DE60112960T2 - Kondensierte pyridoindolderivate - Google Patents
Kondensierte pyridoindolderivate Download PDFInfo
- Publication number
- DE60112960T2 DE60112960T2 DE60112960T DE60112960T DE60112960T2 DE 60112960 T2 DE60112960 T2 DE 60112960T2 DE 60112960 T DE60112960 T DE 60112960T DE 60112960 T DE60112960 T DE 60112960T DE 60112960 T2 DE60112960 T2 DE 60112960T2
- Authority
- DE
- Germany
- Prior art keywords
- indolizino
- dihydro
- indole
- alkyl
- group
- Prior art date
- 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 - Lifetime
Links
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 239000003814 drug Substances 0.000 claims abstract description 8
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- -1 nitro, amino Chemical group 0.000 claims description 31
- 229910052757 nitrogen Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000011593 sulfur Chemical group 0.000 claims description 15
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims description 14
- 201000001881 impotence Diseases 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 13
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 10
- 230000037007 arousal Effects 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000001225 therapeutic effect Effects 0.000 claims description 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 150000004677 hydrates Chemical class 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 238000009109 curative therapy Methods 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 4
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
- 208000033626 Renal failure acute Diseases 0.000 claims description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 208000005485 Thrombocytosis Diseases 0.000 claims description 4
- 201000011040 acute kidney failure Diseases 0.000 claims description 4
- 208000012998 acute renal failure Diseases 0.000 claims description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 210000004204 blood vessel Anatomy 0.000 claims description 4
- 206010006451 bronchitis Diseases 0.000 claims description 4
- 208000023819 chronic asthma Diseases 0.000 claims description 4
- 208000020832 chronic kidney disease Diseases 0.000 claims description 4
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
- 230000036262 stenosis Effects 0.000 claims description 4
- 208000037804 stenosis Diseases 0.000 claims description 4
- 208000019553 vascular disease Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 3
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 3
- 201000009961 allergic asthma Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 230000008901 benefit Effects 0.000 claims description 3
- 238000007889 carotid angioplasty Methods 0.000 claims description 3
- 238000007887 coronary angioplasty Methods 0.000 claims description 3
- 230000008991 intestinal motility Effects 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 208000011906 peptic ulcer disease Diseases 0.000 claims description 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000003247 decreasing effect Effects 0.000 claims description 2
- 230000035699 permeability Effects 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 206010002388 Angina unstable Diseases 0.000 claims 2
- 206010059245 Angiopathy Diseases 0.000 claims 2
- 201000001068 Prinzmetal angina Diseases 0.000 claims 2
