TWI284130B - New derivatives of purine, their preparation process, their use as medicaments, pharmaceutical compositions and new use - Google Patents

Info

Publication number

TWI284130B

TWI284130B TW089108817A TW89108817A TWI284130B TW I284130 B TWI284130 B TW I284130B TW 089108817 A TW089108817 A TW 089108817A TW 89108817 A TW89108817 A TW 89108817A TW I284130 B TWI284130 B TW I284130B

Authority

TW

Taiwan

Prior art keywords

group

formula

trans

product

cyclopentyl

Prior art date

1999-05-21

Links

• Espacenet
• Global Dossier
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• 239000003814 drug Substances 0.000 title claims abstract description 19
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 12
• 238000002360 preparation method Methods 0.000 title claims description 6
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
• -1 -CH2-heterocyclic Chemical group 0.000 claims abstract description 249
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 94
• 150000003839 salts Chemical class 0.000 claims abstract description 64
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 32
• 125000003118 aryl group Chemical group 0.000 claims abstract description 28
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
• 239000001257 hydrogen Substances 0.000 claims abstract description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
• 239000005864 Sulphur Substances 0.000 claims abstract 3
• 239000000047 product Substances 0.000 claims description 553
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 192
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 120
• 238000000034 method Methods 0.000 claims description 116
• 150000001875 compounds Chemical class 0.000 claims description 76
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 70
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• 238000006243 chemical reaction Methods 0.000 claims description 64
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
• 230000002079 cooperative effect Effects 0.000 claims description 55
• 239000002253 acid Substances 0.000 claims description 52
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
• MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
• 125000005843 halogen group Chemical group 0.000 claims description 23
• XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 21
• 125000004429 atom Chemical group 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 150000007522 mineralic acids Chemical class 0.000 claims description 18
• 150000007524 organic acids Chemical class 0.000 claims description 18
• 150000007529 inorganic bases Chemical class 0.000 claims description 17
• 150000007530 organic bases Chemical class 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 229940079593 drug Drugs 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 12
• 235000005985 organic acids Nutrition 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
• 150000002148 esters Chemical group 0.000 claims description 10
• 125000000524 functional group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
• 206010000269 abscess Diseases 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 238000007127 saponification reaction Methods 0.000 claims description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 8
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• SJSWRKNSCWKNIR-UHFFFAOYSA-N azane;dihydrochloride Chemical compound N.Cl.Cl SJSWRKNSCWKNIR-UHFFFAOYSA-N 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 238000002512 chemotherapy Methods 0.000 claims description 5
• 239000000126 substance Substances 0.000 claims description 5
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
• 239000007789 gas Substances 0.000 claims description 4
• 210000005036 nerve Anatomy 0.000 claims description 4
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
• 230000003071 parasitic effect Effects 0.000 claims description 4
• 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 3
• 229910021529 ammonia Inorganic materials 0.000 claims description 3
• 230000002927 anti-mitotic effect Effects 0.000 claims description 3
• 230000002555 anti-neurodegenerative effect Effects 0.000 claims description 3
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 230000004770 neurodegeneration Effects 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 238000006722 reduction reaction Methods 0.000 claims description 3
• NIBKWZHOGUHVIQ-UHFFFAOYSA-N 2-phenylacetonitrile dihydrochloride Chemical compound Cl.Cl.C(C1=CC=CC=C1)C#N NIBKWZHOGUHVIQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• 201000010099 disease Diseases 0.000 claims description 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
• 239000012948 isocyanate Substances 0.000 claims description 2
• 150000002513 isocyanates Chemical class 0.000 claims description 2
• 239000013589 supplement Substances 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 1
• 230000001405 anti-neuronal effect Effects 0.000 claims 1
• 229910052786 argon Inorganic materials 0.000 claims 1
• JLVWYWVLMFVCDI-UHFFFAOYSA-N diethyl benzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1 JLVWYWVLMFVCDI-UHFFFAOYSA-N 0.000 claims 1
• 230000008030 elimination Effects 0.000 claims 1
• 238000003379 elimination reaction Methods 0.000 claims 1
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 21
• 229910052760 oxygen Inorganic materials 0.000 abstract description 10
• 239000001301 oxygen Substances 0.000 abstract description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 7
• 150000002431 hydrogen Chemical group 0.000 abstract description 7
• 101100294106 Caenorhabditis elegans nhr-3 gene Chemical group 0.000 abstract description 5
• 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 abstract description 3
• 229910052736 halogen Inorganic materials 0.000 abstract 1
• 150000002367 halogens Chemical group 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 393
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 385
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 290
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 280
• 239000012429 reaction media Substances 0.000 description 241
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 206
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 165
