NO324287B1 - Substituerte marcfortiner og paraherkvamider, fremgangsmater for deres fremstilling og anvendelse derav for fremstilling av antiparasittiske midler. - Google Patents

Substituerte marcfortiner og paraherkvamider, fremgangsmater for deres fremstilling og anvendelse derav for fremstilling av antiparasittiske midler. Download PDF

Info

Publication number: NO324287B1
Authority: NO; Norway
Prior art keywords: hydroxy; formula; compound; alkyl; compounds
Prior art date: 1995-07-21

Application number

NO19980255A

Other languages

English (en)

Norwegian (no)

Other versions

NO980255L (no

NO980255D0 (no

Inventor

Byung H Lee

Michael F Clothier

Original Assignee

Pharmacia & Upjohn Co Llc

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.)

1995-07-21

Filing date

1998-01-20

Publication date

2007-09-17

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=21695455&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO324287(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-01-20 Application filed by Pharmacia & Upjohn Co Llc filed Critical Pharmacia & Upjohn Co Llc

1998-01-20 Publication of NO980255D0 publication Critical patent/NO980255D0/no

1998-03-20 Publication of NO980255L publication Critical patent/NO980255L/no

2007-09-17 Publication of NO324287B1 publication Critical patent/NO324287B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 48
239000003096 antiparasitic agent Substances 0.000 title claims description 40
229940125687 antiparasitic agent Drugs 0.000 title claims description 8
238000000034 method Methods 0.000 title description 59
229930188716 paraherquamide Natural products 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims description 154
239000000203 mixture Substances 0.000 claims description 114
229910052799 carbon Inorganic materials 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 26
150000001204 N-oxides Chemical class 0.000 claims description 19
239000012279 sodium borohydride Substances 0.000 claims description 16
229910000033 sodium borohydride Inorganic materials 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 14
244000045947 parasite Species 0.000 claims description 14
UVZZDDLIOJPDKX-UHFFFAOYSA-N paraherquamide A Natural products O1C(C)(C)C=COC2=C1C=CC1=C2NC(=O)C11C(C)(C)C2CC3(N(C4)CCC3(C)O)C(=O)N(C)C42C1 UVZZDDLIOJPDKX-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
244000078703 ectoparasite Species 0.000 claims description 8
150000002222 fluorine compounds Chemical class 0.000 claims description 8
241000238421 Arthropoda Species 0.000 claims description 4
244000000013 helminth Species 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
JPDNNPOSGMWCHG-NNSXXJBVSA-N chembl2252930 Chemical class O1C(C)(C)C=COC2=C1C=CC1=C2NC(=O)[C@@]1(C(C)(C)[C@@H]1C2)C[C@]31CN1CCC[C@]12C(=O)N3C JPDNNPOSGMWCHG-NNSXXJBVSA-N 0.000 claims description 3
230000007306 turnover Effects 0.000 claims 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 230
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 147
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 130
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 93
238000005481 NMR spectroscopy Methods 0.000 description 77
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 65
239000000243 solution Substances 0.000 description 58
238000006243 chemical reaction Methods 0.000 description 50
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
239000000741 silica gel Substances 0.000 description 38
229910002027 silica gel Inorganic materials 0.000 description 38
125000001424 substituent group Chemical group 0.000 description 32
230000002141 anti-parasite Effects 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 31
235000019439 ethyl acetate Nutrition 0.000 description 28
239000007787 solid Substances 0.000 description 26
239000000047 product Substances 0.000 description 25
229910052943 magnesium sulfate Inorganic materials 0.000 description 24
235000019341 magnesium sulphate Nutrition 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
238000004949 mass spectrometry Methods 0.000 description 22
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
238000010898 silica gel chromatography Methods 0.000 description 22
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
238000000855 fermentation Methods 0.000 description 21
230000004151 fermentation Effects 0.000 description 21
239000002904 solvent Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
241001465754 Metazoa Species 0.000 description 20
239000002609 medium Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000284 extract Substances 0.000 description 18
-1 lithium aluminum hydride Chemical compound 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
150000001721 carbon Chemical group 0.000 description 15
239000012141 concentrate Substances 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
238000009472 formulation Methods 0.000 description 14
150000003949 imides Chemical class 0.000 description 13
208000015181 infectious disease Diseases 0.000 description 13
239000013587 production medium Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
UVZZDDLIOJPDKX-ITKQZBBDSA-N paraherquamide Chemical class O1C(C)(C)C=COC2=C1C=CC1=C2NC(=O)[C@]11C(C)(C)[C@@H]2C[C@]3(N(C4)CC[C@@]3(C)O)C(=O)N(C)[C@]42C1 UVZZDDLIOJPDKX-ITKQZBBDSA-N 0.000 description 12
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 12
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
239000002054 inoculum Substances 0.000 description 10
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 9
