OA10223A - New antiparasitic agents related to the milbemycins and avermectins - Google Patents

New antiparasitic agents related to the milbemycins and avermectins Download PDF

Info

Publication number: OA10223A
Authority: OA; OAPI
Prior art keywords: monosaccharide; cyclohexyl; compound; dihydroavermectin; oximino
Prior art date: 1993-01-18

Application number

OA60688A

Other languages

English (en)

French (fr)

Original Assignee

Pfizer

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.)

1993-01-18

Filing date

1995-07-17

Publication date

1997-10-07

1995-07-17 Application filed by Pfizer filed Critical Pfizer

1997-10-07 Publication of OA10223A publication Critical patent/OA10223A/en

Links

239000003096 antiparasitic agent Substances 0.000 title claims abstract description 6
229940125687 antiparasitic agent Drugs 0.000 title claims description 5
239000005660 Abamectin Substances 0.000 title description 19
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 title description 4
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 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 120
229920006395 saturated elastomer Polymers 0.000 claims abstract description 30
238000001727 in vivo Methods 0.000 claims abstract description 12
125000002252 acyl group Chemical group 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
239000005864 Sulphur Substances 0.000 claims abstract 2
150000002772 monosaccharides Chemical class 0.000 claims description 94
239000000203 mixture Substances 0.000 claims description 53
-1 C2-C Chemical group 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 15
241001465754 Metazoa Species 0.000 claims description 7
238000009472 formulation Methods 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000007818 Grignard reagent Substances 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000000539 amino acid group Chemical group 0.000 claims description 2
125000003435 aroyl group Chemical group 0.000 claims description 2
150000004795 grignard reagents Chemical class 0.000 claims description 2
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims 4
239000003814 drug Substances 0.000 claims 3
229940079593 drug Drugs 0.000 claims 2
238000011321 prophylaxis Methods 0.000 claims 2
238000011282 treatment Methods 0.000 claims 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
208000006004 Flea Infestations Diseases 0.000 claims 1
208000030852 Parasitic disease Diseases 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000006251 butylcarbonyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract description 2
125000005646 oximino group Chemical group 0.000 abstract description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
230000002141 anti-parasite Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 127
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 97
239000000243 solution Substances 0.000 description 77
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
239000000377 silicon dioxide Substances 0.000 description 59
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 53
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 38
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
239000000843 powder Substances 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
238000001819 mass spectrum Methods 0.000 description 29
239000012043 crude product Substances 0.000 description 28
229960004132 diethyl ether Drugs 0.000 description 28
238000000034 method Methods 0.000 description 28
239000000047 product Substances 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 26
229910052938 sodium sulfate Inorganic materials 0.000 description 26
235000011152 sodium sulphate Nutrition 0.000 description 26
239000000284 extract Substances 0.000 description 22
239000000463 material Substances 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 17
235000002639 sodium chloride Nutrition 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
229960002668 sodium chloride Drugs 0.000 description 16
239000011780 sodium chloride Substances 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
BJDCWCLMFKKGEE-CMDXXVQNSA-N chembl252518 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-CMDXXVQNSA-N 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 13
235000015497 potassium bicarbonate Nutrition 0.000 description 13
229910000028 potassium bicarbonate Inorganic materials 0.000 description 13
239000011736 potassium bicarbonate Substances 0.000 description 13
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 13
229910021653 sulphate ion Inorganic materials 0.000 description 13
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
238000004128 high performance liquid chromatography Methods 0.000 description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
229940094025 potassium bicarbonate Drugs 0.000 description 12
238000000746 purification Methods 0.000 description 12
229940093499 ethyl acetate Drugs 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 11
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
125000004043 oxo group Chemical group O=* 0.000 description 7
229960001407 sodium bicarbonate Drugs 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
238000003756 stirring Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000001117 sulphuric acid Substances 0.000 description 6
235000011149 sulphuric acid Nutrition 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class 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 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 5
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
239000004540 pour-on Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 4
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 4
150000001412 amines Chemical class 0.000 description 4
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
244000045947 parasite Species 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 3
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
241000238421 Arthropoda Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000607479 Yersinia pestis Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000000855 fermentation Methods 0.000 description 3
230000004151 fermentation Effects 0.000 description 3
239000006260 foam Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000010791 quenching Methods 0.000 description 3
230000000171 quenching effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000004544 spot-on Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
241000238876 Acari Species 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
241000244206 Nematoda Species 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
241000244031 Toxocara Species 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000002016 disaccharides Chemical class 0.000 description 2
244000078703 ectoparasite Species 0.000 description 2
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230000003301 hydrolyzing effect Effects 0.000 description 2
239000005457 ice water Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000003120 macrolide antibiotic agent Substances 0.000 description 2
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KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
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125000006239 protecting group Chemical group 0.000 description 2
FSWHDPPHBYXOHR-UHFFFAOYSA-N pyridine-3-carbonyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CN=C1 FSWHDPPHBYXOHR-UHFFFAOYSA-N 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
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239000002904 solvent Substances 0.000 description 2
241000894007 species Species 0.000 description 2
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JSKJNCRHZBVPDX-UHFFFAOYSA-N 1,4-dioxane;methanol;hydrate Chemical compound O.OC.C1COCCO1 JSKJNCRHZBVPDX-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
JZVIADUHHSTLSF-SVNGNTECSA-N 22,23-dihydroavermectin b1 monosaccharide Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C(C)C)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)[C@@H](O)[C@H]3OC\C2=C/C=C/[C@@H]1C JZVIADUHHSTLSF-SVNGNTECSA-N 0.000 description 1
PPHVFMDULQHSTJ-UHFFFAOYSA-N 3-(azidomethyl)pyridine Chemical compound [N-]=[N+]=NCC1=CC=CN=C1 PPHVFMDULQHSTJ-UHFFFAOYSA-N 0.000 description 1
WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- 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

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Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Wood Science & Technology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Dentistry (AREA)
Biotechnology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

OA60688A 1993-01-18 1995-07-17 New antiparasitic agents related to the milbemycins and avermectins OA10223A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB939300883A GB9300883D0 (en)	1993-01-18	1993-01-18	Antiparasitic agents

Publications (1)

Publication Number	Publication Date
OA10223A true OA10223A (en)	1997-10-07

Family

ID=10728869

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60688A OA10223A (en)	1993-01-18	1995-07-17	New antiparasitic agents related to the milbemycins and avermectins

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EP (1)	EP0677054B1 (el)
JP (1)	JP2732548B2 (el)
KR (1)	KR0185480B1 (el)
CN (1)	CN1043768C (el)
AP (1)	AP522A (el)
AT (1)	ATE164586T1 (el)
AU (1)	AU679033B2 (el)
BR (2)	BR9405811A (el)
CA (1)	CA2152819C (el)
CZ (1)	CZ284849B6 (el)
DE (2)	DE69409360T2 (el)
DK (1)	DK0677054T3 (el)
EG (1)	EG20582A (el)
ES (1)	ES2113639T3 (el)
FI (1)	FI111727B (el)
GB (1)	GB9300883D0 (el)
GR (1)	GR3026710T3 (el)
HR (1)	HRP940110B1 (el)
HU (1)	HU221505B (el)
IL (1)	IL108306A (el)
LU (1)	LU90518I2 (el)
MA (1)	MA23091A1 (el)
MY (1)	MY141106A (el)
NL (1)	NL300003I2 (el)
NO (2)	NO304835B1 (el)
NZ (1)	NZ259868A (el)
OA (1)	OA10223A (el)
PL (1)	PL176733B1 (el)
RU (1)	RU2125059C1 (el)
SG (1)	SG45131A1 (el)
SK (1)	SK282031B6 (el)
UA (1)	UA42707C2 (el)
WO (1)	WO1994015944A1 (el)
YU (1)	YU49169B (el)
ZA (1)	ZA94310B (el)

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US6136838A (en) *	1998-03-19	2000-10-24	Merck & Co., Inc.	Sulfurpentafluorophenylpyrazoles for controlling ectoparasitic infestations
GB9825402D0 (en)	1998-11-19	1999-01-13	Pfizer Ltd	Antiparasitic formulations
GB9916052D0 (en) *	1999-07-08	1999-09-08	Pfizer Ltd	Anthelmintic compositions
GB9926887D0 (en) *	1999-11-12	2000-01-12	Novartis Ag	Organic compounds
US6787342B2 (en)	2000-02-16	2004-09-07	Merial Limited	Paste formulations
GB0008353D0 (en) *	2000-04-03	2000-05-24	Pfizer Ltd	Method of treating a parasitic infection
GB0108485D0 (en) *	2001-04-04	2001-05-23	Pfizer Ltd	Combination therapy
US20040077703A1 (en)	2002-10-02	2004-04-22	Soll Mark D.	Nodulisporic acid derivative spot-on formulations for combating parasites
US20040219685A1 (en)	2003-01-30	2004-11-04	Applera Corporation	Methods and mixtures pertaining to analyte determination using electrophilic labeling reagents
US7355045B2 (en)	2004-01-05	2008-04-08	Applera Corporation	Isotopically enriched N-substituted piperazine acetic acids and methods for the preparation thereof
US7307169B2 (en)	2004-01-05	2007-12-11	Applera Corporation	Isotopically enriched N-substituted piperazines and methods for the preparation thereof
AU2005223483B2 (en)	2004-03-18	2009-04-23	Zoetis Llc	N-(1-arylpyrazol-4l)sulfonamides and their use as parasiticides
CA2656617C (en)	2006-07-05	2014-10-14	Aventis Agriculture	1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof
DE102007007750A1 (de)	2006-08-17	2008-02-21	Bayer Cropscience Ag	Avermectinderivate
ES2597083T3 (es)	2007-05-15	2017-01-13	Merial, Inc.	Compuestos de ariloazol-2-il cianoetilamino, procedimiento de fabricación y procedimiento de utilización de los mismos
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ES2781828T3 (es)	2008-11-19	2020-09-08	Boehringer Ingelheim Animal Health Usa Inc	Composiciones que comprenden un aril pirazol y/o una formamidina, procedimientos y usos de las mismas
JP5595412B2 (ja)	2008-12-04	2014-09-24	メリアルリミテッド	二量体アベルメクチン及びミルベマイシン誘導体
TWI487486B (zh)	2009-12-01	2015-06-11	Syngenta Participations Ag	以異唑啉衍生物為主之殺蟲化合物
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NZ600845A (en)	2009-12-17	2014-08-29	Merial Ltd	Compositions comprising macrocyclic lactone compounds and spirodioxepinoindoles
EP3078664B1 (en)	2009-12-17	2019-02-20	Merial Inc.	Antiparasitic dihydroazole compositions
BR112012020521B1 (pt)	2010-02-17	2017-12-26	Syngenta Participations Ag	Derivative compounds of isoxazoline, its intermediaries and method for controlling insects, mites, nematodes, or molluscs
EA201201171A1 (ru)	2010-02-22	2013-03-29	Зингента Партисипейшнс Аг	Дигидрофурановые производные в качестве инсектицидных соединений
AU2011220041A1 (en)	2010-02-25	2012-08-23	Syngenta Limited	Process for the preparation of isoxazoline derivatives
