JP2011515390A - 触媒的不斉水素化 - Google Patents
触媒的不斉水素化 Download PDFInfo
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- JP2011515390A JP2011515390A JP2011500723A JP2011500723A JP2011515390A JP 2011515390 A JP2011515390 A JP 2011515390A JP 2011500723 A JP2011500723 A JP 2011500723A JP 2011500723 A JP2011500723 A JP 2011500723A JP 2011515390 A JP2011515390 A JP 2011515390A
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- 238000009876 asymmetric hydrogenation reaction Methods 0.000 title claims abstract description 18
- 230000003197 catalytic effect Effects 0.000 title claims description 6
- 238000000034 method Methods 0.000 claims abstract description 135
- 239000003054 catalyst Substances 0.000 claims abstract description 121
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000001257 hydrogen Substances 0.000 claims abstract description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 62
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 230000008569 process Effects 0.000 claims abstract description 16
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 16
- 150000003624 transition metals Chemical class 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000003446 ligand Substances 0.000 claims description 82
- 238000006243 chemical reaction Methods 0.000 claims description 68
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 50
- 239000000460 chlorine Substances 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- -1 hydroxycarbonyl group Chemical group 0.000 claims description 27
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229940126062 Compound A Drugs 0.000 claims description 18
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- 238000004519 manufacturing process Methods 0.000 claims description 16
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- 239000011737 fluorine Substances 0.000 claims description 15
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- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Natural products CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 8
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 8
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
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- 239000011630 iodine Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
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- 229910006400 μ-Cl Inorganic materials 0.000 claims description 6
- LAXRNWSASWOFOT-UHFFFAOYSA-J (cymene)ruthenium dichloride dimer Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ru+2].[Ru+2].CC(C)C1=CC=C(C)C=C1.CC(C)C1=CC=C(C)C=C1 LAXRNWSASWOFOT-UHFFFAOYSA-J 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910004373 HOAc Inorganic materials 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
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- 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 description 2
- CIZSXHJFJOUTBA-CYBMUJFWSA-N 3-[(3r)-3,4-dihydro-2h-chromen-3-yl]-4-[2-(methylamino)ethyl]-1h-imidazole-2-thione Chemical compound CNCCC1=CNC(=S)N1[C@@H]1CC2=CC=CC=C2OC1 CIZSXHJFJOUTBA-CYBMUJFWSA-N 0.000 claims description 2
- GFTROSXKPGWDQY-GFCCVEGCSA-N 3-[(3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-yl]-4-[2-(methylamino)ethyl]-1h-imidazole-2-thione Chemical compound CNCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2OC1 GFTROSXKPGWDQY-GFCCVEGCSA-N 0.000 claims description 2
- MZPCOQPJUIUTMR-ZDUSSCGKSA-N 4-(2-aminoethyl)-3-[(2s)-1,2,3,4-tetrahydronaphthalen-2-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC=CC=C2CC1 MZPCOQPJUIUTMR-ZDUSSCGKSA-N 0.000 claims description 2
- YSSVPAMNOKPAQE-NSHDSACASA-N 4-(2-aminoethyl)-3-[(2s)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2CC1 YSSVPAMNOKPAQE-NSHDSACASA-N 0.000 claims description 2
- JBMQYQOWXZAPDM-SECBINFHSA-N 4-(2-aminoethyl)-3-[(3r)-6,7,8-trifluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC(C=C(F)C(F)=C2F)=C2OC1 JBMQYQOWXZAPDM-SECBINFHSA-N 0.000 claims description 2
- CWWWTTYMUOYSQA-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2OC1 CWWWTTYMUOYSQA-LLVKDONJSA-N 0.000 claims description 2