238000012746 preparative thin layer chromatography Methods 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000011734 sodium Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
229930188848 Marcfortine Natural products 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
201000010099 disease Diseases 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
239000012280 lithium aluminium hydride Substances 0.000 description 7
239000000463 material Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000007858 starting material Substances 0.000 description 7
241000238876 Acari Species 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
208000030852 Parasitic disease Diseases 0.000 description 6
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000008280 blood Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
235000012343 cottonseed oil Nutrition 0.000 description 6
230000035784 germination Effects 0.000 description 6
229960001031 glucose Drugs 0.000 description 6
239000010410 layer Substances 0.000 description 6
235000012054 meals Nutrition 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
238000003756 stirring Methods 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
241000228168 Penicillium sp. Species 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
241000607479 Yersinia pestis Species 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
239000008103 glucose Substances 0.000 description 5
238000002955 isolation Methods 0.000 description 5
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 5
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
239000011343 solid material Substances 0.000 description 5
241000894007 species Species 0.000 description 5
239000008399 tap water Substances 0.000 description 5
235000020679 tap water Nutrition 0.000 description 5
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
208000006968 Helminthiasis Diseases 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000008272 agar Substances 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000002518 antifoaming agent Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000000969 carrier Substances 0.000 description 4
244000079386 endoparasite Species 0.000 description 4
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 4
238000003306 harvesting Methods 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 4
239000012071 phase Substances 0.000 description 4
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 4
229910000105 potassium hydride Inorganic materials 0.000 description 4
235000018102 proteins Nutrition 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
238000001223 reverse osmosis Methods 0.000 description 4
239000002002 slurry Substances 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical group [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
241000283086 Equidae Species 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
238000003747 Grignard reaction Methods 0.000 description 3
241000238631 Hexapoda Species 0.000 description 3
241001494479 Pecora Species 0.000 description 3
241001674048 Phthiraptera Species 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
238000006859 Swern oxidation reaction Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000000306 component Substances 0.000 description 3
229940043279 diisopropylamine Drugs 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012634 fragment Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000011630 iodine Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000012533 medium component Substances 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012285 osmium tetroxide Substances 0.000 description 3
229910000489 osmium tetroxide Inorganic materials 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
WJCXADMLESSGRI-UHFFFAOYSA-N phenyl selenohypochlorite Chemical compound Cl[Se]C1=CC=CC=C1 WJCXADMLESSGRI-UHFFFAOYSA-N 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
230000002265 prevention Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000011218 seed culture Methods 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
MKHGVMIXRPGHOO-UHFFFAOYSA-N 2-(benzenesulfonyl)-3-phenyloxaziridine Chemical compound C=1C=CC=CC=1S(=O)(=O)N1OC1C1=CC=CC=C1 MKHGVMIXRPGHOO-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
IZZYABADQVQHLC-UHFFFAOYSA-N 4-methylbenzenesulfonyl fluoride Chemical compound CC1=CC=C(S(F)(=O)=O)C=C1 IZZYABADQVQHLC-UHFFFAOYSA-N 0.000 description 2
241001147657 Ancylostoma Species 0.000 description 2
241000244186 Ascaris Species 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
241000253350 Capillaria Species 0.000 description 2
241000283707 Capra Species 0.000 description 2
229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 2
241001126268 Cooperia Species 0.000 description 2
229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
241000243976 Haemonchus Species 0.000 description 2
239000012448 Lithium borohydride Substances 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
241001137882 Nematodirus Species 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
241000243795 Ostertagia Species 0.000 description 2
241000985548 Penicillium charlesii Species 0.000 description 2
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Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Tropical Medicine & Parasitology (AREA)
Public Health (AREA)
Agronomy & Crop Science (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Percussion Or Vibration Massage (AREA)
Epoxy Compounds (AREA)

NO19980255A 1995-07-21 1998-01-20 Substituerte marcfortiner og paraherkvamider, fremgangsmater for deres fremstilling og anvendelse derav for fremstilling av antiparasittiske midler. NO324287B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US132495P	1995-07-21	1995-07-21
PCT/US1996/010686 WO1997003988A1 (en)	1995-07-21	1996-06-26	Antiparasitic marcfortines and paraherquamides

Publications (3)

Publication Number	Publication Date
NO980255D0 NO980255D0 (no)	1998-01-20
NO980255L NO980255L (no)	1998-03-20
NO324287B1 true NO324287B1 (no)	2007-09-17

Family

ID=21695455

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19980255A NO324287B1 (no)	1995-07-21	1998-01-20	Substituerte marcfortiner og paraherkvamider, fremgangsmater for deres fremstilling og anvendelse derav for fremstilling av antiparasittiske midler.

Country Status (30)

Country	Link
US (2)	US5703078A (cs)
EP (3)	EP0871631B1 (cs)
JP (2)	JP4122447B2 (cs)
KR (1)	KR100428335B1 (cs)
CN (2)	CN1277830C (cs)
AR (10)	AR003466A1 (cs)
AT (1)	ATE311390T1 (cs)
AU (1)	AU699644B2 (cs)
BR (7)	BR9612963B8 (cs)
CA (1)	CA2225813C (cs)
CO (1)	CO4750664A1 (cs)
CZ (1)	CZ296008B6 (cs)
DE (1)	DE69635524T2 (cs)
DK (2)	DK0871631T3 (cs)
ES (2)	ES2249783T3 (cs)
FI (2)	FI115912B (cs)
HU (1)	HU226296B1 (cs)
ID (1)	ID30373A (cs)
MX (1)	MX9800625A (cs)
MY (1)	MY113806A (cs)
NO (1)	NO324287B1 (cs)
NZ (1)	NZ311952A (cs)
PL (1)	PL185007B1 (cs)
PT (1)	PT1489082E (cs)
RU (1)	RU2162090C2 (cs)
SI (1)	SI0871631T1 (cs)
SK (2)	SK285248B6 (cs)
TW (1)	TW334436B (cs)
WO (1)	WO1997003988A1 (cs)
ZA (1)	ZA965908B (cs)

