Patent EA-002644-B1 (EA)
Title: 4-cyano-4-deformylsordaricin derivatives
Inventor: TSE BRUNO
IPC: C07D309/12
Filed: 1998-08-18
Abstract: 1. A compound having the formula I:   wherein R is (a) C(=O)OR<1>, (b) C(=O)NR<2>R<3>, (c) C(=O)R<4>, (d) CH(R<2>)OR<5>, (e) C(R<6>)(R<7>)(R<8>), or (f)    (g) H; R<1> is (a) C1-C14 alkyl, (b) C2-C14 alkenyl, (c) C2-C14 alkynyl, (d) C3-C20 cycloalkyl, (e) aryl or (f) aryl C1-6 alkyl; R<2> and R<3> are independently (a) H or (b) R<1>; R<4> is (a) H, (b) R<1> or (c) -(CH2)m NR<2>R<3>; R<5> is (a) R<1> or (b) -(CH2)x O(CH2)y H; <DP=2 R<6> is (a) H, (b) C1-C14 alkyl, (c) aryl, (d) aryl C1-6 alkyl, (e) -(CH2)y CHR<9>(CH2)z H, (f) -(CH2)y C [triple bond] (CH2)z H, (g) -(CH2)y C(R<7>)=CH(CH2)z H, (h) -(CH2)y C [triple bond] C(CH2)m R<9>, (i) -(CH2)y C(R<7>)=CH(CH2)m R<9>, R<7> and R<8> are independently (a) H, or (b) C1-C14 alkyl; R<9> is (a) OH or (b) NR<2>R<3>; R<10> is (a) H, (b) -CH2C6H5, (c) -CH2CH=CH2, (d)      or n is 0 or 1; m is 1-6; x is 2-6; y is 0-6; z is 0-6; or a pharmaceutically or agriculturally acceptable salt thereof. 2. A compound of Claim 1 having the formula Ia:   wherein R is (a) C(=O)OR<1>, (b) C(=O)NR<2>R<3>, (c) C(=O)R<4>, (d) CH2OR<5>, (e) C(R<6>)(R<7>)(R<8>), or (f)    or a pharmaceutically acceptable salt thereof. 3. A compound of Claim 2 wherein R is C(=O)OR<1>. 4. A compound of Claim 2 wherein R is C(=O)NR<2>R<3> or a pharmaceutically acceptable salt thereof. 5. A compound of Claim 2 wherein R is C(=O)R<4>; or a pharmaceutically acceptable salt thereof. 6. A compound of Claim 2 wherein R is CH(R<2>)OR<5>; or a pharmaceutically acceptable salt thereof. 7. A compound of Claim 2 wherein R is C(R<6>)(R<7>)(R<8>); or a pharmaceutically acceptable salt thereof. 8. A compound of Claim 2 wherein R is      or a pharmaceutically acceptable salt thereof. 9. A compound of Claim 2 wherein R is CH(R<6>)(R<7>), R<6> is (a) H, (b) C1-C14 alkyl, (c) aryl, (d) aryl C1-6 alkyl, (e) -(CH2)y CHR<9>(CH2)z H, (f) -(CH2)y C(R<7>)=CH(CH2)z H, R<7> is H or C1-C6 alkyl, R<9> is OH; or a pharmaceutically acceptable salt thereof. 10. A compound of Claim 2 wherein R is (a) -CH3, (b) -CH2CH3, (c) -CH2CH2CH3, (d) -CH2CH2CH2CH3, (e) -CH2CH2CH2CH2CH3, (f) -CH2CH2CH2CH2CH2CH3, (g) -CH2CH2CH2CH2CH2CH2CH3, (h) -CH2CH2CH2CH2CH2CH2CH2CH3, (i) -CH2CH2CH2CH2CH2CH2CH2CH2CH3, (j) -CH2CH2CH(CH3)2, (k) -CH2C6H5, (l) -CH(CH3)2, (m) -CH2CH(CH3)2, (n) -CH2CH=CH2, (o) -CH2CH=CHCH3, (p) -CH2CH=CHCH2CH3, (q) -CH2CH=CH CH2CH2CH3; or a pharmaceutically acceptable salt thereof. 11. A compound of Claim 2 wherein R is (a) -CH3 (b) -CH2CH3, (c) -CH2CH2CH3, (d) -CH2CH2CH2CH3, (e) -CH2CH2CH2CH2CH3 (f) -CH2CH(CH3)2, (g) -CH2CH2CH(CH3)2, (h) -CH2CH=CHCH3, (i) -CH2CH=CHCH2CH3, (j) -CH2CH=CH CH2CH2CH3; or a pharmaceutically acceptable salt thereof. 12. A compound of Claim 1 wherein R is H, or a pharmaceutically acceptable salt thereof. 13. A pharmaceutical composition which comprises a compound of Claim 1 and a pharmaceutically acceptable carrier. 14. An agrochemical composition which comprises a compound of Claim 1 and a agriculturally acceptable carrier. 15. A method for the treatment or prevention of fungal infection in an animal which comprises adminstering to said animal an antifungal effective amount of a compound of Claim 1. 16. A method for controlling phytopathogenic fungi which comprises administering to a plant in need of such control an antifungal effective amount of a compound of Claim 1.