ES2393965T3 - Compuestos de tioamida, procedimiento de preparación y procedimiento de uso de los mismos - Google Patents
Compuestos de tioamida, procedimiento de preparación y procedimiento de uso de los mismos Download PDFInfo
- Publication number
- ES2393965T3 ES2393965T3 ES09744007T ES09744007T ES2393965T3 ES 2393965 T3 ES2393965 T3 ES 2393965T3 ES 09744007 T ES09744007 T ES 09744007T ES 09744007 T ES09744007 T ES 09744007T ES 2393965 T3 ES2393965 T3 ES 2393965T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- halo
- alkylthio
- alkoxy
- sulfinyl
- 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.)
- Active
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- 238000000034 method Methods 0.000 title claims description 46
- 238000002360 preparation method Methods 0.000 title description 15
- 150000003556 thioamides Chemical class 0.000 title description 10
- -1 thioamide compound Chemical class 0.000 claims abstract description 228
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 163
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 72
- 150000002367 halogens Chemical class 0.000 claims abstract description 72
- 125000001424 substituent group Chemical group 0.000 claims abstract description 68
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 60
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 58
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 57
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 52
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 51
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 40
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 35
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 33
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 14
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 10
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 4
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 194
- 239000000460 chlorine Substances 0.000 claims description 171
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- 241001465754 Metazoa Species 0.000 claims description 20
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- 241000243974 Haemonchus contortus Species 0.000 claims description 5
- ZGSDJMADBJCNPN-UHFFFAOYSA-N [S-][NH3+] Chemical compound [S-][NH3+] ZGSDJMADBJCNPN-UHFFFAOYSA-N 0.000 claims description 5
- 244000000013 helminth Species 0.000 claims description 5
- 108010034145 Helminth Proteins Proteins 0.000 claims description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 2
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 abstract 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 abstract 1
- 239000000203 mixture Substances 0.000 description 106
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 94
- 238000009472 formulation Methods 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000003795 chemical substances by application Substances 0.000 description 34
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 30
- 239000004094 surface-active agent Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- 239000011734 sodium Substances 0.000 description 24
- 229910052708 sodium Inorganic materials 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 23
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 22
- 229940083542 sodium Drugs 0.000 description 22
- 239000013543 active substance Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 239000005918 Milbemectin Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 239000005660 Abamectin Substances 0.000 description 13
- 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 13
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000003981 vehicle Substances 0.000 description 12
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- 239000002917 insecticide Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 230000000361 pesticidal effect Effects 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 229920001223 polyethylene glycol Polymers 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 150000003839 salts Chemical group 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 244000078703 ectoparasite Species 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 229960005150 glycerol Drugs 0.000 description 10
- 235000011187 glycerol Nutrition 0.000 description 10
- 239000004530 micro-emulsion Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 238000004293 19F NMR spectroscopy Methods 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 239000006072 paste Substances 0.000 description 9
- 239000003755 preservative agent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 241000255925 Diptera Species 0.000 description 8
- 241001481703 Rhipicephalus <genus> Species 0.000 description 8
- 241000607479 Yersinia pestis Species 0.000 description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 8
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 8
- 229920000053 polysorbate 80 Polymers 0.000 description 8
- 229960004063 propylene glycol Drugs 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 241000124008 Mammalia Species 0.000 description 7
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000003093 cationic surfactant Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 125000004438 haloalkoxy group Chemical group 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 7
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 7
- 229920000136 polysorbate Polymers 0.000 description 7
