HRP970425A2 - Substituted pyridines and biphenyls - Google Patents
Substituted pyridines and biphenylsInfo
- Publication number
- HRP970425A2 HRP970425A2 HR08/690,111A HRP970425A HRP970425A2 HR P970425 A2 HRP970425 A2 HR P970425A2 HR P970425 A HRP970425 A HR P970425A HR P970425 A2 HRP970425 A2 HR P970425A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- substituted
- phenyl
- diisopropyl
- alkenyl
- Prior art date
Links
- 150000003222 pyridines Chemical class 0.000 title claims description 38
- 235000010290 biphenyl Nutrition 0.000 title description 11
- 150000004074 biphenyls Chemical class 0.000 title description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 327
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 255
- 125000004432 carbon atom Chemical group C* 0.000 claims description 201
- 150000001875 compounds Chemical class 0.000 claims description 174
- 125000000217 alkyl group Chemical group 0.000 claims description 136
- -1 hydroxy, mercapto Chemical class 0.000 claims description 134
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 123
- 229910052736 halogen Inorganic materials 0.000 claims description 115
- 150000002367 halogens Chemical class 0.000 claims description 115
- 125000001424 substituent group Chemical group 0.000 claims description 114
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 125000001624 naphthyl group Chemical group 0.000 claims description 82
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 74
- 125000003545 alkoxy group Chemical group 0.000 claims description 68
- 238000011282 treatment Methods 0.000 claims description 67
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 64
- 125000004076 pyridyl group Chemical group 0.000 claims description 60
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 56
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 55
- 239000000460 chlorine Substances 0.000 claims description 55
- 229910052801 chlorine Inorganic materials 0.000 claims description 55
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 54
- 239000011737 fluorine Substances 0.000 claims description 49
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 41
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 40
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 39
- 230000009467 reduction Effects 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 34
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 31
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims description 30
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims description 30
- 125000002252 acyl group Chemical group 0.000 claims description 30
- 102000051325 Glucagon Human genes 0.000 claims description 27
- 108060003199 Glucagon Proteins 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims description 27
- 229960004666 glucagon Drugs 0.000 claims description 27
- 239000012442 inert solvent Substances 0.000 claims description 27
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 25
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 25
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
- 206010012601 diabetes mellitus Diseases 0.000 claims description 24
- 125000002541 furyl group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 230000002829 reductive effect Effects 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 239000003153 chemical reaction reagent Substances 0.000 claims description 21
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 21
