JP4145230B2 - 神経障害の予防・治療剤 - Google Patents

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Publication number

JP4145230B2

JP4145230B2 JP2003369875A JP2003369875A JP4145230B2 JP 4145230 B2 JP4145230 B2 JP 4145230B2 JP 2003369875 A JP2003369875 A JP 2003369875A JP 2003369875 A JP2003369875 A JP 2003369875A JP 4145230 B2 JP4145230 B2 JP 4145230B2

Authority

JP

Japan

Prior art keywords

group

optionally substituted

compound

alkyl

examples

Prior art date

2002-11-01

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.)

Expired - Fee Related

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• 239000003814 drug Substances 0.000 title description 46
• 229940124597 therapeutic agent Drugs 0.000 title description 17
• 208000012902 Nervous system disease Diseases 0.000 title description 2
• 230000003449 preventive effect Effects 0.000 title description 2
• 208000025966 Neurological disease Diseases 0.000 title 1
• NSVIDGDZEVEYKX-XNTDXEJSSA-N (e)-n-[4-(diethoxyphosphorylmethyl)phenyl]-3-[5-(4-fluorophenyl)-1-methylpyrazol-4-yl]prop-2-enamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NC(=O)\C=C\C1=C(C=2C=CC(F)=CC=2)N(C)N=C1 NSVIDGDZEVEYKX-XNTDXEJSSA-N 0.000 claims 1
• IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical compound [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 claims 1
• -1 t-butoxy Chemical group 0.000 description 456
• 150000001875 compounds Chemical class 0.000 description 266
• 125000001424 substituent group Chemical group 0.000 description 135
• 125000000217 alkyl group Chemical group 0.000 description 119
• 238000006243 chemical reaction Methods 0.000 description 103
• 150000002430 hydrocarbons Chemical group 0.000 description 99
• 125000005843 halogen group Chemical group 0.000 description 97
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 91
• 238000000034 method Methods 0.000 description 85
• 229910052731 fluorine Inorganic materials 0.000 description 74
• 239000002904 solvent Substances 0.000 description 72
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 71
• 239000011737 fluorine Substances 0.000 description 71
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 70
• 239000000460 chlorine Substances 0.000 description 70
• 229910052801 chlorine Inorganic materials 0.000 description 70
• 125000000623 heterocyclic group Chemical group 0.000 description 69
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 69
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 68
• 229910052794 bromium Inorganic materials 0.000 description 68
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 67
• 229910052740 iodine Inorganic materials 0.000 description 61
• 235000002639 sodium chloride Nutrition 0.000 description 57
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• 150000003839 salts Chemical class 0.000 description 47
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
• 125000002252 acyl group Chemical group 0.000 description 45
• 239000002585 base Substances 0.000 description 44
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
• 125000003118 aryl group Chemical group 0.000 description 41
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
• 239000000203 mixture Substances 0.000 description 40
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 40
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• 239000003795 chemical substances by application Substances 0.000 description 39
• 229930195733 hydrocarbon Natural products 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
• 230000002411 adverse Effects 0.000 description 35
• 125000004433 nitrogen atom Chemical group N* 0.000 description 35
• 239000004215 Carbon black (E152) Substances 0.000 description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
• 239000011541 reaction mixture Substances 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 125000003710 aryl alkyl group Chemical group 0.000 description 33
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 33
• 125000005915 C6-C14 aryl group Chemical group 0.000 description 32
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
• 125000002015 acyclic group Chemical group 0.000 description 32
• 125000003545 alkoxy group Chemical group 0.000 description 31
• 238000001953 recrystallisation Methods 0.000 description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 30
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 29
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
• 229940079593 drug Drugs 0.000 description 29
• 125000004076 pyridyl group Chemical group 0.000 description 29
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 125000003277 amino group Chemical group 0.000 description 27
• 108010025020 Nerve Growth Factor Proteins 0.000 description 25
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 25
• 239000011630 iodine Chemical group 0.000 description 25
• 125000000714 pyrimidinyl group Chemical group 0.000 description 25
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 24
• 239000002253 acid Substances 0.000 description 24
• 238000002360 preparation method Methods 0.000 description 24
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 23
• 239000007788 liquid Substances 0.000 description 23
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 22
• 239000013078 crystal Substances 0.000 description 22
• 238000000926 separation method Methods 0.000 description 22
• 230000002829 reductive effect Effects 0.000 description 21
• 125000001425 triazolyl group Chemical group 0.000 description 21
• 125000004122 cyclic group Chemical group 0.000 description 20
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 20
• 125000002971 oxazolyl group Chemical group 0.000 description 20
• 230000035484 reaction time Effects 0.000 description 20
• 125000000335 thiazolyl group Chemical group 0.000 description 20
• 102000007072 Nerve Growth Factors Human genes 0.000 description 19
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 19
• 238000004587 chromatography analysis Methods 0.000 description 19
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 19
• 238000000746 purification Methods 0.000 description 19
• 125000000547 substituted alkyl group Chemical group 0.000 description 19
• 125000003831 tetrazolyl group Chemical group 0.000 description 19
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 19
• 238000002425 crystallisation Methods 0.000 description 18
