LV11615B - Therapeutic amides - Google Patents
Therapeutic amides Download PDFInfo
- Publication number
- LV11615B LV11615B LVP-96-176A LV960176A LV11615B LV 11615 B LV11615 B LV 11615B LV 960176 A LV960176 A LV 960176A LV 11615 B LV11615 B LV 11615B
- Authority
- LV
- Latvia
- Prior art keywords
- carboxylic acid
- biphenyl
- trifluoromethyl
- trifluoromethylbiphenyl
- tetrahydroisoquinolin
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims description 13
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 175
- -1 cyano, nitro, oxo, thioxo, aminosulfonyl Chemical group 0.000 claims description 127
- IQOMYCGTGFGDFN-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 IQOMYCGTGFGDFN-UHFFFAOYSA-N 0.000 claims description 75
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 16
- 201000001320 Atherosclerosis Diseases 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 230000028327 secretion Effects 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 208000008589 Obesity Diseases 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 235000020824 obesity Nutrition 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 101150102415 Apob gene Proteins 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- 206010033645 Pancreatitis Diseases 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- XOYOWXXIKWPXFC-UHFFFAOYSA-N n-(1,2,3,4-tetrahydroisoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CNCC2)C2=C1 XOYOWXXIKWPXFC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 229940124530 sulfonamide Drugs 0.000 claims description 8
- 150000003456 sulfonamides Chemical class 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 101710095342 Apolipoprotein B Proteins 0.000 claims description 6
- 102100040202 Apolipoprotein B-100 Human genes 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 6
- 229920001774 Perfluoroether Polymers 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- SYBKBPXOVQYFFA-UHFFFAOYSA-N 2-[2-(hydroxymethyl)-5-nitrophenyl]ethanol Chemical compound OCCC1=CC([N+]([O-])=O)=CC=C1CO SYBKBPXOVQYFFA-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 5
- XGJYPBLLKVZMKG-UHFFFAOYSA-N n-[2-(1h-imidazol-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2NC=CN=2)CC2)C2=C1 XGJYPBLLKVZMKG-UHFFFAOYSA-N 0.000 claims description 5
- 150000003585 thioureas Chemical class 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- GHVZCYSYXCFJMA-OAQYLSRUSA-N n-[(1r)-1-phenylethyl]-6-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)N(CC1=CC=2)CCC1=CC=2NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 GHVZCYSYXCFJMA-OAQYLSRUSA-N 0.000 claims description 4
- LBBXOYBEGXAARL-UHFFFAOYSA-N n-[2-(1,3-thiazol-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2SC=CN=2)CC2)C2=C1 LBBXOYBEGXAARL-UHFFFAOYSA-N 0.000 claims description 4
- WXIVOQCTQSVGAQ-UHFFFAOYSA-N n-[2-(2-thiophen-2-ylacetyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)CC=3SC=CC=3)C2=C1 WXIVOQCTQSVGAQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- OLOIFCYZWOTWRO-UHFFFAOYSA-N tert-butyl 6-amino-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound NC1=CC=C2CN(C(=O)OC(C)(C)C)CCC2=C1 OLOIFCYZWOTWRO-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- POXYSHFMRRORKX-UHFFFAOYSA-N 2-[5-amino-2-(hydroxymethyl)phenyl]ethanol Chemical compound NC1=CC=C(CO)C(CCO)=C1 POXYSHFMRRORKX-UHFFFAOYSA-N 0.000 claims description 3
