NO875239L - Fremgangsmaate ved spalting av 1,4-dihydropyridinderivateri optisk aktive isomerer. - Google Patents
Fremgangsmaate ved spalting av 1,4-dihydropyridinderivateri optisk aktive isomerer.Info
- Publication number
- NO875239L NO875239L NO875239A NO875239A NO875239L NO 875239 L NO875239 L NO 875239L NO 875239 A NO875239 A NO 875239A NO 875239 A NO875239 A NO 875239A NO 875239 L NO875239 L NO 875239L
- Authority
- NO
- Norway
- Prior art keywords
- dihydropyridine
- lower alkyl
- dimethyl
- aryl
- carboxy
- Prior art date
Links
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 110
- 150000001875 compounds Chemical class 0.000 claims description 93
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 230000003287 optical effect Effects 0.000 claims description 55
- -1 glucosarnine Chemical compound 0.000 claims description 50
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 48
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 150000003839 salts Chemical group 0.000 claims description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 40
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 claims description 37
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 22
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 22
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 20
- 229960001404 quinidine Drugs 0.000 claims description 19
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- GPLGAQQQNWMVMM-UHFFFAOYSA-N n,n-dimethylcon-5-enin-3-amine Chemical compound C1C=C2CC(N(C)C)CCC2(C)C2C1C1CCC3C(C)N(C)CC31CC2 GPLGAQQQNWMVMM-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical compound N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 claims description 11
- PIIQLZXRLGJEKE-LSDHHAIUSA-N 3-[(3r,4r)-3-ethenylpiperidin-4-yl]-1-quinolin-4-ylpropan-1-one Chemical compound C=C[C@H]1CNCC[C@H]1CCC(=O)C1=CC=NC2=CC=CC=C12 PIIQLZXRLGJEKE-LSDHHAIUSA-N 0.000 claims description 11
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 11
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 claims description 11
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 claims description 11
- 229930014345 anabasine Natural products 0.000 claims description 11
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 claims description 11
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 claims description 11
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 11
- 229960002179 ephedrine Drugs 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 229960000948 quinine Drugs 0.000 claims description 11
- BKMMTJMQCTUHRP-VKHMYHEASA-N (S)-2-aminopropan-1-ol Chemical compound C[C@H](N)CO BKMMTJMQCTUHRP-VKHMYHEASA-N 0.000 claims description 10
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 10
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 10
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 10
- 229930064664 L-arginine Natural products 0.000 claims description 10
- 235000014852 L-arginine Nutrition 0.000 claims description 10
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 10
- 238000003776 cleavage reaction Methods 0.000 claims description 10
- 229960000632 dexamfetamine Drugs 0.000 claims description 10
- 229960002442 glucosamine Drugs 0.000 claims description 10
- 229960005181 morphine Drugs 0.000 claims description 10
- 230000007017 scission Effects 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 239000011833 salt mixture Substances 0.000 claims description 8
- AYYIATOVDZJSNR-UHFFFAOYSA-N Conessine Natural products CC1C2CCC3C4(C)CC=C5CC(CCC5(C)C4CCC23CN1C)N(C)C AYYIATOVDZJSNR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003158 alcohol group Chemical group 0.000 claims description 7
- GPLGAQQQNWMVMM-MYAJQUOBSA-N conessine Chemical compound C1C=C2C[C@@H](N(C)C)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@H]3[C@H](C)N(C)C[C@@]31CC2 GPLGAQQQNWMVMM-MYAJQUOBSA-N 0.000 claims description 7
- 229950001827 conessine Drugs 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 5
- 150000005840 aryl radicals Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- QLNAYPDWIWUVHP-UHFFFAOYSA-N 5-o-[2-[4-(2,3-dihydroxypropoxy)phenyl]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCC=2C=CC(OCC(O)CO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 QLNAYPDWIWUVHP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- AAKPGBJVBKCHHC-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 AAKPGBJVBKCHHC-UHFFFAOYSA-N 0.000 claims 2
- PIIQLZXRLGJEKE-UHFFFAOYSA-N Cinchonicine Natural products C=CC1CNCCC1CCC(=O)C1=CC=NC2=CC=CC=C12 PIIQLZXRLGJEKE-UHFFFAOYSA-N 0.000 claims 1
- 101100232295 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) GLK1 gene Proteins 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- JPXPPUOCSLMCHK-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 230000003185 calcium uptake Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- CRWIANZZHQPMLR-UHFFFAOYSA-N 4-(3h-1,2,3-benzodioxazol-4-yl)-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylic acid Chemical compound [O-][N+](=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC2=C1NOO2 CRWIANZZHQPMLR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000003819 low-pressure liquid chromatography Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- ZFLWDHHVRRZMEI-UHFFFAOYSA-N methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C([N+]([O-])=O)C1C1=CC=CC=C1C(F)(F)F ZFLWDHHVRRZMEI-UHFFFAOYSA-N 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- MBELGTLJWJJGLF-UHFFFAOYSA-N 1,4-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CNC=CC1 MBELGTLJWJJGLF-UHFFFAOYSA-N 0.000 description 2
- LFYNCQUCMUWQGH-UHFFFAOYSA-N 2,6-dimethyl-4-(2-nitrophenyl)-5-propan-2-yloxycarbonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O LFYNCQUCMUWQGH-UHFFFAOYSA-N 0.000 description 2
- QQEOWRHUXVDVJC-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-5-propan-2-yloxycarbonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 QQEOWRHUXVDVJC-UHFFFAOYSA-N 0.000 description 2
- JGGMPEDSNHWUID-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-5-propan-2-ylsulfonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)S(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 JGGMPEDSNHWUID-UHFFFAOYSA-N 0.000 description 2
- MDNBTYVTOBKJEE-UHFFFAOYSA-N 2,6-dimethyl-4-(4-methylphenyl)-5-propan-2-yloxycarbonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=C(C)C=C1 MDNBTYVTOBKJEE-UHFFFAOYSA-N 0.000 description 2
- IYNQCKBKXJAJCC-UHFFFAOYSA-N 2,6-dimethyl-4-(4-methylphenyl)-5-propan-2-ylsulfonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)S(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=C(C)C=C1 IYNQCKBKXJAJCC-UHFFFAOYSA-N 0.000 description 2
- IWGCHFZJCVSNJP-UHFFFAOYSA-N 2,6-dimethyl-5-methylsulfonyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CS(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O IWGCHFZJCVSNJP-UHFFFAOYSA-N 0.000 description 2
- ZFEKLRWBTAWVLG-UHFFFAOYSA-N 2,6-dimethyl-5-methylsulfonyl-4-[3-(trifluoromethoxy)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CS(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(OC(F)(F)F)=C1 ZFEKLRWBTAWVLG-UHFFFAOYSA-N 0.000 description 2
