NO852576L - Dihydropyridinderivater. - Google Patents
Dihydropyridinderivater.Info
- Publication number
- NO852576L NO852576L NO852576A NO852576A NO852576L NO 852576 L NO852576 L NO 852576L NO 852576 A NO852576 A NO 852576A NO 852576 A NO852576 A NO 852576A NO 852576 L NO852576 L NO 852576L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- ester
- nitrophenyl
- dihydro
- acetyl
- Prior art date
Links
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 57
- -1 2,5-dichlorophenyl Chemical group 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 150000002081 enamines Chemical class 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 239000012279 sodium borohydride Substances 0.000 claims description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- VEZRCCZBPXTSNZ-UHFFFAOYSA-N 2-propoxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-[2-(propan-2-ylsulfamoyl)acetyl]-1,4-dihydropyridine-3-carboxylate Chemical compound CCCOCCOC(=O)C1=C(C)NC(C)=C(C(=O)CS(=O)(=O)NC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 VEZRCCZBPXTSNZ-UHFFFAOYSA-N 0.000 claims description 3
- DOXADZZFIGIWRW-SIBVEZHUSA-N C1([C@@H]2C(=C(C)NC(C)=C2C(=O)CS(=O)(=O)NC(C)C)C(=O)O[C@@H](C)C=2C=CC=CC=2)=CC=CC([N+]([O-])=O)=C1 Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)CS(=O)(=O)NC(C)C)C(=O)O[C@@H](C)C=2C=CC=CC=2)=CC=CC([N+]([O-])=O)=C1 DOXADZZFIGIWRW-SIBVEZHUSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- SZXGKMSCWHYTNW-UHFFFAOYSA-N propan-2-yl 4-(2,5-dichlorophenyl)-2,6-dimethyl-5-[2-(propan-2-ylsulfamoyl)acetyl]-1,4-dihydropyridine-3-carboxylate Chemical compound CC(C)NS(=O)(=O)CC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC(Cl)=CC=C1Cl SZXGKMSCWHYTNW-UHFFFAOYSA-N 0.000 claims description 3
- KDWTVQKAHGGVDD-UHFFFAOYSA-N propan-2-yl 4-(2-chloro-5-nitrophenyl)-2,6-dimethyl-5-[2-(propan-2-ylsulfamoyl)acetyl]-1,4-dihydropyridine-3-carboxylate Chemical compound CC(C)NS(=O)(=O)CC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC([N+]([O-])=O)=CC=C1Cl KDWTVQKAHGGVDD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- CETHIKRPRUELGC-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2,6-dimethyl-5-[2-(methylsulfamoyl)acetyl]-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CNS(=O)(=O)CC(=O)C1=C(C)NC(C)=C(C(=O)OCC(F)(F)F)C1C1=CC=CC([N+]([O-])=O)=C1 CETHIKRPRUELGC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- NXXOEJWXTMWMHF-UHFFFAOYSA-N 5,6-didehydropyridine Chemical class C1=CN=C=C=C1 NXXOEJWXTMWMHF-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 117
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 35
- 239000013078 crystal Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- OCBNKTFBTDJZHS-UHFFFAOYSA-N 4-amino-2-oxo-n-propan-2-ylpent-3-ene-1-sulfonamide Chemical compound CC(C)NS(=O)(=O)CC(=O)C=C(C)N OCBNKTFBTDJZHS-UHFFFAOYSA-N 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 239000003480 eluent Substances 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- XHMQWYTYNQYUMV-UHFFFAOYSA-N 4-amino-n-methyl-2-oxopent-3-ene-1-sulfonamide Chemical compound CNS(=O)(=O)CC(=O)C=C(C)N XHMQWYTYNQYUMV-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000001665 trituration Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 229940099112 cornstarch Drugs 0.000 description 4
- 210000004351 coronary vessel Anatomy 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 229960001597 nifedipine Drugs 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- FEACZNCUIFEQCG-HYXAFXHYSA-N (z)-3-amino-1-(2-methyl-1,1-dioxo-1,3-thiazolidin-5-yl)but-2-en-1-one Chemical compound CC1NCC(C(=O)\C=C(\C)N)S1(=O)=O FEACZNCUIFEQCG-HYXAFXHYSA-N 0.000 description 3
