Use of jasmonate ester derivatives for treating benign hyperproliferative skin disorders
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-215/24
C07C-057/26
출원번호
US-0497020
(2014-09-25)
등록번호
US-9284252
(2016-03-15)
발명자
/ 주소
Herzberg, Max
Revah, Frederic
출원인 / 주소
SEPAL PHARMA LTD.
대리인 / 주소
Rothwell, Figg, Ernst & Manbeck, P.C.
인용정보
피인용 횟수 :
0인용 특허 :
18
초록▼
The present invention relates to methods of treating benign hyperproliferative diseases of the epidermis by administering a composition comprising at least one jasmonate ester derivative. In particular, the present invention provides jasmonate ester derivatives as potent compounds useful for the tre
The present invention relates to methods of treating benign hyperproliferative diseases of the epidermis by administering a composition comprising at least one jasmonate ester derivative. In particular, the present invention provides jasmonate ester derivatives as potent compounds useful for the treatment of disorders such as actinic keratoses with reduced side effects.
대표청구항▼
1. A method of treating a benign hyperproliferative skin disorder in a subject in need thereof, comprising the step of decreasing proliferation of abnormal hyperproliferative benign epidermal cells in said subject by exposing said cells to a proliferation decreasing-effective amount of a pharmaceuti
1. A method of treating a benign hyperproliferative skin disorder in a subject in need thereof, comprising the step of decreasing proliferation of abnormal hyperproliferative benign epidermal cells in said subject by exposing said cells to a proliferation decreasing-effective amount of a pharmaceutical composition comprising at least one jasmonate ester of formula III, so as to decrease proliferation of said hyperproliferative benign epidermal cells: whereinA is COR1;R1 is quinolinyloxy;R2 is selected from the group consisting of hydrogen, unsubstituted or substituted C1-C12 alkyl, unsubstituted or substituted C3-C8 cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, OR8, oxo and NR9aR9b;R3, R4, R5, R6 and R7 are each independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C1-C12 alkyl, unsubstituted or substituted C1-C12 haloalkyl, unsubstituted or substituted C3-C8 cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, OR8 and NR9aR9b,or R5 and R6 together with the carbons to which they are attached form a C3-C8 cycloalkyl or a C3-C8 cycloalkyl substituted by halo;or one of R5 and R6 represents an oxygen atom which is bonded to C6, thereby forming an oxygen-containing 6 or 5 membered heterocyclic ring, respectively;wherein the bond between C9 and C10 can be a single or double bond;R8, R9a and R9b are each independently selected from the group consisting of hydrogen, unsubstituted or substituted C1-C12 alkyl, unsubstituted or substituted C3-C8 cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, glucosyl, or R9a and R9b can together with the nitrogen to which they are attached form an unsubstituted or substituted heterocyclic or heteroaromatic ring optionally containing one or more additional heteroatom selected from O, N and S; andn is selected from 0, 1 and 2;including salts, hydrates, solvates, polymorphs, optical isomers, geometrical isomers, enantiomers, diastereomers, and mixtures thereof. 2. The method according to claim 1, wherein the quinolinyloxy is unsubstituted or substituted with one or more alkyl groups. 3. The method according to claim 1, wherein R2 is oxo. 4. The method according to claim 1, wherein the bond between C9 and C10 is a double bond, and R3, R4, R5, R6 and R7 are each hydrogen. 5. The method according to claim 1, wherein the bond between C9 and C10 is a single bond, and R3, R4, R5, R6 and R7 are each hydrogen. 6. The method according to claim 1, wherein the jasmonate ester is represented by the structure of formula C: 7. The method according to claim 1, wherein the composition is formulated for topical administration. 8. The method according to claim 7, wherein the composition is in a form selected from the group consisting of an ointment, a cream a lotion, a foam and a gel. 9. The method according to claim 1, wherein the benign hyperproliferative skin disorder is selected from the group consisting of psoriasis, keratoses, actinic keratosis, common warts, genital warts, keratoacanthoma, seborrhoic keratosis, seborrhea and ichthyosis. 10. The method according to claim 9, wherein the keratoses are selected from the group consisting of actinic keratosis, hypertrophic actinic keratosis, Bowenoid actinic keratosis, arsenical keratosis, hydrocarbon keratosis, thermal keratosis, radiation keratosis, chronic scar keratosis, viral keratosis, actinic cheilitis, Bowen's disease, erythroplaquia of queyrat, oral erythroplaquia, leukoplakia or intraepidermal epithelialoma. 11. The method according to claim 9, wherein the skin disorder is actinic keratosis. 12. A method of treating actinic keratosis in a subject in need thereof, comprising the step of decreasing proliferation of abnormal hyperproliferative epidermal cells in said subject by exposing said cells to a proliferation decreasing-effective amount of a pharmaceutical composition comprising at least one jasmonate ester of formula III, so as to decrease proliferation of said hyperproliferative benign epidermal cells: whereinA is COR1;R1 is quinolinyloxy;R2 is selected from the group consisting of hydrogen, unsubstituted or substituted C1-C12 alkyl, unsubstituted or substituted C3-C8 cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, OR8, oxo and NR9aR9b;R3, R4, R5, R6 and R7 are each independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C1-C12 alkyl, unsubstituted or substituted C1-C12 haloalkyl, unsubstituted or substituted C3-C8 cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, OR8 and NR9aR9b,or R5 and R6 together with the carbons to which they are attached form a C3-C8 cycloalkyl or a C3-C8 cycloalkyl substituted by halo;or one of R5 and R6 represents an oxygen atom which is bonded to C6, thereby forming an oxygen-containing 6 or 5 membered heterocyclic ring, respectively;wherein the bond between C9 and C10 can be a single or double bond;R8, R9a and R9b are each independently selected from the group consisting of hydrogen, unsubstituted or substituted C1-C12 alkyl, unsubstituted or substituted C3-C8 cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, glucosyl, or R9a and R9b can together with the nitrogen to which they are attached form an unsubstituted or substituted heterocyclic or heteroaromatic ring optionally containing one or more additional heteroatom selected from O, N and S; andn is selected from 0, 1 and 2;including salts, hydrates, solvates, polymorphs, optical isomers, geometrical isomers, enantiomers, diastereomers, and mixtures thereof. 13. The method according to claim 12, wherein the quinolinyloxy is unsubstituted or substituted with one or more alkyl groups. 14. The method according to claim 12, wherein R2 is oxo. 15. The method according to claim 12, wherein the bond between C9 and C10 is a double bond, and R3, R4, R5, R6 and R7 are each hydrogen. 16. The method according to claim 12, wherein the bond between C9 and C10 is a single bond, and R3, R4, R5, R6 and R7 are each hydrogen. 17. The method according to claim 12, wherein the jasmonate ester is represented by the structure of formula C: 18. The method according to claim 12, wherein the composition is formulated for topical administration. 19. The method according to claim 18, wherein the composition is in a form selected from the group consisting of an ointment, a cream a lotion, a foam and a gel.
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