IL31508A - Antipyretic preparations containing a history of esters of the 4-hydroxy-3-quinoline carboxylic acid esters - Google Patents
Antipyretic preparations containing a history of esters of the 4-hydroxy-3-quinoline carboxylic acid estersInfo
- Publication number
- IL31508A IL31508A IL31508A IL3150869A IL31508A IL 31508 A IL31508 A IL 31508A IL 31508 A IL31508 A IL 31508A IL 3150869 A IL3150869 A IL 3150869A IL 31508 A IL31508 A IL 31508A
- Authority
- IL
- Israel
- Prior art keywords
- quinoline
- hydroxy
- carboxylate
- methyl
- ethyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 35
- 239000003430 antimalarial agent Substances 0.000 title claims description 16
- 230000000078 anti-malarial effect Effects 0.000 title claims description 14
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 title 1
- -1 quinoline compound Chemical class 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 28
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000002552 dosage form Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- OBCCLVREHLEMJK-UHFFFAOYSA-N methyl 6-decoxy-7-(diethylamino)-4-oxo-1H-quinoline-3-carboxylate Chemical group OC1=C(C=NC2=CC(=C(C=C12)OCCCCCCCCCC)N(CC)CC)C(=O)OC OBCCLVREHLEMJK-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 201000004792 malaria Diseases 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000002775 capsule Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000004083 survival effect Effects 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- NMYCTBARPUAEQN-UHFFFAOYSA-N methyl 7-(diethylamino)-4-oxo-6-propyl-1h-quinoline-3-carboxylate Chemical compound N1C=C(C(=O)OC)C(=O)C2=C1C=C(N(CC)CC)C(CCC)=C2 NMYCTBARPUAEQN-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 230000001154 acute effect Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229960003677 chloroquine Drugs 0.000 description 3
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229960000443 hydrochloric acid Drugs 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- VZGBYOVWARGTNX-UHFFFAOYSA-N N-[4-(2-propan-2-yloxypropyl)phenyl]acetamide Chemical compound C(C)(C)OC(CC1=CC=C(C=C1)NC(C)=O)C VZGBYOVWARGTNX-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000224017 Plasmodium berghei Species 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229940033495 antimalarials Drugs 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- RHFZTBSULNJWEI-UHFFFAOYSA-N dimethyl 2-(methoxymethylidene)propanedioate Chemical compound COC=C(C(=O)OC)C(=O)OC RHFZTBSULNJWEI-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- IZUIRUXCEZRABH-UHFFFAOYSA-N ethyl 6-decyl-7-(diethylamino)-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)CCCCCCCCCC)N(CC)CC)C(=O)OCC IZUIRUXCEZRABH-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSNZUXZJCZHSQP-UHFFFAOYSA-N methyl 4-oxo-7-propan-2-yloxy-6-propyl-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)CCC)OC(C)C)C(=O)OC QSNZUXZJCZHSQP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229940058924 other antimalarials in atc Drugs 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000009117 preventive therapy Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 description 2
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- CASBYSXOFBAEDS-UHFFFAOYSA-N 1-decoxy-2-nitrobenzene Chemical compound CCCCCCCCCCOC1=CC=CC=C1[N+]([O-])=O CASBYSXOFBAEDS-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- PVFWLRKOYPBTIB-UHFFFAOYSA-N 2-decoxy-N,N-diethyl-5-nitroaniline Chemical compound C(CCCCCCCCC)OC1=C(N(CC)CC)C=C(C=C1)[N+](=O)[O-] PVFWLRKOYPBTIB-UHFFFAOYSA-N 0.000 description 1
- FJFVPTKENBLYAC-UHFFFAOYSA-N 2-decoxy-N,N-diethylaniline Chemical compound C(CCCCCCCCC)OC1=C(N(CC)CC)C=CC=C1 FJFVPTKENBLYAC-UHFFFAOYSA-N 0.000 description 1
- XVGMSYLAZANFQC-UHFFFAOYSA-N 2-propan-2-ylperoxycarbonylprop-2-enoic acid Chemical compound CC(C)OOC(=O)C(=C)C(O)=O XVGMSYLAZANFQC-UHFFFAOYSA-N 0.000 description 1