- 208000007718 Stable Angina Diseases 0.000 claims 2
- 208000007814 Unstable Angina Diseases 0.000 claims 2
- UTWGRMYWDUMKNY-UHFFFAOYSA-N indole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)C=CC2=C1 UTWGRMYWDUMKNY-UHFFFAOYSA-N 0.000 claims 2
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 2
- 201000005857 malignant hypertension Diseases 0.000 claims 2
- 208000028591 pheochromocytoma Diseases 0.000 claims 2
- YGGDCRUPBLYTPM-UHFFFAOYSA-N 1-[10-(1,3-benzodioxol-5-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carbonyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)C1=C2CC(C3=CC=CC=C3N3)=C3C(C=3C=C4OCOC4=CC=3)N2C=C1 YGGDCRUPBLYTPM-UHFFFAOYSA-N 0.000 claims 1
- DLGWJZCZGOBODI-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylic acid Chemical compound C1=C2OCOC2=CC(C2C3=C(C4=CC=CC=C4N3)CC3=C(C(O)=O)C=C(N23)CO)=C1 DLGWJZCZGOBODI-UHFFFAOYSA-N 0.000 claims 1
- RDWQVLJPTAXCFA-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-1-ethyl-9,10-dihydro-4h-indolizino[6,7-b]indole-2,3-dicarboxylic acid Chemical compound C1=C2OCOC2=CC(C2C3=C(C4=CC=CC=C4N3)CC3=C(C(O)=O)C(C(O)=O)=C(N23)CC)=C1 RDWQVLJPTAXCFA-UHFFFAOYSA-N 0.000 claims 1
- DNQXUWRDZOPPFB-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-1-ethyl-n-(pyridin-2-ylmethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C=12CC(C3=CC=CC=C3N3)=C3C(C=3C=C4OCOC4=CC=3)N2C(CC)=CC=1C(=O)NCC1=CC=CC=N1 DNQXUWRDZOPPFB-UHFFFAOYSA-N 0.000 claims 1
- XJUUIYHCSBQPDR-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-1-methyl-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carbonitrile Chemical compound C1=C2OCOC2=CC(C2C3=C(C4=CC=CC=C4N3)CC3=C(C#N)C=C(N23)C)=C1 XJUUIYHCSBQPDR-UHFFFAOYSA-N 0.000 claims 1
- SJPCAMCRLVVREU-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-1-methyl-n-(2-morpholin-4-ylethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C=12CC(C3=CC=CC=C3N3)=C3C(C=3C=C4OCOC4=CC=3)N2C(C)=CC=1C(=O)NCCN1CCOCC1 SJPCAMCRLVVREU-UHFFFAOYSA-N 0.000 claims 1
- YCYQPRDAIVSXCT-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-1-propan-2-yl-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylic acid Chemical compound C1=C2OCOC2=CC(C2C3=C(C4=CC=CC=C4N3)CC3=C(C(O)=O)C=C(N23)C(C)C)=C1 YCYQPRDAIVSXCT-UHFFFAOYSA-N 0.000 claims 1
- HWHRRSDUBIMBJR-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole Chemical compound N1C2=CC=CC=C2C(CC=2N3C=CC=2)=C1C3C1=CC=C2OCOC2=C1 HWHRRSDUBIMBJR-UHFFFAOYSA-N 0.000 claims 1
- ILRSCFGFCLTQCF-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylic acid Chemical compound C1=C2OCOC2=CC(C2N3C=CC(=C3CC=3C4=CC=CC=C4NC=32)C(=O)O)=C1 ILRSCFGFCLTQCF-UHFFFAOYSA-N 0.000 claims 1
- TXVQXEJGBXFMAD-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-n-(2-pyrazol-1-ylethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C1=CN2C(C=3C=C4OCOC4=CC=3)C=3NC4=CC=CC=C4C=3CC2=C1C(=O)NCCN1C=CC=N1 TXVQXEJGBXFMAD-UHFFFAOYSA-N 0.000 claims 1
- FLLUZYQDDVCWPY-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-n-(2-pyridin-2-ylethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C1=CN2C(C=3C=C4OCOC4=CC=3)C=3NC4=CC=CC=C4C=3CC2=C1C(=O)NCCC1=CC=CC=N1 FLLUZYQDDVCWPY-UHFFFAOYSA-N 0.000 claims 1
- OVTMSTUPKJJQRN-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-n-(4-methylpiperazin-1-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C1CN(C)CCN1NC(=O)C1=C2CC(C3=CC=CC=C3N3)=C3C(C=3C=C4OCOC4=CC=3)N2C=C1 OVTMSTUPKJJQRN-UHFFFAOYSA-N 0.000 claims 1
- OWVMZWRKLCJCIJ-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-n-(oxolan-2-ylmethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C1=CN2C(C=3C=C4OCOC4=CC=3)C=3NC4=CC=CC=C4C=3CC2=C1C(=O)NCC1CCCO1 OWVMZWRKLCJCIJ-UHFFFAOYSA-N 0.000 claims 1
- WJNJFAZFUXUMLE-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-n-(pyridin-2-ylmethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C1=CN2C(C=3C=C4OCOC4=CC=3)C=3NC4=CC=CC=C4C=3CC2=C1C(=O)NCC1=CC=CC=N1 WJNJFAZFUXUMLE-UHFFFAOYSA-N 0.000 claims 1
- ZHXYWFOIKRBOOZ-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-n-(pyridin-3-ylmethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C1=CN2C(C=3C=C4OCOC4=CC=3)C=3NC4=CC=CC=C4C=3CC2=C1C(=O)NCC1=CC=CN=C1 ZHXYWFOIKRBOOZ-UHFFFAOYSA-N 0.000 claims 1
- FIJZKWASZRMLCZ-UHFFFAOYSA-N 10-(1,3-benzodioxol-5-yl)-n-methyl-n-(1-methylpiperidin-4-yl)-1-propan-2-yl-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C=12CC(C3=CC=CC=C3N3)=C3C(C=3C=C4OCOC4=CC=3)N2C(C(C)C)=CC=1C(=O)N(C)C1CCN(C)CC1 FIJZKWASZRMLCZ-UHFFFAOYSA-N 0.000 claims 1
- DWLUIKHJGBQJOH-UHFFFAOYSA-N 10-(2,3-dihydro-1-benzofuran-5-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylic acid Chemical compound C1=C2OCCC2=CC(C2N3C=CC(=C3CC=3C4=CC=CC=C4NC=32)C(=O)O)=C1 DWLUIKHJGBQJOH-UHFFFAOYSA-N 0.000 claims 1
- HOEMNSXAKLUFOI-UHFFFAOYSA-N 10-(4-chlorophenyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylic acid Chemical compound C1=2NC3=CC=CC=C3C=2CC2=C(C(=O)O)C=CN2C1C1=CC=C(Cl)C=C1 HOEMNSXAKLUFOI-UHFFFAOYSA-N 0.000 claims 1
- JZFNRVUJGVQOKK-UHFFFAOYSA-N 10-(4-methoxyphenyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1N2C=CC(C(O)=O)=C2CC2=C1NC1=CC=CC=C12 JZFNRVUJGVQOKK-UHFFFAOYSA-N 0.000 claims 1
- DFPOPVFJGHNNDL-UHFFFAOYSA-N 10-(4-methoxyphenyl)-n-(2-morpholin-4-ylethyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1N2C=CC(C(=O)NCCN3CCOCC3)=C2CC2=C1NC1=CC=CC=C12 DFPOPVFJGHNNDL-UHFFFAOYSA-N 0.000 claims 1
- MRJXAQNGEWPGIK-UHFFFAOYSA-N 10-phenyl-9,10-dihydro-4h-indolizino[6,7-b]indole-2-carboxylic acid Chemical compound N12C=C(C(=O)O)C=C2CC(C2=CC=CC=C2N2)=C2C1C1=CC=CC=C1 MRJXAQNGEWPGIK-UHFFFAOYSA-N 0.000 claims 1
- OPGNJKHSEKBZPJ-UHFFFAOYSA-N 2-[[10-(1,3-benzodioxol-5-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carbonyl]-methylamino]acetic acid Chemical compound C1=C2OCOC2=CC(C2N3C=CC(=C3CC=3C4=CC=CC=C4NC=32)C(=O)N(CC(O)=O)C)=C1 OPGNJKHSEKBZPJ-UHFFFAOYSA-N 0.000 claims 1
- MTBJODMXTRZIKU-UHFFFAOYSA-N 2-cyclopenta[c]pyran-5-yl-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C(C2)=C1CN1C2=C(C(=O)O)C(C2=C3C=COC=C3C=C2)=C1 MTBJODMXTRZIKU-UHFFFAOYSA-N 0.000 claims 1
- 208000017228 Gastrointestinal motility disease Diseases 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- QJFHBEQORIHFEE-UHFFFAOYSA-N diethyl 10-(1,3-benzodioxol-5-yl)-1-ethyl-9,10-dihydro-4h-indolizino[6,7-b]indole-2,3-dicarboxylate Chemical compound C1=C2OCOC2=CC(C2N3C(CC)=C(C(=C3CC=3C4=CC=CC=C4NC=32)C(=O)OCC)C(=O)OCC)=C1 QJFHBEQORIHFEE-UHFFFAOYSA-N 0.000 claims 1
- SZYNUMLJILUWHI-UHFFFAOYSA-N diethyl 10-(1,3-benzodioxol-5-yl)-1-propan-2-yl-9,10-dihydro-4h-indolizino[6,7-b]indole-2,3-dicarboxylate Chemical compound C1=C2OCOC2=CC(C2C3=C(C4=CC=CC=C4N3)CC3=C(C(=C(C(C)C)N32)C(=O)OCC)C(=O)OCC)=C1 SZYNUMLJILUWHI-UHFFFAOYSA-N 0.000 claims 1
