BE565975A

BE565975A -

Info

Publication number: BE565975A
Authority: BE; Belgium
Prior art keywords: fluoro; chloro; esters; derivatives; cortisone
Prior art date

Application number

Other languages

English (en)

French (fr)

Publication of BE565975A publication Critical patent/BE565975A/fr

Links

JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 52
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 30
150000002148 esters Chemical class 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 20
239000000126 substance Substances 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
238000006356 dehydrogenation reaction Methods 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
150000001805 chlorine compounds Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229940000207 Selenious Acid Drugs 0.000 claims description 3
MCAHWIHFGHIESP-UHFFFAOYSA-N Selenous acid Chemical compound O[Se](O)=O MCAHWIHFGHIESP-UHFFFAOYSA-N 0.000 claims description 3
244000005700 microbiome Species 0.000 claims description 3
239000000186 progesterone Substances 0.000 claims description 3
241000223600 Alternaria Species 0.000 claims description 2
241000577959 Calonectria Species 0.000 claims description 2
MYYIMZRZXIQBGI-HVIRSNARSA-N Fluprednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C[C@H](F)C2=C1 MYYIMZRZXIQBGI-HVIRSNARSA-N 0.000 claims description 2
241000223218 Fusarium Species 0.000 claims description 2
241000427940 Fusarium solani Species 0.000 claims description 2
241000190509 Ophiobolus Species 0.000 claims description 2
241000203720 Pimelobacter simplex Species 0.000 claims description 2
MSXVEPNJUHWQHW-UHFFFAOYSA-N Tert-Amyl alcohol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
150000003509 tertiary alcohols Chemical class 0.000 claims description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N Cortisol Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims 2
229960000890 hydrocortisone Drugs 0.000 claims 2
BHDHELFREODRJK-XRYUJSLGSA-N (8S,9R,10S,13S,14S,17R)-9-fluoro-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound O=C1CC[C@]2(C)[C@@]3(F)C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 BHDHELFREODRJK-XRYUJSLGSA-N 0.000 claims 1
RYTFNVIZBLCIMZ-WMSSUOLPSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-16-chloro-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(Cl)[C@H](C(=O)C)[C@@]1(C)CC2 RYTFNVIZBLCIMZ-WMSSUOLPSA-N 0.000 claims 1
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims 1
241000555695 Didymella Species 0.000 claims 1
229960004544 cortisone Drugs 0.000 claims 1
150000007530 organic bases Chemical group 0.000 claims 1
150000003124 pregnadienes Chemical class 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
239000000203 mixture Substances 0.000 description 71
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
239000000243 solution Substances 0.000 description 47
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000002244 precipitate Substances 0.000 description 22
239000002253 acid Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000012299 nitrogen atmosphere Substances 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
239000000706 filtrate Substances 0.000 description 15
229910052938 sodium sulfate Inorganic materials 0.000 description 15
235000011152 sodium sulphate Nutrition 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000008079 hexane Substances 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
229960000583 Acetic Acid Drugs 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
235000011054 acetic acid Nutrition 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
150000007513 acids Chemical class 0.000 description 8
WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 8
238000005406 washing Methods 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000005457 ice water Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
238000010828 elution Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
125000004432 carbon atoms Chemical group C* 0.000 description 5
230000000875 corresponding Effects 0.000 description 5
KRHYYFGTRYWZRS-UHFFFAOYSA-N HF Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
229940117975 chromium trioxide Drugs 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000005712 crystallization Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
-1 heterocyclic dicarboxylic acids Chemical class 0.000 description 4
229960005205 prednisolone Drugs 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000012265 solid product Substances 0.000 description 4
VUVGYHUDAICLFK-UHFFFAOYSA-N Perosmic oxide Chemical compound O=[Os](=O)(=O)=O VUVGYHUDAICLFK-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
OIGNJSKKLXVSLS-VWUMJDOOSA-N Prednisolone Chemical class O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
230000001264 neutralization Effects 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
150000003343 selenium compounds Chemical class 0.000 description 3
239000001187 sodium carbonate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003643 water by type Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N Pelargonic acid Natural products CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
229960004618 prednisone Drugs 0.000 description 2
150000003118 prednisones Chemical class 0.000 description 2
150000004672 propanoic acids Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
229940065287 selenium compounds Drugs 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
BHTWZQKERRCPRZ-RYRKJORJSA-N (8S,13S,14S)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione Chemical class C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)(C(CC3)=O)CC3)C3=C21 BHTWZQKERRCPRZ-RYRKJORJSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
239000005631 2,4-D Substances 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-Dichlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
BUSOTUQRURCMCM-UHFFFAOYSA-N 3-Phenoxypropionic acid Chemical compound OC(=O)CCOC1=CC=CC=C1 BUSOTUQRURCMCM-UHFFFAOYSA-N 0.000 description 1
HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
SODPIMGUZLOIPE-UHFFFAOYSA-N 4-Chlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
YKYVPFIBWVQZCE-UHFFFAOYSA-N 4-phenoxybutanoic acid Chemical compound OC(=O)CCCOC1=CC=CC=C1 YKYVPFIBWVQZCE-UHFFFAOYSA-N 0.000 description 1
YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 description 1
UZROOFLUFHWOJQ-ADDDSGAWSA-N 6α-Fluoropregn-4-ene-3,20-dione Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 UZROOFLUFHWOJQ-ADDDSGAWSA-N 0.000 description 1
241000487074 Alosa alosa Species 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
229940064005 Antibiotic throat preparations Drugs 0.000 description 1
229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 1
229940042052 Antibiotics for systemic use Drugs 0.000 description 1
229940042786 Antitubercular Antibiotics Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
241001273385 Boeremia lycopersici Species 0.000 description 1
229940041514 Candida albicans extract Drugs 0.000 description 1
229940064701 Corticosteroid nasal preparations for topical use Drugs 0.000 description 1
229960001334 Corticosteroids Drugs 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N Cypionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
229940093922 Gynecological Antibiotics Drugs 0.000 description 1
210000004185 Liver Anatomy 0.000 description 1
235000021360 Myristic acid Nutrition 0.000 description 1
VBTQNRFWXBXZQR-UHFFFAOYSA-N N-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N Phenylpropanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N Pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene (PE) Substances 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N Prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
RJKFOVLPORLFTN-STHVQZNPSA-N Progesterone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC(=O)CC4)CC3)CC2)CC1 RJKFOVLPORLFTN-STHVQZNPSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
206010041277 Sodium retention Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 1
FRPZMMHWLSIFAZ-UHFFFAOYSA-N Undecylenic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
238000007792 addition Methods 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
230000003115 biocidal Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
235000005824 corn Nutrition 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000002592 echocardiography Methods 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable Effects 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002311 glutaric acids Chemical class 0.000 description 1
230000002394 glycogenic Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229940079866 intestinal antibiotics Drugs 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000002906 microbiologic Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229940005935 ophthalmologic Antibiotics Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002943 palmitic acids Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
150000003117 prednisolones Chemical class 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
229960003387 progesterone Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
231100000486 side effect Toxicity 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229940001607 sodium bisulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
230000002522 swelling Effects 0.000 description 1
229940083878 topical for treatment of hemorrhoids and anal fissures Corticosteroids Drugs 0.000 description 1
230000001131 transforming Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229960002703 undecylenic acid Drugs 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1