TW219934B

TW219934B -

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Publication number: TW219934B
Authority: TW; Taiwan
Prior art keywords: formula; alkyl; compound; hydroxylamine; hydroxyurea
Prior art date: 1990-03-27

Application number

TW080103062A

Other languages

English (en)

Chinese (zh)

Original Assignee

Smithkline Beecham Corp

Priority date

1990-03-27

Filing date

1991-04-20

Publication date

1994-02-01

1991-04-20 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

1994-02-01 Application granted granted Critical

1994-02-01 Publication of TW219934B publication Critical patent/TW219934B/zh

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150000001875 compounds Chemical class 0.000 claims description 282
239000000203 mixture Substances 0.000 claims description 183
-1 CK2 alkyl amides Chemical class 0.000 claims description 158
239000000243 solution Substances 0.000 claims description 138
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 134
239000002904 solvent Substances 0.000 claims description 102
238000011049 filling Methods 0.000 claims description 100
125000000217 alkyl group Chemical group 0.000 claims description 96
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 93
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 92
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 91
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 90
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 75
238000000034 method Methods 0.000 claims description 72
239000000284 extract Substances 0.000 claims description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 66
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 66
229910052739 hydrogen Inorganic materials 0.000 claims description 64
229920006395 saturated elastomer Polymers 0.000 claims description 63
239000001257 hydrogen Substances 0.000 claims description 61
239000007787 solid Substances 0.000 claims description 59
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 58
229910001868 water Inorganic materials 0.000 claims description 57
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
229910052786 argon Inorganic materials 0.000 claims description 52
230000002829 reductive effect Effects 0.000 claims description 52
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 51
239000002253 acid Substances 0.000 claims description 51
238000006243 chemical reaction Methods 0.000 claims description 51
239000011780 sodium chloride Substances 0.000 claims description 46
150000001412 amines Chemical class 0.000 claims description 45
235000019439 ethyl acetate Nutrition 0.000 claims description 45
239000007789 gas Substances 0.000 claims description 45
229960001330 hydroxycarbamide Drugs 0.000 claims description 45
150000002923 oximes Chemical class 0.000 claims description 44
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims description 36
239000011541 reaction mixture Substances 0.000 claims description 35
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 33
239000000543 intermediate Substances 0.000 claims description 31
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 30
238000003756 stirring Methods 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 28
239000002585 base Substances 0.000 claims description 28
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 27
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 claims description 26
238000000746 purification Methods 0.000 claims description 25
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 24
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
238000012360 testing method Methods 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000011734 sodium Substances 0.000 claims description 20
238000004458 analytical method Methods 0.000 claims description 19
239000001301 oxygen Substances 0.000 claims description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
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 18
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
229910052708 sodium Inorganic materials 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 17
238000010511 deprotection reaction Methods 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 16
125000001624 naphthyl group Chemical group 0.000 claims description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 15
229910000027 potassium carbonate Inorganic materials 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 15
230000002378 acidificating effect Effects 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
150000002443 hydroxylamines Chemical class 0.000 claims description 13
230000002401 inhibitory effect Effects 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 13
229910000029 sodium carbonate Inorganic materials 0.000 claims description 13
239000003929 acidic solution Substances 0.000 claims description 12
239000012298 atmosphere Substances 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 11
150000002367 halogens Chemical group 0.000 claims description 11
230000003647 oxidation Effects 0.000 claims description 11
238000007254 oxidation reaction Methods 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
101150041968 CDC13 gene Proteins 0.000 claims description 10
235000014676 Phragmites communis Nutrition 0.000 claims description 10
231100000252 nontoxic Toxicity 0.000 claims description 10
230000003000 nontoxic effect Effects 0.000 claims description 10
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
238000010992 reflux Methods 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
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 7
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 7
150000001768 cations Chemical class 0.000 claims description 7
235000019441 ethanol Nutrition 0.000 claims description 7
238000004128 high performance liquid chromatography Methods 0.000 claims description 7
239000012948 isocyanate Substances 0.000 claims description 7
150000002513 isocyanates Chemical class 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
239000011575 calcium Substances 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
238000004090 dissolution Methods 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 6
229910052737 gold Inorganic materials 0.000 claims description 6
239000010931 gold Substances 0.000 claims description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
229910000069 nitrogen hydride Inorganic materials 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
238000010306 acid treatment Methods 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
125000005002 aryl methyl group Chemical group 0.000 claims description 5
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
229910052791 calcium Inorganic materials 0.000 claims description 5
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
229960003750 ethyl chloride Drugs 0.000 claims description 5
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 5
238000007639 printing Methods 0.000 claims description 5
150000003254 radicals Chemical group 0.000 claims description 5
230000001568 sexual effect Effects 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
210000003608 fece Anatomy 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 claims description 4
239000004475 Arginine Substances 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 3
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
102000003820 Lipoxygenases Human genes 0.000 claims description 3
108090000128 Lipoxygenases Proteins 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 claims description 3
WGYFACNYUJGZQO-UHFFFAOYSA-N aminomethanetriol Chemical compound NC(O)(O)O WGYFACNYUJGZQO-UHFFFAOYSA-N 0.000 claims description 3
239000000908 ammonium hydroxide Substances 0.000 claims description 3
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
235000013405 beer Nutrition 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000005336 cracking Methods 0.000 claims description 3
230000006378 damage Effects 0.000 claims description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
229910052743 krypton Inorganic materials 0.000 claims description 3
DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
239000000052 vinegar Substances 0.000 claims description 3
235000021419 vinegar Nutrition 0.000 claims description 3
HGXVXGSOOPCMHM-UHFFFAOYSA-N 1-hydroxy-1-(6-phenylmethoxy-1,2,3,4-tetrahydronaphthalen-1-yl)urea Chemical compound C=1C=C2C(N(O)C(=O)N)CCCC2=CC=1OCC1=CC=CC=C1 HGXVXGSOOPCMHM-UHFFFAOYSA-N 0.000 claims description 2
IZFMIIGMIPRYKL-HNQUOIGGSA-N 3-(5-nitro-2-furyl)acrylamide Chemical compound NC(=O)\C=C\C1=CC=C([N+]([O-])=O)O1 IZFMIIGMIPRYKL-HNQUOIGGSA-N 0.000 claims description 2
241000196324 Embryophyta Species 0.000 claims description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
150000008065 acid anhydrides Chemical class 0.000 claims description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 claims description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
229910000077 silane Inorganic materials 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
238000005160 1H NMR spectroscopy Methods 0.000 claims 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 3
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims 3
150000007530 organic bases Chemical class 0.000 claims 3
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims 3
101100459438 Caenorhabditis elegans nac-1 gene Proteins 0.000 claims 2
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
238000005481 NMR spectroscopy Methods 0.000 claims 2
235000002791 Panax Nutrition 0.000 claims 2
241000208343 Panax Species 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
102000005262 Sulfatase Human genes 0.000 claims 2
239000003513 alkali Substances 0.000 claims 2
229910052783 alkali metal Inorganic materials 0.000 claims 2
150000001340 alkali metals Chemical class 0.000 claims 2
229910000085 borane Inorganic materials 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
150000007529 inorganic bases Chemical class 0.000 claims 2
PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 claims 2
108060007951 sulfatase Proteins 0.000 claims 2
AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 claims 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 claims 1
YYOXBJRAUDWYMQ-UHFFFAOYSA-N 2-sulfonyl-3h-furan Chemical compound O=S(=O)=C1CC=CO1 YYOXBJRAUDWYMQ-UHFFFAOYSA-N 0.000 claims 1
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