DK166876B1 - Alkylarylketaler og fremgangsmaade til fremstilling heraf - Google Patents

Alkylarylketaler og fremgangsmaade til fremstilling heraf Download PDF

Info

Publication number: DK166876B1
Authority: DK; Denmark
Prior art keywords: formula; ketals; group; alkyl; naphthyl
Prior art date: 1984-04-06

Application number

DK149785A

Other languages

Danish (da)

English (en)

Other versions

DK149785A (da

DK149785D0 (da

Inventor

Claudio Giordano

Graziano Castaldi

Fulvio Uggeri

Silvia Cavicchioli

Original Assignee

Zambon Spa

Priority date (The priority date 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 date listed.)

1984-04-06

Filing date

1985-04-02

Publication date

1993-07-26

1984-04-06 Priority claimed from IT8407204A external-priority patent/IT1214809B/it

1984-08-06 Priority claimed from IT07206/84A external-priority patent/IT1199447B/it

1984-08-06 Priority claimed from IT8407207A external-priority patent/IT1207420B/it

1985-04-02 Application filed by Zambon Spa filed Critical Zambon Spa

1985-04-02 Publication of DK149785D0 publication Critical patent/DK149785D0/da

1985-10-07 Publication of DK149785A publication Critical patent/DK149785A/da

1993-07-26 Application granted granted Critical

1993-07-26 Publication of DK166876B1 publication Critical patent/DK166876B1/da

Links

238000000034 method Methods 0.000 title claims description 23
229910052751 metal Inorganic materials 0.000 title abstract description 4
239000002184 metal Substances 0.000 title abstract description 4
150000002739 metals Chemical class 0.000 title 1
238000002360 preparation method Methods 0.000 claims abstract description 24
150000001875 compounds Chemical class 0.000 claims abstract description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
239000000460 chlorine Substances 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
229910052740 iodine Chemical group 0.000 claims abstract description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
150000001768 cations Chemical class 0.000 claims abstract 2
125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
-1 C ^-C ^ -haloalkoxy Chemical group 0.000 claims description 57
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 8
150000002576 ketones Chemical class 0.000 claims description 8
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims description 3
230000020477 pH reduction Effects 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 22
150000007513 acids Chemical class 0.000 abstract description 20
230000008707 rearrangement Effects 0.000 abstract description 10
238000005907 ketalization reaction Methods 0.000 abstract description 6
125000004423 acyloxy group Chemical group 0.000 abstract description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract description 3
125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract description 3
125000006686 (C1-C24) alkyl group Chemical group 0.000 abstract 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
125000004430 oxygen atom Chemical group O* 0.000 abstract 1
125000003107 substituted aryl group Chemical group 0.000 abstract 1
150000003892 tartrate salts Chemical class 0.000 abstract 1
239000000203 mixture Substances 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
125000003118 aryl group Chemical group 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000005160 1H NMR spectroscopy Methods 0.000 description 15
239000000243 solution Substances 0.000 description 15
238000004128 high performance liquid chromatography Methods 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
238000000746 purification Methods 0.000 description 6
125000006083 1-bromoethyl group Chemical group 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000284 extract Substances 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
PVRATXCXJDHJJN-SYPWQXSBSA-N dimethyl (3r)-2,3-dihydroxybutanedioate Chemical compound COC(=O)C(O)[C@@H](O)C(=O)OC PVRATXCXJDHJJN-SYPWQXSBSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229960002009 naproxen Drugs 0.000 description 4
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 3
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 3
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 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
XCOAABZEUNQHQG-UHFFFAOYSA-N 2-bromo-1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(C(=O)C(C)Br)C=CC2=CC(OC)=CC=C21 XCOAABZEUNQHQG-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
239000001358 L(+)-tartaric acid Substances 0.000 description 2
235000011002 L(+)-tartaric acid Nutrition 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
PVRATXCXJDHJJN-UHFFFAOYSA-N dimethyl 2,3-dihydroxybutanedioate Chemical compound COC(=O)C(O)C(O)C(=O)OC PVRATXCXJDHJJN-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003899 tartaric acid esters Chemical class 0.000 description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 description 1
OWBTYPJTUOEWEK-SYPWQXSBSA-N (3r)-butane-2,3-diol Chemical compound CC(O)[C@@H](C)O OWBTYPJTUOEWEK-SYPWQXSBSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 description 1
ZRYXMBWYACLLRH-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(OC(F)F)C=C1 ZRYXMBWYACLLRH-UHFFFAOYSA-N 0.000 description 1
DYXXFHYETWSMRP-UHFFFAOYSA-N C(C)(=O)OC(C)C1(OCCO1)C1=CC2=CC=C(C=C2C=C1)OC Chemical compound C(C)(=O)OC(C)C1(OCCO1)C1=CC2=CC=C(C=C2C=C1)OC DYXXFHYETWSMRP-UHFFFAOYSA-N 0.000 description 1
241000282461 Canis lupus Species 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
JHCIAVKSBSYOLH-UHFFFAOYSA-N [1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(OC)(OC)C(C)OS(=O)(=O)C1=CC=C(C)C=C1 JHCIAVKSBSYOLH-UHFFFAOYSA-N 0.000 description 1
AVHMSLZDCWAGMK-UHFFFAOYSA-N [1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-yl] acetate Chemical compound C1=C(C(OC)(OC)C(C)OC(C)=O)C=CC2=CC(OC)=CC=C21 AVHMSLZDCWAGMK-UHFFFAOYSA-N 0.000 description 1
XFSFCYMBIFIDHI-UHFFFAOYSA-N [1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-yl] methanesulfonate Chemical compound C1=C(C(OC)(OC)C(C)OS(C)(=O)=O)C=CC2=CC(OC)=CC=C21 XFSFCYMBIFIDHI-UHFFFAOYSA-N 0.000 description 1
DZHDTWQZHCFJIC-UHFFFAOYSA-N [1-(5-bromo-6-methoxynaphthalen-2-yl)-1,1-dimethoxypropan-2-yl] acetate Chemical compound C1=C(C(OC)(OC)C(C)OC(C)=O)C=CC2=C(Br)C(OC)=CC=C21 DZHDTWQZHCFJIC-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
WXDCPMZAHPHZPC-RFZPGFLSSA-N dimethyl (4r,5r)-1,3-dioxolane-4,5-dicarboxylate Chemical compound COC(=O)[C@@H]1OCO[C@H]1C(=O)OC WXDCPMZAHPHZPC-RFZPGFLSSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
RDJGLLICXDHJDY-UHFFFAOYSA-N fenoprofen Chemical compound OC(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-UHFFFAOYSA-N 0.000 description 1
229960001419 fenoprofen Drugs 0.000 description 1
239000012467 final product Substances 0.000 description 1
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
229960002390 flurbiprofen Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002634 lipophilic molecules Chemical class 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
MDKGKXOCJGEUJW-UHFFFAOYSA-N suprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-UHFFFAOYSA-N 0.000 description 1
229960004492 suprofen Drugs 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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
- A—HUMAN NECESSITIES
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Oil, Petroleum & Natural Gas (AREA)
Pain & Pain Management (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

DK149785A 1984-04-06 1985-04-02 Alkylarylketaler og fremgangsmaade til fremstilling heraf DK166876B1 (da)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
IT8407204A IT1214809B (it)	1984-04-06	1984-04-06	Intermedi utili per la sintesi di acidi carbossilici.
IT720484		1984-04-06
IT07206/84A IT1199447B (it)	1984-08-06	1984-08-06	Intermedi utili per la sintesi di acidi carbossilici
IT8407207A IT1207420B (it)	1984-08-06	1984-08-06	Acidi carbossilici. procedimento per la preparazione di
IT720784		1984-08-06
IT720684		1984-08-06

Publications (3)

Publication Number	Publication Date
DK149785D0 DK149785D0 (da)	1985-04-02
DK149785A DK149785A (da)	1985-10-07
DK166876B1 true DK166876B1 (da)	1993-07-26

Family

ID=27272674

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DK149785A DK166876B1 (da)	1984-04-06	1985-04-02	Alkylarylketaler og fremgangsmaade til fremstilling heraf
DK149885A DK166272C (da)	1984-04-06	1985-04-02	Fremgangsmaade til fremstilling af optisk aktive alfa-arylalkansyrer

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DK149885A DK166272C (da)	1984-04-06	1985-04-02	Fremgangsmaade til fremstilling af optisk aktive alfa-arylalkansyrer

Country Status (18)

