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1. 发明授权

US06344463B1 Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity 失效
标题翻译：具有异双环基团的二取代乙炔和具有类视黄醇样活性的杂芳族或苯基
公开(公告)号：US06344463B1
公开(公告)日：2002-02-05
申请号：US09611889
申请日：2000-07-07
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： A61K31352
CPC分类号： C07D335/06 , C07D215/12 , C07D311/58 , C07D401/06 , C07D405/06 , C07D407/06 , C07D409/06
摘要： Compounds of the formula where R1 and R2, independently are alkyl groups having 2 to 8 carbons; R3 is hydrogen or lower alkyl; X is S, O or N—R4 where R4 is hydrogen or lower alkyl; Y is phenyl or pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, and pyrazinyl; A is (CH2)n where n is 0-5, or lower branched chain alkyl, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a salt thereof, COOR5, CONR6R7, —CH2OH, CH2OR8, CH2OCOR8, CHO, CH(OR9)2, CHOR10O, —COR11, CR11(OR9)2, or CR11OR10O, where R5 is alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or R5 is phenyl or lower alkylphenyl, R6 and R7 independently are hydrogen, alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or phenyl or lower alkylphenyl, R8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R9 is lower alkyl, R10 is divalent alkyl radical of 2-5 carbons and R11 is alkyl, cycloalkyl or alkenyl containing 1 to 5 carbons, have retinoic acid like activity.
摘要翻译：式R 1和R 2的化合物独立地是具有2至8个碳的烷基; R3是氢或低级烷基; X是S，O或N-R4，其中R4是氢或低级烷基; Y是苯基或吡啶基，噻吩基，呋喃基，哒嗪基，嘧啶基和吡嗪基; A是（CH 2）n，其中n是0-5，或低级支链烷基，具有2-6个碳的烯基和1或2个双键，具有2至6个碳的炔基和1或2个三键; B是氢，COOH或其盐，COOR5，CONR6R7，-CH2OH，CH2OR8，CH2OCOR8，CHO，CH（OR9）2，CHOR10O，-COR11，CR11（OR9）2或CR11OR10O，其中R5是1〜 10个碳原子或5至10个碳原子的环烷基，或R5为苯基或低级烷基苯基，R6和R7独立地为氢，1至10个碳原子的烷基或5至10个碳原子的环烷基，或苯基或低级烷基苯基，R8为烷基 1〜10个碳原子，苯基或低级烷基苯基，R9为低级烷基，R10为2-5个碳原子的二价烷基，R11为含1〜5个碳原子的烷基，环烷基或烯基，具有视黄酸类活性。

2. 发明授权

US5414007A Acetylenes disubstituted with a thiazole group and a substituted phenyl group having retinoid like activity 失效
标题翻译：用噻唑基取代的乙炔和具有类视黄醇样活性的取代苯基
公开(公告)号：US5414007A
公开(公告)日：1995-05-09
申请号：US126952
申请日：1993-09-24
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： C07D213/80 , A61K31/425
CPC分类号： C07D213/80
摘要： Retinoid like activity is exhibited by compounds of the formula ##STR1## where R.sub.1 -R.sub.3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR.sub.4 or OR.sub.4 where R.sub.4 is lower alkyl, cycloalkyl or lower alkenyl; Y is selected from a group consisting of pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; E is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH.sub.2).sub.n where n is 0-5, and Z is H, OH, OR.sub.5, OCOR.sub.5, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH, CH.sub.2 OR.sub.6, CH.sub.2 OCOR.sub.6, or --CHO, CH(OR.sub.7).sub.2, CHOR.sub.8 O, or COR.sub.9, CR.sub.9 (OR.sub.7).sub.2, CR.sub.9 OR.sub.8 O where R.sub.5 is lower alkyl, phenyl or lower alkylphenyl, R.sub.6 is lower alkyl, phenyl or lower alkylphenyl, R.sub.7 is lower alkyl, R.sub.8 is a divalent alkyl radical of 2-5 carbons, and R.sub.9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
摘要翻译：其中R 1 -R 3独立地是氢，低级烷基，环烷基或低级链烯基，A和B独立地是氢，低级烷基，环烷基，低级烯基，SR4或OR4，其中R4是低级烷基，环烷基或低级烯基; Y选自哒嗪基，嘧啶基，吡嗪基，噻唑基或恶唑基; E为低级链烯基，低级炔基，低级环烷基，低级支链烷基，或其特征为式（CH2）n，其中n为0-5，Z为H，OH，OR5，OCOR5，-COOH或药学上可接受的其盐，酯或酰胺，-CH 2 OH，CH 2 OR 6，CH 2 OCOR 6或-CHO，CH（OR 7）2，CHOR 8 O或COR 9，CR 9（OR 7）2，CR 9OR 8 O，其中R 5为低级烷基，苯基或低级烷基苯基，烷基，苯基或低级烷基苯基，R7为低级烷基，R8为2-5个碳原子的二价烷基，R9为含有1至5个碳原子的烷基，环烷基或链烯基。

3. 发明授权

US5246962A Acetylenes disubstituted with a heteroaromatic group and a tetralin group and having retinoid like activity 失效
标题翻译：用杂芳基和四氢化萘基二取代并具有类视黄醇样活性的乙炔
公开(公告)号：US5246962A
公开(公告)日：1993-09-21
申请号：US947681
申请日：1992-09-21
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： C07D213/80
CPC分类号： C07D213/80
摘要： Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
摘要翻译：类视黄醇样活性由式（Ⅰ）的化合物表现，其中R是氢或低级烷基; A是吡啶基，噻吩基，呋喃基，哒嗪基，嘧啶基或吡嗪基; n为0-5; 和B是H，-COOH或其酯或酰胺，-CH 2 OH或其醚或酯衍生物，或-CHO或其缩醛衍生物，或-COR1或其缩酮衍生物，其中R1是 - （CH2）mCH3，其中 m为0-4; 或其药学上可接受的盐。

4. 发明授权

US5231113A Tetralin esters of phenols or benzoic acids having retinoid like activity 失效
标题翻译：具有类视黄醇活性的苯酚或苯甲酸的四氢化萘酯
公开(公告)号：US5231113A
公开(公告)日：1993-07-27
申请号：US894122
申请日：1992-06-04
申请人： Roshantha A. S. Chandraratna , Robert J. Weinkam
发明人： Roshantha A. S. Chandraratna , Robert J. Weinkam
IPC分类号： C07C69/773 , C07C69/82 , C07C69/90
CPC分类号： C07C69/82 , C07C2102/10
摘要： Retinoid-like activity is exhibited by compounds of the formula ##STR1## where the R groups are independently hydrogen, or lower alkyl; A is --C(O)O--, --OC(O)--, --C(O)S--, or --SC(O)--; n is 0-5; and Z is H, --COB where B is --OH or a pharmaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is hydrogen or lower alkyl, or Z is --OE where E is hydrogen or an ether-forming group or --COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is --COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.
摘要翻译：类视黄醇样活性由式（Ⅰ）的化合物表现，其中R基团独立地为氢或低级烷基; A是-C（O）O-，-OC（O） - ， - C（O）S - 或-SC（O） - ; n为0-5; 和Z是H，-COB，其中B是-OH或药学上可接受的盐，或B是-OR1，其中R1是酯形成基团，或B是-N（R）2，其中R是氢或低级烷基，或 Z为-OE，其中E为氢或醚形成基团或-COR2，其中R2为氢，低级烷基，苯基或低级烷基苯基，或Z为-CHO或其缩醛衍生物，或Z为-COR3，其中R3为 - （CH 2）m CH 3，其中m为0-4，n和m的和不超过4。

5. 发明授权

US4927947A Ethynylheteroaromatic-acids having retinoic acid-like activity 失效
标题翻译：具有视黄酸样活性的乙炔基异烟酸
公开(公告)号：US4927947A
公开(公告)日：1990-05-22
申请号：US303864
申请日：1989-01-30
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： C07D213/30 , C07D213/48 , C07D213/51 , C07D213/55 , C07D213/80 , C07D307/34 , C07D307/54 , C07D307/68 , C07D333/24 , C07D333/38
CPC分类号： C07D213/30 , C07C403/02 , C07D213/48 , C07D213/51 , C07D213/55 , C07D213/80 , C07D307/54 , C07D307/68 , C07D333/24 , C07D333/38 , C07C2101/16
摘要： Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.
摘要翻译：其中A是吡啶基，呋喃基，噻吩基，哒嗪基，嘧啶基或吡嗪基的化合物，表现出类视黄醇样活性。 n为0-5; 和B是H，-COOH及其酯，酰胺和药学上可接受的盐，-CHO及其缩醛衍生物，-COR1及其缩酮衍生物，其中R1是 - （CH2）nCH3，其中n定义如上，或-CH 2 OH及其醚和酰基酯衍生物; 或药学上可接受的盐。

6. 发明授权

US4810804A Acetylenes disubstituted with a phenyl group and a heterobicyclic group having retinoid-like activity 失效
标题翻译：用苯基和具有类视黄醇样活性的杂双环基团二取代的乙炔
公开(公告)号：US4810804A
公开(公告)日：1989-03-07
申请号：US31476
申请日：1987-03-26
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： A61K31/35 , A61K31/352 , A61K31/38 , A61K31/382 , A61K31/47 , A61P17/00 , A61P27/02 , A61P29/00 , A61P35/00 , A61P37/00 , A61P43/00 , C07D215/06 , C07D215/12 , C07D215/14 , C07D311/58 , C07D335/06 , A61K31/335
CPC分类号： C07D335/06 , C07D215/12 , C07D215/14 , C07D311/58
摘要： Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O or NR.sub.1 where R.sub.1 is hydrogen or lower alkyl; n is 0-5; R is H or lower alkyl and A is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.2 or a ketal derivative thereof where R.sub.2 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt.

7. 发明授权

US6090826A Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity 失效
标题翻译：具有异双环基团的二取代乙炔和具有类视黄醇样活性的杂芳族或苯基
公开(公告)号：US6090826A
公开(公告)日：2000-07-18
申请号：US30351
申请日：1998-02-25
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： A61K31/35 , A61K31/352 , A61K31/38 , A61K31/382 , A61K31/44 , A61K31/443 , A61K31/4433 , A61K31/47 , A61K31/50 , A61K31/505 , A61P9/10 , A61P13/02 , A61P15/00 , A61P17/00 , A61P27/02 , A61P29/00 , A61P35/00 , A61P37/06 , C07D215/12 , C07D215/14 , C07D311/58 , C07D335/06 , C07D401/06 , C07D405/06 , C07D407/06 , C07D409/06 , A61K31/335 , A61K31/395 , C07D211/72
CPC分类号： C07D335/06 , C07D215/12 , C07D311/58 , C07D401/06 , C07D405/06 , C07D407/06 , C07D409/06
摘要： Compounds of the formula ##STR1## where R.sub.1 and R.sub.2, independently are alkyl groups having 2 to 8 carbons; R.sub.3 is hydrogen or lower alkyl; X is S, O or N--R.sub.4 where R.sub.4 is hydrogen or lower alkyl; Y is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, and pyrazinyl; A is (CH.sub.2).sub.n where n is 0-5, or lower branched chain alkyl, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a salt thereof, COOR.sub.5, CONR.sub.6 R.sub.7, --CH.sub.2 OH, CH.sub.2 OR.sub.8, CH.sub.2 OCOR.sub.8, CHO, CH(OR.sub.9).sub.2, CHOR.sub.10 O, --COR.sub.11, CR.sub.11 (OR.sub.9).sub.2, or CR.sub.11 OR.sub.10 O, where R.sub.5 is alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or R.sub.5 is phenyl or lower alkylphenyl, R.sub.6 and R.sub.7 independently are hydrogen, alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.9 is lower alkyl, R.sub.10 is divalent alkyl radical of 2-5 carbons and R.sub.11 is alkyl, cycloalkyl or alkenyl containing 1 to 5 carbons, have retinoic acid like activity.
摘要翻译：下式的化合物其中R 1和R 2独立地是具有2至8个碳的烷基; R3是氢或低级烷基; X是S，O或N-R4，其中R4是氢或低级烷基; Y是吡啶基，噻吩基，呋喃基，哒嗪基，嘧啶基和吡嗪基; A是（CH 2）n，其中n是0-5，或低级支链烷基，具有2-6个碳的烯基和1或2个双键，具有2至6个碳的炔基和1或2个三键; B是氢，COOH或其盐，COOR5，CONR6R7，-CH2OH，CH2OR8，CH2OCOR8，CHO，CH（OR9）2，CHOR10O，-COR11，CR11（OR9）2或CR11OR10O，其中R5是1〜 10个碳原子或5至10个碳原子的环烷基，或R5为苯基或低级烷基苯基，R6和R7独立地为氢，1至10个碳原子的烷基或5至10个碳原子的环烷基，或苯基或低级烷基苯基，R8为烷基 1〜10个碳原子，苯基或低级烷基苯基，R9为低级烷基，R10为2-5个碳原子的二价烷基，R11为含1〜5个碳原子的烷基，环烷基或烯基，具有视黄酸类活性。

8. 发明授权

US5677451A Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity 失效
标题翻译：具有异双环基团的二取代乙炔和具有类视黄醇样活性的杂芳族或苯基
公开(公告)号：US5677451A
公开(公告)日：1997-10-14
申请号：US466003
申请日：1995-06-06
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： A61K31/35 , A61K31/352 , A61K31/38 , A61K31/382 , A61K31/44 , A61K31/443 , A61K31/4433 , A61K31/47 , A61K31/50 , A61K31/505 , A61P9/10 , A61P13/02 , A61P15/00 , A61P17/00 , A61P27/02 , A61P29/00 , A61P35/00 , A61P37/06 , C07D215/12 , C07D215/14 , C07D311/58 , C07D335/06 , C07D401/06 , C07D405/06 , C07D407/06 , C07D409/06 , C07D215/00 , C07D409/00 , C07D419/00
CPC分类号： C07D335/06 , C07D215/12 , C07D311/58 , C07D401/06 , C07D405/06 , C07D407/06 , C07D409/06
摘要： Compounds of the formula ##STR1## where R.sub.1 and R.sub.2, independently are alkyl groups having 2 to 8 carbons; R.sub.3 is hydrogen or lower alkyl; X is S, O or N-R.sub.4 where R.sub.4 is hydrogen or lower alkyl; Y is phenyl or pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, and pyrazinyl; A is (CH.sub.2).sub.n where n is 0-5, or lower branched chain alkyl, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a salt thereof, COOR.sub.5, CONR.sub.6 R.sub.7, --CH.sub.2 OH, CH.sub. 2OR.sub.8, CH.sub.2 OCOR.sub.8, CHO, CH(OR.sub.9).sub.2, CHOR.sub.10 O, --COR.sub.11, CR.sub.11 (OR.sub.9).sub.2, or CR11OR.sub.10 O, where R.sub.5 is alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or R.sub.5 is phenyl or lower alkylphenyl, R.sub.6 and R.sub.7 independently are hydrogen, alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.9 is lower alkyl, R.sub.10 is divalent alkyl radical of 2-5 carbons and R.sub.11 is alkyl, cycloalkyl or alkenyl containing 1 to 5 carbons, have retinoic acid like activity.
摘要翻译：其中R 1和R 2独立地为具有2至8个碳原子的烷基; R3是氢或低级烷基; X是S，O或N-R4，其中R4是氢或低级烷基; Y是苯基或吡啶基，噻吩基，呋喃基，哒嗪基，嘧啶基和吡嗪基; A是（CH 2）n，其中n是0-5，或低级支链烷基，具有2-6个碳的烯基和1或2个双键，具有2至6个碳的炔基和1或2个三键; B是氢，COOH或其盐，COOR5，CONR6R7，-CH2OH，CH2OR8，CH2OCOR8，CHO，CH（OR9）2，CHOR10O，-COR11，CR11（OR9）2或CR11OR10O，其中R5是1〜 10个碳原子或5至10个碳原子的环烷基，或R5为苯基或低级烷基苯基，R6和R7独立地为氢，1至10个碳原子的烷基或5至10个碳原子的环烷基，或苯基或低级烷基苯基，R8为烷基 1〜10个碳原子，苯基或低级烷基苯基，R9为低级烷基，R10为2-5个碳原子的二价烷基，R11为含1〜5个碳原子的烷基，环烷基或烯基，具有视黄酸类活性。

9. 发明授权

US5466690A Acetylenes disubstituted with a heteroaromatic group and a tetralin group and having retinoid like activity 失效
标题翻译：用杂芳基和四氢化萘基二取代并具有类视黄醇样活性的乙炔
公开(公告)号：US5466690A
公开(公告)日：1995-11-14
申请号：US276385
申请日：1994-07-18
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： C07D237/08 , A61K31/34 , A61K31/341 , A61K31/38 , A61K31/381 , A61K31/44 , A61K31/4418 , A61K31/495 , A61P17/00 , A61P27/02 , A61P27/14 , A61P29/00 , A61P37/08 , C07D213/06 , C07D213/30 , C07D213/48 , C07D213/50 , C07D213/55 , C07D213/65 , C07D213/80 , C07D213/81 , C07D237/24 , C07D239/26 , C07D239/28 , C07D241/12 , C07D241/24 , C07D307/54 , C07D307/68 , C07D333/12 , C07D333/14 , C07D333/24 , A61K31/415 , C07D233/06
CPC分类号： C07D213/80
摘要： Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
摘要翻译：类视黄醇样活性由式（Ⅰ）的化合物表现，其中R是氢或低级烷基; A是吡啶基，噻吩基，呋喃基，哒嗪基，嘧啶基或吡嗪基; n为0-5; 和B是H，-COOH或其酯或酰胺，-CH 2 OH或其醚或酯衍生物，或-CHO或其缩醛衍生物，或-COR1或其缩酮衍生物，其中R1是 - （CH2）mCH3，其中 m为0-4; 或其药学上可接受的盐。

10. 发明授权

US5455265A Method of treatment with compounds having selective agonist-like activity on RXR retinoid receptors 失效
公开(公告)号：US5455265A
公开(公告)日：1995-10-03
申请号：US16404
申请日：1993-02-11
申请人： Roshantha A. S. Chandraratna
发明人： Roshantha A. S. Chandraratna
IPC分类号： C07D333/38 , A61K31/19 , A61K31/34 , A61K31/341 , A61K31/38 , A61K31/381 , A61K45/00 , A61P3/00 , A61P9/10 , A61P17/00 , A61P37/06 , C07C13/48 , C07C33/38 , C07C33/50 , C07C35/21 , C07C35/52 , C07C47/238 , C07C47/24 , C07C47/277 , C07C49/225 , C07C49/237 , C07C49/255 , C07C61/39 , C07C69/618 , C07C69/753 , C07C69/76 , C07C233/02 , C07C233/58 , C07D307/68 , C07F9/54
CPC分类号： A61K31/19 , A61K31/34 , A61K31/38
摘要： Process of treatment of mammals, including humans to treat diseases or conditions of the type which are normally treated with retinoid-like compounds is disclosed, with pharmaceutical compositions containing an active compound which is a selective agonist of the RXR retinoid receptor sites in preference to the RAR retinoid receptor sites. A compound is defined to be a selective agonist of the RXR receptor site if the compound is at least approximately ten times more effective as an agonist in the RXR receptor sites than in the RAR receptor sites.

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