SI3022192T1 - Piperidinyl indole derivatives and their use as inhibitors of complementary factor B - Google Patents
Piperidinyl indole derivatives and their use as inhibitors of complementary factor B Download PDFInfo
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- SI3022192T1 SI3022192T1 SI201430522T SI201430522T SI3022192T1 SI 3022192 T1 SI3022192 T1 SI 3022192T1 SI 201430522 T SI201430522 T SI 201430522T SI 201430522 T SI201430522 T SI 201430522T SI 3022192 T1 SI3022192 T1 SI 3022192T1
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- Slovenia
- Prior art keywords
- methyl
- indol
- methoxy
- piperidin
- dimethyl
- Prior art date
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- 102000003712 Complement factor B Human genes 0.000 title claims abstract 3
- 108090000056 Complement factor B Proteins 0.000 title claims abstract 3
- 239000003112 inhibitor Substances 0.000 title claims abstract 3
- HNQZRUDJRPSFAU-UHFFFAOYSA-N 2-piperidin-1-yl-1h-indole Chemical class C1CCCCN1C1=CC2=CC=CC=C2N1 HNQZRUDJRPSFAU-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 23
- 239000013543 active substance Substances 0.000 claims abstract 2
- 230000000295 complement effect Effects 0.000 claims abstract 2
- 230000037361 pathway Effects 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- -1 cyanomethyl Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 239000005711 Benzoic acid Substances 0.000 claims 4
- 235000010233 benzoic acid Nutrition 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 230000024203 complement activation Effects 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 230000002980 postoperative effect Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 230000010410 reperfusion Effects 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- DKUNNNWHLNFFMK-UHFFFAOYSA-N 1-[(5,7-dimethyl-1h-indol-4-yl)methyl]-2-phenylpiperidin-4-amine Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCC(N)CC1C1=CC=CC=C1 DKUNNNWHLNFFMK-UHFFFAOYSA-N 0.000 claims 1
- UMSSUFIOUNRNIX-UHFFFAOYSA-N 2-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]-1,3-thiazole-4-carboxylic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=NC(C(O)=O)=CS1 UMSSUFIOUNRNIX-UHFFFAOYSA-N 0.000 claims 1
- XKYJIXRWXNBCJM-UHFFFAOYSA-N 2-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=NC(C)=C(C(O)=O)S1 XKYJIXRWXNBCJM-UHFFFAOYSA-N 0.000 claims 1
- BSWKNXRAIJPUKI-UHFFFAOYSA-N 2-[3-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]phenyl]acetic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=CC(CC(O)=O)=C1 BSWKNXRAIJPUKI-UHFFFAOYSA-N 0.000 claims 1
- UKTVVFRPPPWVAF-UHFFFAOYSA-N 2-[4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]phenyl]acetic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(CC(O)=O)C=C1 UKTVVFRPPPWVAF-UHFFFAOYSA-N 0.000 claims 1
- ILKBLZXBYIJHIL-UHFFFAOYSA-N 2-[4-ethoxy-1-[(5-methoxy-7-methyl-1H-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound C(C)OC1CC(N(CC1)CC1=C2C=CNC2=C(C=C1OC)C)C1=C(C(=O)O)C=CC=C1 ILKBLZXBYIJHIL-UHFFFAOYSA-N 0.000 claims 1
- UASNJUCFJIWSEG-UHFFFAOYSA-N 3-[1-[(5,7-dimethyl-1H-indol-4-yl)methyl]piperidin-2-yl]-N-methylbenzenesulfonamide Chemical compound CC=1C(=C2C=CNC2=C(C=1)C)CN1C(CCCC1)C=1C=C(C=CC=1)S(=O)(=O)NC UASNJUCFJIWSEG-UHFFFAOYSA-N 0.000 claims 1