- IZFQSQQGQRFVHN-UHFFFAOYSA-N N-[2-(cyclobutanecarbonyl)-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)C3CCC3)C2=C1 IZFQSQQGQRFVHN-UHFFFAOYSA-N 0.000 claims description 3
- RHBRVEGJYKKIKU-UHFFFAOYSA-N N-[2-(thiophen-3-ylmethyl)-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2=CSC=C2)CC2)C2=C1 RHBRVEGJYKKIKU-UHFFFAOYSA-N 0.000 claims description 3
- ARENAIUNOSZMET-UHFFFAOYSA-N N-[2-[(1-methylimidazol-2-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound CN1C(=NC=C1)CN1CC2=CC=C(C=C2CC1)NC(=O)C=1C(=CC=CC1)C1=CC=C(C=C1)C(F)(F)F ARENAIUNOSZMET-UHFFFAOYSA-N 0.000 claims description 3
- OEQHRWKPSZZHTI-UHFFFAOYSA-N N-[2-[(2,5-dimethoxyoxolan-3-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound COC1OC(OC)CC1CN1CC2=CC=C(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)C=C2CC1 OEQHRWKPSZZHTI-UHFFFAOYSA-N 0.000 claims description 3
- HMVQKDXKSNGJMV-UHFFFAOYSA-N N-[2-[(3-chlorophenyl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2C=C(Cl)C=CC=2)CC2)C2=C1 HMVQKDXKSNGJMV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- CUNBFJSOUZFOIJ-UHFFFAOYSA-N n-(2-but-3-enoyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)CC=C)C2=C1 CUNBFJSOUZFOIJ-UHFFFAOYSA-N 0.000 claims description 3
- WNDIAFXQKOHFLV-UHFFFAOYSA-N n-[2-(1h-1,2,4-triazol-5-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2=NNC=N2)CC2)C2=C1 WNDIAFXQKOHFLV-UHFFFAOYSA-N 0.000 claims description 3
- OWUTUOOOSSLKAT-UHFFFAOYSA-N n-[2-(3-methylbutanoyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(C(=O)CC(C)C)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 OWUTUOOOSSLKAT-UHFFFAOYSA-N 0.000 claims description 3
- GYPJVCGKIBMXFE-UHFFFAOYSA-N n-[3-(2-hydroxyethyl)-4-(hydroxymethyl)phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(CO)C(CCO)=CC(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 GYPJVCGKIBMXFE-UHFFFAOYSA-N 0.000 claims description 3
- BQBWUBKROPEBDY-UHFFFAOYSA-N n-benzyl-6-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)NCC=3C=CC=CC=3)C2=C1 BQBWUBKROPEBDY-UHFFFAOYSA-N 0.000 claims description 3
- AKMALXRXYAFPLL-UHFFFAOYSA-N tert-butyl 6-nitro-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2CN(C(=O)OC(C)(C)C)CCC2=C1 AKMALXRXYAFPLL-UHFFFAOYSA-N 0.000 claims description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 3
- AEFLZMREMMKHDV-UHFFFAOYSA-N 1-(6-amino-3,4-dihydro-1H-isoquinolin-2-yl)-2-thiophen-2-ylethanone Chemical compound C1CC2=CC(N)=CC=C2CN1C(=O)CC1=CC=CS1 AEFLZMREMMKHDV-UHFFFAOYSA-N 0.000 claims description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 2
- UALJVGZBTOOZQQ-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]-n-[2-[(2,6,6-trimethylcyclohex-2-en-1-yl)methyl]-3,4-dihydro-1h-isoquinolin-6-yl]benzamide Chemical compound CC1=CCCC(C)(C)C1CN1CC2=CC=C(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)C=C2CC1 UALJVGZBTOOZQQ-UHFFFAOYSA-N 0.000 claims description 2