• 230000008025 crystallization Effects 0.000 description 18
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 18
• 238000000638 solvent extraction Methods 0.000 description 18
• 238000012546 transfer Methods 0.000 description 18
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 17
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
• 150000002170 ethers Chemical class 0.000 description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
• 125000002883 imidazolyl group Chemical group 0.000 description 17
• 239000000243 solution Substances 0.000 description 17
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
• 125000002947 alkylene group Chemical group 0.000 description 16
• 150000008282 halocarbons Chemical class 0.000 description 16
• 239000003921 oil Substances 0.000 description 16
• 235000019198 oils Nutrition 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 125000003226 pyrazolyl group Chemical group 0.000 description 16
• 150000003536 tetrazoles Chemical group 0.000 description 16
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 16
• 150000003852 triazoles Chemical class 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 15
• 229910052757 nitrogen Inorganic materials 0.000 description 15
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 125000001931 aliphatic group Chemical group 0.000 description 14
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 239000003112 inhibitor Substances 0.000 description 14
• 238000004519 manufacturing process Methods 0.000 description 14
• 238000002844 melting Methods 0.000 description 14
• 230000008018 melting Effects 0.000 description 14
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 14
• 125000004193 piperazinyl group Chemical group 0.000 description 14
• 125000003386 piperidinyl group Chemical group 0.000 description 14
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 14
• 125000001113 thiadiazolyl group Chemical group 0.000 description 14
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 13
• 125000002723 alicyclic group Chemical group 0.000 description 13
• 238000010438 heat treatment Methods 0.000 description 13
• 239000001257 hydrogen Substances 0.000 description 13
• 229910052739 hydrogen Inorganic materials 0.000 description 13
• 125000002950 monocyclic group Chemical group 0.000 description 13
• 125000002757 morpholinyl group Chemical group 0.000 description 13
• 239000003900 neurotrophic factor Substances 0.000 description 13
• 125000005493 quinolyl group Chemical group 0.000 description 13
• 235000011121 sodium hydroxide Nutrition 0.000 description 13
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 12
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
• 238000005481 NMR spectroscopy Methods 0.000 description 12
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 12
• 230000003287 optical effect Effects 0.000 description 12
• 125000001715 oxadiazolyl group Chemical group 0.000 description 12
• 208000033808 peripheral neuropathy Diseases 0.000 description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
• 230000028327 secretion Effects 0.000 description 12
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 11
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 11
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 11
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 11
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 11
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
• 239000012044 organic layer Substances 0.000 description 11
• 125000004430 oxygen atom Chemical group O* 0.000 description 11
• 239000008096 xylene Substances 0.000 description 11
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 10
• QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 10
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 10
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 10
• 229910052783 alkali metal Inorganic materials 0.000 description 10
• 150000001408 amides Chemical class 0.000 description 10
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
• 150000001721 carbon Chemical group 0.000 description 10
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
• 125000001072 heteroaryl group Chemical group 0.000 description 10
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
• 201000001119 neuropathy Diseases 0.000 description 10
• 230000007823 neuropathy Effects 0.000 description 10
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 description 9
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 9
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
• 125000004429 atom Chemical group 0.000 description 9
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 9
• 230000002140 halogenating effect Effects 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• 229910052717 sulfur Inorganic materials 0.000 description 9
• 125000003396 thiol group Chemical group [H]S* 0.000 description 9
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
• 241000124008 Mammalia Species 0.000 description 8
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
• 230000009471 action Effects 0.000 description 8
• 150000001298 alcohols Chemical class 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 125000002541 furyl group Chemical group 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 235000011118 potassium hydroxide Nutrition 0.000 description 8
• 229910000029 sodium carbonate Inorganic materials 0.000 description 8
• 235000017550 sodium carbonate Nutrition 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• 125000001544 thienyl group Chemical group 0.000 description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 7
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
• 125000004450 alkenylene group Chemical group 0.000 description 7
• 125000005530 alkylenedioxy group Chemical group 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 7
• 239000000920 calcium hydroxide Substances 0.000 description 7
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 7
• 239000001768 carboxy methyl cellulose Substances 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
• 238000006460 hydrolysis reaction Methods 0.000 description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
• 230000000069 prophylactic effect Effects 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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