CH660190A5 - 1,4-dihydropyridin-derivate, verfahren zur ihrer herstellung und sie enthaltende pharmazeutische zubereitungen. - Google Patents
1,4-dihydropyridin-derivate, verfahren zur ihrer herstellung und sie enthaltende pharmazeutische zubereitungen. Download PDFInfo
- Publication number
- CH660190A5 CH660190A5 CH6050/83A CH605083A CH660190A5 CH 660190 A5 CH660190 A5 CH 660190A5 CH 6050/83 A CH6050/83 A CH 6050/83A CH 605083 A CH605083 A CH 605083A CH 660190 A5 CH660190 A5 CH 660190A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- compounds
- nitrogen atom
- alkyl
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 125
- -1 2,1,3-benzoxadiazolyl Chemical group 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 6
- 230000008030 elimination Effects 0.000 claims description 6
- 238000003379 elimination reaction Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- COLPLFZHPXIFCQ-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical class OC(=O)C1=CNC=C(C(O)=O)C1 COLPLFZHPXIFCQ-UHFFFAOYSA-N 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 150000002923 oximes Chemical group 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 2
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 125000004103 aminoalkyl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001241 acetals Chemical class 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000003544 oxime group Chemical group 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 208000019695 Migraine disease Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BJNVDYGHDIHFSL-UHFFFAOYSA-N 3-O-methyl 5-O-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2-cyano-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C(C)(C)OC(=O)C1=C(NC(=C(C1C1=CC=CC2=NON=C21)C(=O)OC)C#N)C BJNVDYGHDIHFSL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- RGAHQPXNVPJMRO-UHFFFAOYSA-N methyl 3-amino-4,4-dimethoxybut-2-enoate Chemical compound COC(OC)C(N)=CC(=O)OC RGAHQPXNVPJMRO-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- JDTUPLBMGDDPJS-VIFPVBQESA-N (2r)-2-methoxy-2-phenylethanol Chemical compound CO[C@@H](CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-VIFPVBQESA-N 0.000 description 1
- LNRNCICDCMITMF-UHFFFAOYSA-N 3-amino-4,4-dimethoxybut-2-enoic acid Chemical compound NC(=CC(=O)O)C(OC)OC LNRNCICDCMITMF-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AGTOOXIMMLKPLG-BBQAJUCSSA-N CO[C@@H](COC(=O)C1=C(NC(=C(C1C1=CC=CC2=NON=C21)C(=O)OC(C)C)C)C(OC)OC)C2=CC=CC=C2 Chemical class CO[C@@H](COC(=O)C1=C(NC(=C(C1C1=CC=CC2=NON=C21)C(=O)OC(C)C)C)C(OC)OC)C2=CC=CC=C2 AGTOOXIMMLKPLG-BBQAJUCSSA-N 0.000 description 1
- 206010058842 Cerebrovascular insufficiency Diseases 0.000 description 1
- 208000006561 Cluster Headache Diseases 0.000 description 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010017577 Gait disturbance Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 208000001407 Vascular Headaches Diseases 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000004442 acylamino group Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 125000000051 benzyloxy group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000004556 brain Anatomy 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
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 208000018912 cluster headache syndrome Diseases 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 208000001286 intracranial vasospasm Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- OXPLODJFQDRHIZ-UHFFFAOYSA-N methyl 3-amino-4,4-diethoxybut-2-enoate Chemical compound CCOC(OCC)C(N)=CC(=O)OC OXPLODJFQDRHIZ-UHFFFAOYSA-N 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000005544 phthalimido group Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH147782 | 1982-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH660190A5 true CH660190A5 (de) | 1987-03-31 |
Family
ID=4211396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6050/83A CH660190A5 (de) | 1982-03-10 | 1983-02-24 | 1,4-dihydropyridin-derivate, verfahren zur ihrer herstellung und sie enthaltende pharmazeutische zubereitungen. |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS58180483A (nl) |
| AU (1) | AU1169583A (nl) |
| BE (1) | BE895957A (nl) |
| CH (1) | CH660190A5 (nl) |
| DE (1) | DE3305577A1 (nl) |
| DK (1) | DK63583A (nl) |
| ES (1) | ES520201A0 (nl) |
| FI (1) | FI830617L (nl) |
| FR (1) | FR2523128B1 (nl) |
| GB (1) | GB2117761B (nl) |
| IL (1) | IL68005A0 (nl) |
| IT (1) | IT1197588B (nl) |
| NL (1) | NL8300739A (nl) |
| PT (1) | PT76290B (nl) |
| SE (1) | SE8301072L (nl) |
| WO (1) | WO1983003097A1 (nl) |
| ZA (1) | ZA83959B (nl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414213A (en) * | 1982-03-22 | 1983-11-08 | Mead Johnson & Company | Dihydropyridyl cyclic imidate esters and their pharmaceutical use |
| US4920225A (en) * | 1986-12-22 | 1990-04-24 | Laboratoires Syntex S.A. | Resolution of 1,4-dihydropyridine derivatives |
| JP2002202369A (ja) * | 2000-12-27 | 2002-07-19 | Nikon Corp | 光信号検出装置及び測距装置 |
| CN102766137B (zh) * | 2012-08-07 | 2015-07-08 | 四川百利药业有限责任公司 | 一种高纯度伊拉地平的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1552911A (en) * | 1975-07-02 | 1979-09-19 | Fujisawa Pharmaceutical Co | 1,4 dihydropyridine derivatives and the preparation thereof |
| GB1591089A (en) * | 1976-12-17 | 1981-06-10 | Fujisawa Pharmaceutical Co | 1,4-dihydropyridine derivatives and process for preparation thereof |
| DK149855C (da) * | 1977-06-20 | 1987-04-21 | Sandoz Ag | Analogifremgangsmaade til fremstilling af 1,4-dihydropyridinderivater |
| CH639659A5 (de) * | 1978-12-18 | 1983-11-30 | Sandoz Ag | Neue 1,4-dihydropyridinderivate, deren herstellung und verwendung. |
| US4307103A (en) * | 1978-09-08 | 1981-12-22 | Fujisawa Pharmaceutical Co., Ltd. | Dihydropyridine derivative, processes for preparation thereof and pharmaceutical composition comprising the same |
| CA1117117A (en) * | 1978-10-10 | 1982-01-26 | Fujisawa Pharmaceutical Co., Ltd. | 2-methyl-dihydropyridine compound, processes for preparation thereof and pharmaceutical composition comprising the same |
| FI793848A (fi) * | 1978-12-18 | 1980-06-19 | Sandoz Ag | Benzoxadiazoler och benzothiadiazoler deras framstaellning och farmaceutiska kompositioner innehaollande dessa |
| DE2949464A1 (de) * | 1978-12-18 | 1980-06-26 | Sandoz Ag | Benzoxadiazole und benzothiadiazole, ihre herstellung und verwendung |
| GB2050375B (en) * | 1979-05-11 | 1983-02-23 | Fujisawa Pharmaceutical Co | 4-cyanophenyl-1,4-dihydropyridine compound processes for preparation thereof and pharmaceutical composition comprising the same |
| DE3269219D1 (en) * | 1981-11-17 | 1986-03-27 | Fisons Plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
-
1983
- 1983-02-11 ZA ZA83959A patent/ZA83959B/xx unknown
- 1983-02-14 DK DK63583A patent/DK63583A/da not_active Application Discontinuation
- 1983-02-18 DE DE19833305577 patent/DE3305577A1/de not_active Withdrawn
- 1983-02-21 FR FR8302895A patent/FR2523128B1/fr not_active Expired
- 1983-02-21 AU AU11695/83A patent/AU1169583A/en not_active Abandoned
- 1983-02-21 BE BE1/10727A patent/BE895957A/fr not_active IP Right Cessation
- 1983-02-24 FI FI830617A patent/FI830617L/fi not_active Application Discontinuation
- 1983-02-24 WO PCT/CH1983/000020 patent/WO1983003097A1/en unknown
- 1983-02-24 CH CH6050/83A patent/CH660190A5/de not_active IP Right Cessation
- 1983-02-25 PT PT76290A patent/PT76290B/pt unknown
- 1983-02-25 IT IT47806/83A patent/IT1197588B/it active
- 1983-02-25 SE SE8301072A patent/SE8301072L/xx not_active Application Discontinuation
- 1983-02-28 JP JP58032694A patent/JPS58180483A/ja active Pending
- 1983-02-28 IL IL68005A patent/IL68005A0/xx unknown
- 1983-02-28 GB GB08305525A patent/GB2117761B/en not_active Expired
- 1983-02-28 NL NL8300739A patent/NL8300739A/nl not_active Application Discontinuation
- 1983-03-01 ES ES520201A patent/ES520201A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB8305525D0 (en) | 1983-03-30 |
| FR2523128A1 (fr) | 1983-09-16 |
| BE895957A (fr) | 1983-08-22 |
| GB2117761B (en) | 1986-01-29 |
| ES8500057A1 (es) | 1984-10-01 |
| ES520201A0 (es) | 1984-10-01 |
| SE8301072L (sv) | 1983-09-11 |
| FI830617L (fi) | 1983-09-11 |
| PT76290A (en) | 1983-03-01 |
| SE8301072D0 (sv) | 1983-02-25 |
| WO1983003097A1 (en) | 1983-09-15 |
| IT1197588B (it) | 1988-12-06 |
| DK63583A (da) | 1983-09-11 |
| DK63583D0 (da) | 1983-02-14 |
| FI830617A0 (fi) | 1983-02-24 |
| DE3305577A1 (de) | 1983-09-22 |
| AU1169583A (en) | 1983-09-15 |
| JPS58180483A (ja) | 1983-10-21 |
| GB2117761A (en) | 1983-10-19 |
| IT8347806A0 (it) | 1983-02-25 |
| IL68005A0 (en) | 1983-06-15 |
| NL8300739A (nl) | 1983-10-03 |
| PT76290B (en) | 1985-12-03 |
| FR2523128B1 (fr) | 1985-10-18 |
| ZA83959B (en) | 1984-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |