DK171255B1 - Makrolidforbindelser, præparater indeholdende forbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne - Google Patents

Makrolidforbindelser, præparater indeholdende forbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne Download PDF

Info

Publication number: DK171255B1
Authority: DK; Denmark
Prior art keywords: compounds; group; compound; formula; pest control
Prior art date: 1987-09-11

Application number

DK505288A

Other languages

Danish (da)

English (en)

Other versions

DK505288D0 (da

DK505288A (da

Inventor

Michael V J Ramsay

Richard Bell

Derek R Sutherland

Peter D Howes

Edward P Tiley

Original Assignee

American Cyanamid Co

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.)

1987-09-11

Filing date

1988-09-09

Publication date

1996-08-12

1988-09-09 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1988-09-09 Publication of DK505288D0 publication Critical patent/DK505288D0/da

1989-03-12 Publication of DK505288A publication Critical patent/DK505288A/da

1996-08-12 Application granted granted Critical

1996-08-12 Publication of DK171255B1 publication Critical patent/DK171255B1/da

Links

150000001875 compounds Chemical class 0.000 title claims description 88
238000002360 preparation method Methods 0.000 title claims description 19
241000607479 Yersinia pestis Species 0.000 title claims description 17
239000003814 drug Substances 0.000 title claims description 16
238000000034 method Methods 0.000 title claims description 13
239000003120 macrolide antibiotic agent Substances 0.000 title claims description 5
229940079593 drug Drugs 0.000 title description 3
239000000203 mixture Substances 0.000 claims description 36
239000000969 carrier Substances 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 2
238000003898 horticulture Methods 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
239000004480 active ingredient Substances 0.000 description 38
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 24
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
239000002904 solvent Substances 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
-1 boli Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 13
239000000843 powder Substances 0.000 description 13
239000008187 granular material Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 11
235000019441 ethanol Nutrition 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
238000009472 formulation Methods 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
239000000047 product Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000003826 tablet Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
235000019445 benzyl alcohol Nutrition 0.000 description 8
239000006260 foam Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
239000003381 stabilizer Substances 0.000 description 8
241000282412 Homo Species 0.000 description 7
241000244206 Nematoda Species 0.000 description 7
239000012267 brine Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
229920000168 Microcrystalline cellulose Polymers 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000008108 microcrystalline cellulose Substances 0.000 description 6
229940016286 microcrystalline cellulose Drugs 0.000 description 6
235000019813 microcrystalline cellulose Nutrition 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 6
239000000375 suspending agent Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
241000238876 Acari Species 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
244000078703 ectoparasite Species 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
235000003911 Arachis Nutrition 0.000 description 4
244000105624 Arachis hypogaea Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
229920002651 Polysorbate 85 Polymers 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
150000008282 halocarbons Chemical class 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002736 nonionic surfactant Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229920001983 poloxamer Polymers 0.000 description 4
229940113171 polysorbate 85 Drugs 0.000 description 4
230000009467 reduction Effects 0.000 description 4
239000007921 spray Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000254173 Coleoptera Species 0.000 description 3
241000255925 Diptera Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229940083916 aluminum distearate Drugs 0.000 description 3
RDIVANOKKPKCTO-UHFFFAOYSA-K aluminum;octadecanoate;hydroxide Chemical compound [OH-].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O RDIVANOKKPKCTO-UHFFFAOYSA-K 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
239000008365 aqueous carrier Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000002674 ointment Substances 0.000 description 3
239000006072 paste Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
238000011146 sterile filtration Methods 0.000 description 3
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000002562 thickening agent Substances 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
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 2
239000005909 Kieselgur Substances 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
241001494479 Pecora Species 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
241001649229 Psoroptes Species 0.000 description 2
241001481703 Rhipicephalus <genus> Species 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
235000013871 bee wax Nutrition 0.000 description 2
239000012166 beeswax Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
239000003093 cationic surfactant Substances 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000003240 coconut oil Substances 0.000 description 2
235000019864 coconut oil Nutrition 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000003349 gelling agent Substances 0.000 description 2
229940074076 glycerol formal Drugs 0.000 description 2
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 2
239000001087 glyceryl triacetate Substances 0.000 description 2
235000013773 glyceryl triacetate Nutrition 0.000 description 2
239000010440 gypsum Substances 0.000 description 2
229910052602 gypsum Inorganic materials 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
244000144972 livestock Species 0.000 description 2
239000006210 lotion Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
UNCAXIZUVRKBMN-UHFFFAOYSA-N o-(4-methylphenyl) chloromethanethioate Chemical compound CC1=CC=C(OC(Cl)=S)C=C1 UNCAXIZUVRKBMN-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
244000045947 parasite Species 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
239000000049 pigment Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 2
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 2
229940113124 polysorbate 60 Drugs 0.000 description 2
229940068968 polysorbate 80 Drugs 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
239000004540 pour-on Substances 0.000 description 2
230000002335 preservative effect Effects 0.000 description 2
239000003380 propellant Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
229940080313 sodium starch Drugs 0.000 description 2
238000010183 spectrum analysis Methods 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
230000008719 thickening Effects 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
229960002622 triacetin Drugs 0.000 description 2
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
238000005550 wet granulation Methods 0.000 description 2
FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
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 1
102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
241000256118 Aedes aegypti Species 0.000 description 1
235000019489 Almond oil Nutrition 0.000 description 1
241001147657 Ancylostoma Species 0.000 description 1
241000254175 Anthonomus grandis Species 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
241000238421 Arthropoda Species 0.000 description 1
241000204727 Ascaridia Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
241000238657 Blattella germanica Species 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241000244036 Brugia Species 0.000 description 1
241000931178 Bunostomum Species 0.000 description 1
241000294063 Cacopsylla bidens Species 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000253350 Capillaria Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000359266 Chorioptes Species 0.000 description 1
241000207199 Citrus Species 0.000 description 1
241001126268 Cooperia Species 0.000 description 1
241000268912 Damalinia Species 0.000 description 1
241001128004 Demodex Species 0.000 description 1
241000202813 Dermatobia Species 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
241001147667 Dictyocaulus Species 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000243990 Dirofilaria Species 0.000 description 1
241001517923 Douglasiidae Species 0.000 description 1
235000003550 Dracunculus Nutrition 0.000 description 1
241000316827 Dracunculus <angiosperm> Species 0.000 description 1
239000001692 EU approved anti-caking agent Substances 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
241000282326 Felis catus Species 0.000 description 1
206010017533 Fungal infection Diseases 0.000 description 1
241001660203 Gasterophilus Species 0.000 description 1
241001442498 Globodera Species 0.000 description 1
241000790933 Haematopinus Species 0.000 description 1
241000243976 Haemonchus Species 0.000 description 1
241001480224 Heterodera Species 0.000 description 1
101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
241000257176 Hypoderma <fly> Species 0.000 description 1
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 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
241000257162 Lucilia <blowfly> Species 0.000 description 1
208000002720 Malnutrition Diseases 0.000 description 1
241000771995 Melophagus Species 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
241000721621 Myzus persicae 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
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
241000498271 Necator Species 0.000 description 1
241001137882 Nematodirus Species 0.000 description 1
241000514832 Neomyzus circumflexus Species 0.000 description 1
241000358422 Nephotettix cincticeps Species 0.000 description 1
241000510960 Oesophagostomum Species 0.000 description 1
241000243981 Onchocerca Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241000243795 Ostertagia Species 0.000 description 1
241001480755 Otobius Species 0.000 description 1
241000790250 Otodectes Species 0.000 description 1
241000904715 Oxyuris Species 0.000 description 1
241000244205 Panagrellus Species 0.000 description 1
241000488583 Panonychus ulmi Species 0.000 description 1
241000244187 Parascaris Species 0.000 description 1
208000030852 Parasitic disease Diseases 0.000 description 1
241000238661 Periplaneta Species 0.000 description 1
241001401863 Phorodon Species 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
241000500439 Plutella Species 0.000 description 1
241001016411 Psorergates Species 0.000 description 1
235000003534 Saccharomyces carlsbergensis Nutrition 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
101100381996 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) BRO1 gene Proteins 0.000 description 1
241001123227 Saccharomyces pastorianus Species 0.000 description 1
241000509416 Sarcoptes Species 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
241000258242 Siphonaptera Species 0.000 description 1
241000254179 Sitophilus granarius Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241000256248 Spodoptera Species 0.000 description 1
244000107946 Spondias cytherea Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241001494139 Stomoxys Species 0.000 description 1
241000244174 Strongyloides Species 0.000 description 1
241000122932 Strongylus Species 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
241000282887 Suidae Species 0.000 description 1
241000975704 Syphacia Species 0.000 description 1
241000255626 Tabanus <genus> Species 0.000 description 1
241001454294 Tetranychus Species 0.000 description 1
241000339374 Thrips tabaci Species 0.000 description 1
241000607216 Toxascaris Species 0.000 description 1
241000244031 Toxocara Species 0.000 description 1
241000254113 Tribolium castaneum Species 0.000 description 1
241000243797 Trichostrongylus Species 0.000 description 1
240000000359 Triticum dicoccon Species 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
241000222126 [Candida] glabrata Species 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000009471 action Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
229940063655 aluminum stearate Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
208000007502 anemia Diseases 0.000 description 1
239000012874 anionic emulsifier Substances 0.000 description 1
230000001178 anti-ectoparasitic effect Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000011805 ball Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000011449 brick Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
229940095672 calcium sulfate Drugs 0.000 description 1
ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
208000032343 candida glabrata infection Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229960001777 castor oil Drugs 0.000 description 1
239000007765 cera alba Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
238000007908 dry granulation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
244000079386 endoparasite Species 0.000 description 1
230000012173 estrus Effects 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000036541 health Effects 0.000 description 1
229940057306 hemihydrate calcium sulfate Drugs 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000003999 initiator Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
SSOVKTIUBYUZHC-UHFFFAOYSA-N lithium;tributoxyalumane Chemical compound [Li].CCCCO[Al](OCCCC)OCCCC SSOVKTIUBYUZHC-UHFFFAOYSA-N 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000001071 malnutrition Effects 0.000 description 1
235000000824 malnutrition Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000002483 medication Methods 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000003595 mist Substances 0.000 description 1
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
230000004899 motility Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012875 nonionic emulsifier Substances 0.000 description 1
208000015380 nutritional deficiency disease Diseases 0.000 description 1
229940041667 oral paste Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
235000015927 pasta Nutrition 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
244000144977 poultry Species 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
239000004576 sand Substances 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
229940032147 starch Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
208000016261 weight loss Diseases 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Tropical Medicine & Parasitology (AREA)
Public Health (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Saccharide Compounds (AREA)

DK505288A 1987-09-11 1988-09-09 Makrolidforbindelser, præparater indeholdende forbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne DK171255B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8721371		1987-09-11
GB878721371A GB8721371D0 (en)	1987-09-11	1987-09-11	Chemical compounds

Publications (3)

Publication Number	Publication Date
DK505288D0 DK505288D0 (da)	1988-09-09
DK505288A DK505288A (da)	1989-03-12
DK171255B1 true DK171255B1 (da)	1996-08-12

Family

ID=10623608

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK505288A DK171255B1 (da)	1987-09-11	1988-09-09	Makrolidforbindelser, præparater indeholdende forbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne

Country Status (13)

Country	Link
EP (1)	EP0307220A3 (de)
JP (1)	JPH01156980A (de)
KR (1)	KR960006389B1 (de)
AU (1)	AU622130B2 (de)
BR (1)	BR8804663A (de)
CA (1)	CA1340918C (de)
DD (1)	DD274623A5 (de)
DK (1)	DK171255B1 (de)
GB (1)	GB8721371D0 (de)
HU (1)	HU203240B (de)
NZ (1)	NZ226115A (de)
PT (1)	PT88461B (de)
ZA (1)	ZA886738B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ233680A (en) *	1989-05-17	1995-02-24	Beecham Group Plc	Avermectins and milbemycins and compositions thereof
JP4737616B2 (ja) *	2006-01-05	2011-08-03	日東電工株式会社	鑑識用粘着シート及びその製造方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0170006B1 (de) *	1984-06-05	1992-07-08	American Cyanamid Company	Wirkstoffe und deren Herstellungsverfahren, Verfahren und Zusamensetzungen, die diese Wirkstoffe enthalten zur Bekämpfung von helmintischen, arthropodischen, ectoparasitischen und acaridischen Infektionen
DE3785936T2 (de) *	1986-03-25	1993-08-26	Sankyo Co	Makrolid-derivate, ihre herstellung und ihre verwendung.
ZA872140B (en) *	1986-03-25	1988-11-30	Sankyo Co	Microlide compounds,their preparation and their use
NZ221077A (en) *	1986-07-18	1990-06-26	Ciba Geigy Ag	13b-alkyl milbemycins and use as parasiticides
US4806527A (en) *	1987-03-16	1989-02-21	Merck & Co., Inc.	Avermectin derivatives
GB8804440D0 (en) *	1988-02-25	1988-03-23	Pfizer Ltd	Antiparasitic agents
GB8811036D0 (en) *	1988-05-10	1988-06-15	Glaxo Group Ltd	Chemical compounds

1987
- 1987-09-11 GB GB878721371A patent/GB8721371D0/en active Pending
1988
- 1988-09-09 ZA ZA886738A patent/ZA886738B/xx unknown
- 1988-09-09 PT PT88461A patent/PT88461B/pt not_active IP Right Cessation
- 1988-09-09 CA CA000576932A patent/CA1340918C/en not_active Expired - Fee Related
- 1988-09-09 AU AU22086/88A patent/AU622130B2/en not_active Ceased
- 1988-09-09 BR BR8804663A patent/BR8804663A/pt not_active IP Right Cessation
- 1988-09-09 JP JP63224824A patent/JPH01156980A/ja active Pending
- 1988-09-09 DD DD88319670A patent/DD274623A5/de unknown
- 1988-09-09 HU HU884653A patent/HU203240B/hu not_active IP Right Cessation
- 1988-09-09 DK DK505288A patent/DK171255B1/da not_active IP Right Cessation
- 1988-09-09 NZ NZ226115A patent/NZ226115A/en unknown
- 1988-09-09 KR KR1019880011657A patent/KR960006389B1/ko not_active Expired - Fee Related
- 1988-09-09 EP EP19880308344 patent/EP0307220A3/de not_active Withdrawn

Also Published As

Publication number	Publication date
BR8804663A (pt)	1989-04-18
KR960006389B1 (ko)	1996-05-15
AU622130B2 (en)	1992-04-02
NZ226115A (en)	1991-06-25
PT88461B (pt)	1992-11-30
HUT48252A (en)	1989-05-29
DD274623A5 (de)	1989-12-27
CA1340918C (en)	2000-03-07
DK505288D0 (da)	1988-09-09
PT88461A (pt)	1988-10-01
HU203240B (en)	1991-06-28
ZA886738B (en)	1989-08-30
DK505288A (da)	1989-03-12
EP0307220A3 (de)	1990-10-31
EP0307220A2 (de)	1989-03-15
KR890005115A (ko)	1989-05-11
JPH01156980A (ja)	1989-06-20
GB8721371D0 (en)	1987-10-21
AU2208688A (en)	1989-03-16

Legal Events

Date	Code	Title	Description
1996-08-12	B1	Patent granted (law 1993)
2004-05-10	PBP	Patent lapsed	Country of ref document: DK

Publication	Publication Date	Title
DE3650265T2 (de)	1995-07-27	Makrolide Antibiotika und Verfahren zu deren Herstellung.
DK166498B1 (da)	1993-06-01	Macrolidforbindelser, fremgangsmaade til fremstilling deraf, praeparater indeholdende saadanne forbindelser samt en ikke-terapeutisk fremgangsmaade til bekaempelse af skadedyr under anvendelse af en saadan forbindelse
EP0238258B1 (de)	1994-01-26	Makrolid-Verbindungen
EP0241146B1 (de)	1993-02-03	Makrolid-Verbindungen
EP0237341B1 (de)	1993-09-22	Makrolid-Verbindungen
DK170344B1 (da)	1995-08-07	Makrolidforbindelser, farmaceutiske, veterinære og ikke-terapeutisk pesticide præparater indeholdende forbindelser, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
DK170859B1 (da)	1996-02-12	Makrolidforbindelser, præparater indeholdende forbindelserne til anvendelse i human medicin og veterinær medicin og til bekæmpelse af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
EP0231104B1 (de)	1992-09-09	Makrolid-Antibiotika und Verfahren zu ihrer Herstellung
DK171255B1 (da)	1996-08-12	Makrolidforbindelser, præparater indeholdende forbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
DK171063B1 (da)	1996-05-13	Makrolidforbindelser, præparater indeholdende makrolidforbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr, fremgangsmåde til fremstilling af forbindelserne samt fremgangsmåde til fremstilling af mellemprodukter
US4996228A (en)	1991-02-26	Macrolide antibiotics
US5336789A (en)	1994-08-09	Macrolide compounds
EP0307225B1 (de)	1994-08-24	Makrolid-Derivate
DK171025B1 (da)	1996-04-22	Makrolidforbindelser, farmaceutiske, veterinære og ikke-farmaceutiske pesticide præparater indeholdende forbindelserne, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige mider og fremgangsmåde til fremstilling af forbindelserne samt forbindelser til anvendelse ved fremstilling af makrolidforbindelserne
US5185456A (en)	1993-02-09	Macrolide compounds
US5192777A (en)	1993-03-09	Macrolide compounds
KR950010078B1 (ko)	1995-09-06	마크롤라이드 화합물
DE3781563T2 (de)	1993-01-07	Makrolid-antibiotika und verfahren zu ihrer herstellung.