UA108641C2 (uk)	2010-04-02	2015-05-25		Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування
CN103153949A (zh)	2010-10-05	2013-06-12	先正达参股股份有限公司	杀虫的吡咯烷-基-芳基-甲酰胺
WO2012049327A2 (en)	2010-10-15	2012-04-19	Syngenta Participations Ag	Pesticidal mixtures
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1993
- 1993-01-18 GB GB939300883A patent/GB9300883D0/en active Pending
1994
- 1994-01-10 IL IL10830694A patent/IL108306A/en not_active IP Right Cessation
- 1994-01-12 DE DE69409360T patent/DE69409360T2/de not_active Expired - Lifetime
- 1994-01-12 AT AT94905061T patent/ATE164586T1/de active
- 1994-01-12 UA UA95073243A patent/UA42707C2/uk unknown
- 1994-01-12 SG SG1995002217A patent/SG45131A1/en unknown
- 1994-01-12 EP EP94905061A patent/EP0677054B1/en not_active Expired - Lifetime
- 1994-01-12 PL PL94309916A patent/PL176733B1/pl unknown
- 1994-01-12 RU RU95117100A patent/RU2125059C1/ru active
- 1994-01-12 AU AU58835/94A patent/AU679033B2/en not_active Expired
- 1994-01-12 SK SK895-95A patent/SK282031B6/sk not_active IP Right Cessation
- 1994-01-12 BR BR9405811A patent/BR9405811A/pt not_active Application Discontinuation
- 1994-01-12 JP JP6515697A patent/JP2732548B2/ja not_active Expired - Lifetime
- 1994-01-12 DE DE2000175003 patent/DE10075003I1/de active Pending
- 1994-01-12 MY MYPI94000081A patent/MY141106A/en unknown
- 1994-01-12 ES ES94905061T patent/ES2113639T3/es not_active Expired - Lifetime
- 1994-01-12 DK DK94905061.1T patent/DK0677054T3/da active
- 1994-01-12 WO PCT/EP1994/000095 patent/WO1994015944A1/en not_active Ceased
- 1994-01-12 NZ NZ259868A patent/NZ259868A/en not_active IP Right Cessation
- 1994-01-12 CA CA002152819A patent/CA2152819C/en not_active Expired - Lifetime
- 1994-01-12 CZ CZ951817A patent/CZ284849B6/cs not_active IP Right Cessation
- 1994-01-13 AP APAP/P/1994/000610A patent/AP522A/en active
- 1994-01-17 ZA ZA94310A patent/ZA94310B/xx unknown
- 1994-01-17 FI FI940218A patent/FI111727B/fi not_active IP Right Cessation
- 1994-01-17 EG EG3094A patent/EG20582A/xx active
- 1994-01-17 HU HU9400131A patent/HU221505B/hu unknown
- 1994-01-17 YU YU1894A patent/YU49169B/sh unknown
- 1994-01-17 MA MA23397A patent/MA23091A1/fr unknown
- 1994-01-18 CN CN94101917A patent/CN1043768C/zh not_active Expired - Lifetime
- 1994-02-15 HR HR9300883.7 patent/HRP940110B1/xx not_active IP Right Cessation
1995
- 1995-07-15 KR KR1019950702924A patent/KR0185480B1/ko not_active Expired - Lifetime
- 1995-07-17 OA OA60688A patent/OA10223A/en unknown
- 1995-07-17 NO NO19952832A patent/NO304835B1/no not_active IP Right Cessation
1996
- 1996-08-21 BR BR1100033-3A patent/BR1100033A/pt active IP Right Grant
1998
- 1998-04-23 GR GR980400898T patent/GR3026710T3/el unknown
2000
- 2000-02-01 NL NL300003C patent/NL300003I2/nl unknown
- 2000-02-09 LU LU90518C patent/LU90518I2/fr unknown
2001
- 2001-06-11 NO NO2001010C patent/NO2001010I1/no unknown