- NTTZMMBPHBRSPH-UHFFFAOYSA-N diethyl 10-(1,3-benzodioxol-5-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole-2,3-dicarboxylate Chemical compound C1=C2OCOC2=CC(C2N3C=C(C(=C3CC=3C4=CC=CC=C4NC=32)C(=O)OCC)C(=O)OCC)=C1 NTTZMMBPHBRSPH-UHFFFAOYSA-N 0.000 claims 1
- WCHUPFUYSCFGKJ-UHFFFAOYSA-N dimethyl indole-1,2-dicarboxylate Chemical compound C1=CC=C2N(C(=O)OC)C(C(=O)OC)=CC2=C1 WCHUPFUYSCFGKJ-UHFFFAOYSA-N 0.000 claims 1
- CSQGNBLKFOYSRU-UHFFFAOYSA-N ethyl 10-(1,3-benzodioxol-5-yl)-1-[(benzylamino)methyl]-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylate Chemical compound N12C(C=3C=C4OCOC4=CC=3)C=3NC4=CC=CC=C4C=3CC2=C(C(=O)OCC)C=C1CNCC1=CC=CC=C1 CSQGNBLKFOYSRU-UHFFFAOYSA-N 0.000 claims 1
- OMCTUOMYOGJQIU-UHFFFAOYSA-N ethyl 10-(1,3-benzodioxol-5-yl)-1-ethyl-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylate Chemical compound C1=C2OCOC2=CC(C2N3C(CC)=CC(=C3CC=3C4=CC=CC=C4NC=32)C(=O)OCC)=C1 OMCTUOMYOGJQIU-UHFFFAOYSA-N 0.000 claims 1
- HCBOKBWCCUDXFJ-UHFFFAOYSA-N ethyl 10-(1,3-benzodioxol-5-yl)-1-methyl-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylate Chemical compound C1=C2OCOC2=CC(C2N3C(C)=CC(=C3CC=3C4=CC=CC=C4NC=32)C(=O)OCC)=C1 HCBOKBWCCUDXFJ-UHFFFAOYSA-N 0.000 claims 1
- PJHPMARKAPCNHE-UHFFFAOYSA-N ethyl 10-(1,3-benzodioxol-5-yl)-9,10-dihydro-4h-indolizino[6,7-b]indole-2-carboxylate Chemical compound C1=C2OCOC2=CC(C2C3=C(C4=CC=CC=C4N3)CC3=CC(=CN32)C(=O)OCC)=C1 PJHPMARKAPCNHE-UHFFFAOYSA-N 0.000 claims 1
- IFSFBFRZFAUAJU-UHFFFAOYSA-N ethyl 10-(4-methoxyphenyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-2-carboxylate Chemical compound N12C=C(C(=O)OCC)C=C2CC(C2=CC=CC=C2N2)=C2C1C1=CC=C(OC)C=C1 IFSFBFRZFAUAJU-UHFFFAOYSA-N 0.000 claims 1
- FLQZEIVUCMIGHZ-UHFFFAOYSA-N ethyl 10-(4-methoxyphenyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylate Chemical compound C1=2NC3=CC=CC=C3C=2CC2=C(C(=O)OCC)C=CN2C1C1=CC=C(OC)C=C1 FLQZEIVUCMIGHZ-UHFFFAOYSA-N 0.000 claims 1
- BOBICJMXWJBTCD-UHFFFAOYSA-N ethyl 10-(4-methylphenyl)-9,10-dihydro-4h-indolizino[6,7-b]indole-3-carboxylate Chemical compound C1=2NC3=CC=CC=C3C=2CC2=C(C(=O)OCC)C=CN2C1C1=CC=C(C)C=C1 BOBICJMXWJBTCD-UHFFFAOYSA-N 0.000 claims 1
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- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23724000P | 2000-10-02 | 2000-10-02 | |
| US237240P | 2000-10-02 | ||
| PCT/US2001/042173 WO2002028859A2 (en) | 2000-10-02 | 2001-09-17 | Condensed pyridoindole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60112960D1 DE60112960D1 (de) | 2005-09-29 |
| DE60112960T2 true DE60112960T2 (de) | 2006-02-09 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60112960T Expired - Lifetime DE60112960T2 (de) | 2000-10-02 | 2001-09-17 | Kondensierte pyridoindolderivate |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6838456B2 (enExample) |
| EP (1) | EP1335917B1 (enExample) |
| JP (1) | JP4220776B2 (enExample) |
| AT (1) | ATE302776T1 (enExample) |
| AU (1) | AU2002213419A1 (enExample) |
| CA (1) | CA2423308A1 (enExample) |
| DE (1) | DE60112960T2 (enExample) |
| ES (1) | ES2248399T3 (enExample) |
| MX (1) | MXPA03002909A (enExample) |
| WO (1) | WO2002028859A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE335742T1 (de) * | 2001-06-21 | 2006-09-15 | Lilly Icos Llc | Carbolinderivate als pdev inhibitoren |
| PL377657A1 (pl) | 2002-12-13 | 2006-02-06 | Warner-Lambert Company Llc | Ligand Ó-2-Ű do leczenia dolegliwości dolnych dróg moczowych |
