JPS6019767A

JPS6019767A - カルボスチリル誘導体を有効成分とする抗潰瘍剤

カルボスチリル誘導体を有効成分とする抗潰瘍剤

Info

Publication number: JPS6019767A
Authority: JP; Japan
Prior art keywords: group; compound; reaction; acid; lower alkyl
Prior art date: 1983-07-11
Legal status : Granted

Application number

JP58126498A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0261923B2 (en, 2012

Inventor

Minoru Uchida

内多　稔

Makoto Komatsu

真小松

Kazuyuki Nakagawa

量之中川

Current Assignee

Otsuka Pharmaceutical Co Ltd

Original Assignee

Otsuka Pharmaceutical Co Ltd

Priority date

1983-07-11

Filing date

1983-07-11

Publication date

1985-01-31

1983-07-11 Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd

1983-07-11 Priority to JP58126498A priority Critical patent/JPS6019767A/ja

1985-01-31 Publication of JPS6019767A publication Critical patent/JPS6019767A/ja

1990-12-21 Publication of JPH0261923B2 publication Critical patent/JPH0261923B2/ja

Status Granted legal-status Critical Current

Links

125000005606 carbostyryl group Chemical group 0.000 title description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 84
125000003545 alkoxy group Chemical group 0.000 claims abstract description 54
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 16
125000002947 alkylene group Chemical group 0.000 claims abstract description 9
125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 7
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
125000001424 substituent group Chemical group 0.000 claims description 57
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 43
125000005843 halogen group Chemical group 0.000 claims description 39
210000000988 bone and bone Anatomy 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000003277 amino group Chemical group 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
239000003699 antiulcer agent Substances 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 7
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004946 alkenylalkyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 293
239000003054 catalyst Substances 0.000 abstract description 29
238000006460 hydrolysis reaction Methods 0.000 abstract description 14
238000005886 esterification reaction Methods 0.000 abstract description 9
230000007062 hydrolysis Effects 0.000 abstract description 9
208000025865 Ulcer Diseases 0.000 abstract description 8
238000005917 acylation reaction Methods 0.000 abstract description 8
229910052736 halogen Inorganic materials 0.000 abstract description 8
150000002367 halogens Chemical class 0.000 abstract description 8
231100000397 ulcer Toxicity 0.000 abstract description 8
239000000463 material Substances 0.000 abstract description 7
230000010933 acylation Effects 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 6
125000001589 carboacyl group Chemical group 0.000 abstract description 5
230000032050 esterification Effects 0.000 abstract description 5
PVUZAWYNDBSDTO-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1h-quinolin-3-yl)propanoic acid Chemical compound C=1C2=CC=CC=C2NC(=O)C=1CC(C(=O)O)NC(=O)C1=CC=C(Cl)C=C1 PVUZAWYNDBSDTO-UHFFFAOYSA-N 0.000 abstract description 3
230000001684 chronic effect Effects 0.000 abstract description 3
238000002360 preparation method Methods 0.000 abstract description 3
230000000767 anti-ulcer Effects 0.000 abstract description 2
230000003301 hydrolyzing effect Effects 0.000 abstract description 2
230000003449 preventive effect Effects 0.000 abstract description 2
210000002249 digestive system Anatomy 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 243
-1 and ami7 groups Chemical group 0.000 description 236
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
239000002904 solvent Substances 0.000 description 89
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
235000019441 ethanol Nutrition 0.000 description 71
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 68
239000002253 acid Substances 0.000 description 67
238000003756 stirring Methods 0.000 description 67
239000013078 crystal Substances 0.000 description 66
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 59
238000000034 method Methods 0.000 description 55
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
238000002844 melting Methods 0.000 description 50
230000008018 melting Effects 0.000 description 50
239000000243 solution Substances 0.000 description 50
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 43
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 40
239000003795 chemical substances by application Substances 0.000 description 40
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 39
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 37
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
235000019260 propionic acid Nutrition 0.000 description 34
229940095574 propionic acid Drugs 0.000 description 34
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 34
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
150000001732 carboxylic acid derivatives Chemical class 0.000 description 30
229960001701 chloroform Drugs 0.000 description 30
150000007514 bases Chemical class 0.000 description 28
235000011167 hydrochloric acid Nutrition 0.000 description 28
239000000843 powder Substances 0.000 description 27
