OA10110A - Soluble alkyl ¬5- ¬amino (phenyl) methyl¾ -1h- benzimidazol-2-yl¾ carbamate anthelmintics - Google Patents

Soluble alkyl ¬5- ¬amino (phenyl) methyl¾ -1h- benzimidazol-2-yl¾ carbamate anthelmintics Download PDF

Info

Publication number: OA10110A
Authority: OA; OAPI
Prior art keywords: methyl; carbamate; amino; benzimidazol; rnethyl
Prior art date: 1992-05-12

Application number

OA60580A

Other languages

English (en)

Inventor

Leroy B Townsend

Dean S Wise

Ram Siya

Original Assignee

Univ Michigan

Priority date (The priority date 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 date listed.)

1992-05-12

Filing date

1994-11-11

Publication date

1996-12-18

1994-11-11 Application filed by Univ Michigan filed Critical Univ Michigan

1996-12-18 Publication of OA10110A publication Critical patent/OA10110A/en

Links

230000000507 anthelmentic effect Effects 0.000 title claims abstract description 8
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title claims description 47
125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 21
125000000217 alkyl group Chemical group 0.000 title claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 10
229940124339 anthelmintic agent Drugs 0.000 title description 3
239000000921 anthelmintic agent Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 54
-1 alkyl [5-(amino (phenyl)methyl)-2H-benzimidazol-2-yl]carbamates Chemical class 0.000 claims abstract description 24
241000124008 Mammalia Species 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 11
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
208000015181 infectious disease Diseases 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
230000001001 anti-filiarial effect Effects 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 3
RDHZNPOGPNNKFU-UHFFFAOYSA-N methyl n-[6-[amino-(4-fluorophenyl)methyl]-1h-benzimidazol-2-yl]carbamate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(N)C1=CC=C(F)C=C1 RDHZNPOGPNNKFU-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
229950006098 orthocaine Drugs 0.000 claims 1
238000000034 method Methods 0.000 abstract description 31
208000006968 Helminthiasis Diseases 0.000 abstract description 6
208000014837 parasitic helminthiasis infectious disease Diseases 0.000 abstract description 6
150000003839 salts Chemical class 0.000 abstract description 6
230000015572 biosynthetic process Effects 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 35
238000007920 subcutaneous administration Methods 0.000 description 33
229910001868 water Inorganic materials 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
241000282472 Canis lupus familiaris Species 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
239000000243 solution Substances 0.000 description 20
239000007787 solid Substances 0.000 description 18
238000001914 filtration Methods 0.000 description 17
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 12
239000000843 powder Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
238000007918 intramuscular administration Methods 0.000 description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
235000011114 ammonium hydroxide Nutrition 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000002775 capsule Substances 0.000 description 8
239000002552 dosage form Substances 0.000 description 8
229940079593 drug Drugs 0.000 description 8
239000003814 drug Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
150000004657 carbamic acid derivatives Chemical class 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000012458 free base Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000003826 tablet Substances 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
241000699696 Meriones Species 0.000 description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
229940043379 ammonium hydroxide Drugs 0.000 description 5
239000002585 base Substances 0.000 description 5
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 5
239000007924 injection Substances 0.000 description 5
238000002347 injection Methods 0.000 description 5
229920000053 polysorbate 80 Polymers 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 4
SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d 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(O[C@@H]([C@@H](C)CC4)C(C)C)O3)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.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
XNRHTMDHGDWBGP-UHFFFAOYSA-N carbamic acid;hydrochloride Chemical compound Cl.NC(O)=O XNRHTMDHGDWBGP-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
229960002418 ivermectin Drugs 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000312 peanut oil Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
230000002194 synthesizing effect Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
201000006353 Filariasis Diseases 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
235000019483 Peanut oil Nutrition 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000002612 dispersion medium Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
230000000968 intestinal effect Effects 0.000 description 3
239000008101 lactose Substances 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
239000007929 subcutaneous injection Substances 0.000 description 3
238000010254 subcutaneous injection Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
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 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000244185 Ascaris lumbricoides Species 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
241000243982 Brugia pahangi Species 0.000 description 2
125000006519 CCH3 Chemical group 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
238000011887 Necropsy Methods 0.000 description 2
241000243985 Onchocerca volvulus Species 0.000 description 2
239000004353 Polyethylene glycol 8000 Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000011149 active material Substances 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
229940121375 antifungal agent Drugs 0.000 description 2
239000003429 antifungal agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
210000001142 back Anatomy 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
230000009977 dual effect Effects 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
CPEUVMUXAHMANV-UHFFFAOYSA-N flubendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=C(F)C=C1 CPEUVMUXAHMANV-UHFFFAOYSA-N 0.000 description 2
229960004500 flubendazole Drugs 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
210000000548 hind-foot Anatomy 0.000 description 2
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 2
150000007857 hydrazones Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
230000007794 irritation Effects 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
XLRFLCKVFRLIJZ-UHFFFAOYSA-N methyl n-[6-[amino(phenyl)methyl]-1h-benzimidazol-2-yl]carbamate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(N)C1=CC=CC=C1 XLRFLCKVFRLIJZ-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
208000002042 onchocerciasis Diseases 0.000 description 2
239000002245 particle Substances 0.000 description 2
229940085678 polyethylene glycol 8000 Drugs 0.000 description 2