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003096 antiparasitic agent Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000006184 cosolvent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- 235000003599 food sweetener Nutrition 0.000 description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 6
- 239000003120 macrolide antibiotic agent Substances 0.000 description 6
- 229940041033 macrolides Drugs 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 5
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- 241000282326 Felis catus Species 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 5
- 230000000507 anthelmentic effect Effects 0.000 description 5
- 239000000921 anthelmintic agent Substances 0.000 description 5
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- 230000000694 effects Effects 0.000 description 5
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- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000003906 humectant Substances 0.000 description 5
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- 150000002596 lactones Chemical class 0.000 description 5
- 235000010445 lecithin Nutrition 0.000 description 5
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- 229940067606 lecithin Drugs 0.000 description 5
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
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- 239000011591 potassium Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
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- 239000004562 water dispersible granule Substances 0.000 description 5
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 4
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- 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 4
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- 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 4
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 4
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- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 4
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- 229960001670 trilostane Drugs 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 229960003223 tripelennamine Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
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- 239000000273 veterinary drug Substances 0.000 description 1
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- 229960002110 vincristine sulfate Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- QYEFBJRXKKSABU-UHFFFAOYSA-N xylazine hydrochloride Chemical compound Cl.CC1=CC=CC(C)=C1NC1=NCCCS1 QYEFBJRXKKSABU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
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- 239000010457 zeolite Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- UBQNRHZMVUUOMG-UHFFFAOYSA-N zonisamide Chemical compound C1=CC=C2C(CS(=O)(=O)N)=NOC2=C1 UBQNRHZMVUUOMG-UHFFFAOYSA-N 0.000 description 1
- 229960002911 zonisamide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Dermatology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US107114P | 1998-11-05 | ||
| US10711408P | 2008-10-21 | 2008-10-21 | |
| PCT/US2009/061337 WO2010048191A1 (en) | 2008-10-21 | 2009-10-20 | Thioamide compounds, method of making and method of using thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2393965T3 true ES2393965T3 (es) | 2013-01-03 |
| ES2393965T9 ES2393965T9 (es) | 2013-07-19 |
Family
ID=41404569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09744007T Active ES2393965T3 (es) | 2008-10-21 | 2009-10-20 | Compuestos de tioamida, procedimiento de preparación y procedimiento de uso de los mismos |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7964621B2 (enExample) |
| EP (1) | EP2358687B9 (enExample) |
| JP (1) | JP5614853B2 (enExample) |
| KR (2) | KR101782308B1 (enExample) |
| CN (1) | CN102239151B (enExample) |
| AU (1) | AU2009307736B2 (enExample) |
| BR (1) | BRPI0920145B8 (enExample) |
| CA (1) | CA2741186C (enExample) |
| CL (1) | CL2011000917A1 (enExample) |
| EA (1) | EA026649B1 (enExample) |
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| MX (1) | MX2011004217A (enExample) |
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| CN104610110A (zh) * | 2014-03-12 | 2015-05-13 | 广东东阳光药业有限公司 | 一种制备4-取代硫代苯甲酰胺衍生物的方法 |
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| BRPI0920145B8 (pt) | 2021-05-25 |
| EA201100666A1 (ru) | 2011-12-30 |
| JP2012506441A (ja) | 2012-03-15 |
| EA026649B1 (ru) | 2017-05-31 |
| KR20110071140A (ko) | 2011-06-28 |
| WO2010048191A1 (en) | 2010-04-29 |
| EP2358687B1 (en) | 2012-09-19 |
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| US8314146B2 (en) | 2012-11-20 |
| ZA201103033B (en) | 2012-02-29 |
| ES2393965T9 (es) | 2013-07-19 |
| EP2358687A1 (en) | 2011-08-24 |
| BRPI0920145A2 (pt) | 2017-06-06 |
| CN102239151B (zh) | 2014-07-02 |
| CA2741186C (en) | 2016-07-19 |
| KR20170003704A (ko) | 2017-01-09 |
| AU2009307736B2 (en) | 2015-02-05 |
| US20100130565A1 (en) | 2010-05-27 |
| AU2009307736A1 (en) | 2010-04-29 |
| KR101782308B1 (ko) | 2017-09-27 |
| JP5614853B2 (ja) | 2014-10-29 |
| CN102239151A (zh) | 2011-11-09 |
| US20110190231A1 (en) | 2011-08-04 |
| BRPI0920145B1 (pt) | 2021-03-30 |
| MX2011004217A (es) | 2011-06-20 |
| CL2011000917A1 (es) | 2011-09-16 |
| EP2358687B9 (en) | 2013-04-17 |
| CA2741186A1 (en) | 2010-04-29 |
| NZ592382A (en) | 2013-03-28 |
| KR101782311B1 (ko) | 2017-09-27 |
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