KR101699145B1 - 페닐알킬설파메이트 화합물 및 이를 포함하는 근육 이완제 조성물 - Google Patents

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Publication number

KR101699145B1

KR101699145B1 KR1020147035195A KR20147035195A KR101699145B1 KR 101699145 B1 KR101699145 B1 KR 101699145B1 KR 1020147035195 A KR1020147035195 A KR 1020147035195A KR 20147035195 A KR20147035195 A KR 20147035195A KR 101699145 B1 KR101699145 B1 KR 101699145B1

Authority

KR

South Korea

Prior art keywords

methyl

preparation

dioxolan

dioxaspiro

sulfamate

Prior art date

2012-06-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• -1 Phenylalkyl sulfamate compound Chemical class 0.000 title claims abstract description 298
• 239000000203 mixture Substances 0.000 title claims description 53
• 239000003158 myorelaxant agent Substances 0.000 title description 7
• 238000000034 method Methods 0.000 claims abstract description 252
• 150000001875 compounds Chemical class 0.000 claims description 686
• 238000004519 manufacturing process Methods 0.000 claims description 305
• FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 10
• 230000003287 optical effect Effects 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 210000000278 spinal cord Anatomy 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• RZMCTLKVIWUBPA-UHFFFAOYSA-N [5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1Cl RZMCTLKVIWUBPA-UHFFFAOYSA-N 0.000 claims description 6
• 238000005906 dihydroxylation reaction Methods 0.000 claims description 6
• 239000003638 chemical reducing agent Substances 0.000 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 4
• 206010019196 Head injury Diseases 0.000 claims description 4
• QWOWRIOCXVQFRR-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=C(Cl)C=CC=C1Cl QWOWRIOCXVQFRR-UHFFFAOYSA-N 0.000 claims description 4
• XHAGRJPHZXUFFK-UHFFFAOYSA-N [5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=CC=C1Cl XHAGRJPHZXUFFK-UHFFFAOYSA-N 0.000 claims description 4
• ZJTMPSSKRYNKNG-UHFFFAOYSA-N [5-(2-chlorophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound S(N)(OCC1OC(OC1C1=C(C=CC=C1)Cl)C)(=O)=O ZJTMPSSKRYNKNG-UHFFFAOYSA-N 0.000 claims description 4
• BAPAOLGFWMELPD-UHFFFAOYSA-N [5-(2-nitrophenyl)-2-oxo-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(=O)OC1C1=CC=CC=C1[N+]([O-])=O BAPAOLGFWMELPD-UHFFFAOYSA-N 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 239000007800 oxidant agent Substances 0.000 claims description 4
• 206010057268 Spinal cord paralysis Diseases 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• 229910052783 alkali metal Inorganic materials 0.000 claims description 3
• 150000001340 alkali metals Chemical class 0.000 claims description 3
• 150000001413 amino acids Chemical class 0.000 claims description 3
• 206010008129 cerebral palsy Diseases 0.000 claims description 3
• WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 3
• 150000007524 organic acids Chemical class 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• 208000020431 spinal cord injury Diseases 0.000 claims description 3
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 3
• KSMPNKLYNWJXNI-UHFFFAOYSA-N (5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate Chemical compound S(N)(OCC1OC(OC1CC1=CC=CC=C1)(CC)CC)(=O)=O KSMPNKLYNWJXNI-UHFFFAOYSA-N 0.000 claims description 2
• GPQXADGDQZYFMV-UHFFFAOYSA-N (5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate Chemical compound S(N)(OCC1OC(OC1CC1=CC=CC=C1)(C)C)(=O)=O GPQXADGDQZYFMV-UHFFFAOYSA-N 0.000 claims description 2
• CSXDJPXXSIMJBX-UHFFFAOYSA-N 2-(5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate Chemical compound O1C(CC)(CC)OC(CCOS(N)(=O)=O)C1CC1=CC=CC=C1 CSXDJPXXSIMJBX-UHFFFAOYSA-N 0.000 claims description 2
• SFNZSFGVNUSPAU-UHFFFAOYSA-N 2-(5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate Chemical compound O1C(C)(C)OC(CCOS(N)(=O)=O)C1CC1=CC=CC=C1 SFNZSFGVNUSPAU-UHFFFAOYSA-N 0.000 claims description 2