- FSBSNOJFTDXTDN-UHFFFAOYSA-N 3-methyl-1,1-dioxo-2-propan-2-ylthiazin-5-one Chemical compound CC(C)N1C(C)=CC(=O)CS1(=O)=O FSBSNOJFTDXTDN-UHFFFAOYSA-N 0.000 description 3
- GJIYKPVQXREHPQ-UHFFFAOYSA-N 4-amino-n,n-dimethyl-2-oxopent-3-ene-1-sulfonamide Chemical compound CN(C)S(=O)(=O)CC(=O)C=C(C)N GJIYKPVQXREHPQ-UHFFFAOYSA-N 0.000 description 3
- BFAFOONEQLRGIG-UHFFFAOYSA-N 4-amino-n-ethyl-2-oxopent-3-ene-1-sulfonamide Chemical compound CCNS(=O)(=O)CC(=O)C=C(C)N BFAFOONEQLRGIG-UHFFFAOYSA-N 0.000 description 3
- 206010002383 Angina Pectoris Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 208000019695 Migraine disease Diseases 0.000 description 3
- 206010062575 Muscle contracture Diseases 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 208000006111 contracture Diseases 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 208000028867 ischemia Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- GKSMNBZFSFFBDM-UHFFFAOYSA-N methyl 5-(3-nitrophenyl)-3-oxopent-4-enoate Chemical compound COC(=O)CC(=O)C=CC1=CC=CC([N+]([O-])=O)=C1 GKSMNBZFSFFBDM-UHFFFAOYSA-N 0.000 description 3
- 206010027599 migraine Diseases 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- BWSKOBWSFMYAJP-UHFFFAOYSA-N propan-2-yl 3-(3-nitrophenyl)prop-2-enoate Chemical compound CC(C)OC(=O)C=CC1=CC=CC([N+]([O-])=O)=C1 BWSKOBWSFMYAJP-UHFFFAOYSA-N 0.000 description 3
- SXFZXHSSAJRVJX-UHFFFAOYSA-N propan-2-yl 5-(3-nitrophenyl)-3-oxopent-4-enoate Chemical compound CC(C)OC(=O)CC(=O)C=CC1=CC=CC([N+]([O-])=O)=C1 SXFZXHSSAJRVJX-UHFFFAOYSA-N 0.000 description 3
- BGUZVGXPBFGJRY-UHFFFAOYSA-N propan-2-yl 5-[2-(ethylsulfamoyl)acetyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCNS(=O)(=O)CC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 BGUZVGXPBFGJRY-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- UIIFGNONDFHSPJ-UHFFFAOYSA-N 1,1-dioxo-2h-thiazin-5-one Chemical class O=C1CS(=O)(=O)NC=C1 UIIFGNONDFHSPJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CKQPXEVKGCBLSD-UHFFFAOYSA-N 2,2,2-trifluoroethyl 5-(3-nitrophenyl)-3-oxopent-4-enoate Chemical compound [O-][N+](=O)C1=CC=CC(C=CC(=O)CC(=O)OCC(F)(F)F)=C1 CKQPXEVKGCBLSD-UHFFFAOYSA-N 0.000 description 2
- OVYPKFFDHXGVBU-UHFFFAOYSA-N 2,3,6-trimethyl-1,1-dioxothiazin-5-one Chemical compound CC1C(=O)C=C(C)N(C)S1(=O)=O OVYPKFFDHXGVBU-UHFFFAOYSA-N 0.000 description 2
- DEZLRCMKGCEEMS-UHFFFAOYSA-N 2,3-dimethyl-1,1-dioxothiazin-5-one Chemical compound CN1C(C)=CC(=O)CS1(=O)=O DEZLRCMKGCEEMS-UHFFFAOYSA-N 0.000 description 2
- WNWDIZKVNMCGDM-UHFFFAOYSA-N 2-acetyloxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-[2-(propan-2-ylsulfamoyl)acetyl]-1,4-dihydropyridine-3-carboxylate Chemical compound CC(C)NS(=O)(=O)CC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(C)=O)C1C1=CC=CC([N+]([O-])=O)=C1 WNWDIZKVNMCGDM-UHFFFAOYSA-N 0.000 description 2
- AYZZFWCKDBAZNX-UHFFFAOYSA-N 2-chloroethyl 5-(3-nitrophenyl)-3-oxopent-4-enoate Chemical compound [O-][N+](=O)C1=CC=CC(C=CC(=O)CC(=O)OCCCl)=C1 AYZZFWCKDBAZNX-UHFFFAOYSA-N 0.000 description 2
- COZRVPIOWDLFRD-UHFFFAOYSA-N 2-ethyl-3-methyl-1,1-dioxothiazin-5-one Chemical compound CCN1C(C)=CC(=O)CS1(=O)=O COZRVPIOWDLFRD-UHFFFAOYSA-N 0.000 description 2
- IXEYNNVUXQUCQW-UHFFFAOYSA-N 2-propoxyethyl 5-(3-nitrophenyl)-3-oxopent-4-enoate Chemical compound CCCOCCOC(=O)CC(=O)C=CC1=CC=CC([N+]([O-])=O)=C1 IXEYNNVUXQUCQW-UHFFFAOYSA-N 0.000 description 2
- VCCXGNVTXKZDGA-UHFFFAOYSA-N 4-amino-n-ethyl-2-oxobut-3-ene-1-sulfonamide Chemical compound CCNS(=O)(=O)CC(=O)C=CN VCCXGNVTXKZDGA-UHFFFAOYSA-N 0.000 description 2
- RPFKSQICQSYTDT-UHFFFAOYSA-N 5-amino-3-oxo-N-propan-2-ylhex-4-ene-2-sulfonamide Chemical compound CC(C)NS(=O)(=O)C(C)C(=O)C=C(C)N RPFKSQICQSYTDT-UHFFFAOYSA-N 0.000 description 2
- PSBUOIQTRCGPCH-UHFFFAOYSA-N 5-amino-n-methyl-3-oxohex-4-ene-2-sulfonamide Chemical compound CNS(=O)(=O)C(C)C(=O)C=C(C)N PSBUOIQTRCGPCH-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- WYHWRTRCLQTYEW-UHFFFAOYSA-N propan-2-yl 1,2,6-trimethyl-4-(3-nitrophenyl)-5-[2-(propan-2-ylsulfamoyl)acetyl]-4h-pyridine-3-carboxylate Chemical compound CC(C)NS(=O)(=O)CC(=O)C1=C(C)N(C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 WYHWRTRCLQTYEW-UHFFFAOYSA-N 0.000 description 1
- YXWKDTUBPFPBIB-UHFFFAOYSA-N propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-5-[2-(propan-2-ylsulfamoyl)propanoyl]-1,4-dihydropyridine-3-carboxylate Chemical compound CC(C)NS(=O)(=O)C(C)C(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 YXWKDTUBPFPBIB-UHFFFAOYSA-N 0.000 description 1
- VJLFJKQJEJZORR-UHFFFAOYSA-N propan-2-yl 2-methyl-3-phenylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=CC1=CC=CC=C1 VJLFJKQJEJZORR-UHFFFAOYSA-N 0.000 description 1
- WWPUHEFLKUDHHV-UHFFFAOYSA-N propan-2-yl 3-(2-chloro-5-nitrophenyl)prop-2-enoate Chemical compound CC(C)OC(=O)C=CC1=CC([N+]([O-])=O)=CC=C1Cl WWPUHEFLKUDHHV-UHFFFAOYSA-N 0.000 description 1
- VRSXAXJLRRHWIO-UHFFFAOYSA-N propan-2-yl 3-oxo-4-pyridin-3-ylpent-4-enoate Chemical compound CC(C)OC(=O)CC(=O)C(=C)C1=CC=CN=C1 VRSXAXJLRRHWIO-UHFFFAOYSA-N 0.000 description 1
- LBCUIYCQILXMGG-MDZDMXLPSA-N propan-2-yl 4-(2-chloro-5-nitrophenyl)-2,6-dimethyl-5-[(e)-2-(propan-2-ylsulfamoyl)ethenyl]-1,4-dihydropyridine-3-carboxylate Chemical compound CC(C)NS(=O)(=O)\C=C\C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC([N+]([O-])=O)=CC=C1Cl LBCUIYCQILXMGG-MDZDMXLPSA-N 0.000 description 1
- CFFHNLWNTZXZIX-UHFFFAOYSA-N propan-2-yl 4-naphthalen-1-yl-3-oxopent-4-enoate Chemical compound C1=CC=C2C(C(=C)C(=O)CC(=O)OC(C)C)=CC=CC2=C1 CFFHNLWNTZXZIX-UHFFFAOYSA-N 0.000 description 1
- UOWDDFFEIYYAPJ-UHFFFAOYSA-N propan-2-yl 5-(2,5-dichlorophenyl)-3-oxopent-4-enoate Chemical compound CC(C)OC(=O)CC(=O)C=CC1=CC(Cl)=CC=C1Cl UOWDDFFEIYYAPJ-UHFFFAOYSA-N 0.000 description 1
- ZIVHKCVNXWYJON-ZHACJKMWSA-N propan-2-yl 5-[(e)-2-(ethylsulfamoyl)ethenyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCNS(=O)(=O)\C=C\C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 ZIVHKCVNXWYJON-ZHACJKMWSA-N 0.000 description 1
- VSRSQDMWBSKNSF-UHFFFAOYSA-N propan-2-yl pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1 VSRSQDMWBSKNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 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
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- HVOHENMYTHWXRH-UHFFFAOYSA-N trimethyl(4-trimethylsilyloxypenta-1,3-dien-2-yloxy)silane Chemical compound C[Si](C)(C)OC(C)=CC(=C)O[Si](C)(C)C HVOHENMYTHWXRH-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- 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
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Dental Preparations (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH309784 | 1984-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852576L true NO852576L (no) | 1985-12-30 |
Family