- PRHWUJYHWKQVQL-UHFFFAOYSA-N 3-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzamide Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=CC(C(N)=O)=C1 PRHWUJYHWKQVQL-UHFFFAOYSA-N 0.000 claims 1
- LELUIAVFYRGZDZ-UHFFFAOYSA-N 3-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzenesulfonamide Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=CC(S(N)(=O)=O)=C1 LELUIAVFYRGZDZ-UHFFFAOYSA-N 0.000 claims 1
- IDAQIBNNEOTNPN-UHFFFAOYSA-N 3-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=CC(C(O)=O)=C1 IDAQIBNNEOTNPN-UHFFFAOYSA-N 0.000 claims 1
- RADYRXMLAQSJFJ-UHFFFAOYSA-N 3-fluoro-4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(C(O)=O)C=C1F RADYRXMLAQSJFJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- YMPJBKLLEMBQMA-UHFFFAOYSA-N 4-[(4-methoxy-2-phenylpiperidin-1-yl)methyl]-5,7-dimethyl-1h-indole Chemical compound C1C(OC)CCN(CC=2C=3C=CNC=3C(C)=CC=2C)C1C1=CC=CC=C1 YMPJBKLLEMBQMA-UHFFFAOYSA-N 0.000 claims 1
- ZHDZULFFIFOFPB-UHFFFAOYSA-N 4-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]-4-hydroxypiperidin-2-yl]benzoic acid Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCC(O)CC1C1=CC=C(C(O)=O)C=C1 ZHDZULFFIFOFPB-UHFFFAOYSA-N 0.000 claims 1
- IMCMTUPLZRVGQR-UHFFFAOYSA-N 4-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]-4-methoxypiperidin-2-yl]benzamide Chemical compound C1C(OC)CCN(CC=2C=3C=CNC=3C(C)=CC=2C)C1C1=CC=C(C(N)=O)C=C1 IMCMTUPLZRVGQR-UHFFFAOYSA-N 0.000 claims 1
- SJUCFJDWRTWOME-UHFFFAOYSA-N 4-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]piperidin-2-yl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1N(CC=2C=3C=CNC=3C(C)=CC=2C)CCCC1 SJUCFJDWRTWOME-UHFFFAOYSA-N 0.000 claims 1
- HVCYKNQNKTXZHC-UHFFFAOYSA-N 4-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzamide Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(C(N)=O)C=C1 HVCYKNQNKTXZHC-UHFFFAOYSA-N 0.000 claims 1
- LPTZYRLQBKRUAO-UHFFFAOYSA-N 4-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzenesulfonamide Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(S(N)(=O)=O)C=C1 LPTZYRLQBKRUAO-UHFFFAOYSA-N 0.000 claims 1
- OTSLYLLOBTYVLP-UHFFFAOYSA-N 4-[1-[(5,7-dimethyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(C(O)=O)C=C1 OTSLYLLOBTYVLP-UHFFFAOYSA-N 0.000 claims 1
- VVYYBWFVWGOHGG-UHFFFAOYSA-N 4-[1-[(5-chloro-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzamide Chemical compound C1=2C=CNC=2C(C)=CC(Cl)=C1CN1CCCCC1C1=CC=C(C(N)=O)C=C1 VVYYBWFVWGOHGG-UHFFFAOYSA-N 0.000 claims 1
- BVTJTVYFVKEMQJ-UHFFFAOYSA-N 4-[1-[(5-chloro-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound C1=2C=CNC=2C(C)=CC(Cl)=C1CN1CCCCC1C1=CC=C(C(O)=O)C=C1 BVTJTVYFVKEMQJ-UHFFFAOYSA-N 0.000 claims 1
- JSQMNTWGQUIWQT-UHFFFAOYSA-N 4-[1-[(5-cyclopropyl-7-methyl-1h-indol-4-yl)methyl]-4-ethoxypiperidin-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C1CC(OCC)CCN1CC(C=1C=CNC=1C(C)=C1)=C1C1CC1 JSQMNTWGQUIWQT-UHFFFAOYSA-N 0.000 claims 1
- CKPFEBYAYLCXDR-UHFFFAOYSA-N 4-[1-[(5-cyclopropyl-7-methyl-1h-indol-4-yl)methyl]-4-methoxypiperidin-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C1CC(OC)CCN1CC(C=1C=CNC=1C(C)=C1)=C1C1CC1 CKPFEBYAYLCXDR-UHFFFAOYSA-N 0.000 claims 1
- OUDHJLAYNXAKSM-UHFFFAOYSA-N 4-[1-[(5-cyclopropyl-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]-2-fluorobenzoic acid Chemical compound C1CCCC(C=2C=C(F)C(C(O)=O)=CC=2)N1CC=1C=2C=CNC=2C(C)=CC=1C1CC1 OUDHJLAYNXAKSM-UHFFFAOYSA-N 0.000 claims 1
