CA1080237A - 2-benzopyranone derivatives, method for their manufacture and their use as medicaments - Google Patents
2-benzopyranone derivatives, method for their manufacture and their use as medicamentsInfo
- Publication number
- CA1080237A CA1080237A CA256,404A CA256404A CA1080237A CA 1080237 A CA1080237 A CA 1080237A CA 256404 A CA256404 A CA 256404A CA 1080237 A CA1080237 A CA 1080237A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- oxo
- benzopyran
- propyl
- urea
- 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
- 238000000034 method Methods 0.000 title claims abstract description 65
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title abstract description 6
- 239000003814 drug Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 3,4,5-trimethoxybenzoyl group Chemical group 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 67
- 239000000126 substance Substances 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- QVQGTNFYPJQJNM-UHFFFAOYSA-N dicyclohexylmethanamine Chemical compound C1CCCCC1C(N)C1CCCCC1 QVQGTNFYPJQJNM-UHFFFAOYSA-N 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- ATEAJVREBKABAP-UHFFFAOYSA-N [1-(diethylamino)-3-[7-(diethylcarbamoylamino)-4-methyl-2-oxochromen-3-yl]propan-2-yl] 3,4,5-trimethoxybenzoate Chemical compound CC=1C2=CC=C(NC(=O)N(CC)CC)C=C2OC(=O)C=1CC(CN(CC)CC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 ATEAJVREBKABAP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 229940086542 triethylamine Drugs 0.000 claims 19
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 claims 16
- NFFPFTGFVSWSTH-SNAWJCMRSA-N (e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC(\C=C\C(Cl)=O)=CC(OC)=C1OC NFFPFTGFVSWSTH-SNAWJCMRSA-N 0.000 claims 13
- ABDMMYZQNXWEBF-UHFFFAOYSA-N 2-[methyl-[3-[4-methyl-7-[[methyl-[2-(3,4,5-trimethoxybenzoyl)oxyethyl]carbamoyl]amino]-2-oxochromen-3-yl]-2-(3,4,5-trimethoxybenzoyl)oxypropyl]amino]ethyl 3,4,5-trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OCCN(C)CC(CC=2C(OC3=CC(NC(=O)N(C)CCOC(=O)C=4C=C(OC)C(OC)=C(OC)C=4)=CC=C3C=2C)=O)OC(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 ABDMMYZQNXWEBF-UHFFFAOYSA-N 0.000 claims 2
- WABBPWOBOHLPCS-UHFFFAOYSA-N [1-(cyclohexylmethylamino)-3-[7-[[cyclohexyl(methyl)carbamoyl]amino]-4-methyl-2-oxochromen-3-yl]propan-2-yl] 3,4,5-trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OC(CNCC2CCCCC2)CC=2C(OC3=CC(NC(=O)N(C)C4CCCCC4)=CC=C3C=2C)=O)=C1 WABBPWOBOHLPCS-UHFFFAOYSA-N 0.000 claims 2
- JZQJEVQZOAVSJC-UHFFFAOYSA-N [1-(dibutylamino)-3-[7-(dibutylcarbamoylamino)-4-methyl-2-oxochromen-3-yl]propan-2-yl] 3,4,5-trimethoxybenzoate Chemical compound CC=1C2=CC=C(NC(=O)N(CCCC)CCCC)C=C2OC(=O)C=1CC(CN(CCCC)CCCC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 JZQJEVQZOAVSJC-UHFFFAOYSA-N 0.000 claims 2
- SQRGGOCCRAGZPS-UHFFFAOYSA-N [1-(dibutylamino)-3-[7-(dibutylcarbamoylamino)-4-methyl-2-oxochromen-3-yl]propan-2-yl] 3-(3,4,5-trimethoxyphenyl)prop-2-enoate Chemical compound CC=1C2=CC=C(NC(=O)N(CCCC)CCCC)C=C2OC(=O)C=1CC(CN(CCCC)CCCC)OC(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1 SQRGGOCCRAGZPS-UHFFFAOYSA-N 0.000 claims 2
- RYULVBRPOYYABB-UHFFFAOYSA-N [1-[4-methyl-2-oxo-7-[(4-phenylpiperazine-1-carbonyl)amino]chromen-3-yl]-3-(4-phenylpiperazin-1-yl)propan-2-yl] 3,4,5-trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OC(CN2CCN(CC2)C=2C=CC=CC=2)CC=2C(OC3=CC(NC(=O)N4CCN(CC4)C=4C=CC=CC=4)=CC=C3C=2C)=O)=C1 RYULVBRPOYYABB-UHFFFAOYSA-N 0.000 claims 2
- NYVHFRHIMNJFEU-UHFFFAOYSA-N [1-[4-methyl-2-oxo-7-[(4-phenylpiperazine-1-carbonyl)amino]chromen-3-yl]-3-(4-phenylpiperazin-1-yl)propan-2-yl] 3-(3,4,5-trimethoxyphenyl)prop-2-enoate Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)OC(CN2CCN(CC2)C=2C=CC=CC=2)CC=2C(OC3=CC(NC(=O)N4CCN(CC4)C=4C=CC=CC=4)=CC=C3C=2C)=O)=C1 NYVHFRHIMNJFEU-UHFFFAOYSA-N 0.000 claims 2
