Rapamycin acetals as immunosuppressant and antifungal agents
First Claim
Patent Images
1. A compound according to the formula:
- ##STR4## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
Y is O or S;
X is --CH3, --(CH2)n CH3, , --CH2 C6 H6, --(CH2)2 OCH3, --CH2 Cl3 or --CH2 CH2 Si(CH3)3 and L is selected from tetrahydrofuran-2-yl, tetrahydrothiophen-2-yl, tetrahydrothiopyran-2-yl, tetrahydropyran-2-yl, 4-methoxytetrahydropyran-2-yl, 4-methoxytetrahydrothiopyran-2-yl, or 4-methoxytetrahydrothiopyran-S, S-dioxide-2-yl with a provision that R1 and R2 cannot simultaneously be hydrogen and n is 1-5.
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Abstract
Derivatives of Rapamycin where the hydroxy group at position 31 and/or 42 are reacted with acetal forming reagents have been shown to have immunosuppressant and antifungal properties. These derivatives are represented by the formula: ##STR1## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
Y is O or S; X is --CH3, --(CH2)n CH3, --CH2 C6 H6, --(CH2)2 OCH3, --CH2 Cl3 or --CH2 CH2 Si(CH3)3 and L is selected from tetrahydrofuran-2-yl, tetrahydrothiophen-2-yl, tetrahydrothiopyran-2-yl, tetrahydropyran-2-yl, 4-methoxytetrahydropyran-2-yl, 4-methoxytetrahydrothiopyran-2-yl, or 4-methoxytetrahydrothiopyran-S, S-dioxide-2-yl with a proviso that R1 and R2 cannot simultaneously be hydrogen and n is 1-5.
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Citations
13 Claims
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1. A compound according to the formula:
- ##STR4## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
Y is O or S;
X is --CH3, --(CH2)n CH3, , --CH2 C6 H6, --(CH2)2 OCH3, --CH2 Cl3 or --CH2 CH2 Si(CH3)3 and L is selected from tetrahydrofuran-2-yl, tetrahydrothiophen-2-yl, tetrahydrothiopyran-2-yl, tetrahydropyran-2-yl, 4-methoxytetrahydropyran-2-yl, 4-methoxytetrahydrothiopyran-2-yl, or 4-methoxytetrahydrothiopyran-S, S-dioxide-2-yl with a provision that R1 and R2 cannot simultaneously be hydrogen and n is 1-5. - View Dependent Claims (2, 3, 4)
- ##STR4## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
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5. A method of treating transplant rejection and host vs graft disease, autoimmunine disease and disease of inflammation in a mammal by administering thereto an effective amount of a compound having the formula:
- ##STR5## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
Y is O or S;
X is --CH3, --(CH2)n CH3, --CH2 C6 H6, --(CH2)2 OCH3, --CH2 Cl3 or --CH2 CH3 Si(CH3)3 and L is selected from tetrahydrofuran-2-yl, tetrahydrothiophen-2-yl, tetrahydrothiopyran-2-yl, tetrahydropyran-2-yl, 4-methoxytetrahydropyran-2-yl, 4-methoxytetrahydrothiopyran-2-yl, or 4-methoxytetrahydrothiopyran-S, S-dioxide-2-yl with a proviso that R1 and R2 cannot simultaneously be hydrogen and n is 1-5. - View Dependent Claims (6, 7, 8)
- ##STR5## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
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9. A method of treating fugal infections in mammals by administering thereto an effective amount of a compound having the formula:
- ##STR6## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
Y is O or S;
X is --CH3, --(CH2)n CH3, --CH2 C6 H6, --(CH2)2 OCH3, --CH2 Cl3 or --CH2 CH2 Si(CH3)3 and L is selected from tetrahydrofuran-2-yl, tetrahydrothiophen-2-yl, tetrahydrothiopyran-2-yl, tetrahydropyran-2-yl, 4-methoxytetrahydropyran-2-yl, 4-methoxytetrahydrothiopyran-2-yl, or 4-methoxytetrahydrothiopyran-S, S-dioxide-2-yl with a provision that R1 and R2 cannot simultaneously be hydrogen and n is 1-5. - View Dependent Claims (10, 11, 12)
- ##STR6## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
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13. A pharmaceutical composition comprising
(a) an effective amount of a compound according to the formula: - ##STR7## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
Y is O or S;
X is --CH3, --(CH2)n CH3, --CH2 C6 H6, --(CH2)2 OCH3, --CH2 Cl3 or --CH2 CH2 Si(CH3)3 and L is selected from tetrahydrofuran-2-yl, tetrahydrothiophen-2yl, tetrahydrothiopyran-2-yl, tetrahydropyran-2-yl, 4-methoxytetrahydropyran-2-yl, 4-methoxytetrahydrothiopyran-2-yl, or 4-methoxytetrahydrothiopyran-S, S-dioxide-2-yl with a proviso that R1 and R2 cannot simultaneously be hydrogen and n is 1-5, and(b) a pharmaceutical carrier.
- ##STR7## wherein R1 and R2 independently are hydrogen, --CH2 YX, --C(CH3)2 YX, --CH2 (CH3)YX, or L;
Specification
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Current AssigneeWyeth (Pfizer Inc.)
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Original AssigneeAmerican Home Products Corporation (Pfizer Inc.)
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InventorsCaufield, Craig E., Schiehser, Guy A.
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Primary Examiner(s)BOND, ROBERT
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Application NumberUS07/788,682Time in Patent Office328 DaysField of Search540/456, 540/452, 514/291, 514/63US Class Current514/63CPC Class CodesC07D 498/18 Bridged systems