- UCDGYFITIWQJJE-UHFFFAOYSA-N 4-[1-[(5-cyclopropyl-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1C1N(CC=2C=3C=CNC=3C(C)=CC=2C2CC2)CCCC1 UCDGYFITIWQJJE-UHFFFAOYSA-N 0.000 claims 1
- HTBXOVPODOBJFN-UHFFFAOYSA-N 4-[1-[(5-cyclopropyl-7-methyl-1h-indol-4-yl)methyl]pyrrolidin-2-yl]benzoic acid Chemical compound C1CCC(C=2C=CC(=CC=2)C(O)=O)N1CC=1C=2C=CNC=2C(C)=CC=1C1CC1 HTBXOVPODOBJFN-UHFFFAOYSA-N 0.000 claims 1
- BJJYQBOFWNDASV-UHFFFAOYSA-N 4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]-4,4-dimethylpiperidin-2-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCC(C)(C)CC1C1=CC=C(C(O)=O)C=C1 BJJYQBOFWNDASV-UHFFFAOYSA-N 0.000 claims 1
- JRMYPSCIGHXTAS-UHFFFAOYSA-N 4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]-4-methylpiperidin-2-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCC(C)CC1C1=CC=C(C(O)=O)C=C1 JRMYPSCIGHXTAS-UHFFFAOYSA-N 0.000 claims 1
- PTJDUBVSNSKDOU-UHFFFAOYSA-N 4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]-4-propoxypiperidin-2-yl]benzoic acid Chemical compound C1C(OCCC)CCN(CC=2C=3C=CNC=3C(C)=CC=2OC)C1C1=CC=C(C(O)=O)C=C1 PTJDUBVSNSKDOU-UHFFFAOYSA-N 0.000 claims 1
- NSPDIFFDXAQSHO-UHFFFAOYSA-N 4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]-5-methylpiperidin-2-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CC(C)CCC1C1=CC=C(C(O)=O)C=C1 NSPDIFFDXAQSHO-UHFFFAOYSA-N 0.000 claims 1
- XYGTZXFQCWULFR-UHFFFAOYSA-N 4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]azepan-2-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCCC1C1=CC=C(C(O)=O)C=C1 XYGTZXFQCWULFR-UHFFFAOYSA-N 0.000 claims 1
- VCJGEZQYZSBAFB-UHFFFAOYSA-N 4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]-3-methylbenzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(C(O)=O)C=C1C VCJGEZQYZSBAFB-UHFFFAOYSA-N 0.000 claims 1
- VIRBVYVHADHXCS-UHFFFAOYSA-N 4-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(C(O)=O)C=C1 VIRBVYVHADHXCS-UHFFFAOYSA-N 0.000 claims 1
- XIDOAUYGHUTOAL-UHFFFAOYSA-N 4-[4-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]morpholin-3-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCOCC1C1=CC=C(C(O)=O)C=C1 XIDOAUYGHUTOAL-UHFFFAOYSA-N 0.000 claims 1
- BSYZFJFBADBOJA-UHFFFAOYSA-N 4-[4-ethoxy-1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzonitrile Chemical compound C1C(OCC)CCN(CC=2C=3C=CNC=3C(C)=CC=2OC)C1C1=CC=C(C#N)C=C1 BSYZFJFBADBOJA-UHFFFAOYSA-N 0.000 claims 1
- HDMDFUFRPJSUEC-UHFFFAOYSA-N 4-[4-ethyl-1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound C1C(CC)CCN(CC=2C=3C=CNC=3C(C)=CC=2OC)C1C1=CC=C(C(O)=O)C=C1 HDMDFUFRPJSUEC-UHFFFAOYSA-N 0.000 claims 1
- BDYAWFURHKPDFJ-UHFFFAOYSA-N 4-[4-hydroxy-1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCC(O)CC1C1=CC=C(C(O)=O)C=C1 BDYAWFURHKPDFJ-UHFFFAOYSA-N 0.000 claims 1
- PTVJLZRVTIPNBU-UHFFFAOYSA-N 4-[4-methoxy-1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]-4-methylpiperidin-2-yl]benzamide Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCC(C)(OC)CC1C1=CC=C(C(N)=O)C=C1 PTVJLZRVTIPNBU-UHFFFAOYSA-N 0.000 claims 1
- MNWOIQKVANULGE-UHFFFAOYSA-N 4-[4-methoxy-1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound C1C(OC)CCN(CC=2C=3C=CNC=3C(C)=CC=2OC)C1C1=CC=C(C(O)=O)C=C1 MNWOIQKVANULGE-UHFFFAOYSA-N 0.000 claims 1
- BQRDGRCUTGUVKK-UHFFFAOYSA-N 4-[5-hydroxy-1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CC(O)CCC1C1=CC=C(C(O)=O)C=C1 BQRDGRCUTGUVKK-UHFFFAOYSA-N 0.000 claims 1
