CY1343A - Therapeutic agents - Google Patents
Therapeutic agents Download PDFInfo
- Publication number
- CY1343A CY1343A CY1343A CY134380A CY1343A CY 1343 A CY1343 A CY 1343A CY 1343 A CY1343 A CY 1343A CY 134380 A CY134380 A CY 134380A CY 1343 A CY1343 A CY 1343A
- Authority
- CY
- Cyprus
- Prior art keywords
- quinolone
- methyl
- alkyl
- hydrogen
- halo
- Prior art date
Links
- 239000003814 drug Substances 0.000 title description 2
- 229940124597 therapeutic agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 150000007660 quinolones Chemical class 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- -1 loweralkoxy Chemical group 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001475 halogen functional group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 230000001225 therapeutic effect Effects 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 239000002775 capsule Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000003826 tablet Substances 0.000 claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000001506 calcium phosphate Substances 0.000 claims description 3
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 3
- 235000011010 calcium phosphates Nutrition 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 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 claims description 3
- UYGONJYYUKVHDD-UHFFFAOYSA-N flosequinan Chemical compound C1=C(F)C=C2N(C)C=C(S(C)=O)C(=O)C2=C1 UYGONJYYUKVHDD-UHFFFAOYSA-N 0.000 claims description 2
- 239000007903 gelatin capsule Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- UZWAHQKAIZUPJV-UHFFFAOYSA-N 1-methyl-3-methylsulfinylquinolin-4-one Chemical compound C1=CC=C2N(C)C=C(S(C)=O)C(=O)C2=C1 UZWAHQKAIZUPJV-UHFFFAOYSA-N 0.000 claims 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims 2
- JRUFLNGPZCQJMP-UHFFFAOYSA-N 7-chloro-6-methoxy-1-methyl-3-methylsulfinylquinolin-4-one 7-fluoro-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound ClC1=C(C=C2C(C(=CN(C2=C1)C)S(=O)C)=O)OC.FC1=CC=C2C(C(=CN(C2=C1)C)S(=O)C)=O JRUFLNGPZCQJMP-UHFFFAOYSA-N 0.000 claims 1
- 229920001800 Shellac Polymers 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 239000002662 enteric coated tablet Substances 0.000 claims 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 claims 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 claims 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims 1
- 229940113147 shellac Drugs 0.000 claims 1
- 239000004208 shellac Substances 0.000 claims 1
- 235000013874 shellac Nutrition 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 230000036772 blood pressure Effects 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 8
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007800 oxidant agent Substances 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
- 159000000000 sodium salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- BACOFPPVBVJWHF-UHFFFAOYSA-N 6,7-dimethoxy-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=C(OC)C(OC)=C2 BACOFPPVBVJWHF-UHFFFAOYSA-N 0.000 description 3
- GZQHWCULMKQPMV-UHFFFAOYSA-N 7-chloro-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound C1=C(Cl)C=C2N(C)C=C(S(C)=O)C(=O)C2=C1 GZQHWCULMKQPMV-UHFFFAOYSA-N 0.000 description 3
- KVGQFTUVCDHXBT-UHFFFAOYSA-N 7-fluoro-1,3-dimethylquinoline-4-thione Chemical compound FC1=CC=C2C(=S)C(C)=CN(C)C2=C1 KVGQFTUVCDHXBT-UHFFFAOYSA-N 0.000 description 3
- CKQUAMJNMYKHBP-UHFFFAOYSA-N 7-fluoro-6-methoxy-1,3-dimethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C2=C1C=C(F)C(OC)=C2 CKQUAMJNMYKHBP-UHFFFAOYSA-N 0.000 description 3