- OMDCFYNMSVPTGB-UHFFFAOYSA-N 2,6-dimethyl-5-methylsulfonyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CS(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(C(F)(F)F)=C1 OMDCFYNMSVPTGB-UHFFFAOYSA-N 0.000 description 2
- UQNCXRKGVABEMP-UHFFFAOYSA-N 2,6-dimethyl-5-nitro-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound [O-][N+](=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 UQNCXRKGVABEMP-UHFFFAOYSA-N 0.000 description 2
- STNFCXWDYJWAKO-UHFFFAOYSA-N 2,6-dimethyl-5-propan-2-yloxycarbonyl-4-[3-(trifluoromethoxy)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(OC(F)(F)F)=C1 STNFCXWDYJWAKO-UHFFFAOYSA-N 0.000 description 2
- MPHHNXAZGUQNMC-UHFFFAOYSA-N 2,6-dimethyl-5-propan-2-yloxycarbonyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(C(F)(F)F)=C1 MPHHNXAZGUQNMC-UHFFFAOYSA-N 0.000 description 2
- PPDMZIZIVAERJX-UHFFFAOYSA-N 2,6-dimethyl-5-propan-2-ylsulfonyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)S(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(C(F)(F)F)=C1 PPDMZIZIVAERJX-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- OZFSEFBXNYBQHK-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2,6-dimethyl-5-methylsulfonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CS(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(Cl)=C1Cl OZFSEFBXNYBQHK-UHFFFAOYSA-N 0.000 description 2
- HSSRMHPFYDXBPP-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2,6-dimethyl-5-propan-2-yloxycarbonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(Cl)=C1Cl HSSRMHPFYDXBPP-UHFFFAOYSA-N 0.000 description 2
- XCUAHCDYCQCYAT-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2,6-dimethyl-5-propan-2-ylsulfonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)S(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(Cl)=C1Cl XCUAHCDYCQCYAT-UHFFFAOYSA-N 0.000 description 2
- KCIBIAFYYVAYEO-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-5-ethoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(Cl)=C1Cl KCIBIAFYYVAYEO-UHFFFAOYSA-N 0.000 description 2
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- XESPSRJVUDFPRM-UHFFFAOYSA-N 5-(2-methoxyethoxycarbonyl)-2,6-dimethyl-4-(4-methylphenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=C(C)C=C1 XESPSRJVUDFPRM-UHFFFAOYSA-N 0.000 description 1
- VGBXGYFTDMLZPD-UHFFFAOYSA-N 5-cyano-2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C#N)C1C1=CC=CC=C1C(F)(F)F VGBXGYFTDMLZPD-UHFFFAOYSA-N 0.000 description 1
- LLPSGQHIECFBIW-UHFFFAOYSA-N 5-cyano-2,6-dimethyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C#N)C1C1=CC=CC(C(F)(F)F)=C1 LLPSGQHIECFBIW-UHFFFAOYSA-N 0.000 description 1
- TVWOOJMMVLFVBO-UHFFFAOYSA-N 5-cyano-2,6-dimethyl-4-pyridin-2-yl-1,4-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C#N)C1C1=CC=CC=N1 TVWOOJMMVLFVBO-UHFFFAOYSA-N 0.000 description 1
- WEHZLVWZBQAYRV-UHFFFAOYSA-N 5-ethoxycarbonyl-2,6-dimethyl-4-pyridin-2-yl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=N1 WEHZLVWZBQAYRV-UHFFFAOYSA-N 0.000 description 1
- IEZIXWBGLMKWDH-UHFFFAOYSA-N 5-ethoxycarbonyl-4-(furan-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CO1 IEZIXWBGLMKWDH-UHFFFAOYSA-N 0.000 description 1
- IBVZOWSIICYUSU-UHFFFAOYSA-N 5-ethylsulfanyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCSC1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O IBVZOWSIICYUSU-UHFFFAOYSA-N 0.000 description 1
- RGESBVCFCLCAQP-UHFFFAOYSA-N 5-ethylsulfanyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCSC1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 RGESBVCFCLCAQP-UHFFFAOYSA-N 0.000 description 1
