JP2012513966A - 水素移動反応を使用する光学活性化合物の調製の方法 - Google Patents
水素移動反応を使用する光学活性化合物の調製の方法 Download PDFInfo
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- JP2012513966A JP2012513966A JP2011542822A JP2011542822A JP2012513966A JP 2012513966 A JP2012513966 A JP 2012513966A JP 2011542822 A JP2011542822 A JP 2011542822A JP 2011542822 A JP2011542822 A JP 2011542822A JP 2012513966 A JP2012513966 A JP 2012513966A
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- Prior art keywords
- ethyl
- phenol
- compound
- compound according
- dimethylamino
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 107
- 238000000034 method Methods 0.000 title claims abstract description 73
- 239000001257 hydrogen Substances 0.000 title claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 33
- 238000006276 transfer reaction Methods 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 title claims abstract 12
- 230000008569 process Effects 0.000 title claims description 18
- GQZXRLWUYONVCP-QMMMGPOBSA-N 3-[(1s)-1-(dimethylamino)ethyl]phenol Chemical compound CN(C)[C@@H](C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-QMMMGPOBSA-N 0.000 claims abstract description 49
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims abstract description 47
- 238000010531 catalytic reduction reaction Methods 0.000 claims abstract description 29
- 229950010673 rivastigmine hydrogen tartrate Drugs 0.000 claims abstract description 14
- GWHQHAUAXRMMOT-MBANBULQSA-N rivastigmine tartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 GWHQHAUAXRMMOT-MBANBULQSA-N 0.000 claims abstract description 13
- 229960004323 rivastigmine tartrate Drugs 0.000 claims abstract description 5
- COJRWHSKVYUZHQ-ZCFIWIBFSA-N 3-[(1r)-1-hydroxyethyl]phenol Chemical compound C[C@@H](O)C1=CC=CC(O)=C1 COJRWHSKVYUZHQ-ZCFIWIBFSA-N 0.000 claims description 52
- 239000003054 catalyst Substances 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 claims description 40
- 229960004136 rivastigmine Drugs 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 31
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000002425 crystallisation Methods 0.000 claims description 23
- 230000008025 crystallization Effects 0.000 claims description 23
- -1 tetrafluoroborate Chemical compound 0.000 claims description 22
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 21
- 230000001476 alcoholic effect Effects 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- 150000004820 halides Chemical class 0.000 claims description 17
- 229910052723 transition metal Inorganic materials 0.000 claims description 17
- 150000003624 transition metals Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 9
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 8
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 8
- 150000001414 amino alcohols Chemical class 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 230000003213 activating effect Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 238000012377 drug delivery Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 230000006103 sulfonylation Effects 0.000 claims description 6
- 238000005694 sulfonylation reaction Methods 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- CLPXHEDITUKVCC-UHFFFAOYSA-K 1-methyl-4-propan-2-ylbenzene;trichlororuthenium Chemical class Cl[Ru](Cl)Cl.CC(C)C1=CC=C(C)C=C1 CLPXHEDITUKVCC-UHFFFAOYSA-K 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- WAPZHQZXWPVDMP-MRVPVSSYSA-N [3-[(1r)-1-methylsulfonyloxyethyl]phenyl] methanesulfonate Chemical compound CS(=O)(=O)O[C@H](C)C1=CC=CC(OS(C)(=O)=O)=C1 WAPZHQZXWPVDMP-MRVPVSSYSA-N 0.000 claims description 4
- CZCQMRZQDWWULM-VIFPVBQESA-N [3-[(1s)-1-(dimethylamino)ethyl]phenyl] methanesulfonate Chemical compound CN(C)[C@@H](C)C1=CC=CC(OS(C)(=O)=O)=C1 CZCQMRZQDWWULM-VIFPVBQESA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- UOPFIWYXBIHPIP-NHCUHLMSSA-N n-[(1r,2r)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@H](C=1C=CC=CC=1)[C@H](N)C1=CC=CC=C1 UOPFIWYXBIHPIP-NHCUHLMSSA-N 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 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
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical compound C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- KMJTTWREVXZPTK-UHFFFAOYSA-M n-ethyl-n-methylcarbamate Chemical compound CCN(C)C([O-])=O KMJTTWREVXZPTK-UHFFFAOYSA-M 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- VPLSOSGETUGSOD-GRHHLOCNSA-N CN([C@@H](C)C=1C=C(C=CC1)O)C.CN([C@@H](C)C=1C=C(C=CC1)O)C Chemical compound CN([C@@H](C)C=1C=C(C=CC1)O)C.CN([C@@H](C)C=1C=C(C=CC1)O)C VPLSOSGETUGSOD-GRHHLOCNSA-N 0.000 claims 5
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 1
- ZUOFYVXFZNJPND-ZETCQYMHSA-N C[C@@H](C1=CC=CC(=C1)CS(=O)(=O)O)O Chemical compound C[C@@H](C1=CC=CC(=C1)CS(=O)(=O)O)O ZUOFYVXFZNJPND-ZETCQYMHSA-N 0.000 claims 1
- ZUOFYVXFZNJPND-SSDOTTSWSA-N C[C@H](C1=CC=CC(=C1)CS(=O)(=O)O)O Chemical compound C[C@H](C1=CC=CC(=C1)CS(=O)(=O)O)O ZUOFYVXFZNJPND-SSDOTTSWSA-N 0.000 claims 1
- NPYAZCQPWJLMFH-SSDOTTSWSA-N C[C@H](CS(=O)(=O)O)C1=CC(=CC=C1)O Chemical compound C[C@H](CS(=O)(=O)O)C1=CC(=CC=C1)O NPYAZCQPWJLMFH-SSDOTTSWSA-N 0.000 claims 1
- KORBNZMNKRINHE-SSDOTTSWSA-N [(1r)-1-(3-hydroxyphenyl)ethyl] methanesulfonate Chemical compound CS(=O)(=O)O[C@H](C)C1=CC=CC(O)=C1 KORBNZMNKRINHE-SSDOTTSWSA-N 0.000 claims 1
- CZCQMRZQDWWULM-SECBINFHSA-N [3-[(1r)-1-(dimethylamino)ethyl]phenyl] methanesulfonate Chemical compound CN(C)[C@H](C)C1=CC=CC(OS(C)(=O)=O)=C1 CZCQMRZQDWWULM-SECBINFHSA-N 0.000 claims 1
- WAPZHQZXWPVDMP-QMMMGPOBSA-N [3-[(1s)-1-methylsulfonyloxyethyl]phenyl] methanesulfonate Chemical compound CS(=O)(=O)O[C@@H](C)C1=CC=CC(OS(C)(=O)=O)=C1 WAPZHQZXWPVDMP-QMMMGPOBSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000012566 active pharmaceutical ingredient starting material Substances 0.000 claims 1
- 229940125363 active pharmaceutical ingredient starting material Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 239000008186 active pharmaceutical agent Substances 0.000 abstract description 9
- 229940088679 drug related substance Drugs 0.000 abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 150000002431 hydrogen Chemical class 0.000 description 21
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
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- 150000002009 diols Chemical class 0.000 description 11
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- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 238000006722 reduction reaction Methods 0.000 description 6
- CZCQMRZQDWWULM-UHFFFAOYSA-N [3-[1-(dimethylamino)ethyl]phenyl] methanesulfonate Chemical compound CN(C)C(C)C1=CC=CC(OS(C)(=O)=O)=C1 CZCQMRZQDWWULM-UHFFFAOYSA-N 0.000 description 5
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- KORBNZMNKRINHE-UHFFFAOYSA-N 1-(3-hydroxyphenyl)ethyl methanesulfonate Chemical compound CS(=O)(=O)OC(C)C1=CC=CC(O)=C1 KORBNZMNKRINHE-UHFFFAOYSA-N 0.000 description 4
- GQZXRLWUYONVCP-UHFFFAOYSA-N 3-[1-(dimethylamino)ethyl]phenol Chemical compound CN(C)C(C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- WAPZHQZXWPVDMP-UHFFFAOYSA-N [3-(1-methylsulfonyloxyethyl)phenyl] methanesulfonate Chemical compound CS(=O)(=O)OC(C)C1=CC=CC(OS(C)(=O)=O)=C1 WAPZHQZXWPVDMP-UHFFFAOYSA-N 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
- COJRWHSKVYUZHQ-UHFFFAOYSA-N 3-(1-hydroxyethyl)phenol Chemical compound CC(O)C1=CC=CC(O)=C1 COJRWHSKVYUZHQ-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
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- QMPSUPWBJMOGPS-UHFFFAOYSA-N [Ru].CC(C)C1=CC=C(C)C=C1 Chemical compound [Ru].CC(C)C1=CC=C(C)C=C1 QMPSUPWBJMOGPS-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
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- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
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- ZDKRMIJRCHPKLW-UHFFFAOYSA-N benzyl methanesulfonate Chemical group CS(=O)(=O)OCC1=CC=CC=C1 ZDKRMIJRCHPKLW-UHFFFAOYSA-N 0.000 description 1
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- 238000006555 catalytic reaction Methods 0.000 description 1
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- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 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 1
