JPH02256614A - 薬剤耐性原生動物感染の処置に於けるラクタムイミド類 - Google Patents
薬剤耐性原生動物感染の処置に於けるラクタムイミド類Info
- Publication number
- JPH02256614A JPH02256614A JP1291439A JP29143989A JPH02256614A JP H02256614 A JPH02256614 A JP H02256614A JP 1291439 A JP1291439 A JP 1291439A JP 29143989 A JP29143989 A JP 29143989A JP H02256614 A JPH02256614 A JP H02256614A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- formula
- group
- drug
- phenyl
- 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.)
- Pending
Links
- -1 Lactam imide Chemical class 0.000 title claims abstract description 77
- 239000003814 drug Substances 0.000 title claims abstract description 60
- 229940079593 drug Drugs 0.000 title claims abstract description 50
- 208000015181 infectious disease Diseases 0.000 title claims abstract description 18
- 238000011282 treatment Methods 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 201000004792 malaria Diseases 0.000 claims abstract description 17
- 239000003904 antiprotozoal agent Substances 0.000 claims abstract description 15
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 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 claims description 16
- 229960003677 chloroquine Drugs 0.000 claims description 16
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 208000010362 Protozoan Infections Diseases 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Natural products C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229960001962 mefloquine Drugs 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 230000000884 anti-protozoa Effects 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 5
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 5
- 229960005179 primaquine Drugs 0.000 claims description 5
- 229960000948 quinine Drugs 0.000 claims description 5
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 229960001444 amodiaquine Drugs 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- CKXZJIAJKYYQLR-UHFFFAOYSA-N n-(2-phenylphenyl)-1-azacyclotridecen-2-amine Chemical compound C1CCCCCCCCCCNC1=NC1=CC=CC=C1C1=CC=CC=C1 CKXZJIAJKYYQLR-UHFFFAOYSA-N 0.000 claims description 2
- WWPISVNKRIXADH-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-1-azacyclotridecen-2-amine Chemical compound C1CC2CC1CC2N=C1CCCCCCCCCCCN1 WWPISVNKRIXADH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 12
- 150000001721 carbon Chemical group 0.000 claims 2
- INDBQLZJXZLFIT-UHFFFAOYSA-N primaquine Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 INDBQLZJXZLFIT-UHFFFAOYSA-N 0.000 claims 2
- 125000003410 quininyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RTRIXVOSRYRSBP-FGZHOGPDSA-N n-[(1r,2r)-2-phenylcyclopentyl]-1-azacyclotridecen-2-amine Chemical compound N([C@@H]1CCC[C@@H]1C=1C=CC=CC=1)C1=NCCCCCCCCCCC1 RTRIXVOSRYRSBP-FGZHOGPDSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- UFADJPZTTUWZMP-UHFFFAOYSA-N azacyclotridecane Chemical compound C1CCCCCCNCCCCC1 UFADJPZTTUWZMP-UHFFFAOYSA-N 0.000 abstract description 16
- 241000223960 Plasmodium falciparum Species 0.000 abstract description 7
- 241000224016 Plasmodium Species 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 54
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 30
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- KFAUAWMNLGGWLP-UHFFFAOYSA-N azacyclododecane Chemical compound C1CCCCCNCCCCC1 KFAUAWMNLGGWLP-UHFFFAOYSA-N 0.000 description 9