• IQUJYITYUVTFDO-UHFFFAOYSA-N 2-[5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]ethyl sulfamate Chemical compound O1C(CC)(CC)OC(CCOS(N)(=O)=O)C1C1=CC=CC=C1Cl IQUJYITYUVTFDO-UHFFFAOYSA-N 0.000 claims description 2
• JANMWWVANVYISM-UHFFFAOYSA-N 2-[5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl sulfamate Chemical compound O1C(C)(C)OC(CCOS(N)(=O)=O)C1C1=CC=CC=C1Cl JANMWWVANVYISM-UHFFFAOYSA-N 0.000 claims description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
• 206010059245 Angiopathy Diseases 0.000 claims description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 208000003618 Intervertebral Disc Displacement Diseases 0.000 claims description 2
• 206010050296 Intervertebral disc protrusion Diseases 0.000 claims description 2
• XNPNIYWWVGGUIK-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=C(Cl)C=C1Cl XNPNIYWWVGGUIK-UHFFFAOYSA-N 0.000 claims description 2
• PZJPBLBSIBZHEU-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=C(Cl)C=C1Cl PZJPBLBSIBZHEU-UHFFFAOYSA-N 0.000 claims description 2
• VAYHBFLVNBUIQJ-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)OC(COS(N)(=O)=O)C1C1=CC=C(Cl)C=C1Cl VAYHBFLVNBUIQJ-UHFFFAOYSA-N 0.000 claims description 2
• QPUZPKPURUDSKT-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=C(Cl)C=C1Cl QPUZPKPURUDSKT-UHFFFAOYSA-N 0.000 claims description 2
• VATHXICLBXMRAO-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=C(Cl)C=CC=C1Cl VATHXICLBXMRAO-UHFFFAOYSA-N 0.000 claims description 2
• UDZGOSZSFMSKDM-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=C(Cl)C=CC=C1Cl UDZGOSZSFMSKDM-UHFFFAOYSA-N 0.000 claims description 2
• MOUITVGTOGQRGR-UHFFFAOYSA-N [5-(2-aminophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=CC=C1N MOUITVGTOGQRGR-UHFFFAOYSA-N 0.000 claims description 2
• PPMVXZLGSOOHNV-UHFFFAOYSA-N [5-(2-aminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1N PPMVXZLGSOOHNV-UHFFFAOYSA-N 0.000 claims description 2
• LNUSHCOTFXLBNS-UHFFFAOYSA-N [5-(2-aminophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1N LNUSHCOTFXLBNS-UHFFFAOYSA-N 0.000 claims description 2
• PKNWMDOCDWBNCK-UHFFFAOYSA-N [5-(2-aminophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NC1=CC=CC=C1C1C(COS(N)(=O)=O)OC(C=2C=CC=CC=2)O1 PKNWMDOCDWBNCK-UHFFFAOYSA-N 0.000 claims description 2
• UANGRXRESSDGEE-UHFFFAOYSA-N [5-(2-chlorophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=CC=C1Cl UANGRXRESSDGEE-UHFFFAOYSA-N 0.000 claims description 2
• ANYUUFVAPYZBOM-UHFFFAOYSA-N [5-(2-fluorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1F ANYUUFVAPYZBOM-UHFFFAOYSA-N 0.000 claims description 2
• ZUBCNBYVKBJOHW-UHFFFAOYSA-N [5-(2-fluorophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound S(N)(OCC1OC(OC1C1=C(C=CC=C1)F)C)(=O)=O ZUBCNBYVKBJOHW-UHFFFAOYSA-N 0.000 claims description 2
• PGKJDCCMJALRSH-UHFFFAOYSA-N [5-(2-fluorophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=CC=C1F PGKJDCCMJALRSH-UHFFFAOYSA-N 0.000 claims description 2
• DVWFSTVNQGCQOW-UHFFFAOYSA-N [5-(2-iodophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1I DVWFSTVNQGCQOW-UHFFFAOYSA-N 0.000 claims description 2
• SSQLUTKYINNSAY-UHFFFAOYSA-N [5-(2-iodophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound S(N)(OCC1OC(OC1C1=C(C=CC=C1)I)C)(=O)=O SSQLUTKYINNSAY-UHFFFAOYSA-N 0.000 claims description 2
• BDHJUEFXZRDXKT-UHFFFAOYSA-N [5-(2-iodophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=CC=C1I BDHJUEFXZRDXKT-UHFFFAOYSA-N 0.000 claims description 2
• LFJHTCHBWSCVIF-UHFFFAOYSA-N [5-(2-methylphenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound CC1=CC=CC=C1C1C(COS(N)(=O)=O)OC(C=2C=CC=CC=2)O1 LFJHTCHBWSCVIF-UHFFFAOYSA-N 0.000 claims description 2
• QXXREHAVUAFLBD-UHFFFAOYSA-N [5-(2-nitrophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=CC=C1[N+]([O-])=O QXXREHAVUAFLBD-UHFFFAOYSA-N 0.000 claims description 2
