HRP20120069T1 - Derivati 5,6-bisaril-2-piridinkarboksamida, njihovo dobivanje i njihova upotreba u terapiji kao antagonista receptora urotenzina ii - Google Patents
Derivati 5,6-bisaril-2-piridinkarboksamida, njihovo dobivanje i njihova upotreba u terapiji kao antagonista receptora urotenzina ii Download PDFInfo
- Publication number
- HRP20120069T1 HRP20120069T1 HR20120069T HRP20120069T HRP20120069T1 HR P20120069 T1 HRP20120069 T1 HR P20120069T1 HR 20120069 T HR20120069 T HR 20120069T HR P20120069 T HRP20120069 T HR P20120069T HR P20120069 T1 HRP20120069 T1 HR P20120069T1
- Authority
- HR
- Croatia
- Prior art keywords
- chloro
- group
- phenyl
- propoxy
- dimethylamino
- Prior art date
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- 239000005557 antagonist Substances 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 32
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 16
- 125000005843 halogen group Chemical group 0.000 claims abstract 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 9
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims abstract 8
- 125000003118 aryl group Chemical group 0.000 claims abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract 6
- 239000002253 acid Substances 0.000 claims abstract 6
- 239000000203 mixture Substances 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 125000002560 nitrile group Chemical group 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 3
- 125000003367 polycyclic group Chemical group 0.000 claims abstract 3
- 125000006169 tetracyclic group Chemical group 0.000 claims abstract 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 2
- 125000005157 alkyl carboxy group Chemical group 0.000 claims abstract 2
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 2
- -1 3,5-dichloro-2'-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3'-bipyridin-6'-yl Chemical group 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
- BAXZKZFRFMTGND-NDEPHWFRSA-N 6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-n-[(3s)-1-(methanesulfonamido)-4,4-dimethyl-1-oxopentan-3-yl]-5-(2-methylphenyl)pyridine-2-carboxamide Chemical compound C1=C(Cl)C(OCCCN(C)C)=CC(C=2C(=CC=C(N=2)C(=O)N[C@@H](CC(=O)NS(C)(=O)=O)C(C)(C)C)C=2C(=CC=CC=2)C)=C1 BAXZKZFRFMTGND-NDEPHWFRSA-N 0.000 claims 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 2
- 208000033626 Renal failure acute Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 201000011040 acute kidney failure Diseases 0.000 claims 2
- 208000020832 chronic kidney disease Diseases 0.000 claims 2
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- DJWJGQCLTSKMMV-MHZLTWQESA-N methyl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-chlorophenyl)pyridine-2-carbonyl]amino]-4,4-dimethylpentanoate Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)OC)C(C)(C)C)=CC=C1C1=CC=CC=C1Cl DJWJGQCLTSKMMV-MHZLTWQESA-N 0.000 claims 2
- BOIAYGWUCUEYFJ-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methylphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=CC=CC=2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 BOIAYGWUCUEYFJ-UHFFFAOYSA-N 0.000 claims 2
- BAENFYZNFQZTRT-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(3-chloro-5-methylpyridin-2-yl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=CC(C)=CN=2)Cl)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 BAENFYZNFQZTRT-UHFFFAOYSA-N 0.000 claims 2