- SUSWILMGRZSTML-UHFFFAOYSA-N 6-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]-3,4-dihydro-1h-isoquinoline-2-carboxylic acid Chemical compound C=1C=C2CN(C(=O)O)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 SUSWILMGRZSTML-UHFFFAOYSA-N 0.000 claims description 2
- AVEJPRXCBCHUEY-UHFFFAOYSA-N N-(2-propan-2-ylsulfonyl-3,4-dihydro-1H-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(S(=O)(=O)C(C)C)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 AVEJPRXCBCHUEY-UHFFFAOYSA-N 0.000 claims description 2
- SYEMZMFSQHRZPE-UHFFFAOYSA-N N-[2-(pyrimidin-2-ylmethyl)-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2N=CC=CN=2)CC2)C2=C1 SYEMZMFSQHRZPE-UHFFFAOYSA-N 0.000 claims description 2
- HTQLPGBGOMIIOQ-UHFFFAOYSA-N N-[2-[(2,4-dichlorophenyl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2C(=CC(Cl)=CC=2)Cl)CC2)C2=C1 HTQLPGBGOMIIOQ-UHFFFAOYSA-N 0.000 claims description 2
- ITJYVAJPJUJZOO-UHFFFAOYSA-N n-(2-benzyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2C=CC=CC=2)CC2)C2=C1 ITJYVAJPJUJZOO-UHFFFAOYSA-N 0.000 claims description 2
- RONNIDMEEXKTTP-UHFFFAOYSA-N n-(2-butanoyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(C(=O)CCC)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 RONNIDMEEXKTTP-UHFFFAOYSA-N 0.000 claims description 2
- JHWRGYDZUYBPRO-UHFFFAOYSA-N n-(2-pentanoyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(C(=O)CCCC)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 JHWRGYDZUYBPRO-UHFFFAOYSA-N 0.000 claims description 2
- OUIYGDVVLCXGIH-UHFFFAOYSA-N n-[2-(1h-benzimidazol-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2NC3=CC=CC=C3N=2)CC2)C2=C1 OUIYGDVVLCXGIH-UHFFFAOYSA-N 0.000 claims description 2
- KEDZZOLFYJSFTQ-UHFFFAOYSA-N n-[2-(1h-pyrrol-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2NC=CC=2)CC2)C2=C1 KEDZZOLFYJSFTQ-UHFFFAOYSA-N 0.000 claims description 2
- YSUQGHLKNKSWBD-UHFFFAOYSA-N n-[2-(dimethylsulfamoyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(S(=O)(=O)N(C)C)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 YSUQGHLKNKSWBD-UHFFFAOYSA-N 0.000 claims description 2
- RHQOWPBOKMMPTG-UHFFFAOYSA-N n-hexyl-6-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C=1C=C2CN(C(=O)NCCCCCC)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 RHQOWPBOKMMPTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001391 thioamide group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- KCVKPKPNJUSQCH-UHFFFAOYSA-N 2-(1,3-thiazol-2-ylmethyl)-3,4-dihydro-1H-isoquinolin-6-amine 2-[4-(trifluoromethyl)phenyl]benzoic acid Chemical compound NC1=CC=C(CN(CC2=NC=CS2)CC2)C2=C1.OC(C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1)=O KCVKPKPNJUSQCH-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- BXSOJVFGOJGNNF-UHFFFAOYSA-N 6-amino-N-cyclopropyl-3,4-dihydro-1H-isoquinoline-2-carbothioamide Chemical compound C1CC2=CC(N)=CC=C2CN1C(=S)NC1CC1 BXSOJVFGOJGNNF-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- SNEPJCYFHNDGSB-UHFFFAOYSA-N FC(OC1=C(C=CC=C1)S(=O)(=O)N1CC2=CC=C(C=C2CC1)N)(F)F.FC(C1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)O)(F)F Chemical compound FC(OC1=C(C=CC=C1)S(=O)(=O)N1CC2=CC=C(C=C2CC1)N)(F)F.FC(C1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)O)(F)F SNEPJCYFHNDGSB-UHFFFAOYSA-N 0.000 claims 1
