBZSLH-UHFFFAOYSA-N [1-[1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-5-yl]oxycyclobutyl]methanol Chemical compound C=1C=C2N(C)C=C(C=3NC4=NC=CN=C4C=3)C2=CC=1OC1(CO)CCC1 UGHVSNVFYBZSLH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 229960004063 propylene glycol Drugs 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- HVPYZVWMSSBUNJ-UHFFFAOYSA-N 2-(1-ethyl-5-methoxyindol-3-yl)-n-(1-hydroxy-2-methylpropan-2-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C12=CC(OC)=CC=C2N(CC)C=C1C1=CC2=C(C(=O)NC(C)(C)CO)C=CN=C2N1 HVPYZVWMSSBUNJ-UHFFFAOYSA-N 0.000 claims description 7
- GZRCWJUTTURNJO-UHFFFAOYSA-N 2-(5,6-dimethoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C=3C=4C=C(C(=CC=4N(C)C=3)OC)OC)=CC2=C1 GZRCWJUTTURNJO-UHFFFAOYSA-N 0.000 claims description 7
- VZLHVQTYCPRPHS-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1 VZLHVQTYCPRPHS-UHFFFAOYSA-N 0.000 claims description 7
- CIDALPHOFCAXQR-UHFFFAOYSA-N 2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carbonitrile Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=C1C#N CIDALPHOFCAXQR-UHFFFAOYSA-N 0.000 claims description 7
- CBSWBKLIQDUSCA-UHFFFAOYSA-N 3-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-2-yl]-1h-indole-5-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC=NC2=C1C=C(C=1C3=CC(=CC=C3NC=1)C(O)=O)N2 CBSWBKLIQDUSCA-UHFFFAOYSA-N 0.000 claims description 7
- BSONOAQXFAIGPB-UHFFFAOYSA-N 3-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol Chemical compound C1=CN=C2NC(C3=CN(CCCO)C4=CC=C(C=C43)OC)=CC2=N1 BSONOAQXFAIGPB-UHFFFAOYSA-N 0.000 claims description 7
- YHKXZXWIOPNPDS-UHFFFAOYSA-N 3-[[1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carbonyl]amino]propanoic acid Chemical compound C12=CC(C(=O)NCCC(O)=O)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 YHKXZXWIOPNPDS-UHFFFAOYSA-N 0.000 claims description 7
- CYGVUQDIFRECJA-UHFFFAOYSA-N 4-[2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2C=1C(C)=NOC=1C CYGVUQDIFRECJA-UHFFFAOYSA-N 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 206010003246 arthritis Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- AMECZOITPGYJEM-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(=O)NC(C)(C)CO AMECZOITPGYJEM-UHFFFAOYSA-N 0.000 claims description 7
- SAYAZSFRHPSZLZ-CYBMUJFWSA-N (2r)-3-[6-methoxy-1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropane-1,2-diol Chemical compound C1=CN=C2NC(C3=CN(C)C=4C=C(C(=CC=43)OC[C@H](O)CO)OC)=CC2=C1 SAYAZSFRHPSZLZ-CYBMUJFWSA-N 0.000 claims description 6
- KYWSGFFFDGCSES-UHFFFAOYSA-N 1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 KYWSGFFFDGCSES-UHFFFAOYSA-N 0.000 claims description 6
- QPQYJHKPANJWSN-UHFFFAOYSA-N 2-(1-ethyl-5-methoxyindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C12=CC(OC)=CC=C2N(CC)C=C1C1=CC2=C(C(O)=O)C=CN=C2N1 QPQYJHKPANJWSN-UHFFFAOYSA-N 0.000 claims description 6
- LPOOZQNTAHNETD-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-4-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2C1=CC=CC=C1 LPOOZQNTAHNETD-UHFFFAOYSA-N 0.000 claims description 6
- FKDHQBOTZUDZEJ-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-4-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2C1=CC=CN=C1 FKDHQBOTZUDZEJ-UHFFFAOYSA-N 0.000 claims description 6
- COKIRTGHADVGEP-UHFFFAOYSA-N 2-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropan-1-ol Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC(CO)C)=CC2=C1 COKIRTGHADVGEP-UHFFFAOYSA-N 0.000 claims description 6
- FPFNTCBEXLWOSS-UHFFFAOYSA-N 2-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropanoic acid Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC(C)C(O)=O)=CC2=C1 FPFNTCBEXLWOSS-UHFFFAOYSA-N 0.000 claims description 6
- MCTZIYPXXHBZEW-UHFFFAOYSA-N 2-[1-methyl-5-(2-methyltetrazol-5-yl)indol-3-yl]-1h-pyrrolo[2,3-b]pyridine Chemical compound CN1N=NC(C=2C=C3C(C=4NC5=NC=CC=C5C=4)=CN(C)C3=CC=2)=N1 MCTZIYPXXHBZEW-UHFFFAOYSA-N 0.000 claims description 6
