HUP0201592A2 - Cyclo-imino depsipeptides and their utilization in controlling endoparasites - Google Patents

Info

Publication number

HUP0201592A2

HUP0201592A2 HU0201592A HUP0201592A HUP0201592A2 HU P0201592 A2 HUP0201592 A2 HU P0201592A2 HU 0201592 A HU0201592 A HU 0201592A HU P0201592 A HUP0201592 A HU P0201592A HU P0201592 A2 HUP0201592 A2 HU P0201592A2

Authority

HU

Hungary

Prior art keywords

group

alkyl

formula

optionally substituted

general formula

Prior art date

1999-06-11

Links

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• 244000079386 endoparasite Species 0.000 title claims description 15
• 108010002156 Depsipeptides Proteins 0.000 title description 13
• -1 cyano, nitrocarbamoyl Chemical group 0.000 claims description 311
• 150000001875 compounds Chemical class 0.000 claims description 102
• 238000000034 method Methods 0.000 claims description 97
• 239000000203 mixture Substances 0.000 claims description 81
• 230000008569 process Effects 0.000 claims description 80
• 125000000217 alkyl group Chemical group 0.000 claims description 64
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
• 238000006243 chemical reaction Methods 0.000 claims description 56
• 238000002360 preparation method Methods 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 56
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 40
• 239000003085 diluting agent Substances 0.000 claims description 37
• 125000004432 carbon atom Chemical group C* 0.000 claims description 34
• 125000001072 heteroaryl group Chemical group 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 29
• 125000004122 cyclic group Chemical group 0.000 claims description 29
• 239000003054 catalyst Substances 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
• 229910052760 oxygen Inorganic materials 0.000 claims description 25
• 125000006239 protecting group Chemical group 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 125000003277 amino group Chemical group 0.000 claims description 22
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 19
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 16
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
• 239000011593 sulfur Substances 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• 239000003153 chemical reaction reagent Substances 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 229920000642 polymer Polymers 0.000 claims description 14
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
• BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 238000005984 hydrogenation reaction Methods 0.000 claims description 11
• 229910052751 metal Inorganic materials 0.000 claims description 11
• 239000002184 metal Substances 0.000 claims description 11
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
• 230000008878 coupling Effects 0.000 claims description 10
• 238000010168 coupling process Methods 0.000 claims description 10
• 238000005859 coupling reaction Methods 0.000 claims description 10
• 125000004962 sulfoxyl group Chemical group 0.000 claims description 10
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 9
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
• 125000004434 sulfur atom Chemical group 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 8
• UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 8
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 7
• 229910044991 metal oxide Inorganic materials 0.000 claims description 7
• 150000004706 metal oxides Chemical class 0.000 claims description 7
• 230000003287 optical effect Effects 0.000 claims description 7
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 7
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 6
• 125000004104 aryloxy group Chemical group 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000003107 substituted aryl group Chemical group 0.000 claims description 5
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
• 125000005108 alkenylthio group Chemical group 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000005109 alkynylthio group Chemical group 0.000 claims description 4
• 125000001769 aryl amino group Chemical group 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 239000000969 carrier Substances 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 4
• 150000002829 nitrogen Chemical class 0.000 claims description 4
• 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
• VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 3
• 150000003862 amino acid derivatives Chemical class 0.000 claims description 3
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
• 125000006799 (C2-C6) alkenylamino group Chemical group 0.000 claims description 2
• 125000006802 (C2-C6) alkynylamino group Chemical group 0.000 claims description 2
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 2
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 2
• 125000005367 heteroarylalkylthio group Chemical group 0.000 claims description 2
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 2
• 239000004094 surface-active agent Substances 0.000 claims description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
• 235000002639 sodium chloride Nutrition 0.000 description 45
• 239000004480 active ingredient Substances 0.000 description 31
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
• 239000000243 solution Substances 0.000 description 29
• 230000002378 acidificating effect Effects 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 19
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• 239000002585 base Substances 0.000 description 16
• 239000007858 starting material Substances 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
• 239000012043 crude product Substances 0.000 description 13
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 239000002245 particle Substances 0.000 description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• 238000004128 high performance liquid chromatography Methods 0.000 description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 241001465754 Metazoa Species 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• 229940024606 amino acid Drugs 0.000 description 9
• 150000001413 amino acids Chemical class 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• 239000000546 pharmaceutical excipient Substances 0.000 description 9
• 229920005990 polystyrene resin Polymers 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
• 235000014113 dietary fatty acids Nutrition 0.000 description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 239000000194 fatty acid Substances 0.000 description 8
• 229930195729 fatty acid Natural products 0.000 description 8
• 238000002347 injection Methods 0.000 description 8
• 239000007924 injection Substances 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 7
• 229910052801 chlorine Inorganic materials 0.000 description 7
• 239000010949 copper Substances 0.000 description 7
• 229910052802 copper Inorganic materials 0.000 description 7
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• 239000011737 fluorine Substances 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 229910052763 palladium Inorganic materials 0.000 description 7
• 108090000765 processed proteins & peptides Proteins 0.000 description 7
• 150000003512 tertiary amines Chemical class 0.000 description 7
• XJODGRWDFZVTKW-LURJTMIESA-N (2s)-4-methyl-2-(methylamino)pentanoic acid Chemical compound CN[C@H](C(O)=O)CC(C)C XJODGRWDFZVTKW-LURJTMIESA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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• 150000007513 acids Chemical class 0.000 description 6
• 239000003963 antioxidant agent Substances 0.000 description 6
• 235000006708 antioxidants Nutrition 0.000 description 6
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• WRWHFVRDUAQRIQ-UHFFFAOYSA-N carbonothioic O,O-acid Chemical class OC(O)=S WRWHFVRDUAQRIQ-UHFFFAOYSA-N 0.000 description 6
• 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 125000001309 chloro group Chemical group Cl* 0.000 description 6
• 235000013601 eggs Nutrition 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
• 125000005842 heteroatom Chemical group 0.000 description 6
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• 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
• 239000002562 thickening agent Substances 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
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• 241000699670 Mus sp. Species 0.000 description 5
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
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• 108010004210 PF 1022A Proteins 0.000 description 5
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• 238000003776 cleavage reaction Methods 0.000 description 5
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• 150000004665 fatty acids Chemical class 0.000 description 5
• 150000008282 halocarbons Chemical class 0.000 description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 description 5
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• 235000019198 oils Nutrition 0.000 description 5
• 244000045947 parasite Species 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000003755 preservative agent Substances 0.000 description 5
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 230000035484 reaction time Effects 0.000 description 5
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• 125000006413 ring segment Chemical group 0.000 description 5
• 230000007017 scission Effects 0.000 description 5
• QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
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