Patent EP0445975A1 successfully refreshed from Google Patents.
EP0445975A1
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EP
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New hydroxymacrolide derivatives having immunosuppressive activity
Assignee: Merck and Co Inc
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Filing: 1991-02-28
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Granted: —
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Expires: 2011-02-28
Abstract
Abstract Novel hydroxymacrolide derivatives of the general structual Formula I: <CHEM> have been prepared from (a) suitable precursor(s) by selective reduction of the ketone at C-2. These macrolide immunosuppressants are useful in a human host for the treatment of autoimmune diseases (such as juvenile-onset diabetes melitus, multiple sclerosis and rheumatoid arthritis), infectous diseases and/or the prevention of rejection of foreign organ transplants, e.g. bone marrow and heart transplants. In addition, these macrolide immunosuppressants are useful in the topical treatment of inflammatory and hyperproliferative skin diseases and cutaneous manifestations of immunologically-mediated illnesses such as: psoriasis, atopical dermatitiis, contact dermatitis and further eczematous dermatitises, seborrhoeic dermatitis, Lichen planus, Pemphigus, bullous Pemphigoid, Epidermolysis bullosa, urticaria, angioedemas, vasculitides, erythemas, cutaneous eosinophilias, Lupus erythematosus or Alopecia areata.
Inventors
- 👤 Richard J. Bochis
- 👤 Hyun O. Ok
- 👤 Matthew J. Wyvratt
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-08 04:10
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/01; A; A61; A61P; A61P17/00; A61P37/00; A61P37/02; A61P37/06
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
49 words
A compound of formula I: wherein: R is methyl, ethyl, propyl or allyl; R¹ and R² are, independently, hydrogen, formyl, acetyl, propionyl or a hydroxyl protecting group; R³ is C₁-C₆ alkanoyl, R⁴ is hydrogen, formyl, acetyl or propionyl; n is 1 or 2; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
40 words
The compound of Claim 1 wherein: R is methyl, ethyl, propyl or allyl; R¹ is hydrogen; R² is hydrogen; R³ is C₁-C₆ alkanoyl; R⁴ is hydrogen, formyl or acetyl; n is 1 or 2; or the pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
41 words
The compound of Claim 2 wherein: R is methyl, ethyl, propyl or allyl; R¹ is hydrogen; R² is hydrogen; R³ is formyl or acetyl; R⁴ is hydrogen, formyl or acetyl; n is 1 or 2; or the pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
198 words
The compound according to Claim 1, selected from the group consisting of compounds of the formula I wherein: (a) R is allyl, R¹ is hydrogen, R² is hydrogen, R³ is acetyl, R⁴ is hydrogen and n is 2; (b) R is ethyl, R¹ is hydrogen, R² is hydrogen, R³ is acetyl, R⁴ is hydrogen and n is 2; (c) R is propyl, R¹ is hydrogen, R² is hydrogen, R³ is acetyl, R⁴ is hydrogen and n is 2; (d) R is allyl, R¹ is hydrogen, R² is hydrogen, R³ is acetyl, R⁴ is hydrogen and n is 1; (e) R is ethyl, R¹ is hydrogen, R² is hydrogen, R³ is acetyl, R⁴ is acetyl and n is 2; (f) R is ethyl, R¹ is acetyl, R² is hydrogen, R³ is acetyl, R⁴ is hydrogen and n is 2; (g) R is ethyl, R¹ is hydrogen, R² is acetyl, R³ is acetyl, R⁴ is hydrogen and n is 2; (h) R is ethyl, R¹ is acetyl, R² is acetyl, R³ is acetyl, R⁴ is hydrogen and n is 2; (i) R is ethyl, R¹ is acetyl, R² is acetyl, R³ is acetyl, R⁴ is acetyl and n is 2.
Claim 5
Dependent Claim
29 words
A pharmaceutical composition for the treatment of immunoregulatory disorders or diseases comprising a pharmaceutical carrier and a therapeutically effective amount of compound of formula I, according to Claim 1.
Claim 6
Dependent Claim
38 words
A pharmaceutical composition for the topical treatment of inflammatory and hyperproliferative skin diseases and or cutaneous manifestations of immunologically-mediated illnesses comprising a pharmaceutical carrier and a therapeutically effective amount of compound of formula I, according to Claim 1.
Claim 7
Dependent Claim
26 words
The use of a compound of formula I according to Claim 1 for the manufacture of a medicament for the treatment of immunoregulatory disorders or diseases.
Claim 8
Dependent Claim
34 words
The use of a compound of formula I according to Claim 1 for the manufacture of a medicament for the topical treatment of inflammatory and hyperproliferative skin diseases and/or cutaneous manifestations of immunologically-mediated illnesses.
Claim 9
Dependent Claim
134 words
A process for the production of a compound of formula I: wherein: R is methyl, ethyl, propyl or allyl; R¹ and R² are, independently, hydrogen, formyl, acetyl, propionyl or a hydroxyl protecting group; R³ is C₁-C₆ alkanoyl, R⁴ is hydrogen, formyl, acetyl or propionyl; n is 1 or 2; or a pharmaceutically acceptable salt thereof, which comprises: contacting a compound of formula IIa: wherein: R is methyl, ethyl, propyl or allyl; R¹ and R² are, independently, hydrogen or a hydroxyl protecting group; R³ a is hydrogen; R⁴ is hydrogen; n is 1 or 2; with an appropriate acid chloride or acid anhydride in an inert organic solvent in the presence of a suitable base at a temperature between 0°C and solvent reflux temperature for a sufficient time to form a compound of formula I.
Claim 10
Dependent Claim
26 words
The use of a compound of Claim 1 for the manufacture of a medicament for treating or preventing resistance by transplantation, autoimmune diseases and infectious diseases.
References Cited (Backward Citations)
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