CA2847193A1 - New enzyme inhibitor compounds - Google Patents
New enzyme inhibitor compounds Download PDFInfo
- Publication number
- CA2847193A1 CA2847193A1 CA2847193A CA2847193A CA2847193A1 CA 2847193 A1 CA2847193 A1 CA 2847193A1 CA 2847193 A CA2847193 A CA 2847193A CA 2847193 A CA2847193 A CA 2847193A CA 2847193 A1 CA2847193 A1 CA 2847193A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- chlorophenyl
- pyrazolo
- pyrrolo
- piperidin
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims description 145
- 239000002532 enzyme inhibitor Substances 0.000 title description 3
- 229940125532 enzyme inhibitor Drugs 0.000 title description 2
- 230000005764 inhibitory process Effects 0.000 claims abstract description 16
- YTYICXYLUBLDHM-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-c]pyridine Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCN(CC=3C=NC=CC=3)CC2)=N1 YTYICXYLUBLDHM-UHFFFAOYSA-N 0.000 claims abstract 2
- QATYRYIZQCZJPK-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-piperidin-4-ylpyrrolo[2,3-c]pyridin-4-ol Chemical compound C1=2C(O)=CN=CC=2N(C=2C=CC(Cl)=CC=2)C=C1C1CCNCC1 QATYRYIZQCZJPK-UHFFFAOYSA-N 0.000 claims abstract 2
- VKIWDHXNHBXEIH-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C1=CC=NC=C11)=NN1C1=CC=C(Cl)C=C1 VKIWDHXNHBXEIH-UHFFFAOYSA-N 0.000 claims abstract 2
- IMZSHOZQEKPUQG-UHFFFAOYSA-N 1-[4-(fluoromethyl)phenyl]-3-(oxan-4-yl)pyrazolo[3,4-c]pyridine Chemical compound C1=CC(CF)=CC=C1N1C2=CN=CC=C2C(C2CCOCC2)=N1 IMZSHOZQEKPUQG-UHFFFAOYSA-N 0.000 claims abstract 2
- ZXMLQCJUWUMPIR-UHFFFAOYSA-N 2-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethanamine Chemical compound C1CN(CCN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 ZXMLQCJUWUMPIR-UHFFFAOYSA-N 0.000 claims abstract 2
- FVFVHHXIBBJAGH-UHFFFAOYSA-N 3-aminopropyl 4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCCCN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 FVFVHHXIBBJAGH-UHFFFAOYSA-N 0.000 claims abstract 2
- GEKJXTBPUZRTGW-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]-n-[3-(dimethylamino)propyl]piperidine-1-carboxamide Chemical compound C1CN(C(=O)NCCCN(C)C)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 GEKJXTBPUZRTGW-UHFFFAOYSA-N 0.000 claims abstract 2
- DHVIHXOUWLISGQ-UHFFFAOYSA-N 4-[1-(4-methylphenyl)pyrrolo[2,3-c]pyridin-3-yl]morpholine Chemical compound C1=CC(C)=CC=C1N1C2=CN=CC=C2C(N2CCOCC2)=C1 DHVIHXOUWLISGQ-UHFFFAOYSA-N 0.000 claims abstract 2
- YZXLJBAURSYRBM-UHFFFAOYSA-N 5-amino-1-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]pentan-1-one Chemical compound C1CN(C(=O)CCCCN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 YZXLJBAURSYRBM-UHFFFAOYSA-N 0.000 claims abstract 2
- AHSBRNLPKIICIU-CQSZACIVSA-N [(3r)-4-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]morpholin-3-yl]methanol Chemical compound OC[C@@H]1COCCN1C(C1=CC=NC=C11)=NN1C1=CC=C(Cl)C=C1 AHSBRNLPKIICIU-CQSZACIVSA-N 0.000 claims abstract 2
- KRGICSYONBDZHH-UHFFFAOYSA-N [1-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]piperidin-2-yl]-piperazin-1-ylmethanone Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(N2C(CCCC2)C(=O)N2CCNCC2)=N1 KRGICSYONBDZHH-UHFFFAOYSA-N 0.000 claims abstract 2
- HYQSSECHZGDUAQ-UHFFFAOYSA-N [4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]-(1,4-diazepan-1-yl)methanone Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCN(CC2)C(=O)N2CCNCCC2)=C1 HYQSSECHZGDUAQ-UHFFFAOYSA-N 0.000 claims abstract 2
- HUUGOXRVWATWEV-UHFFFAOYSA-N [4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCN(CC2)C(=O)N2CCOCC2)=C1 HUUGOXRVWATWEV-UHFFFAOYSA-N 0.000 claims abstract 2