Country	Link
US (4)	US4734507A (it)
EP (2)	EP0158913B1 (it)
JP (7)	JPH0784457B2 (it)
KR (2)	KR920010927B1 (it)
AT (2)	ATE35810T1 (it)
AU (2)	AU577362B2 (it)
CA (3)	CA1282410C (it)
DE (2)	DE3567209D1 (it)
DK (2)	DK166876B1 (it)
ES (5)	ES8802295A1 (it)
FI (2)	FI91528C (it)
GR (2)	GR850847B (it)
HU (2)	HU198439B (it)
IE (2)	IE58258B1 (it)
MX (1)	MX169453B (it)
NO (2)	NO169385C (it)
PT (2)	PT80243B (it)
YU (2)	YU43942B (it)

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EP0158913B1 (en) *	1984-04-06	1988-07-20	ZAMBON S.p.A.	Process for the preparation of optically active alpha-arylalkanoic acids and intermediates thereof
IT1201443B (it) *	1985-07-31	1989-02-02	Zambon Spa	Intermedi per la sintesi di acidi carbossilici
IT1190398B (it) *	1985-10-04	1988-02-16	Zambon Spa	Processo per la preparazione di alfa aloalchil-aril-chetoni otticamente attivi
IT1190399B (it) *	1985-10-04	1988-02-16	Zambon Spa	Processo per la preparazione di composti carbonilici otticamente attivi
IT1190436B (it) *	1985-12-13	1988-02-16	Zambon Spa	Processo stereoselettivo per la preparazione di composti carbonilici alfa,beta-disostituiti otticamente attivi
IT1197800B (it) *	1986-08-01	1988-12-06	Zambon Spa	Processo per la sintesi di acidi carbossilici
IT1198234B (it) *	1986-12-23	1988-12-21	Zambon Spa	Processo stereoconvergente per la preparazione di acidi carbossilici otticamente attivi
US4912248A (en) *	1987-05-18	1990-03-27	The Procter & Gamble Company	Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation
IT1227537B (it) *	1987-07-28	1991-04-12	Zambon Spa	Processo per la preparazione dell'acido s(+)-2-(6-metossi-2-naftil)- propionico
AU643210B2 (en) *	1989-05-16	1993-11-11	Medice Chem.-Pharm. Fabrik Putter Gmbh & Co. Kg	Process for preparing optically active 2-aryl-alkanoic acids, in particular 2-ayrl-propionic acids
US5266723A (en) *	1989-05-16	1993-11-30	Medice, Ltd., Chem.-Pharm. Fabrik Putter Gmbh & Co. Kg	Process for the preparation of optically active 2-aryl-alkanoic acids, especially 2-aryl-propionic acids
FI94339C (fi)	1989-07-21	1995-08-25	Warner Lambert Co	Menetelmä farmaseuttisesti käyttökelpoisen /R-(R,R)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi
US6194140B1 (en)	1990-04-04	2001-02-27	Chiron Corporation	HCV NS3 protein fragments having helicase activity and improved solubility
IT1251958B (it) *	1991-10-18	1995-05-27	Zambon Spa	Processo per la dealogenazione di derivati del naftalene
US5434302A (en) *	1994-02-18	1995-07-18	Paradies; H. Henrich	Method for the preparation of optically active 2-aryl alkyl aldehydes and formation of 2-aryl-alkanoic acids therefrom
US5756851A (en) *	1996-10-21	1998-05-26	Albemarle Corporation	Production of nabumetone or precursors thereof
US5792886A (en) *	1997-01-08	1998-08-11	Albemarle Corporation	Production of racemic 2-(6-methoxy-2-naphthyl) propionic acid of precursors thereof
US6096920A (en) *	1997-01-08	2000-08-01	Albemarle Corporation	Preparation of carboxylic compounds and their derivatives
US6080888A (en) *	1997-01-08	2000-06-27	Albemarle Corporation	Preparation of olefinic compounds and carboxylic derivatives thereof
US5942527A (en) *	1997-08-27	1999-08-24	K & K Biosciences, Inc.	Hydrazones, hydrazines, semicarbazones and thiosemicarbazones derived from pyridyl ketones as anticonvulsant drugs and excitatory amino acid antagonists
JP4969002B2 (ja)	1999-06-08	2012-07-04	ユニバーシテイ・オブ・アイオワ・リサーチ・フアウンデーシヨン	ｒＡＡＶ形質導入を増加するための化合物および方法
IT1315212B1 (it) *	1999-07-26	2003-02-03	Consiglio Nazionale Ricerche	Impiego di ortoesteri per la sintesi di acidi chirali in processi diesterificazione irreversibili biocatalizzati.
JP2006521825A (ja)	2003-03-31	2006-09-28	ユニバーシテイ・オブ・アイオワ・リサーチ・フアウンデーシヨン	ｒＡＡＶ導入を高めるための化合物および方法
JP4511809B2 (ja) *	2003-06-19	2010-07-28	川口薬品株式会社	ムスコンのアセタール付加体、その調製方法、並びに（±）−ムスコンの光学分割方法
GB0501237D0 (en) *	2005-01-21	2005-03-02	Givaudan Sa	Organic compounds
DE102010063609A1 (de)	2010-12-20	2012-06-21	Awd.Pharma Gmbh & Co. Kg	Neue Multikomponentenkristalle aus ([2-Amino-6-(4-fluoro-benzylamino)-pyridin-3yl)-carbamidsäureethylester und einer Arylpropionsäure
WO2017139381A1 (en)	2016-02-08	2017-08-17	University Of Iowa Research Foundation	Methods to produce chimeric adeno-associated virus/bocavirus parvovirus
US11684679B2 (en)	2016-03-07	2023-06-27	University Of Iowa Research Foundation	AAV-mediated expression using a synthetic promoter and enhancer
WO2017205739A1 (en)	2016-05-26	2017-11-30	University Of Iowa Research Foundation	cis AND trans REQUIREMENTS FOR TERMINAL RESOLUTION OF HUMAN BOCAVIRUS 1
WO2018132747A1 (en)	2017-01-13	2018-07-19	University Of Iowa Research Foundation	Bocaparvovirus small noncoding rna and uses thereof
CN110229069A (zh) *	2019-07-16	2019-09-13	重庆医药高等专科学校	三甲基苯基三溴化铵的制备方法及萘普生生产中三甲基苯基三溴化铵的回收利用方法
CN114644554A (zh) *	2020-12-21	2022-06-21	上海医药工业研究院	(s)-氟比洛芬的制备方法及其中间体