235000011121 sodium hydroxide Nutrition 0.000 description 25
239000007858 starting material Substances 0.000 description 25
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
239000000203 mixture Substances 0.000 description 24
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
125000004432 carbon atom Chemical group C* 0.000 description 22
150000002170 ethers Chemical class 0.000 description 22
235000002639 sodium chloride Nutrition 0.000 description 22
238000000354 decomposition reaction Methods 0.000 description 21
150000001298 alcohols Chemical class 0.000 description 20
238000001816 cooling Methods 0.000 description 20
229910000027 potassium carbonate Inorganic materials 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
235000011181 potassium carbonates Nutrition 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
150000007513 acids Chemical class 0.000 description 18
239000011734 sodium Substances 0.000 description 18
229910052708 sodium Inorganic materials 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
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 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
238000010992 reflux Methods 0.000 description 16
239000008096 xylene Substances 0.000 description 16
150000004945 aromatic hydrocarbons Chemical class 0.000 description 15
238000006722 reduction reaction Methods 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
239000007788 liquid Substances 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
229910052782 aluminium Inorganic materials 0.000 description 12
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
235000011118 potassium hydroxide Nutrition 0.000 description 12
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
239000012442 inert solvent Substances 0.000 description 11
229910000029 sodium carbonate Inorganic materials 0.000 description 11
235000017550 sodium carbonate Nutrition 0.000 description 11
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
229960001760 dimethyl sulfoxide Drugs 0.000 description 10
230000002140 halogenating effect Effects 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 10
239000003826 tablet Substances 0.000 description 10
229940086542 triethylamine Drugs 0.000 description 10
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
229910019142 PO4 Inorganic materials 0.000 description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
229920002472 Starch Polymers 0.000 description 9
150000008065 acid anhydrides Chemical class 0.000 description 9
239000003814 drug Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
239000010452 phosphate Substances 0.000 description 9
229920001223 polyethylene glycol Polymers 0.000 description 9
235000015497 potassium bicarbonate Nutrition 0.000 description 9
229910000028 potassium bicarbonate Inorganic materials 0.000 description 9
239000011736 potassium bicarbonate Substances 0.000 description 9
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 9
239000008107 starch Substances 0.000 description 9
235000019698 starch Nutrition 0.000 description 9
239000000126 substance Substances 0.000 description 9
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
229910000147 aluminium phosphate Inorganic materials 0.000 description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
239000003638 chemical reducing agent Substances 0.000 description 8
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 8
150000008282 halocarbons Chemical class 0.000 description 8
239000005457 ice water Substances 0.000 description 8
239000002798 polar solvent Substances 0.000 description 8
230000035484 reaction time Effects 0.000 description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
238000005406 washing Methods 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 7
230000002378 acidificating effect Effects 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 7
150000008044 alkali metal hydroxides Chemical class 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
238000001035 drying Methods 0.000 description 7
150000007529 inorganic bases Chemical class 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
150000007522 mineralic acids Chemical class 0.000 description 7
238000001556 precipitation Methods 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 6
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
239000005711 Benzoic acid Substances 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
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 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
239000002202 Polyethylene glycol Substances 0.000 description 6
229910052776 Thorium Inorganic materials 0.000 description 6
235000010233 benzoic acid Nutrition 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
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 6
239000000839 emulsion Substances 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
239000008101 lactose Substances 0.000 description 6
239000012046 mixed solvent Substances 0.000 description 6
239000012452 mother liquor Substances 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000009467 reduction Effects 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
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