JP2002513003A - 置換ビピリジル誘導体の触媒的製造法 - Google Patents
置換ビピリジル誘導体の触媒的製造法Info
- Publication number
- JP2002513003A JP2002513003A JP2000545835A JP2000545835A JP2002513003A JP 2002513003 A JP2002513003 A JP 2002513003A JP 2000545835 A JP2000545835 A JP 2000545835A JP 2000545835 A JP2000545835 A JP 2000545835A JP 2002513003 A JP2002513003 A JP 2002513003A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cation
- aryl
- coo
- optionally
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims description 5
- 230000003197 catalytic effect Effects 0.000 title description 3
- 150000001768 cations Chemical class 0.000 claims abstract description 115
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 93
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 46
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 12
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 41
- -1 methoxy, acetoxy Chemical group 0.000 claims description 41
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052700 potassium Inorganic materials 0.000 claims description 18
- 229910052708 sodium Inorganic materials 0.000 claims description 18
- 239000011734 sodium Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 13
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 150000005748 halopyridines Chemical class 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- FXPLCAKVOYHAJA-UHFFFAOYSA-N 2-(4-carboxypyridin-2-yl)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(C=2N=CC=C(C=2)C(O)=O)=C1 FXPLCAKVOYHAJA-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 150000005749 2-halopyridines Chemical class 0.000 claims description 3
- 150000005751 4-halopyridines Chemical class 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 238000005575 aldol reaction Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims description 2
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 102100038239 Protein Churchill Human genes 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 238000005868 electrolysis reaction Methods 0.000 claims description 2
- 125000006377 halopyridyl group Chemical group 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002941 palladium compounds Chemical class 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 2
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 239000012043 crude product Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 230000020477 pH reduction Effects 0.000 description 5
- KVQMUHHSWICEIH-UHFFFAOYSA-N 6-(5-carboxypyridin-2-yl)pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=N1 KVQMUHHSWICEIH-UHFFFAOYSA-N 0.000 description 4
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 4
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 3
- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 3
- UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000004424 polypyridyl Polymers 0.000 description 3
- CCZWSTFVHJPCEM-UHFFFAOYSA-N 2-iodopyridine Chemical compound IC1=CC=CC=N1 CCZWSTFVHJPCEM-UHFFFAOYSA-N 0.000 description 2
- OHJPGUSXUGHOGE-UHFFFAOYSA-N 2-methyl-6-(6-methylpyridin-2-yl)pyridine Chemical group CC1=CC=CC(C=2N=C(C)C=CC=2)=N1 OHJPGUSXUGHOGE-UHFFFAOYSA-N 0.000 description 2