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AP2014007874A0 (en)	2012-02-06	2014-08-31	Merial Ltd	Parasiticidal oral veterinary compositions comprising systemetically- acting active agents, methods and uses thereof
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CA2870956C (en)	2012-04-20	2020-03-31	Merial Limited	Parasiticidal compositions comprising benzimidazole derivatives, methods and uses thereof
JP5737255B2 (ja) *	2012-09-27	2015-06-17	ダイキン工業株式会社	チオノカルボン酸エステルの製造方法
NZ716598A (en)	2012-11-20	2017-02-24	Merial Inc	Anthelmintic compounds and compositions and method of using thereof
WO2015066277A1 (en)	2013-11-01	2015-05-07	Merial Limited	Antiparisitic and pesticidal isoxazoline compounds
JP6682719B2 (ja)	2014-04-17	2020-04-15	ベーリンガーインゲルハイムアニマルヘルスユーエスエイインコーポレイテッド	寄生生物から動物を保護するためのマロノニトリル化合物の使用
NZ726874A (en)	2014-05-19	2018-03-23	Merial Inc	Anthelmintic compounds
ES2723969T3 (es)	2014-06-19	2019-09-04	Merial Inc	Composiciones parasiticidas que comprenden derivados de indol, procedimientos y usos de las mismas
AU2015339096B2 (en)	2014-10-31	2018-08-02	Boehringer Ingelheim Animal Health USA Inc.	Parasiticidal composition comprising fipronil
UY36570A (es)	2015-02-26	2016-10-31	Merial Inc	Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas
RS62130B1 (sr)	2015-05-20	2021-08-31	Boehringer Ingelheim Animal Health Usa Inc	Antihelmintička depsipeptidna jedinjenja
UY37137A (es)	2016-02-24	2017-09-29	Merial Inc	Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos
WO2018039508A1 (en)	2016-08-25	2018-03-01	Merial, Inc.	Method for reducing unwanted effects in parasiticidal treatments
JP2019535655A (ja)	2016-10-14	2019-12-12	ベーリンガーインゲルハイムアニマルヘルスユーエスエイインコーポレイテッド	殺虫性及び殺寄生虫性ビニルイソオキサゾリン化合物
BR112019009977A2 (pt)	2016-11-16	2019-08-27	Boehringer Ingelheim Animal Health Usa Inc	compostos depsipeptídicos anti-helmínticos
MX2020001724A (es)	2017-08-14	2020-07-29	Boehringer Ingelheim Animal Health Usa Inc	Compuestos de pirazol-isoxazolina plaguicidas y parasiticidas.
US11583545B2 (en)	2018-02-08	2023-02-21	Boehringer Ingelheim Animal Health USA Inc.	Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof
MX2021000293A (es)	2018-07-09	2021-07-15	Boehringer Ingelheim Animal Health Usa Inc	Compuestos heterociclicos antihelminticos.
US11773066B2 (en)	2018-11-20	2023-10-03	Boehringer Ingelheim Animal Health USA Inc.	Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof
AU2020231319A1 (en)	2019-03-01	2021-10-21	Boehringer Ingelheim Animal Health USA Inc.	Injectable clorsulon compositions, methods and uses thereof
KR20220002890A (ko)	2019-03-19	2022-01-07	뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드	구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물
BR112022024156A2 (pt)	2020-05-29	2023-02-14	Boehringer Ingelheim Animal Health Usa Inc	Compostos heterocílicos antelmínticos
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1996
- 1996-06-04 MY MYPI96002158A patent/MY113806A/en unknown
- 1996-06-04 TW TW085106656A patent/TW334436B/zh not_active IP Right Cessation
- 1996-06-26 BR BRPI9612963-8B8A patent/BR9612963B8/pt not_active IP Right Cessation
- 1996-06-26 PT PT40226383T patent/PT1489082E/pt unknown
- 1996-06-26 KR KR10-1998-0700418A patent/KR100428335B1/ko not_active Expired - Fee Related
- 1996-06-26 SK SK5057-2005A patent/SK285248B6/sk not_active IP Right Cessation
- 1996-06-26 DK DK96922529T patent/DK0871631T3/da active
- 1996-06-26 SI SI9630723T patent/SI0871631T1/sl unknown
- 1996-06-26 ES ES96922529T patent/ES2249783T3/es not_active Expired - Lifetime
- 1996-06-26 EP EP96922529A patent/EP0871631B1/en not_active Expired - Lifetime
- 1996-06-26 BR BRPI9612975-1B8A patent/BR9612975B8/pt not_active IP Right Cessation
- 1996-06-26 WO PCT/US1996/010686 patent/WO1997003988A1/en not_active Ceased
- 1996-06-26 AU AU63373/96A patent/AU699644B2/en not_active Expired
- 1996-06-26 BR BRPI9612974-3B8A patent/BR9612974B8/pt not_active IP Right Cessation
- 1996-06-26 DE DE69635524T patent/DE69635524T2/de not_active Expired - Lifetime
- 1996-06-26 NZ NZ311952A patent/NZ311952A/xx not_active IP Right Cessation
- 1996-06-26 MX MX9800625A patent/MX9800625A/es unknown
- 1996-06-26 BR BRPI9612973-5B8A patent/BR9612973B8/pt not_active IP Right Cessation
- 1996-06-26 JP JP50667697A patent/JP4122447B2/ja not_active Expired - Fee Related
- 1996-06-26 ES ES04022638.3T patent/ES2439569T3/es not_active Expired - Lifetime
- 1996-06-26 DK DK04022638.3T patent/DK1489082T3/da active
- 1996-06-26 BR BRPI9612972-7B8A patent/BR9612972B8/pt not_active IP Right Cessation
- 1996-06-26 CA CA002225813A patent/CA2225813C/en not_active Expired - Lifetime
- 1996-06-26 BR BRPI9612944-1B8A patent/BR9612944B8/pt not_active IP Right Cessation
- 1996-06-26 SK SK54-98A patent/SK284833B6/sk not_active IP Right Cessation
- 1996-06-26 CZ CZ1998110A patent/CZ296008B6/cs not_active IP Right Cessation
- 1996-06-26 CN CNB03158991XA patent/CN1277830C/zh not_active Expired - Lifetime
- 1996-06-26 EP EP03023859A patent/EP1400523A3/en not_active Withdrawn
- 1996-06-26 EP EP04022638.3A patent/EP1489082B1/en not_active Expired - Lifetime
- 1996-06-26 AT AT96922529T patent/ATE311390T1/de active
- 1996-06-26 RU RU98103337/04A patent/RU2162090C2/ru active
- 1996-06-26 BR BRPI9609812-0B8A patent/BR9609812B8/pt not_active IP Right Cessation
- 1996-06-26 CN CN96195723A patent/CN1125824C/zh not_active Expired - Fee Related
- 1996-06-26 PL PL96324574A patent/PL185007B1/pl unknown
- 1996-06-26 HU HU9802221A patent/HU226296B1/hu not_active IP Right Cessation
- 1996-06-27 US US08/670,306 patent/US5703078A/en not_active Expired - Lifetime
- 1996-07-11 ZA ZA9605908A patent/ZA965908B/xx unknown
- 1996-07-19 CO CO96038153A patent/CO4750664A1/es unknown
- 1996-07-19 AR ARP960103674A patent/AR003466A1/es active IP Right Grant
- 1996-07-22 ID IDP00200100831A patent/ID30373A/id unknown
1997
- 1997-03-21 US US08/822,419 patent/US5750695A/en not_active Expired - Lifetime
1998
- 1998-01-20 FI FI980112A patent/FI115912B/fi not_active IP Right Cessation
- 1998-01-20 NO NO19980255A patent/NO324287B1/no not_active IP Right Cessation
2003
- 2003-02-13 AR ARP030100481A patent/AR038427A2/es active IP Right Grant
- 2003-02-13 AR ARP030100487A patent/AR038433A2/es active IP Right Grant
- 2003-02-13 AR ARP030100483A patent/AR038429A2/es active IP Right Grant
- 2003-02-13 AR ARP030100485A patent/AR038431A2/es active IP Right Grant
- 2003-02-13 AR ARP030100486A patent/AR038432A2/es active IP Right Grant
- 2003-02-13 AR ARP030100482A patent/AR038428A2/es active IP Right Grant
- 2003-02-13 AR ARP030100488A patent/AR038434A2/es active IP Right Grant
- 2003-02-13 AR ARP030100484A patent/AR038430A2/es active IP Right Grant
2005
- 2005-03-04 FI FI20050238A patent/FI118471B/fi not_active IP Right Cessation
2006
- 2006-02-10 AR ARP060100487A patent/AR052907A1/es not_active Application Discontinuation
2007
- 2007-08-22 JP JP2007216098A patent/JP2008007516A/ja active Pending