- IACPBROODVYPRT-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-6-chloro-8-methoxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound N1([C@@H]2CC=3C=C(Cl)C=C(C=3OC2)OC)C(CCN)=CNC1=S IACPBROODVYPRT-GFCCVEGCSA-N 0.000 claims description 2
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- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XPEYBHVMUUQGFT-OGFXRTJISA-N (3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-amine;hydrochloride Chemical compound Cl.C1=C(F)C=C2C[C@@H](N)COC2=C1F XPEYBHVMUUQGFT-OGFXRTJISA-N 0.000 description 1
- IYWJIYWFPADQAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;ruthenium Chemical compound [Ru].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O IYWJIYWFPADQAN-LNTINUHCSA-N 0.000 description 1
- CKRDOSZCFINPAD-RFVHGSKJSA-N 2-[3-[(3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-yl]-2-sulfanylidene-1h-imidazol-4-yl]ethylazanium;chloride Chemical compound Cl.NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2OC1 CKRDOSZCFINPAD-RFVHGSKJSA-N 0.000 description 1
- FDILNPIPLDMEKH-GFCCVEGCSA-N 3-[(3r)-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-4-[2-(methylamino)ethyl]-1h-imidazole-2-thione Chemical compound CNCCC1=CNC(=S)N1[C@@H]1CC2=CC(O)=CC=C2OC1 FDILNPIPLDMEKH-GFCCVEGCSA-N 0.000 description 1
- VHYPBFDDZNKESQ-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC=CC=C2OC1 VHYPBFDDZNKESQ-GFCCVEGCSA-N 0.000 description 1
- DZRNOQCTKOBUAK-SNVBAGLBSA-N 4-(2-aminoethyl)-3-[(3r)-6,7-difluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=C(F)C=C2OC1 DZRNOQCTKOBUAK-SNVBAGLBSA-N 0.000 description 1
- ZVNPVFPANOYSGK-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-6-fluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC=C2OC1 ZVNPVFPANOYSGK-GFCCVEGCSA-N 0.000 description 1
- LYOMOBDZZKIPDC-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(O)=CC=C2OC1 LYOMOBDZZKIPDC-LLVKDONJSA-N 0.000 description 1
- RWBYHVOPHRDVAI-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-6-nitro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC([N+]([O-])=O)=CC=C2OC1 RWBYHVOPHRDVAI-GFCCVEGCSA-N 0.000 description 1
- MALOQXFHAFIUDC-LBPRGKRZSA-N 4-(3-aminopropyl)-3-[(2s)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]-1h-imidazole-2-thione Chemical compound NCCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2CC1 MALOQXFHAFIUDC-LBPRGKRZSA-N 0.000 description 1
- XIDMCXLNSQNAPP-SECBINFHSA-N 4-(aminomethyl)-3-[(3r)-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCC1=CNC(=S)N1[C@@H]1CC2=CC(O)=CC=C2OC1 XIDMCXLNSQNAPP-SECBINFHSA-N 0.000 description 1
- INYLGVJSDTUSNC-GOSISDBHSA-N 4-[2-(benzylamino)ethyl]-3-[(3r)-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound C=1NC(=S)N([C@H]2COC3=CC=C(C=C3C2)O)C=1CCNCC1=CC=CC=C1 INYLGVJSDTUSNC-GOSISDBHSA-N 0.000 description 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PPZUZWSSIQZIGY-UHFFFAOYSA-N tert-butyl n-[4-[tert-butyl(dimethyl)silyl]oxy-3-oxobutyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC(=O)CO[Si](C)(C)C(C)(C)C PPZUZWSSIQZIGY-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3778408P | 2008-03-19 | 2008-03-19 | |
| US61/037,784 | 2008-03-19 | ||
| PCT/PT2009/000014 WO2009116883A2 (en) | 2008-03-19 | 2009-03-17 | Catalytic asymetric hydrogenation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011515390A true JP2011515390A (ja) | 2011-05-19 |
| JP2011515390A5 JP2011515390A5 (https=) | 2012-05-10 |
Family
ID=40786839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011500723A Pending JP2011515390A (ja) | 2008-03-19 | 2009-03-17 | 触媒的不斉水素化 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8957222B2 (https=) |
| EP (1) | EP2297042B1 (https=) |
| JP (1) | JP2011515390A (https=) |
| KR (1) | KR20110015412A (https=) |
| CN (1) | CN102056846A (https=) |
| AR (1) | AR070935A1 (https=) |
| AU (1) | AU2009226222A1 (https=) |
| BR (1) | BRPI0906174A2 (https=) |
| CA (1) | CA2716694A1 (https=) |
| ES (1) | ES2429120T3 (https=) |
| MX (1) | MX2010010062A (https=) |
| PT (1) | PT2297042E (https=) |
| RU (1) | RU2010142900A (https=) |
| WO (1) | WO2009116883A2 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2297042E (pt) | 2008-03-19 | 2013-10-10 | Bial Portela & Ca Sa | Hidrogenação catalítica assimétrica |
