NO833857L - Nye benzodioksolderivater, fremgangsmaate til deres fremstilling og tilsvarende farmasoeytiske sammensetninger - Google Patents

Info

Publication number

NO833857L

NO833857L NO833857A NO833857A NO833857L NO 833857 L NO833857 L NO 833857L NO 833857 A NO833857 A NO 833857A NO 833857 A NO833857 A NO 833857A NO 833857 L NO833857 L NO 833857L

Authority

NO

Norway

Prior art keywords

general formula

compound

hydrogen

alk

radical

Prior art date

1982-10-22

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• 238000000034 method Methods 0.000 title claims abstract description 46
• 238000002360 preparation method Methods 0.000 title claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 169
• -1 hexa-methyleneimino, 4-morpholinyl Chemical group 0.000 claims abstract description 95
• 150000003839 salts Chemical class 0.000 claims abstract description 94
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 78
• 239000001257 hydrogen Substances 0.000 claims abstract description 78
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 66
• 239000002253 acid Substances 0.000 claims abstract description 46
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 41
• 150000002367 halogens Chemical class 0.000 claims abstract description 37
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
• 125000003118 aryl group Chemical group 0.000 claims abstract description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
• 125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 9
• 150000008064 anhydrides Chemical class 0.000 claims abstract description 9
• 125000001589 carboacyl group Chemical group 0.000 claims abstract description 9
• 230000008569 process Effects 0.000 claims abstract description 9
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 7
• 125000004450 alkenylene group Chemical group 0.000 claims abstract description 7
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
• 150000001450 anions Chemical class 0.000 claims abstract description 6
• 238000011065 in-situ storage Methods 0.000 claims abstract description 6
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
• 239000001301 oxygen Substances 0.000 claims abstract description 6
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
• 230000003287 optical effect Effects 0.000 claims abstract description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
• 229910021645 metal ion Inorganic materials 0.000 claims abstract description 4
• 125000001424 substituent group Chemical group 0.000 claims abstract description 4
• 150000002736 metal compounds Chemical class 0.000 claims abstract description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 37
• 229910052740 iodine Inorganic materials 0.000 claims description 19
• 125000001931 aliphatic group Chemical group 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 239000000460 chlorine Chemical group 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• PPQRZUISBCMUGX-UHFFFAOYSA-N 5-(benzenesulfonyl)-6-methyl-1,3-benzodioxole-2-carboxylic acid Chemical compound CC1=CC=2OC(C(O)=O)OC=2C=C1S(=O)(=O)C1=CC=CC=C1 PPQRZUISBCMUGX-UHFFFAOYSA-N 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
• 125000001118 alkylidene group Chemical group 0.000 claims description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• QZDYUGFMUNKWDR-UHFFFAOYSA-N 5-chloro-6-(4-chlorophenyl)sulfonyl-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)O)OC2=CC(Cl)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 QZDYUGFMUNKWDR-UHFFFAOYSA-N 0.000 claims description 4
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 3
• YHLLXWFBUFNNKY-UHFFFAOYSA-N 5-(2-chlorophenyl)sulfonyl-6-methyl-1,3-benzodioxole-2-carboxylic acid Chemical compound CC1=CC=2OC(C(O)=O)OC=2C=C1S(=O)(=O)C1=CC=CC=C1Cl YHLLXWFBUFNNKY-UHFFFAOYSA-N 0.000 claims description 2
• WBWYHYWZRXYNBL-UHFFFAOYSA-N 5-(3-chlorophenyl)sulfonyl-6-methyl-1,3-benzodioxole-2-carboxylic acid Chemical compound CC1=CC=2OC(C(O)=O)OC=2C=C1S(=O)(=O)C1=CC=CC(Cl)=C1 WBWYHYWZRXYNBL-UHFFFAOYSA-N 0.000 claims description 2
• CITKQNPKVNJFSS-UHFFFAOYSA-N 5-chloro-6-(2-chlorophenyl)sulfonyl-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)O)OC2=CC(Cl)=C1S(=O)(=O)C1=CC=CC=C1Cl CITKQNPKVNJFSS-UHFFFAOYSA-N 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
• ZHVZALHRRYAEOD-UHFFFAOYSA-N 5-chloro-6-(3-chlorophenyl)sulfonyl-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)O)OC2=CC(Cl)=C1S(=O)(=O)C1=CC=CC(Cl)=C1 ZHVZALHRRYAEOD-UHFFFAOYSA-N 0.000 claims 1
• 125000004430 oxygen atom Chemical group O* 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 abstract description 10
• 125000003342 alkenyl group Chemical group 0.000 abstract description 9
• 125000000304 alkynyl group Chemical group 0.000 abstract description 5
• 125000002950 monocyclic group Chemical group 0.000 abstract description 5
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract description 4
• 125000005843 halogen group Chemical group 0.000 abstract description 4
• 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 abstract description 3
• 125000005842 heteroatom Chemical group 0.000 abstract 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
• 150000001768 cations Chemical class 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 198
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 120
• 239000000243 solution Substances 0.000 description 92
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 91
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 75
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 75
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
• 235000002639 sodium chloride Nutrition 0.000 description 64
• 239000013078 crystal Substances 0.000 description 61
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
• SIEILFNCEFEENQ-UHFFFAOYSA-N dibromoacetic acid Chemical compound OC(=O)C(Br)Br SIEILFNCEFEENQ-UHFFFAOYSA-N 0.000 description 48
• ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 39
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• 229910000027 potassium carbonate Inorganic materials 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
• 239000000203 mixture Substances 0.000 description 37
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 35
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 31
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 30
• 239000000126 substance Substances 0.000 description 29
• 229910052938 sodium sulfate Inorganic materials 0.000 description 26
• 235000011152 sodium sulphate Nutrition 0.000 description 26
• 239000007858 starting material Substances 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 25
• 239000011541 reaction mixture Substances 0.000 description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