- QCMBRUMUMHKQFA-PMERELPUSA-N 2-methoxyethyl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methylphenyl)pyridine-2-carbonyl]amino]-4,4-dimethylpentanoate Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)OCCOC)C(C)(C)C)=CC=C1C1=CC=CC=C1C QCMBRUMUMHKQFA-PMERELPUSA-N 0.000 claims 1
- LMNCCSLTFTWHLW-NDEPHWFRSA-N 6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-n-[(2s)-1-cyano-3,3-dimethylbutan-2-yl]-5-(2-methylphenyl)pyridine-2-carboxamide Chemical compound C1=C(Cl)C(OCCCN(C)C)=CC(C=2C(=CC=C(N=2)C(=O)N[C@@H](CC#N)C(C)(C)C)C=2C(=CC=CC=2)C)=C1 LMNCCSLTFTWHLW-NDEPHWFRSA-N 0.000 claims 1
- DQJWXAAKPLMCQR-HKBQPEDESA-N 6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-n-[(3s)-1-[cyclopropyl(methyl)amino]-4,4-dimethyl-1-oxopentan-3-yl]-5-(2-methylphenyl)pyridine-2-carboxamide Chemical compound C1=C(Cl)C(OCCCN(C)C)=CC(C=2C(=CC=C(N=2)C(=O)N[C@@H](CC(=O)N(C)C2CC2)C(C)(C)C)C=2C(=CC=CC=2)C)=C1 DQJWXAAKPLMCQR-HKBQPEDESA-N 0.000 claims 1
- WHTFBVAAHUZXBC-NDEPHWFRSA-N 6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-n-[(3s)-4,4-dimethyl-1-(methylamino)-1-oxopentan-3-yl]-5-(2-methylphenyl)pyridine-2-carboxamide Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)NC)C(C)(C)C)=CC=C1C1=CC=CC=C1C WHTFBVAAHUZXBC-NDEPHWFRSA-N 0.000 claims 1
- KGKKPRGIRJKOPH-NDEPHWFRSA-N 6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-n-[(3s)-4,4-dimethyl-1-oxo-1-(2,2,2-trifluoroethylamino)pentan-3-yl]-5-(2-methylphenyl)pyridine-2-carboxamide Chemical compound C1=C(Cl)C(OCCCN(C)C)=CC(C=2C(=CC=C(N=2)C(=O)N[C@@H](CC(=O)NCC(F)(F)F)C(C)(C)C)C=2C(=CC=CC=2)C)=C1 KGKKPRGIRJKOPH-NDEPHWFRSA-N 0.000 claims 1
- 206010002329 Aneurysm Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010028594 Myocardial fibrosis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 1
- 206010047700 Vomiting Diseases 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- VZOGSWSQBOCHGX-LJAQVGFWSA-N ethyl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methylphenyl)pyridine-2-carbonyl]amino]-4,4-dimethylpentanoate Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)OCC)C(C)(C)C)=CC=C1C1=CC=CC=C1C VZOGSWSQBOCHGX-LJAQVGFWSA-N 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- CXNFIZJKLQYAEW-LJAQVGFWSA-N methyl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2,4-dimethylphenyl)pyridine-2-carbonyl]amino]-4,4-dimethylpentanoate Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)OC)C(C)(C)C)=CC=C1C1=CC=C(C)C=C1C CXNFIZJKLQYAEW-LJAQVGFWSA-N 0.000 claims 1
- DZLURQFCFPGHBI-MHZLTWQESA-N methyl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-chloro-5-ethoxyphenyl)pyrazine-2-carbonyl]amino]-4,4-dimethylpentanoate Chemical compound CCOC1=CC=C(Cl)C(C=2C(=NC(=CN=2)C(=O)N[C@@H](CC(=O)OC)C(C)(C)C)C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=C1 DZLURQFCFPGHBI-MHZLTWQESA-N 0.000 claims 1
- LQWDAVMQOOYQEY-MHZLTWQESA-N methyl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-chloro-5-methylphenyl)pyridine-2-carbonyl]amino]-4-methylpentanoate Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)OC)C(C)C)=CC=C1C1=CC(C)=CC=C1Cl LQWDAVMQOOYQEY-MHZLTWQESA-N 0.000 claims 1
- RYLSNPMHHYIUMC-NDEPHWFRSA-N methyl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methylphenyl)pyridine-2-carbonyl]amino]-4,4-dimethylpentanoate Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)OC)C(C)(C)C)=CC=C1C1=CC=CC=C1C RYLSNPMHHYIUMC-NDEPHWFRSA-N 0.000 claims 1