ID=4248551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852576A NO852576L (no) | 1984-06-27 | 1985-06-26 | Dihydropyridinderivater. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4742069A (da) |
| EP (1) | EP0166422A1 (da) |
| JP (1) | JPS6118762A (da) |
| CN (1) | CN85105335A (da) |
| AU (1) | AU4399185A (da) |
| DK (1) | DK288085A (da) |
| ES (2) | ES8609253A1 (da) |
| FI (1) | FI852359L (da) |
| GR (1) | GR851554B (da) |
| HU (1) | HU193784B (da) |
| IL (1) | IL75595A0 (da) |
| MC (1) | MC1675A1 (da) |
| NO (1) | NO852576L (da) |
| PH (1) | PH21510A (da) |
| PT (1) | PT80719B (da) |
| ZA (1) | ZA854665B (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6541479B1 (en) * | 1997-12-02 | 2003-04-01 | Massachusetts College Of Pharmacy | Calcium channel blockers |
| CN106011652B (zh) | 2016-06-28 | 2017-12-26 | 宝山钢铁股份有限公司 | 一种磷化性能优异的冷轧低密度钢板及其制造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2639498A1 (de) * | 1976-09-02 | 1978-03-09 | Bayer Ag | Neue schwefelhaltige amino-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2658183A1 (de) * | 1976-12-22 | 1978-07-06 | Bayer Ag | In 2-position substituierte 1,4- dihydropyridin-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2747513A1 (de) * | 1977-10-22 | 1979-05-03 | Bayer Ag | Dihydropyridine mit schwefelhaltigen estergruppierungen |
| 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 |
| DE3116129A1 (de) * | 1981-04-23 | 1982-11-11 | Hoechst Ag, 6000 Frankfurt | 2-ketosulfonamide und verfahren zu ihrer herstellung |
| NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
-
1985
- 1985-06-13 FI FI852359A patent/FI852359L/fi not_active Application Discontinuation
- 1985-06-17 US US06/745,743 patent/US4742069A/en not_active Expired - Fee Related
- 1985-06-20 ZA ZA854665A patent/ZA854665B/xx unknown
- 1985-06-21 IL IL75595A patent/IL75595A0/xx unknown
- 1985-06-24 AU AU43991/85A patent/AU4399185A/en not_active Abandoned
- 1985-06-24 HU HU852464A patent/HU193784B/hu unknown
- 1985-06-25 GR GR851554A patent/GR851554B/el unknown
- 1985-06-25 EP EP85107835A patent/EP0166422A1/de not_active Withdrawn
- 1985-06-25 DK DK288085A patent/DK288085A/da not_active Application Discontinuation
- 1985-06-25 PH PH32451A patent/PH21510A/en unknown
- 1985-06-25 MC MC851776A patent/MC1675A1/xx unknown
- 1985-06-26 JP JP60138052A patent/JPS6118762A/ja active Pending
- 1985-06-26 PT PT80719A patent/PT80719B/pt unknown
- 1985-06-26 ES ES544558A patent/ES8609253A1/es not_active Expired
- 1985-06-26 NO NO852576A patent/NO852576L/no unknown
- 1985-07-12 CN CN198585105335A patent/CN85105335A/zh active Pending
-
1986
- 1986-01-31 ES ES551817A patent/ES8705388A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL75595A0 (en) | 1985-10-31 |
| PT80719A (en) | 1985-07-01 |
| DK288085D0 (da) | 1985-06-25 |
| FI852359L (fi) | 1985-12-28 |
| ZA854665B (en) | 1986-02-26 |
| FI852359A0 (fi) | 1985-06-13 |
| HU193784B (en) | 1987-11-30 |
| HUT37923A (en) | 1986-03-28 |
| ES8609253A1 (es) | 1986-09-01 |
| AU4399185A (en) | 1986-01-02 |
| PT80719B (en) | 1987-04-23 |
| ES8705388A1 (es) | 1987-05-01 |
| MC1675A1 (fr) | 1986-06-03 |
| US4742069A (en) | 1988-05-03 |
| DK288085A (da) | 1985-12-28 |
| PH21510A (en) | 1987-11-10 |
| CN85105335A (zh) | 1987-01-14 |
| GR851554B (da) | 1985-11-25 |
| JPS6118762A (ja) | 1986-01-27 |
| ES551817A0 (es) | 1987-05-01 |
| ES544558A0 (es) | 1986-09-01 |
| EP0166422A1 (de) | 1986-01-02 |
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