NO893756L - Basiske 4-aryl-dhp-amider, fremgangsmaate til deres fremstilling og deres anvendelse i legemidler. - Google Patents

Basiske 4-aryl-dhp-amider, fremgangsmaate til deres fremstilling og deres anvendelse i legemidler.

Info

Publication number: NO893756L
Authority: NO; Norway
Prior art keywords: carbon atoms; alkyl; substituted; phenyl; halogen
Prior art date: 1988-10-05

Application number

NO89893756A

Other languages

English (en)

Norwegian (no)

Other versions

NO893756D0 (no

Inventor

Juergen Stoltefuss

Eckhard Schwenner

Rainer Gross

Siegbert Hebisch

Matthias Schramm

Martin Bechem

Claudia Hirth

Johannes-Peter Stasch

Original Assignee

Bayer Ag

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.)

1988-10-05

Filing date

1989-09-21

Publication date

1990-04-06

1989-09-21 Application filed by Bayer Ag filed Critical Bayer Ag

1989-09-21 Publication of NO893756D0 publication Critical patent/NO893756D0/no

1990-04-06 Publication of NO893756L publication Critical patent/NO893756L/no

Links

238000000034 method Methods 0.000 title claims description 22
239000003814 drug Substances 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 311
125000000217 alkyl group Chemical group 0.000 claims description 131
-1 hydroxy, cyano, phenyl Chemical group 0.000 claims description 62
229910052736 halogen Chemical group 0.000 claims description 58
150000002367 halogens Chemical group 0.000 claims description 58
125000003545 alkoxy group Chemical group 0.000 claims description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
239000001257 hydrogen Substances 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 52
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 49
125000004093 cyano group Chemical group *C#N 0.000 claims description 42
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 37
150000002431 hydrogen Chemical class 0.000 claims description 34
125000004414 alkyl thio group Chemical group 0.000 claims description 30
229920006395 saturated elastomer Polymers 0.000 claims description 25
125000004663 dialkyl amino group Chemical group 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 21
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000001301 oxygen Substances 0.000 claims description 20
229910052717 sulfur Inorganic materials 0.000 claims description 20
125000003282 alkyl amino group Chemical group 0.000 claims description 19
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 11
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
125000004434 sulfur atom Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229930195734 saturated hydrocarbon Chemical group 0.000 claims description 7
229930195735 unsaturated hydrocarbon Chemical group 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
239000000969 carrier Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
238000004587 chromatography analysis Methods 0.000 claims description 3
206010012601 diabetes mellitus Diseases 0.000 claims description 3
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
125000004970 halomethyl group Chemical group 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
PAWSVPVNIXFKOS-IHWYPQMZSA-N (Z)-2-aminobutenoic acid Chemical class C\C=C(/N)C(O)=O PAWSVPVNIXFKOS-IHWYPQMZSA-N 0.000 claims description 2
206010003445 Ascites Diseases 0.000 claims description 2
208000010412 Glaucoma Diseases 0.000 claims description 2
206010019280 Heart failures Diseases 0.000 claims description 2
208000001647 Renal Insufficiency Diseases 0.000 claims description 2
208000019425 cirrhosis of liver Diseases 0.000 claims description 2
238000002425 crystallisation Methods 0.000 claims description 2
230000008025 crystallization Effects 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims description 2
238000009826 distribution Methods 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
230000033764 rhythmic process Effects 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 4
206010030113 Oedema Diseases 0.000 claims 2
201000010099 disease Diseases 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
229940126601 medicinal product Drugs 0.000 claims 2
206010020772 Hypertension Diseases 0.000 claims 1
GUKKGBSNKJVHDK-NSCUHMNNSA-N N\C(\C(=O)N)=C\C Chemical class N\C(\C(=O)N)=C\C GUKKGBSNKJVHDK-NSCUHMNNSA-N 0.000 claims 1
201000006370 kidney failure Diseases 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000007858 starting material Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
210000003540 papillary muscle Anatomy 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
150000002430 hydrocarbons Chemical group 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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
MZGOEQOUSKNKAR-UHFFFAOYSA-N 2,6-dimethyl-4-(2-phenylmethoxyphenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=CC1C1=CC=CC=C1OCC1=CC=CC=C1 MZGOEQOUSKNKAR-UHFFFAOYSA-N 0.000 description 3
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
230000008602 contraction Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
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229910002027 silica gel Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
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238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
235000013312 flour Nutrition 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
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
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ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
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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
229960000583 acetic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000002969 artificial stone Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
210000005242 cardiac chamber Anatomy 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003599 detergent Substances 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
235000014113 dietary fatty acids Nutrition 0.000 description 1
VQZSDRXKLXBRHJ-UHFFFAOYSA-N diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1 VQZSDRXKLXBRHJ-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
KNUYHVRRBLEIHT-UHFFFAOYSA-N ethyl 3-oxo-5-phenylpent-4-enoate Chemical compound CCOC(=O)CC(=O)C=CC1=CC=CC=C1 KNUYHVRRBLEIHT-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal 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
238000002156 mixing Methods 0.000 description 1
CANONWCJNQBRLK-UHFFFAOYSA-N n-cyclopropyl-3-oxo-5-(2-phenylmethoxyphenyl)pent-4-enamide Chemical compound C1CC1NC(=O)CC(=O)C=CC1=CC=CC=C1OCC1=CC=CC=C1 CANONWCJNQBRLK-UHFFFAOYSA-N 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 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
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000006187 pill Substances 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
229920001592 potato starch Polymers 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011780 sodium chloride Substances 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
238000001228 spectrum Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- 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
- A61P9/06—Antiarrhythmics
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Obesity (AREA)
Gastroenterology & Hepatology (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)

NO89893756A 1988-10-05 1989-09-21 Basiske 4-aryl-dhp-amider, fremgangsmaate til deres fremstilling og deres anvendelse i legemidler. NO893756L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3833892A DE3833892A1 (de)	1988-10-05	1988-10-05	Basische 4-aryl-dhp-amide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln

Publications (2)

Publication Number	Publication Date
NO893756D0 NO893756D0 (no)	1989-09-21
NO893756L true NO893756L (no)	1990-04-06

Family

ID=6364449

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO89893756A NO893756L (no)	1988-10-05	1989-09-21	Basiske 4-aryl-dhp-amider, fremgangsmaate til deres fremstilling og deres anvendelse i legemidler.

Country Status (16)

Country	Link
US (1)	US5015650A (fr)
EP (1)	EP0362632A3 (fr)
JP (1)	JPH02169572A (fr)
KR (1)	KR900006289A (fr)
CN (1)	CN1041758A (fr)
AU (1)	AU616801B2 (fr)
CA (1)	CA2000081A1 (fr)
DD (2)	DD296683A5 (fr)
DE (1)	DE3833892A1 (fr)
DK (1)	DK489889A (fr)
FI (1)	FI894677A7 (fr)
HU (1)	HUT52055A (fr)
IL (1)	IL91863A0 (fr)
NO (1)	NO893756L (fr)
PT (1)	PT91884A (fr)
ZA (1)	ZA897532B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3833893A1 (de) *	1988-10-05	1990-04-12	Bayer Ag	Verwendung von basischen nitro-phenyl-dihydropyridin-amiden als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung ueber neue zwischenprodukte
NL9001752A (nl) *	1990-08-02	1992-03-02	Cedona Pharm Bv	Nieuwe 1,4-dihydropyridinederivaten.
DE4100125A1 (de) *	1991-01-04	1992-07-09	Bayer Ag	Neue dihydropyridinamide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
CN101802593B (zh) *	2007-09-25	2012-06-06	爱科来株式会社	分光测量用压片、其制造方法和分光测量方法
US10513515B2 (en)	2017-08-25	2019-12-24	Biotheryx, Inc.	Ether compounds and uses thereof
CA3106239A1 (fr)	2018-07-27	2020-01-30	Biotheryx, Inc.	Composes bifonctionnels agissant par agonisme sur des cdk
WO2021222150A2 (fr)	2020-04-28	2021-11-04	Anwita Biosciences, Inc.	Polypeptides d'interleukine-2 et protéines de fusion de ceux-ci, ainsi que leurs compositions pharmaceutiques et leurs applications thérapeutiques

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2228377A1 (de) *	1972-06-10	1974-01-03	Bayer Ag	Dihydropyridin-carbonsaeureamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3207982A1 (de) *	1982-03-05	1983-09-08	Bayer Ag, 5090 Leverkusen	Neue 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihrer verwendung in arzneimitteln
DE3445852A1 (de) *	1984-12-15	1986-06-19	Bayer Ag, 5090 Leverkusen	Dihydropyridin-carbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE3521761A1 (de) *	1985-06-19	1987-01-02	Bayer Ag	Neue 1,4-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln
JPS62174050A (ja) *	1985-10-21	1987-07-30	Nippon Shoji Kk	３−アミノカルボニル−１，４−ジヒドロピリジン−５−カルボン酸誘導体、その製法および医薬組成物
DE3601397A1 (de) *	1986-01-18	1987-07-23	Bayer Ag	Substituierte 1,4-dihydropyridin-3-carbonsaeurepiperazide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE3711991A1 (de) *	1987-04-09	1988-10-20	Bayer Ag	Dihydropyridinamide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE3833893A1 (de) *	1988-10-05	1990-04-12	Bayer Ag	Verwendung von basischen nitro-phenyl-dihydropyridin-amiden als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung ueber neue zwischenprodukte

1988
- 1988-10-05 DE DE3833892A patent/DE3833892A1/de not_active Withdrawn
1989
- 1989-09-21 NO NO89893756A patent/NO893756L/no unknown
- 1989-09-21 EP EP19890117494 patent/EP0362632A3/fr not_active Withdrawn
- 1989-09-27 US US07/413,365 patent/US5015650A/en not_active Expired - Fee Related
- 1989-10-03 PT PT91884A patent/PT91884A/pt unknown
- 1989-10-03 CA CA002000081A patent/CA2000081A1/fr not_active Abandoned
- 1989-10-03 DD DD89342972A patent/DD296683A5/de not_active IP Right Cessation
- 1989-10-03 FI FI894677A patent/FI894677A7/fi not_active Application Discontinuation
- 1989-10-03 DD DD89333272A patent/DD297813A5/de not_active IP Right Cessation
- 1989-10-03 IL IL91863A patent/IL91863A0/xx unknown
- 1989-10-04 ZA ZA897532A patent/ZA897532B/xx unknown
- 1989-10-04 KR KR1019890014336A patent/KR900006289A/ko not_active Withdrawn
- 1989-10-04 DK DK489889A patent/DK489889A/da not_active Application Discontinuation
- 1989-10-05 AU AU42609/89A patent/AU616801B2/en not_active Expired - Fee Related
- 1989-10-05 HU HU895229A patent/HUT52055A/hu unknown
- 1989-10-05 CN CN89107734A patent/CN1041758A/zh active Pending
- 1989-10-05 JP JP1258935A patent/JPH02169572A/ja active Pending

Also Published As

Publication number	Publication date
ZA897532B (en)	1990-06-27
AU616801B2 (en)	1991-11-07
DK489889A (da)	1990-04-06
DD296683A5 (de)	1991-12-12
KR900006289A (ko)	1990-05-07
EP0362632A3 (fr)	1990-11-07
US5015650A (en)	1991-05-14
NO893756D0 (no)	1989-09-21
DK489889D0 (da)	1989-10-04
DD297813A5 (de)	1992-01-23
CN1041758A (zh)	1990-05-02
FI894677A7 (fi)	1990-04-06
CA2000081A1 (fr)	1990-04-05
EP0362632A2 (fr)	1990-04-11
JPH02169572A (ja)	1990-06-29
IL91863A0 (en)	1990-06-10
DE3833892A1 (de)	1990-04-12
AU4260989A (en)	1990-04-12
HUT52055A (en)	1990-06-28
PT91884A (pt)	1990-04-30
FI894677A0 (fi)	1989-10-03

Publication	Publication Date	Title
NO159928B (no)	1988-11-14	Fremgangsmaate til fremstilling av optisk aktive 1-,4-dihydropyridinkarboksylsyreestere.
DK170891B1 (da)	1996-03-04	1,4-dihydropyridin-3,5-dicarboxylsyrederivater og fremgangsmåde til fremstilling deraf samt farmaceutisk middel indeholdende dem
US4822798A (en)	1989-04-18	Circulation-active 4-phenyl-6-substituted dihydropyrimidines
FR2511247A1 (fr)	1983-02-18	Dihydropyridines ayant une action positivement inotrope, leur utilisation comme medicaments et un procede pour leur preparation
PL140573B1 (en)	1987-05-30	Method of obtaining new dihydropyridine derivatives
EP0296316A1 (fr)	1988-12-28	Enantiomères de dihydro-1,4-pyridine
JPH0676380B2 (ja)	1994-09-28	新規な１，４−ジヒドロピリジン類
HU204786B (en)	1992-02-28	Process for producing new dihydropyridine amide derivatives and pharmaceutical compositions comprising such compounds
US5015650A (en)	1991-05-14	Circulation-active basic 4-aryl-DHP amides
EP0234196A1 (fr)	1987-09-02	Pipérazides d'acide 1,4-dihydropyridine-3-carboxylique, procédé pour leur préparation et leur utilisation dans des médicaments
NO854021L (no)	1986-04-28	1,4-dihydropyridin-hydroksyaminer og fremgangsmaate til fremstilling derav.
US5064839A (en)	1991-11-12	1,4-dihydropyridines with a 2-amino group or with an ether group in a side chain
NO893757L (no)	1990-04-06	Anvendelse av basiske nitro-fenyl-dihydropyridinamider som legemidler, nye forbindelser og fremgangsmaater til deresfremstilling via nye mellomprodukter.
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