DD234424A5 - Verfahren zur herstellung von dihydropyridinlactonen - Google Patents

Verfahren zur herstellung von dihydropyridinlactonen Download PDF

Info

Publication number: DD234424A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; atoms; formula; chain; optionally
Prior art date: 1984-03-23

Application number

DD85274322A

Other languages

German (de)

English (en)

Inventor

Siegfried Goldmann

Friedrich Bossert

Hilmar Bischhoff

Dieter Petzinna

Walter Puls

Klaus Schlossmann

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-03-23

Filing date

1985-03-21

Publication date

1986-04-02

1985-03-21 Application filed by ��@��k�� filed Critical ��@��k��

1986-04-02 Publication of DD234424A5 publication Critical patent/DD234424A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 24
238000004519 manufacturing process Methods 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims abstract description 25
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
-1 dihydropyridine lactones Chemical class 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 17
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical group 0.000 claims abstract description 11
229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
125000004122 cyclic group Chemical group 0.000 claims abstract description 6
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract 4
125000004432 carbon atom Chemical group C* 0.000 claims description 54
239000000460 chlorine Substances 0.000 claims description 34
229910052801 chlorine Inorganic materials 0.000 claims description 26
125000001309 chloro group Chemical group Cl* 0.000 claims description 25
229910052794 bromium Inorganic materials 0.000 claims description 21
239000003960 organic solvent Substances 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 14
239000011737 fluorine Substances 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
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 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
150000002081 enamines Chemical class 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
229930195734 saturated hydrocarbon Natural products 0.000 claims description 8
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 8
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 7
150000001299 aldehydes Chemical class 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 claims description 6
230000003287 optical effect Effects 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
125000000468 ketone group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
125000006241 alcohol protecting group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 2
WHKQZPGIUHYQMQ-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-1-ethyl-2-methyl-5-oxo-4,7-dihydrofuro[3,4-b]pyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)N(CC)C(COC2=O)=C2C1C1=CC=CC=C1Cl WHKQZPGIUHYQMQ-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
150000004679 hydroxides Chemical class 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
150000003462 sulfoxides Chemical class 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
RLYGEFOJLQDEOF-UHFFFAOYSA-N CCN1C(=C(C(C2=C1COC2=O)C3=CC=CC=C3Cl)C(=O)OCC(C)C)C Chemical compound CCN1C(=C(C(C2=C1COC2=O)C3=CC=CC=C3Cl)C(=O)OCC(C)C)C RLYGEFOJLQDEOF-UHFFFAOYSA-N 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
NPUSXSOBPNHOPH-UHFFFAOYSA-N propan-2-yl 4-(2-chlorophenyl)-1-ethyl-2-methyl-5-oxo-4,7-dihydrofuro[3,4-b]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)N(CC)C(COC2=O)=C2C1C1=CC=CC=C1Cl NPUSXSOBPNHOPH-UHFFFAOYSA-N 0.000 claims 1
239000008280 blood Substances 0.000 abstract description 9
210000004369 blood Anatomy 0.000 abstract description 9
150000002431 hydrogen Chemical class 0.000 abstract description 8
206010012601 diabetes mellitus Diseases 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 4
230000010030 glucose lowering effect Effects 0.000 abstract description 4
125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract 1
239000004215 Carbon black (E152) Substances 0.000 abstract 1
229930195733 hydrocarbon Natural products 0.000 abstract 1
125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
239000007858 starting material Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000004663 dialkyl amino group Chemical group 0.000 description 4
229940052303 ethers for general anesthesia Drugs 0.000 description 4
239000008103 glucose Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229950005499 carbon tetrachloride Drugs 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
229960004132 diethyl ether Drugs 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000003826 tablet Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000004665 trialkylsilyl group Chemical group 0.000 description 2
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
239000004097 EU approved flavor enhancer Substances 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004366 Glucose oxidase Substances 0.000 description 1
108010015776 Glucose oxidase Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 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
235000021355 Stearic acid Nutrition 0.000 description 1
238000000692 Student's t-test Methods 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical group ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
NERZGJMDVRLFHL-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-2-methyl-5-oxo-4,7-dihydro-1h-furo[3,4-b]pyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(COC2=O)=C2C1C1=CC=CC=C1Cl NERZGJMDVRLFHL-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
238000003304 gavage Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940116332 glucose oxidase Drugs 0.000 description 1
235000019420 glucose oxidase Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
WCDGRLYFXMYHQB-UHFFFAOYSA-N potassium;diethylazanide Chemical compound [K+].CC[N-]CC WCDGRLYFXMYHQB-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 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
239000000243 solution Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000012353 t test Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Endocrinology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Emergency Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyrane Compounds (AREA)
Endoscopes (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Polyesters Or Polycarbonates (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD85274322A 1984-03-23 1985-03-21 Verfahren zur herstellung von dihydropyridinlactonen DD234424A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843410645 DE3410645A1 (de)	1984-03-23	1984-03-23	L-alkylsubstituierte 1,4-dihydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln

Publications (1)

Publication Number	Publication Date
DD234424A5 true DD234424A5 (de)	1986-04-02

Family

ID=6231357

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85274322A DD234424A5 (de)	1984-03-23	1985-03-21	Verfahren zur herstellung von dihydropyridinlactonen

Country Status (24)

Country	Link
US (1)	US5026714A (es)
EP (1)	EP0158138B1 (es)
JP (1)	JPS60209584A (es)
KR (1)	KR850006439A (es)
AT (1)	ATE37880T1 (es)
AU (1)	AU569783B2 (es)
CA (1)	CA1249270A (es)
CS (1)	CS250681B2 (es)
DD (1)	DD234424A5 (es)
DE (2)	DE3410645A1 (es)
DK (1)	DK158517C (es)
EG (1)	EG16785A (es)
ES (9)	ES8607309A1 (es)
FI (1)	FI83651C (es)
GR (1)	GR850719B (es)
HU (1)	HU191167B (es)
IL (1)	IL74659A (es)
NO (1)	NO161259C (es)
NZ (1)	NZ211512A (es)
PH (3)	PH23826A (es)
PL (1)	PL143884B1 (es)
PT (1)	PT80146B (es)
SU (1)	SU1319785A3 (es)
ZA (1)	ZA852172B (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3521761A1 (de) *	1985-06-19	1987-01-02	Bayer Ag	Neue 1,4-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln
DE3600596A1 (de) *	1986-01-11	1987-07-16	Bayer Ag	4-aminoaryldihydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
US5162338A (en) *	1986-01-11	1992-11-10	Bayer Aktiengesellschaft	Circulation active 4-aminoaryldihydropryidine lactones
DE3629545A1 (de) *	1986-08-30	1988-03-10	Bayer Ag	Dihydropyridinverbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE3706204A1 (de) *	1987-02-26	1988-09-08	Bayer Ag	Benzylaminoaryl-dihydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
GB8716971D0 (en) *	1987-07-17	1987-08-26	Pfizer Ltd	Therapeutic agents
DE4430092A1 (de) *	1994-08-25	1996-02-29	Bayer Ag	2,3-Cyclisch kondensierte 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP1663227A2 (en) *	2003-09-10	2006-06-07	Synta Pharmaceuticals Corporation	Dihydropyridine compounds for treating or preventing metabolic disorders
WO2021253180A1 (en)	2020-06-15	2021-12-23	Novartis Ag	Methyl (r) -2- (fluoromethyl) -5-oxo-4-phenyl-4, 5, 6, 7-tetrahydro-1h-cyclopenta [b] pyridine-3-carboxylate and methyl (r) -2- (fluoromethyl) -5-oxo-4-phenyl-1, 4, 5, 7-tetrahydrofuro [3, 4-b] pyridine-3-carboxylate as cav1.2 activators
PY2147613A (es)	2020-06-16	2022-11-10	Norvatis Ag	COMPUESTOS DE METIL 2–METIL–5–OXO–1,4,5,7–TETRAHIDROFURO[3,4–b]PIRIDINA–3–CARBOXILATO COMO ACTIVADORES DE CAV1.2

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2005116C3 (de) *	1970-02-05	1980-02-14	Bayer Ag, 5090 Leverkusen	Symmetrische 1,4-Dihydropyridin-3,5-dicarbonsäureester
GB1552911A (en) *	1975-07-02	1979-09-19	Fujisawa Pharmaceutical Co	1,4 dihydropyridine derivatives and the preparation thereof
US4284634A (en) *	1975-07-02	1981-08-18	Fujisawa Pharmaceutical Co., Ltd.	1,4-Dihydropyridine derivatives, and pharmaceutical method of the same
US4253248A (en)	1979-04-16	1981-03-03	Cornish Judson E	Teaching machine apparatus
DE3130041A1 (de) *	1981-07-30	1983-02-17	Bayer Ag, 5090 Leverkusen	Dihydropyridine mit positiv inotroper wirkung, neue verbindungen, ihre verwendung in arzneimitteln und verfahren zu ihrer herstellung
DE3206671A1 (de) *	1982-02-25	1983-09-01	Bayer Ag, 5090 Leverkusen	Dihydropyridine mit positiv inotroper wirkung, neue verbindungen, ihre verwendung in arzneimitteln 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
US4497808A (en) *	1981-12-30	1985-02-05	Ciba-Geigy Corporation	N-Oxide compounds useful in the treatment of cardiovascular ailments
DE3209276A1 (de) *	1982-03-13	1983-09-15	Bayer Ag, 5090 Leverkusen	Arzneimittel mit antihypoxischer und ischaemie-protektiver wirkung
DE3209274A1 (de) *	1982-03-13	1983-09-15	Bayer Ag, 5090 Leverkusen	Pyridincarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
EP0111455A3 (de) *	1982-12-10	1984-07-25	Ciba-Geigy Ag	Ungesättigte Lactone
DE3521761A1 (de) *	1985-06-19	1987-01-02	Bayer Ag	Neue 1,4-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln
DE3601226A1 (de) *	1986-01-17	1987-07-23	Bayer Ag	Dihydropyridinlactole, verfahren zur herstellung und ihre verwendung in arzneimitteln

1984
- 1984-03-23 DE DE19843410645 patent/DE3410645A1/de not_active Withdrawn
1985
- 1985-02-28 PH PH31929A patent/PH23826A/en unknown
- 1985-03-06 NO NO850891A patent/NO161259C/no unknown
- 1985-03-12 DE DE8585102793T patent/DE3565541D1/de not_active Expired
- 1985-03-12 AT AT85102793T patent/ATE37880T1/de active
- 1985-03-12 EP EP85102793A patent/EP0158138B1/de not_active Expired
- 1985-03-15 ES ES541309A patent/ES8607309A1/es not_active Expired
- 1985-03-15 SU SU853865401A patent/SU1319785A3/ru active
- 1985-03-19 JP JP60053524A patent/JPS60209584A/ja active Pending
- 1985-03-19 CS CS851923A patent/CS250681B2/cs unknown
- 1985-03-20 NZ NZ211512A patent/NZ211512A/xx unknown
- 1985-03-20 EG EG182/85A patent/EG16785A/xx active
- 1985-03-20 IL IL74659A patent/IL74659A/xx unknown
- 1985-03-20 HU HU851033A patent/HU191167B/hu not_active IP Right Cessation
- 1985-03-21 KR KR1019850001857A patent/KR850006439A/ko not_active Ceased
- 1985-03-21 CA CA000477087A patent/CA1249270A/en not_active Expired
- 1985-03-21 GR GR850719A patent/GR850719B/el unknown
- 1985-03-21 FI FI851143A patent/FI83651C/fi not_active IP Right Cessation
- 1985-03-21 PT PT80146A patent/PT80146B/pt not_active IP Right Cessation
- 1985-03-21 DD DD85274322A patent/DD234424A5/de not_active IP Right Cessation
- 1985-03-22 PL PL1985252522A patent/PL143884B1/pl unknown
- 1985-03-22 ZA ZA852172A patent/ZA852172B/xx unknown
- 1985-03-22 DK DK131685A patent/DK158517C/da not_active IP Right Cessation
- 1985-03-25 AU AU40449/85A patent/AU569783B2/en not_active Ceased
1986
- 1986-01-31 ES ES551548A patent/ES8702418A1/es not_active Expired
- 1986-01-31 ES ES551543A patent/ES8702415A1/es not_active Expired
- 1986-01-31 ES ES551542A patent/ES8702414A1/es not_active Expired
- 1986-01-31 ES ES551547A patent/ES8704174A1/es not_active Expired
- 1986-01-31 ES ES551541A patent/ES8702413A1/es not_active Expired
- 1986-01-31 ES ES551546A patent/ES8704173A1/es not_active Expired
- 1986-01-31 ES ES551545A patent/ES8702417A1/es not_active Expired
- 1986-01-31 ES ES551544A patent/ES8702416A1/es not_active Expired
- 1986-03-18 PH PH33544A patent/PH23455A/en unknown
1987
- 1987-07-23 PH PH35576A patent/PH24347A/en unknown
1989
- 1989-11-13 US US07/436,157 patent/US5026714A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FI851143L (fi)	1985-09-24
ES551544A0 (es)	1987-01-01
ES8702418A1 (es)	1986-12-16
ES551541A0 (es)	1987-01-01
DE3565541D1 (en)	1988-11-17
PL143884B1 (en)	1988-03-31
SU1319785A3 (ru)	1987-06-23
PT80146A (en)	1985-04-01
ZA852172B (en)	1985-12-24
AU569783B2 (en)	1988-02-18
FI83651B (fi)	1991-04-30
ES8607309A1 (es)	1986-06-16
DK158517B (da)	1990-05-28
EP0158138B1 (de)	1988-10-12
JPS60209584A (ja)	1985-10-22
ES551546A0 (es)	1987-03-16
CS250681B2 (en)	1987-05-14
ES541309A0 (es)	1986-06-16
ES8702415A1 (es)	1986-12-16
DK158517C (da)	1990-11-05
NO161259B (no)	1989-04-17
DK131685A (da)	1985-09-24
EP0158138A1 (de)	1985-10-16
ES551547A0 (es)	1987-03-16
PH23455A (en)	1989-08-07
IL74659A (en)	1988-11-30
PT80146B (en)	1987-03-23
ES551545A0 (es)	1986-12-16
DE3410645A1 (de)	1985-09-26
ES8702416A1 (es)	1987-01-01
IL74659A0 (en)	1985-06-30
CA1249270A (en)	1989-01-24
PH23826A (en)	1989-11-23
DK131685D0 (da)	1985-03-22
EG16785A (en)	1990-10-30
ATE37880T1 (de)	1988-10-15
NO850891L (no)	1985-09-24
FI851143A0 (fi)	1985-03-21
ES551543A0 (es)	1986-12-16
ES8702414A1 (es)	1986-12-16
ES8704173A1 (es)	1987-03-16
GR850719B (es)	1985-07-19
HU191167B (en)	1987-01-28
US5026714A (en)	1991-06-25
PL252522A1 (en)	1986-04-08
ES551548A0 (es)	1986-12-16
FI83651C (fi)	1991-08-12
HUT37795A (en)	1986-02-28
NO161259C (no)	1989-07-26
ES551542A0 (es)	1986-12-16
ES8702413A1 (es)	1987-01-01
NZ211512A (en)	1988-07-28
AU4044985A (en)	1985-09-26
ES8702417A1 (es)	1986-12-16
PH24347A (en)	1990-06-13
KR850006439A (ko)	1985-10-05
ES8704174A1 (es)	1987-03-16

Legal Events

Date	Code	Title	Description
1995-08-03	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0012180B1 (de)	1982-06-23	Neue 1,4-Dihydropyridinverbindungen, Verfahren zu ihrer Herstellung, die genannten Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel
EP0088274B1 (de)	1986-09-03	Neue 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung und ihrer Verwendung in Arzneimitteln
EP0009206B1 (de)	1981-10-14	Fluorhaltige 1,4-Dihydropyridine, diese enthaltende Arzneimittel sowie Verfahren zu ihrer Herstellung
EP0088938B1 (de)	1986-04-30	Verwendung von Pyridinverbindungen zur Herstellung von Arzneimitteln mit antihypoxischer und Ischämie-protektiver Wirkung
EP0088940B1 (de)	1986-05-21	Pyridincarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
EP0110073A1 (de)	1984-06-13	Verfahren zur Herstellung von Tetrahydropyridinen
EP0123112B1 (de)	1988-09-21	Chromon- und thiochromonsubstituierte 1,4-Dihydropyridinderivate, mehrere Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln
DD234424A5 (de)	1986-04-02	Verfahren zur herstellung von dihydropyridinlactonen
EP0209701B1 (de)	1989-08-16	Neue 1,4-Dihydropyridine, Verfahren zur Herstellung und ihre Verwendung in Arzneimitteln
EP0039863B1 (de)	1983-12-28	1,4-Dihydropyridine mit unterschiedlichen Substituenten in 2- und 6-Position, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
EP0123095B1 (de)	1988-10-26	Chromon- und thiochromonsubstituierte 1,4-Dihydropyridinlactone, mehrere Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
EP0452712A1 (de)	1991-10-23	Neue 4-Chinolyl-dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
EP0127826B1 (de)	1990-07-04	1,4-Dihydropyridine, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln
EP0010130A1 (de)	1980-04-30	Sila-substituierte 1,4-Dihydropyridinderivate, Verfahren zu ihrer Herstellung, Arzneimittel und Verfahren zu deren Herstellung
DE4313690A1 (de)	1994-11-03	Kondensierte Chinolyl-dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
EP0157324A2 (de)	1985-10-09	Tetrahydrothienopyridine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
EP0236838A2 (de)	1987-09-16	Aminoester-Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung
CH633265A5 (de)	1982-11-30	Verfahren zur herstellung des neuen 1.4-dihydro-2.6-dimethyl-4-(3-nitrophenyl)-3.5-pyridindicarbonsaeure-isopropyl-(2-propoxy-aethyl)-esters.
EP0362632A2 (de)	1990-04-11	Basische 4-Aryl-DHP-amide, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
DE3414801A1 (de)	1985-10-24	4-(nitrophenyl)-tetrahydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0231511B1 (de)	1991-04-10	A-Aminoaryldihydropyridinlactone, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
DE4134760A1 (de)	1993-07-08	Aryl-chinolyl-substituierte 1,4-dihydropyridin-dicarbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
EP0362635A1 (de)	1990-04-11	Verfahren von basischen Nitrophenyl-dihydropyridinamiden als Arzneimittel, neue Verbindungen und Verfahren zu ihrer Herstellung über neue Zwischenprodukte
EP0229963B1 (de)	1991-09-11	4-Thienyl-dihydropyridine, Verfahren zur Herstellung und ihre Verwendung in Arzneimitteln
EP0173943A1 (de)	1986-03-12	Neue Pyridylethyl-Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln