JP2016526576A5 - - Google Patents
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- JP2016526576A5 JP2016526576A5 JP2016527011A JP2016527011A JP2016526576A5 JP 2016526576 A5 JP2016526576 A5 JP 2016526576A5 JP 2016527011 A JP2016527011 A JP 2016527011A JP 2016527011 A JP2016527011 A JP 2016527011A JP 2016526576 A5 JP2016526576 A5 JP 2016526576A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- indol
- methoxy
- piperidin
- dimethyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 16
- 239000011780 sodium chloride Substances 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- -1 -CH 2 C (O) R 7 Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005842 heteroatoms Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- NHSANTONQVVKKW-UHFFFAOYSA-N 4-[1-[(5,7-dimethyl-1H-indol-4-yl)methyl]-4-ethoxypiperidin-2-yl]benzoic acid Chemical compound C1C(OCC)CCN(CC=2C=3C=CNC=3C(C)=CC=2C)C1C1=CC=C(C(O)=O)C=C1 NHSANTONQVVKKW-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 206010064930 Age-related macular degeneration Diseases 0.000 claims 2
- 108010047814 Antigen-Antibody Complex Proteins 0.000 claims 2
- 208000006673 Asthma Diseases 0.000 claims 2
- 206010003816 Autoimmune disease Diseases 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 108009000280 Complement Activation Proteins 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
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 201000005794 allergic hypersensitivity disease Diseases 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 230000024203 complement activation Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 125000004434 sulfur atoms Chemical group 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 125000004178 (C1-C4) alkyl 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
- WHSFJJAVNLAHGJ-UHFFFAOYSA-N 1-[(5,7-dimethyl-1H-indol-4-yl)methyl]-N-methyl-2-phenylpiperidin-4-amine Chemical compound C1C(NC)CCN(CC=2C=3C=CNC=3C(C)=CC=2C)C1C1=CC=CC=C1 WHSFJJAVNLAHGJ-UHFFFAOYSA-N 0.000 claims 1
- HTLOSYCWFUEUMN-UHFFFAOYSA-N 2-[1-[(5,7-dimethyl-1H-indol-4-yl)methyl]-2-phenylpiperidin-4-yl]acetonitrile Chemical compound CC1=CC(C)=C2NC=CC2=C1CN1CCC(CC#N)CC1C1=CC=CC=C1 HTLOSYCWFUEUMN-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
- QDFYINAAIJVFKL-UHFFFAOYSA-N 2-methoxy-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(OC)=C1 QDFYINAAIJVFKL-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
- SUWQILGSQSOVBF-UHFFFAOYSA-N 4-[1-[(5,7-dimethyl-1H-indol-4-yl)methyl]-4-methoxypiperidin-2-yl]benzoic acid Chemical compound C1C(OC)CCN(CC=2C=3C=CNC=3C(C)=CC=2C)C1C1=CC=C(C(O)=O)C=C1 SUWQILGSQSOVBF-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
- 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
- RPFFEOOLBDGISZ-UHFFFAOYSA-N 4-[1-[(5-methoxy-7-methyl-1H-indol-4-yl)methyl]piperidin-2-yl]naphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C3CCCCN3CC3=C4C=CNC4=C(C)C=C3OC)=CC=C(C(O)=O)C2=C1 RPFFEOOLBDGISZ-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
- YYUUVVPZKILLQX-UHFFFAOYSA-N 4-[4-methoxy-1-[(5-methoxy-7-methyl-1H-indol-4-yl)methyl]piperidin-2-yl]-N,N-dimethylbenzamide Chemical compound C1C(OC)CCN(CC=2C=3C=CNC=3C(C)=CC=2OC)C1C1=CC=C(C(=O)N(C)C)C=C1 YYUUVVPZKILLQX-UHFFFAOYSA-N 0.000 claims 1
- SARRGNYAEXLPRZ-UHFFFAOYSA-N 4-[4-methoxy-1-[(5-methoxy-7-methyl-1H-indol-4-yl)methyl]piperidin-2-yl]-N-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1N(CC=2C=3C=CNC=3C(C)=CC=2OC)CCC(OC)C1 SARRGNYAEXLPRZ-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
- VMXHDPCIIAMFBA-UHFFFAOYSA-N 4-[5-methoxy-1-[(5-methoxy-7-methyl-1H-indol-4-yl)methyl]piperidin-2-yl]benzamide Chemical compound COC=1C=C(C)C=2NC=CC=2C=1CN1CC(OC)CCC1C1=CC=C(C(N)=O)C=C1 VMXHDPCIIAMFBA-UHFFFAOYSA-N 0.000 claims 1
- GTZIJSWOJBPQBP-UHFFFAOYSA-N 4-[6-[(5-methoxy-7-methyl-1H-indol-4-yl)methyl]-6-azaspiro[2.5]octan-7-yl]benzoic acid Chemical compound COC1=CC(C)=C2NC=CC2=C1CN(C(C1)C=2C=CC(=CC=2)C(O)=O)CCC21CC2 GTZIJSWOJBPQBP-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
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| EP3340982B1 (en) | 2015-08-26 | 2021-12-15 | Achillion Pharmaceuticals, Inc. | Compounds for treatment of immune and inflammatory disorders |
| US11332470B2 (en) * | 2016-06-21 | 2022-05-17 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
| US10759796B2 (en) | 2016-06-21 | 2020-09-01 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
| AU2017290593A1 (en) * | 2016-06-27 | 2019-01-03 | Achillion Pharmaceuticals, Inc. | Quinazoline and indole compounds to treat medical disorders |
| CN113444046B (zh) * | 2016-07-20 | 2023-10-27 | 纳莹(上海)生物科技有限公司 | 一种荧光探针及其制备方法和用途 |
| KR20240019857A (ko) | 2017-03-01 | 2024-02-14 | 아칠리온 파르마세우티칼스 인코포레이티드 | 의학적 장애의 치료를 위한 아릴, 헤테로아릴, 및 헤테로사이클릭 약학적 화합물 |
| AU2018321157B2 (en) | 2017-08-24 | 2024-03-28 | Novo Nordisk A/S | GLP-1 compositions and uses thereof |
| CA3073346A1 (en) | 2017-08-31 | 2019-03-07 | Novartis Ag | Novel uses of piperidinyl-indole derivatives |
| EP3823963A2 (en) * | 2018-07-16 | 2021-05-26 | Novartis AG | Chemical process for preparing phenylpiperidinyl indole derivatives |
| JP7538113B2 (ja) | 2018-08-20 | 2024-08-21 | アキリオン ファーマシューティカルズ，インコーポレーテッド | 補体ｄ因子の医学的障害の治療のための医薬化合物 |
| JP2022502500A (ja) | 2018-09-25 | 2022-01-11 | アキリオン ファーマシューティカルズ， インコーポレーテッド | 補体因子ｄ阻害剤の形態 |
| BR112021013377A2 (pt) | 2019-01-11 | 2021-09-14 | Novartis Ag | Inibidores de lta4h para o tratamento de hidradenite supurativa |
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| MX2022009844A (es) | 2020-02-18 | 2022-09-05 | Novo Nordisk As | Composiciones y usos del peptido similar al glucagon-1 (glp-1). |
| EP4153580A1 (en) | 2020-05-18 | 2023-03-29 | Novartis AG | Crystalline form of lnp023 |
| WO2022013604A1 (en) | 2020-07-16 | 2022-01-20 | Novartis Ag | Methods of using factor b inhibitors |
| WO2022028527A1 (zh) * | 2020-08-07 | 2022-02-10 | 上海美悦生物科技发展有限公司 | 补体因子b抑制剂及其药物组合物、制备方法和用途 |
| WO2022028507A1 (zh) * | 2020-08-07 | 2022-02-10 | 上海美悦生物科技发展有限公司 | 一种杂环类化合物、其制备方法及用途 |
| CN116583508A (zh) * | 2020-12-30 | 2023-08-11 | 南京明德新药研发有限公司 | 一系列哌啶取代的苯酸类化合物及其应用 |
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| WO2022155294A1 (en) * | 2021-01-14 | 2022-07-21 | Alexion Pharmaceuticals, Inc. | Macrocycle complement factor b inhibitors |
| US20240217953A1 (en) * | 2021-04-16 | 2024-07-04 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Bicyclic substituted aromatic carboxylic acid compounds |
| KR20240004947A (ko) * | 2021-05-07 | 2024-01-11 | 노파르티스 아게 | 비정형 용혈성 요독 증후군 치료용 입타코판 |
| BR112023025235A2 (pt) * | 2021-06-03 | 2024-02-27 | Chinook Therapeutics Inc | Compostos de indol substituídos e métodos de uso dos mesmos |
| EP4355329A1 (en) | 2021-06-18 | 2024-04-24 | Novartis AG | Method of treating an autoimmune hematological disorder |
| WO2023278698A1 (en) * | 2021-06-30 | 2023-01-05 | Apellis Pharmaceuticals, Inc. | Complement inhibition |
| CN118043314A (zh) * | 2021-08-18 | 2024-05-14 | 西藏海思科制药有限公司 | 一种苯并氮杂芳环衍生物及其在医药上的应用 |
| WO2023037218A1 (en) | 2021-09-07 | 2023-03-16 | Novartis Ag | Use of factor b inhibitors for the treatment of age-related macular degeneration |
| KR20240090506A (ko) * | 2021-10-27 | 2024-06-21 | 한서 바이오 엘엘씨 | 피페리디닐 인돌 유도체, 이의 제조 방법 및 의약적 용도 |
| IL314186A (en) | 2022-01-24 | 2024-09-01 | Novartis Ag | PIPERIDINYL SPIROCYCLIC DERIVATIVES AS COMPLEMENT B FACTOR INHIBITORS AND USES THEREOF |
| CN116496249A (zh) * | 2022-01-26 | 2023-07-28 | 上海美悦生物科技发展有限公司 | 补体因子b抑制剂的盐型、晶型及其制备方法和应用 |
| TW202342048A (zh) | 2022-02-28 | 2023-11-01 | 瑞士商諾華公司 | 使用ｌｏｕ０６４治療化膿性汗腺炎之方法 |
| IL314494A (en) | 2022-03-04 | 2024-09-01 | Novartis Ag | Use of Iptacopan to treat lupus nephritis |
| WO2023187715A1 (en) | 2022-04-01 | 2023-10-05 | Novartis Ag | Complement factor b inhibitors and uses thereof |
| WO2023246677A1 (zh) * | 2022-06-20 | 2023-12-28 | 深圳信立泰药业股份有限公司 | 一种吲哚-苯基哌啶化合物及其制备方法与应用 |
| WO2023246870A1 (zh) * | 2022-06-23 | 2023-12-28 | 上海济煜医药科技有限公司 | 吲哚化合物的制备、应用及用途 |
| WO2024002353A1 (zh) * | 2022-06-30 | 2024-01-04 | 江苏恒瑞医药股份有限公司 | 一种含氮桥杂环衍生物的可药用盐、晶型及其制备方法 |
| WO2024046277A1 (zh) * | 2022-08-29 | 2024-03-07 | 南京明德新药研发有限公司 | 一系列含氮桥杂环化合物及其制备方法 |
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| WO2024051849A1 (en) * | 2022-09-10 | 2024-03-14 | Jiangsu Hansoh Pharmaceutical Group Co., Ltd. | 2-substituted piperidine derivatives, preparation methods and medicinal uses thereof |
| CN118026998A (zh) * | 2022-11-11 | 2024-05-14 | 上海医药工业研究院有限公司 | 哌啶取代的苯甲酸类化合物、其药物组合物和应用 |
| WO2024104292A1 (en) * | 2022-11-14 | 2024-05-23 | Novartis Pharma Ag | Solid forms of complement factor b inhibitors |
| WO2024114677A1 (zh) * | 2022-11-29 | 2024-06-06 | 上海济煜医药科技有限公司 | 苯并螺环吲哚化合物的制备、应用及用途 |
| WO2024141011A1 (zh) * | 2022-12-31 | 2024-07-04 | 深圳晶泰科技有限公司 | 补体因子b抑制剂及其药物组合物和应用 |
| WO2024148274A1 (en) * | 2023-01-05 | 2024-07-11 | Apellis Pharmaceuticals, Inc. | Complement inhibition |
| WO2024175028A1 (zh) * | 2023-02-22 | 2024-08-29 | 西藏海思科制药有限公司 | 一种苯并氮杂芳环衍生物的药物组合物及其在医药上的应用 |
| WO2024176169A1 (en) | 2023-02-23 | 2024-08-29 | Novartis Ag | Methods of using factor b inhibitors |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR030357A1 (es) | 2000-08-18 | 2003-08-20 | Lundbeck & Co As H | Derivados 4 -, 5 -, 6 - y 7-indol |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| DE10237723A1 (de) * | 2002-08-17 | 2004-07-08 | Aventis Pharma Deutschland Gmbh | Verwendung von IKappaB-Kinase Inhibitoren in der Schmerztherapie |
| SI1585743T1 (sl) | 2002-12-19 | 2007-08-31 | Pfizer | Spojine 2-(1H-indazol-6-ilamino)-benzamida kot inhibitorji protein-kinaz, uporabnih pri zdravljenju očesnih bolezni |
| US7524878B2 (en) | 2003-04-30 | 2009-04-28 | The Institute For Pharmaceuticals Discovery Llc | Phenyl substituted carboxylic acids |
| JP2008520683A (ja) | 2004-11-18 | 2008-06-19 | ジ インスチチュート フォー ファーマシューティカル ディスカバリー、エルエルシー | タンパク質チロシンホスファターゼ阻害剤としてのヘテロシクリルビフェニル誘導体 |
| CN101115724A (zh) | 2005-02-08 | 2008-01-30 | 默克公司 | 关卡激酶抑制剂 |
| WO2009042092A1 (en) | 2007-09-25 | 2009-04-02 | Merck & Co., Inc. | 2-aryl or heteroaryl indole derivatives |
| US20100331298A1 (en) | 2007-12-10 | 2010-12-30 | Cytopathfinder, Inc. | Carboxamide Compounds and Their Use |
| AR070398A1 (es) | 2008-02-22 | 2010-03-31 | Gruenenthal Chemie | Derivados sustituidos de indol |
| JO3265B1 (ar) | 2008-12-09 | 2018-09-16 | Novartis Ag | مثبطات بيريديلوكسى اندولات vegf-r2 واستخدامها لعلاج المرض |
| JP5852958B2 (ja) | 2009-07-14 | 2016-02-03 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | Ｐａｒｐ阻害剤としての３−オキソ−２，３−ジヒドロ−１ｈ−イソインドール−４−カルボキサミド |
| CN104592205A (zh) | 2010-03-01 | 2015-05-06 | Gtx公司 | 用于治疗癌的化合物 |
| WO2012068589A2 (en) | 2010-11-19 | 2012-05-24 | Constellation Pharmaceuticals | Modulators of methyl modifying enzymes, compositions and uses thereof |
| PT2661433T (pt) | 2011-01-04 | 2017-10-24 | Novartis Ag | Compostos de indole ou seus análogos úteis para o tratamento da degeneração macular relacionada com a idade (amd) |
| KR20150003903A (ko) * | 2012-05-04 | 2015-01-09 | 노파르티스 아게 | 보체 경로 조절제 및 그의 용도 |
| AU2013277154A1 (en) | 2012-06-20 | 2014-12-18 | Jonathan E. Grob | Complement pathway modulators and uses thereof |
| JO3425B1 (ar) | 2013-07-15 | 2019-10-20 | Novartis Ag | مشتقات البابيريدينيل-اندول واستخدامها كعامل متمم لمثبطات b |
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