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 135
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 103
• 239000003480 eluent Substances 0.000 description 101
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 100
• 235000019439 ethyl acetate Nutrition 0.000 description 97
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 84
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 84
• 239000000908 ammonium hydroxide Substances 0.000 description 84
• 239000013078 crystal Substances 0.000 description 82
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 71
• 239000002904 solvent Substances 0.000 description 71
• 125000004432 carbon atom Chemical group C* 0.000 description 67
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 66
• 238000001035 drying Methods 0.000 description 65
• VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 58
• 238000004587 chromatography analysis Methods 0.000 description 56
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
• 238000000926 separation method Methods 0.000 description 54
• 230000002829 reductive effect Effects 0.000 description 48
• 239000000243 solution Substances 0.000 description 45
• 238000005406 washing Methods 0.000 description 41
• 239000007864 aqueous solution Substances 0.000 description 39
• 229920006395 saturated elastomer Polymers 0.000 description 36
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 35
• 239000012071 phase Substances 0.000 description 34
• 108010010803 Gelatin Proteins 0.000 description 33
• 239000008273 gelatin Substances 0.000 description 33
• 229920000159 gelatin Polymers 0.000 description 33
• 235000019322 gelatine Nutrition 0.000 description 33
• 235000011852 gelatine desserts Nutrition 0.000 description 33
• 238000000746 purification Methods 0.000 description 33
• 238000000605 extraction Methods 0.000 description 32
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 31
• 239000011780 sodium chloride Substances 0.000 description 31
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• 238000001704 evaporation Methods 0.000 description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
• 239000000741 silica gel Substances 0.000 description 28
• 229910002027 silica gel Inorganic materials 0.000 description 28
• 230000008020 evaporation Effects 0.000 description 26
• 238000010898 silica gel chromatography Methods 0.000 description 23
• 150000003254 radicals Chemical class 0.000 description 21
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 19
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
• 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 description 18
• 239000000203 mixture Substances 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
• 239000011734 sodium Substances 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 239000002689 soil Substances 0.000 description 12
• 239000007787 solid Substances 0.000 description 12
• VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 11
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 11
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 10
• 125000004430 oxygen atom Chemical group O* 0.000 description 10
• 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 150000001335 aliphatic alkanes Chemical class 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 238000010438 heat treatment Methods 0.000 description 9
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
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• 239000000284 extract Substances 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
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• 229910052801 chlorine Inorganic materials 0.000 description 7
• 238000002425 crystallisation Methods 0.000 description 7
• 230000008025 crystallization Effects 0.000 description 7
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 7
• 238000007429 general method Methods 0.000 description 7
• 229940093915 gynecological organic acid Drugs 0.000 description 7
• 238000011068 loading method Methods 0.000 description 7
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 229910052717 sulfur Inorganic materials 0.000 description 7
• 125000004434 sulfur atom Chemical group 0.000 description 7
• 235000018553 tannin Nutrition 0.000 description 7
• 229920001864 tannin Polymers 0.000 description 7
• 239000001648 tannin Substances 0.000 description 7
• 230000003442 weekly effect Effects 0.000 description 7
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
• 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 description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
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• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
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• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
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• AQBJGAUQEJFPKZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CN)C=C1 AQBJGAUQEJFPKZ-UHFFFAOYSA-N 0.000 description 6
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 5
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
• 241000209094 Oryza Species 0.000 description 5
• 235000007164 Oryza sativa Nutrition 0.000 description 5
• ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 5
• 125000003158 alcohol group Chemical group 0.000 description 5
• 125000004414 alkyl thio group Chemical group 0.000 description 5
• BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 238000006482 condensation reaction Methods 0.000 description 5
• 150000004985 diamines Chemical class 0.000 description 5
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
• 239000000499 gel Substances 0.000 description 5
• 230000002401 inhibitory effect Effects 0.000 description 5
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• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 230000008569 process Effects 0.000 description 5
• 235000009566 rice Nutrition 0.000 description 5
• 229940124530 sulfonamide Drugs 0.000 description 5
• 239000011975 tartaric acid Substances 0.000 description 5
• 235000002906 tartaric acid Nutrition 0.000 description 5
• 239000005711 Benzoic acid Substances 0.000 description 4
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
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