• 239000000460 chlorine Substances 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 150000007522 mineralic acids Chemical class 0.000 claims description 2
• 230000019635 sulfation Effects 0.000 claims description 2
• 238000005670 sulfation reaction Methods 0.000 claims description 2
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
• 208000019553 vascular disease Diseases 0.000 claims description 2
• 206010041591 Spinal osteoarthritis Diseases 0.000 claims 1
• 208000025434 cerebellar degeneration Diseases 0.000 claims 1
• 208000036319 cervical spondylosis Diseases 0.000 claims 1
• 208000005801 spondylosis Diseases 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 22
• 206010021118 Hypotonia Diseases 0.000 abstract description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 17
• 230000036640 muscle relaxation Effects 0.000 abstract description 17
• 208000005392 Spasm Diseases 0.000 abstract description 16
• 208000007101 Muscle Cramp Diseases 0.000 abstract description 15
• 201000010099 disease Diseases 0.000 abstract description 15
• 208000008238 Muscle Spasticity Diseases 0.000 abstract description 3
• 230000012191 relaxation of muscle Effects 0.000 abstract 1
• 238000002360 preparation method Methods 0.000 description 795
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 596
• 238000005481 NMR spectroscopy Methods 0.000 description 541
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 220
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 77
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 72
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 66
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• 239000000243 solution Substances 0.000 description 47
• BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 46
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
• 239000011541 reaction mixture Substances 0.000 description 34
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 33
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 30
• 239000000741 silica gel Substances 0.000 description 30
• 229910002027 silica gel Inorganic materials 0.000 description 30
• 238000012360 testing method Methods 0.000 description 30
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 28
• HHEIMYAXCOIQCJ-UHFFFAOYSA-N ethyl 2,2-dimethylpropanoate Chemical compound CCOC(=O)C(C)(C)C HHEIMYAXCOIQCJ-UHFFFAOYSA-N 0.000 description 27
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 24
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 23
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 21
• 239000012044 organic layer Substances 0.000 description 20
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• RBNPOMFGQQGHHO-UHFFFAOYSA-M glycerate Chemical compound OCC(O)C([O-])=O RBNPOMFGQQGHHO-UHFFFAOYSA-M 0.000 description 18
• 239000010410 layer Substances 0.000 description 18
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 16
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 229950010765 pivalate Drugs 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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• 239000008194 pharmaceutical composition Substances 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 8
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• POTRTUQCRHOIFM-VOTSOKGWSA-N methyl (e)-3-(2-chlorophenyl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=CC=C1Cl POTRTUQCRHOIFM-VOTSOKGWSA-N 0.000 description 7
• 229910000077 silane Inorganic materials 0.000 description 7
• ATKIMFDGHPQOAO-GHMZBOCLSA-N (1R,2R)-1-(2-chlorophenyl)-3-(methoxymethoxy)propane-1,2-diol Chemical compound COCOC[C@@H](O)[C@H](O)c1ccccc1Cl ATKIMFDGHPQOAO-GHMZBOCLSA-N 0.000 description 6
• SBVWZRBKTDOSDR-GQCTYLIASA-N 1-chloro-2-[(e)-3-(methoxymethoxy)prop-1-enyl]benzene Chemical compound COCOC\C=C\C1=CC=CC=C1Cl SBVWZRBKTDOSDR-GQCTYLIASA-N 0.000 description 6
• UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 6
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