CH542806A - Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze - Google Patents

Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze

Info

Publication number: CH542806A
Authority: CH; Switzerland
Prior art keywords: salt; acid; et2o; salts; biphenylyloxy
Prior art date: 1967-10-06

Application number

CH239570A

Other languages

German (de)

English (en)

Inventor

Gerhard Dr Baschang

Charles Dr Morel

Original Assignee

Ciba Geigy Ag

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.)

1967-10-06

Filing date

1967-10-06

Publication date

1973-10-15

1967-10-06 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1967-10-06 Priority to CH239570A priority Critical patent/CH542806A/de

1973-10-15 Publication of CH542806A publication Critical patent/CH542806A/de

Links

239000002253 acid Substances 0.000 title claims description 14
208000031226 Hyperlipidaemia Diseases 0.000 title 1
150000007513 acids Chemical class 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims abstract description 7
150000002148 esters Chemical class 0.000 claims abstract description 7
-1 alkali metal salt Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 9
RGMMREBHCYXQMA-UHFFFAOYSA-N 2-hydroxyheptanoic acid Chemical compound CCCCCC(O)C(O)=O RGMMREBHCYXQMA-UHFFFAOYSA-N 0.000 claims description 8
WEAFBPWCYVGTAB-UHFFFAOYSA-N 2-(4-phenylphenoxy)heptanoic acid Chemical compound C1=CC(OC(CCCCC)C(O)=O)=CC=C1C1=CC=CC=C1 WEAFBPWCYVGTAB-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000007529 inorganic bases Chemical class 0.000 claims description 5
150000007530 organic bases Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
NQRFAUVGDLHPGH-UHFFFAOYSA-N 2-bromoheptanoic acid Chemical compound CCCCCC(Br)C(O)=O NQRFAUVGDLHPGH-UHFFFAOYSA-N 0.000 claims 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 claims description 3
159000000000 sodium salts Chemical class 0.000 claims description 3
159000000007 calcium salts Chemical class 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
231100000053 low toxicity Toxicity 0.000 abstract description 2
239000006188 syrup Substances 0.000 abstract description 2
235000020357 syrup Nutrition 0.000 abstract description 2
239000003513 alkali Substances 0.000 abstract 1
125000005907 alkyl ester group Chemical group 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
150000001408 amides Chemical class 0.000 abstract 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
GNCLPIAYAPQPOU-UHFFFAOYSA-N ethyl 2-bromoheptanoate Chemical compound CCCCCC(Br)C(=O)OCC GNCLPIAYAPQPOU-UHFFFAOYSA-N 0.000 abstract 1
125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
150000002825 nitriles Chemical class 0.000 abstract 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
239000004480 active ingredient Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000454 talc Substances 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000008298 dragée Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
229920001592 potato starch Polymers 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000011575 calcium Substances 0.000 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 2
230000008020 evaporation Effects 0.000 description 2
210000003736 gastrointestinal content Anatomy 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
QKDQHBXHIDQBQR-UHFFFAOYSA-N 2-chloroheptanoic acid Chemical compound CCCCCC(Cl)C(O)=O QKDQHBXHIDQBQR-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
229940013085 2-diethylaminoethanol Drugs 0.000 description 1
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 1
229920000945 Amylopectin Polymers 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000207199 Citrus Species 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
241001466453 Laminaria Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 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
238000010521 absorption reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
229940012017 ethylenediamine Drugs 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
230000003516 hyperlipidaemic effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
- 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
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH239570A 1967-10-06 1967-10-06 Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze CH542806A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH239570A CH542806A (de)	1967-10-06	1967-10-06	Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1402967A CH501575A (de)	1967-10-06	1967-10-06	Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze
CH239570A CH542806A (de)	1967-10-06	1967-10-06	Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze

Publications (1)

Publication Number	Publication Date
CH542806A true CH542806A (de)	1973-10-15

Family

ID=4397336

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH239570A CH542806A (de)	1967-10-06	1967-10-06	Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze
CH1402967A CH501575A (de)	1967-10-06	1967-10-06	Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1402967A CH501575A (de)	1967-10-06	1967-10-06	Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze

Country Status (10)

Country	Link
AT (3)	AT282604B (fr)
BE (1)	BE721973A (fr)
BR (1)	BR6802881D0 (fr)
CH (2)	CH542806A (fr)
DE (1)	DE1801312A1 (fr)
ES (4)	ES358827A1 (fr)
FR (2)	FR1596597A (fr)
GB (1)	GB1249492A (fr)
IL (1)	IL30817A0 (fr)
NL (1)	NL6813908A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5252252A (en) *	1983-09-10	1993-10-12	Merck Patent Gesellschaft Mit Beschraenkter Haftung	Anisotropic compounds and liquid crystal mixtures
DE3332692A1 (de) *	1983-09-10	1985-03-28	Merck Patent Gmbh, 6100 Darmstadt	Anisotrope verbindungen und fluessigkristallmischungen
KR20060006953A (ko) *	2003-04-30	2006-01-20	디 인스티튜트스 포 파마슈티컬 디스커버리, 엘엘씨	치환된 카르복실산
WO2008033931A1 (fr) *	2006-09-13	2008-03-20	The Institutes For Pharmaceutical Discovery, Llc	Acides carboxyliques de para-xylylène et isothiazolones utiles comme protéines tyrosine phosphatases (ptps) en particulier ptp-ib

1967
- 1967-10-06 CH CH239570A patent/CH542806A/de not_active IP Right Cessation
- 1967-10-06 CH CH1402967A patent/CH501575A/de not_active IP Right Cessation
1968
- 1968-09-27 NL NL6813908A patent/NL6813908A/xx unknown
- 1968-10-04 GB GB47167/68A patent/GB1249492A/en not_active Expired
- 1968-10-04 AT AT968268A patent/AT282604B/de not_active IP Right Cessation
- 1968-10-04 ES ES358827A patent/ES358827A1/es not_active Expired
- 1968-10-04 ES ES358828A patent/ES358828A1/es not_active Expired
- 1968-10-04 BR BR202881/68A patent/BR6802881D0/pt unknown
- 1968-10-04 AT AT765069A patent/AT282608B/de not_active IP Right Cessation
- 1968-10-04 IL IL30817A patent/IL30817A0/xx unknown
- 1968-10-04 DE DE19681801312 patent/DE1801312A1/de active Pending
- 1968-10-04 AT AT764869A patent/AT282607B/de not_active IP Right Cessation
- 1968-10-04 ES ES358825A patent/ES358825A1/es not_active Expired
- 1968-10-04 ES ES358826A patent/ES358826A1/es not_active Expired
- 1968-10-07 BE BE721973D patent/BE721973A/xx unknown
- 1968-10-07 FR FR1596597D patent/FR1596597A/fr not_active Expired
1969
- 1969-01-03 FR FR183176A patent/FR8267M/fr not_active Expired

Also Published As

Publication number	Publication date
BE721973A (fr)	1969-04-08
AT282608B (de)	1970-07-10
GB1249492A (en)	1971-10-13
NL6813908A (fr)	1969-04-09
AT282607B (de)	1970-07-10
DE1801312A1 (de)	1969-05-08
IL30817A0 (en)	1968-12-26
FR1596597A (fr)	1970-06-22
ES358827A1 (es)	1970-06-01
ES358826A1 (es)	1970-06-01
BR6802881D0 (pt)	1973-02-22
CH501575A (de)	1971-01-15
FR8267M (fr)	1970-10-26
AT282604B (de)	1970-07-10
ES358825A1 (es)	1970-06-01
ES358828A1 (es)	1970-06-01

Legal Events

Date	Code	Title	Description
1978-05-12	PL	Patent ceased

Publication	Publication Date	Title
DE2711927A1 (de)	1977-10-06	Pharmazeutisch wirksame polyphenole und verfahren zu ihrer herstellung
DE1134086B (de)	1962-08-02	Verfahren zur Herstellung von analeptisch wirksamen alpha-Aminoisobutyrophenonen und deren Säureadditionssalzen
CH542806A (de)	1973-10-15	Verfahren zur Herstellung einer neuen Aryloxyalkansäure und ihrer Salze
CH621780A5 (fr)	1981-02-27
DE3013502C2 (de)	1985-02-07	[2''-(Trifluormethyl)-phenthiazin-10''-yl-(n-prop-3'''ylpiperazin-4''''-yläth-2'''''-yl)]-ester, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel
DE2513136C3 (de)	1981-04-30	N-(1-Benzylpiperid-4-yl)-benzamide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
DE1956844C3 (de)	1979-02-22	ß-(2,4,6-Trijod-3-amidinophenyl)propionsäuren, deren Herstellung und mindestens eine dieser Verbindungen enthaltende Röntgenkontrastmittel
DE69503196T2 (de)	1999-02-18	Verfahren zur Herstellung von Ranitdinbase in pharmazeutischer Reinheit
DE2007700C2 (de)	1983-04-28	Substituierte o-Anilino-phenäthylalkohole, Verfahren zu ihrer Herstellung und therapeutische Präparate
DE1695500A1 (de)	1971-04-15	Verfahren zum Herstellung von Nitroimidazolcarbamaten
DE3586150T2 (de)	1993-01-14	Amidderivate der 2-(p-aminobenzyl)-buttersaeure und ihrer ester mit blutfettgehaltsenkender wirkung.
DE3104785A1 (de)	1982-02-25	Basische ether der 4-hydroxy-benzophenone, die als (beta)-blocker wirksam sind, und verfahren zu ihrer herstellung
CH653334A5 (de)	1985-12-31	Verfahren zur herstellung von vinkaminsaeureestern.
AT277226B (de)	1969-12-10	Verfahren zur herstellung von neuen pyrrolderivaten und ihren salzen
DE1801312C (de)	1972-09-14	2 (4 Biphenylyloxy)-heptansaure, ihre Alkali und Erdalkahsalze und diese Verbin düngen enthaltene Arzneimittel
CH478762A (de)	1969-09-30	Verfahren zur Herstellung von neuen substituierten Zimtsäuren
DE1803385A1 (de)	1969-05-29	Verfahren zur Herstellung einer neuen Aryloxyalkansaeure und ihrer Salze
CH641174A5 (de)	1984-02-15	Verfahren zur herstellung von n-(4'-chlor-3'-sulfamoyl-benzolsulfonyl)-n-methyl-2-aminomethyl-2-methyl-tetrahydrofuran.
AT329021B (de)	1976-04-26	Verfahren zur herstellung von neuen sulfamylbenzoesauren sowie deren pharmazeutisch annehmbaren salzen und estern
DE2236005C3 (de)	1976-07-08	Dibenzo- eckige Klammer auf d,f eckige Klammer zu -dioxepin- eckige Klammer auf 1,3 eckige Klammer zu -derivate und deren pharmakologisch verträgliche Salze, sowie Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
AT276368B (de)	1969-11-25	Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen
DE2244461C3 (de)	1980-02-21	3-Chlor-4,4'-disulfoxydiphenyl-(2-pvridyl)-methansalze, Verfahren zu deren Herstellung sowie diese Salze enthaltende pharmazeutische Zusammensetzungen
DE2016057C3 (de)	1977-08-18	Eckige Klammer auf (Thenyliden (2)- amino)-oxy] -alkylcarbonsäuren, deren Salze und Alkylester, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
CH505045A (de)	1971-03-31	Verfahren zur Herstellung der neuen 2-(4-Biphenylyloxy)-heptansäure und ihrer Salze
DE1136703B (de)	1962-09-20	Verfahren zur Herstellung von choleretisch wirksamen Phenyl-aethylcarbinol-carbonsaeureestern