- HIWPOKJDACYAFJ-UHFFFAOYSA-N 3-(4-methoxy-1h-pyrrolo[2,3-b]pyridin-2-yl)-1-methylindole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(C=3NC=4N=CC=C(C=4C=3)OC)=CN(C)C2=C1 HIWPOKJDACYAFJ-UHFFFAOYSA-N 0.000 claims description 6
- MUQFTYHVZUPXES-UHFFFAOYSA-N 3-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxypropane-1,2-diol Chemical compound C12=CC(OCC(O)CO)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 MUQFTYHVZUPXES-UHFFFAOYSA-N 0.000 claims description 6
- BZGCYSXNPHENAB-UHFFFAOYSA-N 3-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]propanoic acid Chemical compound C12=CC(CCC(O)=O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 BZGCYSXNPHENAB-UHFFFAOYSA-N 0.000 claims description 6
- VEKQEFMQDFQZSJ-UHFFFAOYSA-N 3-[3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol Chemical compound C12=CC=CC=C2N(CCCO)C=C1C1=CC2=NC=CN=C2N1 VEKQEFMQDFQZSJ-UHFFFAOYSA-N 0.000 claims description 6
- HQXGRCCXAAELRO-UHFFFAOYSA-N 3-[6-(4-tert-butylphenyl)-5h-pyrrolo[2,3-b]pyrazin-7-yl]propan-1-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=C(CCCN)C2=NC=CN=C2N1 HQXGRCCXAAELRO-UHFFFAOYSA-N 0.000 claims description 6
- RDGODMUTJJJLBX-UHFFFAOYSA-N 3-[6-(4-tert-butylphenyl)-5h-pyrrolo[2,3-b]pyrazin-7-yl]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=C(CCC(O)=O)C2=NC=CN=C2N1 RDGODMUTJJJLBX-UHFFFAOYSA-N 0.000 claims description 6
- JJTVNLBIXOXIQR-UHFFFAOYSA-N 4-[2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C12=CC(OC)=CC=C2NC=C1C(NC1=NC=C2)=CC1=C2C=1C(C)=NOC=1C JJTVNLBIXOXIQR-UHFFFAOYSA-N 0.000 claims description 6
- LMHHYPOKWRDJTP-UHFFFAOYSA-N 4-chloro-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1Cl LMHHYPOKWRDJTP-UHFFFAOYSA-N 0.000 claims description 6
- AZZIWMRQTCNYEQ-UHFFFAOYSA-N 4-chloro-2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=C1Cl AZZIWMRQTCNYEQ-UHFFFAOYSA-N 0.000 claims description 6
- JFFMPLDYSOUBPW-UHFFFAOYSA-N 4-methoxy-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1OC JFFMPLDYSOUBPW-UHFFFAOYSA-N 0.000 claims description 6
- QFSGJFOPYOPYRB-UHFFFAOYSA-N 4-methoxy-2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=C1OC QFSGJFOPYOPYRB-UHFFFAOYSA-N 0.000 claims description 6
- OPIPFYKXYNLMGL-UHFFFAOYSA-N 6-(1-methyl-4-phenylpyrrol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C=1N(C)C=C(C=2NC3=NC=CN=C3C=2)C=1C1=CC=CC=C1 OPIPFYKXYNLMGL-UHFFFAOYSA-N 0.000 claims description 6
- WGWNCAKNPSBPPM-UHFFFAOYSA-N 6-(1-methylindol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C12=CC=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 WGWNCAKNPSBPPM-UHFFFAOYSA-N 0.000 claims description 6
- IKISMFQWQNPZGJ-UHFFFAOYSA-N 6-(1h-indol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC(C=3C4=CC=CC=C4NC=3)=CC2=N1 IKISMFQWQNPZGJ-UHFFFAOYSA-N 0.000 claims description 6
- DYFHPNQRLTZBCB-UHFFFAOYSA-N 6-(4-methylsulfanylphenyl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CC(SC)=CC=C1C1=CC2=NC=CN=C2N1 DYFHPNQRLTZBCB-UHFFFAOYSA-N 0.000 claims description 6
- OUDTUFDECCLCLN-UHFFFAOYSA-N 6-(4-tert-butylphenyl)-7-methyl-5h-pyrrolo[2,3-b]pyrazine Chemical compound N1C2=NC=CN=C2C(C)=C1C1=CC=C(C(C)(C)C)C=C1 OUDTUFDECCLCLN-UHFFFAOYSA-N 0.000 claims description 6
- BOAWWCKJPHLVFL-UHFFFAOYSA-N 6-(5-methoxy-1h-indol-3-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC(C3=CNC4=CC=C(C=C43)OC)=CC2=N1 BOAWWCKJPHLVFL-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
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- 229960003104 ornithine Drugs 0.000 description 1
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- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 108091005981 phosphorylated proteins Proteins 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
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- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 230000010118 platelet activation Effects 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
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- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
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- WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical compound C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 description 1
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- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QSGLXPBXGHJDEK-UHFFFAOYSA-N tert-butyl 2-(5-methoxy-1-methylindol-3-yl)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine-4-carboxylate Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C1=CC2=C(C(=O)OC(C)(C)C)C=CN=C2N1S(=O)(=O)C1=CC=C(C)C=C1 QSGLXPBXGHJDEK-UHFFFAOYSA-N 0.000 description 1
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- FGFJNEIWWKBCFK-UHFFFAOYSA-N tert-butyl 2-[5,6-dimethoxy-3-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]indol-1-yl]acetate Chemical compound C=1N(CC(=O)OC(C)(C)C)C=2C=C(OC)C(OC)=CC=2C=1C1=CC2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C)C=C1 FGFJNEIWWKBCFK-UHFFFAOYSA-N 0.000 description 1
- PMHVRQIEKSJLPW-UHFFFAOYSA-N tert-butyl n-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]carbamate Chemical compound C12=CC(NC(=O)OC(C)(C)C)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 PMHVRQIEKSJLPW-UHFFFAOYSA-N 0.000 description 1
- GTIVKALLFZZJFA-UHFFFAOYSA-N tert-butyl-[2-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethoxy]-dimethylsilane Chemical compound C1=CN=C2NC(C3=CN(CCO[Si](C)(C)C(C)(C)C)C4=CC=C(C=C43)OC)=CC2=N1 GTIVKALLFZZJFA-UHFFFAOYSA-N 0.000 description 1
- RZMPCCIQPRHXCC-UHFFFAOYSA-N tert-butyl-[3-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propoxy]-dimethylsilane Chemical compound C1=CN=C2NC(C3=CN(CCCO[Si](C)(C)C(C)(C)C)C4=CC=C(C=C43)OC)=CC2=N1 RZMPCCIQPRHXCC-UHFFFAOYSA-N 0.000 description 1
- DEVZMRRLUDQEHL-UHFFFAOYSA-N tert-butyl-dimethyl-[2-[3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethoxy]silane Chemical compound C12=CC=CC=C2N(CCO[Si](C)(C)C(C)(C)C)C=C1C1=CC2=NC=CN=C2N1 DEVZMRRLUDQEHL-UHFFFAOYSA-N 0.000 description 1
- IJAGVSQDJDQRIM-UHFFFAOYSA-N tert-butyl-dimethyl-[3-[3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propoxy]silane Chemical compound C12=CC=CC=C2N(CCCO[Si](C)(C)C(C)(C)C)C=C1C1=CC2=NC=CN=C2N1 IJAGVSQDJDQRIM-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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- 230000000699 topical effect Effects 0.000 description 1
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- 238000000844 transformation Methods 0.000 description 1
- 108091008578 transmembrane receptors Proteins 0.000 description 1
- 102000027257 transmembrane receptors Human genes 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- JKVRTUCVPZTEQZ-UHFFFAOYSA-N tributyltin azide Chemical compound CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-] JKVRTUCVPZTEQZ-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- PXSQLMPCRDHKPE-UHFFFAOYSA-N trimethyl-[5-[1-methyl-3-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]indol-5-yl]tetrazol-1-yl]stannane Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC=C2C=C1C1=CN(C)C2=CC=C(C=3N(N=NN=3)[Sn](C)(C)C)C=C12 PXSQLMPCRDHKPE-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0115109.1A GB0115109D0 (en) | 2001-06-21 | 2001-06-21 | Chemical compounds |
US30025701P | 2001-06-22 | 2001-06-22 | |
PCT/GB2002/002799 WO2003000688A1 (en) | 2001-06-21 | 2002-06-20 | Azaindoles |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20031069A2 true HRP20031069A2 (en) | 2004-04-30 |
Family
ID=9917016
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20031069A HRP20031069A2 (en) | 2001-06-21 | 2003-12-19 | Azaindoles |
Country Status (37)
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2004
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