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- UOIGOLSKSFDTHJ-UHFFFAOYSA-N azacycloundecane Chemical compound C1CCCCCNCCCC1 UOIGOLSKSFDTHJ-UHFFFAOYSA-N 0.000 description 8
- VJEIIJANCJRLFJ-UHFFFAOYSA-N azecane Chemical compound C1CCCCNCCCC1 VJEIIJANCJRLFJ-UHFFFAOYSA-N 0.000 description 7
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 241000282412 Homo Species 0.000 description 4
- 206010037075 Protozoal infections Diseases 0.000 description 4
- 239000003430 antimalarial agent Substances 0.000 description 4
- NRHDCQLCSOWVTF-UHFFFAOYSA-N azonane Chemical compound C1CCCCNCCC1 NRHDCQLCSOWVTF-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- GJOHLWZHWQUKAU-UHFFFAOYSA-N 5-azaniumylpentan-2-yl-(6-methoxyquinolin-8-yl)azanium;dihydrogen phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 GJOHLWZHWQUKAU-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000002648 combination therapy Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 244000045947 parasite Species 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- HWGJWYNMDPTGTD-UHFFFAOYSA-N 1h-azonine Chemical compound C=1C=CC=CNC=CC=1 HWGJWYNMDPTGTD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- FDGQSTZJBFJUBT-UHFFFAOYSA-N Hypoxanthine Natural products O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000004554 Leishmaniasis Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229940033495 antimalarials Drugs 0.000 description 2
- 201000008680 babesiosis Diseases 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 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
- 239000002547 new drug Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000008180 pharmaceutical surfactant Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003419 tautomerization reaction Methods 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- JXQDOVYIHGRIDA-UHFFFAOYSA-N 1-ethyl-n-[furan-2-yl(phenyl)methyl]azocan-2-imine Chemical compound CCN1CCCCCCC1=NC(C=1C=CC=CC=1)C1=CC=CO1 JXQDOVYIHGRIDA-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 206010003399 Arthropod bite Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical class CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000002476 Falciparum Malaria Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 241000222722 Leishmania <genus> Species 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- 241000091577 Mexicana Species 0.000 description 1
- 241000238367 Mya arenaria Species 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- ARFHIAQFJWUCFH-IZZDOVSWSA-N Nifurtimox Chemical compound CC1CS(=O)(=O)CCN1\N=C\C1=CC=C([N+]([O-])=O)O1 ARFHIAQFJWUCFH-IZZDOVSWSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 201000011336 Plasmodium falciparum malaria Diseases 0.000 description 1
- 241000223821 Plasmodium malariae Species 0.000 description 1
- 241000223810 Plasmodium vivax Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 241001161107 Sphyraena ensis Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000223777 Theileria Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000223104 Trypanosoma Species 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 229960003942 amphotericin b Drugs 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- ZDINGUUTWDGGFF-UHFFFAOYSA-N antimony(5+) Chemical class [Sb+5] ZDINGUUTWDGGFF-UHFFFAOYSA-N 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- XXRGLCKZBCIEKO-DLMDZQPMSA-N azocine Chemical compound C/1=C/C=C\N=C/C=C\1 XXRGLCKZBCIEKO-DLMDZQPMSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 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
