PT97503A

PT97503A - Processo para a preparacao de derivados eter de butirolactol

Processo para a preparacao de derivados eter de butirolactol Download PDF

Info

Publication number: PT97503A
Authority: PT; Portugal
Prior art keywords: general structure; formula; quot; pyridyl; compound
Prior art date: 1990-04-27

Application number

PT97503A

Other languages

English (en)

Portuguese (pt)

Inventor

Alan H Davidson

Mark Whittaker

Zoe Marie Spavold

Stephen Arthur Bowles

Original Assignee

British Bio Technology

Priority date

1990-04-27

Filing date

1991-04-26

Publication date

1992-01-31

1991-04-26 Application filed by British Bio Technology filed Critical British Bio Technology

1992-01-31 Publication of PT97503A publication Critical patent/PT97503A/pt

Links

238000000034 method Methods 0.000 title claims description 90
230000008569 process Effects 0.000 title claims description 25
238000002360 preparation method Methods 0.000 title claims description 19
125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims description 115
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 113
-1 phenylene, furanediyl Chemical group 0.000 claims description 107
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 63
239000000203 mixture Substances 0.000 claims description 62
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 59
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 57
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 39
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
238000011282 treatment Methods 0.000 claims description 25
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 22
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004076 pyridyl group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
150000002596 lactones Chemical class 0.000 claims description 10
239000000843 powder Substances 0.000 claims description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 9
238000009472 formulation Methods 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000001246 bromo group Chemical group Br* 0.000 claims description 8
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 8
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
230000009467 reduction Effects 0.000 claims description 7
229930184458 Butyrolactol Natural products 0.000 claims description 6
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
125000002346 iodo group Chemical group I* 0.000 claims description 6
229910052700 potassium Inorganic materials 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
230000037396 body weight Effects 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
150000003951 lactams Chemical class 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
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 claims description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
239000003638 chemical reducing agent Substances 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
229940067621 aminobutyrate Drugs 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
230000001404 mediated effect Effects 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 claims description 3
229940102001 zinc bromide Drugs 0.000 claims description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 2
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 claims description 2
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
108010003541 Platelet Activating Factor Proteins 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000004001 thioalkyl group Chemical group 0.000 claims description 2
235000013311 vegetables Nutrition 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims 12
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims 3
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
239000005711 Benzoic acid Substances 0.000 claims 1
102100036883 Cyclin-H Human genes 0.000 claims 1
101100244064 Enterobacteria phage PRD1 XXII gene Proteins 0.000 claims 1
101000713120 Homo sapiens Cyclin-H Proteins 0.000 claims 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
229940092714 benzenesulfonic acid Drugs 0.000 claims 1
DWPHWVJZBHLVPI-UHFFFAOYSA-N bromophosphonic acid Chemical compound OP(O)(Br)=O DWPHWVJZBHLVPI-UHFFFAOYSA-N 0.000 claims 1
239000003610 charcoal Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical class CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims 1
150000004965 peroxy acids Chemical class 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
229910000104 sodium hydride Inorganic materials 0.000 claims 1
239000012312 sodium hydride Substances 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
CAJCPYDCXVZYBI-UHFFFAOYSA-N tert-butyl n-(3-methoxyphenyl)carbamate Chemical compound COC1=CC=CC(NC(=O)OC(C)(C)C)=C1 CAJCPYDCXVZYBI-UHFFFAOYSA-N 0.000 claims 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 claims 1
125000001425 triazolyl group Chemical group 0.000 claims 1
239000011701 zinc Substances 0.000 claims 1
229910052725 zinc Inorganic materials 0.000 claims 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 119
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
239000007787 solid Substances 0.000 description 49
239000000243 solution Substances 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000003921 oil Substances 0.000 description 43
235000019198 oils Nutrition 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
235000019439 ethyl acetate Nutrition 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 29
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238000006243 chemical reaction Methods 0.000 description 25
208000009144 Pure autonomic failure Diseases 0.000 description 21
239000002904 solvent Substances 0.000 description 20
238000005160 1H NMR spectroscopy Methods 0.000 description 19
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 19
239000000725 suspension Substances 0.000 description 19
238000004587 chromatography analysis Methods 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000012230 colorless oil Substances 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
239000000284 extract Substances 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
239000007858 starting material Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
238000007792 addition Methods 0.000 description 10
239000005557 antagonist Substances 0.000 description 10
229910052786 argon Inorganic materials 0.000 description 10
238000010992 reflux Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
210000003918 fraction a Anatomy 0.000 description 9
208000001953 Hypotension Diseases 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
230000027455 binding Effects 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
241000700159 Rattus Species 0.000 description 7
238000002441 X-ray diffraction Methods 0.000 description 7
230000000052 comparative effect Effects 0.000 description 7
239000003814 drug Substances 0.000 description 7
210000002196 fr. b Anatomy 0.000 description 7
230000036543 hypotension Effects 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
239000008194 pharmaceutical composition Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000007983 Tris buffer Substances 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
229940079593 drug Drugs 0.000 description 6
238000001802 infusion Methods 0.000 description 6
239000003755 preservative agent Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
239000000872 buffer Substances 0.000 description 5
239000001110 calcium chloride Substances 0.000 description 5
229910001628 calcium chloride Inorganic materials 0.000 description 5
239000007859 condensation product Substances 0.000 description 5
150000004292 cyclic ethers Chemical class 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
235000003599 food sweetener Nutrition 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000000463 material Substances 0.000 description 5
239000008188 pellet Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002671 adjuvant Substances 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 4
239000003086 colorant Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
210000004731 jugular vein Anatomy 0.000 description 4
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
230000036961 partial effect Effects 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
MZWKCFGWAWRHDY-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] 2,2-diphenylethanethioate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 MZWKCFGWAWRHDY-UHFFFAOYSA-N 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 3
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
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