- NMUZEXQMQNXYNZ-UHFFFAOYSA-N [4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]-piperazin-1-ylmethanone Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCN(CC2)C(=O)N2CCNCC2)=C1 NMUZEXQMQNXYNZ-UHFFFAOYSA-N 0.000 claims abstract 2
- CYIDIYZCFGLYSZ-UHFFFAOYSA-N [4-[1-(4-methylphenyl)pyrazolo[3,4-c]pyridin-3-yl]morpholin-2-yl]methanol Chemical compound C1=CC(C)=CC=C1N1C2=CN=CC=C2C(N2CC(CO)OCC2)=N1 CYIDIYZCFGLYSZ-UHFFFAOYSA-N 0.000 claims abstract 2
- NIYSVSJNDYBCLQ-UHFFFAOYSA-N [4-[1-(4-methylphenyl)pyrazolo[3,4-c]pyridin-3-yl]morpholin-3-yl]methanol Chemical compound C1=CC(C)=CC=C1N1C2=CN=CC=C2C(N2C(COCC2)CO)=N1 NIYSVSJNDYBCLQ-UHFFFAOYSA-N 0.000 claims abstract 2
- VHYFPFMABNAQAX-UHFFFAOYSA-N ethyl 1-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(C1=CC=NC=C11)=NN1C1=CC=C(Cl)C=C1 VHYFPFMABNAQAX-UHFFFAOYSA-N 0.000 claims abstract 2
- QZFRUMFTYPYUCY-UHFFFAOYSA-N ethyl 1-[1-(4-methylphenyl)pyrazolo[3,4-c]pyridin-3-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(C1=CC=NC=C11)=NN1C1=CC=C(C)C=C1 QZFRUMFTYPYUCY-UHFFFAOYSA-N 0.000 claims abstract 2
- ZQBOZHVEHAAULJ-UHFFFAOYSA-N methyl 1-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]piperidine-2-carboxylate Chemical compound COC(=O)C1CCCCN1C(C1=CC=NC=C11)=NN1C1=CC=C(Cl)C=C1 ZQBOZHVEHAAULJ-UHFFFAOYSA-N 0.000 claims abstract 2
- QMFMJWRMNUPWJK-UHFFFAOYSA-N methyl 4-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]morpholine-3-carboxylate Chemical compound COC(=O)C1COCCN1C(C1=CC=NC=C11)=NN1C1=CC=C(Cl)C=C1 QMFMJWRMNUPWJK-UHFFFAOYSA-N 0.000 claims abstract 2
- NQEUXJIRFMCWBP-UHFFFAOYSA-N n-(2-aminoethyl)-1-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)NCCN)CCN1C(C1=CC=NC=C11)=NN1C1=CC=C(Cl)C=C1 NQEUXJIRFMCWBP-UHFFFAOYSA-N 0.000 claims abstract 2
- FCJBPNOBATWLGO-UHFFFAOYSA-N n-(2-aminoethyl)-4-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]morpholine-3-carboxamide Chemical compound NCCNC(=O)C1COCCN1C(C1=CC=NC=C11)=NN1C1=CC=C(Cl)C=C1 FCJBPNOBATWLGO-UHFFFAOYSA-N 0.000 claims abstract 2
- KFTVQCDTGBYJBN-UHFFFAOYSA-N n-(2-aminoethyl)-4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidine-1-carboxamide Chemical compound C1CN(C(=O)NCCN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 KFTVQCDTGBYJBN-UHFFFAOYSA-N 0.000 claims abstract 2
- JTVIBBLWPCTTPF-UHFFFAOYSA-N n-(3-aminopropyl)-4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidine-1-carboxamide Chemical compound C1CN(C(=O)NCCCN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 JTVIBBLWPCTTPF-UHFFFAOYSA-N 0.000 claims abstract 2
- QILNKYDVBQWLTA-UHFFFAOYSA-N n-butyl-1-(4-chlorophenyl)-n-methylpyrazolo[3,4-c]pyridin-3-amine Chemical compound C12=CN=CC=C2C(N(C)CCCC)=NN1C1=CC=C(Cl)C=C1 QILNKYDVBQWLTA-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000011282 treatment Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- 208000027866 inflammatory disease Diseases 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 230000004054 inflammatory process Effects 0.000 claims description 11
- 206010061218 Inflammation Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 230000004614 tumor growth Effects 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010047115 Vasculitis Diseases 0.000 claims description 3
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000026278 immune system disease Diseases 0.000 claims description 3
- XIMBESZRBTVIOD-UHFFFAOYSA-N piperidine-2-carboxamide Chemical compound NC(=O)C1CCCCN1 XIMBESZRBTVIOD-UHFFFAOYSA-N 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 208000022309 Alcoholic Liver disease Diseases 0.000 claims description 2