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- GRFNBEZIAWKNCO-UHFFFAOYSA-N mhp Natural products OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- PFDYZJOXNMTZKA-UHFFFAOYSA-N n-(1,2-diphenylethyl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound C=1C=CC=CC=1CC(C=1C=CC=CC=1)N=C1CCCN1 PFDYZJOXNMTZKA-UHFFFAOYSA-N 0.000 description 1
- NTAHICZLRCAATO-UHFFFAOYSA-N n-(1,4-diphenylbutyl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound C=1C=CC=CC=1CCCC(C=1C=CC=CC=1)N=C1CCCN1 NTAHICZLRCAATO-UHFFFAOYSA-N 0.000 description 1
- ZGGSCVUIKNQWHQ-UHFFFAOYSA-N n-(1-benzylcyclopentyl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound C1CCCC1(N=C1NCCC1)CC1=CC=CC=C1 ZGGSCVUIKNQWHQ-UHFFFAOYSA-N 0.000 description 1
- SLMOXBSVNQOMBW-UHFFFAOYSA-N n-(1-dibenzothiophen-2-ylethyl)-1-methylazepan-2-imine Chemical compound C=1C=C2SC3=CC=CC=C3C2=CC=1C(C)N=C1CCCCCN1C SLMOXBSVNQOMBW-UHFFFAOYSA-N 0.000 description 1
- BQUWUEACEVJNPO-UHFFFAOYSA-N n-(1-dibenzothiophen-2-ylethyl)-2,3,4,5,6,7-hexahydroazocin-8-amine Chemical compound C=1C=C2SC3=CC=CC=C3C2=CC=1C(C)N=C1CCCCCCN1 BQUWUEACEVJNPO-UHFFFAOYSA-N 0.000 description 1
- ZDKJWWFRNAZTTA-UHFFFAOYSA-N n-(1-phenanthren-2-ylethyl)-1-azacyclotridecen-2-amine Chemical compound C=1C=C(C2=CC=CC=C2C=C2)C2=CC=1C(C)N=C1CCCCCCCCCCCN1 ZDKJWWFRNAZTTA-UHFFFAOYSA-N 0.000 description 1
- MYCRCXJRZZARMI-UHFFFAOYSA-N n-(1-phenanthren-9-ylethyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C2=CC=CC=C2C2=CC=CC=C2C=1C(C)N=C1CCCCCN1 MYCRCXJRZZARMI-UHFFFAOYSA-N 0.000 description 1
- WRIGUHOSJVYOPY-UHFFFAOYSA-N n-(1-thiophen-2-ylpropyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CSC=1C(CC)N=C1CCCCCN1 WRIGUHOSJVYOPY-UHFFFAOYSA-N 0.000 description 1
- NTGRPTSGPHBFDM-UHFFFAOYSA-N n-(1-thiophen-2-ylpropyl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound C=1C=CSC=1C(CC)N=C1CCCN1 NTGRPTSGPHBFDM-UHFFFAOYSA-N 0.000 description 1
- PLWBCYHHWCBSGE-UHFFFAOYSA-N n-(10-butoxydecyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound CCCCOCCCCCCCCCCNC1=NCCCCC1 PLWBCYHHWCBSGE-UHFFFAOYSA-N 0.000 description 1
- UFRZJTAQPOHHTG-UHFFFAOYSA-N n-(12-propoxydodecyl)-1-azacyclododecen-2-amine Chemical compound CCCOCCCCCCCCCCCCN=C1CCCCCCCCCCN1 UFRZJTAQPOHHTG-UHFFFAOYSA-N 0.000 description 1
- JMQWHLQZHOHHHS-UHFFFAOYSA-N n-(12-propoxydodecyl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound CCCOCCCCCCCCCCCCN=C1CCCN1 JMQWHLQZHOHHHS-UHFFFAOYSA-N 0.000 description 1
- XNIRTEFWTMCYDP-UHFFFAOYSA-N n-(2,2-diphenylpentyl)-3,4,5,6,7,8-hexahydro-2h-azonin-9-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(CCC)CN=C1CCCCCCCN1 XNIRTEFWTMCYDP-UHFFFAOYSA-N 0.000 description 1
- SOWCGYNGICQOOA-UHFFFAOYSA-N n-(2,3-diphenylpropyl)-1-azacyclotridecen-2-amine Chemical compound C=1C=CC=CC=1CC(C=1C=CC=CC=1)CN=C1CCCCCCCCCCCN1 SOWCGYNGICQOOA-UHFFFAOYSA-N 0.000 description 1
- AHWTWBXQLMCECI-UHFFFAOYSA-N n-(2-adamantyl)-1-methyl-azacyclododecan-2-imine Chemical compound CN1CCCCCCCCCCC1=NC1C(C2)CC3CC2CC1C3 AHWTWBXQLMCECI-UHFFFAOYSA-N 0.000 description 1
- RMJCUXQTEZHWIZ-UHFFFAOYSA-N n-(2-dibenzofuran-2-ylethyl)-3,4,5,6,7,8-hexahydro-2h-azonin-9-amine Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1CCN=C1CCCCCCCN1 RMJCUXQTEZHWIZ-UHFFFAOYSA-N 0.000 description 1