- JAKHLQNEMUMGKP-UHFFFAOYSA-N 3,4-diethylaniline Chemical compound CCC1=CC=C(N)C=C1CC JAKHLQNEMUMGKP-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- LNGRMOCSFIJSQK-UHFFFAOYSA-N 5-ethyl-1h-triazin-6-one Chemical compound CCC1=CN=NNC1=O LNGRMOCSFIJSQK-UHFFFAOYSA-N 0.000 description 1
- RTPBXZHUTANRMC-UHFFFAOYSA-N 5-methyl-1H-triazin-6-one Chemical compound CC=1C(NN=NC=1)=O RTPBXZHUTANRMC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 102000011767 Acute-Phase Proteins Human genes 0.000 description 1
- 108010062271 Acute-Phase Proteins Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 208000002476 Falciparum Malaria Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 206010035500 Plasmodium falciparum infection Diseases 0.000 description 1
- 201000011336 Plasmodium falciparum malaria Diseases 0.000 description 1
- 241000223821 Plasmodium malariae Species 0.000 description 1
- 206010035501 Plasmodium malariae infection Diseases 0.000 description 1
- 241000223810 Plasmodium vivax Species 0.000 description 1
- 206010035503 Plasmodium vivax infection Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- 239000004480 active ingredient Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- COVCEMRPQCJXLA-UHFFFAOYSA-N ethyl 6-(diethylamino)-7-ethyl-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)N(CC)CC)CC)C(=O)OCC COVCEMRPQCJXLA-UHFFFAOYSA-N 0.000 description 1
- RROFQPIEGXJVTP-UHFFFAOYSA-N ethyl 6-butyl-4-oxo-7-propoxy-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)CCCC)OCCC)C(=O)OCC RROFQPIEGXJVTP-UHFFFAOYSA-N 0.000 description 1
- CHAPUUUBWFGJOR-UHFFFAOYSA-N ethyl 6-ethoxy-4-oxo-7-phenylmethoxy-1H-quinoline-3-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C2C(=C(C=NC2=C1)C(=O)OCC)O)OCC CHAPUUUBWFGJOR-UHFFFAOYSA-N 0.000 description 1
- NSWKAERPQLBPMR-UHFFFAOYSA-N ethyl 6-ethoxy-7-(2-methylpropyl)-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)OCC)CC(C)C)C(=O)OCC NSWKAERPQLBPMR-UHFFFAOYSA-N 0.000 description 1
- FNIOTKFYQMVWOJ-UHFFFAOYSA-N ethyl 7-(diethylamino)-4-oxo-6-propyl-1h-quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C=C(N(CC)CC)C(CCC)=CC2=C1O FNIOTKFYQMVWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000021760 high fever Diseases 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 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
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- FEKJJOYOOCLBIV-UHFFFAOYSA-N methyl 6,7-bis(2-methylpropoxy)-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C(C)C)OC=1C=C2C(=C(C=NC2=CC1OCC(C)C)C(=O)OC)O FEKJJOYOOCLBIV-UHFFFAOYSA-N 0.000 description 1
- MYSIWIXYHSAAJA-UHFFFAOYSA-N methyl 6-(dimethylamino)-4-oxo-7-propyl-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)N(C)C)CCC)C(=O)OC MYSIWIXYHSAAJA-UHFFFAOYSA-N 0.000 description 1
- GSWZYTGKDDKYAE-UHFFFAOYSA-N methyl 6-decyl-7-ethyl-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)CCCCCCCCCC)CC)C(=O)OC GSWZYTGKDDKYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WEIMMECSAQVSGO-UHFFFAOYSA-N n-(3-hydroxy-4-propylphenyl)acetamide Chemical compound CCCC1=CC=C(NC(C)=O)C=C1O WEIMMECSAQVSGO-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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229960005179 primaquine Drugs 0.000 description 1
- INDBQLZJXZLFIT-UHFFFAOYSA-N primaquine Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 INDBQLZJXZLFIT-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 229960005385 proguanil Drugs 0.000 description 1
- QSQMCHCNQBHNDB-UHFFFAOYSA-N propyl 7-(dipropylamino)-6-ethyl-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)CC)N(CCC)CCC)C(=O)OCCC QSQMCHCNQBHNDB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70666868A | 1968-02-19 | 1968-02-19 | |
| US78245368A | 1968-12-09 | 1968-12-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31508A0 IL31508A0 (en) | 1969-04-30 |