- JFFNFQIHSXTQKL-UHFFFAOYSA-N 5-ethylsulfanyl-2,6-dimethyl-4-[3-(trifluoromethoxy)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCSC1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(OC(F)(F)F)=C1 JFFNFQIHSXTQKL-UHFFFAOYSA-N 0.000 description 1
- AKDAFIIXHUITRL-UHFFFAOYSA-N 5-ethylsulfanyl-2,6-dimethyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCSC1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(C(F)(F)F)=C1 AKDAFIIXHUITRL-UHFFFAOYSA-N 0.000 description 1
- XMCUBOSCGPOLIA-UHFFFAOYSA-N 5-ethylsulfinyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCS(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O XMCUBOSCGPOLIA-UHFFFAOYSA-N 0.000 description 1
- LQOSHBJKBPNELB-UHFFFAOYSA-N 5-ethylsulfinyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCS(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 LQOSHBJKBPNELB-UHFFFAOYSA-N 0.000 description 1
- AYTNFKCMOLFDAL-UHFFFAOYSA-N 5-ethylsulfinyl-2,6-dimethyl-4-(4-methylphenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCS(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=C(C)C=C1 AYTNFKCMOLFDAL-UHFFFAOYSA-N 0.000 description 1
- ATFIUQFMQNBMAU-UHFFFAOYSA-N 5-ethylsulfinyl-2,6-dimethyl-4-[3-(trifluoromethoxy)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCS(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(OC(F)(F)F)=C1 ATFIUQFMQNBMAU-UHFFFAOYSA-N 0.000 description 1
- SBDJHPGNCMLKED-UHFFFAOYSA-N 5-ethylsulfinyl-2,6-dimethyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCS(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(C(F)(F)F)=C1 SBDJHPGNCMLKED-UHFFFAOYSA-N 0.000 description 1
- ZOZJAJBIHRAESS-UHFFFAOYSA-N 5-ethylsulfonyl-2,6-dimethyl-4-[3-(trifluoromethoxy)phenyl]-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCS(=O)(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(OC(F)(F)F)=C1 ZOZJAJBIHRAESS-UHFFFAOYSA-N 0.000 description 1
- VVNIZEMYAQSUAK-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-(5-methylthiophen-2-yl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=C(C)S1 VVNIZEMYAQSUAK-UHFFFAOYSA-N 0.000 description 1
- KPQNMDYIOPPTFV-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-pyridin-2-yl-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=N1 KPQNMDYIOPPTFV-UHFFFAOYSA-N 0.000 description 1
- ARMFYJUOORLJCL-UHFFFAOYSA-N 5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=CNC=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 ARMFYJUOORLJCL-UHFFFAOYSA-N 0.000 description 1
- MCIAPXKGANXQCE-UHFFFAOYSA-N 5-o-(3-bromopropyl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCBr)C1C1=CC=CC([N+]([O-])=O)=C1 MCIAPXKGANXQCE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 108090000312 Calcium Channels Proteins 0.000 description 1
- 102000003922 Calcium Channels Human genes 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- CJXAEXPPLWQRFR-UHFFFAOYSA-N clemizole Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2N=C1CN1CCCC1 CJXAEXPPLWQRFR-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- OYQKWOWJABIBEA-UHFFFAOYSA-N ethyl 4-(3h-1,2,3-benzodioxazol-4-yl)-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C([N+]([O-])=O)C1C1=CC=CC2=C1NOO2 OYQKWOWJABIBEA-UHFFFAOYSA-N 0.000 description 1
- KCEGZEFUPSPRGU-UHFFFAOYSA-N ethyl 5-methoxysulfonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(S(=O)(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 KCEGZEFUPSPRGU-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- DCHWNCNAHDAWDL-UHFFFAOYSA-N methyl 5-cyano-2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C#N)C1C1=CC=CC=C1C(F)(F)F DCHWNCNAHDAWDL-UHFFFAOYSA-N 0.000 description 1