- UYZFYOYAIBCODV-UHFFFAOYSA-N OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1.C1=CC=CC2=NC(CN3CC4=CC=C(C=C4CC3)N)=CC=C21 Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1.C1=CC=CC2=NC(CN3CC4=CC=C(C=C4CC3)N)=CC=C21 UYZFYOYAIBCODV-UHFFFAOYSA-N 0.000 claims 1
- JMXKSJTWWOQHRL-UHFFFAOYSA-N S1C(=CC=C1)CC(=O)N1CC2=CC=C(C=C2CC1)N.FC(C1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)O)(F)F Chemical compound S1C(=CC=C1)CC(=O)N1CC2=CC=C(C=C2CC1)N.FC(C1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)O)(F)F JMXKSJTWWOQHRL-UHFFFAOYSA-N 0.000 claims 1
- SRPMZCMLLWOMKK-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(CN2CC3=CC=C(C=C3CC2)N)C=CC1.FC(C1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)O)(F)F Chemical compound [N+](=O)([O-])C=1C=C(CN2CC3=CC=C(C=C3CC2)N)C=CC1.FC(C1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)O)(F)F SRPMZCMLLWOMKK-UHFFFAOYSA-N 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 239000003524 antilipemic agent Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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
- C07D401/10—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 linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- C07D405/02—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
- C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IB1995/000448 WO1996040640A1 (en) | 1995-06-07 | 1995-06-07 | BIPHENYL-2-CARBOXYLIC ACID-TETRAHYDRO-ISOQUINOLIN-6-YL AMIDE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF MICROSOMAL TRIGLYCERIDE TRANSFER PROTEIN AND/OR APOLIPOPROTEIN B (Apo B) SECRETION |
CA002223574A CA2223574C (en) | 1995-06-07 | 1995-06-07 | Biphenyl-2-carboxylic acid-tetrahydro-isoquinolin-6-yl amide derivatives, their preparation and their use as inhibitors of microsomal triglyceride transfer protein and/or apolipoprotein b (apo b) secretion |
HU9601566A HUP9601566A3 (en) | 1995-06-07 | 1996-06-06 | Therapeutic tetrahydro-isoquinolin derivatives, their intermediates and pharmaceutical compositions containing the active component |
Publications (2)
Publication Number | Publication Date |
---|---|
LV11615A LV11615A (lv) | 1996-12-20 |
LV11615B true LV11615B (en) | 1997-04-20 |
Family
ID=89994037
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LVP-96-176A LV11615B (en) | 1995-06-07 | 1996-06-06 | Therapeutic amides |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0832069B1 (fi) |
AP (1) | AP9600804A0 (fi) |
BR (1) | BR9602628A (fi) |
CZ (1) | CZ289249B6 (fi) |
FI (1) | FI974440A (fi) |
HR (1) | HRP960270A2 (fi) |
HU (1) | HUP9601566A3 (fi) |
IL (1) | IL118484A (fi) |
LV (1) | LV11615B (fi) |
NZ (1) | NZ286733A (fi) |
PL (1) | PL314636A1 (fi) |
SG (1) | SG44952A1 (fi) |
SI (1) | SI9600183A (fi) |
WO (1) | WO1996040640A1 (fi) |
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PL328094A1 (en) * | 1996-01-16 | 1999-01-04 | Bristol Myers Squibb Co | Conformingly restricted aromatic inhibitors triglycerides carrying chromosome protein and method of obtaining such inhibitors |
