WO2007093184B1 - Treatment of mmp-mediated dermatological diseases with pemirolast - Google Patents

Treatment of mmp-mediated dermatological diseases with pemirolast

Info

Publication number
WO2007093184B1
WO2007093184B1 PCT/DK2007/050020 DK2007050020W WO2007093184B1 WO 2007093184 B1 WO2007093184 B1 WO 2007093184B1 DK 2007050020 W DK2007050020 W DK 2007050020W WO 2007093184 B1 WO2007093184 B1 WO 2007093184B1
Authority
WO
WIPO (PCT)
Prior art keywords
disease
acne
medicament
skin
group
Prior art date
Application number
PCT/DK2007/050020
Other languages
French (fr)
Other versions
WO2007093184A3 (en
WO2007093184A2 (en
Inventor
Morten Sloth Weidner
Original Assignee
Astion Pharma As
Astion Inflammation Aps
Morten Sloth Weidner
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Astion Pharma As, Astion Inflammation Aps, Morten Sloth Weidner filed Critical Astion Pharma As
Publication of WO2007093184A2 publication Critical patent/WO2007093184A2/en
Publication of WO2007093184A3 publication Critical patent/WO2007093184A3/en
Publication of WO2007093184B1 publication Critical patent/WO2007093184B1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/08—Antiseborrheics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents

Abstract

The invention relates to compounds for the treatment of dermatological diseases where inflammation, matrix metalloproteinases (MMPs) and peroxisome proliferator- activated receptors (PPARs) play a role in mediating the disease, such as the 5 treatment of acne with Pemirolast or a closely related compound thereof.

Claims

AMENDED CLAIMS received by the International Bureau on 11 September 2007(11.09.07)Claims
Use of Pemirolast or a closely related compound thereof or a pharmaceutically salt thereof for the preparation of a medicament for the treatment of a disease characterised by the presence of inflammation together with activity of matrix metalloproteinases and/or peroxisome prol iterator-activated receptors selected from the group consisting of acne, acne scarring, psoriasis, scarring of the skin, skin cancer, skin ageing, rosacea, seborrhea and seborrheic dermatitis, wherein the closely related compound thereof is defined by formula II,
Figure imgf000002_0001
II
wherein R1 and R2 each independently designate radicals selected from the group consisting of hydrido (H), optionally substituted C1-6-alkyl, C,.6~cycloalkyl, C2-6-alkenyl, C2.6-alkynyl, Q-β-alkoxyl, phenyl, C7-1,, alkaryl, C7-14 alkheterocyclyl, carboxy! (COOH), carboxyl derivative (COOR1), cyano (CN), CF3, halogen (Br, Cl, Fl, I), hydroxy (OH), hydroxy derivative (OR'), primary amino (NH2), secondary amino (NHR"), tertiary amino (NR1R"), carboxy (CO), carboxy derivative (CO- R'), and wherein R' and R" independently defines a radical selected from Ci-s-alkyl, C4.6-cycloalkyl, C2-6-alkenyl, C2-6-alkynyl, C:-6-alkoxyl, phenyl, C7-14 alkaryl and C7-I4 alkheterocyclyl; and wherein Rα and R2 may be located at any of positions 6, 7, 8 or 9 of the pyridofl^-alpyrimidine ring system.
2. The use according to claim 1, wherein the disease is acne or any clinical variant thereof or acne scarring.
3. The use according to claim 1, wherein the disease is psoriasis or any clinical variant thereof.
4. The use according to claim 1, wherein the disease is seborrhea.
5. The use according to claim 1, wherein the disease is seborrheic dermatitis.
6. The use according to claim 2, wherein the medicament further comprises a treatment agent selected from the group consisting of salicylic acid, nicotinamide, azelaic acid, a zinc compound, an antibiotic, a retinoid, an oral contraceptive and an anti-androgeπ.
7. The use according to any one of the preceding claims, wherein the medicament is formulated for topical administration to skin.
8. The use according to claim 7, wherein the medicament is formulated as a gel, solution, emulsion, foam, liniment or ointment.
9. A topically administrable pharmaceutical composition suitably formulated for being applied to skin comprising as therapeutically active ingredient Pemirolast or a closely related compound thereof or a pharmaceutically acceptable salt thereof in an amount of at least 0.1% by weight; and further comprising one or more dermatologically acceptable exdpients or carriers.
10. The composition according to claim 9, further comprising a treatment agent selected from the group consisting of salicylic acid, nicotinamide, azelaic acid, a zinc compound, an antibiotic, a retinoid, an oral contraceptive and an anti-androgen.
11. A method for treating a disease characterised by the presence of inflammation together with activity of matrix metalloproteinases and/or peroxisome proliferator- activated receptors selected from the group consisting of acne, acne scarring, psoriasis, scarring of the skin, skin cancer, skin ageing, rosacea, seborrhea and seborrheic dermatitis, comprising administering to a mammal a therapeutically effective amount of Pemirolast or a closely related compound thereof or a pharmaceutically salt thereof, wherein the closely related compound thereof is defined by formula II,
Figure imgf000003_0001
II
wherein R1 and R2 each independently designate radicals selected from the group consisting of hydrido (H), optionally substituted C1-β-afkyl, C4-6-cycloalkyl, C2.6-alkenyl, C2-6-alkynyl, C^-alkoxyl, phenyl, C7-14 alkaryl, C7-14 alkheterocyclyl, carboxyl (COOH), carboxyl derivative (COOR"), cyano (CN), CF3, halogen (Br, Cl, Fl, I), hydroxy (OH), hydroxy derivative (OR1), primary amino (NH2), secondary amino (NHR'), tertiary amino (NR1R"), carboxy (CO), carboxy derivative (CO- R"), and wherein R' and R" independently defines a radical selected from C1-6-alkyI7 C4-6-cycloalkyl, C2-s-a!kenyl, C2-6-alkynyI, C1-6-alkoxy!, phenyl, C7-M alkaryl and C7-14 alkheterocyclyl; and wherein R1 and R2 may be located at any of positions 6, 7, 8 or 9 of the pyrido[l,2-a]pyrimidine ring system.
12. The method according to claim 11, wherein the disease is acne or any clinical variant thereof or acne scarring.
13. The method according to claim 11, wherein the disease is psoriasis or any clinical variant thereof.
14. The method according to claim 11, wherein the disease is seborrhea.
15. The method according to claim 11, wherein the disease is seborrheic dermatitis.
16. The method according to claim 12, wherein the medicament further comprises a treatment agent selected from the group consisting of salicylic acid, nicotinamide, azelaic acid, a zinc compound, an antibiotic, a retinoid, an oral contraceptive and an anti-androgen.
17. The method according to any one of the preceding claims, wherein the medicament is formulated for topical administration to skin.
18. The method according to claim 17, wherein the medicament is formulated as a gel, solution, emulsion, foam, liniment or ointment.
Claims
Use of Pemirolast or a closely related compound thereof or a pharmaceutically salt thereof for the preparation of a medicament for the treatment of a disease characterised by the presence of inflammation together with activity of matrix metalloproteinases and/or peroxisome proliferator-activated receptors selected from the group consisting of acne, acne scarring, psoriasis, chronic-uleers, scarring of the skins, burns, skin cancer, skin ageing, rosacea, seborrhea and seborrheic dermatitis, wherein the closely related compound thereof is defined by formula II,
Figure imgf000005_0001
II
wherein R1 and R2 each independently designate radicals selected from the group consisting of hydrido (H), optionally substituted Ci-6-alkyl, Q,6-cycloalkyl, C2-s-alkenyl, C2-6-alkynyl, C1-s-alkoxyl, phenyl, C7-I4 alkaryl, C7.M alkheterocyclyl, carboxyl (COOH), carboxyl derivative (COOR1), cyano (CN), CF3, halogen (Br, Cl, Fl, I), hydroxy (OH), hydroxy derivative (OR"), primary amino (NH2), secondary amino (NHR"), tertiary amino (NR1R"), carboxy (CO), carboxy derivative (CO- R'), and wherein R' and R" independently defines a radical selected from Ci-6-alkyl, G,-e-cycloalkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-alkoxyl, phenyl, C7-1,, alkaryl and C7. M alkheterocyclyl; and wherein R1 and R2 may be located at any of positions 6, 7, 8 or 9 of the pyrido[l,2-a]pyrimϊdϊne ring system.
2. The use according to claim 1, wherein the disease is acne or any clinical variant thereof or acne scarring.
3. The use according to claim 1, wherein the disease is psoriasis or any clinical variant thereof.
4. The use according to claim 1, wherein the disease is seborrhea.
5. The use according to claim 1, wherein the disease is seborrheic dermatitis.
6. The use according to claim 2, wherein the medicament further comprises a treatment agent selected from the group consisting of salicylic acid, nicotinamide, azelaic acid, a zinc compound, an antibiotic, a retinoid, an oral contraceptive and an anti-androgen.
7. The use according to any one of the preceding claims, wherein the medicament is formulated for topical administration to skin or for buccal administration te-fehe mucosa .j,
8. The use according to claim 7, wherein the medicament is formulated as a gel/ solution, emulsion, foam, liniment or ointment.
9. A topically admiπϊstrable pharmaceutical composition suitably formulated for being applied to skin comprising as therapeutically active ingredient Pemirolast or a closely related compound thereof or a pharmaceutically acceptable salt thereof in an amount of at least 0.1% by weight; and further comprising one or more dermatologically acceptable excipients or carriers.
10. The composition according to claim 9, further comprising a treatment agent selected from the group consisting of salicylic acid, nicotinamide, azelaic acid, a zinc compound, an antibiotic, a retinoid, an oral contraceptive and an anti-aπdrogen.
11. A method for treating a disease characterised by the presence of inflammation together with activity of matrix metalloproteinases and/or peroxisome proliferator- activated receptors selected from the group consisting of acne, acne scarring, psoriasis, chronic ulcere, scarring of the skins, burns, skin cancer/skin ageing, rosacea, seborrhea and seborrheic dermatitis, comprising administering to a mammal a therapeutically effective amount of Pemirolast or a closely related compound thereof or a pharmaceutically salt thereof, wherein the closely related compound thereof is defined by formula II,
Figure imgf000006_0001
II
wherein R1 and Rz each independently designate radicals selected from the group consisting of hydrido (H), optionally substituted C1-s-alkyl, C4-5-cydoalkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-alkoxyl, phenyl, C7-« alkaryl, C7-M alkheterocyclyl, carboxyl (COOH), carboxyl derivative (COOR1), cyano (CN), CF3, halogen (Br, CI, Fl, I), hydroxy (OH), hydroxy derivative (OR1), primary amino (NH2), secondary amino (NHR1), tertiary amino (NR1R"), carboxy (CO), carboxy derivative (CO- R1), and wherein R' and R" independently defines a radical selected from Ci-5-alkyl, C4.6~cycloalky!, Qκ6-alkenyl, C2-5-aikynyl, C1-s-alkoxyl, phenyl, C7-14 alkaryl and C7-I4 alkheterocyclyl; and wherein R1 and R2 may be located at any of positions 6, 7, 8 or 9 of the pyrido[lr2-a]pyrimidine ring system.
12. The method according to claim 11, wherein the disease is acne or any clinical variant thereof or acne scarring.
13. The method according to claim 11, wherein the disease is psoriasis or any clinical variant thereof.
14. The method according to claim 11, wherein the disease is seborrhea.
15. The method according to claim 11, wherein the disease is seborrheic dermatitis.
16. The method according to claim 12, wherein the medicament further comprises a treatment agent selected from the group consisting of salicylic acid, nicotinamide, azelaic acid, a zinc compound, an antibiotic, a retinoid, an oral contraceptive and an aπti-androgen.
17. The method according to any one of the preceding claims, wherein the medicament is formulated for topical administration to skin- or for buccal administration to the
18. The method according to claim 17, wherein the medicament is formulated as a gel, solution, emulsion, foam, liniment or ointment.
PCT/DK2007/050020 2006-02-13 2007-02-13 Treatment of mmp-mediated dermatological diseases with pemirolast WO2007093184A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US77252706P 2006-02-13 2006-02-13
US60/772,527 2006-02-13
EP06002867.7 2006-02-13
EP06002867 2006-02-13

Publications (3)

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WO2007093184A2 WO2007093184A2 (en) 2007-08-23
WO2007093184A3 WO2007093184A3 (en) 2007-10-25
WO2007093184B1 true WO2007093184B1 (en) 2007-11-29

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Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4457932A (en) * 1983-07-22 1984-07-03 Bristol-Myers Company Anti-ulcer agents
HUT64064A (en) * 1992-02-13 1993-11-29 Chinoin Gyogyszer Es Vegyeszet Process for producing puyrido/1,2-a/pyrimidine derivatives and pharmaceutical compositions comprising same as active ingredient
US5527802A (en) * 1992-10-01 1996-06-18 Bristol-Myers Squibb Company New uses of 3-tetrazolo -5,6,7,8- substituted-pyrido (1,2-a) pyrimidin-4-ones
JP2004345984A (en) * 2003-05-21 2004-12-09 Mitsubishi Pharma Corp Agent for preventing and reducing sensitive reaction caused by administration of anti-cancer agent

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WO2007093184A2 (en) 2007-08-23

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