- 125000001544 thienyl group Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 230000001404 mediated effect Effects 0.000 claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 16
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 15
- 210000004369 blood Anatomy 0.000 claims description 15
- 239000008280 blood Substances 0.000 claims description 15
- 239000008103 glucose Substances 0.000 claims description 15
- 229940127557 pharmaceutical product Drugs 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- 238000009472 formulation Methods 0.000 claims description 14
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 14
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000001425 triazolyl group Chemical group 0.000 claims description 13
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000005493 quinolyl group Chemical group 0.000 claims description 12
- 229940122904 Glucagon receptor antagonist Drugs 0.000 claims description 11
- NIDVFKIOOJTTCI-UHFFFAOYSA-N [4-(4-fluorophenyl)-5-pentyl-2,6-di(propan-2-yl)pyridin-3-yl]methanol Chemical compound CCCCCC1=C(C(C)C)N=C(C(C)C)C(CO)=C1C1=CC=C(F)C=C1 NIDVFKIOOJTTCI-UHFFFAOYSA-N 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000001041 indolyl group Chemical group 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000000335 thiazolyl group Chemical group 0.000 claims description 11
- 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 9
- 238000007239 Wittig reaction Methods 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 238000001212 derivatisation Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 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 5
- 238000007796 conventional method Methods 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 230000027455 binding Effects 0.000 claims description 4
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims description 4
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 claims description 4
- 238000003747 Grignard reaction Methods 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000000660 7-membered heterocyclic compounds Chemical class 0.000 claims description 2
- 229910003849 O-Si Inorganic materials 0.000 claims description 2
- 229910003872 O—Si Inorganic materials 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 230000001225 therapeutic effect Effects 0.000 claims 2
- GHBDKPMSPLDASO-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-3-[(4-fluorophenyl)sulfanylmethyl]-4,6-di(propan-2-yl)phenyl]ethanol Chemical group C=1C=C(F)C=CC=1SCC=1C(C(C)C)=CC(C(C)C)=C(C(C)O)C=1C1=CC=C(Cl)C=C1 GHBDKPMSPLDASO-UHFFFAOYSA-N 0.000 claims 1
- MZVCXBXHXDZABD-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-3-[(4-methylphenyl)sulfanylmethyl]-4,6-di(propan-2-yl)phenyl]ethanol Chemical group C=1C=C(C)C=CC=1SCC=1C(C(C)C)=CC(C(C)C)=C(C(C)O)C=1C1=CC=C(Cl)C=C1 MZVCXBXHXDZABD-UHFFFAOYSA-N 0.000 claims 1
- WSNAAEJBQBMDJE-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-3-ethyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(Cl)C=C1 WSNAAEJBQBMDJE-UHFFFAOYSA-N 0.000 claims 1
- RORLGXLMGNHHRB-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-3-hexyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(Cl)C=C1 RORLGXLMGNHHRB-UHFFFAOYSA-N 0.000 claims 1
- FDZAGJMNNJBGGF-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-3-pentyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(Cl)C=C1 FDZAGJMNNJBGGF-UHFFFAOYSA-N 0.000 claims 1