235000019446 polyethylene glycol 8000 Nutrition 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229960004063 propylene glycol Drugs 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
229960005314 suramin Drugs 0.000 description 2
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 2
239000000375 suspending agent Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
235000010487 tragacanth Nutrition 0.000 description 2
239000000196 tragacanth Substances 0.000 description 2
229940116362 tragacanth Drugs 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 1
PVQOAKGNTMVHHS-UHFFFAOYSA-N (6-benzoyl-1h-benzimidazol-2-yl)carbamic acid Chemical compound C1=C2NC(NC(=O)O)=NC2=CC=C1C(=O)C1=CC=CC=C1 PVQOAKGNTMVHHS-UHFFFAOYSA-N 0.000 description 1
WCBVUETZRWGIJQ-UHFFFAOYSA-N 2-[[(methoxycarbonylamino)-(2-nitro-5-propylsulfanylanilino)methylidene]amino]ethanesulfonic acid Chemical compound CCCSC1=CC=C([N+]([O-])=O)C(NC(NC(=O)OC)=NCCS(O)(=O)=O)=C1 WCBVUETZRWGIJQ-UHFFFAOYSA-N 0.000 description 1
SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
241000244044 Acanthocheilonema Species 0.000 description 1
241000955932 Acraea lia Species 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241001465677 Ancylostomatoidea Species 0.000 description 1
101100508377 Arabidopsis thaliana TIF4A-3 gene Proteins 0.000 description 1
239000001904 Arabinogalactan Substances 0.000 description 1
229920000189 Arabinogalactan Polymers 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
201000004569 Blindness Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
RUQWNLMKQFTOKQ-UHFFFAOYSA-N CCOC(=O)NC1=NC2=C(N1)C=C(C=C2)C(C3=CC=C(C=C3)F)N Chemical compound CCOC(=O)NC1=NC2=C(N1)C=C(C=C2)C(C3=CC=C(C=C3)F)N RUQWNLMKQFTOKQ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000498256 Enterobius Species 0.000 description 1
206010015548 Euthanasia Diseases 0.000 description 1
206010016675 Filariasis lymphatic Diseases 0.000 description 1
241000233866 Fungi Species 0.000 description 1
229920000926 Galactomannan Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010061201 Helminthic infection Diseases 0.000 description 1
208000032843 Hemorrhage Diseases 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
208000037263 Lymphatic filariasis Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 description 1
RAOCRURYZCVHMG-UHFFFAOYSA-N N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)NC2=C1 RAOCRURYZCVHMG-UHFFFAOYSA-N 0.000 description 1
241000498270 Necator americanus Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
QLWWFEPVZFOIKT-UHFFFAOYSA-N OC(C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1)C1=CC=CC=C1 Chemical compound OC(C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1)C1=CC=CC=C1 QLWWFEPVZFOIKT-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
241000022563 Rema Species 0.000 description 1
244000117054 Rungia klossii Species 0.000 description 1
235000002492 Rungia klossii Nutrition 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
241000486415 Trichiura Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 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
239000013543 active substance Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
229960002669 albendazole Drugs 0.000 description 1
HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000007815 allergy Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
UFLRJROFPAGRPN-UHFFFAOYSA-N amocarzine Chemical compound C1CN(C)CCN1C(=S)NC(C=C1)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 UFLRJROFPAGRPN-UHFFFAOYSA-N 0.000 description 1
229950006914 amocarzine Drugs 0.000 description 1
239000002501 antifilarial agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
235000019312 arabinogalactan Nutrition 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001556 benzimidazoles Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
208000034158 bleeding Diseases 0.000 description 1
231100000319 bleeding Toxicity 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
UKAWXALBBYVEGN-UHFFFAOYSA-N carbamic acid;dihydrochloride Chemical class Cl.Cl.NC(O)=O UKAWXALBBYVEGN-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000006071 cream Substances 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
229960003974 diethylcarbamazine Drugs 0.000 description 1
RCKMWOKWVGPNJF-UHFFFAOYSA-N diethylcarbamazine Chemical compound CCN(CC)C(=O)N1CCN(C)CC1 RCKMWOKWVGPNJF-UHFFFAOYSA-N 0.000 description 1
UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
238000003821 enantio-separation Methods 0.000 description 1
DBHQLYNUUHIBIM-UHFFFAOYSA-N ethyl n-[6-[c-(4-fluorophenyl)-n-methoxycarbonimidoyl]-1h-benzimidazol-2-yl]carbamate Chemical compound C=1C=C2NC(NC(=O)OCC)=NC2=CC=1C(=NOC)C1=CC=C(F)C=C1 DBHQLYNUUHIBIM-UHFFFAOYSA-N 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
229960003699 evans blue Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229940077203 fatal-plus Drugs 0.000 description 1
229960005473 fenbendazole Drugs 0.000 description 1
HDDSHPAODJUKPD-UHFFFAOYSA-N fenbendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 HDDSHPAODJUKPD-UHFFFAOYSA-N 0.000 description 1
208000005239 filarial elephantiasis Diseases 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000001087 glyceryl triacetate Substances 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
244000000013 helminth Species 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
229960001614 levamisole Drugs 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000006210 lotion Substances 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000002751 lymph Anatomy 0.000 description 1
210000001165 lymph node Anatomy 0.000 description 1
230000001926 lymphatic effect Effects 0.000 description 1
230000001638 macrofilaricidal effect Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
229960003439 mebendazole Drugs 0.000 description 1
OPXLLQIJSORQAM-UHFFFAOYSA-N mebendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(=O)C1=CC=CC=C1 OPXLLQIJSORQAM-UHFFFAOYSA-N 0.000 description 1
NVWUMCATGHETTI-UHFFFAOYSA-N methyl n-[6-(n-methoxy-c-phenylcarbonimidoyl)-1h-benzimidazol-2-yl]carbamate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(=NOC)C1=CC=CC=C1 NVWUMCATGHETTI-UHFFFAOYSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000035772 mutation Effects 0.000 description 1
229950006716 netobimin Drugs 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960002762 oxibendazole Drugs 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000003108 parasitologic effect Effects 0.000 description 1
229950007337 parbendazole Drugs 0.000 description 1
230000007170 pathology Effects 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229960000292 pectin Drugs 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
239000008213 purified water Substances 0.000 description 1
QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
229960004546 thiabendazole Drugs 0.000 description 1
239000004308 thiabendazole Substances 0.000 description 1
235000010296 thiabendazole Nutrition 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000009466 transformation Effects 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