• 238000003756 stirring Methods 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• 235000011121 sodium hydroxide Nutrition 0.000 description 21
• 239000002585 base Substances 0.000 description 20
• 239000002904 solvent Substances 0.000 description 19
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
• 150000002148 esters Chemical class 0.000 description 16
• 239000013543 active substance Substances 0.000 description 15
• 150000001735 carboxylic acids Chemical class 0.000 description 15
• 235000010265 sodium sulphite Nutrition 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
• 238000009833 condensation Methods 0.000 description 14
• 230000005494 condensation Effects 0.000 description 14
• IWYBVQLPTCMVFO-UHFFFAOYSA-N ethyl 2,2-dichloroacetate Chemical compound CCOC(=O)C(Cl)Cl IWYBVQLPTCMVFO-UHFFFAOYSA-N 0.000 description 14
• 239000003921 oil Substances 0.000 description 14
• 235000019198 oils Nutrition 0.000 description 14
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• 239000012074 organic phase Substances 0.000 description 13
• 230000009467 reduction Effects 0.000 description 13
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
• 238000010626 work up procedure Methods 0.000 description 12
• 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 11
• 239000002609 medium Substances 0.000 description 11
• 238000001953 recrystallisation Methods 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• 150000007513 acids Chemical class 0.000 description 10
• 238000009835 boiling Methods 0.000 description 10
• 238000002425 crystallisation Methods 0.000 description 10
• 230000008025 crystallization Effects 0.000 description 10
• 239000000284 extract Substances 0.000 description 10
• 150000002430 hydrocarbons Chemical group 0.000 description 10
• 150000002440 hydroxy compounds Chemical class 0.000 description 10
• 239000003960 organic solvent Substances 0.000 description 10
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
• 229910052783 alkali metal Inorganic materials 0.000 description 9
• 125000005907 alkyl ester group Chemical group 0.000 description 9
• 238000010438 heat treatment Methods 0.000 description 9
• 230000001590 oxidative effect Effects 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 150000001340 alkali metals Chemical class 0.000 description 8
• 125000004494 ethyl ester group Chemical group 0.000 description 8
• 230000029142 excretion Effects 0.000 description 8
• 230000007062 hydrolysis Effects 0.000 description 8
• 238000006460 hydrolysis reaction Methods 0.000 description 8
• 239000011261 inert gas Substances 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• 239000012429 reaction media Substances 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
• 229920002472 Starch Polymers 0.000 description 7
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 238000001704 evaporation Methods 0.000 description 7
• 230000008020 evaporation Effects 0.000 description 7
• 229930195733 hydrocarbon Natural products 0.000 description 7
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
• 238000007127 saponification reaction Methods 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 159000000000 sodium salts Chemical group 0.000 description 7
• WWOBYPKUYODHDG-UHFFFAOYSA-N 4-chlorocatechol Chemical compound OC1=CC=C(Cl)C=C1O WWOBYPKUYODHDG-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• 241001465754 Metazoa Species 0.000 description 6
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
• 230000002378 acidificating effect Effects 0.000 description 6
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 6
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 239000005457 ice water Substances 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 239000000155 melt Substances 0.000 description 6
• 150000002825 nitriles Chemical class 0.000 description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• 108010010803 Gelatin Proteins 0.000 description 5
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
• 229960000583 acetic acid Drugs 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 239000011230 binding agent Substances 0.000 description 5
• 239000007795 chemical reaction product Substances 0.000 description 5
• 238000000354 decomposition reaction Methods 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 239000011737 fluorine Substances 0.000 description 5
• 239000008273 gelatin Substances 0.000 description 5
• 229920000159 gelatin Polymers 0.000 description 5
• 229940014259 gelatin Drugs 0.000 description 5
• 235000019322 gelatine Nutrition 0.000 description 5
• 235000011852 gelatine desserts Nutrition 0.000 description 5
• 229910052500 inorganic mineral Inorganic materials 0.000 description 5
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
• 235000010755 mineral Nutrition 0.000 description 5
• 239000011707 mineral Substances 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• 229920000137 polyphosphoric acid Polymers 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 235000017281 sodium acetate Nutrition 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 210000002700 urine Anatomy 0.000 description 5
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
• XUZPRGDVRNPODP-UHFFFAOYSA-N 1,2-dimethoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1OC.COC1=CC=C(C)C=C1OC XUZPRGDVRNPODP-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
• 241000282472 Canis lupus familiaris Species 0.000 description 4
• 238000005727 Friedel-Crafts reaction Methods 0.000 description 4
• 241000700159 Rattus Species 0.000 description 4
• 229910021529 ammonia Inorganic materials 0.000 description 4
• JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
• 238000003776 cleavage reaction Methods 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 239000008298 dragée Substances 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 150000002463 imidates Chemical class 0.000 description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 229940098779 methanesulfonic acid Drugs 0.000 description 4
• 230000003647 oxidation Effects 0.000 description 4
• 238000007254 oxidation reaction Methods 0.000 description 4
• 238000005691 oxidative coupling reaction Methods 0.000 description 4
• 239000012071 phase Substances 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 230000007017 scission Effects 0.000 description 4
• 239000008107 starch Substances 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• 150000003455 sulfinic acids Chemical class 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• 238000005809 transesterification reaction Methods 0.000 description 4
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