- IILZAAMYOKNOKR-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-4,6-di(propan-2-yl)-3-propylphenyl]ethanol Chemical group CCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(Cl)C=C1 IILZAAMYOKNOKR-UHFFFAOYSA-N 0.000 claims 1
- HLEVBPXHLDHNJZ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-3-[(4-fluorophenyl)sulfanylmethyl]-4,6-di(propan-2-yl)phenyl]ethanol Chemical group C=1C=C(F)C=CC=1SCC=1C(C(C)C)=CC(C(C)C)=C(C(C)O)C=1C1=CC=C(F)C=C1 HLEVBPXHLDHNJZ-UHFFFAOYSA-N 0.000 claims 1
- POHZADCXBDUAAI-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-3-[(4-methylphenyl)sulfanylmethyl]-4,6-di(propan-2-yl)phenyl]ethanol Chemical group C=1C=C(C)C=CC=1SCC=1C(C(C)C)=CC(C(C)C)=C(C(C)O)C=1C1=CC=C(F)C=C1 POHZADCXBDUAAI-UHFFFAOYSA-N 0.000 claims 1
- QZSWVMMECMZFLW-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-3-hexyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(F)C=C1 QZSWVMMECMZFLW-UHFFFAOYSA-N 0.000 claims 1
- VNZRUAGGCIAOJQ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-3-pentyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(F)C=C1 VNZRUAGGCIAOJQ-UHFFFAOYSA-N 0.000 claims 1
- VDTWKXAPIQBOMO-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-4,6-di(propan-2-yl)-3-propylphenyl]ethanol Chemical group CCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(F)C=C1 VDTWKXAPIQBOMO-UHFFFAOYSA-N 0.000 claims 1
- VPKLOZUZMAZBBV-UHFFFAOYSA-N 1-[2-(4-methylphenyl)-3-[(4-methylphenyl)sulfanylmethyl]-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CC(C)C1=CC(C(C)C)=C(C(C)O)C(C=2C=CC(C)=CC=2)=C1CSC1=CC=C(C)C=C1 VPKLOZUZMAZBBV-UHFFFAOYSA-N 0.000 claims 1
- ODXUPAJABSMZTK-UHFFFAOYSA-N 1-[2-(4-methylphenyl)-3-pentyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(C)C=C1 ODXUPAJABSMZTK-UHFFFAOYSA-N 0.000 claims 1
- RQDKDEMGDDRPCY-UHFFFAOYSA-N 1-[2-(4-methylphenyl)-4,6-di(propan-2-yl)-3-propylphenyl]ethanol Chemical group CCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(C)C=C1 RQDKDEMGDDRPCY-UHFFFAOYSA-N 0.000 claims 1
- NYNHEIHSNJLCHP-UHFFFAOYSA-N 1-[2-phenyl-4,6-di(propan-2-yl)-3-propylphenyl]ethanol Chemical group CCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=CC=C1 NYNHEIHSNJLCHP-UHFFFAOYSA-N 0.000 claims 1
- BLEHINJATHSHDE-UHFFFAOYSA-N 1-[3-[(4-fluorophenyl)sulfanylmethyl]-2-(4-methylphenyl)-4,6-di(propan-2-yl)phenyl]ethanol Chemical group C=1C=C(F)C=CC=1SCC=1C(C(C)C)=CC(C(C)C)=C(C(C)O)C=1C1=CC=C(C)C=C1 BLEHINJATHSHDE-UHFFFAOYSA-N 0.000 claims 1
- WMGAMKYNHNFTIG-UHFFFAOYSA-N 1-[3-[(4-fluorophenyl)sulfanylmethyl]-2-phenyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group C=1C=C(F)C=CC=1SCC=1C(C(C)C)=CC(C(C)C)=C(C(C)O)C=1C1=CC=CC=C1 WMGAMKYNHNFTIG-UHFFFAOYSA-N 0.000 claims 1
- QFUSNTBKZNNNCQ-UHFFFAOYSA-N 1-[3-[(4-methylphenyl)sulfanylmethyl]-2-phenyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CC(C)C1=CC(C(C)C)=C(C(C)O)C(C=2C=CC=CC=2)=C1CSC1=CC=C(C)C=C1 QFUSNTBKZNNNCQ-UHFFFAOYSA-N 0.000 claims 1
- PZWWHLZVCXOIGG-UHFFFAOYSA-N 1-[3-butyl-2-(4-chlorophenyl)-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(Cl)C=C1 PZWWHLZVCXOIGG-UHFFFAOYSA-N 0.000 claims 1
- HGCYYLIYSGIJKE-UHFFFAOYSA-N 1-[3-butyl-2-(4-fluorophenyl)-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(F)C=C1 HGCYYLIYSGIJKE-UHFFFAOYSA-N 0.000 claims 1
- JNDQCAVDIVEFIY-UHFFFAOYSA-N 1-[3-butyl-2-(4-methylphenyl)-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(C)C=C1 JNDQCAVDIVEFIY-UHFFFAOYSA-N 0.000 claims 1
- QVJRSJJPQAICMZ-UHFFFAOYSA-N 1-[3-butyl-2-phenyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=CC=C1 QVJRSJJPQAICMZ-UHFFFAOYSA-N 0.000 claims 1