OA60580A 1992-05-12 1994-11-11 Soluble alkyl ¬5- ¬amino (phenyl) methyl¾ -1h- benzimidazol-2-yl¾ carbamate anthelmintics OA10110A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/881,910 US5278181A (en)	1992-05-12	1992-05-12	Soluble alkyl[5-[amino (phenyl)methyl]-1H-benzimidazol-2-yl] carbamate anthelmintics

Publications (1)

Publication Number	Publication Date
OA10110A true OA10110A (en)	1996-12-18

Family

ID=25379452

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60580A OA10110A (en)	1992-05-12	1994-11-11	Soluble alkyl ¬5- ¬amino (phenyl) methyl¾ -1h- benzimidazol-2-yl¾ carbamate anthelmintics

Country Status (5)

Country	Link
US (1)	US5278181A (fr)
EP (1)	EP0639974A4 (fr)
AU (1)	AU4227593A (fr)
OA (1)	OA10110A (fr)
WO (1)	WO1993023037A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR112014026184B1 (pt) *	2012-04-20	2019-04-24	Merial, Inc.	Composições parasiticídicas compreendendo derivados de benzimidazol, métodos e seus usos

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3657267A (en) *	1969-06-20	1972-04-18	Janssen Pharmaceutica Nv	Benzimidazole carbamates
US4005202A (en) *	1974-02-11	1977-01-25	Syntex (U.S.A.) Inc.	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
DE2453210C3 (de) *	1974-11-09	1979-11-22	Bayer Ag, 5090 Leverkusen	Bekämpfung von Pilzen der Gattung Hehmnthosporium mit Dimethyipyrazolylbenzimidazol
USRE30990E (en) *	1976-07-16	1982-07-06	E. R. Squibb & Sons, Inc.	Benzimidazole derivatives, compositions thereof and method of use as anthelmintics
DE2845537A1 (de) *	1978-10-19	1980-04-30	Bayer Ag	Benzimidazolylcarbamidsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
US4512998A (en) *	1980-10-20	1985-04-23	Schering Corporation	Anthelmintic benzimidazole carbamates
US4435418A (en) *	1982-12-13	1984-03-06	Smithkline Beckman Corporation	5-Phenylethenylbenzimidazoles
US4826862A (en) *	1988-02-12	1989-05-02	Janssen Pharmaceutica, N.V.	Anthelminthic [(5(6) (1H-azole-1-ylmethyl)benzimidazole]carbamates