- YTNZSVSTXYCBJQ-VWLOTQADSA-N methyl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(3-chloro-5-fluoropyridin-2-yl)pyridine-2-carbonyl]amino]-4,4-dimethylpentanoate Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)OC)C(C)(C)C)=CC=C1C1=NC=C(F)C=C1Cl YTNZSVSTXYCBJQ-VWLOTQADSA-N 0.000 claims 1
- VSHUQBKBVNQGCN-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2,4-dimethylphenyl)pyrazine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1N=C(C=2C(=CC(C)=CC=2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 VSHUQBKBVNQGCN-UHFFFAOYSA-N 0.000 claims 1
- KJQXSVZJOWHVKF-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-chloro-5-ethoxyphenyl)pyrazine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound CCOC1=CC=C(Cl)C(C=2C(=NC(=CN=2)C(=O)NC2(CCCCC2)C(=O)OC)C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=C1 KJQXSVZJOWHVKF-UHFFFAOYSA-N 0.000 claims 1
- OSOMGSXSKDRXPU-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-chloro-5-propoxyphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound CCCOC1=CC=C(Cl)C(C=2C(=NC(=CC=2)C(=O)NC2(CCCCC2)C(=O)OC)C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=C1 OSOMGSXSKDRXPU-UHFFFAOYSA-N 0.000 claims 1
- ZEWGFADWUNJNAF-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methyl-5-propan-2-yloxyphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=CC=C(OC(C)C)C=2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 ZEWGFADWUNJNAF-UHFFFAOYSA-N 0.000 claims 1
- HYDGGAWCGZDIFE-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methylpyridin-3-yl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=NC=CC=2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 HYDGGAWCGZDIFE-UHFFFAOYSA-N 0.000 claims 1
- MVXZNVGDDSXRMU-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(3,5-diethylpyrazol-1-yl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound N1=C(CC)C=C(CC)N1C1=CC=C(C(=O)NC2(CCCCC2)C(=O)OC)N=C1C1=CC=C(Cl)C(OCCCN(C)C)=C1 MVXZNVGDDSXRMU-UHFFFAOYSA-N 0.000 claims 1
- JFVOHGJURGRKQD-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(3,5-dimethylpyrazol-1-yl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(N2C(=CC(C)=N2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 JFVOHGJURGRKQD-UHFFFAOYSA-N 0.000 claims 1
- PFQDSQGWSSATFV-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(3-chloro-5-fluoropyridin-2-yl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=CC(F)=CN=2)Cl)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 PFQDSQGWSSATFV-UHFFFAOYSA-N 0.000 claims 1
- GOSAFRMQMWSBCU-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(3-hydroxy-2-methylphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=C(O)C=CC=2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 GOSAFRMQMWSBCU-UHFFFAOYSA-N 0.000 claims 1
- DZNWAALYLMVDCD-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(4-hydroxy-2-methylphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=CC(O)=CC=2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 DZNWAALYLMVDCD-UHFFFAOYSA-N 0.000 claims 1
- NHSZNKKBCZNTMH-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(5-cyclopropyl-2-methylphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=CC=C(C=2)C2CC2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 NHSZNKKBCZNTMH-UHFFFAOYSA-N 0.000 claims 1
- HFKCOAPKHHLJTC-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(5-ethoxy-2-methylphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound CCOC1=CC=C(C)C(C=2C(=NC(=CC=2)C(=O)NC2(CCCCC2)C(=O)OC)C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=C1 HFKCOAPKHHLJTC-UHFFFAOYSA-N 0.000 claims 1
- FVYZNNQMHZMTDK-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(5-hydroxy-2-methylphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=CC=C(O)C=2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 FVYZNNQMHZMTDK-UHFFFAOYSA-N 0.000 claims 1
- JDFJNCXVJAYDBZ-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(6-methyl-1,3-benzodioxol-5-yl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound C=1C=C(C=2C(=CC=3OCOC=3C=2)C)C(C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=NC=1C(=O)NC1(C(=O)OC)CCCCC1 JDFJNCXVJAYDBZ-UHFFFAOYSA-N 0.000 claims 1
- RUJLGPPLPMFLEI-UHFFFAOYSA-N methyl 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-[5-(2-methoxyethoxy)-2-methylphenyl]pyridine-2-carbonyl]amino]cyclohexane-1-carboxylate Chemical compound COCCOC1=CC=C(C)C(C=2C(=NC(=CC=2)C(=O)NC2(CCCCC2)C(=O)OC)C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=C1 RUJLGPPLPMFLEI-UHFFFAOYSA-N 0.000 claims 1
- JGPMARFOHRRUJL-UHFFFAOYSA-N methyl 2-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-chlorophenyl)pyridine-2-carbonyl]amino]adamantane-2-carboxylate Chemical compound C1C2CC(C3)CC1CC3C2(C(=O)OC)NC(=O)C(N=C1C=2C=C(OCCCN(C)C)C(Cl)=CC=2)=CC=C1C1=CC=CC=C1Cl JGPMARFOHRRUJL-UHFFFAOYSA-N 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- PGLALAWBCZPHGZ-MHZLTWQESA-N n-[(3s)-1-amino-4,4-dimethyl-1-oxopentan-3-yl]-6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methylphenyl)pyridine-2-carboxamide Chemical compound C1=C(Cl)C(OCCCN(C)C)=CC(C=2C(=CC=C(N=2)C(=O)N[C@@H](CC(N)=O)C(C)(C)C)C=2C(=CC=CC=2)C)=C1 PGLALAWBCZPHGZ-MHZLTWQESA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 208000007232 portal hypertension Diseases 0.000 claims 1
- JDZFJAZQKCKPRB-PMERELPUSA-N propan-2-yl (3s)-3-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methylphenyl)pyridine-2-carbonyl]amino]-4,4-dimethylpentanoate Chemical compound C=1C=C(Cl)C(OCCCN(C)C)=CC=1C1=NC(C(=O)N[C@@H](CC(=O)OC(C)C)C(C)(C)C)=CC=C1C1=CC=CC=C1C JDZFJAZQKCKPRB-PMERELPUSA-N 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 208000037905 systemic hypertension Diseases 0.000 claims 1
- 230000008673 vomiting Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0800651A FR2927330B1 (fr) | 2008-02-07 | 2008-02-07 | Derives de 5,6-bisaryl-2-pyridine-carboxamide, leur preparation et leur application en therapeutique comme antagonistes des recepteurs a l'urotensine ii |
PCT/FR2009/000128 WO2009115665A1 (fr) | 2008-02-07 | 2009-02-05 | Dérivés de 5.6-bisaryl-2-pyr1dine-carboxamide, leur préparatio leur application en thérapeutique comme antagonistes des recepteurs a l'urotensine ii |
Publications (1)
Publication Number | Publication Date |
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HRP20120069T1 true HRP20120069T1 (hr) | 2012-02-29 |
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HR20120069T HRP20120069T1 (hr) | 2008-02-07 | 2012-01-23 | Derivati 5,6-bisaril-2-piridinkarboksamida, njihovo dobivanje i njihova upotreba u terapiji kao antagonista receptora urotenzina ii |
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US (2) | US8466292B2 (pl) |
EP (1) | EP2238110B1 (pl) |
JP (1) | JP2011511046A (pl) |
KR (1) | KR20100116183A (pl) |
CN (1) | CN101981008B (pl) |
AR (1) | AR070573A1 (pl) |
AT (1) | ATE530527T1 (pl) |
AU (1) | AU2009227091B2 (pl) |
BR (1) | BRPI0907719A2 (pl) |
CA (1) | CA2715096A1 (pl) |
CY (1) | CY1112670T1 (pl) |
DK (1) | DK2238110T3 (pl) |
ES (1) | ES2375339T3 (pl) |