- QICQZXFSWQALCN-UHFFFAOYSA-N n-(2-methyl-1-phenanthren-3-ylpropyl)-2,3,4,5,6,7-hexahydroazocin-8-amine Chemical compound C=1C=C2C=CC3=CC=CC=C3C2=CC=1C(C(C)C)N=C1CCCCCCN1 QICQZXFSWQALCN-UHFFFAOYSA-N 0.000 description 1
- JHVUEJJJEAVINT-UHFFFAOYSA-N n-(2-phenylcyclopropyl)-1-azacyclotridecen-2-amine Chemical compound C=1C=CC=CC=1C1CC1N=C1CCCCCCCCCCCN1 JHVUEJJJEAVINT-UHFFFAOYSA-N 0.000 description 1
- OOQUJNIKLUMVGH-UHFFFAOYSA-N n-(2-phenylphenyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C1CCCCN=C1NC1=CC=CC=C1C1=CC=CC=C1 OOQUJNIKLUMVGH-UHFFFAOYSA-N 0.000 description 1
- OZWQWKDLSXMIRT-UHFFFAOYSA-N n-(3,3-diphenylpropyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C1CCCCNC1=NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 OZWQWKDLSXMIRT-UHFFFAOYSA-N 0.000 description 1
- LXDFMJPDFURZNE-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CC2CC1CC2N=C1CCCCN1 LXDFMJPDFURZNE-UHFFFAOYSA-N 0.000 description 1
- VCHKXPLQHOIZNK-UHFFFAOYSA-N n-(3-methyl-2,2-diphenylbutyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(C)C)CN=C1CCCCCN1 VCHKXPLQHOIZNK-UHFFFAOYSA-N 0.000 description 1
- VANUQYNVIMHFPW-UHFFFAOYSA-N n-(4-bicyclo[2.2.1]heptanyl)-1-azacyclotridecen-2-amine Chemical compound C1CC(C2)CCC21N=C1CCCCCCCCCCCN1 VANUQYNVIMHFPW-UHFFFAOYSA-N 0.000 description 1
- BYGSWKRQBGTHDV-UHFFFAOYSA-N n-(8-methoxyoctyl)-1-azacyclotridecen-2-amine Chemical compound COCCCCCCCCN=C1CCCCCCCCCCCN1 BYGSWKRQBGTHDV-UHFFFAOYSA-N 0.000 description 1
- HWTZJAVRUWLXQX-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=COC=1CNC1=NCCCCC1 HWTZJAVRUWLXQX-UHFFFAOYSA-N 0.000 description 1
- GCDHFEDAPWTWRG-UHFFFAOYSA-N n-[(3-methoxyphenyl)-phenylmethyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound COC1=CC=CC(C(N=C2NCCCCC2)C=2C=CC=CC=2)=C1 GCDHFEDAPWTWRG-UHFFFAOYSA-N 0.000 description 1
- ZOLIZNDWBAVXHU-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1=CC(Cl)=CC=C1CN=C1NCCCC1 ZOLIZNDWBAVXHU-UHFFFAOYSA-N 0.000 description 1
- SXRRVVHLNCCYMN-UHFFFAOYSA-N n-[1-(2,3-dihydro-1h-inden-4-yl)ethyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CC=2CCCC=2C=1C(C)N=C1CCCCCN1 SXRRVVHLNCCYMN-UHFFFAOYSA-N 0.000 description 1
- BOHHXUQZCBSKLJ-UHFFFAOYSA-N n-[1-(6-dodecylnaphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CC2=CC(CCCCCCCCCCCC)=CC=C2C=1C(C)N=C1CCCCCN1 BOHHXUQZCBSKLJ-UHFFFAOYSA-N 0.000 description 1
- UIUMZAZFFRVYKV-UHFFFAOYSA-N n-[1-(furan-2-yl)hex-4-enyl]-1-azacyclotridecen-2-amine Chemical compound C=1C=COC=1C(CCC=CC)N=C1CCCCCCCCCCCN1 UIUMZAZFFRVYKV-UHFFFAOYSA-N 0.000 description 1
- DXRHUZILJDXPPU-UHFFFAOYSA-N n-[1-[4-(4-phenylbutoxy)phenyl]ethyl]-1-azacyclododecen-2-amine Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(C)N=C1CCCCCCCCCCN1 DXRHUZILJDXPPU-UHFFFAOYSA-N 0.000 description 1
- JSLKVKNOYUOFHD-UHFFFAOYSA-N n-[2-(2-propylphenyl)ethyl]-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound CCCC1=CC=CC=C1CCN=C1NCCCCC1 JSLKVKNOYUOFHD-UHFFFAOYSA-N 0.000 description 1
- DSYBVHJJZWFGGM-UHFFFAOYSA-N n-[cyclobutyl-(3,5-dimethoxyphenyl)methyl]-1-azacyclododecen-2-amine Chemical compound COC1=CC(OC)=CC(C(N=C2NCCCCCCCCCC2)C2CCC2)=C1 DSYBVHJJZWFGGM-UHFFFAOYSA-N 0.000 description 1
- BKIAPSPJAVUZAA-UHFFFAOYSA-N n-[cyclopropyl(phenyl)methyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NC(C=1C=CC=CC=1)C1CC1 BKIAPSPJAVUZAA-UHFFFAOYSA-N 0.000 description 1
- WXTOVHCZRIAZPX-UHFFFAOYSA-N n-[furan-2-yl(phenyl)methyl]-2,3,4,5,6,7-hexahydroazocin-8-amine Chemical compound C1CCCCCC(NC(C=2OC=CC=2)C=2C=CC=CC=2)=N1 WXTOVHCZRIAZPX-UHFFFAOYSA-N 0.000 description 1
- XZEHGVZIFWFDDJ-UHFFFAOYSA-N n-[phenyl(thiophen-2-yl)methyl]-1-azacyclotridecen-2-amine Chemical compound C1CCCCCCCCCCNC1=NC(C=1C=CC=CC=1)C1=CC=CS1 XZEHGVZIFWFDDJ-UHFFFAOYSA-N 0.000 description 1
- IHJZUFLRTVQYLQ-UHFFFAOYSA-N n-benzhydryl-1-azacyclotridecen-2-amine Chemical compound C1CCCCCCCCCCNC1=NC(C=1C=CC=CC=1)C1=CC=CC=C1 IHJZUFLRTVQYLQ-UHFFFAOYSA-N 0.000 description 1
- JOFGGEPLKVPQSC-UHFFFAOYSA-N n-benzhydryl-1-methylpiperidin-2-imine Chemical compound CN1CCCCC1=NC(C=1C=CC=CC=1)C1=CC=CC=C1 JOFGGEPLKVPQSC-UHFFFAOYSA-N 0.000 description 1
- JHDCXXQBOIUZIO-UHFFFAOYSA-N n-benzhydryl-2,3,4,5,6,7-hexahydroazocin-8-amine Chemical compound N1CCCCCCC1=NC(C=1C=CC=CC=1)C1=CC=CC=C1 JHDCXXQBOIUZIO-UHFFFAOYSA-N 0.000 description 1
- DKKOGBSTGPXBRI-UHFFFAOYSA-N n-benzyl-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C=1C=CC=CC=1CNC1=NCCCCC1 DKKOGBSTGPXBRI-UHFFFAOYSA-N 0.000 description 1
- QVFOMDGJICIQEA-UHFFFAOYSA-N n-benzyl-3,4-dihydro-2h-pyrrol-5-amine Chemical compound C=1C=CC=CC=1CNC1=NCCC1 QVFOMDGJICIQEA-UHFFFAOYSA-N 0.000 description 1
- UGHVBROVQWORLB-UHFFFAOYSA-N n-thiophen-2-yl-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C1CCCCNC1=NC1=CC=CS1 UGHVBROVQWORLB-UHFFFAOYSA-N 0.000 description 1
- 229960002644 nifurtimox Drugs 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000024241 parasitism Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 description 1
- 229960001624 pentamidine isethionate Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient 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
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229940118768 plasmodium malariae Drugs 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000028172 protozoa infectious disease Diseases 0.000 description 1
- AQIDWPCFDNAMQW-UHFFFAOYSA-N pyridin-3-ol Chemical compound OC1=C=NC=C[CH]1 AQIDWPCFDNAMQW-UHFFFAOYSA-N 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- 229960000611 pyrimethamine Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- YQDGWZZYGYKDLR-UZVLBLASSA-K sodium stibogluconate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].O1[C@H]([C@H](O)CO)[C@H](O2)[C@H](C([O-])=O)O[Sb]21([O-])O[Sb]1(O)(O[C@H]2C([O-])=O)O[C@H]([C@H](O)CO)[C@@H]2O1 YQDGWZZYGYKDLR-UZVLBLASSA-K 0.000 description 1
- 229960001567 sodium stibogluconate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- VLCYCQAOQCDTCN-ZCFIWIBFSA-N α-difluoromethylornithine Chemical compound NCCC[C@@](N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-ZCFIWIBFSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/49—Cinchonan derivatives, e.g. quinine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26985888A | 1988-11-10 | 1988-11-10 | |
| US269858 | 1988-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02256614A true JPH02256614A (ja) | 1990-10-17 |
Family
ID=23028945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1291439A Pending JPH02256614A (ja) | 1988-11-10 | 1989-11-10 | 薬剤耐性原生動物感染の処置に於けるラクタムイミド類 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0370320B1 (enExample) |
| JP (1) | JPH02256614A (enExample) |
| AT (1) | ATE81004T1 (enExample) |