1992
- 1992-05-12 US US07/881,910 patent/US5278181A/en not_active Expired - Fee Related
1993
- 1993-05-03 WO PCT/US1993/004109 patent/WO1993023037A1/fr not_active Ceased
- 1993-05-03 AU AU42275/93A patent/AU4227593A/en not_active Abandoned
- 1993-05-03 EP EP93910966A patent/EP0639974A4/fr not_active Withdrawn
1994
- 1994-11-11 OA OA60580A patent/OA10110A/en unknown

Also Published As

Publication number	Publication date
EP0639974A4 (fr)	1996-07-24
WO1993023037A1 (fr)	1993-11-25
AU4227593A (en)	1993-12-13
US5278181A (en)	1994-01-11
EP0639974A1 (fr)	1995-03-01

Publication	Publication Date	Title
EP0042593B1 (fr)	1985-04-03	Aryloxypropanolamines, procédé pour leur préparation et médicament les contenant
DE69617273T2 (de)	2002-07-25	Heterocyclisch substituierte cyclopentanderivate.
DE60216952T2 (de)	2007-07-05	Beta-carbolin-derivate als ptp-inhibitoren
DE69132691T2 (de)	2002-06-20	Indolderivate als 5-HT1-like Agonisten
DE60202958T2 (de)	2006-04-06	Stabiles polymorph von flibanserin, industrielles verfahren zu dessen herstellung und dessen verwendung zur herstellung von medikamenten
US4512998A (en)	1985-04-23	Anthelmintic benzimidazole carbamates
IL41170A (en)	1977-01-31	2-Carbalkoxy-amino-benzimidazole) 6 (5-Phenyl sites with activity against worms and a process for their preparation
TW200533640A (en)	2005-10-16	Florfenicol prodrug having improved water solubility
US20100093770A1 (en)	2010-04-15	Therapeutic agent for glaucoma containing adenosine derivative as active ingredient
DE60214569T2 (de)	2007-05-03	Harnstoffverbindungen mit antiproteolytischer wirkung
DE2836616A1 (de)	1979-03-08	Alpha -halogenmethylderivate von aminen
WO2005042495A1 (fr)	2005-05-12	Composes de (benzimidazol-2-yl)-phenyl-phenyl-uree et procedes d'inhibition de l'activite de l'heparanase
CH640820A5 (de)	1984-01-31	Acetylenderivate von aminen.
PL160685B1 (pl)	1993-04-30	Sposób wytwarzania nowych czwartorzedowych zwiazków amoniowych PL PL PL PL PL PL PL
DE2363348C3 (de)	1981-04-30	Substituierte 5 (6)-Phenoxy-benzimidazol-2-carbaminsäuremethylester, deren Herstellung und diese enthaltende Anthelminthika
EP1913009B1 (fr)	2010-05-12	Nouveaux benzimidazolyl(thio)carbamates ayant une activite antiparasitaire et synthese de ceux-ci
JPH01228986A (ja)	1989-09-12	［（５（６）（１ｈ―アゾール―１―イルメチル）ベンズイミダゾール］カーバメート
OA10110A (en)	1996-12-18	Soluble alkyl ¬5- ¬amino (phenyl) methyl¾ -1h- benzimidazol-2-yl¾ carbamate anthelmintics
WO2008027340A2 (fr)	2008-03-06	Formulations ophtalmiques locales
US4348406A (en)	1982-09-07	Novel guanidine derivatives
DE69813539T2 (de)	2003-12-18	Neue amid-derivate und medizinische zusammensetzungen die diese enthalten
CS195332B2 (en)	1980-01-31	Method of producing indazolyl-/4/-oxy-propanolamines
BG106205A (bg)	2002-07-31	Полиморфи на кристален (2-бензхидрил-1-азабицикло/2,2,2/окт-3-ил)-(5-изопропил-2-метоксибензил)-амониев хлорид като антагонисти на nk-1 рецептор
DE3689321T2 (de)	1994-04-28	Hydroxyalkoxy-4-phenylpropylindolderivate, ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammensetzungen die sie enthalten.
US3661966A (en)	1972-05-09	Bisammonium compounds and process for preparing them