| BRPI0506994A (pt) | 2004-01-22 | 2007-07-03 | Pfizer | derivados de triazol que inibem a atividade antagonista da vasopressina |
| US7501438B2 (en) * | 2006-07-07 | 2009-03-10 | Forest Laboratories Holdings Limited | Pyridoimidazole derivatives |
| JP2009027396A (ja) | 2007-07-19 | 2009-02-05 | Riso Kagaku Corp | 印刷装置 |
| EP2240481A1 (en) | 2008-01-11 | 2010-10-20 | Albany Molecular Research, Inc. | (1-azinone) -substituted pyridoindoles as mch antagonists |
| WO2010015585A1 (en) * | 2008-08-05 | 2010-02-11 | Nycomed Gmbh | 6-benzyl-2,3,4,7-tetrahydro-indolo[2,3-c]quinoline compounds |
| US8629158B2 (en) | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| WO2011003021A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| WO2011003005A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azepino[b]indole and pyrido-pyrrolo-azepine mch-1 antagonists, methods of making, and use thereof |
| WO2011003012A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle mch-1 antagonists, methods of making, and use thereof |
| WO2012088124A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline mch-1 antagonists, methods of making, and uses thereof |
| WO2012088038A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline mch-1 antagonists, methods of making, and uses thereof |
| US8703951B2 (en) * | 2011-07-15 | 2014-04-22 | Academia Sinica | Synthesis of 4H-benzo[D]pyrrolo[1,2-A]thiazoles and indolizino[6,7-b]indole derivatives and their use as antitumor therapeutic agents |
| CN113024553B (zh) * | 2021-03-16 | 2022-02-25 | 皖南医学院 | 三唑并四氢-β-咔啉衍生物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3459758A (en) * | 1967-11-09 | 1969-08-05 | Searle & Co | 9,10 - dihydro - 4h - pyrazolo(1',5':1,6)pyrido (3,4-b)indole - 2,3 - dicarboxylic acids and esters |
| GB9401090D0 (en) | 1994-01-21 | 1994-03-16 | Glaxo Lab Sa | Chemical compounds |
| GB9514465D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
| GB9514473D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
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2001
- 2001-09-17 CA CA002423308A patent/CA2423308A1/en not_active Abandoned
- 2001-09-17 WO PCT/US2001/042173 patent/WO2002028859A2/en not_active Ceased
- 2001-09-17 ES ES01981802T patent/ES2248399T3/es not_active Expired - Lifetime
- 2001-09-17 AU AU2002213419A patent/AU2002213419A1/en not_active Abandoned
- 2001-09-17 MX MXPA03002909A patent/MXPA03002909A/es active IP Right Grant
- 2001-09-17 EP EP01981802A patent/EP1335917B1/en not_active Expired - Lifetime
- 2001-09-17 AT AT01981802T patent/ATE302776T1/de not_active IP Right Cessation
- 2001-09-17 DE DE60112960T patent/DE60112960T2/de not_active Expired - Lifetime
- 2001-09-17 US US10/363,475 patent/US6838456B2/en not_active Expired - Fee Related
- 2001-09-17 JP JP2002532442A patent/JP4220776B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002213419A1 (en) | 2002-04-15 |
| WO2002028859A3 (en) | 2002-09-12 |
| US20030207906A1 (en) | 2003-11-06 |
| EP1335917B1 (en) | 2005-08-24 |
| MXPA03002909A (es) | 2003-09-10 |
| US6838456B2 (en) | 2005-01-04 |
| DE60112960D1 (de) | 2005-09-29 |
| ES2248399T3 (es) | 2006-03-16 |
| WO2002028859A2 (en) | 2002-04-11 |
| JP2004510774A (ja) | 2004-04-08 |
| JP4220776B2 (ja) | 2009-02-04 |
| ATE302776T1 (de) | 2005-09-15 |
| CA2423308A1 (en) | 2002-04-11 |
| EP1335917A2 (en) | 2003-08-20 |
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