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US3247240A (en) *	1962-01-05	1966-04-19	Geigy Ag J R	Process for the preparation of carbonyl compounds containing a hindered phenol group
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US4107439A (en) *	1976-06-16	1978-08-15	The Upjohn Company	Process for preparing arylalkanoic acid derivatives
EP0034781B1 (de) *	1980-02-21	1984-02-01	BASF Aktiengesellschaft	Verfahren zur Herstellung von duktilen Verbundwerkstoffen
IE50898B1 (en) *	1980-02-26	1986-08-06	Blaschim Spa	Process for preparing esters of 2-(6'-methoxy-2'-naphthyl)-propionic acid via rearrangement of new ketals of 2-halo-1-(6'-methoxy-2'-naphthyl)-propan-1-one
JPS5810525A (ja) *	1981-06-15	1983-01-21	Sagami Chem Res Center	光学活性な１−芳香族基置換−１−アルカノン類の製造方法
IT1190741B (it) *	1982-03-22	1988-02-24	Blaschim Spa	Procedimento per preparare esteri dell'acido 2-(6'-metossi-2'-naftil)-propionico
US4623736A (en) *	1982-07-09	1986-11-18	The Upjohn Company	Arylalkanoic acid process improvement
EP0101124B1 (en) *	1982-08-06	1986-01-29	ZAMBON S.p.A.	Process for preparing alpha arylalkanoic acids
JPS6071271A (ja) *	1983-09-29	1985-04-23	Fuji Xerox Co Ltd	感熱記録装置
EP0158913B1 (en) *	1984-04-06	1988-07-20	ZAMBON S.p.A.	Process for the preparation of optically active alpha-arylalkanoic acids and intermediates thereof
JPH0585102A (ja) *	1991-09-24	1993-04-06	Nissan Motor Co Ltd	トルクチユーブ装置