- QGAVOQLRNNHPOG-UHFFFAOYSA-N 1-[3-ethyl-2-(4-fluorophenyl)-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(F)C=C1 QGAVOQLRNNHPOG-UHFFFAOYSA-N 0.000 claims 1
- FYGICTMUJWLPCA-UHFFFAOYSA-N 1-[3-ethyl-2-(4-methylphenyl)-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(C)C=C1 FYGICTMUJWLPCA-UHFFFAOYSA-N 0.000 claims 1
- HTOIKIOVMJVPFB-UHFFFAOYSA-N 1-[3-ethyl-2-phenyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=CC=C1 HTOIKIOVMJVPFB-UHFFFAOYSA-N 0.000 claims 1
- VSZDPPCYYXLWCS-UHFFFAOYSA-N 1-[3-hexyl-2-(4-methylphenyl)-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(C)C=C1 VSZDPPCYYXLWCS-UHFFFAOYSA-N 0.000 claims 1
- WMKBBDODMCTVQS-UHFFFAOYSA-N 1-[3-hexyl-2-phenyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=CC=C1 WMKBBDODMCTVQS-UHFFFAOYSA-N 0.000 claims 1
- LKJUIYNUZVVUAE-UHFFFAOYSA-N 1-[3-pentyl-2-phenyl-4,6-di(propan-2-yl)phenyl]ethanol Chemical group CCCCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=CC=C1 LKJUIYNUZVVUAE-UHFFFAOYSA-N 0.000 claims 1
- ODKIEVZPQGGRJL-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2,6-di(propan-2-yl)-5-propylpyridin-3-yl]ethanol Chemical compound CCCC1=C(C(C)C)N=C(C(C)C)C(C(C)O)=C1C1=CC=C(Cl)C=C1 ODKIEVZPQGGRJL-UHFFFAOYSA-N 0.000 claims 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 150000004672 propanoic acids Chemical class 0.000 description 1
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- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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- LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 1
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
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- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
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Classifications
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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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
- A61P3/06—Antihyperlipidemics
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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
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US6613942B1 (en) | 1997-07-01 | 2003-09-02 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
US6605624B1 (en) | 1998-02-13 | 2003-08-12 | Pharmacia Corporation | Substituted pyridines useful for inhibiting cholesteryl ester transfer protein activity |
PT1112275E (pt) | 1998-09-09 | 2003-12-31 | Metabasis Therapeutics Inc | Novos inibidores heteroaromaticos da frutose-1,6-bisfosfatase |
US7919109B2 (en) | 1999-02-08 | 2011-04-05 | Intarcia Therapeutics, Inc. | Stable non-aqueous single phase viscous vehicles and formulations utilizing such vehicles |
US7258869B1 (en) | 1999-02-08 | 2007-08-21 | Alza Corporation | Stable non-aqueous single phase viscous vehicles and formulations utilizing such vehicle |
US6503949B1 (en) | 1999-05-17 | 2003-01-07 | Noro Nordisk A/S | Glucagon antagonists/inverse agonists |
DE60124861T2 (de) | 2000-01-21 | 2007-05-10 | Novartis Ag | Zusammensetzungen bestehend aus dipeptidylpeptidase-iv inhibitoren und antidiabetica |
US6562807B2 (en) | 2000-06-23 | 2003-05-13 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
ME01311B (me) * | 2000-07-14 | 2013-12-20 | Hoffmann La Roche | N-oksidi kao proljekovi 4-fenil-piridinskih derivata koji su antagonisti nki receptora |
US7115279B2 (en) | 2000-08-03 | 2006-10-03 | Curatolo William J | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
US6706744B2 (en) | 2000-11-17 | 2004-03-16 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