WO1997041111A1 (en) * | 1996-04-30 | 1997-11-06 | Pfizer Inc. | Processes and intermediates for preparing 4'-trifluoromethylbiphenyl-2-carboxylic acid [2-(2h-[1,2,4]triazol-3-ylmethyl)-1,2,3,4-tetrahydro-isoquinolin-6-yl]-amide |
US5827875A (en) * | 1996-05-10 | 1998-10-27 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
US5885983A (en) * | 1996-05-10 | 1999-03-23 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
TW438796B (en) * | 1996-05-15 | 2001-06-07 | Hoffmann La Roche | 2,4-diaminopyrimidine derivatives, the manufacture process thereof, and the antibiotically-active pharmaceutical composition containing the same |
US5883109A (en) * | 1996-07-24 | 1999-03-16 | Bristol-Myers Squibb Company | Method for lowering serum lipid levels employing an MTP inhibitor in combination with another cholesterol lowering drug |
WO1998023593A1 (en) * | 1996-11-27 | 1998-06-04 | Pfizer Inc. | Apo b-secretion/mtp inhibitory amides |
US5760246A (en) | 1996-12-17 | 1998-06-02 | Biller; Scott A. | Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method |
CN1252792A (zh) * | 1997-04-18 | 2000-05-10 | 辉瑞大药厂 | 制备4'-三氟甲基-联苯基-2-羧酸(1,2,3,4-四氢-异喹啉-6-基)酰胺的方法和中间体 |
GB9708119D0 (en) * | 1997-04-22 | 1997-06-11 | Glaxo Group Ltd | Chemical compounds |
US5968950A (en) * | 1997-06-23 | 1999-10-19 | Pfizer Inc | Apo B-secretion/MTP inhibitor hydrochloride salt |
EP1085846A2 (en) | 1998-06-08 | 2001-03-28 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
US6197798B1 (en) | 1998-07-21 | 2001-03-06 | Novartis Ag | Amino-benzocycloalkane derivatives |
CO5090829A1 (es) * | 1998-07-21 | 2001-10-30 | Novartis Ag | Compuestos organicos de la formula i, utiles como inhibido res de la proteina de transferencia de triglicerido microso mal y de la secrecion de la apolipoproteina b. |
GB9826412D0 (en) | 1998-12-03 | 1999-01-27 | Glaxo Group Ltd | Chemical compounds |
WO2001005767A1 (en) * | 1999-07-20 | 2001-01-25 | Novartis Ag | Organic compounds |
CA2324801A1 (en) * | 1999-11-10 | 2001-05-10 | Andrew Gordon Swick | Use of apo b secretion/mtp inhibitors and anti-obesity agents |
IL139450A0 (en) * | 1999-11-10 | 2001-11-25 | Pfizer Prod Inc | Methods of administering apo b-secretion/mtp inhibitors |
CA2324800A1 (en) * | 1999-11-10 | 2001-05-10 | Mary Anne Hickman | Use of apo b secretion/mtp inhibitors |
CO5271688A1 (es) * | 1999-11-10 | 2003-04-30 | Pfizer Prod Inc | Uso de inhibidor de secrecion de apoliproteinas b y/o de proteina de transferencia de trigliceridos microsmales |
AU2001262185A1 (en) * | 2000-04-10 | 2001-10-23 | Novartis Ag | Substituted (hetero)aryl carboxamide derivatives as microsomal triglyceride transfer protein (mtp) and apolipoprotein b (apo b) secretion |
GB0013383D0 (en) * | 2000-06-01 | 2000-07-26 | Glaxo Group Ltd | Therapeutic benzamide derivatives |
GB0013346D0 (en) * | 2000-06-01 | 2000-07-26 | Glaxo Group Ltd | Therapeutic benzamide derivatives |
DE10033337A1 (de) * | 2000-07-08 | 2002-01-17 | Boehringer Ingelheim Pharma | Biphenylcarbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
