NL1005338C2 - Werkwijze voor de bereiding van een optisch actief fenylglycidylzuurderivaat. - Google Patents
Werkwijze voor de bereiding van een optisch actief fenylglycidylzuurderivaat. Download PDFInfo
- Publication number
- NL1005338C2 NL1005338C2 NL1005338A NL1005338A NL1005338C2 NL 1005338 C2 NL1005338 C2 NL 1005338C2 NL 1005338 A NL1005338 A NL 1005338A NL 1005338 A NL1005338 A NL 1005338A NL 1005338 C2 NL1005338 C2 NL 1005338C2
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- compound
- optically active
- derived
- hetero
- Prior art date
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- -1 phenylglycidyl Chemical group 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000002253 acid Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 150000001414 amino alcohols Chemical class 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 6
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 5
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 4
- 229960004166 diltiazem Drugs 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical group CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910004809 Na2 SO4 Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CUHUYVNPCQYRLG-DTWKUNHWSA-N (2r,3s)-3-(4-methoxyphenyl)oxirane-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@H](C(O)=O)O1 CUHUYVNPCQYRLG-DTWKUNHWSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229940089960 chloroacetate Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LIKSMGVMYCWWEV-UHFFFAOYSA-N 1-(propylamino)-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2C(NCCC)C(O)CC2=C1 LIKSMGVMYCWWEV-UHFFFAOYSA-N 0.000 description 2
- HDXFCPZKMFTOLH-UHFFFAOYSA-N 1-amino-2,3-dihydroinden-1-ol Chemical class C1=CC=C2C(N)(O)CCC2=C1 HDXFCPZKMFTOLH-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007836 KH2PO4 Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007657 benzothiazepines Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VDCVDDXMTSCWNX-OLZOCXBDSA-N (1s,2r)-1-(diethylamino)-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2[C@H](N(CC)CC)[C@H](O)CC2=C1 VDCVDDXMTSCWNX-OLZOCXBDSA-N 0.000 description 1
- LIKSMGVMYCWWEV-NEPJUHHUSA-N (1s,2r)-1-(propylamino)-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2[C@H](NCCC)[C@H](O)CC2=C1 LIKSMGVMYCWWEV-NEPJUHHUSA-N 0.000 description 1
- LOPKSXMQWBYUOI-BDAKNGLRSA-N (1s,2r)-1-amino-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2[C@H](N)[C@H](O)CC2=C1 LOPKSXMQWBYUOI-BDAKNGLRSA-N 0.000 description 1
- NRIVMXXOUOBRAG-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetaldehyde Chemical compound COC1=CC=C(CC=O)C=C1 NRIVMXXOUOBRAG-UHFFFAOYSA-N 0.000 description 1
- SVMGPASVSDZYNS-UHFFFAOYSA-N 2-(4-methoxyphenyl)oxirane-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C(O)=O)OC1 SVMGPASVSDZYNS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 102100030960 DNA replication licensing factor MCM2 Human genes 0.000 description 1
- 101000583807 Homo sapiens DNA replication licensing factor MCM2 Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CMUICKPMHXIUJA-CLAROIROSA-N [(1s,2r)-1-(diethylamino)-2,3-dihydro-1h-inden-2-yl] (2r,3s)-3-(4-methoxyphenyl)oxirane-2-carboxylate Chemical compound C1([C@@H]2O[C@H]2C(=O)O[C@H]2[C@H](C3=CC=CC=C3C2)N(CC)CC)=CC=C(OC)C=C1 CMUICKPMHXIUJA-CLAROIROSA-N 0.000 description 1
- RZMKLWUCFJDCGX-HIFRSBDPSA-N [(1s,2r)-1-(diethylamino)-2,3-dihydro-1h-inden-2-yl] 2-chloroacetate Chemical compound C1=CC=C2[C@H](N(CC)CC)[C@H](OC(=O)CCl)CC2=C1 RZMKLWUCFJDCGX-HIFRSBDPSA-N 0.000 description 1
- GYWWQECFQIGECM-UHFFFAOYSA-N [5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-chloroacetate Chemical compound ClCC(=O)OC1CC(C)CCC1C(C)(C)C1=CC=CC=C1 GYWWQECFQIGECM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- CVZUMGUZDAWOGA-VHSXEESVSA-N methyl (2r,3s)-3-(4-methoxyphenyl)oxirane-2-carboxylate Chemical compound COC(=O)[C@@H]1O[C@H]1C1=CC=C(OC)C=C1 CVZUMGUZDAWOGA-VHSXEESVSA-N 0.000 description 1
- YKNYRRVISWJDSR-UHFFFAOYSA-N methyl oxirane-2-carboxylate Chemical compound COC(=O)C1CO1 YKNYRRVISWJDSR-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VOCFEPGTQRHWLS-NWDGAFQWSA-N tert-butyl (2r,3s)-3-(4-methoxyphenyl)oxirane-2-carboxylate Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@H](C(=O)OC(C)(C)C)O1 VOCFEPGTQRHWLS-NWDGAFQWSA-N 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/24—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1005338A NL1005338C2 (nl) | 1997-02-21 | 1997-02-21 | Werkwijze voor de bereiding van een optisch actief fenylglycidylzuurderivaat. |