- WMAVERQHGRPPQO-UHFFFAOYSA-N [1-[benzyl(methyl)amino]-3-[7-[[benzyl(methyl)carbamoyl]amino]-4-methyl-2-oxochromen-3-yl]propan-2-yl] 3,4,5-trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OC(CN(C)CC=2C=CC=CC=2)CC=2C(OC3=CC(NC(=O)N(C)CC=4C=CC=CC=4)=CC=C3C=2C)=O)=C1 WMAVERQHGRPPQO-UHFFFAOYSA-N 0.000 claims 2
- IGKJNLOMWNZADV-UHFFFAOYSA-N [1-[benzyl(methyl)amino]-3-[7-[[benzyl(methyl)carbamoyl]amino]-4-methyl-2-oxochromen-3-yl]propan-2-yl] 3-(3,4,5-trimethoxyphenyl)prop-2-enoate Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)OC(CN(C)CC=2C=CC=CC=2)CC=2C(OC3=CC(NC(=O)N(C)CC=4C=CC=CC=4)=CC=C3C=2C)=O)=C1 IGKJNLOMWNZADV-UHFFFAOYSA-N 0.000 claims 2
- RCIIMYSKQZMVIL-UHFFFAOYSA-N n-[3-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-4-methyl-2-oxochromen-7-yl]-4-phenylpiperazine-1-carboxamide Chemical compound O=C1OC=2C=C(NC(=O)N3CCN(CC3)C=3C=CC=CC=3)C=CC=2C(C)=C1CC(O)CN(CC1)CCN1C1=CC=CC=C1 RCIIMYSKQZMVIL-UHFFFAOYSA-N 0.000 claims 2
- CPZHTXUCUZZWLP-UHFFFAOYSA-N [1-(diethylamino)-3-[7-(diethylcarbamoylamino)-4-methyl-2-oxochromen-3-yl]propan-2-yl] 3-(3,4,5-trimethoxyphenyl)prop-2-enoate Chemical compound CC=1C2=CC=C(NC(=O)N(CC)CC)C=C2OC(=O)C=1CC(CN(CC)CC)OC(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1 CPZHTXUCUZZWLP-UHFFFAOYSA-N 0.000 claims 1
- AHAJUQQFULHFFC-UHFFFAOYSA-N [1-[4-methyl-7-[(4-methylpiperazine-1-carbonyl)amino]-2-oxochromen-3-yl]-3-(4-methylpiperazin-1-yl)propan-2-yl] 3,4,5-trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OC(CN2CCN(C)CC2)CC=2C(OC3=CC(NC(=O)N4CCN(C)CC4)=CC=C3C=2C)=O)=C1 AHAJUQQFULHFFC-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 11
- 125000004429 atom Chemical group 0.000 abstract description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000206672 Gelidium Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 239000002585 base Substances 0.000 description 2
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
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- 229930006000 Sucrose Natural products 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 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
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960005003 carbocromen Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 210000003748 coronary sinus Anatomy 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002798 polar solvent 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
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752530405 DE2530405A1 (de) | 1975-07-08 | 1975-07-08 | 2-benzopyranonderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE19752543945 DE2543945A1 (de) | 1975-10-02 | 1975-10-02 | 2-benzopyranonderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080237A true CA1080237A (en) | 1980-06-24 |
Family
ID=25769120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,404A Expired CA1080237A (en) | 1975-07-08 | 1976-07-06 | 2-benzopyranone derivatives, method for their manufacture and their use as medicaments |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4144336A (en, 2012) |
| JP (1) | JPS5225777A (en, 2012) |
| AT (1) | AT355014B (en, 2012) |
| AU (1) | AU506082B2 (en, 2012) |
| CA (1) | CA1080237A (en, 2012) |
| CH (1) | CH605889A5 (en, 2012) |
| DK (1) | DK306776A (en, 2012) |
| ES (1) | ES449629A1 (en, 2012) |
| FI (1) | FI761993A7 (en, 2012) |
| FR (1) | FR2316939A1 (en, 2012) |
| GB (1) | GB1547798A (en, 2012) |
| IE (1) | IE44012B1 (en, 2012) |
| IL (1) | IL49971A0 (en, 2012) |
| LU (1) | LU75313A1 (en, 2012) |
| NL (1) | NL7607494A (en, 2012) |
| NZ (1) | NZ181401A (en, 2012) |
| PT (1) | PT65338B (en, 2012) |