1985
- 1985-04-01 EP EP85103906A patent/EP0158913B1/en not_active Expired
- 1985-04-01 DE DE8585103907T patent/DE3567209D1/de not_active Expired
- 1985-04-01 DE DE8585103906T patent/DE3563848D1/de not_active Expired
- 1985-04-01 EP EP85103907A patent/EP0158255B1/en not_active Expired
- 1985-04-01 AT AT85103906T patent/ATE35810T1/de not_active IP Right Cessation
- 1985-04-01 AT AT85103907T patent/ATE39691T1/de active
- 1985-04-02 DK DK149785A patent/DK166876B1/da not_active IP Right Cessation
- 1985-04-02 FI FI851318A patent/FI91528C/fi not_active IP Right Cessation
- 1985-04-02 NO NO851349A patent/NO169385C/no not_active IP Right Cessation
- 1985-04-02 FI FI851317A patent/FI91393C/fi not_active IP Right Cessation
- 1985-04-02 NO NO851350A patent/NO170685C/no unknown
- 1985-04-02 DK DK149885A patent/DK166272C/da not_active Application Discontinuation
- 1985-04-03 ES ES542640A patent/ES8802295A1/es not_active Expired
- 1985-04-03 HU HU851281A patent/HU198439B/hu not_active IP Right Cessation
- 1985-04-03 HU HU851282A patent/HU197711B/hu unknown
- 1985-04-03 ES ES542641A patent/ES8701748A1/es not_active Expired
- 1985-04-04 AU AU40840/85A patent/AU577362B2/en not_active Ceased
- 1985-04-04 IE IE88085A patent/IE58258B1/en not_active IP Right Cessation
- 1985-04-04 CA CA000478585A patent/CA1282410C/en not_active Expired - Fee Related
- 1985-04-04 PT PT80243A patent/PT80243B/pt not_active IP Right Cessation
- 1985-04-04 IE IE87985A patent/IE58032B1/en not_active IP Right Cessation
- 1985-04-04 GR GR850847A patent/GR850847B/el unknown
- 1985-04-04 GR GR850846A patent/GR850846B/el unknown
- 1985-04-04 PT PT80244A patent/PT80244B/pt not_active IP Right Cessation
- 1985-04-04 AU AU40842/85A patent/AU575927B2/en not_active Ceased
- 1985-04-04 CA CA000478586A patent/CA1281029C/en not_active Expired - Fee Related
- 1985-04-05 US US06/720,379 patent/US4734507A/en not_active Expired - Lifetime
- 1985-04-05 JP JP60071271A patent/JPH0784457B2/ja not_active Expired - Lifetime
- 1985-04-05 US US06/720,380 patent/US4697036A/en not_active Expired - Lifetime
- 1985-04-05 YU YU570/85A patent/YU43942B/xx unknown
- 1985-04-06 KR KR1019850002312A patent/KR920010927B1/ko not_active Expired
- 1985-04-06 KR KR1019850002311A patent/KR920007223B1/ko not_active Expired
- 1985-04-06 JP JP60073388A patent/JPH0791214B2/ja not_active Expired - Lifetime
- 1985-04-08 MX MX005727A patent/MX169453B/es unknown
- 1985-04-08 YU YU579/85A patent/YU43686B/xx unknown
1986
- 1986-01-31 ES ES551476A patent/ES8705415A1/es not_active Expired
- 1986-05-14 ES ES554936A patent/ES8706661A1/es not_active Expired
- 1986-08-01 ES ES557037A patent/ES8707490A1/es not_active Expired
1987
- 1987-08-05 US US07/082,196 patent/US4888433A/en not_active Expired - Lifetime
- 1987-12-17 US US07/134,197 patent/US4855464A/en not_active Expired - Lifetime
1989
- 1989-05-02 CA CA000598530A patent/CA1320495C/en not_active Expired - Fee Related
1993
- 1993-03-22 JP JP5085102A patent/JPH0776193B2/ja not_active Expired - Lifetime
- 1993-03-22 JP JP5085103A patent/JPH06100498A/ja active Pending
- 1993-03-22 JP JP5085104A patent/JPH07107018B2/ja not_active Expired - Fee Related
1995
- 1995-03-06 JP JP7045380A patent/JP2700023B2/ja not_active Expired - Fee Related