| CA3121743A1 (en) * | 2009-01-15 | 2010-07-22 | Incyte Holdings Corporation | Processes for preparing jak inhibitors and related intermediate compounds |
| CN106977486B (zh) * | 2017-05-25 | 2019-09-24 | 南方科技大学 | 一种手性二氢黄酮类化合物及其衍生物的制备方法和应用 |
| CN110841720B (zh) * | 2019-11-29 | 2022-11-18 | 河南师范大学 | 石墨烯吸附多组分手性催化剂及其在不对称氢化中的应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003509513A (ja) * | 1999-09-20 | 2003-03-11 | ザ ペン ステイト リサーチ ファンデーション | キラルホスフィン、その遷移金属錯体および不斉反応でのその使用 |
| JP2004513950A (ja) * | 2000-11-17 | 2004-05-13 | ザ ペン ステイト リサーチ ファンデーション | オルト置換キラルホスフィンおよびホスフィナイトならびに非対称触媒反応でのその使用 |
| JP2006507261A (ja) * | 2002-10-11 | 2006-03-02 | ポルテラ・アンド・シーエー・エスエー | ドーパミン−ベータ−ヒドロキシラーゼの末梢選択的阻害剤としてのイミダゾール誘導体、及びこれらの用途 |
| JP5372771B2 (ja) * | 2006-12-12 | 2013-12-18 | ビアル−ポルテア アンド シー．エイ．， エス．エイ． | プロセス |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5144050A (en) | 1991-10-01 | 1992-09-01 | Monsanto Company | Ruthenium(II)-BINAP diketonate complexes |
| PT2297042E (pt) | 2008-03-19 | 2013-10-10 | Bial Portela & Ca Sa | Hidrogenação catalítica assimétrica |
-
2009
- 2009-03-17 PT PT09721339T patent/PT2297042E/pt unknown
- 2009-03-17 WO PCT/PT2009/000014 patent/WO2009116883A2/en not_active Ceased
- 2009-03-17 MX MX2010010062A patent/MX2010010062A/es not_active Application Discontinuation
- 2009-03-17 JP JP2011500723A patent/JP2011515390A/ja active Pending
- 2009-03-17 CA CA2716694A patent/CA2716694A1/en not_active Abandoned
- 2009-03-17 CN CN2009801095330A patent/CN102056846A/zh active Pending
- 2009-03-17 ES ES09721339T patent/ES2429120T3/es active Active
- 2009-03-17 US US12/921,966 patent/US8957222B2/en not_active Expired - Fee Related
- 2009-03-17 RU RU2010142900/05A patent/RU2010142900A/ru not_active Application Discontinuation
- 2009-03-17 AU AU2009226222A patent/AU2009226222A1/en not_active Abandoned
- 2009-03-17 EP EP09721339.1A patent/EP2297042B1/en not_active Not-in-force
- 2009-03-17 KR KR1020107023164A patent/KR20110015412A/ko not_active Withdrawn
- 2009-03-18 AR ARP090100969 patent/AR070935A1/es unknown
- 2009-09-17 BR BRPI0906174-6A patent/BRPI0906174A2/pt not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003509513A (ja) * | 1999-09-20 | 2003-03-11 | ザ ペン ステイト リサーチ ファンデーション | キラルホスフィン、その遷移金属錯体および不斉反応でのその使用 |
| JP2004513950A (ja) * | 2000-11-17 | 2004-05-13 | ザ ペン ステイト リサーチ ファンデーション | オルト置換キラルホスフィンおよびホスフィナイトならびに非対称触媒反応でのその使用 |
| JP2006507261A (ja) * | 2002-10-11 | 2006-03-02 | ポルテラ・アンド・シーエー・エスエー | ドーパミン−ベータ−ヒドロキシラーゼの末梢選択的阻害剤としてのイミダゾール誘導体、及びこれらの用途 |
| JP5372771B2 (ja) * | 2006-12-12 | 2013-12-18 | ビアル−ポルテア アンド シー．エイ．， エス．エイ． | プロセス |
Non-Patent Citations (3)
| Title |
|---|
| PHILIPPE DUPAU，ET AL.: ""Direct preparation of N-(Alk-1-en-1-yl)carbamates from cyclic ketones and unsubstituted carbamates"", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, vol. 67, no. 2, JPN7013000515, 2002, pages 235 - 244, XP009098514, ISSN: 0002693323, DOI: 10.1135/cccc20020235 * |
| PHILIPPE DUPAU，ET AL.: ""New route to optically active amine derivatives: rutheniumcatalyzed enantioselective hydrogenation", TETRAHEDRON: ASYMMETRY, vol. 10, no. 18, JPN5011010973, 1999, pages 3467 - 3471, XP002476034, ISSN: 0002693321, DOI: 10.1016/S0957-4166(99)00375-4 * |
| PHILIPPE DUPAU，ET AL.: ""Synthesis of optically active 2-aminotetralin derivatives via enantioselective ruthenium-catalyzed", TETRAHEDRON: ASYMMETRY, vol. 12, no. 6, JPN6013006460, 2001, pages 863 - 867, ISSN: 0002693322 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2429120T3 (es) | 2013-11-13 |
| KR20110015412A (ko) | 2011-02-15 |
| CA2716694A1 (en) | 2009-09-24 |
| WO2009116883A8 (en) | 2009-12-10 |
| WO2009116883A3 (en) | 2010-04-01 |
| WO2009116883A2 (en) | 2009-09-24 |
| US8957222B2 (en) | 2015-02-17 |
| AR070935A1 (es) | 2010-05-12 |
| BRPI0906174A2 (pt) | 2015-06-30 |
| PT2297042E (pt) | 2013-10-10 |
| AU2009226222A1 (en) | 2009-09-24 |
| RU2010142900A (ru) | 2012-04-27 |
| EP2297042A2 (en) | 2011-03-23 |
| MX2010010062A (es) | 2010-09-30 |
| EP2297042B1 (en) | 2013-07-10 |
| CN102056846A (zh) | 2011-05-11 |
| US20110112303A1 (en) | 2011-05-12 |
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