WO2002014277A1 (fr) * | 2000-08-10 | 2002-02-21 | Tanabe Seiyaku Co., Ltd. | Composes de biphenylcarboxamidoisoindoline, procedes de preparation de ceux-ci et produits intermediaires destines a la synthese de ceux-ci |
AU2001277727A1 (en) * | 2000-08-10 | 2002-02-25 | Tanabe Seiyaku Co., Ltd. | Benzoylaminoisoindoline compounds, processes for the preparation of the same andintermediates for the synthesis thereof |
JO2654B1 (en) | 2000-09-04 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Multiple aryl caroxa amides are useful as lipid - lowering agents |
EP1326835A1 (en) * | 2000-10-05 | 2003-07-16 | Fujisawa Pharmaceutical Co., Ltd. | Benzamide compounds as apo b secretion inhibitors |
JO2409B1 (en) | 2000-11-21 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Second-phenyl carboxy amides are useful as lipid-lowering agents |
JO2390B1 (en) * | 2001-04-06 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Diphenylcarboxamides act as lipid-lowering agents |
US20040157866A1 (en) * | 2001-04-30 | 2004-08-12 | Hisashi Takasugi | Amide compounds |
CN1522246B (zh) * | 2001-06-28 | 2010-04-21 | 辉瑞产品公司 | 三酰胺取代的吲哚、苯并呋喃及苯并噻吩 |
US20050038035A1 (en) * | 2001-11-28 | 2005-02-17 | Hisashi Takasugi | Heterocyclic amide compounds as apolipoprotein b inhibitors |
GB0129013D0 (en) * | 2001-12-04 | 2002-01-23 | Glaxo Group Ltd | Compounds |
GB0129015D0 (en) * | 2001-12-04 | 2002-01-23 | Glaxo Group Ltd | Compounds |
EP2033953A1 (en) * | 2002-02-15 | 2009-03-11 | Glaxo Group Limited | Vanilloid receptor modulators |
NZ531890A (en) | 2002-02-28 | 2006-02-24 | Japan Tobacco Inc | Ester compound and medicinal use thereof |
WO2004039795A2 (en) * | 2002-10-29 | 2004-05-13 | Fujisawa Pharmaceutical Co., Ltd. | Amide compounds for the treatment of hyperlipidemia |
CN1826121B (zh) * | 2003-07-23 | 2013-05-29 | 幸讬制药公司 | 苯基与吡啶基衍生物用于制备调控钙离子释放活化钙离子通道的药物的用途 |
EP1669345A4 (en) | 2003-08-29 | 2008-02-20 | Japan Tobacco Inc | ESTER DERIVATIVE AND MEDICAL USE THEREOF |
GB2406856B (en) * | 2003-10-07 | 2005-10-19 | Renovis Inc | Amide compounds as ion channel ligands and uses thereof |
GB2413129A (en) * | 2003-10-07 | 2005-10-19 | Renovis Inc | Aromatic amide compounds as ion channel ligands and uses thereof |
EP1716137A1 (en) | 2004-02-04 | 2006-11-02 | Pfizer Products Incorporated | Substituted quinoline compounds |
KR20060129082A (ko) | 2004-03-05 | 2006-12-14 | 더 트러스티스 오브 더 유니버시티 오브 펜실바니아 | 부작용을 최소화하면서 과지질혈증 및 과콜레스테롤혈증과연관된 질환 또는 질병의 치료 방법 |
US8101774B2 (en) | 2004-10-18 | 2012-01-24 | Japan Tobacco Inc. | Ester derivatives and medicinal use thereof |
JP2006249022A (ja) | 2005-03-11 | 2006-09-21 | Sumitomo Chemical Co Ltd | 4−(2−メチルフェニル)ベンゾトリフルオライドの製造方法 |
MX2007013133A (es) | 2005-04-19 | 2008-03-14 | Surface Logix Inc | Inhibidores de la proteina microsomal de transferencia de trigliceridos de la secrecion de apo-b. |
US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
DE102005062987A1 (de) * | 2005-12-28 | 2007-07-05 | Grünenthal GmbH | Substituierte Propiolsäureamide und ihre Verwendung zur Herstellung von Arzneimitteln |
US8383660B2 (en) | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
US7919506B2 (en) | 2006-03-10 | 2011-04-05 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