- 1995-03-06 JP JP7045381A patent/JP2700024B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
HU197711B (en)	1989-05-29
HUT40598A (en)	1987-01-28
KR920007223B1 (ko)	1992-08-28
JPH06100491A (ja)	1994-04-12
IE58258B1 (en)	1993-08-25
AU4084285A (en)	1985-10-10
YU57085A (en)	1987-12-31
KR850008484A (ko)	1985-12-18
NO851350L (no)	1985-10-07
ES554936A0 (es)	1987-07-01
FI91528B (fi)	1994-03-31
US4888433A (en)	1989-12-19
ES557037A0 (es)	1987-08-01
ES551476A0 (es)	1987-05-01
FI851317L (fi)	1985-10-07
YU43942B (en)	1989-12-31
NO169385C (no)	1992-06-17
EP0158255A2 (en)	1985-10-16
US4697036A (en)	1987-09-29
JPS60228441A (ja)	1985-11-13
ATE39691T1 (de)	1989-01-15
ES8705415A1 (es)	1987-05-01
DE3567209D1 (en)	1989-02-09
HUT37931A (en)	1986-03-28
ES542641A0 (es)	1986-12-16
CA1320495C (en)	1993-07-20
JP2700024B2 (ja)	1998-01-19
CA1282410C (en)	1991-04-02
PT80243B (en)	1987-04-28
ES8802295A1 (es)	1988-05-01
JPS60228440A (ja)	1985-11-13
IE58032B1 (en)	1993-06-16
HU198439B (en)	1989-10-30
ES8707490A1 (es)	1987-08-01
NO851349L (no)	1985-10-07
JPH06116201A (ja)	1994-04-26
IE850879L (en)	1985-10-06
DK149785A (da)	1985-10-07
FI91528C (fi)	1994-07-11
EP0158255B1 (en)	1989-01-04
AU575927B2 (en)	1988-08-11
EP0158913B1 (en)	1988-07-20
GR850847B (it)	1985-11-25
JPH0867652A (ja)	1996-03-12
FI851318A0 (fi)	1985-04-02
AU4084085A (en)	1985-10-10
KR920010927B1 (ko)	1992-12-24
JPH0859552A (ja)	1996-03-05
EP0158255A3 (en)	1986-09-03
AU577362B2 (en)	1988-09-22
DK149785D0 (da)	1985-04-02
YU43686B (en)	1989-10-31
FI91393B (fi)	1994-03-15
FI851318L (fi)	1985-10-07
PT80243A (en)	1985-05-01
JPH0776193B2 (ja)	1995-08-16
NO170685B (no)	1992-08-10
ES542640A0 (es)	1988-05-01
ES8701748A1 (es)	1986-12-16
JPH0791214B2 (ja)	1995-10-04
DK149885D0 (da)	1985-04-02
NO170685C (no)	1992-11-18
ES8706661A1 (es)	1987-07-01
US4855464A (en)	1989-08-08
MX169453B (es)	1993-07-06
YU57985A (en)	1987-12-31
DK149885A (da)	1985-10-07
US4734507A (en)	1988-03-29
EP0158913A2 (en)	1985-10-23
DK166272B (da)	1993-03-29
FI91393C (fi)	1994-06-27
ATE35810T1 (de)	1988-08-15
JPH0784457B2 (ja)	1995-09-13
PT80244A (en)	1985-05-01
FI851317A0 (fi)	1985-04-02
JPH06100498A (ja)	1994-04-12
JPH07107018B2 (ja)	1995-11-15
DK166272C (da)	1993-10-25
IE850880L (en)	1985-10-06
JP2700023B2 (ja)	1998-01-19
NO169385B (no)	1992-03-09
CA1281029C (en)	1991-03-05
PT80244B (en)	1987-04-23
EP0158913A3 (en)	1985-12-11
KR850007594A (ko)	1985-12-07
GR850846B (it)	1985-11-25
DE3563848D1 (en)	1988-08-25

Legal Events

Date	Code	Title
1993-07-26	B1	Patent granted (law 1993)
1994-05-24	PBP	Patent lapsed
1999-11-29	PBP	Patent lapsed

Publication	Publication Date	Title
EP0158255B1 (en)	1989-01-04	Optically active ketals, processes for their preparation and their use in the synthesis of apha-arylakanoic acids
JP2617960B2 (ja)	1997-06-11	光学活性カルボン酸をつくる立体異性化方法
EP1940387B1 (en)	2012-11-28	Process for the stereoselective preparation of (-)-halofenate and intermediates thereof
FI93642C (fi)	1995-05-10	Menetelmä optisesti aktiivisten -aryylialkaanikarboksyylihappojen valmistamiseksi
FI92688B (fi)	1994-09-15	Menetelmä optisesti aktiivisten -aryylialkaanikarboksyylihappojen valmistamiseksi
FI92823C (fi)	1995-01-10	Optisesti aktiivisia aryylialkyyliketaaleita
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