FR (1) | FR2927330B1 (pl) |
HR (1) | HRP20120069T1 (pl) |
IL (1) | IL207356A0 (pl) |
MX (1) | MX2010008713A (pl) |
PL (1) | PL2238110T3 (pl) |
PT (1) | PT2238110E (pl) |
RU (1) | RU2497808C2 (pl) |
SI (1) | SI2238110T1 (pl) |
WO (1) | WO2009115665A1 (pl) |
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US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
WO2014055955A1 (en) * | 2012-10-05 | 2014-04-10 | Rigel Pharmaceuticals, Inc. | Gdf-8 inhibitors |
AU2014369982B2 (en) | 2013-12-24 | 2019-04-18 | Bristol-Myers Squibb Company | Tricyclic compounds as anticancer agents |
PT3778595T (pt) | 2015-02-27 | 2021-11-09 | Calcimedica Inc | Tratamento de pancreatite |
EP3294736B1 (en) | 2015-05-11 | 2020-07-22 | Bristol-Myers Squibb Company | Tricyclic compounds as anticancer agents |
CN108137597A (zh) | 2015-07-28 | 2018-06-08 | 百时美施贵宝公司 | TGFβ受体拮抗剂 |
DK3331525T3 (da) * | 2015-08-07 | 2020-12-14 | Calcimedica Inc | Anvendelse af CRAC-kanal-inhibitorer til behandling af slagtilfælde og traumatisk hjerneskade |
US20180250303A1 (en) | 2015-08-25 | 2018-09-06 | Bristol-Myers Squibb Company | Tgf beta receptor antagonists |
CN116327924A (zh) | 2015-11-23 | 2023-06-27 | 戊瑞治疗有限公司 | 用于癌症治疗的单独fgfr2抑制剂或与免疫刺激剂的组合 |
SG10201913033UA (en) | 2016-03-04 | 2020-03-30 | Bristol Myers Squibb Co | Combination therapy with anti-cd73 antibodies |
AU2020253633A1 (en) | 2019-04-05 | 2021-11-04 | Kymera Therapeutics, Inc. | STAT degraders and uses thereof |
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SE0100902D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
SE0104332D0 (sv) * | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
EP1610753A4 (en) * | 2003-02-20 | 2007-07-04 | Encysive Pharmaceuticals Inc | UROTENSIN-II RECEPTOR ANTAGONISTS OF PHENYLENEDIAMINE AND ANTAGONISTS OF CCR-9 |
JP2006519258A (ja) * | 2003-02-28 | 2006-08-24 | エンサイシブ・ファーマシューティカルズ・インコーポレイテッド | ピリジン、ピリミジン、キノリン、キナゾリンおよびナフタレン系のウロテンシン−ii受容体拮抗薬 |
FR2856684B1 (fr) * | 2003-06-26 | 2008-04-11 | Sanofi Synthelabo | Derives de diphenylpyridine, leur preparation et leur application en therapeutique |
FR2904827B1 (fr) * | 2006-08-11 | 2008-09-19 | Sanofi Aventis Sa | Derives de 5,6-bisaryl-2-pyridine-carboxamide, leur preparation et leur application en therapeutique comme antiganistes des recepteurs a l'urotensine ii |
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Also Published As
Publication number | Publication date |
---|---|
KR20100116183A (ko) | 2010-10-29 |
RU2497808C2 (ru) | 2013-11-10 |
ES2375339T3 (es) | 2012-02-29 |
JP2011511046A (ja) | 2011-04-07 |
FR2927330B1 (fr) | 2010-02-19 |
CN101981008A (zh) | 2011-02-23 |
MX2010008713A (es) | 2010-09-09 |
IL207356A0 (en) | 2010-12-30 |
US20130252974A1 (en) | 2013-09-26 |
BRPI0907719A2 (pt) | 2015-07-14 |
AR070573A1 (es) | 2010-04-21 |
US20110009426A1 (en) | 2011-01-13 |
EP2238110A1 (fr) | 2010-10-13 |
CA2715096A1 (fr) | 2009-09-24 |
CY1112670T1 (el) | 2016-02-10 |
US8653276B2 (en) | 2014-02-18 |
AU2009227091A1 (en) | 2009-09-24 |
RU2010137115A (ru) | 2012-03-20 |
DK2238110T3 (da) | 2012-02-20 |
PL2238110T3 (pl) | 2012-03-30 |
US8466292B2 (en) | 2013-06-18 |
CN101981008B (zh) | 2013-07-31 |
ATE530527T1 (de) | 2011-11-15 |
PT2238110E (pt) | 2012-01-02 |
FR2927330A1 (fr) | 2009-08-14 |
EP2238110B1 (fr) | 2011-10-26 |
WO2009115665A1 (fr) | 2009-09-24 |
SI2238110T1 (sl) | 2012-02-29 |
AU2009227091B2 (en) | 2013-05-23 |
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