CA1063516A - Pharmaceutical preparations for the treatment of coronary heart diseases - Google Patents
Pharmaceutical preparations for the treatment of coronary heart diseasesInfo
- Publication number
- CA1063516A CA1063516A CA242,899A CA242899A CA1063516A CA 1063516 A CA1063516 A CA 1063516A CA 242899 A CA242899 A CA 242899A CA 1063516 A CA1063516 A CA 1063516A
- Authority
- CA
- Canada
- Prior art keywords
- propanol
- isopropylamino
- phenyl
- used pharmaceutically
- acid addition
- 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
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 45
- 208000029078 coronary artery disease Diseases 0.000 title claims abstract description 12
- 238000011282 treatment Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 210000001772 blood platelet Anatomy 0.000 claims abstract description 33
- -1 N-substituted dibenzazepine Chemical class 0.000 claims description 163
- 150000003839 salts Chemical class 0.000 claims description 106
- 239000002253 acid Substances 0.000 claims description 67
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 239000003826 tablet Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 32
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000002775 capsule Substances 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000008298 dragée Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 claims description 7
- NXQMNKUGGYNLBY-UHFFFAOYSA-N toliprolol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=C1 NXQMNKUGGYNLBY-UHFFFAOYSA-N 0.000 claims description 7
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 claims description 3
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 3
- DZOHUCWRMSCLCN-UHFFFAOYSA-N 1-(1H-indol-4-yloxy)-3-(propan-2-ylamino)propan-1-ol Chemical compound CC(C)NCCC(O)Oc1cccc2[nH]ccc12 DZOHUCWRMSCLCN-UHFFFAOYSA-N 0.000 claims description 2
- GZDBSFAQFPWZFV-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-4-yloxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1CCC2 GZDBSFAQFPWZFV-UHFFFAOYSA-N 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 claims description 2
- 229960003133 ergot alkaloid Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- NXWGWUVGUSFQJC-UHFFFAOYSA-N mepindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=C(C)N2 NXWGWUVGUSFQJC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 239000003087 receptor blocking agent Substances 0.000 abstract 1
- 229960004592 isopropanol Drugs 0.000 description 46
- 238000007792 addition Methods 0.000 description 34
- 150000003254 radicals Chemical class 0.000 description 31
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 28
- 239000002585 base Substances 0.000 description 24
- 230000006870 function Effects 0.000 description 17
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- 235000019759 Maize starch Nutrition 0.000 description 15
- 235000019359 magnesium stearate Nutrition 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 229920002472 Starch Polymers 0.000 description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
- 239000008187 granular material Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 230000009471 action Effects 0.000 description 9
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 239000004922 lacquer Substances 0.000 description 9
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- 239000001828 Gelatine Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000005237 alkyleneamino group Chemical group 0.000 description 8
- 229920000159 gelatin Polymers 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000008119 colloidal silica Substances 0.000 description 7
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 7
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 7
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 7
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 7
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000005281 alkyl ureido group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- TUEJFGFQYKDAPM-UHFFFAOYSA-N 3-[n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-4-methylanilino]phenol;hydron;chloride Chemical compound Cl.C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 TUEJFGFQYKDAPM-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000001589 carboacyl group Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 235000015424 sodium Nutrition 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 235000012222 talc Nutrition 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 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 4
- 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 4
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000005236 alkanoylamino group Chemical group 0.000 description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- UFLVPYQUIGXQNW-UHFFFAOYSA-N 1-(3-methylphenoxy)-3-(propan-2-ylamino)propan-2-ol;hydrochloride Chemical compound Cl.CC(C)NCC(O)COC1=CC=CC(C)=C1 UFLVPYQUIGXQNW-UHFFFAOYSA-N 0.000 description 3
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- 125000002947 alkylene group Chemical group 0.000 description 3
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- 229960004290 dihydroergocornine Drugs 0.000 description 1
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- 229960004704 dihydroergotamine Drugs 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
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- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
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- 230000002107 myocardial effect Effects 0.000 description 1
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- WEHBLOLHUXXQND-UHFFFAOYSA-N n-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]methanesulfonamide Chemical compound CC(C)NCC(O)COC1=CC=C(NS(C)(=O)=O)C=C1 WEHBLOLHUXXQND-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 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
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical class C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000000264 venule Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
- A61K31/621—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate having the hydroxy group in position 2 esterified, e.g. benorylate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/625—Salicylic acid; Derivatives thereof having heterocyclic substituents, e.g. 4-salicycloylmorpholine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7175 | 1975-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1063516A true CA1063516A (en) | 1979-10-02 |
Family
ID=4178628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA242,899A Expired CA1063516A (en) | 1975-01-06 | 1976-01-02 | Pharmaceutical preparations for the treatment of coronary heart diseases |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5191337A (cs) |
| AU (1) | AU499140B2 (cs) |
| BE (1) | BE837293A (cs) |
| CA (1) | CA1063516A (cs) |
| DE (1) | DE2600069A1 (cs) |
| FR (1) | FR2296430A1 (cs) |
| GB (1) | GB1510370A (cs) |
| HK (1) | HK49680A (cs) |
| IE (1) | IE42766B1 (cs) |
| IL (1) | IL48785A (cs) |
| MY (1) | MY8100159A (cs) |
| NL (1) | NL7600045A (cs) |
| NZ (1) | NZ179623A (cs) |
| ZA (2) | ZA7628B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5981563A (en) * | 1995-04-28 | 1999-11-09 | Zonagen, Inc. | Methods and formulations for modulating the human sexual response |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019006A1 (de) * | 1979-05-14 | 1980-11-26 | Ciba-Geigy Ag | Pharmazeutische Präparate, die als Wirkstoff ein substituiertes Pyrazolidinderivat enthalten, deren Verwendung und Verfahren zu ihrer Herstellung |
| FR2470599A1 (fr) * | 1979-12-07 | 1981-06-12 | Panoz Donald | Perfectionnements apportes aux procedes de preparation de formes galeniques a action retard et a liberation programmee et formes galeniques de medicaments ainsi obtenus |
| TW284688B (cs) * | 1991-11-20 | 1996-09-01 | Takeda Pharm Industry Co Ltd |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL37700A (en) * | 1970-10-02 | 1975-05-22 | Ciba Geigy Ag | Pharmaceutical preparations containing an aryloxypropanolamine derivative or an arylethanolamine derivative |
-
1975
- 1975-12-22 NZ NZ179623A patent/NZ179623A/xx unknown
- 1975-12-31 GB GB53300/75A patent/GB1510370A/en not_active Expired
-
1976
- 1976-01-02 CA CA242,899A patent/CA1063516A/en not_active Expired
- 1976-01-02 FR FR7600016A patent/FR2296430A1/fr active Granted
- 1976-01-02 DE DE19762600069 patent/DE2600069A1/de not_active Withdrawn
- 1976-01-05 IE IE11/76A patent/IE42766B1/en unknown
- 1976-01-05 BE BE163295A patent/BE837293A/xx unknown
- 1976-01-05 AU AU10002/76A patent/AU499140B2/en not_active Expired
- 1976-01-05 NL NL7600045A patent/NL7600045A/xx not_active Application Discontinuation
- 1976-01-05 IL IL48785A patent/IL48785A/xx unknown
- 1976-01-05 ZA ZA00760028A patent/ZA7628B/xx unknown
- 1976-01-05 ZA ZA00760026A patent/ZA7626B/xx unknown
- 1976-01-06 JP JP51000124A patent/JPS5191337A/ja active Pending
-
1980
- 1980-09-04 HK HK496/80A patent/HK49680A/xx unknown
-
1981
- 1981-12-30 MY MY159/81A patent/MY8100159A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5981563A (en) * | 1995-04-28 | 1999-11-09 | Zonagen, Inc. | Methods and formulations for modulating the human sexual response |
| US6051594A (en) * | 1995-04-28 | 2000-04-18 | Zonagen, Inc. | Methods and formulations for modulating the human sexual response |
| US6100286A (en) * | 1995-04-28 | 2000-08-08 | Zonagen, Inc. | Methods and formulations for modulating the human sexual response |
| US6124337A (en) * | 1995-04-28 | 2000-09-26 | Zonagen, Inc. | Methods and formulations for modulating the human sexual response |
| US6166061A (en) * | 1995-04-28 | 2000-12-26 | Zonagen, Inc. | Methods and formulations for modulating the human sexual response |
Also Published As
| Publication number | Publication date |
|---|---|
| HK49680A (en) | 1980-09-12 |
| IE42766L (en) | 1976-07-06 |
| ZA7626B (en) | 1976-12-29 |
| JPS5191337A (cs) | 1976-08-10 |
| IL48785A0 (en) | 1976-03-31 |
| IL48785A (en) | 1978-08-31 |
| NL7600045A (nl) | 1976-07-08 |
| AU499140B2 (en) | 1979-04-05 |
| ZA7628B (en) | 1976-12-29 |
| AU1000276A (en) | 1977-07-14 |
| IE42766B1 (en) | 1980-10-08 |
| MY8100159A (en) | 1981-12-31 |
| BE837293A (fr) | 1976-07-05 |
| GB1510370A (en) | 1978-05-10 |
| FR2296430B1 (cs) | 1978-11-10 |
| FR2296430A1 (fr) | 1976-07-30 |
| NZ179623A (en) | 1978-03-06 |
| DE2600069A1 (de) | 1976-07-15 |
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