CA1037964A - Acides 2-((3,5-dl-ter-butyle-4-hydroxyphenyle)(thio) alcanoiques et leuers derives et acides 2-((3,5-bis(1,1dimethyle-ethyle)phenyl)thio)- alcanoieques et leurs esters - Google Patents

Acides 2-((3,5-dl-ter-butyle-4-hydroxyphenyle)(thio) alcanoiques et leuers derives et acides 2-((3,5-bis(1,1dimethyle-ethyle)phenyl)thio)- alcanoieques et leurs esters

Info

Publication number: CA1037964A
Authority: CA; Canada
Prior art keywords: butyl; tert; thio; acid; hydroxyphenyl
Prior art date: 1973-02-14
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

CA191,746A

Other languages

English (en)

Other versions

CA191746S (en

Inventor

Eugene R. Wagner

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.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

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.)

1973-02-14

Filing date

1974-02-05

Publication date

1978-09-05

1974-02-05 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1978-09-05 Application granted granted Critical

1978-09-05 Publication of CA1037964A publication Critical patent/CA1037964A/fr

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 67
239000002253 acid Substances 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 16
238000000034 method Methods 0.000 claims description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
239000002585 base Substances 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
239000011593 sulfur Substances 0.000 claims description 13
NFVMNXZFSKGLDR-UHFFFAOYSA-N 2,6-ditert-butyl-4-sulfanylphenol Chemical compound CC(C)(C)C1=CC(S)=CC(C(C)(C)C)=C1O NFVMNXZFSKGLDR-UHFFFAOYSA-N 0.000 claims description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
CQGSORMFKDTILR-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylhexanoic acid Chemical compound CCCCC(C(O)=O)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 CQGSORMFKDTILR-UHFFFAOYSA-N 0.000 claims description 4
QBATUWSZPKIFEO-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropanoic acid Chemical compound OC(=O)C(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 QBATUWSZPKIFEO-UHFFFAOYSA-N 0.000 claims description 4
IVZUKFYFBUPLRZ-UHFFFAOYSA-N 3,5-ditert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC(S)=CC(C(C)(C)C)=C1 IVZUKFYFBUPLRZ-UHFFFAOYSA-N 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
KOUAQOCYMAENKN-UHFFFAOYSA-N ethyl 2-bromohexanoate Chemical compound CCCCC(Br)C(=O)OCC KOUAQOCYMAENKN-UHFFFAOYSA-N 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
LZLHAKQPGAYWPM-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-2-methylbutanoic acid Chemical compound CCC(C)(C(O)=O)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LZLHAKQPGAYWPM-UHFFFAOYSA-N 0.000 claims description 3
USWXQWODEGJPLW-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylheptanoic acid Chemical compound CCCCCC(C(O)=O)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 USWXQWODEGJPLW-UHFFFAOYSA-N 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
DWEQULNWCCYCET-UHFFFAOYSA-N ethyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylhexanoate Chemical compound CCCCC(C(=O)OCC)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 DWEQULNWCCYCET-UHFFFAOYSA-N 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
239000012429 reaction media Substances 0.000 claims description 3
HZTPKMIMXLTOSK-UHFFFAOYSA-N 2-bromohexanoic acid Chemical compound CCCCC(Br)C(O)=O HZTPKMIMXLTOSK-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
229960000583 acetic acid Drugs 0.000 claims description 2
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
239000012362 glacial acetic acid Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
AYKRAYYKAWNRMG-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-2-methyloctanoic acid Chemical compound CCCCCCC(C)(C(O)=O)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 AYKRAYYKAWNRMG-UHFFFAOYSA-N 0.000 claims 2
OQGQYOUCVSVKMR-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylbutanoic acid Chemical compound CCC(C(O)=O)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 OQGQYOUCVSVKMR-UHFFFAOYSA-N 0.000 claims 2
QNNBTWOPPCYKOP-UHFFFAOYSA-N 2-bromo-2-methylbutanoic acid Chemical compound CCC(C)(Br)C(O)=O QNNBTWOPPCYKOP-UHFFFAOYSA-N 0.000 claims 1
IFONCAQYJGFRIF-UHFFFAOYSA-N 2-bromo-2-methyloctanoic acid Chemical compound CCCCCCC(C)(Br)C(O)=O IFONCAQYJGFRIF-UHFFFAOYSA-N 0.000 claims 1
YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 claims 1
NQRFAUVGDLHPGH-UHFFFAOYSA-N 2-bromoheptanoic acid Chemical compound CCCCCC(Br)C(O)=O NQRFAUVGDLHPGH-UHFFFAOYSA-N 0.000 claims 1
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 41
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 10
150000002632 lipids Chemical class 0.000 abstract description 9
241000124008 Mammalia Species 0.000 abstract description 7
150000007513 acids Chemical class 0.000 abstract description 7
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
125000000446 sulfanediyl group Chemical group *S* 0.000 description 19
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 17
241000700159 Rattus Species 0.000 description 16
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
-1 alkyl radicals Chemical class 0.000 description 14
239000002244 precipitate Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000376 reactant Substances 0.000 description 11
230000009467 reduction Effects 0.000 description 11
238000003756 stirring Methods 0.000 description 11
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 10
210000002966 serum Anatomy 0.000 description 10
229940107161 cholesterol Drugs 0.000 description 9
230000000875 corresponding effect Effects 0.000 description 9
235000005911 diet Nutrition 0.000 description 9
230000037213 diet Effects 0.000 description 9
235000012000 cholesterol Nutrition 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
150000002431 hydrogen Chemical class 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 6
229960002163 hydrogen peroxide Drugs 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000000047 product Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
239000005641 Methyl octanoate Substances 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
229940073584 methylene chloride Drugs 0.000 description 4
230000020477 pH reduction Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000003826 tablet Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
208000031226 Hyperlipidaemia Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000011149 active material Substances 0.000 description 3
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
239000008116 calcium stearate Substances 0.000 description 3
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235000005687 corn oil Nutrition 0.000 description 3
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239000008101 lactose Substances 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
239000000454 talc Substances 0.000 description 3
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230000001225 therapeutic effect Effects 0.000 description 3
238000011282 treatment Methods 0.000 description 3
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000004380 Cholic acid Substances 0.000 description 2
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230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
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150000002500 ions Chemical class 0.000 description 2
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208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
244000020518 Carthamus tinctorius Species 0.000 description 1
235000003255 Carthamus tinctorius Nutrition 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000237858 Gastropoda Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
239000004147 Sorbitan trioleate Substances 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
JGDITNMASUZKPW-UHFFFAOYSA-K aluminium trichloride hexahydrate Chemical compound O.O.O.O.O.O.Cl[Al](Cl)Cl JGDITNMASUZKPW-UHFFFAOYSA-K 0.000 description 1
229940009861 aluminum chloride hexahydrate Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000003098 androgen Substances 0.000 description 1
229940030486 androgens Drugs 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000000923 atherogenic effect Effects 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
KAKDVHJNYLKZBI-UHFFFAOYSA-L calcium;2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylheptanoate Chemical compound [Ca+2].CCCCCC(C([O-])=O)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCCCCC(C([O-])=O)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KAKDVHJNYLKZBI-UHFFFAOYSA-L 0.000 description 1
LVGWCGFIYNBUEB-UHFFFAOYSA-L calcium;2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfonylheptanoate Chemical compound [Ca+2].CCCCCC(C([O-])=O)S(=O)(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCCCCC(C([O-])=O)S(=O)(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LVGWCGFIYNBUEB-UHFFFAOYSA-L 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
239000003026 cod liver oil Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
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230000000295 complement effect Effects 0.000 description 1
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239000012153 distilled water Substances 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
NHZKOVKSBLMABI-UHFFFAOYSA-N ethyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NHZKOVKSBLMABI-UHFFFAOYSA-N 0.000 description 1
PTLDTEKRPFLEPH-UHFFFAOYSA-N ethyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpentanoate Chemical compound CCOC(=O)C(CCC)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PTLDTEKRPFLEPH-UHFFFAOYSA-N 0.000 description 1
GSSXNVQAWLTDEZ-UHFFFAOYSA-N ethyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfonylpentanoate Chemical compound CCOC(=O)C(CCC)S(=O)(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GSSXNVQAWLTDEZ-UHFFFAOYSA-N 0.000 description 1
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000012628 flowing agent Substances 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
230000002641 glycemic effect Effects 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
208000006575 hypertriglyceridemia Diseases 0.000 description 1
230000000871 hypocholesterolemic effect Effects 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000003264 margarine Substances 0.000 description 1
235000013310 margarine Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
QMRMUMPKWGYDDS-UHFFFAOYSA-N methyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-2-methylpropanoate Chemical compound COC(=O)C(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 QMRMUMPKWGYDDS-UHFFFAOYSA-N 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
TUFCVBMECRJIFA-UHFFFAOYSA-M potassium;2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropanoate Chemical compound [K+].[O-]C(=O)C(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 TUFCVBMECRJIFA-UHFFFAOYSA-M 0.000 description 1
JCBGMFOORHPBQZ-UHFFFAOYSA-M potassium;2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfonylpropanoate Chemical compound [K+].[O-]C(=O)C(C)S(=O)(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JCBGMFOORHPBQZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
XGGXJSUCJSOHIF-UHFFFAOYSA-N propyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-2-methyloctanoate Chemical compound CCCCCCC(C)(C(=O)OCCC)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XGGXJSUCJSOHIF-UHFFFAOYSA-N 0.000 description 1
FBYNQSLPSDLMIQ-UHFFFAOYSA-N propyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyloctanoate Chemical compound CCCCCCC(C(=O)OCCC)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FBYNQSLPSDLMIQ-UHFFFAOYSA-N 0.000 description 1
PVRGQHJBXBFUPN-UHFFFAOYSA-N propyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfonyloctanoate Chemical compound CCCCCCC(C(=O)OCCC)S(=O)(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PVRGQHJBXBFUPN-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
PEXRVUIRCKTRQG-UHFFFAOYSA-M sodium;2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylhexanoate Chemical compound [Na+].CCCCC(C([O-])=O)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PEXRVUIRCKTRQG-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011667 zinc carbonate Substances 0.000 description 1
235000004416 zinc carbonate Nutrition 0.000 description 1
229910000010 zinc carbonate Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA191,746A 1973-02-14 1974-02-05 Acides 2-((3,5-dl-ter-butyle-4-hydroxyphenyle)(thio) alcanoiques et leuers derives et acides 2-((3,5-bis(1,1dimethyle-ethyle)phenyl)thio)- alcanoieques et leurs esters Expired CA1037964A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US33232273A	1973-02-14	1973-02-14
US33232373A	1973-02-14	1973-02-14

Publications (1)

Publication Number	Publication Date
CA1037964A true CA1037964A (fr)	1978-09-05

Family

ID=26988168

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA191,746A Expired CA1037964A (fr)	1973-02-14	1974-02-05	Acides 2-((3,5-dl-ter-butyle-4-hydroxyphenyle)(thio) alcanoiques et leuers derives et acides 2-((3,5-bis(1,1dimethyle-ethyle)phenyl)thio)- alcanoieques et leurs esters

Country Status (4)

Country	Link
CA (1)	CA1037964A (fr)
DE (1)	DE2406812A1 (fr)
FR (1)	FR2217018A1 (fr)
HU (1)	HU167915B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4755524A (en) *	1986-01-31	1988-07-05	G. D. Searle & Co.	Novel phenolic thioethers as inhibitors of 5-lipoxygenase
JP2754039B2 (ja) *	1988-06-24	1998-05-20	塩野義製薬株式会社	ジ―ｔｅｒｔ―ブチルヒドロキシフェニルチオ誘導体
JP2627003B2 (ja) *	1989-01-25	1997-07-02	塩野義製薬株式会社	ジーｔｅｒｔ―ブチルヒドロキシフェニルチオ誘導体
JP2834501B2 (ja) *	1989-11-25	1998-12-09	鐘淵化学工業株式会社	３，４―エポキシ酪酸エステルの製法および中間体

1974
- 1974-02-05 CA CA191,746A patent/CA1037964A/fr not_active Expired
- 1974-02-13 DE DE19742406812 patent/DE2406812A1/de active Pending
- 1974-02-13 FR FR7404831A patent/FR2217018A1/fr active Granted
- 1974-02-14 HU HUDO000378 patent/HU167915B/hu unknown

Also Published As

Publication number	Publication date
FR2217018B1 (fr)	1977-01-28
DE2406812A1 (de)	1974-08-22
FR2217018A1 (en)	1974-09-06
HU167915B (fr)	1976-01-28

Publication	Publication Date	Title
US4078084A (en)	1978-03-07	Novel hypolipidemic 2-(3,5-di-tert-butyl-4-hydroxyphenyl)thio carboxamides
US3385886A (en)	1968-05-28	Phenyl propionic acids
US3641127A (en)	1972-02-08	(3-benzoylphenyl) alkanoic acids
US3652646A (en)	1972-03-28	Carboxylic acid derivatives
US3649679A (en)	1972-03-14	Substituted phenylalkanoic acid derivatives ii
US4031243A (en)	1977-06-21	2-(4-Isobutyl phenyl)butyric acid, salts thereof, and pharmaceutical compositions containing the same
US3729508A (en)	1973-04-24	Sulfonylbenzoic acids
JPS6229423B2 (fr)	1987-06-25
US4012523A (en)	1977-03-15	Hypolipidemic 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-(thio or sulfonyl) alkanoic acids and derivatives
CA1037964A (fr)	1978-09-05	Acides 2-((3,5-dl-ter-butyle-4-hydroxyphenyle)(thio) alcanoiques et leuers derives et acides 2-((3,5-bis(1,1dimethyle-ethyle)phenyl)thio)- alcanoieques et leurs esters
AU611480B2 (en)	1991-06-13	Alkadiene derivatives, their preparation, and pharmaceutical compositions containing them
US4067998A (en)	1978-01-10	2-((3,5-Di-tert-butylphenyl)thio) alkanoic acids and derivatives
EP0017578B1 (fr)	1983-03-23	Acides 5-(2-hydroxy-3-thiopropoxy)chromone-2-carboxyliques, leurs sels et esters, procédé de préparation et médicaments
FR2460934A1 (fr)	1981-01-30	Derives d'isoquinoleine contenant du soufre, procedes pour leur preparation et compositions pharmaceutiques les contenant
BE861454A (fr)	1978-06-02	Derives d'acides thiazolidinecarboxyliques, leur preparation et leur utilisation
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BE621255A (fr)
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