NO861422L - Nye 1,4-dihydropyridin-3,5-dikarboksylat-derivater. - Google Patents

Nye 1,4-dihydropyridin-3,5-dikarboksylat-derivater.

Info

Publication number: NO861422L
Authority: NO; Norway
Prior art keywords: dihydropyridine; dicarboxylate; ethyl; dimethyl; imidazolyl
Prior art date: 1984-08-14

Application number

NO861422A

Other languages

English (en)

Norwegian (no)

Inventor

Noboru Shimizu

Hiroyuki Ishiwata

Tomio Ohta

Hiroshi Ishihama

Yasumi Uchida

Original Assignee

Kowa Co

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.)

1984-08-14

Filing date

1986-04-11

Publication date

1986-04-11

1986-04-11 Application filed by Kowa Co filed Critical Kowa Co

1986-04-11 Publication of NO861422L publication Critical patent/NO861422L/no

Links

COLPLFZHPXIFCQ-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=CNC=C(C(O)=O)C1 COLPLFZHPXIFCQ-UHFFFAOYSA-N 0.000 title claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000003709 fluoroalkyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 48
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 28
-1 alkali metal salt Chemical class 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000843 powder Substances 0.000 description 22
238000000034 method Methods 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
238000010898 silica gel chromatography Methods 0.000 description 12
239000000243 solution Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000007788 liquid Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000010410 layer Substances 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
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VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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239000007858 starting material Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QEJRVNUQRBDENC-UHFFFAOYSA-N 3-(3-oxobutanoyloxy)propyl 4-(2-imidazol-1-ylethoxy)benzoate Chemical compound C1=CC(C(=O)OCCCOC(=O)CC(=O)C)=CC=C1OCCN1C=NC=C1 QEJRVNUQRBDENC-UHFFFAOYSA-N 0.000 description 2
CDXHJKXBTXGRRU-UHFFFAOYSA-N 3-[2-[(3-nitrophenyl)methylidene]-3-oxobutanoyl]oxypropyl 4-(2-imidazol-1-ylethoxy)benzoate Chemical compound C=1C=C(OCCN2C=NC=C2)C=CC=1C(=O)OCCCOC(=O)C(C(=O)C)=CC1=CC=CC([N+]([O-])=O)=C1 CDXHJKXBTXGRRU-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
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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206010022998 Irritability Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
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 2
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239000002253 acid Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
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OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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235000010980 cellulose Nutrition 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
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YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 2
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
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229960001783 nicardipine Drugs 0.000 description 2
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 2
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210000004623 platelet-rich plasma Anatomy 0.000 description 2
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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235000017557 sodium bicarbonate Nutrition 0.000 description 2
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
229940124549 vasodilator Drugs 0.000 description 2
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FMNQRUKVXAQEAZ-JNRFBPFXSA-N (5z,8s,9r,10e,12s)-9,12-dihydroxy-8-[(1s)-1-hydroxy-3-oxopropyl]heptadeca-5,10-dienoic acid Chemical compound CCCCC[C@H](O)\C=C\[C@@H](O)[C@H]([C@@H](O)CC=O)C\C=C/CCCC(O)=O FMNQRUKVXAQEAZ-JNRFBPFXSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
TZDPJNSHSWMCPN-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 TZDPJNSHSWMCPN-UHFFFAOYSA-N 0.000 description 1
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
IZKVATMDIVGOQU-UHFFFAOYSA-N 2-hydroxyethyl 4-(1h-imidazol-2-ylmethyl)benzoate Chemical compound C1=CC(C(=O)OCCO)=CC=C1CC1=NC=CN1 IZKVATMDIVGOQU-UHFFFAOYSA-N 0.000 description 1
ZBBXVXQWKNEZKK-UHFFFAOYSA-N 3-[4-(1h-imidazol-2-ylmethyl)phenyl]prop-2-enoic acid Chemical compound C1=CC(C=CC(=O)O)=CC=C1CC1=NC=CN1 ZBBXVXQWKNEZKK-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
JWCVQIPCIUVNAV-UHFFFAOYSA-N 3-hydroxypropyl 4-(2-imidazol-1-ylethoxy)benzoate Chemical compound C1=CC(C(=O)OCCCO)=CC=C1OCCN1C=NC=C1 JWCVQIPCIUVNAV-UHFFFAOYSA-N 0.000 description 1
GLRLMJNACGUDGD-UHFFFAOYSA-N 3-o-ethyl 5-o-[3-[4-(2-imidazol-1-ylethoxy)benzoyl]oxypropyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC(=O)C=2C=CC(OCCN3C=NC=C3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 GLRLMJNACGUDGD-UHFFFAOYSA-N 0.000 description 1
MPOOHAOWKYTUQT-UHFFFAOYSA-N 5-ethoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 MPOOHAOWKYTUQT-UHFFFAOYSA-N 0.000 description 1
LWOUADUQEXXXAB-UHFFFAOYSA-N 5-methoxycarbonyl-1-(methoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-4h-pyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)N(COC)C(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 LWOUADUQEXXXAB-UHFFFAOYSA-N 0.000 description 1
PDDOVTTYZAVEGT-UHFFFAOYSA-N 5-o-[2-(6-imidazol-1-ylhexanoyloxy)ethyl] 3-o-methyl 1-(methoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-4h-pyridine-3,5-dicarboxylate Chemical compound CC=1N(COC)C(C)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCOC(=O)CCCCCN1C=CN=C1 PDDOVTTYZAVEGT-UHFFFAOYSA-N 0.000 description 1
NVRVNSHHLPQGCU-UHFFFAOYSA-N 6-bromohexanoic acid Chemical compound OC(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-N 0.000 description 1
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239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
XQGZSYKGWHUSDH-UHFFFAOYSA-N dazoxiben Chemical compound C1=CC(C(=O)O)=CC=C1OCCN1C=NC=C1 XQGZSYKGWHUSDH-UHFFFAOYSA-N 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
239000012458 free base Substances 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
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
150000007522 mineralic acids Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920000223 polyglycerol 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
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 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
239000000600 sorbitol Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
150000003595 thromboxanes Chemical class 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

