DD234422A5 - Verfahren zur herstellung neuer, optischer aktiver ketale - Google Patents

Verfahren zur herstellung neuer, optischer aktiver ketale Download PDF

Info

Publication number: DD234422A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; naphthyl; methoxy; ketals; mixture
Prior art date: 1984-04-06

Application number

DD85274952A

Other languages

German (de)

English (en)

Inventor

Claudio Giordano

Graziano Castaldi

Fulvio Uggeri

Silvia Cavicchioli

Original Assignee

Zambon S. P. A.,It

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

1985-04-08

Publication date

1986-04-02

1985-04-08 Application filed by Zambon S. P. A.,It filed Critical Zambon S. P. A.,It

1986-04-02 Publication of DD234422A5 publication Critical patent/DD234422A5/de

Links

238000004519 manufacturing process Methods 0.000 title abstract description 3
230000003287 optical effect Effects 0.000 title description 13
238000002360 preparation method Methods 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims description 45
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000003107 substituted aryl group Chemical group 0.000 claims description 2
239000002253 acid Substances 0.000 abstract description 41
150000007513 acids Chemical class 0.000 abstract description 32
150000001875 compounds Chemical class 0.000 abstract description 31
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract description 12
150000002576 ketones Chemical class 0.000 abstract description 10
125000004432 carbon atom Chemical group C* 0.000 abstract description 7
FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 abstract 1
-1 alkali metal cation Chemical class 0.000 description 66
239000000203 mixture Substances 0.000 description 61
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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 23
125000003118 aryl group Chemical group 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 21
230000008707 rearrangement Effects 0.000 description 20
238000005160 1H NMR spectroscopy Methods 0.000 description 19
150000002148 esters Chemical class 0.000 description 18
229960002009 naproxen Drugs 0.000 description 17
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 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000004128 high performance liquid chromatography Methods 0.000 description 15
125000006083 1-bromoethyl group Chemical group 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
238000004440 column chromatography Methods 0.000 description 13
239000003480 eluent Substances 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
239000007858 starting material Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
238000000746 purification Methods 0.000 description 9
238000000926 separation method Methods 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 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 description 8
229910052740 iodine Chemical group 0.000 description 8
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 8
239000002243 precursor Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 7
239000002585 base Substances 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
230000007062 hydrolysis Effects 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
238000003756 stirring Methods 0.000 description 7
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 6
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 6
238000005481 NMR spectroscopy Methods 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
125000004423 acyloxy group Chemical group 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
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 6
238000010438 heat treatment Methods 0.000 description 6
238000005907 ketalization reaction Methods 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
239000011975 tartaric acid Substances 0.000 description 6
235000002906 tartaric acid Nutrition 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
HCCFERHCGFJYGK-QMMMGPOBSA-N (2s)-2-(5-bromo-6-methoxynaphthalen-1-yl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC2=C(Br)C(OC)=CC=C21 HCCFERHCGFJYGK-QMMMGPOBSA-N 0.000 description 4
LZAUUWTZEOYENR-UHFFFAOYSA-N 2-iodo-6-methoxybenzaldehyde Chemical compound COC1=CC=CC(I)=C1C=O LZAUUWTZEOYENR-UHFFFAOYSA-N 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
150000002334 glycols Chemical class 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000002609 medium Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 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
239000001358 L(+)-tartaric acid Substances 0.000 description 3
235000011002 L(+)-tartaric acid Nutrition 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
230000001754 anti-pyretic effect Effects 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
239000000470 constituent Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
JZRWXNBIQCMXSU-UHFFFAOYSA-N 2-(5-bromo-6-methoxynaphthalen-2-yl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=C(Br)C(OC)=CC=C21 JZRWXNBIQCMXSU-UHFFFAOYSA-N 0.000 description 2
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
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
241000700159 Rattus Species 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
125000003158 alcohol group Chemical group 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000036760 body temperature Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
HGBYXKNPEKMQOH-ULHBIWDBSA-N dimethyl (2R,3R)-2-hydroxy-3-[2-(6-methoxynaphthalen-2-yl)propanoyl]butanedioate Chemical compound C1=C(OC)C=CC2=CC(C(C)C(=O)[C@H](C(=O)OC)[C@@H](O)C(=O)OC)=CC=C21 HGBYXKNPEKMQOH-ULHBIWDBSA-N 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
150000002009 diols Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000011261 inert gas Substances 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000003367 polycyclic group Chemical group 0.000 description 2
239000000047 product Substances 0.000 description 2
230000006340 racemization Effects 0.000 description 2
238000010992 reflux Methods 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
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
FEWJPZIEWOKRBE-ZILXKATJSA-N (3R)-2,3-dihydroxybutanedioic acid Chemical compound OC([C@@H](O)C(O)=O)C(O)=O FEWJPZIEWOKRBE-ZILXKATJSA-N 0.000 description 1
125000006686 (C1-C24) alkyl group Chemical group 0.000 description 1
125000005913 (C3-C6) cycloalkyl 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
UODROGXCIVAQDJ-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propanoyl chloride Chemical compound C1=C(C(C)C(Cl)=O)C=CC2=CC(OC)=CC=C21 UODROGXCIVAQDJ-UHFFFAOYSA-N 0.000 description 1
SBNAWXAVNWGSHY-UHFFFAOYSA-N 2-chloro-1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(C(=O)C(C)Cl)C=CC2=CC(OC)=CC=C21 SBNAWXAVNWGSHY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
239000007983 Tris buffer Substances 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
125000002252 acyl group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000004983 alkyl aryl ketones Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
230000009876 antimalignant effect Effects 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
URNAYRDBUUZOIU-UHFFFAOYSA-N ethyl 2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound C1=C(OC)C=CC2=CC(C(C)C(=O)OCC)=CC=C21 URNAYRDBUUZOIU-UHFFFAOYSA-N 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
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229960002390 flurbiprofen Drugs 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
238000001640 fractional crystallisation Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
ZFYFBPCRUQZGJE-UHFFFAOYSA-N methyl 2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound C1=C(OC)C=CC2=CC(C(C)C(=O)OC)=CC=C21 ZFYFBPCRUQZGJE-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
125000000168 pyrrolyl group Chemical group 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
230000035484 reaction time Effects 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
239000003579 shift reagent Substances 0.000 description 1
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229960004492 suprofen Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD85274952A 1984-04-06 1985-04-08 Verfahren zur herstellung neuer, optischer aktiver ketale DD234422A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT8407204A IT1214809B (it)	1984-04-06	1984-04-06	Intermedi utili per la sintesi di acidi carbossilici.

Publications (1)

Publication Number	Publication Date
DD234422A5 true DD234422A5 (de)	1986-04-02

Family

ID=11124618

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD85274952A DD234422A5 (de)	1984-04-06	1985-04-08	Verfahren zur herstellung neuer, optischer aktiver ketale
DD27495385A DD234423A5 (de)	1984-04-06	1985-04-08	Enantioselektives verfahren zur herstellung optischer aktiver - arylalkansaeure

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD27495385A DD234423A5 (de)	1984-04-06	1985-04-08	Enantioselektives verfahren zur herstellung optischer aktiver - arylalkansaeure

Country Status (5)

Country	Link
DD (2)	DD234422A5 (it)
IL (2)	IL74821A (it)
IT (1)	IT1214809B (it)
SU (1)	SU1593567A3 (it)
ZA (2)	ZA852533B (it)

1984
- 1984-04-06 IT IT8407204A patent/IT1214809B/it active
1985
- 1985-04-03 ZA ZA852533A patent/ZA852533B/xx unknown
- 1985-04-03 ZA ZA852532A patent/ZA852532B/xx unknown
- 1985-04-04 IL IL7482185A patent/IL74821A/xx not_active IP Right Cessation
- 1985-04-07 IL IL7483185A patent/IL74831A/xx not_active IP Right Cessation
- 1985-04-08 DD DD85274952A patent/DD234422A5/de not_active IP Right Cessation
- 1985-04-08 DD DD27495385A patent/DD234423A5/de not_active IP Right Cessation
1987
- 1987-04-08 SU SU874202319A patent/SU1593567A3/ru active

Also Published As

Publication number	Publication date
IL74831A (en)	1989-05-15
DD234423A5 (de)	1986-04-02
SU1593567A3 (ru)	1990-09-15
IL74821A (en)	1989-05-15
IT8407204A0 (it)	1984-04-06
IT1214809B (it)	1990-01-18
ZA852532B (en)	1985-11-27
ZA852533B (en)	1985-11-27

Legal Events

Date	Code	Title	Description
1999-07-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
US4855464A (en)	1989-08-08	Optically active ketals, processes for their preparation and their use in the synthesis of alpha-arylalkanoic acids
DE3006277C2 (it)	1990-07-12
DE69102893T4 (de)	1995-08-10	Nervenschützende 3-Piperidino-4-Hydroxychromanderivate.
DE69629387T2 (de)	2004-06-24	Dimere indan verbindungen und ihre pharmazeutische verwendung
CH621115A5 (it)	1981-01-15
DE2902466C2 (it)	1988-03-24
DD206372A5 (de)	1984-01-25	Verfahren zur herstellung von alpha-arylalkansaeuren
DD154017A5 (de)	1982-02-17	Verfahren zur herstellung von substituierten oxirancarbonsaeuren
DE19850301A1 (de)	2000-05-04	Verfahren zur Racematspaltung von 2-Hydroxypropionsäuren
DE2059985C3 (de)	1979-10-04	Rechtsdrehende, basisch substituierte Phenylacetonitrile, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
US5004832A (en)	1991-04-02	Preparing alpha-arylalkanoic acids
DE60116796T2 (de)	2006-11-30	Prozess zur herstellung von r(+)alpha-liponsäure
US4304931A (en)	1981-12-08	Biphenylhydroxypropionic acid derivatives
DE68902946T2 (de)	1993-04-29	Heteroarotinoid-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen.
EP0022972B1 (de)	1983-01-26	Neue Menthylester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Enantiomerentrennung chiraler Carbonsäuren
DD234422A5 (de)	1986-04-02	Verfahren zur herstellung neuer, optischer aktiver ketale
DE2748466A1 (de)	1978-05-03	4a-aryloctahydro-1h-2-pyrindine
US4188491A (en)	1980-02-12	Preparation of therapeutic compounds
DE2619617C2 (it)	1987-10-01
DE69812536T2 (de)	2003-09-04	Verfahren zur Herstellung von optisch aktiven Aminen und von optischen aktiven Carbonsäuren und Zwischenprodukte dafür
DE3786770T2 (de)	1993-11-18	Stereokonvergentverfahren zur Herstellung von optisch aktiven Carbonsäuren.
DE3624912A1 (de)	1988-02-04	Optisch reine 1,3-dioxenone, verfahren zu ihrer herstellung und ihre verwendung
US5760073A (en)	1998-06-02	Substituted 4H-pyrans
EP0923534B1 (de)	2000-10-04	Verfahren zur herstellung von racemischen phenethylaminen
DE3785652T2 (de)	1993-08-12	Zwischenprodukte und deren verwendung fuer die synthese von organischen verbindungen.