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
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- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isopropylhexane Natural products CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
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- 238000011916 stereoselective reduction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/11—Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hospice & Palliative Care (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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| GBGB0823554.1A GB0823554D0 (en) | 2008-12-24 | 2008-12-24 | Process for the preparation of optically active compounds using transfer hydrogenation |
| GB0823554.1 | 2008-12-24 | ||
| PCT/EP2009/067821 WO2010072798A1 (en) | 2008-12-24 | 2009-12-23 | Process for the preparation of optically active compounds using transfer hydrogenation |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2014200094A1 (ja) * | 2013-06-14 | 2014-12-18 | 日産化学工業株式会社 | 光学活性アルコール化合物の製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193600B (zh) * | 2012-01-07 | 2016-04-06 | 浙江九洲药物科技有限公司 | 卡巴拉汀中间体的制备方法 |
| CN103980270A (zh) * | 2014-05-19 | 2014-08-13 | 埃斯特维华义制药有限公司 | 一种（r）-3-奎宁醇的制备方法 |
| CN108752322A (zh) * | 2018-09-12 | 2018-11-06 | 广州新民培林医药科技有限公司 | 一种新型Tepotinib衍生物和制备方法及其在抗肿瘤药物中的应用 |
| CN109809967B (zh) * | 2019-03-04 | 2022-03-18 | 陕西师范大学 | 一种合成手性醇的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02235A (ja) * | 1987-11-25 | 1990-01-05 | Eli Lilly & Co | セロトニンおよびノルエピネフリン摂取阻害剤 |
| JPH0899940A (ja) * | 1994-09-30 | 1996-04-16 | Kanegafuchi Chem Ind Co Ltd | 光学活性な１−（３，４−ジメトキシフェニル）−２−アミノプロパンの製造法 |
| JPH09165362A (ja) * | 1987-03-04 | 1997-06-24 | Sandoz Ag | フェニルカルバメート |
| JP2001294568A (ja) * | 2000-04-13 | 2001-10-23 | Central Glass Co Ltd | 光学活性α−メチル−ビス−３、５−（トリフルオロメチル）ベンジルアミンの製造方法 |
| WO2005058804A1 (en) * | 2003-12-18 | 2005-06-30 | Avecia Pharmaceuticals Limited | Process for the preparation of tertiary amines attached to a secondary carbon centre |
| WO2005092825A1 (ja) * | 2004-03-29 | 2005-10-06 | Nagoya Industrial Science Research Institute | 光学活性アルコールの製法 |
| WO2006137195A1 (ja) * | 2005-06-20 | 2006-12-28 | Kanto Kagaku Kabushiki Kaisha | スルホナート触媒及びそれを利用したアルコール化合物の製法 |
| JP2008504260A (ja) * | 2004-06-25 | 2008-02-14 | イーストマン ケミカル カンパニー | ホスフィン−アミノホスフィン配位子のルテニウム錯体 |
| JP2008519023A (ja) * | 2004-11-08 | 2008-06-05 | エムキュア ファーマシューティカルズ リミテッド | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
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| DE602004017747D1 (de) * | 2003-07-08 | 2008-12-24 | Unilever Nv | Verfahren zur herstellung einer kosmetisch aktiven verbindung |
| TWI389709B (zh) | 2005-12-01 | 2013-03-21 | Novartis Ag | 經皮治療系統 |
| WO2007147897A1 (de) | 2006-06-23 | 2007-12-27 | Basf Se | Verfahren zur herstellung von optisch aktiven 2-halogen-1-phenylethanol-derivaten und folgeprodukten davon |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2014200094A1 (ja) * | 2013-06-14 | 2014-12-18 | 日産化学工業株式会社 | 光学活性アルコール化合物の製造方法 |
| JPWO2014200094A1 (ja) * | 2013-06-14 | 2017-02-23 | 日産化学工業株式会社 | 光学活性アルコール化合物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CO6382153A2 (es) | 2012-02-15 |
| SG172052A1 (en) | 2011-07-28 |
| CL2011001563A1 (es) | 2012-01-13 |
| US8415508B2 (en) | 2013-04-09 |
| ECSP11011221A (es) | 2011-08-31 |
| WO2010072798A1 (en) | 2010-07-01 |
| NZ593493A (en) | 2013-03-28 |
| MY151103A (en) | 2014-04-15 |
| US8637713B2 (en) | 2014-01-28 |
| EP2382172A1 (en) | 2011-11-02 |
| US20100168229A1 (en) | 2010-07-01 |
| TN2011000290A1 (en) | 2012-12-17 |
| MA32983B1 (fr) | 2012-01-02 |
| AU2009331493B2 (en) | 2013-03-07 |
| KR20110098964A (ko) | 2011-09-02 |
| BRPI0923394A2 (pt) | 2016-01-12 |
| AU2009331493A1 (en) | 2011-07-07 |
| MX2011006918A (es) | 2011-07-29 |
| US20130096337A1 (en) | 2013-04-18 |
| IL213520A0 (en) | 2011-07-31 |
| CN102264672A (zh) | 2011-11-30 |
| GB0823554D0 (en) | 2009-01-28 |
| CA2748349A1 (en) | 2010-07-01 |
| AR075496A1 (es) | 2011-04-06 |
| TW201035028A (en) | 2010-10-01 |
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