- ZCTAXXJVBDEDEK-UHFFFAOYSA-N 7-methoxy-1,3-dimethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C=2C1=CC(OC)=CC=2 ZCTAXXJVBDEDEK-UHFFFAOYSA-N 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 150000005130 benzoxazines Chemical class 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000004967 organic peroxy acids Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- AKNVDMJCVKFYSB-UHFFFAOYSA-N 1-methyl-3-methylsulfanyl-7-propan-2-ylquinolin-4-one Chemical compound CC(C)C1=CC=C2C(=O)C(SC)=CN(C)C2=C1 AKNVDMJCVKFYSB-UHFFFAOYSA-N 0.000 description 2
- FCLWUYJURISLKH-UHFFFAOYSA-N 1-methyl-3-methylsulfinyl-7-(trifluoromethyl)quinolin-4-one Chemical compound C1=C(C(F)(F)F)C=C2N(C)C=C(S(C)=O)C(=O)C2=C1 FCLWUYJURISLKH-UHFFFAOYSA-N 0.000 description 2
- BGDOLELXXPTPFX-UHFFFAOYSA-N 3,4-dihydro-2h-1,2-benzoxazine Chemical compound C1=CC=C2ONCCC2=C1 BGDOLELXXPTPFX-UHFFFAOYSA-N 0.000 description 2
- SCWPCJKOXRPFCD-UHFFFAOYSA-N 3-ethylsulfanyl-1-methylquinolin-4-one Chemical compound C1=CC=C2C(=O)C(SCC)=CN(C)C2=C1 SCWPCJKOXRPFCD-UHFFFAOYSA-N 0.000 description 2
- DBVVBYBNNNDCHK-UHFFFAOYSA-N 3-methylsulfinyl-3h-quinolin-4-one Chemical compound C1=CC=C2C(=O)C(S(=O)C)C=NC2=C1 DBVVBYBNNNDCHK-UHFFFAOYSA-N 0.000 description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical class C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- MPYIGVKNLKGBFV-UHFFFAOYSA-N 5-ethyl-1,3-dimethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C2=C1C=CC=C2CC MPYIGVKNLKGBFV-UHFFFAOYSA-N 0.000 description 2
- GEMDGXXVKPNXOV-UHFFFAOYSA-N 7-bromo-3-methylsulfinyl-3h-quinolin-4-one Chemical compound BrC1=CC=C2C(=O)C(S(=O)C)C=NC2=C1 GEMDGXXVKPNXOV-UHFFFAOYSA-N 0.000 description 2
- YTPAZJSGIQSNME-UHFFFAOYSA-N 7-chloro-6-methoxy-3-methyl-3h-quinoline-4-thione Chemical compound S=C1C(C)C=NC2=C1C=C(OC)C(Cl)=C2 YTPAZJSGIQSNME-UHFFFAOYSA-N 0.000 description 2
- ZGFPFJNYSUVWHB-UHFFFAOYSA-N 7-fluoro-3-methylsulfinyl-3h-quinolin-4-one Chemical compound FC1=CC=C2C(=O)C(S(=O)C)C=NC2=C1 ZGFPFJNYSUVWHB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- HZYCAKGEXXKCDM-UHFFFAOYSA-N Methyl 2-(methylthio)acetate Chemical compound COC(=O)CSC HZYCAKGEXXKCDM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 230000010349 pulsation Effects 0.000 description 2
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- SEYHGPJTLNZDRF-UHFFFAOYSA-N 1,3,5,6-tetramethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C2=C(C)C(C)=CC=C21 SEYHGPJTLNZDRF-UHFFFAOYSA-N 0.000 description 1
- GTCKDDFNAUGPSX-UHFFFAOYSA-N 1,3,5,7-tetramethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C=2C1=CC(C)=CC=2C GTCKDDFNAUGPSX-UHFFFAOYSA-N 0.000 description 1
- IPWWUQHCXIXFRA-UHFFFAOYSA-N 1,6,7-trimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=C(C)C(C)=C2 IPWWUQHCXIXFRA-UHFFFAOYSA-N 0.000 description 1
- XDRVLQHWGPQSCN-UHFFFAOYSA-N 1,6-dimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=CC(C)=CC=C21 XDRVLQHWGPQSCN-UHFFFAOYSA-N 0.000 description 1
- ZXNFYHLFPXEBGY-UHFFFAOYSA-N 1,7-dimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C=2C1=CC(C)=CC=2 ZXNFYHLFPXEBGY-UHFFFAOYSA-N 0.000 description 1
- FCSWOQDHAURNPI-UHFFFAOYSA-N 1,7-dimethyl-3-methylsulfinylquinoline-4-thione Chemical compound CN1C=C(S(C)=O)C(=S)C=2C1=CC(C)=CC=2 FCSWOQDHAURNPI-UHFFFAOYSA-N 0.000 description 1
- VHBJGBWEWWARRW-UHFFFAOYSA-N 1,8-dimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C(C)=CC=C2 VHBJGBWEWWARRW-UHFFFAOYSA-N 0.000 description 1
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- UAUPCSQPVYZSPA-UHFFFAOYSA-N 1-(1,3-dimethyl-4-sulfanylidenequinolin-6-yl)ethanone Chemical compound CN1C=C(C)C(=S)C2=CC(C(=O)C)=CC=C21 UAUPCSQPVYZSPA-UHFFFAOYSA-N 0.000 description 1
- YVJLDIJYCATDIW-UHFFFAOYSA-N 1-methyl-3,5-bis(methylsulfanyl)quinolin-4-one Chemical compound CN1C=C(SC)C(=O)C2=C1C=CC=C2SC YVJLDIJYCATDIW-UHFFFAOYSA-N 0.000 description 1
- XMOJSVXQECHJNT-UHFFFAOYSA-N 1-methyl-3,7-bis(methylsulfanyl)quinolin-4-one Chemical compound CN1C=C(SC)C(=O)C=2C1=CC(SC)=CC=2 XMOJSVXQECHJNT-UHFFFAOYSA-N 0.000 description 1
- WCBHMVXDXAVQMP-UHFFFAOYSA-N 1-methyl-3-methylsulfanyl-7-(trifluoromethyl)quinolin-4-one Chemical compound FC(F)(F)C1=CC=C2C(=O)C(SC)=CN(C)C2=C1 WCBHMVXDXAVQMP-UHFFFAOYSA-N 0.000 description 1
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- BNNICQAVXPXQAH-UHFFFAOYSA-N 2-amino-4-bromobenzoic acid Chemical compound NC1=CC(Br)=CC=C1C(O)=O BNNICQAVXPXQAH-UHFFFAOYSA-N 0.000 description 1
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- UKZUNQJPINIOFV-UHFFFAOYSA-N 5-chloro-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound C1=CC=C2N(C)C=C(S(C)=O)C(=O)C2=C1Cl UKZUNQJPINIOFV-UHFFFAOYSA-N 0.000 description 1
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- ZMWFZTQQRBMJLA-UHFFFAOYSA-N 6-chloro-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound ClC1=CC=C2N(C)C=C(S(C)=O)C(=O)C2=C1 ZMWFZTQQRBMJLA-UHFFFAOYSA-N 0.000 description 1
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- FAPZZOKJGZOQDH-UHFFFAOYSA-N 6-fluoro-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound FC1=CC=C2N(C)C=C(S(C)=O)C(=O)C2=C1 FAPZZOKJGZOQDH-UHFFFAOYSA-N 0.000 description 1
- JNQOTDDQSHNJJM-UHFFFAOYSA-N 6-methoxy-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=CC(OC)=CC=C21 JNQOTDDQSHNJJM-UHFFFAOYSA-N 0.000 description 1
- VVPJJZWBAGHGHV-UHFFFAOYSA-N 7-chloro-1,3,6-trimethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C2=C1C=C(Cl)C(C)=C2 VVPJJZWBAGHGHV-UHFFFAOYSA-N 0.000 description 1
- QZVANZRJAMFCCL-UHFFFAOYSA-N 7-chloro-1,3-dimethylquinoline-4-thione Chemical compound ClC1=CC=C2C(=S)C(C)=CN(C)C2=C1 QZVANZRJAMFCCL-UHFFFAOYSA-N 0.000 description 1
- HMDMVQYMDYAQFW-UHFFFAOYSA-N 7-chloro-1,6-dimethyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=C(Cl)C(C)=C2 HMDMVQYMDYAQFW-UHFFFAOYSA-N 0.000 description 1
- BVQHESBUNAJKHI-UHFFFAOYSA-N 7-chloro-3-ethylsulfanyl-1-methylquinolin-4-one Chemical compound ClC1=CC=C2C(=O)C(SCC)=CN(C)C2=C1 BVQHESBUNAJKHI-UHFFFAOYSA-N 0.000 description 1
- OYNHAKCQKUXFGQ-UHFFFAOYSA-N 7-chloro-3-methylsulfinyl-3h-quinolin-4-one Chemical compound ClC1=CC=C2C(=O)C(S(=O)C)C=NC2=C1 OYNHAKCQKUXFGQ-UHFFFAOYSA-N 0.000 description 1
- AANRGFUCQKJETA-UHFFFAOYSA-N 7-ethyl-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C=2C1=CC(CC)=CC=2 AANRGFUCQKJETA-UHFFFAOYSA-N 0.000 description 1
- KVNUHORYQUTQFN-UHFFFAOYSA-N 7-fluoro-6-methoxy-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=C(F)C(OC)=C2 KVNUHORYQUTQFN-UHFFFAOYSA-N 0.000 description 1
- FVUKRQMXBGREGQ-UHFFFAOYSA-N 7-hydroxy-1,3-dimethylquinoline-4-thione Chemical compound OC1=CC=C2C(C(=CN(C2=C1)C)C)=S FVUKRQMXBGREGQ-UHFFFAOYSA-N 0.000 description 1
- LIDIPFARVOJRLY-UHFFFAOYSA-N 8-chloro-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound C1=CC(Cl)=C2N(C)C=C(S(C)=O)C(=O)C2=C1 LIDIPFARVOJRLY-UHFFFAOYSA-N 0.000 description 1
- PIYUHUAVPNAOGA-UHFFFAOYSA-N 8-methoxy-1,3-dimethylquinoline-4-thione Chemical compound CN1C=C(C)C(=S)C2=C1C(OC)=CC=C2 PIYUHUAVPNAOGA-UHFFFAOYSA-N 0.000 description 1
- GTXJURMEPHQKNS-UHFFFAOYSA-N 8-methoxy-1-methyl-3-methylsulfinylquinolin-4-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C(OC)=CC=C2 GTXJURMEPHQKNS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RLYBUTNJEIGEPK-UHFFFAOYSA-N O-methyl 3-hydroxy-2-methylprop-2-enethioate Chemical compound OC=C(C(=S)OC)C RLYBUTNJEIGEPK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 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
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 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
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- KKUPCEYZHXBGTF-UHFFFAOYSA-N o-methyl 2-methyl-3-(3-methylsulfanylanilino)prop-2-enethioate Chemical compound COC(=S)C(C)=CNC1=CC=CC(SC)=C1 KKUPCEYZHXBGTF-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 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
- 229920001223 polyethylene glycol Polymers 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
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7910558 | 1979-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1343A true CY1343A (en) | 1987-01-16 |
Family
ID=10504143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1343A CY1343A (en) | 1979-03-27 | 1980-03-25 | Therapeutic agents |
Country Status (10)
| Country | Link |
|---|---|
| JP (2) | JPS55130960A (enrdf_load_stackoverflow) |
| BE (1) | BE882443A (enrdf_load_stackoverflow) |
| CY (1) | CY1343A (enrdf_load_stackoverflow) |
| ES (1) | ES8104232A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2047691B (enrdf_load_stackoverflow) |
| GE (1) | GEP19970835B (enrdf_load_stackoverflow) |
| JO (1) | JO1072B1 (enrdf_load_stackoverflow) |
| MX (1) | MX5950A (enrdf_load_stackoverflow) |
| SU (1) | SU1124886A3 (enrdf_load_stackoverflow) |
| ZA (1) | ZA801575B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA801575B (en) * | 1979-03-27 | 1981-03-25 | Boots Co Ltd | Therapeutic agents |
| IE51542B1 (en) * | 1980-09-26 | 1987-01-07 | Boots Co Ltd | Therapeutic agents |
| US5081121A (en) * | 1988-05-24 | 1992-01-14 | Tatsushi Osawa | 4(1h)-quinolone derivatives |
| US8697674B2 (en) | 2004-12-29 | 2014-04-15 | Naturon, Inc. | Xanthurenic acid derivative pharmaceutical compositions and methods related thereto |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA801575B (en) * | 1979-03-27 | 1981-03-25 | Boots Co Ltd | Therapeutic agents |
-
1980
- 1980-03-18 ZA ZA00801575A patent/ZA801575B/xx unknown
- 1980-03-25 GB GB8010075A patent/GB2047691B/en not_active Expired
- 1980-03-25 CY CY1343A patent/CY1343A/en unknown
- 1980-03-26 JO JO19801072A patent/JO1072B1/en active
- 1980-03-26 ES ES489929A patent/ES8104232A1/es not_active Expired
- 1980-03-26 BE BE0/199956A patent/BE882443A/fr not_active IP Right Cessation
- 1980-03-27 JP JP3961080A patent/JPS55130960A/ja active Granted
-
1981
- 1981-01-19 SU SU802897803A patent/SU1124886A3/ru active
-
1985
- 1985-01-09 MX MX595085A patent/MX5950A/es unknown
-
1986
- 1986-12-24 JP JP61316048A patent/JPS62215526A/ja active Granted
-
1994
- 1994-09-07 GE GEAP19942162A patent/GEP19970835B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA801575B (en) | 1981-03-25 |
| SU1124886A3 (ru) | 1984-11-15 |
| BE882443A (fr) | 1980-09-26 |
| ES489929A0 (es) | 1981-04-16 |
| MX5950A (es) | 1993-11-01 |
| JPS55130960A (en) | 1980-10-11 |
| JO1072B1 (en) | 1982-07-10 |
| JPS62215526A (ja) | 1987-09-22 |
| GB2047691A (en) | 1980-12-03 |
| GEP19970835B (en) | 1997-02-10 |
| ES8104232A1 (es) | 1981-04-16 |
| JPH0114224B2 (enrdf_load_stackoverflow) | 1989-03-10 |
| GB2047691B (en) | 1983-07-20 |
| JPH0250086B2 (enrdf_load_stackoverflow) | 1990-11-01 |
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