CA1087631A - Derives de l'acide 2-phenylpropionique et procede de preparation - Google Patents

Derives de l'acide 2-phenylpropionique et procede de preparation

Info

Publication number: CA1087631A
Authority: CA; Canada
Prior art keywords: formula; compound; acid; bromine; iodine
Prior art date: 1978-01-24
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.): Expired

Application number

CA295,499A

Other languages

English (en)

Inventor

Carlos Ferrer

Juan Colome

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ferrer Internacional SA

Original Assignee

Ferrer Internacional SA

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.)

1978-01-24

Filing date

1978-01-24

Publication date

1980-10-14

1978-01-24 Application filed by Ferrer Internacional SA filed Critical Ferrer Internacional SA

1978-01-24 Priority to CA295,499A priority Critical patent/CA1087631A/fr

1980-10-14 Application granted granted Critical

1980-10-14 Publication of CA1087631A publication Critical patent/CA1087631A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 9
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 title abstract description 3
239000002253 acid Substances 0.000 claims abstract description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 9
230000020477 pH reduction Effects 0.000 claims abstract description 7
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 6
239000011707 mineral Substances 0.000 claims abstract description 6
238000007127 saponification reaction Methods 0.000 claims abstract description 4
125000005907 alkyl ester group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 82
239000000460 chlorine Substances 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
229910052794 bromium Inorganic materials 0.000 claims description 20
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Chemical group 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
125000001246 bromo group Chemical group Br* 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
239000001117 sulphuric acid Substances 0.000 claims description 9
235000011149 sulphuric acid Nutrition 0.000 claims description 9
238000005903 acid hydrolysis reaction Methods 0.000 claims description 7
ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 claims description 5
150000004703 alkoxides Chemical class 0.000 claims description 4
238000006114 decarboxylation reaction Methods 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
230000011987 methylation Effects 0.000 claims description 4
238000007069 methylation reaction Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229910006069 SO3H Inorganic materials 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
239000011630 iodine Chemical group 0.000 claims description 2
229910052740 iodine Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
235000013350 formula milk Nutrition 0.000 claims 73
230000001035 methylating effect Effects 0.000 claims 3
239000000543 intermediate Substances 0.000 claims 2
KYHPZLOCYZGUFF-UHFFFAOYSA-N 2-[(3-chloro-4-methoxyphenyl)methyl]propanedioic acid Chemical compound COC1=CC=C(CC(C(O)=O)C(O)=O)C=C1Cl KYHPZLOCYZGUFF-UHFFFAOYSA-N 0.000 claims 1
150000001805 chlorine compounds Chemical group 0.000 claims 1
230000000911 decarboxylating effect Effects 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
239000001294 propane Substances 0.000 claims 1
230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
RGPDEAGGEXEMMM-UHFFFAOYSA-N Nefopam Chemical compound C12=CC=CC=C2CN(C)CCOC1C1=CC=CC=C1 RGPDEAGGEXEMMM-UHFFFAOYSA-N 0.000 abstract 1
230000000202 analgesic effect Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
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 21
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000010992 reflux Methods 0.000 description 11
235000019260 propionic acid Nutrition 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 8
230000000694 effects Effects 0.000 description 8
ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 description 6
229960005142 alclofenac Drugs 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
238000002329 infrared spectrum Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
-1 Aliphatic halogenated hydrocarbons Chemical class 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
102100038916 Caspase-5 Human genes 0.000 description 1
101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000000307 algesic effect Effects 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001047 pyretic effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000004904 shortening Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 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
239000003643 water by type Substances 0.000 description 1

Landscapes

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

CA295,499A 1978-01-24 1978-01-24 Derives de l'acide 2-phenylpropionique et procede de preparation Expired CA1087631A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA295,499A CA1087631A (fr)	1978-01-24	1978-01-24	Derives de l'acide 2-phenylpropionique et procede de preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA295,499A CA1087631A (fr)	1978-01-24	1978-01-24	Derives de l'acide 2-phenylpropionique et procede de preparation

Publications (1)

Publication Number	Publication Date
CA1087631A true CA1087631A (fr)	1980-10-14

Family

ID=4110611

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA295,499A Expired CA1087631A (fr)	1978-01-24	1978-01-24	Derives de l'acide 2-phenylpropionique et procede de preparation

Country Status (1)

Country	Link
CA (1)	CA1087631A (fr)

1978
- 1978-01-24 CA CA295,499A patent/CA1087631A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-10-14	MKEX	Expiry

Publication	Publication Date	Title
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