AU2002223500A1 (en) | 2000-11-17 | 2002-05-27 | Novo-Nordisk A/S | Glucagon antagonists/inverse agonists |
US6821960B2 (en) | 2000-11-17 | 2004-11-23 | Noyo Nordisk Pharmaceuticals, Inc. | Glucagon antagonists/inverse agonists |
EP1935885A3 (en) * | 2001-05-22 | 2008-10-15 | Neurogen Corporation | Melanin concentrating hormone receptor ligands : substituted 1-benzyl-4-aryl piperazine analogues. |
BR0209932A (pt) | 2001-05-22 | 2004-10-13 | Neurogen Corp | Composto ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica, preparação farmacêutica embalada, métodos para modular ligação de mch a um receptor de mch e de mvc, para alterar a atividade de transdução de sinal de um receptor de mch em uma célula, para tratar uma doença ou distúrbio associado com a ativação de receptor de mch patogênico obesidade e para determinar a presença ou ausência de receptor de mch em uma amostra, e, uso de um composto |
ATE444060T1 (de) | 2001-06-22 | 2009-10-15 | Pfizer Prod Inc | Pharmazeutische zusammensetzungen enthaltend dispersionen aus arzneistoffen und neutralen polymeren |
OA12625A (en) | 2001-06-22 | 2006-06-12 | Pfizer Prod Inc | Pharmaceutical compositions of adsorbates of amorphous drug. |
UA74912C2 (en) | 2001-07-06 | 2006-02-15 | Merck & Co Inc | Beta-aminotetrahydroimidazo-(1,2-a)-pyrazines and tetratriazolo-(4,3-a)-pyrazines as inhibitors of dipeptylpeptidase for the treatment or prevention of diabetes |
US6740776B2 (en) | 2001-07-16 | 2004-05-25 | Novartis Ag | Air oxidation of an aromatic aldehyde to an aromatic acid |
US6881746B2 (en) | 2001-12-03 | 2005-04-19 | Novo Nordick A/S | Glucagon antagonists/inverse agonists |
WO2003053359A2 (en) | 2001-12-19 | 2003-07-03 | Atherogenics, Inc. | 1,3-bis-(substituted-phenyl)-2-propyn-1-ones and their use to treat disorders |
RU2004121898A (ru) | 2001-12-19 | 2006-01-20 | Атеродженикс, Инк. (Us) | Производные халкона и их применение для лечения заболеваний |
AR038375A1 (es) | 2002-02-01 | 2005-01-12 | Pfizer Prod Inc | Composiciones farmaceuticas de inhibidores de la proteina de transferencia de esteres de colesterilo |
DE60320940D1 (de) | 2002-02-01 | 2008-06-26 | Pfizer Prod Inc | Pharmazeutische zusammensetzungen amorpher dispersionen von wirkstoffen und lipophiler mikrophasenbildender materialien |
RU2293078C2 (ru) | 2002-08-30 | 2007-02-10 | Джапан Тобакко Инк. | Соединения дибензиламина, фармацевтическая композиция и терапевтический или профилактический агент на их основе, способ лечения или профилактики гиперлипидемии или артериосклероза |
US7196106B2 (en) | 2002-11-05 | 2007-03-27 | Merck & Co., Inc | Cyanothiophene derivatives, compositions containing such compounds and methods of use |
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DE3905908A1 (de) | 1989-02-25 | 1990-09-06 | Bayer Ag | Substituierte chinoline, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
DE3909378A1 (de) | 1989-03-22 | 1990-09-27 | Bayer Ag | Substituierte biphenyle |
DE3911064A1 (de) | 1989-04-06 | 1990-10-11 | Bayer Ag | Substituierte 1,8-naphthyridine |
US5145959A (en) | 1989-07-18 | 1992-09-08 | Bayer Aktiengesellschaft | Substituted pyrido (2,3-d) pyrimidines as intermediates |
US5183897A (en) | 1989-08-03 | 1993-02-02 | Bayer Aktiengesellschaft | Certain intermediate imino-substituted pyridines |
US5072023A (en) | 1990-02-15 | 1991-12-10 | E. R. Squibb & Sons, Inc. | Process for preparing highly substituted phenyls |
