RU97106174A - NEW RETINOIDS - Google Patents
NEW RETINOIDSInfo
- Publication number
- RU97106174A RU97106174A RU97106174/04A RU97106174A RU97106174A RU 97106174 A RU97106174 A RU 97106174A RU 97106174/04 A RU97106174/04 A RU 97106174/04A RU 97106174 A RU97106174 A RU 97106174A RU 97106174 A RU97106174 A RU 97106174A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compounds according
- enyl
- hydroxy
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- -1 4-hydroxy-2,6,6-trimethylcyclohex-1-enyl Chemical group 0.000 claims 4
- 230000037380 skin damage Effects 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- 206010000496 Acne Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drugs Drugs 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 230000003211 malignant Effects 0.000 claims 2
- 230000001575 pathological Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 201000004681 psoriasis Diseases 0.000 claims 2
- FRMQNYSFAZVOGJ-CCKACSLISA-N (2Z,4E,6E,8E)-9-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid Chemical compound OC(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C FRMQNYSFAZVOGJ-CCKACSLISA-N 0.000 claims 1
- FRMQNYSFAZVOGJ-WTADKEDRSA-N (2Z,4E,6E,8E)-9-[(4S)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid Chemical compound OC(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@H](O)CC1(C)C FRMQNYSFAZVOGJ-WTADKEDRSA-N 0.000 claims 1
- XRNPHZPFAWLRNJ-UHFFFAOYSA-N 2-hydroxy-3-methyl-2H-furan-5-one Chemical compound CC1=CC(=O)OC1O XRNPHZPFAWLRNJ-UHFFFAOYSA-N 0.000 claims 1
- YOFBBAJVETYSCH-IWRFDTMXSA-N 4-Oxo-13-cis-retinoate Chemical compound OC(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C YOFBBAJVETYSCH-IWRFDTMXSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000002441 reversible Effects 0.000 claims 1
Claims (1)
где X обозначает оксогруппу или группу OR1 в положении 4 или 5;
R1 обозначает водород, алкил или ацил; и
R2 обозначает водород или алкил; связи, обозначенные пунктиром, являются необязательными и 3,4-двойная связь может присутствовать только в том случае, когда X находится в положении 5;
а также фармацевтически приемлемые соли карбоновых кислот формулы I.1. Compounds of General Formula
where X denotes the oxo group or the group OR 1 in position 4 or 5;
R 1 is hydrogen, alkyl or acyl; and
R 2 is hydrogen or alkyl; the bonds indicated by the dotted line are optional and a 3,4-double bond can be present only when X is in position 5;
as well as pharmaceutically acceptable salts of carboxylic acids of formula I.
3. Соединения по п.1 формулы
4. Соединения по п.1 формулы
5. (2Z, 4E, 6E, 8E)-(R)-9-(4-гидрокси-2,6,6-триметилциклогекс-1-енил)-3,7-диметилнона-2,4,6,8-тетраеновая кислота.2. Compounds according to claim 1 of the formula
3. Compounds according to claim 1 of the formula
4. Compounds according to claim 1 of the formula
5. (2Z, 4E, 6E, 8E) - (R) -9- (4-hydroxy-2,6,6-trimethylcyclohex-1-enyl) -3,7-dimethylnon-2,4,6,8- tetraenoic acid.
9. Соединения по п.1 формулы
10. (2Z, 4E, 6E, 8E)-9-(5-гидрокси-2,6,6-триметилциклогекс-1-енил)-3,7-диметилнона-2,4,6,8-тетраеновая кислота.8. Compounds according to claim 1 of the formula
9. Compounds according to claim 1 of the formula
10. (2Z, 4E, 6E, 8E) -9- (5-hydroxy-2,6,6-trimethylcyclohex-1-enyl) -3,7-dimethylnone-2,4,6,8-tetraenoic acid.
12. (2Z, 4E, 6E, 8E)-9-(5-оксо-2,6,6-триметилциклогекса-1,3-диенил)-3,7-диметилнона-2,4,6,8-тетраеновая кислота.11. Compounds according to claim 1 of the formula
12. (2Z, 4E, 6E, 8E) -9- (5-oxo-2,6,6-trimethylcyclohexa-1,3-dienyl) -3,7-dimethylnone-2,4,6,8-tetraenoic acid .
15. (2Z, 4E, 6E)-(R)-9-(4-гидрокси-2,6,6-триметилциклогекс-1-енил)-3,7-диметилнона-2,4,6-триен-8-иновая кислота.14. Compounds according to claim 1 of the formula
15. (2Z, 4E, 6E) - (R) -9- (4-hydroxy-2,6,6-trimethylcyclohex-1-enyl) -3,7-dimethylnon-2,4,6-triene-8- inic acid
где A обозначает фенил или замещенный фенил;
Y- - обозначает анион;
X и связи, обозначенные пунктиром, имеют указанные выше значения,
с 5-гидрокси-4-метил-5H-фуран-2-оном в присутствии основания, изомеризацию присутствующих в продукте реакции изомеров, в которых образовавшаяся в результате взаимодействия двойная связь C=C имеет цис-конфигурацию, в транс-изомеры и при необходимости обработку полученного продукта взаимодействия формулы I в соответствии с одной или нескольким из следующих реакций: а) этерификацией карбоксильной или гидроксильной группы в сложный эфир; б) этерификацией гидроксильной группы в простой эфир; в) окислением гидроксильной группы до оксогруппы; г) восстановлением оксогруппы до гидроксильной группы; д) стерическим обращением гидроксильной группы; е) превращением карбоксильной группы в соль.19. The method of obtaining compounds of General formula I and their pharmaceutically acceptable salts, including the interaction of the compounds of General formula
where A denotes phenyl or substituted phenyl;
Y - - denotes anion;
X and the bonds indicated by the dotted line have the meanings specified above,
with 5-hydroxy-4-methyl-5H-furan-2-one in the presence of a base, isomerization of isomers present in the reaction product, in which the C = C double bond resulting from the reaction has the cis configuration, into the trans isomer and, if necessary, processing the resulting product of the interaction of the formula I in accordance with one or more of the following reactions: a) by esterifying the carboxyl or hydroxyl group into an ester; b) esterification of the hydroxyl group into an ether; c) oxidation of a hydroxyl group to an oxo group; d) reduction of the oxo group to a hydroxyl group; e) steric reversal of the hydroxyl group; e) by converting the carboxyl group to a salt.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96105849.2 | 1996-04-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU97106174A true RU97106174A (en) | 1999-04-27 |
| RU2173683C2 RU2173683C2 (en) | 2001-09-20 |
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