Also Published As

Publication number	Publication date
NZ311952A (en)	1999-03-29
FI118471B (fi)	2007-11-30
AR038427A2 (es)	2005-01-12
SI0871631T1 (sl)	2006-04-30
CZ296008B6 (cs)	2005-12-14
EP1400523A2 (en)	2004-03-24
HUP9802221A2 (hu)	1999-02-01
JPH11509550A (ja)	1999-08-24
US5750695A (en)	1998-05-12
BR9612944B8 (pt)	2014-10-29
ZA965908B (en)	1997-01-12
MY113806A (en)	2002-05-31
AR038428A2 (es)	2005-01-12
BR9612974B8 (pt)	2014-10-29
AR038433A2 (es)	2005-01-12
CA2225813A1 (en)	1997-02-06
SK284833B6 (sk)	2005-12-01
AU6337396A (en)	1997-02-18
EP1489082B1 (en)	2013-11-20
NO980255L (no)	1998-03-20
HK1061242A1 (en)	2004-09-10
SK285248B6 (sk)	2006-09-07
ES2249783T3 (es)	2006-04-01
DE69635524D1 (de)	2006-01-05
FI980112L (fi)	1998-01-20
WO1997003988A1 (en)	1997-02-06
BR9612963B8 (pt)	2014-10-29
PL185007B1 (pl)	2003-01-31
AR052907A1 (es)	2007-04-11
FI115912B (fi)	2005-08-15
PT1489082E (pt)	2013-12-23
PL324574A1 (en)	1998-06-08
EP0871631B1 (en)	2005-11-30
NO980255D0 (no)	1998-01-20
BR9612973B8 (pt)	2014-10-29
HK1017883A1 (en)	1999-12-03
BR9612972B8 (pt)	2014-10-29
FI20050238L (fi)	2005-03-04
ID30373A (id)	1997-01-23
BR9609812B8 (pt)	2014-10-29
AR038434A2 (es)	2005-01-12
BR9609812A (pt)	1999-03-02
CN1191537A (zh)	1998-08-26
US5703078A (en)	1997-12-30
RU2162090C2 (ru)	2001-01-20
DK1489082T3 (da)	2013-12-09
MX9800625A (es)	1998-04-30
BR9612975B8 (pt)	2014-10-29
ES2439569T3 (es)	2014-01-23
EP1400523A3 (en)	2004-04-07
CN1125824C (zh)	2003-10-29
TW334436B (en)	1998-06-21
EP1489082A1 (en)	2004-12-22
CO4750664A1 (es)	1999-03-31
HU226296B1 (hu)	2008-08-28
AR038432A2 (es)	2005-01-12
SK5498A3 (en)	1998-08-05
CN1495183A (zh)	2004-05-12
KR100428335B1 (ko)	2004-06-16
FI980112A0 (fi)	1998-01-20
AR038429A2 (es)	2005-01-12
CA2225813C (en)	2008-02-26
HUP9802221A3 (en)	2000-05-29
AR038430A2 (es)	2005-01-12
JP4122447B2 (ja)	2008-07-23
AU699644B2 (en)	1998-12-10
JP2008007516A (ja)	2008-01-17
AR038431A2 (es)	2005-01-12
CN1277830C (zh)	2006-10-04
CZ11098A3 (cs)	1998-06-17
ATE311390T1 (de)	2005-12-15
EP0871631A1 (en)	1998-10-21
DE69635524T2 (de)	2006-07-06
DK0871631T3 (da)	2006-03-13
AR003466A1 (es)	1998-08-05

Legal Events

Date	Code	Title	Description
2013-05-21	CHAD	Change of the owner's name or address (par. 44 patent law, par. patentforskriften)	Owner name: ZOETIS P&U LLC, US
2016-07-04	MK1K	Patent expired