- HUYZKUNNKXOROX-UHFFFAOYSA-N methyl 5-methoxysulfonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(S(=O)(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 HUYZKUNNKXOROX-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVHUJELLJLJGLN-UHFFFAOYSA-N nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-UHFFFAOYSA-N 0.000 description 1
- 229960005425 nitrendipine Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- GXYPNYLAULHWDV-UHFFFAOYSA-N propan-2-yl 5-methoxysulfonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound COS(=O)(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 GXYPNYLAULHWDV-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/945,760 US4920225A (en) | 1986-12-22 | 1986-12-22 | Resolution of 1,4-dihydropyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO875239D0 NO875239D0 (no) | 1987-12-15 |
| NO875239L true NO875239L (no) | 1988-06-23 |
Family
ID=25483522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO875239A NO875239L (no) | 1986-12-22 | 1987-12-15 | Fremgangsmaate ved spalting av 1,4-dihydropyridinderivateri optisk aktive isomerer. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4920225A (xx) |
| EP (1) | EP0273349A3 (xx) |
| JP (1) | JPS63185960A (xx) |
| KR (1) | KR880007469A (xx) |
| AU (1) | AU8284887A (xx) |
| DK (1) | DK674287A (xx) |
| FI (1) | FI875623A (xx) |
| GB (1) | GB2200631A (xx) |
| HU (1) | HUT45499A (xx) |
| IE (1) | IE873469L (xx) |
| IL (1) | IL84894A0 (xx) |
| NO (1) | NO875239L (xx) |
| ZA (1) | ZA879579B (xx) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3737340A1 (de) * | 1987-11-04 | 1989-05-24 | Bayer Ag | Neue fluormethoxyphenyl-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
| GB8804630D0 (en) * | 1988-02-27 | 1988-03-30 | Pfizer Ltd | Preparation of r-& s-amlodipine |
| IT1230752B (it) * | 1989-02-17 | 1991-10-29 | Boehringer Biochemia Srl | Processo per la preparazione di 1,4 diidropiridine polisostituite in forma enantiomericamente pura. |
| EP0398617A3 (en) * | 1989-05-15 | 1991-11-06 | Merck Sharp & Dohme Ltd. | Process for resolving 1-azabicyclo [2.2.1]heptane-3-carboxylates |
| JPH03141257A (ja) * | 1989-10-26 | 1991-06-17 | Green Cross Corp:The | ジヒドロピリジン誘導体 |
| US5100892A (en) * | 1990-11-13 | 1992-03-31 | Glaxo Inc. | Dihydropyridine vasodilator agents |
| US5135936A (en) * | 1991-03-05 | 1992-08-04 | Marion Merrell Dow Inc. | Isomers of 1-azabicyclo[2.2.2]oct-3-yl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinediacarboxylic and their use as calcium antagonists |
| US5210398A (en) * | 1991-06-14 | 1993-05-11 | Symbol Technologies, Inc. | Optical scanner with extended depth of focus |
| FR2719585B1 (fr) * | 1994-05-05 | 1996-08-02 | Lafon Labor | Procédé d'obtention de 1,4-dihydropyridines optiquement pures. |
| AU5568300A (en) | 1999-06-23 | 2001-01-09 | Ajinomoto Co., Inc. | Novel dihydropyridine derivative |
| WO2002032878A1 (en) * | 2000-10-13 | 2002-04-25 | Eli Lilly And Company | Resolution process for preparation of substantially pure (r) and (s) enantiomers of 2-(4-nitroimidazolyl)-4-methoxyphenylpropionic acid and salts thereof |
| JP2007510728A (ja) * | 2003-11-03 | 2007-04-26 | ミオゲン インコーポレイティッド | 心血管疾患を治療するための１，４−ジヒドロピリジン化合物、薬学的組成物、および方法 |
| ATE407925T1 (de) | 2003-11-03 | 2008-09-15 | Myogen Inc | 1,4-dihydropyridinverbindungen, pharmazeutische verbindungen, und verfahren zur behandlung von herzkreislauferkrankungen |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4370334A (en) * | 1975-07-02 | 1983-01-25 | Fujisawa Pharmaceutical Co., Ltd. | 1,4-Dihydro-pyridine derivatives and methods of using same |
| SE442298B (sv) * | 1978-06-30 | 1985-12-16 | Haessle Ab | 2,6-dimetyl-4-(2,3-diklorfenyl)-1,4-dihydropyridin-3,5-dikarboxylsyra-3-metylester-5-etylester i optisk aktiv form |
| SE429652B (sv) * | 1978-06-30 | 1983-09-19 | Haessle Ab | 2.6-dimetyl-4-(2.3-diklorfenyl)-1.4-dihydropyridin-3.5-dikarboxylsyra-3-metylester-5-etylester |
| DE2935451A1 (de) * | 1979-09-01 | 1981-03-19 | Bayer Ag, 5090 Leverkusen | Optisch aktive 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arneimittel |
| CS228917B2 (en) * | 1981-03-14 | 1984-05-14 | Pfizer | Method of preparing substituted derivatives of 1,4-dihydropyridine |
| ZA83959B (en) * | 1982-03-10 | 1984-09-26 | Sandoz Ltd | 1,4-dihydropyridine derivatives,their preparation and pharmaceutical compositions containing them |
| JPS58208271A (ja) * | 1982-04-30 | 1983-12-03 | Kyowa Hakko Kogyo Co Ltd | １，４−ジヒドロピリジン誘導体 |
| FR2528431B1 (fr) * | 1982-06-15 | 1986-01-10 | Sandoz Sa | Nouveaux derives de la 1,4-dihydropyridine, leur preparation et leur utilisation comme medicaments |
| DE3247118A1 (de) * | 1982-12-20 | 1984-06-20 | Cassella Ag, 6000 Frankfurt | Neue substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| JPS59161392A (ja) * | 1983-03-04 | 1984-09-12 | Nippon Shinyaku Co Ltd | ジヒドロピリジン誘導体及びその製法 |
| EP0141222B1 (en) * | 1983-09-26 | 1989-04-12 | Nissan Chemical Industries Ltd. | Dihydropyridine-5-phosphonic acid cyclic ester |
| GB8412208D0 (en) * | 1984-05-12 | 1984-06-20 | Pfizer Ltd | Quinolone inotropic agents |
| DE3423105A1 (de) * | 1984-06-22 | 1986-01-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung optisch aktiver 1,4-dihydropyridine |
| US4595690A (en) * | 1985-02-11 | 1986-06-17 | Syntex (U.S.A.) Inc. | Antihypertensive dihydropyridine derivatives |
| IL77843A (en) * | 1985-02-11 | 1989-07-31 | Syntex Inc | Dihydropyridine derivatives,process and novel intermediates for their preparation and pharmaceutical compositions containing them |
| US4761420A (en) * | 1986-06-13 | 1988-08-02 | Laboratoires Syntex S.A. | Antihypertensive dihydropyridine derivatives |
-
1986
- 1986-12-22 US US06/945,760 patent/US4920225A/en not_active Expired - Fee Related
-
1987
- 1987-12-15 NO NO875239A patent/NO875239L/no unknown
- 1987-12-17 ZA ZA879579A patent/ZA879579B/xx unknown
- 1987-12-21 HU HU875907A patent/HUT45499A/hu unknown
- 1987-12-21 GB GB08729735A patent/GB2200631A/en active Pending
- 1987-12-21 FI FI875623A patent/FI875623A/fi not_active Application Discontinuation
- 1987-12-21 AU AU82848/87A patent/AU8284887A/en not_active Abandoned
- 1987-12-21 KR KR1019870014603A patent/KR880007469A/ko not_active Application Discontinuation
- 1987-12-21 IL IL84894A patent/IL84894A0/xx unknown
- 1987-12-21 IE IE873469A patent/IE873469L/xx unknown
- 1987-12-21 JP JP62325159A patent/JPS63185960A/ja active Pending
- 1987-12-21 EP EP87118947A patent/EP0273349A3/en not_active Withdrawn
- 1987-12-21 DK DK674287A patent/DK674287A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL84894A0 (en) | 1988-06-30 |
| DK674287D0 (da) | 1987-12-21 |
| KR880007469A (ko) | 1988-08-27 |
| FI875623A0 (fi) | 1987-12-21 |
| HUT45499A (en) | 1988-07-28 |
| US4920225A (en) | 1990-04-24 |
| JPS63185960A (ja) | 1988-08-01 |
| EP0273349A2 (en) | 1988-07-06 |
| EP0273349A3 (en) | 1990-02-14 |
| FI875623A (fi) | 1988-06-23 |
| IE873469L (en) | 1988-06-22 |
| NO875239D0 (no) | 1987-12-15 |
| GB2200631A (en) | 1988-08-10 |
| GB8729735D0 (en) | 1988-02-03 |
| DK674287A (da) | 1988-06-23 |
| AU8284887A (en) | 1988-06-23 |
| ZA879579B (en) | 1989-08-30 |
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