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- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 2
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- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims description 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
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- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
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- 206010039710 Scleroderma Diseases 0.000 claims description 2
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- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 2
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- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 17
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- BKCPIIKZPOOFMV-UHFFFAOYSA-N 1-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]-4-(dimethylamino)butan-1-one Chemical compound C1CN(C(=O)CCCN(C)C)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 BKCPIIKZPOOFMV-UHFFFAOYSA-N 0.000 abstract 1
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- UQPLRGBMLZFBEM-UHFFFAOYSA-N [1-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]piperidin-4-yl]-morpholin-4-ylmethanone Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(N2CCC(CC2)C(=O)N2CCOCC2)=N1 UQPLRGBMLZFBEM-UHFFFAOYSA-N 0.000 abstract 1
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- NYDFDDONODKIFA-UHFFFAOYSA-N n-(2-aminoethyl)-1-[1-(4-chlorophenyl)pyrazolo[3,4-c]pyridin-3-yl]piperidine-2-carboxamide Chemical compound NCCNC(=O)C1CCCCN1C(C1=CC=NC=C11)=NN1C1=CC=C(Cl)C=C1 NYDFDDONODKIFA-UHFFFAOYSA-N 0.000 abstract 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 206010043207 temporal arteritis Diseases 0.000 description 1
- JYUQEWCJWDGCRX-UHFFFAOYSA-N tert-butyl 4-formylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C=O)CC1 JYUQEWCJWDGCRX-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- ACNRTYKOPZDRCO-UHFFFAOYSA-N tert-butyl n-(2-oxoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC=O ACNRTYKOPZDRCO-UHFFFAOYSA-N 0.000 description 1
- POHWAQLZBIMPRN-UHFFFAOYSA-N tert-butyl n-(3-aminopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCN POHWAQLZBIMPRN-UHFFFAOYSA-N 0.000 description 1
- XDJCYKMWJCYQJM-UHFFFAOYSA-N tert-butyl n-(3-hydroxypropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCO XDJCYKMWJCYQJM-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002676 xenobiotic agent Substances 0.000 description 1
- 230000002034 xenobiotic effect Effects 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- 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
-
- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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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
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- 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
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
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- 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
- A61P37/02—Immunomodulators
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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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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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
-
- 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
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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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2011/065967 WO2013037411A1 (en) | 2011-09-14 | 2011-09-14 | New enzyme inhibitor compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2847193A1 true CA2847193A1 (en) | 2013-03-21 |