- WPTCSQBWLUUYDV-UHFFFAOYSA-N 2-quinolin-2-ylquinoline Chemical compound C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3)=CC=C21 WPTCSQBWLUUYDV-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- UPSIFZLGCWKSOQ-UHFFFAOYSA-N 6-(6-oxo-1H-pyridin-2-yl)-1H-pyridin-2-one Chemical compound OC1=CC=CC(C=2N=C(O)C=CC=2)=N1.OC1=CC=CC(C=2N=C(O)C=CC=2)=N1 UPSIFZLGCWKSOQ-UHFFFAOYSA-N 0.000 description 2
- CLNNBQDAAGDAHI-UHFFFAOYSA-N 6-chloro-1h-pyridin-2-one Chemical compound OC1=CC=CC(Cl)=N1 CLNNBQDAAGDAHI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- SQSYNRCXIZHKAI-UHFFFAOYSA-N 2,6-dichloroisonicotinic acid Chemical compound OC(=O)C1=CC(Cl)=NC(Cl)=C1 SQSYNRCXIZHKAI-UHFFFAOYSA-N 0.000 description 1
- KNVZVRWMLMPTTJ-UHFFFAOYSA-N 2-(3-carboxy-2-pyridinyl)-3-pyridinecarboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C1=NC=CC=C1C(O)=O KNVZVRWMLMPTTJ-UHFFFAOYSA-N 0.000 description 1
- RJNRKZBHLCOHNM-UHFFFAOYSA-N 2-(3-hydroxypyridin-2-yl)pyridin-3-ol Chemical group OC1=CC=CN=C1C1=NC=CC=C1O RJNRKZBHLCOHNM-UHFFFAOYSA-N 0.000 description 1
- PJJJKQDSKZSCHJ-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)quinolin-3-ol Chemical compound C1=CC=C2C=C(O)C(C3=NC4=CC=CC=C4C=C3O)=NC2=C1 PJJJKQDSKZSCHJ-UHFFFAOYSA-N 0.000 description 1
- ZZTDEFHCSZAWMD-UHFFFAOYSA-L 2-(4-carboxylatopyridin-2-yl)pyridine-4-carboxylate;ruthenium(2+) Chemical compound [Ru+2].[O-]C(=O)C1=CC=NC(C=2N=CC=C(C=2)C([O-])=O)=C1 ZZTDEFHCSZAWMD-UHFFFAOYSA-L 0.000 description 1
- ZXGHKJHRHVDMSW-UHFFFAOYSA-N 2-chloro-5-methoxypyridine Chemical compound COC1=CC=C(Cl)N=C1 ZXGHKJHRHVDMSW-UHFFFAOYSA-N 0.000 description 1
- GXZDYRYYNXYPMQ-UHFFFAOYSA-N 2-chloro-6-methylpyridine Chemical compound CC1=CC=CC(Cl)=N1 GXZDYRYYNXYPMQ-UHFFFAOYSA-N 0.000 description 1
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 1
- QXCOHSRHFCHCHN-UHFFFAOYSA-N 2-chloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(Cl)=C1 QXCOHSRHFCHCHN-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- PORGLLGXCAQORO-UHFFFAOYSA-N 3-bromo-2-methoxypyridine Chemical compound COC1=NC=CC=C1Br PORGLLGXCAQORO-UHFFFAOYSA-N 0.000 description 1
- 150000005750 3-halopyridines Chemical class 0.000 description 1
- AKQKGGMCVOUUOQ-UHFFFAOYSA-N 3-methoxy-2-(3-methoxypyridin-2-yl)pyridine Chemical group COC1=CC=CN=C1C1=NC=CC=C1OC AKQKGGMCVOUUOQ-UHFFFAOYSA-N 0.000 description 1
- GALLWSLKCWDSLT-UHFFFAOYSA-N 3-methyl-2-(3-methylpyridin-2-yl)pyridine Chemical group CC1=CC=CN=C1C1=NC=CC=C1C GALLWSLKCWDSLT-UHFFFAOYSA-N 0.000 description 1
- OFDVABAUFQJWEZ-UHFFFAOYSA-N 3-pyridin-3-ylpyridine Chemical group C1=CN=CC(C=2C=NC=CC=2)=C1 OFDVABAUFQJWEZ-UHFFFAOYSA-N 0.000 description 1
- SZFUWUOHDRMCKD-UHFFFAOYSA-N 5-chloro-1h-pyridin-2-one Chemical compound OC1=CC=C(Cl)C=N1 SZFUWUOHDRMCKD-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- SSMVCDQYAUQQDQ-UHFFFAOYSA-N BrC1=NC(=CC=C1)C.BrC1=NC(=CC=C1)C Chemical compound BrC1=NC(=CC=C1)C.BrC1=NC(=CC=C1)C SSMVCDQYAUQQDQ-UHFFFAOYSA-N 0.000 description 1
- INCMGKKMSQNIOX-UHFFFAOYSA-N C1=CNC(C=C1C(=O)O)(Cl)Cl Chemical compound C1=CNC(C=C1C(=O)O)(Cl)Cl INCMGKKMSQNIOX-UHFFFAOYSA-N 0.000 description 1
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 0.000 description 1
- 241000282346 Meles meles Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000005752 bromopyridines Chemical class 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000013462 industrial intermediate Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- YTXAYGAYACWVGD-UHFFFAOYSA-N palladium;hydrate Chemical compound O.[Pd] YTXAYGAYACWVGD-UHFFFAOYSA-N 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006456 reductive dimerization reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/04—Substitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19819010 | 1998-04-29 | ||
| DE19819010.7 | 1998-04-29 | ||
| PCT/EP1999/002788 WO1999055675A1 (de) | 1998-04-29 | 1999-04-24 | Verfahren zur katalytischen herstellung von substituierten bipyridylderivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002513003A true JP2002513003A (ja) | 2002-05-08 |
| JP2002513003A5 JP2002513003A5 (enExample) | 2006-07-06 |
Family
ID=7866073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000545835A Ceased JP2002513003A (ja) | 1998-04-29 | 1999-04-24 | 置換ビピリジル誘導体の触媒的製造法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6500956B1 (enExample) |
| EP (1) | EP1076648B1 (enExample) |
| JP (1) | JP2002513003A (enExample) |
| KR (1) | KR100592699B1 (enExample) |
| CN (1) | CN1111523C (enExample) |
| DE (1) | DE59913665D1 (enExample) |
| WO (1) | WO1999055675A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005225834A (ja) * | 2004-02-16 | 2005-08-25 | Tosoh Corp | ２，２’−ビピリジル化合物およびその製造方法 |
| JP2006206516A (ja) * | 2005-01-28 | 2006-08-10 | Koei Chem Co Ltd | ４，４’−ジカルボキシ−２，２’−ビピリジンの製造方法 |
| JP2006240997A (ja) * | 2005-02-28 | 2006-09-14 | Koei Chem Co Ltd | ビピリジン類の製造方法 |
| JPWO2005073156A1 (ja) * | 2004-01-30 | 2007-09-06 | 独立行政法人科学技術振興機構 | 光学活性ヒドロキシメチル化化合物の製法 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002105346A (ja) * | 2000-07-25 | 2002-04-10 | Fuji Photo Film Co Ltd | 金属錯体色素、光電変換素子および光電池 |
| US7319107B2 (en) * | 2001-11-08 | 2008-01-15 | Johnson & Johnson Consumer Companies, Inc. | 1,2,4-thiadiazolium derivatives as melanocortin receptor modulators |
| NZ532883A (en) | 2001-11-08 | 2007-09-28 | Ortho Mcneil Pharm Inc | Novel 1,2,4-thiadiazole derivatives as melanocortin receptor modulators |
| GB0221443D0 (en) | 2002-09-16 | 2002-10-23 | Glaxo Group Ltd | Pyridine derivates |
| RU2249476C2 (ru) * | 2003-04-22 | 2005-04-10 | Государственное унитарное предприятие научно-исследовательский Институт по повышению нефтеотдачи пластов Академии наук республики Башкортостан | Катализатор для получения 2,3-диалкилхинолинов |
| CA2580855A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| CN101084212A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶介导剂的用途 |
| MX2007003319A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| TW200626138A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| CA2580857A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| MX2007003318A (es) | 2004-09-20 | 2007-05-18 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| EP2029138A1 (en) | 2005-06-03 | 2009-03-04 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| AU2006275403A1 (en) * | 2005-08-02 | 2007-02-08 | Lexicon Pharmaceuticals, Inc. | 2-aminoaryl pyridines as protein kinases inhibitors |
| US8247453B2 (en) | 2008-02-21 | 2012-08-21 | Janssen Pharmaceutica, Nv | Methods for the treatment of dermatological disorders |
| JP2012524814A (ja) * | 2009-04-24 | 2012-10-18 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | １，２，４−チアジアゾール誘導体の安定的な局所組成物 |