ZA911046B (en) * | 1990-02-26 | 1992-10-28 | Squibb & Sons Inc | Quinoline and pyridine anchors for hmg-coa reductase inhibitors |
DE4022414A1 (de) | 1990-07-13 | 1992-01-16 | Bayer Ag | Substituierte pyrrolo-pyridine |
DE4023308A1 (de) | 1990-07-21 | 1992-01-23 | Bayer Ag | Substituierte pyrido-oxazine |
DE4244029A1 (de) * | 1992-12-24 | 1994-06-30 | Bayer Ag | Neue substituierte Pyridine |
EP0742208A1 (en) * | 1995-05-05 | 1996-11-13 | Grelan Pharmaceutical Co., Ltd. | 2-Ureido-benzamide derivatives |
DE19610932A1 (de) * | 1996-03-20 | 1997-09-25 | Bayer Ag | 2-Aryl-substituierte Pyridine |
-
1997
- 1997-07-28 AR ARP970103411A patent/AR008789A1/es unknown
- 1997-07-29 TR TR1999/02325T patent/TR199902325T2/xx unknown
- 1997-07-29 JP JP50906898A patent/JP2001512416A/ja not_active Ceased
- 1997-07-29 TW TW086110851A patent/TW520360B/zh not_active IP Right Cessation
- 1997-07-29 ZA ZA9706730A patent/ZA976730B/xx unknown
- 1997-07-29 TR TR1999/00163T patent/TR199900163T2/xx unknown
- 1997-07-29 NZ NZ333951A patent/NZ333951A/xx unknown
- 1997-07-29 AU AU38971/97A patent/AU3897197A/en not_active Abandoned
- 1997-07-29 CO CO97043316A patent/CO4900061A1/es unknown
- 1997-07-29 RU RU99104527/04A patent/RU2195443C2/ru not_active IP Right Cessation
- 1997-07-29 EP EP97936259A patent/EP0934274A1/en not_active Withdrawn
- 1997-07-29 HU HU0100324A patent/HUP0100324A3/hu unknown
- 1997-07-29 CN CN97198258A patent/CN1239474A/zh active Pending
- 1997-07-29 WO PCT/US1997/013248 patent/WO1998004528A2/en not_active Application Discontinuation
- 1997-07-29 CA CA002262434A patent/CA2262434A1/en not_active Abandoned
- 1997-07-29 IL IL12825197A patent/IL128251A0/xx unknown
- 1997-07-29 BR BR9710637-2A patent/BR9710637A/pt not_active IP Right Cessation
- 1997-07-29 PL PL97333465A patent/PL333465A1/xx unknown
- 1997-07-29 TR TR1999/02326T patent/TR199902326T2/xx unknown
- 1997-07-29 CZ CZ99308A patent/CZ30899A3/cs unknown
- 1997-07-29 HR HR08/690,111A patent/HRP970425A2/hr not_active Application Discontinuation
- 1997-07-29 KR KR1019997000826A patent/KR20000029723A/ko not_active Application Discontinuation
- 1997-07-31 US US08/904,119 patent/US6218431B1/en not_active Expired - Fee Related
- 1997-07-31 ID IDP972662A patent/ID19422A/id unknown
-
1999
- 1999-01-28 NO NO19990399A patent/NO314143B1/no not_active IP Right Cessation
- 1999-02-23 BG BG103200A patent/BG103200A/xx unknown
-
2002
- 2002-11-11 AR ARP020104321A patent/AR037300A2/es unknown
Also Published As
Publication number | Publication date |
---|---|
US6218431B1 (en) | 2001-04-17 |
KR20000029723A (ko) | 2000-05-25 |
WO1998004528A3 (en) | 1999-11-11 |
NO314143B1 (no) | 2003-02-03 |
CN1239474A (zh) | 1999-12-22 |
NO990399D0 (no) | 1999-01-28 |
JP2001512416A (ja) | 2001-08-21 |
TR199902325T2 (xx) | 2000-02-21 |
CA2262434A1 (en) | 1998-02-05 |
WO1998004528A2 (en) | 1998-02-05 |
BR9710637A (pt) | 2000-10-31 |
EP0934274A1 (en) | 1999-08-11 |
AU3897197A (en) | 1998-02-20 |
CO4900061A1 (es) | 2000-03-27 |
AR037300A2 (es) | 2004-11-03 |
CZ30899A3 (cs) | 1999-05-12 |
BG103200A (en) | 1999-11-30 |
PL333465A1 (en) | 1999-12-20 |
TR199900163T2 (xx) | 1999-04-21 |
NO990399L (no) | 1999-03-29 |
ID19422A (id) | 1998-07-09 |
AR008789A1 (es) | 2000-02-23 |
RU2195443C2 (ru) | 2002-12-27 |
TW520360B (en) | 2003-02-11 |
ZA976730B (en) | 1999-07-29 |
HUP0100324A3 (en) | 2001-06-28 |
HUP0100324A2 (hu) | 2001-05-28 |
TR199902326T2 (xx) | 2000-05-22 |
NZ333951A (en) | 2000-09-29 |
IL128251A0 (en) | 1999-11-30 |
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