CH507235A - Verfahren zur Herstellung von neuen, substituierten Phenylalkansäuren - Google Patents

Verfahren zur Herstellung von neuen, substituierten Phenylalkansäuren

Info

Publication number: CH507235A
Authority: CH; Switzerland
Prior art keywords: pyrryl; general formula; phenyl; acid; butyric acid
Prior art date: 1968-11-20

Application number

CH1919970A

Other languages

German (de)

English (en)

Inventor

Rolf Dr Denss

Franz Dr Ostermayer

Clauson-Kaas Niels

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.)

1968-11-20

Filing date

1968-11-20

Publication date

1971-05-15

1968-11-20 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1968-11-20 Priority to CH1919970A priority Critical patent/CH507235A/de

1968-11-20 Priority claimed from CH1732968A external-priority patent/CH507234A/de

1971-05-15 Publication of CH507235A publication Critical patent/CH507235A/de

Links

239000002253 acid Substances 0.000 title claims description 15
150000007513 acids Chemical class 0.000 title claims description 10
230000001754 anti-pyretic effect Effects 0.000 title abstract description 3
239000002221 antipyretic Substances 0.000 title abstract 2
230000000202 analgesic effect Effects 0.000 title description 3
230000003110 anti-inflammatory effect Effects 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
IRJCMFMTKREIQH-UHFFFAOYSA-N 4-(4-pyrrol-1-ylphenyl)butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1N1C=CC=C1 IRJCMFMTKREIQH-UHFFFAOYSA-N 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
150000007529 inorganic bases Chemical class 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
239000000155 melt Substances 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
230000008018 melting Effects 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
238000000859 sublimation Methods 0.000 claims description 2
230000008022 sublimation Effects 0.000 claims description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
239000013078 crystal Substances 0.000 claims 1
239000002244 precipitate Substances 0.000 claims 1
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
-1 antiphlogistics Substances 0.000 abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
PQOBFOICCWHIEM-UHFFFAOYSA-N 4-(4-pyrrol-1-ylphenyl)butanenitrile Chemical compound N1(C=CC=C1)C1=CC=C(C=C1)CCCC#N PQOBFOICCWHIEM-UHFFFAOYSA-N 0.000 abstract 1
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239000000730 antalgic agent Substances 0.000 abstract 1
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239000012043 crude product Substances 0.000 abstract 1
239000005457 ice water Substances 0.000 abstract 1
239000004480 active ingredient Substances 0.000 description 16
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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
108010010803 Gelatin Proteins 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
229940068917 polyethylene glycols Drugs 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000002775 capsule Substances 0.000 description 3
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238000006722 reduction reaction Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
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239000011701 zinc Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
WLVZHIDRKXDCQO-UHFFFAOYSA-N 4-(3-chloro-4-pyrrol-1-ylphenyl)butanoic acid Chemical compound ClC=1C=C(C=CC1N1C=CC=C1)CCCC(=O)O WLVZHIDRKXDCQO-UHFFFAOYSA-N 0.000 description 2
YDUDSQOJLRADBS-UHFFFAOYSA-N 4-oxo-4-(4-pyrrol-1-ylphenyl)butanoic acid Chemical compound N1(C=CC=C1)C1=CC=C(C(=O)CCC(=O)O)C=C1 YDUDSQOJLRADBS-UHFFFAOYSA-N 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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-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
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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-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
235000010489 acacia gum Nutrition 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000003708 ampul Substances 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000008298 dragée Substances 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
229910052749 magnesium Inorganic materials 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000004672 propanoic acids Chemical class 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000002511 suppository base 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
210000002268 wool Anatomy 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-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
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
ZCNISTYPDSSCHP-UHFFFAOYSA-N 4-(3-chloro-4-pyrrol-1-ylphenyl)-4-oxobutanoic acid Chemical compound ClC=1C=C(C(=O)CCC(=O)O)C=CC1N1C=CC=C1 ZCNISTYPDSSCHP-UHFFFAOYSA-N 0.000 description 1
GVHXQQMLYHDQBE-UHFFFAOYSA-N 4-(4-acetamidophenyl)-4-oxobutanoic acid Chemical compound CC(=O)NC1=CC=C(C(=O)CCC(O)=O)C=C1 GVHXQQMLYHDQBE-UHFFFAOYSA-N 0.000 description 1
WRBOAZUDXNNWNI-UHFFFAOYSA-N 4-(4-aminophenyl)-4-oxobutanoic acid Chemical compound NC1=CC=C(C(=O)CCC(O)=O)C=C1 WRBOAZUDXNNWNI-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 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
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-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
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
239000001828 Gelatine Substances 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
241001466453 Laminaria Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical class O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-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
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
239000001785 acacia senegal l. willd gum Substances 0.000 description 1
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150000001298 alcohols 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
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 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
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 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
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
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235000020971 citrus fruits Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
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235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
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229920001249 ethyl cellulose Polymers 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000011777 magnesium Substances 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
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 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
239000002674 ointment Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 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
239000004296 sodium metabisulphite Substances 0.000 description 1
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229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 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
238000003756 stirring Methods 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
208000011580 syndromic disease Diseases 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
231100001274 therapeutic index Toxicity 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

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

CH1919970A 1968-11-20 1968-11-20 Verfahren zur Herstellung von neuen, substituierten Phenylalkansäuren CH507235A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH1919970A CH507235A (de)	1968-11-20	1968-11-20	Verfahren zur Herstellung von neuen, substituierten Phenylalkansäuren

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1732968A CH507234A (de)	1968-04-29	1968-11-20	Verfahren zur Herstellung von neuen, substituierten Alkansäuren
CH1919970A CH507235A (de)	1968-11-20	1968-11-20	Verfahren zur Herstellung von neuen, substituierten Phenylalkansäuren

Publications (1)

Publication Number	Publication Date
CH507235A true CH507235A (de)	1971-05-15

Family

ID=4424559

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1919970A CH507235A (de)	1968-11-20	1968-11-20	Verfahren zur Herstellung von neuen, substituierten Phenylalkansäuren
CH1919870A CH516552A (de)	1968-11-20	1968-11-20	Verfahren zur Herstellung von neuen, substituierten Alkansäuren

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1919870A CH516552A (de)	1968-11-20	1968-11-20	Verfahren zur Herstellung von neuen, substituierten Alkansäuren

Country Status (3)

Country	Link
CH (2)	CH507235A (cs)
CS (1)	CS161855B2 (cs)
ES (1)	ES366548A1 (cs)

1968
- 1968-11-20 CH CH1919970A patent/CH507235A/de not_active IP Right Cessation
- 1968-11-20 CH CH1919870A patent/CH516552A/de not_active IP Right Cessation
1969
- 1969-04-28 ES ES366548A patent/ES366548A1/es not_active Expired
- 1969-04-28 CS CS800069A patent/CS161855B2/cs unknown

Also Published As

Publication number	Publication date
CS161855B2 (cs)	1975-06-10
CH516552A (de)	1971-12-15
ES366548A1 (es)	1971-01-01

Legal Events

Date	Code	Title	Description
1978-07-14	PL	Patent ceased

Publication	Publication Date	Title
DE1443429C3 (de)	1975-07-31	Alpha-Phenylpropionsäure-Derivate und solche Derivate enthaltende Arzneimittel
DE1618465C3 (de)	1979-05-31	Phenylessigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH524612A (de)	1972-06-30	Verfahren zur Herstellung von neuen Imidazolderivaten
DE2007700C2 (de)	1983-04-28	Substituierte o-Anilino-phenäthylalkohole, Verfahren zu ihrer Herstellung und therapeutische Präparate
DE1643394A1 (de)	1971-06-09	Verfahren zur Herstellung von neuen substituierten Phenylacetamiden
DE2944293A1 (de)	1980-05-08	Alpha , alpha , alpha -trifluor- (aminoaryl)-aethanole, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
CH507235A (de)	1971-05-15	Verfahren zur Herstellung von neuen, substituierten Phenylalkansäuren
DE2144641C3 (de)	1980-12-04	Phenylacethydroxamsäuren und Verfahren zu ihrer Herstellung
DE2354931C2 (de)	1983-12-08	trans-2-Phenylbicyclooctan-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
DE1921655A1 (de)	1969-11-13	Verfahren zur Herstellung von neuen 1,2-Oxazinderivaten
AT276368B (de)	1969-11-25	Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen
AT277226B (de)	1969-12-10	Verfahren zur herstellung von neuen pyrrolderivaten und ihren salzen
CH478762A (de)	1969-09-30	Verfahren zur Herstellung von neuen substituierten Zimtsäuren
DE1793828C3 (de)	1979-10-04	2-(6'-Fluor-2'-naphthyl)-propionsäureamid und dessen Herstellung und Verwendung
DE1815804A1 (de)	1969-07-24	Verfahren zur Herstellung einer neuen substituierten Anthranilsaeure
DE2013256C (cs)	1973-05-24
DE1801312A1 (de)	1969-05-08	Verfahren zur Herstellung einer neuen Aryloxyalkansaeure und ihrer Salze
AT276370B (de)	1969-11-25	Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen
DE2157694C3 (de)	1974-12-19	Phenylessigsäurederivate, Verfahren zu ihrer Herstellung und Phenylessigsäurederivate enthaltende pharmazeutische Zubereitungen
CH535232A (de)	1973-03-31	Verfahren zur Herstellung von neuen, substituierten Phenylessigsäuren und deren Estern
DE1543639C3 (de)	1977-10-06	Verfahren zur Herstellung von substituierten Phenylessigsäure!! und deren Salzen sowie genannte Verbindungen enthaltende pharmazeutische Zusammensetzungen
DE1793592C3 (de)	1978-01-26	Substituierte Phenylessigsäuren und deren Salze sowie diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
DE1921651A1 (de)	1969-11-27	Verfahren zur Herstellung von neuen,substituierten Phenylalkansaeuren
CH485711A (de)	1970-02-15	Verfahren zur Herstellung von neuen, substituierten Phenylessigsäuren und deren Estern
CH487841A (de)	1970-03-31	Verfahren zur Herstellung einer neuen, substituierten Phenylessigsäure