DK2046787T3 (da) | 2006-08-01 | 2011-07-18 | Glaxo Group Ltd | Pyrazolo[3,4-B]pyridin-forbindelser, og deres anvendelse som PDE4-inhibitorer |
JO2653B1 (en) | 2006-10-24 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Tetrahydroflavin 1-carboxylic acid substituted with pyridine or pyrazine inhibit MTB |
CN101528671B (zh) | 2006-10-24 | 2013-03-13 | 詹森药业有限公司 | 抑制mtp的四氢-萘-1-羧酸衍生物 |
JP5498168B2 (ja) | 2006-12-01 | 2014-05-21 | ブリストル−マイヤーズ スクイブ カンパニー | アテローム性動脈硬化および循環器疾患の治療のためのcetp阻害剤としてのn−((3−ベンジル)−2,2−(ビス−フェニル)−プロパン−1−アミン誘導体 |
EP2986599A1 (en) | 2013-04-17 | 2016-02-24 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
BR112021013807A2 (pt) | 2019-01-18 | 2021-11-30 | Astrazeneca Ab | Inibidores de pcsk9 e seus métodos de uso |
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Publication number | Priority date | Publication date | Assignee | Title |
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US4022900A (en) * | 1970-09-09 | 1977-05-10 | Marion Laboratories, Inc. | Compositions containing 1,2,3,4-tetrahydroisoquinolines used as hypotensive agents |
CA1248536A (en) * | 1982-09-10 | 1989-01-10 | Wellcome Foundation Limited (The) | Benzoil acid derivatives |
US5595872A (en) * | 1992-03-06 | 1997-01-21 | Bristol-Myers Squibb Company | Nucleic acids encoding microsomal trigyceride transfer protein |
IL110172A (en) * | 1993-07-22 | 2001-10-31 | Lilly Co Eli | Bicycle compounds and pharmaceuticals containing them |
-
1995
- 1995-06-07 EP EP95918722A patent/EP0832069B1/en not_active Expired - Lifetime
- 1995-06-07 WO PCT/IB1995/000448 patent/WO1996040640A1/en active IP Right Grant
-
1996
- 1996-05-09 AP APAP/P/1996/000804A patent/AP9600804A0/en unknown
- 1996-05-30 IL IL11848496A patent/IL118484A/en not_active IP Right Cessation
- 1996-06-04 BR BR9602628A patent/BR9602628A/pt not_active Application Discontinuation
- 1996-06-05 PL PL96314636A patent/PL314636A1/xx unknown
- 1996-06-05 NZ NZ286733A patent/NZ286733A/en unknown
- 1996-06-05 SG SG1996009974A patent/SG44952A1/en unknown
- 1996-06-06 HR HRPCT/IB95/00448A patent/HRP960270A2/hr not_active Application Discontinuation
- 1996-06-06 SI SI9600183A patent/SI9600183A/sl not_active IP Right Cessation
- 1996-06-06 CZ CZ19961644A patent/CZ289249B6/cs not_active IP Right Cessation
- 1996-06-06 HU HU9601566A patent/HUP9601566A3/hu unknown
- 1996-06-06 LV LVP-96-176A patent/LV11615B/en unknown
-
1997
- 1997-12-05 FI FI974440A patent/FI974440A/fi not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
CZ289249B6 (cs) | 2001-12-12 |
FI974440A0 (fi) | 1997-12-05 |
IL118484A0 (en) | 1996-09-12 |
NZ286733A (en) | 1998-02-26 |
EP0832069B1 (en) | 2003-03-05 |
LV11615A (lv) | 1996-12-20 |
HRP960270A2 (en) | 1997-12-31 |
IL118484A (en) | 2001-11-25 |
AP9600804A0 (en) | 1997-11-09 |
BR9602628A (pt) | 1998-09-08 |
EP0832069A1 (en) | 1998-04-01 |
SG44952A1 (en) | 1997-12-19 |
SI9600183A (en) | 1997-04-30 |
CZ164496A3 (en) | 1997-01-15 |
WO1996040640A1 (en) | 1996-12-19 |
HUP9601566A2 (en) | 1997-09-29 |
HUP9601566A3 (en) | 1998-01-28 |
FI974440A (fi) | 1998-01-27 |
PL314636A1 (en) | 1996-12-09 |
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