Uso de (1R,2R)-3-(3-dimetilamino-1-etil-2-metil-propil)-fenol para tratar el dolor inflamatorio

(1R, 2R)-3-(3-Dimetilamino-1-etil-2-metil-propil)-fenol para uso en el tratamiento del dolor inflamatorio. Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII). Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII), where...

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Hauptverfasser: Kögel, Babette-Yvonne, Friderichs, Elmar, Schiene, Klaus, Haase, Günter, Jahnel, Ulrich
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Friderichs, Elmar
Schiene, Klaus
Haase, Günter
Jahnel, Ulrich
description (1R, 2R)-3-(3-Dimetilamino-1-etil-2-metil-propil)-fenol para uso en el tratamiento del dolor inflamatorio. Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII). Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII), where (A) is a phenyl-substituted tertiary amine of formulae (I)-(III), as racemates, pure or mixed stereoisomers (particularly enantiomers or diastereoisomers), optionally in the form of acids, bases, salts or solvates, preferably hydrates. [Image] X : hydroxy, fluoro, chloro, hydrogen or OCOR 7>; R 1>1-4C linear, branched, saturated or unsaturated alkyl, optionally substituted one or more times, in (I), or 1-4C alkyl, benzyl, trifluoromethyl, hydroxy, benzyloxy. 1-3C alkoxy, chloro or fluoro in (II); R 2> and R 3>hydrogen or 1-4C alkyl (as for R 1>) or together form an optionally substituted 4-7C cycloalkyl; R 9>-R 1> 3>hydrogen, fluoro, chloro, bromo, iodo, (di)fluoromethyl, trifluoromethyl, hydroxy, thiol, OR 1> 4>, trifluoromethoxy, SR 1> 4>, NR 1> 7>R 1> 8>, (trifluoro)methyl- sulfinyl or -sulfonyl, cyano, COOR 1> 4>, nitro, CONR 1> 7>R 1> 8>, 1-6C alkyl (as above) or phenyl, optionally substituted one or more times; R 1> 4>1-6C alkyl, pyridyl, thienyl, thiazolyl, phenyl, benzyl, phenethyl (all optionally substituted one or more times), PO(O-1-4C alkyl)-2, COO1-5C alkyl, CONH(1-3C alkylphenyl), CO(1-5C)alkyl, COCHR 1> 7>-NHR 1> 8>, or CO-phenylene-R 1> 5>; R 1> 5>ortho-OCO(1-3C)alkyl, or meta- or para-CH 2N(R 1> 6>) 2; R 1> 6>1-4C alkyl or morpholino, and all alkyl in R 1> 4>-R 1> 6> are optionally substituted one or more times; R 1> 7> and R 1> 8>hydrogen, 1-6C alkyl (as above), phenyl, benzyl or phenethyl, all optionally substituted one or more times; R 1> 0> with either of R 9> or R 1> together : a OCH 2O, OCH 2CH 2O, OCH=CH, CH=CHO, CH=CMeO, OCMe=CH, (CH 2) 4 or OCH=CHO ring; proviso: in (III), when R 9>, R 1> 1> and R 1> 3> are all hydrogen, one of R 1> 0> and R 1> 2> is hydrogen and the other methoxy, then X is nor hydroxy. ACTIVITY : Analgesic. In the mouse writhing test ( J. Pharmacol. Exp. Ther., 228 (1984) 1) animals were treated with (a) (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol (X); (b) rofecoxib (Y) or (c) a mixture of both at ratio 1:2, then after 30 minutes injected with acetic acid. The ED50 for reduction of writhing was 33 mg/kg for (X) alone and 60.1 mg/kg for (Y) alone, but only 23.3 mg/kg (compare 47 mg/kg for an additive effe
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Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII). Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII), where (A) is a phenyl-substituted tertiary amine of formulae (I)-(III), as racemates, pure or mixed stereoisomers (particularly enantiomers or diastereoisomers), optionally in the form of acids, bases, salts or solvates, preferably hydrates. [Image] X : hydroxy, fluoro, chloro, hydrogen or OCOR 7&gt;; R 1&gt;1-4C linear, branched, saturated or unsaturated alkyl, optionally substituted one or more times, in (I), or 1-4C alkyl, benzyl, trifluoromethyl, hydroxy, benzyloxy. 1-3C alkoxy, chloro or fluoro in (II); R 2&gt; and R 3&gt;hydrogen or 1-4C alkyl (as for R 1&gt;) or together form an optionally substituted 4-7C cycloalkyl; R 9&gt;-R 1&gt; 3&gt;hydrogen, fluoro, chloro, bromo, iodo, (di)fluoromethyl, trifluoromethyl, hydroxy, thiol, OR 1&gt; 4&gt;, trifluoromethoxy, SR 1&gt; 4&gt;, NR 1&gt; 7&gt;R 1&gt; 8&gt;, (trifluoro)methyl- sulfinyl or -sulfonyl, cyano, COOR 1&gt; 4&gt;, nitro, CONR 1&gt; 7&gt;R 1&gt; 8&gt;, 1-6C alkyl (as above) or phenyl, optionally substituted one or more times; R 1&gt; 4&gt;1-6C alkyl, pyridyl, thienyl, thiazolyl, phenyl, benzyl, phenethyl (all optionally substituted one or more times), PO(O-1-4C alkyl)-2, COO1-5C alkyl, CONH(1-3C alkylphenyl), CO(1-5C)alkyl, COCHR 1&gt; 7&gt;-NHR 1&gt; 8&gt;, or CO-phenylene-R 1&gt; 5&gt;; R 1&gt; 5&gt;ortho-OCO(1-3C)alkyl, or meta- or para-CH 2N(R 1&gt; 6&gt;) 2; R 1&gt; 6&gt;1-4C alkyl or morpholino, and all alkyl in R 1&gt; 4&gt;-R 1&gt; 6&gt; are optionally substituted one or more times; R 1&gt; 7&gt; and R 1&gt; 8&gt;hydrogen, 1-6C alkyl (as above), phenyl, benzyl or phenethyl, all optionally substituted one or more times; R 1&gt; 0&gt; with either of R 9&gt; or R 1&gt; together : a OCH 2O, OCH 2CH 2O, OCH=CH, CH=CHO, CH=CMeO, OCMe=CH, (CH 2) 4 or OCH=CHO ring; proviso: in (III), when R 9&gt;, R 1&gt; 1&gt; and R 1&gt; 3&gt; are all hydrogen, one of R 1&gt; 0&gt; and R 1&gt; 2&gt; is hydrogen and the other methoxy, then X is nor hydroxy. ACTIVITY : Analgesic. In the mouse writhing test ( J. Pharmacol. Exp. Ther., 228 (1984) 1) animals were treated with (a) (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol (X); (b) rofecoxib (Y) or (c) a mixture of both at ratio 1:2, then after 30 minutes injected with acetic acid. The ED50 for reduction of writhing was 33 mg/kg for (X) alone and 60.1 mg/kg for (Y) alone, but only 23.3 mg/kg (compare 47 mg/kg for an additive effect) for the mixture. 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Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII). Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII), where (A) is a phenyl-substituted tertiary amine of formulae (I)-(III), as racemates, pure or mixed stereoisomers (particularly enantiomers or diastereoisomers), optionally in the form of acids, bases, salts or solvates, preferably hydrates. [Image] X : hydroxy, fluoro, chloro, hydrogen or OCOR 7&gt;; R 1&gt;1-4C linear, branched, saturated or unsaturated alkyl, optionally substituted one or more times, in (I), or 1-4C alkyl, benzyl, trifluoromethyl, hydroxy, benzyloxy. 1-3C alkoxy, chloro or fluoro in (II); R 2&gt; and R 3&gt;hydrogen or 1-4C alkyl (as for R 1&gt;) or together form an optionally substituted 4-7C cycloalkyl; R 9&gt;-R 1&gt; 3&gt;hydrogen, fluoro, chloro, bromo, iodo, (di)fluoromethyl, trifluoromethyl, hydroxy, thiol, OR 1&gt; 4&gt;, trifluoromethoxy, SR 1&gt; 4&gt;, NR 1&gt; 7&gt;R 1&gt; 8&gt;, (trifluoro)methyl- sulfinyl or -sulfonyl, cyano, COOR 1&gt; 4&gt;, nitro, CONR 1&gt; 7&gt;R 1&gt; 8&gt;, 1-6C alkyl (as above) or phenyl, optionally substituted one or more times; R 1&gt; 4&gt;1-6C alkyl, pyridyl, thienyl, thiazolyl, phenyl, benzyl, phenethyl (all optionally substituted one or more times), PO(O-1-4C alkyl)-2, COO1-5C alkyl, CONH(1-3C alkylphenyl), CO(1-5C)alkyl, COCHR 1&gt; 7&gt;-NHR 1&gt; 8&gt;, or CO-phenylene-R 1&gt; 5&gt;; R 1&gt; 5&gt;ortho-OCO(1-3C)alkyl, or meta- or para-CH 2N(R 1&gt; 6&gt;) 2; R 1&gt; 6&gt;1-4C alkyl or morpholino, and all alkyl in R 1&gt; 4&gt;-R 1&gt; 6&gt; are optionally substituted one or more times; R 1&gt; 7&gt; and R 1&gt; 8&gt;hydrogen, 1-6C alkyl (as above), phenyl, benzyl or phenethyl, all optionally substituted one or more times; R 1&gt; 0&gt; with either of R 9&gt; or R 1&gt; together : a OCH 2O, OCH 2CH 2O, OCH=CH, CH=CHO, CH=CMeO, OCMe=CH, (CH 2) 4 or OCH=CHO ring; proviso: in (III), when R 9&gt;, R 1&gt; 1&gt; and R 1&gt; 3&gt; are all hydrogen, one of R 1&gt; 0&gt; and R 1&gt; 2&gt; is hydrogen and the other methoxy, then X is nor hydroxy. ACTIVITY : Analgesic. In the mouse writhing test ( J. Pharmacol. Exp. Ther., 228 (1984) 1) animals were treated with (a) (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol (X); (b) rofecoxib (Y) or (c) a mixture of both at ratio 1:2, then after 30 minutes injected with acetic acid. The ED50 for reduction of writhing was 33 mg/kg for (X) alone and 60.1 mg/kg for (Y) alone, but only 23.3 mg/kg (compare 47 mg/kg for an additive effect) for the mixture. MECHANISM OF ACTION : None given.</description><subject>HUMAN NECESSITIES</subject><subject>HYGIENE</subject><subject>MEDICAL OR VETERINARY SCIENCE</subject><subject>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</subject><subject>SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2021</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNqNi8sKwjAQRbtxIeo_jLsWnEUahbqWiuta12GwEwikmTDN_-MDP8DVPRzOXVfusQhMDLUZDu3QoMXa4hRmLiHSHJKgwQ9ji1-HWSWH2KDnJBEyKUFRKqTAESaJohCSf3-piAbZVitPceHdbzfV_tqPlxtyFsdLpicnLq6_t505d6fjOFr7T_MCkGQ6fA</recordid><startdate>20210419</startdate><enddate>20210419</enddate><creator>Kögel, Babette-Yvonne</creator><creator>Friderichs, Elmar</creator><creator>Schiene, Klaus</creator><creator>Haase, Günter</creator><creator>Jahnel, Ulrich</creator><scope>EVB</scope></search><sort><creationdate>20210419</creationdate><title>Uso de (1R,2R)-3-(3-dimetilamino-1-etil-2-metil-propil)-fenol para tratar el dolor inflamatorio</title><author>Kögel, Babette-Yvonne ; Friderichs, Elmar ; Schiene, Klaus ; Haase, Günter ; Jahnel, Ulrich</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_ES2819854TT33</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>spa</language><creationdate>2021</creationdate><topic>HUMAN NECESSITIES</topic><topic>HYGIENE</topic><topic>MEDICAL OR VETERINARY SCIENCE</topic><topic>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</topic><topic>SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</topic><toplevel>online_resources</toplevel><creatorcontrib>Kögel, Babette-Yvonne</creatorcontrib><creatorcontrib>Friderichs, Elmar</creatorcontrib><creatorcontrib>Schiene, Klaus</creatorcontrib><creatorcontrib>Haase, Günter</creatorcontrib><creatorcontrib>Jahnel, Ulrich</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Kögel, Babette-Yvonne</au><au>Friderichs, Elmar</au><au>Schiene, Klaus</au><au>Haase, Günter</au><au>Jahnel, Ulrich</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Uso de (1R,2R)-3-(3-dimetilamino-1-etil-2-metil-propil)-fenol para tratar el dolor inflamatorio</title><date>2021-04-19</date><risdate>2021</risdate><abstract>(1R, 2R)-3-(3-Dimetilamino-1-etil-2-metil-propil)-fenol para uso en el tratamiento del dolor inflamatorio. Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII). Mixture (X) of at least one analgesic (A) and an inhibitor (B) of cyclo-oxygenase II (COXII), where (A) is a phenyl-substituted tertiary amine of formulae (I)-(III), as racemates, pure or mixed stereoisomers (particularly enantiomers or diastereoisomers), optionally in the form of acids, bases, salts or solvates, preferably hydrates. [Image] X : hydroxy, fluoro, chloro, hydrogen or OCOR 7&gt;; R 1&gt;1-4C linear, branched, saturated or unsaturated alkyl, optionally substituted one or more times, in (I), or 1-4C alkyl, benzyl, trifluoromethyl, hydroxy, benzyloxy. 1-3C alkoxy, chloro or fluoro in (II); R 2&gt; and R 3&gt;hydrogen or 1-4C alkyl (as for R 1&gt;) or together form an optionally substituted 4-7C cycloalkyl; R 9&gt;-R 1&gt; 3&gt;hydrogen, fluoro, chloro, bromo, iodo, (di)fluoromethyl, trifluoromethyl, hydroxy, thiol, OR 1&gt; 4&gt;, trifluoromethoxy, SR 1&gt; 4&gt;, NR 1&gt; 7&gt;R 1&gt; 8&gt;, (trifluoro)methyl- sulfinyl or -sulfonyl, cyano, COOR 1&gt; 4&gt;, nitro, CONR 1&gt; 7&gt;R 1&gt; 8&gt;, 1-6C alkyl (as above) or phenyl, optionally substituted one or more times; R 1&gt; 4&gt;1-6C alkyl, pyridyl, thienyl, thiazolyl, phenyl, benzyl, phenethyl (all optionally substituted one or more times), PO(O-1-4C alkyl)-2, COO1-5C alkyl, CONH(1-3C alkylphenyl), CO(1-5C)alkyl, COCHR 1&gt; 7&gt;-NHR 1&gt; 8&gt;, or CO-phenylene-R 1&gt; 5&gt;; R 1&gt; 5&gt;ortho-OCO(1-3C)alkyl, or meta- or para-CH 2N(R 1&gt; 6&gt;) 2; R 1&gt; 6&gt;1-4C alkyl or morpholino, and all alkyl in R 1&gt; 4&gt;-R 1&gt; 6&gt; are optionally substituted one or more times; R 1&gt; 7&gt; and R 1&gt; 8&gt;hydrogen, 1-6C alkyl (as above), phenyl, benzyl or phenethyl, all optionally substituted one or more times; R 1&gt; 0&gt; with either of R 9&gt; or R 1&gt; together : a OCH 2O, OCH 2CH 2O, OCH=CH, CH=CHO, CH=CMeO, OCMe=CH, (CH 2) 4 or OCH=CHO ring; proviso: in (III), when R 9&gt;, R 1&gt; 1&gt; and R 1&gt; 3&gt; are all hydrogen, one of R 1&gt; 0&gt; and R 1&gt; 2&gt; is hydrogen and the other methoxy, then X is nor hydroxy. ACTIVITY : Analgesic. In the mouse writhing test ( J. Pharmacol. Exp. Ther., 228 (1984) 1) animals were treated with (a) (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol (X); (b) rofecoxib (Y) or (c) a mixture of both at ratio 1:2, then after 30 minutes injected with acetic acid. The ED50 for reduction of writhing was 33 mg/kg for (X) alone and 60.1 mg/kg for (Y) alone, but only 23.3 mg/kg (compare 47 mg/kg for an additive effect) for the mixture. MECHANISM OF ACTION : None given.</abstract><oa>free_for_read</oa></addata></record>
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PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
title Uso de (1R,2R)-3-(3-dimetilamino-1-etil-2-metil-propil)-fenol para tratar el dolor inflamatorio
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