KR20180030166A

KR20180030166A - 2-아미노-1,3,4-티아디아진 및 2-아미노-1,3,4-옥사디아진 기반 항진균제

2-아미노-1,3,4-티아디아진 및 2-아미노-1,3,4-옥사디아진 기반 항진균제 Download PDF

Info

Publication number: KR20180030166A
Authority: KR; South Korea
Prior art keywords: thiazin; amine; alkyl; butyl; methoxy
Prior art date: 2015-07-14
Legal status : Withdrawn

Application number

KR1020187004510A

Other languages

English (en)

Korean (ko)

Inventor

그레헴 에듀워드 모리스 시브리

라스 조나스 말름스트렘

조안나 마리아 라르송

Original Assignee

에프2지 리미티드

Priority date

2015-07-14

Filing date

2016-07-14

Publication date

2018-03-21

2016-07-14 Application filed by 에프2지 리미티드 filed Critical 에프2지 리미티드

2018-03-21 Publication of KR20180030166A publication Critical patent/KR20180030166A/ko

Status Withdrawn legal-status Critical Current

Links

229940121375 antifungal agent Drugs 0.000 title claims abstract description 40
239000003429 antifungal agent Substances 0.000 title claims abstract description 38
WNLXZSXQMYFYHG-UHFFFAOYSA-N 2h-1,3,4-thiadiazin-2-amine Chemical compound NC1SC=CN=N1 WNLXZSXQMYFYHG-UHFFFAOYSA-N 0.000 title 1
BNXJHDGIKNKIAI-UHFFFAOYSA-N NC1OC=CN=N1 Chemical compound NC1OC=CN=N1 BNXJHDGIKNKIAI-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 176
150000003839 salts Chemical class 0.000 claims abstract description 32
-1 - (C 1 -C 4 alkyl) Chemical group 0.000 claims description 472
239000000203 mixture Substances 0.000 claims description 272
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 150
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 129
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 116
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 87
229910052736 halogen Inorganic materials 0.000 claims description 66
150000002367 halogens Chemical class 0.000 claims description 66
125000004450 alkenylene group Chemical group 0.000 claims description 65
125000003118 aryl group Chemical group 0.000 claims description 65
125000002947 alkylene group Chemical group 0.000 claims description 63
125000000217 alkyl group Chemical group 0.000 claims description 61
125000000623 heterocyclic group Chemical group 0.000 claims description 51
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 47
125000001424 substituent group Chemical group 0.000 claims description 40
238000000034 method Methods 0.000 claims description 39
125000001072 heteroaryl group Chemical group 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 33
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 31
229910052799 carbon Inorganic materials 0.000 claims description 30
208000031888 Mycoses Diseases 0.000 claims description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
125000004452 carbocyclyl group Chemical group 0.000 claims description 22
125000000753 cycloalkyl group Chemical group 0.000 claims description 22
125000005842 heteroatom Chemical group 0.000 claims description 22
125000004104 aryloxy group Chemical group 0.000 claims description 21
238000011282 treatment Methods 0.000 claims description 20
206010017533 Fungal infection Diseases 0.000 claims description 19
241000223218 Fusarium Species 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000004429 atom Chemical group 0.000 claims description 17
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 16
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 15
229920006395 saturated elastomer Polymers 0.000 claims description 15
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 13
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 13
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
241000228212 Aspergillus Species 0.000 claims description 11
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 10
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 9
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 8
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 8
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 8
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
230000002265 prevention Effects 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
241001465754 Metazoa Species 0.000 claims description 7
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000005975 2-phenylethyloxy group Chemical group 0.000 claims description 6
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 6
241000233866 Fungi Species 0.000 claims description 6
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 5
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
CJKLUMPOZDSVKY-UHFFFAOYSA-N 2,3-dihydro-1h-isoindole-1,3-diol Chemical compound C1=CC=C2C(O)NC(O)C2=C1 CJKLUMPOZDSVKY-UHFFFAOYSA-N 0.000 claims description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
LMSXJSHJKDFJII-UHFFFAOYSA-N 2h-1,2-benzothiazin-3-amine Chemical compound C1=CC=C2SNC(N)=CC2=C1 LMSXJSHJKDFJII-UHFFFAOYSA-N 0.000 claims description 3
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
125000005977 3-phenylpropyloxy 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
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
241001337994 Cryptococcus <scale insect> Species 0.000 claims description 3
ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 3
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
HHEKTBXNKQFGLT-UHFFFAOYSA-N 5-benzyl-2H-1,3,4-thiadiazin-2-amine Chemical compound NC1SC=C(N=N1)CC1=CC=CC=C1 HHEKTBXNKQFGLT-UHFFFAOYSA-N 0.000 claims description 2
230000002538 fungal effect Effects 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
206010070834 Sensitisation Diseases 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
230000008313 sensitization Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 403
238000006243 chemical reaction Methods 0.000 description 358
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 337
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 279
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 235
238000004809 thin layer chromatography Methods 0.000 description 206
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 205
239000000047 product Substances 0.000 description 179
239000002904 solvent Substances 0.000 description 166
239000007787 solid Substances 0.000 description 164
239000011541 reaction mixture Substances 0.000 description 140
239000000460 chlorine Substances 0.000 description 123
206010057190 Respiratory tract infections Diseases 0.000 description 116
235000019439 ethyl acetate Nutrition 0.000 description 113
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
239000007788 liquid Substances 0.000 description 84
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
238000007792 addition Methods 0.000 description 66
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
239000013058 crude material Substances 0.000 description 60
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
238000004440 column chromatography Methods 0.000 description 59
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 58
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 46
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 44
238000010992 reflux Methods 0.000 description 43
238000000746 purification Methods 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
239000000741 silica gel Substances 0.000 description 35
229910002027 silica gel Inorganic materials 0.000 description 35
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 32
239000012044 organic layer Substances 0.000 description 31
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 30
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 30
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 30
229910052794 bromium Inorganic materials 0.000 description 30
235000002639 sodium chloride Nutrition 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000012043 crude product Substances 0.000 description 27
239000012047 saturated solution Substances 0.000 description 26
239000010410 layer Substances 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 23
239000000284 extract Substances 0.000 description 23
238000009472 formulation Methods 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
108010046334 Urease Proteins 0.000 description 21
238000004458 analytical method Methods 0.000 description 21
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 20
239000003480 eluent Substances 0.000 description 19
239000003208 petroleum Substances 0.000 description 19
239000011734 sodium Substances 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000012267 brine Substances 0.000 description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
239000007864 aqueous solution Substances 0.000 description 12
238000012544 monitoring process Methods 0.000 description 12
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000002253 acid Substances 0.000 description 11
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 11
239000007789 gas Substances 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
241000196324 Embryophyta Species 0.000 description 9
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 9
239000012156 elution solvent Substances 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
125000003342 alkenyl group Chemical group 0.000 description 8
239000002585 base Substances 0.000 description 8
239000000428 dust Substances 0.000 description 8
239000007791 liquid phase Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
125000001246 bromo group Chemical group Br* 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000008187 granular material Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 7
235000019345 sodium thiosulphate Nutrition 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
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