| AU (1) | AU619613B2 (enExample) |
| DE (1) | DE68903092T2 (enExample) |
| DK (1) | DK561089A (enExample) |
| ES (1) | ES2045348T3 (enExample) |
| GR (1) | GR3006349T3 (enExample) |
| IE (1) | IE893618L (enExample) |
| PH (1) | PH27568A (enExample) |
| ZA (1) | ZA898440B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012511044A (ja) * | 2008-12-08 | 2012-05-17 | アラーガン インコーポレイテッド | アルファ２ｂまたはアルファ２ｂおよびアルファ２ｃアドレノセプターのサブタイプ選択性モジュレーターとしてのｎ‐（１‐フェニル‐２‐アリールエチル）‐４，５‐ジヒドロ‐３ｈ‐ピロール‐２‐アミン化合物 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU625071B2 (en) * | 1988-04-20 | 1992-07-02 | Merrell Dow Pharmaceuticals Inc. | N-alkylamino derivatives of aromatic, tricyclic compounds in the treatment of drug-resistant protozoal infections |
| AU688811B2 (en) * | 1993-10-21 | 1998-03-19 | G.D. Searle & Co. | Amidino derivatives useful as nitric oxide synthase inhibitors |
| ATE222100T1 (de) * | 1993-10-21 | 2002-08-15 | Searle & Co | Amidino-derivate nützlich als no synthase-hemmer |
| ES2151055T3 (es) * | 1994-03-10 | 2000-12-16 | Searle & Co | Derivados de l-n6-(1-iminoetil)lisina utiles como inhibidores de oxido nitrico sintasa. |
| US5684008A (en) * | 1994-11-09 | 1997-11-04 | G. D. Searle & Co. | Aminotetrazole derivatives useful as nitric oxide synthase inhibitors |
| ES2206571T3 (es) * | 1995-04-20 | 2004-05-16 | G.D. SEARLE & CO. | Agentes de amidino ciclico utiles como inhibidores de la oxido nitrico sintasa. |
| US5830917A (en) * | 1995-09-11 | 1998-11-03 | G. D. Searle & Co. | L-N6 -(1-iminoethyl) lysine derivatives useful as nitric oxide synthase inhibitors |
| US5981511A (en) * | 1996-03-06 | 1999-11-09 | G.D. Searle & Co. | Hydroxyamidino derivatives useful as nitric oxide synthase inhibitors |
| US5945408A (en) * | 1996-03-06 | 1999-08-31 | G.D. Searle & Co. | Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors |
| US5981556A (en) * | 1997-07-22 | 1999-11-09 | G.D. Searle & Co. | 1,3-diazolino and 1,3-diazolidino heterocycles as useful nitric oxide synthase inhibitors |
| CA2333691A1 (en) | 1998-06-10 | 1999-12-16 | G.D. Searle & Co. | Heterobicyclic and tricyclic nitric oxide synthase inhibitors |
| US6344473B1 (en) | 2000-08-07 | 2002-02-05 | G.D. Searle & Co. | Imidazoles useful as nitric oxide synthase inhibitors |
| JP2012502009A (ja) * | 2008-09-09 | 2012-01-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 動物有害生物を駆除するためのピロリン−２−イルアミノ化合物 |
| WO2011042565A2 (en) * | 2009-10-09 | 2011-04-14 | Instituut Voor Tropische Geneeskunde | Antiprotozoal activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228130A (en) * | 1978-10-23 | 1980-10-14 | The B. F. Goodrich Company | Coating polymerization reactors with oligomers derived from polyhydric phenols plus a bleach |
-
1989
- 1989-11-06 AU AU44450/89A patent/AU619613B2/en not_active Ceased
- 1989-11-06 ZA ZA898440A patent/ZA898440B/xx unknown
- 1989-11-09 DE DE8989120782T patent/DE68903092T2/de not_active Expired - Fee Related
- 1989-11-09 IE IE893618A patent/IE893618L/xx unknown
- 1989-11-09 DK DK561089A patent/DK561089A/da not_active Application Discontinuation
- 1989-11-09 AT AT89120782T patent/ATE81004T1/de not_active IP Right Cessation
- 1989-11-09 ES ES89120782T patent/ES2045348T3/es not_active Expired - Lifetime
- 1989-11-09 EP EP89120782A patent/EP0370320B1/en not_active Expired - Lifetime
- 1989-11-10 JP JP1291439A patent/JPH02256614A/ja active Pending
- 1989-11-10 PH PH39504A patent/PH27568A/en unknown
-
1992
- 1992-11-26 GR GR920402707T patent/GR3006349T3/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012511044A (ja) * | 2008-12-08 | 2012-05-17 | アラーガン インコーポレイテッド | アルファ２ｂまたはアルファ２ｂおよびアルファ２ｃアドレノセプターのサブタイプ選択性モジュレーターとしてのｎ‐（１‐フェニル‐２‐アリールエチル）‐４，５‐ジヒドロ‐３ｈ‐ピロール‐２‐アミン化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| GR3006349T3 (enExample) | 1993-06-21 |
| DK561089D0 (da) | 1989-11-09 |
| DE68903092T2 (de) | 1993-02-18 |
| ES2045348T3 (es) | 1994-01-16 |
| PH27568A (en) | 1993-08-18 |
| ATE81004T1 (de) | 1992-10-15 |
| AU4445089A (en) | 1990-05-17 |
| ZA898440B (en) | 1990-07-25 |
| DK561089A (da) | 1990-05-11 |
| AU619613B2 (en) | 1992-01-30 |
| IE893618L (en) | 1990-05-10 |
| EP0370320A1 (en) | 1990-05-30 |
| DE68903092D1 (de) | 1992-11-05 |
| EP0370320B1 (en) | 1992-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0370320B1 (en) | Lactamimides in the treatment of drug-resistant protozoal infections | |
| US5219865A (en) | Pharmaceutical combination for the prophylaxis and therapy of malaria | |
| HU202108B (en) | Process for producing pharmaceutical compositions containing serotonine antqgonistic derivatives of indol-carboxylic acid or imidazolyl-methyl-carbazol | |
| NO314830B1 (no) | Anvendelse av carvedilol ved fremstillilng av et medikament for anvendelseved behandling av kongestiv hjertefeil | |
| CA2345406A1 (en) | Analgesic | |
| KR0150630B1 (ko) | 약물 내성 원생 동물 감염증의 치료 및 예방에 유효한 페녹시 및 페닐티오, 아미노 치환 벤조시클로알칸 유도체 | |
| EP0514023B1 (en) | Use of glycine/NMDA receptor ligands for the manufacture of a medicament for the treatment of drug dependence and withdrawal | |
| US5011841A (en) | Treatment of depression | |
| AU2009227092B2 (en) | Combination of a bis-thiazolium salt or a precursor thereof and artemisinin or a derivative thereof for treating acute malaria | |
| EP0338532A2 (en) | N-alkylamino derivates of aromatic, tricyclic compounds in the treatment of drug-resistant protozoal infections | |
| US5373005A (en) | Despiramine in the treatment of drug-resistant malarial infections | |
| NL8002041A (nl) | Werkwijze voor het bereiden van een analgetisch en myotonolytisch geneesmiddel. | |
| JP2001507672A (ja) | Ｃｉｓ―縮合シクロペンテノ―１，２，４―トリオキサン誘導体を含有する抗マラリア組成物 | |
| US4117146A (en) | Method for treating depression and anxiety using phenyl hydrazo compounds | |
| KR100718368B1 (ko) | 상승된 혈압 치료용 시탈로프람 | |
| Brockmeyer et al. | Progress in the Optimization of 4 (1H)-Quinolone Derivatives as Antimalarials Targeting the Erythrocytic, the Exoerythrocytic and the Transmitting Stages of the Malaria Parasite | |
| JP2016164125A (ja) | バベシア症の治療剤及び予防剤 | |
| Barquero | Cipargamin. Antimalarial | |
| US20220265644A1 (en) | Fixed dose combination drug for the treatment of malaria | |
| US7183291B2 (en) | Method for the treatment of malaria by the use of primaquine derivative N1-(3-ethylidinotetrahydrofuran-2-one)-N4- (6-methoxy-8-quinolinyl)-1,4-pentanediamine as gametocytocidal agent | |
| JP2011037814A (ja) | マラリア原虫疾患予防又は治療用の５−ヘテロ環置換イミノ−９−ジアルキルアミノベンゾ［ａ］フェノキサチン化合物又はその塩とアーテミシニン誘導体との組み合わせ | |
| HUP0301925A2 (hu) | Kinolinszármazékokat tartalmazó kombinált készlet malária kezelésére | |
| WO2020092374A1 (en) | Small molecules with anti-protozoan activity | |
| JP5376889B2 (ja) | カンジダ症予防又は治療剤 | |
| EP1055427B1 (en) | Use of primaquine derivatives for the treatment of malaria |