| IL31508A true IL31508A (en) | 1972-02-29 |
Family
ID=27107727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31508A IL31508A (en) | 1968-02-19 | 1969-01-28 | Antipyretic preparations containing a history of esters of the 4-hydroxy-3-quinoline carboxylic acid esters |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1908262A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2002194A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1219721A (enrdf_load_stackoverflow) |
| IL (1) | IL31508A (enrdf_load_stackoverflow) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1007590A (en) * | 1962-04-09 | 1965-10-13 | Norwich Pharma Co | Lower alkyl esters of 6,7-di(lower)alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| US3478084A (en) * | 1965-12-22 | 1969-11-11 | Merck & Co Inc | Lower alkyl alpha-carboalkoxy-beta-(3,4-disubstituted anilino) acrylates |
| GB1168801A (en) * | 1966-05-13 | 1969-10-29 | May & Baker Ltd | Quinoline Derivatives |
-
1969
- 1969-01-28 IL IL31508A patent/IL31508A/en unknown
- 1969-02-17 GB GB8529/69A patent/GB1219721A/en not_active Expired
- 1969-02-19 FR FR6904138A patent/FR2002194A1/fr not_active Withdrawn
- 1969-02-19 DE DE19691908262 patent/DE1908262A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1908262A1 (de) | 1969-09-11 |
| IL31508A0 (en) | 1969-04-30 |
| FR2002194A1 (enrdf_load_stackoverflow) | 1969-10-17 |
| GB1219721A (en) | 1971-01-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4322420A (en) | Method of using 4-anilinoquinazoline derivatives as analgesic and anti-inflammatory agents | |
| US4006237A (en) | Tetrahydrocarbostyril derivatives for the prophylaxis of asthma, hayfever and rhinitis | |
| US4806549A (en) | 4-amino-3-carbonyl substituted quinolines | |
| WO2002026713A1 (en) | Antiparasitic compounds | |
| US5596002A (en) | Method of treating chloroquine-resistant malaria with aminoquinoline derivatives | |
| US3910922A (en) | Novel trifluoromethyl-quinolines | |
| CN100522959C (zh) | 一类6-芳基-3-环氨基甲基吡喃酮类衍生物的制备及用途 | |
| AU644082B2 (en) | Indenoindole compounds | |
| EP0336544A1 (en) | Heteroaryl 4-amino-3-acylquinoline derivatives and their use as inhibitors of gastric secretion | |
| EP0181521A1 (en) | Antimicrobial 1-substituted Phenyl-4-oxoquinoline-3-carboxylic acid compounds | |
| US3549761A (en) | Method of treating malaria with a loweralkyl 4-hydroxy - 6,7 - disubstituted quinoline-3-carboxylates | |
| US4970214A (en) | Quinoline substituted oxomethyl or thioxomethyl glycine derivatives and aldose reductase inhibition therewith | |
| CA1334669C (en) | N-substituted alkylidene-1,2,3,4-tetrahydro-9- acridinamines, a process for their preparation and their use as medicaments | |
| IL31508A (en) | Antipyretic preparations containing a history of esters of the 4-hydroxy-3-quinoline carboxylic acid esters | |
| US5668143A (en) | Heterocyclic benzenesulfonylimine derivatives as inhibitors of IL-1 action | |
| US4065457A (en) | 4-Hydroxy-3-nitro-carbostyril compounds | |
| US3549642A (en) | 6,7-disubstituted-4-hydroxy-quinoline-3-carboxylates | |
| EP0308059B1 (en) | 1,2,3,4-tetrahydroisoquinoline antiarrhythmic agents | |
| EP0024638A1 (en) | Substituted quinolinone-alkanecarboxylic acids, their preparation, and medicaments containing them | |
| GB1572920A (en) | Quinoline carboxalic acid esters | |
| CS195731B2 (en) | Process for preparing n-/5-tetrazolyl/-1-oxo-1h-6-alkoxypyrimido/1,2-a/quinolin-2-carboxamides | |
| SU1189349A3 (ru) | Способ получени 6-замещенных гексагидроиндазолизохинолинов или их солей | |
| US4298610A (en) | Ester derivatives of quinolopyran-4-one-2-carboxylic acids and antiallergic antasthmatics | |
| US3542781A (en) | 7-alkylamino 7-hydroxy quinoline 3-carboxylates | |
| US4168318A (en) | 1-(2,4,6-Trihydroxyphenyl)-propanedione-(1,2)-compounds and therapeutic compositions |