RU97106022A - LIGANDA X-RECEPTOR Retinoic acid - Google Patents

LIGANDA X-RECEPTOR Retinoic acid

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Publication number
RU97106022A
RU97106022A RU97106022/04A RU97106022A RU97106022A RU 97106022 A RU97106022 A RU 97106022A RU 97106022/04 A RU97106022/04 A RU 97106022/04A RU 97106022 A RU97106022 A RU 97106022A RU 97106022 A RU97106022 A RU 97106022A
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formula
tetramethyl
methyl
compound
tetrahydronaphthalen
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RU97106022/04A
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Russian (ru)
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RU2146241C1 (en
Inventor
Клаус Михаэль
Джон Лови Аллен
Мор Петер
Розенбергер Майкл
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Ф.Хоффманн-Ля Рош Аг
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Priority claimed from PCT/EP1995/003021 external-priority patent/WO1996005165A1/en
Publication of RU97106022A publication Critical patent/RU97106022A/en
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Claims (27)

1. Соединение формулы I
Figure 00000001

где необязательно присутствует связь, обозначенная пунктиром; и если связь, обозначенная пунктиром, присутствует, то R1 обозначает низший алкил и R2 обозначает галоген или R1 и R2 вместе с атомами углерода, к которым они присоединены, образуют 5-8-членное карбоциклической кольцо или 5-8-членное гетероциклическое кольцо, содержащее один атом серы, кислорода или азота, причем если кольцо является ароматическим, то связь, обозначенная пунктиром, представляет собой часть мезомерной системы или если связь, обозначенная пунктиром, отсутствует, то R1 и R2 вместе представляют собой метилен, образуя цис-замещенное циклопропиловое кольцо;
R3 обозначает гидрокси или низший алкокси;
R4 - R7 независимо друг от друга - водород или низший алкил;
Х обозначает группу (>CR8R9)n, где n = 1, 2 или 3 и R8, R9 независимо друг от друга - водород или низший алкил;
R10 - водород, алкил или алкокси;
и фармацевтически приемлемые соли карбоновой кислоты формулы I.1. The compound of formula I
Figure 00000001

where the link indicated by the dotted line is optionally present; and if the bond indicated by a dotted line is present, then R 1 is lower alkyl and R 2 is halogen or R 1 and R 2 together with the carbon atoms to which they are attached form a 5–8 membered carbocyclic ring or 5–8 membered heterocyclic ring containing one sulfur, oxygen or nitrogen atom, wherein when said ring is aromatic, the dotted bond represents a part of the mesomeric system or when the dotted bond is absent, then R 1 and R 2 taken together are methylene to form cis-substituted cyclopropyl ring;
R 3 is hydroxy or lower alkoxy;
R 4 - R 7 independently of one another is hydrogen or lower alkyl;
X represents a group (> CR 8 R 9 ) n , where n = 1, 2 or 3 and R 8 , R 9 independently of one another are hydrogen or lower alkyl;
R 10 is hydrogen, alkyl or alkoxy;
and pharmaceutically acceptable carboxylic acid salts of Formula I. 2. Соединение по п.1 формулы Ia
Figure 00000002

где R1 - низший алкил;
R2 - галоген
или R1 и R2 вместе с атомами углерода, к которому они присоединены, образуют 5-8-членное карбоциклическое кольцо или 5-8-членное гетероциклическое кольцо, содержащее один атом серы, кислорода или азота, причем если кольцо является ароматическим, то двойная связь между атомами углерода, присоединенными к R1 и R2, представляет собой часть мезомерной системы;
группы R3-R7, R10 и Х имеют значения, указанные для формулы I,
и фармацевтически приемлемые соли карбоновых кислот формулы Ia.2. The compound according to claim 1 of formula Ia
Figure 00000002

where R 1 is lower alkyl;
R 2 - halogen
or R 1 and R 2, together with the carbon atoms to which they are attached, form a 5–8 membered carbocyclic ring or a 5–8 membered heterocyclic ring containing one sulfur, oxygen or nitrogen atom, and if the ring is aromatic, then double the bond between carbon atoms attached to R 1 and R 2 is a part of the mesomeric system;
the groups R 3 -R 7 , R 10 and X have the meanings indicated for formula I,
and pharmaceutically acceptable carboxylic acid salts of formula Ia. 3. Соединение по п. 2, в которых R1 и R2 вместе с атомами углерода, к которым они присоединены, образуют 5-8-членное карбоциклическое кольцо.3. The compound according to claim 2, wherein R 1 and R 2, together with the carbon atoms to which they are attached, form a 5–8 membered carbocyclic ring. 4. Соединение по п. 2, которое представляет собой этиловый эфир (2Е, 4Е)-3-метил-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)циклопент-1-енил]пента-2,4-диеновой кислоты. 4. The compound according to claim 2, which is (2E, 4E) -3-methyl-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2 ethyl ester -yl) cyclopent-1-enyl] penta-2,4-diene acid. 5. Соединение по п.2, которое представляет собой (2Е,4Е)-3-метил-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)циклопент-1-енил] пента-2,4-диеновую кислоту. 5. The compound according to claim 2, which is (2E, 4E) -3-methyl-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl ) cyclopent-1-enyl] penta-2,4-diene acid. 6. Соединение по п.2, которое представляет собой (2Е,4Е)-3-метил-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)циклопент-1-енил] пента-2,4-диеновую кислоту. 6. The compound according to claim 2, which is (2E, 4E) -3-methyl-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl ) cyclopent-1-enyl] penta-2,4-diene acid. 7. Соединение по п.2, которое представляет собой (2Е,4Е)-3-метил-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)циклопент-1-енил] пента-2,4-диеновую кислоту. 7. The compound according to claim 2, which is (2E, 4E) -3-methyl-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl ) cyclopent-1-enyl] penta-2,4-diene acid. 8. Соединение по п. 2, в которых R1 и R2 вместе с атомами углерода, к которым они присоединены, образуют фениленовое кольцо.8. The compound according to claim 2, in which R 1 and R 2 together with the carbon atoms to which they are attached form a phenylene ring. 9. Соединение по п.8, которое представляет собой (2Е,4Е)-3-метил-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)циклопент-1-енил] пента-2,4-диеновую кислоту. 9. The compound according to claim 8, which is (2E, 4E) -3-methyl-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl ) cyclopent-1-enyl] penta-2,4-diene acid. 10. Соединение по .2, в которых присутствует связь, образованная пунктиром, и R1 и R2 вместе с атомами углерода, к которым они присоединены, образуют 5-8-членное ароматическое гетероциклическое кольцо.10. A compound according to .2, in which a bond formed by a dotted line is present, and R 1 and R 2, together with the carbon atoms to which they are attached, form a 5–8 membered aromatic heterocyclic ring. 11. Соединение по п.10, которое представляет собой (2Е,4Е)-3-метил-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)тиофен-2-ил] пента-2,4-диеновую кислоту. 11. The compound according to claim 10, which is (2E, 4E) -3-methyl-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl ) thiophene-2-yl] penta-2,4-diene acid. 12. Соединение по п.10, которое представляет собой (2Е,4Е)-3-метил-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)тиофен-2-ил] пента-2,4-диеновую кислоту. 12. The compound of claim 10, which is (2E, 4E) -3-methyl-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl ) thiophene-2-yl] penta-2,4-diene acid. 13. Соединение по п.10, которое представляет собой (2Е,4Е)-3-метил-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)тиофен-2-ил] пента-2,4-диеновую кислоту. 13. The compound of claim 10, which is (2E, 4E) -3-methyl-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl ) thiophene-2-yl] penta-2,4-diene acid. 14. Соединение по п.2, в котором R2 - галоген.14. The compound according to claim 2, in which R 2 is a halogen. 15. Соединение по п.14, которое представляет собой этиловый эфир (2Е,4Е, 6Е)-6-бром-3-метил-7-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)окта-2,4,6-триеновой кислоты. 15. The compound according to claim 14, which is (2E, 4E, 6E) -6-bromo-3-methyl-7- (5,5,8,8-tetramethyl-5,6,7,8- ethyl ester) tetrahydronaphthalen-2-yl) octa-2,4,6-trienoic acid. 16. Соединение по п.14, которое представляет собой (2Е,4Е,6Е)-6-бром-3-метил-7-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)окта-2,4,6-триеновую кислоту. 16. The compound of claim 14, which is (2E, 4E, 6E) -6-bromo-3-methyl-7- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene 2-yl) octa-2,4,6-trienoic acid. 17. Соединение по п.1, формулы Ib
Figure 00000003

где R3-R7 и X имеют значения, указанные для формулы I,
и фармацевтически приемлемые соли карбоновых кислот формулы Ib.17. The compound according to claim 1, formula Ib
Figure 00000003

where R 3 -R 7 and X have the meanings indicated for formula I,
and pharmaceutically acceptable carboxylic acid salts of Formula Ib. 18. Соединение по п.17, которое представляет собой (2Е,4Е)-3-метил-5-[(1RS, 2RS)-2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)циклопропил]пента-2,4-диеновую кислоту. 18. The compound of claim 17, which is (2E, 4E) -3-methyl-5 - [(1RS, 2RS) -2- (5,5,8,8-tetramethyl-5,6,7,8 -tetrahydronaphthalen-2-yl) cyclopropyl] penta-2,4-diene acid. 19. Соединение по п.17, которое представляет собой (2Е,4Е)-3-метил-5-[(1S, 2S)-2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)циклопропил] пента-2,4-диеновую кислоту. 19. The compound according to claim 17, which is (2E, 4E) -3-methyl-5 - [(1S, 2S) -2- (5,5,8,8-tetramethyl-5,6,7,8 -tetrahydronaphthalen-2-yl) cyclopropyl] penta-2,4-diene acid. 20. Соединение по п.17, которое представляет собой (2Е,4Е)-3-метил-5-[(1R, 2R)-2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидронафталин-2-ил)циклопропил] пента-2,4-диеновую кислоту. 20. The compound of claim 17, which is (2E, 4E) -3-methyl-5 - [(1R, 2R) -2- (5,5,8,8-tetramethyl-5,6,7,8 -tetrahydronaphthalen-2-yl) cyclopropyl] penta-2,4-diene acid. 21. Соединение формулы II
Figure 00000004

где A - формил, триарилфосфоний или ди-(низший алкокси)фосфинил;
R1, R2, R4 - R7 и R10 имеют значения, указанные в п.1.21. The compound of formula II
Figure 00000004

where A is formyl, triarylphosphonium or di- (lower alkoxy) phosphinyl;
R 1 , R 2 , R 4 - R 7 and R 10 have the meanings indicated in paragraph 1. 22. Фармацевтическая композиция, содержащая соединение формулы I по п.1 или фармацевтически приемлемые соли карбоновой кислоты формулы I и стандартные фармацевтические носители. 22. A pharmaceutical composition comprising a compound of formula I according to claim 1 or pharmaceutically acceptable carboxylic acid salts of formula I and standard pharmaceutical carriers. 23. Способ получения соединений формулы I по п.1 и фармацевтически приемлемых солей карбоновых кислот формулы I, способ, включающий взаимодействие соединения формулы II
Figure 00000005

с соединением формулы III
Figure 00000006

где А - формил и В обозначает триарилфосфоний или ди-(низший алкокси)фосфинил; или А обозначает триарилфосфоний или ди-(низший алкокси)фосфинил и В обозначает формил;
R - низший алкокси;
R1, R2, R4 - R7 и R10 имеют значения, указанные в п.1;
с получением соединения формулы I, где R3 - низший алкокси и, при необходимости, гидролиз низшей алкоксигруппы R3 в полученном таким образом соединении формулы I.23. The method of obtaining compounds of formula I according to claim 1 and pharmaceutically acceptable salts of carboxylic acids of formula I, the method comprising the interaction of the compounds of formula II
Figure 00000005

with a compound of formula III
Figure 00000006

where A is formyl and B stands for triarylphosphonium or di (lower alkoxy) phosphinyl; or A is triarylphosphonium or di (lower alkoxy) phosphinyl and B is formyl;
R is lower alkoxy;
R 1 , R 2 , R 4 - R 7 and R 10 have the meanings indicated in item 1;
with obtaining the compounds of formula I, where R 3 is lower alkoxy and, if necessary, the hydrolysis of the lower alkoxy group R 3 in the thus obtained compound of formula I. 24. Соединения формулы I и фармацевтически приемлемые соли карбоновой кислоты формулы I, полученные либо способом по п.23 либо очевидным химически эквивалентным ему способом. 24. The compounds of formula I and the pharmaceutically acceptable salts of carboxylic acid of formula I, obtained either by the method according to item 23 or by an obvious chemically equivalent method. 25. Применение соединений формулы I по п.1 или фармацевтически приемлемых солей карбоновой кислоты формулы I в качестве лекарств. 25. The use of compounds of the formula I according to claim 1 or pharmaceutically acceptable salts of carboxylic acid of the formula I as drugs. 26. Применение соединений формулы I по п.1 или фармацевтически приемлемых солей карбоновой кислоты формулы I для изготовления фармацевтических композиций для лечения угрей, псориаза или лейкемии. 26. The use of compounds of formula I according to claim 1 or pharmaceutically acceptable salts of carboxylic acid of formula I for the manufacture of pharmaceutical compositions for the treatment of acne, psoriasis or leukemia. 27. Новые соединения, композиции, способ и применение, в основном приведенные в настоящем описании. 27. New compounds, compositions, method and application, mainly described in the present description.
RU97106022A 1994-08-10 1995-07-29 Retinoic acid x-receptor ligands RU2146241C1 (en)

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EP94112461 1994-08-10
EP94112461.2 1995-07-05
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PCT/EP1995/003021 WO1996005165A1 (en) 1994-08-10 1995-07-29 Retinoic acid x-receptor ligands

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Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5466861A (en) * 1992-11-25 1995-11-14 Sri International Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors
US5968908A (en) * 1994-12-19 1999-10-19 American Cyanamid Company Restricted 9-cis retinoids
IL116259A (en) * 1994-12-19 2000-07-16 American Cyanamid Co Analogs of 9-cis retinoic acid and their use
US7115728B1 (en) 1995-01-30 2006-10-03 Ligand Pharmaceutical Incorporated Human peroxisome proliferator activated receptor γ
US5675033A (en) * 1995-06-06 1997-10-07 Allergan 2,4-pentadienoic acid derivatives having retinoid-like biological activity
US6028052A (en) * 1995-09-18 2000-02-22 Ligand Pharmaceuticals Incorporated Treating NIDDM with RXR agonists
DE69627193T2 (en) 1995-10-06 2004-01-29 Ligand Pharm Inc DIMER-SELECTIVE RXR MODULATORS AND METHOD FOR THEIR USE
FR2746101B1 (en) * 1996-03-14 1998-04-30 BICYCLIC-AROMATIC COMPOUNDS
EP0915825B1 (en) * 1996-06-21 2004-05-06 Allergan, Inc. Substituted tetrahydronaphthalene and dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
ATE253903T1 (en) 1996-12-11 2003-11-15 Dana Farber Cancer Inst Inc METHODS AND PHARMACEUTICAL COMPOSITIONS FOR PREVENTING THE GROWTH OF TUMOR CELLS CONTAINING A PPAR-GAMMA AGONIST AND A MAP KINASE INHIBITOR
US5919970A (en) * 1997-04-24 1999-07-06 Allergan Sales, Inc. Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity
DE69835441T2 (en) * 1997-11-12 2007-08-02 F. Hoffmann-La Roche Ag TREATMENT OF T-HELPER ZELL TYPE 2 MEDIATED IMMUNE DISEASES WITH RETINOID ANTAGONISTS
US6242196B1 (en) 1997-12-11 2001-06-05 Dana-Farber Cancer Institute Methods and pharmaceutical compositions for inhibiting tumor cell growth
AU4676999A (en) * 1998-06-12 1999-12-30 Ligand Pharmaceuticals, Inc. Treatment of anti-estrogen resistant breast cancer using rxr modulators
US6048873A (en) * 1998-10-01 2000-04-11 Allergan Sales, Inc. Tetrahdroquinolin-2-one 6 or 7-yl, tetrahdroquinilin-2-thione 6 or 7-yl pentadienoic acid and related derivatives having retinoid-like biological activity
US6403638B1 (en) 1998-10-01 2002-06-11 Allergan Sales, Inc. 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors
US6147224A (en) * 1998-10-01 2000-11-14 Allergan Sales, Inc. 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors
US6326397B1 (en) 1998-11-10 2001-12-04 Hoffman-La Roche Inc. Retinoid antagonists and use thereof
US6566372B1 (en) 1999-08-27 2003-05-20 Ligand Pharmaceuticals Incorporated Bicyclic androgen and progesterone receptor modulator compounds and methods
AU6941200A (en) 1999-08-27 2001-03-26 Ligand Pharmaceuticals Incorporated 8-substituted-6-trifluoromethyl-9-pyrido(3,2-g)quinoline compounds as androgen receptor modulators
CZ2002711A3 (en) 1999-08-27 2003-11-12 Ligand Pharmaceuticals Incorporated Androgenic receptor modulators, process of their preparation and their use
WO2001019770A2 (en) 1999-09-14 2001-03-22 Ligand Pharmaceuticals Incorporated Rxr modulators with improved pharmacologic profile
BRPI0107715B8 (en) 2000-01-21 2021-05-25 Novartis Ag pharmaceutical product comprising an inhibitor of dipeptidyl peptidase-iv and metformin, as well as uses of said pharmaceutical product and inhibitor of dipeptidyl peptidase-iv
US6313107B1 (en) 2000-08-29 2001-11-06 Allergan Sales, Inc. Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI
US6369225B1 (en) 2000-08-29 2002-04-09 Allergan Sales, Inc. Compounds having activity as inhibitors of cytochrome P450RAI
US6380256B1 (en) 2000-08-29 2002-04-30 Allergan Sales, Inc. Compounds having activity as inhibitors of cytochrome P450RAI
DE60204674T2 (en) * 2001-03-14 2006-05-18 Eli Lilly And Co., Indianapolis RETINOID X RECEPTOR MODULATORS
US6720423B2 (en) 2002-04-30 2004-04-13 Allergan, Inc. Dihydrobenzofuran and dihydrobenzothiophene 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors
AU2003286243A1 (en) * 2002-11-25 2004-06-18 Amedis Pharmaceuticals Ltd. Silicon compounds
US6759547B1 (en) * 2003-01-14 2004-07-06 Allergan, Inc. 5,6,7,8-tetrahydronaphthalen-2-yl 2,6-difluoroheptatrienoic acid derivatives having serum glucose reducing activity
US7019034B2 (en) * 2003-01-28 2006-03-28 Allergan, Inc. Compositions and methods for reducing serum glucose and triglyceride levels in diabetic mammals
US6759546B1 (en) 2003-02-04 2004-07-06 Allergan, Inc. 3,5-di-iso-propyl-heptatrienoic acid derivatives having serum glucose reducing activity
US6884820B2 (en) * 2003-04-03 2005-04-26 Allergan, Inc. 5,6,7,8-tetrahydronaphthalen-2-yl-7-fluoroalkyl-heptatrienoic acid derivatives having serum glucose reducing activity
US6734193B1 (en) 2003-06-03 2004-05-11 Allergan, Inc. (1,2,3,4-tetrahydroquinolin-8-yl)-heptatrienoic acid derivatives having serum glucose reducing activity
CA2535260A1 (en) * 2003-08-07 2005-02-17 Allergan, Inc. Method for treating cachexia with retinoid ligands
US6887896B1 (en) 2003-10-29 2005-05-03 Allergan, Inc. 7-[(7-Alkoxy)-chrom-3-en-6-yl]-heptatrienoic acid and 7-[(3-alkoxy)-5,6-dihydronaphthalen-2-yl]-heptatrienoic acid derivatives having serum glucose reducing activity
US9050310B2 (en) 2004-06-25 2015-06-09 Minas Theodore Coroneo Treatment of ocular lesions
WO2007048510A1 (en) * 2005-10-25 2007-05-03 Werner Bollag Rxr agonists and antagonists, alone or in combination with ppar ligands, in the treatment of metabolic and cardiovascular diseases
US20070185055A1 (en) * 2006-02-06 2007-08-09 Guang Liang Jiang Method for treating cachexia with retinoid ligands
WO2009102789A2 (en) * 2008-02-15 2009-08-20 Wyeth Use of rxr agonists for the treatment of osteroarthritis
JP5877466B2 (en) * 2012-02-29 2016-03-08 国立大学法人 岡山大学 Terpenoid-derived retinoid compounds
US20160263189A1 (en) 2013-10-23 2016-09-15 Acadia Pharmaceuticals Inc. Treatment of a neurodegenerative disease or disorder
US11045441B2 (en) 2015-10-13 2021-06-29 Wisconsin Alumni Research Foundation Use of retinoic acid and analogs thereof to treat central neural apneas
WO2019064109A1 (en) * 2017-09-28 2019-04-04 Johnson & Johnson Consumer Inc. Cosmetic compositions and method of treating the skin
CN113302206A (en) 2018-11-26 2021-08-24 戴纳立制药公司 Methods of treating lipid metabolism disorders

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH651007A5 (en) * 1982-06-24 1985-08-30 Hoffmann La Roche POLYEN CONNECTIONS.
EP0170105B1 (en) * 1984-07-07 1990-10-17 Koichi Prof. Dr. Shudo Benzoic acid derivatives
AU675430B2 (en) * 1992-04-22 1997-02-06 Ligand Pharmaceuticals Incorporated Compounds having selectivity for retinoid X receptors
US5466861A (en) * 1992-11-25 1995-11-14 Sri International Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors
WO1995004036A1 (en) * 1993-01-11 1995-02-09 Ligand Pharmaceuticals Inc. Compounds having selective activity for retinoid x receptors, and means for modulation of processes mediated by retinoid x receptors
US5344959A (en) * 1993-05-18 1994-09-06 Allergan, Inc. Tetrahydronaphthyl and cyclopropyl substituted 1,3-butadienes having retinoid-like activity

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