| CN103183636A (zh) * | 2013-04-05 | 2013-07-03 | 浙江大学 | 一种合成2,2’-联吡啶-4,4’-二甲酸的新方法 |
| CN105481761B (zh) * | 2015-11-23 | 2018-08-31 | 安徽千和新材料科技发展有限公司 | 一种2,2’-联吡啶的钯/碳催化制备方法 |
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| JPS4814672B1 (enExample) * | 1970-02-23 | 1973-05-09 | ||
| JPH01220380A (ja) * | 1988-02-12 | 1989-09-04 | Gebr Sulzer Ag | 光電気化学電池・その製法及び使用法 |
| JPH05504023A (ja) * | 1990-04-17 | 1993-06-24 | エコール・ポリテクニツク・フエデラール・ドウ・ローザンヌ | 光電池 |
| JPH07508537A (ja) * | 1993-04-21 | 1995-09-21 | イーストマン コダック カンパニー | イオン感受性化合物 |
| JPH1025342A (ja) * | 1996-07-11 | 1998-01-27 | Mitsubishi Heavy Ind Ltd | 光機能性重合体組成物及びその製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE2030562C3 (de) * | 1970-06-20 | 1975-08-07 | Daimler-Benz Ag, 7000 Stuttgart | Vorrichtung zum Befestigen eines Kommandolautsprechers od.dgl. auf einem Fahrzeugdach |
| GB1340006A (en) * | 1971-06-24 | 1973-12-05 | Ici Ltd | Manufacture of bipyridyls |
| GB8515063D0 (en) * | 1985-06-14 | 1985-07-17 | Ici Plc | Polyaromatic compounds |
-
1999
- 1999-04-24 EP EP99920777A patent/EP1076648B1/de not_active Expired - Lifetime
- 1999-04-24 US US09/674,063 patent/US6500956B1/en not_active Expired - Fee Related
- 1999-04-24 DE DE59913665T patent/DE59913665D1/de not_active Expired - Lifetime
- 1999-04-24 CN CN99805552A patent/CN1111523C/zh not_active Expired - Fee Related
- 1999-04-24 WO PCT/EP1999/002788 patent/WO1999055675A1/de not_active Ceased
- 1999-04-24 JP JP2000545835A patent/JP2002513003A/ja not_active Ceased
- 1999-04-24 KR KR1020007012015A patent/KR100592699B1/ko not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS4814672B1 (enExample) * | 1970-02-23 | 1973-05-09 | ||
| JPH01220380A (ja) * | 1988-02-12 | 1989-09-04 | Gebr Sulzer Ag | 光電気化学電池・その製法及び使用法 |
| JPH05504023A (ja) * | 1990-04-17 | 1993-06-24 | エコール・ポリテクニツク・フエデラール・ドウ・ローザンヌ | 光電池 |
| JPH07508537A (ja) * | 1993-04-21 | 1995-09-21 | イーストマン コダック カンパニー | イオン感受性化合物 |
| JPH1025342A (ja) * | 1996-07-11 | 1998-01-27 | Mitsubishi Heavy Ind Ltd | 光機能性重合体組成物及びその製造方法 |
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| JPN7010001653, ＣＯＮＳＴＡＢＬＥ，Ｅ．Ｃ． ｅｔ ａｌ, "Ｆｕｎｃｔｉｏｎａｌｉｓｅｄ ３，３’−ｂｉｐｙｒｉｄｉｎｅｓ−ａ ｎｅｗ ｃｌａｓｓ ｏｆ ｄｉｎｕｃｌｅａｔｉｎｇ ｌｉｇａｎｄｓ", Ｎｅｗ Ｊｏｕｒｎａｌ ｏｆ Ｃｈｅｍｉｓｔｒｙ, 1998, Ｖｏｌ．２２， Ｎｏ．３, ｐ．２８７−２９４ * |
| JPN7010001654, ＢＡＲＯＮＥ，Ｖ． ｅｔ ａｌ, "Ａ ｔｈｅｏｒｅｔｉｃａｌ ｓｔｕｄｙ ｏｆ ｐｒｏｔｏｎ ｔｒａｎｓｆｅｒ ｉｎ ［２，２’−ｂｉｐｙｒｉｄｙｌ］−３，３’−ｄｉｏｌ", Ｃｈｅｍｉｃａｌ Ｐｈｙｓｉｃｓ Ｌｅｔｔｅｒｓ, 1995, Ｖｏｌ．２４１， Ｎｏ．１，２, ｐ．１−６ * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005073156A1 (ja) * | 2004-01-30 | 2007-09-06 | 独立行政法人科学技術振興機構 | 光学活性ヒドロキシメチル化化合物の製法 |
| JP4582794B2 (ja) * | 2004-01-30 | 2010-11-17 | 独立行政法人科学技術振興機構 | 光学活性ヒドロキシメチル化化合物の製法 |
| JP2005225834A (ja) * | 2004-02-16 | 2005-08-25 | Tosoh Corp | ２，２’−ビピリジル化合物およびその製造方法 |
| JP2006206516A (ja) * | 2005-01-28 | 2006-08-10 | Koei Chem Co Ltd | ４，４’−ジカルボキシ−２，２’−ビピリジンの製造方法 |
| JP2006240997A (ja) * | 2005-02-28 | 2006-09-14 | Koei Chem Co Ltd | ビピリジン類の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6500956B1 (en) | 2002-12-31 |
| EP1076648A1 (de) | 2001-02-21 |
| CN1111523C (zh) | 2003-06-18 |
| KR100592699B1 (ko) | 2006-06-26 |
| KR20010043122A (ko) | 2001-05-25 |
| EP1076648B1 (de) | 2006-07-12 |
| DE59913665D1 (de) | 2006-08-24 |
| WO1999055675A1 (de) | 1999-11-04 |
| CN1298392A (zh) | 2001-06-06 |
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