Also Published As

Publication number	Publication date
FI940218A0 (fi)	1994-01-17
KR0185480B1 (en)	1999-04-01
CA2152819C (en)	1999-03-16
NO952832D0 (no)	1995-07-17
CZ181795A3 (en)	1996-02-14
EP0677054A1 (en)	1995-10-18
CN1043768C (zh)	1999-06-23
DE10075003I1 (de)	2000-06-29
YU1894A (sh)	1997-01-08
AP522A (en)	1996-09-05
JPH08500842A (ja)	1996-01-30
HUT70411A (en)	1995-10-30
HU9400131D0 (en)	1994-05-30
KR960700259A (ko)	1996-01-19
CZ284849B6 (cs)	1999-03-17
WO1994015944A1 (en)	1994-07-21
CN1099394A (zh)	1995-03-01
SK89595A3 (en)	1996-04-03
LU90518I2 (fr)	2000-04-10
PL176733B1 (pl)	1999-07-30
MA23091A1 (fr)	1994-10-01
NO2001010I1 (no)	2001-07-02
DE69409360T2 (de)	1998-07-23
IL108306A (en)	1998-08-16
EP0677054B1 (en)	1998-04-01
DE69409360D1 (de)	1998-05-07
SG45131A1 (en)	1998-01-16
EG20582A (en)	1999-08-30
ATE164586T1 (de)	1998-04-15
IL108306A0 (en)	1994-04-12
JP2732548B2 (ja)	1998-03-30
HU221505B (en)	2002-10-28
HRP940110A2 (en)	1996-12-31
NL300003I1 (nl)	2000-04-03
FI940218L (fi)	1994-07-19
FI111727B (fi)	2003-09-15
GB9300883D0 (en)	1993-03-10
GR3026710T3 (en)	1998-07-31
NZ259868A (en)	1997-01-29
SK282031B6 (sk)	2001-10-08
AU5883594A (en)	1994-08-15
AP9400610A0 (en)	1994-01-31
DK0677054T3 (da)	1998-06-02
PL309916A1 (en)	1995-11-13
NO952832L (no)	1995-07-28
CA2152819A1 (en)	1994-07-21
YU49169B (sh)	2004-05-12
AU679033B2 (en)	1997-06-19
UA42707C2 (uk)	2001-11-15
BR1100033A (pt)	2000-06-20
RU2125059C1 (ru)	1999-01-20
ES2113639T3 (es)	1998-05-01
NL300003I2 (nl)	2000-08-01
HRP940110B1 (en)	2001-02-28
BR9405811A (pt)	1995-12-05
MY141106A (en)	2010-03-15
ZA94310B (en)	1995-07-17
NO304835B1 (no)	1999-02-22

Publication	Publication Date	Title
OA10223A (en)	1997-10-07	New antiparasitic agents related to the milbemycins and avermectins
US5981500A (en)	1999-11-09	Antiparasitic agents related to the milbemycins and avermectins
CA1320719C (en)	1993-07-27	Avermectin derivatives
JPH0753734B2 (ja)	1995-06-07	アベルメクチンおよびミルベマイシンの１３−ケト，１３−イミノ，および１３−アミノ誘導体
JPS61200993A (ja)	1986-09-05	新規なアベルメクチンアグリコンの置換された又は置換されていない１３‐（アルコキシ）メトキシ誘導体
AU658268B2 (en)	1995-04-06	Antiparasitic avermectin and milbemycin derivatives
AU683906B2 (en)	1997-11-27	Antiparasitic agents
JPH0386885A (ja)	1991-04-11	アベルメクチン誘導体
DE3785628T2 (de)	1993-09-23	Delta 22-derivate von ll-f28249-verbindungen.
AU680290B2 (en)	1997-07-24	Antiparasitic agents
EP0712411B1 (en)	1997-06-11	Antiparasitic agents
DE3885346T2 (de)	1994-05-19	23-Oxo (Keto) und 23-Imino-Derivate von Mono- und Diepoxy LL-F28249 Verbindungen.
JPH08510758A (ja)	1996-11-12	ドラメクチンの製造方法および駆虫性中間体
JPH0219382A (ja)	1990-01-23	開裂されたフラン環及び８ａヒドロキシ基を有する新規アベルメクチン類
SI9400118A (sl)	1995-10-31	Sredstva proti parazitom, ki so v sorodu z milbemicini in avermektini
JPH07501800A (ja)	1995-02-23	駆虫剤