NO861422A 1984-08-14 1986-04-11 Nye 1,4-dihydropyridin-3,5-dikarboksylat-derivater. NO861422L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59169588A JPS6147477A (ja)	1984-08-14	1984-08-14	新規１，４−ジヒドロピリジン−３，５−ジカルボン酸エステル誘導体

Publications (1)

Publication Number	Publication Date
NO861422L true NO861422L (no)	1986-04-11

Family

ID=15889265

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO861422A NO861422L (no)	1984-08-14	1986-04-11	Nye 1,4-dihydropyridin-3,5-dikarboksylat-derivater.

Country Status (10)

Country	Link
US (1)	US4737506A (da)
EP (1)	EP0190364A4 (da)
JP (1)	JPS6147477A (da)
KR (1)	KR860700252A (da)
AU (1)	AU577152B2 (da)
DK (1)	DK165686A (da)
ES (3)	ES8707185A1 (da)
HU (1)	HU195500B (da)
NO (1)	NO861422L (da)
WO (1)	WO1986001206A1 (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0379579A4 (en) *	1988-02-03	1991-01-02	Yoshitomi Pharmaceutical Industries, Ltd.	Pharmaceutical composition having improved releasability
JPH03504014A (ja) *	1989-02-17	1991-09-05	インスティテュト　オルガニチェスコゴ　シンテザ　アカデミイ　ナウク　ラトビイスコイ　エスエスアール	２‐（２，６‐ジメチル‐３，５‐ジエトキシカルボニル―１，４‐ジヒドロピリジン‐４‐カルボキサミド）エタンスルホン酸のアルカリ塩の調製方法
DE69129918T2 (de) *	1990-03-23	1999-02-04	Yoshitomi Pharmaceutical	Ein in Wasser schwerlösliches Arzneimittel enthaltende pharmazeutische Zubereitung
DE4233347A1 (de) *	1992-10-05	1994-04-07	Bayer Ag	Dihydropyridin-alkoxy- und -alkylamino-aroylester
DE69630465T2 (de)	1995-12-27	2004-07-22	Mitsubishi Pharma Corp.	Vorsorge-/heilmittel fur die komplikationen von diabetes

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2218644C3 (de) *	1972-04-18	1982-08-19	Bayer Ag, 5090 Leverkusen	Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
JPS5720953B2 (da) *	1974-04-18	1982-05-04
JPS575790B2 (da) *	1974-04-25	1982-02-01
DE2747513A1 (de) *	1977-10-22	1979-05-03	Bayer Ag	Dihydropyridine mit schwefelhaltigen estergruppierungen
DE2847236A1 (de) *	1978-10-31	1980-05-14	Bayer Ag	Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
JPS56140989A (en) *	1980-04-03	1981-11-04	Yoshitomi Pharmaceut Ind Ltd	1,4-dihydrophyridine-3,5-dicarboxylic ester derivative or its salt
JPS57200386A (en) *	1981-06-04	1982-12-08	Yoshitomi Pharmaceut Ind Ltd	Novel 1,4-dihydropyridine-3,5-dicarboxylic ester derivative and its salts
JPS58131982A (ja) *	1982-02-01	1983-08-06	Tokyo Tanabe Co Ltd	新規なる１．４−ジヒドロピリジン誘導体
US4656181A (en) *	1982-11-24	1987-04-07	Cermol S.A.	Esters of 1,4-dihydropyridines, processes for the preparation of the new esters, and medicaments containing the same
JPS60215684A (ja) *	1984-04-11	1985-10-29	Toyama Chem Co Ltd	新規な１，４−ジヒドロピリジン誘導体およびその塩類

1984
- 1984-08-14 JP JP59169588A patent/JPS6147477A/ja active Granted
1985
- 1985-08-12 EP EP19850904021 patent/EP0190364A4/en not_active Withdrawn
- 1985-08-12 AU AU47217/85A patent/AU577152B2/en not_active Ceased
- 1985-08-12 KR KR860700209A patent/KR860700252A/ko not_active Application Discontinuation
- 1985-08-12 US US06/851,134 patent/US4737506A/en not_active Expired - Fee Related
- 1985-08-12 HU HU853611A patent/HU195500B/hu not_active IP Right Cessation
- 1985-08-12 WO PCT/JP1985/000449 patent/WO1986001206A1/ja not_active Application Discontinuation
- 1985-08-14 ES ES546136A patent/ES8707185A1/es not_active Expired
1986
- 1986-04-11 DK DK165686A patent/DK165686A/da not_active IP Right Cessation
- 1986-04-11 NO NO861422A patent/NO861422L/no unknown
1987
- 1987-02-09 ES ES557371A patent/ES8802512A1/es not_active Expired
- 1987-02-09 ES ES557372A patent/ES8801206A1/es not_active Expired

Also Published As

Publication number	Publication date
ES8707185A1 (es)	1987-07-16
EP0190364A4 (en)	1987-02-12
ES8802512A1 (es)	1988-06-16
US4737506A (en)	1988-04-12
DK165686D0 (da)	1986-04-11
ES8801206A1 (es)	1988-01-01
HUT40644A (en)	1987-01-28
EP0190364A1 (en)	1986-08-13
ES546136A0 (es)	1987-07-16
JPS6147477A (ja)	1986-03-07
DK165686A (da)	1986-04-11
JPH0374666B2 (da)	1991-11-27
HU195500B (en)	1988-05-30
AU577152B2 (en)	1988-09-15
ES557372A0 (es)	1988-01-01
AU4721785A (en)	1986-03-07
KR860700252A (ko)	1986-08-01
ES557371A0 (es)	1988-06-16
WO1986001206A1 (en)	1986-02-27

Publication	Publication Date	Title
KR880002357B1 (ko)	1988-10-29	디히드로피리딘 유도체의 제조방법
DK170891B1 (da)	1996-03-04	1,4-dihydropyridin-3,5-dicarboxylsyrederivater og fremgangsmåde til fremstilling deraf samt farmaceutisk middel indeholdende dem
US4952689A (en)	1990-08-28	3-(substituted propylidene)-2-azetidinone derivates for blood platelet aggregation
EP0233228A1 (en)	1987-08-26	Pharmaceutically active 2-thiomethyl-substituted-1,4-dihydropyridines
DK158307B (da)	1990-04-30	Analogifremgangsmaade til fremstilling af 4-(fenylalkyl)-imidazolderivater eller farmaceutisk acceptable syreadditionssalte deraf
US5891895A (en)	1999-04-06	Hydroxypyridine derivatives their production and use
CA1215050A (en)	1986-12-09	Dihydropyridines
US4713387A (en)	1987-12-15	Vasodilating and platelet aggregation inhibiting 1,4 dihydropyridines with an imidazolyl or pyridyl containing ester
EP0172029B1 (en)	1991-02-27	1,4-dihydropyridines
CA2104456C (en)	1996-12-10	Pyridine- and imidazole-derived agents for cardiovascular diseases
US5332833A (en)	1994-07-26	β-oxo-β-benzenepropanethioamide compounds
NO861422L (no)	1986-04-11	Nye 1,4-dihydropyridin-3,5-dikarboksylat-derivater.
JPS6025423B2 (ja)	1985-06-18	１，４−ジヒドロピリジンの製法
US4703051A (en)	1987-10-27	4,7-dihydrothieno[2,3-B]pyridine derivatives useful in the treatment of cardiovascular diseases
US4892881A (en)	1990-01-09	Dihydropyridine anti-ischaemic and antihypertensive agents
US5968967A (en)	1999-10-19	Pyrazolones derivatives
EP0257616B1 (en)	1992-10-28	Dihydropyridine derivates and pharmaceutical composition thereof
US4985558A (en)	1991-01-15	1,4-dihydropyridine derivative
US4886819A (en)	1989-12-12	Dihydropyridine derivatives and pharmaceutical composition thereof
US5100892A (en)	1992-03-31	Dihydropyridine vasodilator agents
KR930001404B1 (ko)	1993-02-27	디아릴 화합물의 제조방법
NO166642B (no)	1991-05-13	Anaolgifremgangsmaate for fremstilling av terapeutisk aktive 3-aryl-5-alkylthio-4h-1,2,4-triazoler.
JPS6328068B2 (da)	1988-06-07
US5258519A (en)	1993-11-02	Dihydropyridine vasodilators agents
JPH01168683A (ja)	1989-07-04	新規な置換ニトロジヒドロピリジン、その製造法、及びその使用