Family
ID=44677871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2847193A Abandoned CA2847193A1 (en) | 2011-09-14 | 2011-09-14 | New enzyme inhibitor compounds |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9150574B2 (enExample) |
| EP (1) | EP2755974A1 (enExample) |
| JP (1) | JP5796130B2 (enExample) |
| CN (1) | CN103889983B (enExample) |
| AU (1) | AU2011376717A1 (enExample) |
| BR (1) | BR112014005793A2 (enExample) |
| CA (1) | CA2847193A1 (enExample) |
| EA (1) | EA201490451A1 (enExample) |
| IL (1) | IL231353A0 (enExample) |
| IN (1) | IN2014DN01883A (enExample) |
| SG (1) | SG11201400277VA (enExample) |
| WO (1) | WO2013037411A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB201304526D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| GB201304527D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| US20160113893A1 (en) | 2013-06-12 | 2016-04-28 | Proximagen Limited | New therapeutic uses of enzyme inhibitors |
| GB201416446D0 (en) | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New enzyme inhibitor compounds |
| GB201416444D0 (en) | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New compounds |
| GB201507031D0 (en) * | 2015-04-24 | 2015-06-10 | Proximagen Ltd | New pharmaceutical salt forms |
| JP2019502672A (ja) | 2015-12-07 | 2019-01-31 | ベネボレンタイ ケンブリッジ リミティド | 疼痛の治療のためのｖａｐ−１阻害剤 |
| CA3049679A1 (en) * | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Inhibitors of nhe-mediated antiport |
| US20210330646A1 (en) * | 2018-08-27 | 2021-10-28 | Spinogenix, Inc. | Fascin binding compounds for spinogenesis |
| CN113939510A (zh) | 2019-05-29 | 2022-01-14 | 先正达农作物保护股份公司 | 杀微生物衍生物 |
| MX2022007652A (es) | 2019-12-19 | 2022-09-23 | Janssen Pharmaceutica Nv | Derivados espiráncos sustituidos de cadena lineal. |
| JP2023521468A (ja) * | 2020-04-16 | 2023-05-24 | エフ． ホフマン－ラ ロシュ アーゲー | ビフェニル誘導体 |
| AU2022286467A1 (en) | 2021-06-01 | 2024-01-25 | Janssen Pharmaceutica Nv | SUBSTITUTED PHENYL-1H-PYRROLO[2, 3-c]PYRIDINE DERIVATIVES |
| WO2023193790A1 (en) * | 2022-04-08 | 2023-10-12 | Janssen Pharmaceutica Nv | Crystalline forms of an inhibitor of the menin/mll interaction |
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| US6143749A (en) | 1995-06-07 | 2000-11-07 | Abbott Laboratories | Heterocyclic substituted cyclopentane compounds |
| DE19649460A1 (de) | 1996-11-26 | 1998-05-28 | Bayer Ag | Neue substituierte Pyrazolderivate |
| EE200200134A (et) | 1999-09-14 | 2003-04-15 | Aventis Pharmaceuticals Inc. | D4 retseptori antagonistidena toimivad bensisoksasolüül-, püridoisoksasolüül- ja benstienüülfenoksüderivaadid |
| AU2002214505A1 (en) | 2000-11-09 | 2002-05-21 | Biovitrum Ab | New use of 4, 5, 6, 7-tetrahydroimidazo-(4,5-c)pyridine derivatives |
| US6982286B2 (en) | 2001-07-12 | 2006-01-03 | Biotie Therapies Corp. | Carbocyclic hydrazino inhibitors of copper-containing amine oxidases |
| DE60228103D1 (de) | 2001-10-02 | 2008-09-18 | Smithkline Beecham Corp | Chemische verbindungen |
| US7456169B2 (en) | 2003-02-27 | 2008-11-25 | Abbott Laboratories Inc. | Heterocyclic kinase inhibitors |
| US20050096360A1 (en) | 2003-08-08 | 2005-05-05 | Salter-Cid Luisa M. | Inhibitors of semicarbazide-sensitive amine oxidase (SSAO) and VAP-1 mediated adhesion useful for treatment of diseases |
| AU2004283196B2 (en) | 2003-09-17 | 2011-08-25 | Janssen Pharmaceutica, N.V. | Fused heterocyclic compounds |
| CA2553724A1 (en) | 2004-02-03 | 2005-08-18 | Abbott Laboratories | Aminobenzoxazoles as therapeutic agents |
| TW200538453A (en) | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| CA2605738C (en) | 2005-04-25 | 2013-10-01 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Novel azaheterocyclic compounds as kinase inhibitors |
| ES2543714T3 (es) | 2005-06-22 | 2015-08-21 | Chemocentryx, Inc. | Compuestos de azaindazol y métodos de uso |
| EP2004166A2 (en) | 2006-03-31 | 2008-12-24 | La Jolla Pharmaceutical Company | Inhibitors of semicarbazide-sensitive amine oxidase (ssao) and vap-1 mediated adhesion useful for treatment and prevention of diseases |
| KR101084635B1 (ko) | 2006-04-04 | 2011-11-18 | 피브로겐, 인크. | Ｈｉｆ 조절제로서 피롤로- 및 티아졸로-피리딘 화합물 |
| GB0610242D0 (en) | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
| WO2008088744A1 (en) | 2007-01-17 | 2008-07-24 | Merck & Co., Inc. | Decahydroquinoline analogs as cb2 receptor modulators |
| CA2683821A1 (en) | 2007-05-02 | 2008-11-13 | Novartis Ag | Heterocyclic compounds and their use as pesticides |
| GB0725103D0 (en) | 2007-12-21 | 2008-01-30 | Glaxo Group Ltd | Novel compounds |
| MX2010007661A (es) | 2008-01-31 | 2010-08-03 | Sanofi Aventis | Azaindol-3-carboxamidas ciclicas, su preparacion y su uso como productos farmaceuticos. |
| WO2009108551A2 (en) | 2008-02-25 | 2009-09-03 | H. Lundbeck A/S | Heteroaryl amide analogues |
| JP5613671B2 (ja) * | 2008-09-16 | 2014-10-29 | プロキシマジェン エルティーディーＰｒｏｘｉｍａｇｅｎ Ｌｔｄ． | 新規化合物ｉｉ |
| BRPI0918602B8 (pt) | 2008-09-16 | 2021-05-25 | Benevolentai Cambridge Ltd | inibidores da atividade de ssao, seu uso, e formulação farmacêutica |
| ES2403633T3 (es) * | 2008-12-04 | 2013-05-20 | Proximagen Limited | Compuestos de imidazopiridina |
| JP2012211085A (ja) | 2009-08-12 | 2012-11-01 | Kyowa Hakko Kirin Co Ltd | ヘッジホッグシグナル阻害剤 |
| GB201004311D0 (en) * | 2010-03-15 | 2010-04-28 | Proximagen Ltd | New enzyme inhibitor compounds |
| GB201115853D0 (en) | 2011-09-14 | 2011-10-26 | Proximagen Ltd | New enzyme inhibitor compounds |
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2011
- 2011-09-14 IN IN1883DEN2014 patent/IN2014DN01883A/en unknown
- 2011-09-14 EA EA201490451A patent/EA201490451A1/ru unknown
- 2011-09-14 BR BR112014005793A patent/BR112014005793A2/pt not_active IP Right Cessation
- 2011-09-14 WO PCT/EP2011/065967 patent/WO2013037411A1/en not_active Ceased
- 2011-09-14 CA CA2847193A patent/CA2847193A1/en not_active Abandoned
- 2011-09-14 CN CN201180073402.9A patent/CN103889983B/zh not_active Expired - Fee Related
- 2011-09-14 SG SG11201400277VA patent/SG11201400277VA/en unknown
- 2011-09-14 US US14/344,417 patent/US9150574B2/en not_active Expired - Fee Related
- 2011-09-14 AU AU2011376717A patent/AU2011376717A1/en not_active Abandoned
- 2011-09-14 JP JP2014530103A patent/JP5796130B2/ja not_active Expired - Fee Related
- 2011-09-14 EP EP11761040.2A patent/EP2755974A1/en not_active Withdrawn
-
2014
- 2014-03-06 IL IL231353A patent/IL231353A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP5796130B2 (ja) | 2015-10-21 |
| US9150574B2 (en) | 2015-10-06 |
| BR112014005793A2 (pt) | 2017-03-28 |
| SG11201400277VA (en) | 2014-05-29 |
| WO2013037411A1 (en) | 2013-03-21 |
| JP2015502913A (ja) | 2015-01-29 |
| IL231353A0 (en) | 2014-04-30 |
| US20140357623A1 (en) | 2014-12-04 |
| EP2755974A1 (en) | 2014-07-23 |
| CN103889983A (zh) | 2014-06-25 |
| CN103889983B (zh) | 2015-12-09 |
| AU2011376717A1 (en) | 2014-03-20 |
| IN2014DN01883A (enExample) | 2015-05-15 |
| EA201490451A1 (ru) | 2014-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140630 |
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| FZDE | Discontinued |
Effective date: 20170206 |