| CA002228196A CA2228196A1 (en) | 1997-02-21 | 1998-01-29 | Process for preparing an optically active phenylglycidyl acid derivative |
| DE69800900T DE69800900D1 (de) | 1997-02-21 | 1998-02-16 | Verfahren zur Herstellung eines optisch aktiven Phenylglycidylsäurederivates |
| EP98200484A EP0860439B1 (de) | 1997-02-21 | 1998-02-16 | Verfahren zur Herstellung eines optisch aktiven Phenylglycidylsäurederivates |
| AT98200484T ATE202094T1 (de) | 1997-02-21 | 1998-02-16 | Verfahren zur herstellung eines optisch aktiven phenylglycidylsäurederivates |
| JP10076391A JPH10279572A (ja) | 1997-02-21 | 1998-02-19 | 光学活性なフェニルグリシジル酸誘導体の製造法 |
| IL12339198A IL123391A0 (en) | 1997-02-21 | 1998-02-19 | Process for preparing an optically active phenylglycidyl acid derivative |
| CN98107076A CN1197070A (zh) | 1997-02-21 | 1998-02-20 | 旋光苯基缩水甘油酸衍生物的制备方法 |
| HU9800372A HUP9800372A3 (en) | 1997-02-21 | 1998-02-20 | Process for producing trans-phenyl-glycidyl-acid derivatives |
| US09/027,619 US6025506A (en) | 1997-02-21 | 1998-02-23 | Process for preparing an optically active phenylglycidyl acid derivative |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1005338 | 1997-02-21 | ||
| NL1005338A NL1005338C2 (nl) | 1997-02-21 | 1997-02-21 | Werkwijze voor de bereiding van een optisch actief fenylglycidylzuurderivaat. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL1005338C2 true NL1005338C2 (nl) | 1998-08-24 |
Family
ID=19764467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1005338A NL1005338C2 (nl) | 1997-02-21 | 1997-02-21 | Werkwijze voor de bereiding van een optisch actief fenylglycidylzuurderivaat. |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0860439B1 (de) |
| JP (1) | JPH10279572A (de) |
| CN (1) | CN1197070A (de) |
| AT (1) | ATE202094T1 (de) |
| CA (1) | CA2228196A1 (de) |
| DE (1) | DE69800900D1 (de) |
| HU (1) | HUP9800372A3 (de) |
| IL (1) | IL123391A0 (de) |
| NL (1) | NL1005338C2 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1302261B1 (it) | 1998-09-24 | 2000-09-05 | Zambon Spa | Processo per la risoluzione cinetica enzimatica di 3-fenilglicidatiper transesterificazione con amminoalcoli |
| WO2004081219A1 (en) * | 2003-03-12 | 2004-09-23 | Council Of Scientific And Industrial Research | Stereoselective chemoenzymatic process for preparing optically enriched phenylglycidates |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0342904A2 (de) * | 1988-05-18 | 1989-11-23 | MARION LABORATORIES, INC. (a Delaware corporation) | 2-Hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionsäure-8'-phenylmenthylester, insbesondere für Diltiazem |
-
1997
- 1997-02-21 NL NL1005338A patent/NL1005338C2/nl not_active IP Right Cessation
-
1998
- 1998-01-29 CA CA002228196A patent/CA2228196A1/en not_active Abandoned
- 1998-02-16 DE DE69800900T patent/DE69800900D1/de not_active Expired - Lifetime
- 1998-02-16 AT AT98200484T patent/ATE202094T1/de active
- 1998-02-16 EP EP98200484A patent/EP0860439B1/de not_active Expired - Lifetime
- 1998-02-19 JP JP10076391A patent/JPH10279572A/ja active Pending
- 1998-02-19 IL IL12339198A patent/IL123391A0/xx unknown
- 1998-02-20 HU HU9800372A patent/HUP9800372A3/hu unknown
- 1998-02-20 CN CN98107076A patent/CN1197070A/zh active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0342904A2 (de) * | 1988-05-18 | 1989-11-23 | MARION LABORATORIES, INC. (a Delaware corporation) | 2-Hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionsäure-8'-phenylmenthylester, insbesondere für Diltiazem |
Non-Patent Citations (1)
| Title |
|---|
| A. SCHWARTZ ET AL.: "Enantioselective synthesis of calcium channel blockers of the diltiazem group", JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 3, 1992, WASHINGTON DC, US, pages 851 - 6, XP002042991 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10279572A (ja) | 1998-10-20 |
| HUP9800372A3 (en) | 2001-02-28 |
| ATE202094T1 (de) | 2001-06-15 |
| HUP9800372A2 (hu) | 1999-09-28 |
| CN1197070A (zh) | 1998-10-28 |
| HU9800372D0 (en) | 1998-04-28 |
| CA2228196A1 (en) | 1998-08-21 |
| EP0860439B1 (de) | 2001-06-13 |
| EP0860439A1 (de) | 1998-08-26 |
| IL123391A0 (en) | 1998-09-24 |
| DE69800900D1 (de) | 2001-07-19 |
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| Date | Code | Title | Description |
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| PD2B | A search report has been drawn up | ||
| VD1 | Lapsed due to non-payment of the annual fee |
Effective date: 20010901 |