- KGARRXKSPGRFFR-UHFFFAOYSA-N 4-[5-methoxy-1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]benzoic acid Chemical compound COC=1C=C(C)C=2NC=CC=2C=1CN1CC(OC)CCC1C1=CC=C(C(O)=O)C=C1 KGARRXKSPGRFFR-UHFFFAOYSA-N 0.000 claims 1
- BWVLOTHJSYXNJA-UHFFFAOYSA-N 4-[[2-(4-fluorophenyl)-4-methoxypiperidin-1-yl]methyl]-5,7-dimethyl-1h-indole Chemical compound C1C(OC)CCN(CC=2C=3C=CNC=3C(C)=CC=2C)C1C1=CC=C(F)C=C1 BWVLOTHJSYXNJA-UHFFFAOYSA-N 0.000 claims 1
- ZVINDOKATQVWPW-UHFFFAOYSA-N 4-[[4-ethoxy-2-[4-(2h-tetrazol-5-yl)phenyl]piperidin-1-yl]methyl]-5-methoxy-7-methyl-1h-indole Chemical compound C1C(OCC)CCN(CC=2C=3C=CNC=3C(C)=CC=2OC)C1C(C=C1)=CC=C1C=1N=NNN=1 ZVINDOKATQVWPW-UHFFFAOYSA-N 0.000 claims 1
- GRJUTCRGMYGLQC-UHFFFAOYSA-N 5,7-dimethyl-4-[(2-phenylpiperidin-1-yl)methyl]-1h-indole Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=CC=C1 GRJUTCRGMYGLQC-UHFFFAOYSA-N 0.000 claims 1
- KHQBQZAYKBKWTN-UHFFFAOYSA-N 5,7-dimethyl-4-[[2-(4-methylsulfonylphenyl)piperidin-1-yl]methyl]-1h-indole Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(S(C)(=O)=O)C=C1 KHQBQZAYKBKWTN-UHFFFAOYSA-N 0.000 claims 1
- QJAJIJDEGTUFEF-UHFFFAOYSA-N 5,7-dimethyl-4-[[2-[4-(2h-tetrazol-5-yl)phenyl]piperidin-1-yl]methyl]-1h-indole Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C(C=C1)=CC=C1C=1N=NNN=1 QJAJIJDEGTUFEF-UHFFFAOYSA-N 0.000 claims 1
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- CTLRFIOXKNONCU-UHFFFAOYSA-N 5-[1-[(5-cyclopropyl-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]pyridine-2-carboxylic acid Chemical compound C1CCCC(C=2C=NC(=CC=2)C(O)=O)N1CC=1C=2C=CNC=2C(C)=CC=1C1CC1 CTLRFIOXKNONCU-UHFFFAOYSA-N 0.000 claims 1
- FRRVRTXVWHXIJP-UHFFFAOYSA-N 5-methoxy-7-methyl-4-[(2-pyridin-3-ylpiperidin-1-yl)methyl]-1h-indole Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=CN=C1 FRRVRTXVWHXIJP-UHFFFAOYSA-N 0.000 claims 1
- NXJSXHHRXXZPSG-UHFFFAOYSA-N 5-methoxy-7-methyl-4-[(2-pyridin-4-ylpiperidin-1-yl)methyl]-1h-indole Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=NC=C1 NXJSXHHRXXZPSG-UHFFFAOYSA-N 0.000 claims 1
- QAMTYUYWOLBTEZ-UHFFFAOYSA-N 5-methoxy-7-methyl-4-[[2-[4-(1h-pyrazol-4-yl)phenyl]piperidin-1-yl]methyl]-1h-indole Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C(C=C1)=CC=C1C=1C=NNC=1 QAMTYUYWOLBTEZ-UHFFFAOYSA-N 0.000 claims 1
- AWNIBQJCDRHYFM-UHFFFAOYSA-N 5-methoxy-7-methyl-4-[[2-[4-(1h-pyrazol-5-yl)phenyl]piperidin-1-yl]methyl]-1h-indole Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C(C=C1)=CC=C1C1=CC=NN1 AWNIBQJCDRHYFM-UHFFFAOYSA-N 0.000 claims 1
- PDQZVULLRBJFBQ-UHFFFAOYSA-N 6-[1-[(5-methoxy-7-methyl-1h-indol-4-yl)methyl]piperidin-2-yl]pyridine-3-carboxylic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN1CCCCC1C1=CC=C(C(O)=O)C=N1 PDQZVULLRBJFBQ-UHFFFAOYSA-N 0.000 claims 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003694 Atrophy Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
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| US201361846355P | 2013-07-15 | 2013-07-15 | |
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| PCT/US2014/046515 WO2015009616A1 (en) | 2013-07-15 | 2014-07-14 | Piperidinyl indole derivatives and their use as complement factor b inhibitors |
| EP14744744.5A EP3022192B1 (en) | 2013-07-15 | 2014-07-14 | Piperidinyl indole derivatives and their use as complement factor b inhibitors |
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