| SE (1) | SE7607856L (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU632796B2 (en) * | 1989-02-23 | 1993-01-14 | University Of North Carolina At Chapel Hill, The | Etoposide analogues |
| US5703130A (en) * | 1995-06-07 | 1997-12-30 | Institute Of Materia Medica, An Institute Of The Chinese Academy Of Medical Sciences | Chalcone retinoids and methods of use of same |
| US5716982A (en) * | 1995-06-07 | 1998-02-10 | Institute Of Materia Medica, An Institute Of The Chinese Academy Of Medical Sciences | Retinoids and methods of use of same |
| US5968940A (en) * | 1995-06-08 | 1999-10-19 | Institute Of Materia Medica | Retinoids and methods of use of same |
| WO2000034267A1 (fr) * | 1998-12-04 | 2000-06-15 | Takeda Chemical Industries, Ltd. | Procede de production d'un compose d'amide cyclique |
| CA2651732C (en) | 2006-05-18 | 2014-10-14 | Mannkind Corporation | Intracellular kinase inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1259349B (de) * | 1964-10-17 | 1968-01-25 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Derivaten des 7-Oxycumarins |
| US3652557A (en) * | 1968-01-19 | 1972-03-28 | Cassella Farbwerke Mainkur Ag | 3-(gamma-tertiary amino-beta-alkoxy benzoyloxy-propyl) - 4 -hydrocarbon - 5 8 - alkoxy coumarins |
| US3930003A (en) * | 1970-07-17 | 1975-12-30 | Troponwerke Dinklage & Co | Coumarine derivatives and process for the preparation thereof |
| IL37284A (en) * | 1970-07-17 | 1974-10-22 | Troponwerke Dinklage & Co | 3-aminoalkyl-7-ureido coumarine derivatives,their preparation and pharmaceutical compositions containing them |
-
1976
- 1976-07-05 IL IL49971A patent/IL49971A0/xx unknown
- 1976-07-05 FR FR7620488A patent/FR2316939A1/fr active Granted
- 1976-07-06 LU LU75313A patent/LU75313A1/xx unknown
- 1976-07-06 IE IE1491/76A patent/IE44012B1/en unknown
- 1976-07-06 CA CA256,404A patent/CA1080237A/en not_active Expired
- 1976-07-07 GB GB28223/76A patent/GB1547798A/en not_active Expired
- 1976-07-07 NZ NZ181401A patent/NZ181401A/xx unknown
- 1976-07-07 DK DK306776A patent/DK306776A/da not_active Application Discontinuation
- 1976-07-07 ES ES449629A patent/ES449629A1/es not_active Expired
- 1976-07-07 NL NL7607494A patent/NL7607494A/xx not_active Application Discontinuation
- 1976-07-07 AU AU15657/76A patent/AU506082B2/en not_active Expired
- 1976-07-07 CH CH870576A patent/CH605889A5/xx not_active IP Right Cessation
- 1976-07-07 AT AT498876A patent/AT355014B/de not_active IP Right Cessation
- 1976-07-07 JP JP51082446A patent/JPS5225777A/ja active Pending
- 1976-07-08 SE SE7607856A patent/SE7607856L/xx not_active Application Discontinuation
- 1976-07-08 US US05/703,340 patent/US4144336A/en not_active Expired - Lifetime
- 1976-07-08 PT PT65338A patent/PT65338B/pt unknown
- 1976-07-08 FI FI761993A patent/FI761993A7/fi not_active Application Discontinuation
-
1978
- 1978-11-24 US US05/963,652 patent/US4241207A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATA498876A (de) | 1979-07-15 |
| ES449629A1 (es) | 1977-07-01 |
| JPS5225777A (en) | 1977-02-25 |
| PT65338B (fr) | 1978-01-06 |
| AU1565776A (en) | 1978-01-12 |
| FI761993A7 (en, 2012) | 1977-01-09 |
| FR2316939B1 (en, 2012) | 1979-05-18 |
| PT65338A (fr) | 1976-08-01 |
| FR2316939A1 (fr) | 1977-02-04 |
| GB1547798A (en) | 1979-06-27 |
| IE44012L (en) | 1977-01-08 |
| LU75313A1 (en, 2012) | 1977-02-24 |
| US4144336A (en) | 1979-03-13 |
| DK306776A (da) | 1977-01-09 |
| NZ181401A (en) | 1978-03-06 |
| AU506082B2 (en) | 1979-12-13 |
| AT355014B (de) | 1980-02-11 |
| NL7607494A (nl) | 1977-01-11 |
| CH605889A5 (en, 2012) | 1978-10-13 |
| US4241207A (en) | 1980-12-23 |
| SE7607856L (sv) | 1977-01-09 |
| IE44012B1 (en) | 1981-07-29 |
| IL49971A0 (en) | 1976-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |