JPH0153245B2 - - Google Patents
Info
- Publication number
- JPH0153245B2 JPH0153245B2 JP55182854A JP18285480A JPH0153245B2 JP H0153245 B2 JPH0153245 B2 JP H0153245B2 JP 55182854 A JP55182854 A JP 55182854A JP 18285480 A JP18285480 A JP 18285480A JP H0153245 B2 JPH0153245 B2 JP H0153245B2
- Authority
- JP
- Japan
- Prior art keywords
- circulatory system
- system disease
- compound
- therapeutic agent
- benzopyran
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000003814 drug Substances 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 16
- 229940124597 therapeutic agent Drugs 0.000 claims description 10
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 230000006793 arrhythmia Effects 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010034567 Peripheral circulatory failure Diseases 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 42
- 229940079593 drug Drugs 0.000 description 17
- 230000036772 blood pressure Effects 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 230000017531 blood circulation Effects 0.000 description 11
- 230000007423 decrease Effects 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 230000000747 cardiac effect Effects 0.000 description 7
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 7
- 230000002861 ventricular Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 235000010980 cellulose Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- 230000001052 transient effect Effects 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 5
- 239000001913 cellulose Substances 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000001631 hypertensive effect Effects 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 230000002792 vascular Effects 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 206010062575 Muscle contracture Diseases 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 208000006111 contracture Diseases 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000002459 sustained effect Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000282465 Canis Species 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 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 3
- 210000001367 artery Anatomy 0.000 description 3
- 239000002876 beta blocker Substances 0.000 description 3
- 229940097320 beta blocking agent Drugs 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 229940105329 carboxymethylcellulose Drugs 0.000 description 3
- 210000001168 carotid artery common Anatomy 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000003804 effect on potassium Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 229940039009 isoproterenol Drugs 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- -1 sorbitan fatty acid ester Chemical class 0.000 description 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-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
- 229920002261 Corn starch Polymers 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000001746 atrial effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 210000000621 bronchi Anatomy 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 210000003975 mesenteric artery Anatomy 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 230000036581 peripheral resistance Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 210000003240 portal vein Anatomy 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000002254 renal artery Anatomy 0.000 description 2
- 210000003752 saphenous vein Anatomy 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- AEGZSOBDIZYPGN-UHFFFAOYSA-N 3-(hydroxymethyl)-3,4-dihydro-2h-chromen-8-ol Chemical compound C1=CC=C2CC(CO)COC2=C1O AEGZSOBDIZYPGN-UHFFFAOYSA-N 0.000 description 1
- MEAPRSDUXBHXGD-UHFFFAOYSA-N 3-chloro-n-(4-propan-2-ylphenyl)propanamide Chemical compound CC(C)C1=CC=C(NC(=O)CCCl)C=C1 MEAPRSDUXBHXGD-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 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 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 230000008321 arterial blood flow Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 229960001714 calcium phosphate Drugs 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229940095672 calcium sulfate Drugs 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AVLIGBBBDNWHFL-UHFFFAOYSA-N ethyl (3-hydroxy-3,4-dihydro-2h-chromen-8-yl) carbonate Chemical compound C1C(O)COC2=C1C=CC=C2OC(=O)OCC AVLIGBBBDNWHFL-UHFFFAOYSA-N 0.000 description 1
- LNOFDINSFMGNGX-UHFFFAOYSA-N ethyl [3-(hydroxymethyl)-3,4-dihydro-2h-chromen-8-yl] carbonate Chemical compound C1C(CO)COC2=C1C=CC=C2OC(=O)OCC LNOFDINSFMGNGX-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004503 fine granule 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
- 208000019622 heart disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011976 maleic acid 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
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 238000011170 pharmaceutical development Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960004604 propranolol hydrochloride Drugs 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol hydrochloride Natural products C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 230000035485 pulse pressure Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000008327 renal blood flow Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
- 229960004813 trichlormethiazide Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55182854A JPS57106619A (en) | 1980-12-25 | 1980-12-25 | Remedy for circulatory disease |
| US06/271,927 US4394382A (en) | 1980-06-17 | 1981-06-09 | Dihydrobenzopyran compounds and pharmaceutical composition comprising said compounds |
| AU71652/81A AU543347B2 (en) | 1980-06-17 | 1981-06-11 | Benzopyrans |
| CA000379656A CA1178598A (en) | 1980-06-17 | 1981-06-12 | Benzopyran compound, process for production thereof, and pharmaceutical composition comprising said compound |
| IE1312/81A IE52067B1 (en) | 1980-06-17 | 1981-06-12 | Benzopyrans,their production and pharmaceutical compositions containing them |
| FI811856A FI79307C (fi) | 1980-06-17 | 1981-06-15 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 3,4-dihydro-8-(2-hydroxi-3-alkylamino)propoxi-2h- 1-bensopyranderivat. |
| MX10178081U MX6885E (es) | 1980-06-17 | 1981-06-16 | Procedimiento para preparar compuestos de dihidrobenzopirano |
| ES503091A ES503091A0 (es) | 1980-06-17 | 1981-06-16 | Un procedimiento para obtener derivados de benzopirano |
| SU813300799A SU1212325A3 (ru) | 1980-06-17 | 1981-06-16 | Способ получени производных бензопирана |
| AT81302700T ATE9582T1 (de) | 1980-06-17 | 1981-06-16 | Benzopyrane, ihre herstellung und sie enthaltende pharmazeutische zusammensetzungen. |
| CS814509A CS226731B2 (en) | 1980-06-17 | 1981-06-16 | Method of preparing benzopyrane compounds |
| DE8181302700T DE3166300D1 (en) | 1980-06-17 | 1981-06-16 | Benzopyrans, their production and pharmaceutical compositions containing them |
| NO812042A NO154495C (no) | 1980-06-17 | 1981-06-16 | Analogifremgangsmaate for fremstilling av en benzopyranforbindelse. |
| ZA814042A ZA814042B (en) | 1980-06-17 | 1981-06-16 | Benzopyran compound,process for production thereof,and pharmaceutical composition comprising said compound |
| KR1019810002196A KR850000193B1 (ko) | 1980-06-17 | 1981-06-16 | 벤조피란 화합물의 제조방법 |
| DK264181A DK154557C (da) | 1980-06-17 | 1981-06-16 | Analogifremgangsmaade til fremstilling af 3,4-dihydro-8-((2-hydroxy-3-alkylamino)-propoxy)-2h-1-benzopyranderivater eller et farmaceutisk acceptabelt syreadditionssalt deraf |
| EP81302700A EP0042299B1 (en) | 1980-06-17 | 1981-06-16 | Benzopyrans, their production and pharmaceutical compositions containing them |
| PL1981231734A PL130537B1 (en) | 1980-06-17 | 1981-06-17 | Method of manufacture of novel aminoalcohols,derivative of benzopyrane |
| DD81230894A DD160453A5 (de) | 1980-06-17 | 1981-06-17 | Verfahren zur herstellung von benzopyranverbindungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55182854A JPS57106619A (en) | 1980-12-25 | 1980-12-25 | Remedy for circulatory disease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57106619A JPS57106619A (en) | 1982-07-02 |
| JPH0153245B2 true JPH0153245B2 (ru) | 1989-11-13 |
Family
ID=16125610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55182854A Granted JPS57106619A (en) | 1980-06-17 | 1980-12-25 | Remedy for circulatory disease |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57106619A (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60208973A (ja) * | 1984-03-31 | 1985-10-21 | Kowa Co | 循環系疾患治療剤 |
| WO2004037246A1 (ja) * | 2002-10-24 | 2004-05-06 | Kowa Co., Ltd. | 神経線維再生促進剤 |
| JP4587374B2 (ja) * | 2004-12-27 | 2010-11-24 | 株式会社トクヤマ | 硝酸エステルの製造方法 |
| JP4749759B2 (ja) * | 2005-05-12 | 2011-08-17 | 株式会社トクヤマ | ジヒドロベンゾピラン化合物の製造方法 |
| JP2007145755A (ja) * | 2005-11-28 | 2007-06-14 | Tokuyama Corp | ８位に水酸基を有するベンゾピラン化合物の製造方法 |
-
1980
- 1980-12-25 JP JP55182854A patent/JPS57106619A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57106619A (en) | 1982-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8017786B2 (en) | Substituted β-phenyl-α-hydroxy-propanoic acid, synthesis method and use thereof | |
| JP6324956B2 (ja) | 置換アミノインダン−およびアミノテトラリンカルボン酸ならびにその使用 | |
| BG61420B2 (bg) | 3-метилов естер 5-етилов естер на 2,6-диметил-4-(2,3- дихлорофенил)-1,4-дихидропиридин-3,5-дикарбоксиловата киселина,притежаващ хипотензивни свойства,метод за неговото получаване и фармацевтични пре парати, които ги съдържат | |
| SU1212325A3 (ru) | Способ получени производных бензопирана | |
| US4416893A (en) | Substituted 1,2,5-oxadiazole-2-oxides in human cardiovascular system disease | |
| JPS6217972B2 (ru) | ||
| KR880001428B1 (ko) | 치환된 3-아미노-시드논-이민의 제조방법 | |
| JP2628756B2 (ja) | 新規有機ニトレート及びそれらの製造方法 | |
| JPH0153245B2 (ru) | ||
| WO1998027982A1 (fr) | Composition contenant de l'acide ascorbique | |
| JP2008506722A (ja) | シス−１，２−置換スチルベン誘導体、および糖尿病の治療および／または予防のための薬剤の製造におけるそれらの使用 | |
| JPH0143723B2 (ru) | ||
| JPH0138089B2 (ru) | ||
| CN106432159A (zh) | 一种新型苯并呋喃类衍生物、其制备方法和应用 | |
| CN101805336B (zh) | 一类含色氨酸和异恶唑骨架的化合物、其制备方法和用途 | |
| JP3049816B2 (ja) | 強心薬 | |
| JPH05194394A (ja) | ３−ホルミル−１，４−ジヒドロピリジン類を含有する薬剤 | |
| CS208731B2 (en) | Method of making the new amines | |
| CN101805337B (zh) | 一类含脯氨酸和异恶唑骨架的化合物、其制备方法和用途 | |
| JPH0535150B2 (ru) | ||
| US4678796A (en) | 2-alkylidene derivatives of 1,2,3,4-tetrahydropyridine-2,5-pyridine carboxylic acid dialkyl esters useful for treatment of cardiovascular disorders | |
| JP2528465B2 (ja) | ３−アミノ−ジヒドロピリジン類 | |
| CN103304502B (zh) | 一类抗糖尿病化合物、其制备方法和用途 | |
| US5846967A (en) | Natriuretic and anti-hypertensive compounds | |
| JPS61277650A (ja) | ７−オキソ−ｐｇｉ２エフエドリン塩類似体，その製造方法および医薬組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |