Patent EP0770577A1 successfully refreshed from Google Patents.
EP0770577A1
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EP
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Fullerene derivatives as free-radical scavengers
Assignee: National Science and Technology Council
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Filing: 1996-04-12
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Granted: —
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Expires: 2016-04-12
Abstract
Abstract The invenion relates to fullerene derivatives which are capable of scavenging free radicals. The derivatives have the formula F(-X) m (-Y-Z) n , in which F is a fullerene core; each X is independently -CO 2 - , -SO 3 - , - SH, or the like; each -Y-Z is independently (C 3-30 alkyl ether) 50 -CH 2 -CO 2 - , (C 3-30 alkyl ester) 50 -CH 2 -SO 3 - , (C 3-30 alkyl amide) 50 -CH 2 -SH, or the like; m is 0-30; n is 0-30; and the sum of m and n is 2-30.
Inventors
- 👤 Long Y. Chiang
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-24 20:24
CPC Classifications
B; B82; B82Y; B82Y30/00; A; A61; A61K; A61K31/00; A61K31/045; A61K31/185; B82Y40/00; C; C01; C01B; C01B32/00; C01B32/15; C01B32/152; C01B32/156; C07; C07C; C07C233/00; C07C233/01; C07C233/02; C07C233/04; C07C233/06; C07C275/00; C07C275/26; C07C309/00; C07C309/01; C07C309/02; C07C309/03; C07C309/07; C07C309/09; C07C309/19; C07C35/00; C07C35/22; C07C35/44; C07C2604/00; Y; Y10; Y10S; Y10S977/00; Y10S977/70; Y10S977/734; Y10S977/735; Y10S977/737; Y10S977/738; Y10S977/84; Y10S977/895; Y10S977/896; Y10S977/902
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
833 words
A compound of formula I F(-X) m (-Y-Z) n (I) wherein F is a fullerene core; each X is independently -CO 2 - , -SO 3 - , -OH, -SH, -PO 3 - , -O-PO 3 2- , -O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-CH 2 -CH 2 -NH 3 + , -NH 2 , NH 3 + , -N+H 2 R a , N + HR a R b or -N + R a R b R c ; each Y is -A-B-, in which A is independently -CH 2 -, -O-, -S-, -NH-CO-NH-, or -NH-CO-; and B is independently -R d -O-[Si(CH 3 ) 2 -O-] 1-100 , C 1-2000 alkyl, C 6-40 aryl, C 7-60 alkylaryl, C 7-60 arylalkyl, (C 1-30 alkyl ether) 1-100 , (C 6-40 aryl ether) 1-100 , (C 7-60 alkylaryl ether) 1-100 , (C 7-60 arylalkyl ether) 1-100 , (C 1-30 alkyl thioether) 1-100 , (C 6-40 aryl thioether) 1-100 , (C 7-60 alkylaryl thioether) 1-100 , (C 7-60 arylalkyl thioether) 1-100 , (C 2-50 alkyl ester) 1-100 , (C 7-60 aryl ester) 1-100 , (C 8-70 alkylaryl ester) 1-100 , (C 8-70 arylalkyl ester) 1-100 , -R-CO-O-(C 1-30 alkyl ether) 1-100 , -R-CO-O-(C 6-40 aryl ether) 1-100 , -R-CO-O-(C 7-60 alkylaryl ether) 1-100 , -R-CO-O-(C 7-60 arylalkyl ether) 1-100 , (C 4-50 alkyl urethane) 1-100 , (C 14-60 aryl urethane) 1-100 , (C 10-80 alkylaryl urethane) 1-100 , (C 10-80 arylalkyl urethane) 1-100 , (C 5-50 alkyl urea) 1-100 , (C 14-60 aryl urea) 1-100 , (C 10-80 alkylaryl urea) 1-100 , (C 10-80 arylalkyl urea) 1-100 , (C 2-50 alkyl amide) 1-100 , (C 7-60 aryl amide) 1-100 , (C 8-70 alkylaryl amide) 1-100 , (C 8-70 arylalkyl amide) 1-100 , (C 3-30 alkyl anhydride) 1-100 , (C 8-50 aryl anhydride) 1-100 , (C 9-60 alkylaryl anhydride) 1-100 , (C 9-60 arylalkyl anhydride) 1-100 , (C 2-30 alkyl carbonate) 1-100 , (C 7-50 aryl carbonate) 1-100 , (C 8-60 alkylaryl carbonate) 1-100 , (C 8-60 arylalkyl carbonate) 1-100 , -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 1-30 alkyl ether, c 6-40 aryl ether, C 7-60 alkylaryl ether, or C 7-60 arylalkyl ether) 1-100 , -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 2-50 alkyl ester, C 7-60 aryl ester, C 8-70 alkylaryl ester, or C 8-70 arylalkyl ester) 1-100 , -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 1-30 alkyl ether, C 6-40 aryl ether, C 7-60 alkylaryl ether, or C 7-60 arylalkyl ether) 1-100 -CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-, -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 2-50 alkyl ester, C 7-60 aryl ester, C 8-70 alkylaryl ester, or C 8-70 arylalkyl ester) 1-100 -R 3 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-, -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 1-30 alkyl ether, C 6-40 aryl ether, C 7-60 alkylaryl ether, or C 7-60 arylalkyl ether) 1-100 , -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 2-50 alkyl ester, C 7-60 aryl ester, C 8-70 alkylaryl ester, or C 8-70 arylalkyl ester) 1-100 , -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 1-30 alkyl ether, C 6-40 aryl ether, C 7-60 alkylaryl ether, or C 7-60 arylalkyl ether) 1-100 -CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-, -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 2-50 alkyl ester, C 7-60 aryl ester, C 8-70 alkylaryl ester, or C 8-70 arylalkyl ester) 1-100 -R 3 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-, -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-NH- (C 2-50 alkyl amide, C 7-60 aryl amide, C 7-70 alkylaryl amide, or C 7-70 arylalkyl amide) 1-100 , or -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-NH-(C 2-50 alkyl amide, C 7-60 aryl amide, C 7-70 alkylaryl amide, or C 7-70 arylalkyl amide) 1-100 ; each Z is -C-D, wherein C is independently -R-, -R-Ar-, -Ar-, or -Ar-R-; and D is independently -OH, -SH, -SO 3 - , -OSO 3 - , -CO 2 - , -PO 3 - , -O-PO 3 2- , -O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-CH 2 -CH 2 -NH 3 + , -NH 2 , NH 3 + , -N+H 2 R a' , N + HR a' R b' or -N + R a' R b' R c' ; and m is 0-30, n is 0-30 and the sum of m and n is 2-30 with the proviso that where X is -OH, -NH 2 , NH 3 + , -N + H 2 R a' N + HR a R b or -N + R a R b R c then n is at least 1; in which each of R, R 1 , R 2 , R 3 , R a , R b , R c , R d , R a' , R b' and R c' is independently C 1-20 alkyl, and Ar is independently C 6-40 aryl, or a salt thereof.
Claim 2
Dependent Claim
59 words
A compound of formula I as claimed in claim 1 wherein each X is independently -CO 2 - , -SO 3 - , -SH, -PO 3 - , -O-PO 3 2- , -O-PO-(O - )-O-PO 3 2- , -O-PO(O - )-O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-CH 2 -CH 2 -NH 3 + or a salt thereof.
Claim 3
Dependent Claim
314 words
A compound of formula I as claimed in either one of claims 1 and 2 wherein each B is independently -R d -O-[Si(CH 3 ) 2 -O-] 1-100 , C 1-2000 alkyl, C 6-40 aryl, C 7-60 alkylaryl, C 7-60 arylalkyl, (C 1-30 alkyl ether) 1-100 , (C 7-60 alkylaryl ether) 1-100 , (C 1-30 alkyl thioether) 1-100 , (C 7-60 alkylaryl thioether) 1-100 , (C 2-50 alkyl ester) 1-100 , (C 8-70 alkylaryl ester) 1-100 , -R-CO-O-(C 1-30 alkyl ether) 1-100 , (C 4-50 alkyl urethane) 1-100 , (C 10-80 alkylaryl urethane) 1-100 , (C 5-50 alkyl urea) 1-100 , (C 10-80 alkylaryl urea) 1-100 , (C 2-50 alkyl amide) 1-100 , (C 8-70 alkylaryl amide) 1-100 , (C 3-30 alkyl anhydride) 1-100 , (C 9-60 alkylaryl anhydride) 1-100 , (C 2-30 alkyl carbonate) 1-100 , (C 8-60 alkylaryl carbonate) 1-100 , -R 1 -O-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 1-30 alkyl ether or C 7-60 alkylaryl ether) 1-100 , -R 1 -O-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 2-50 alkyl ester or C 8-70 alkylaryl ester) 1-100 , -R 1 -O-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 1-30 alkyl ether or C 7-60 alkylaryl ether) 1-100 -CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-, -R 1 -NH-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 1-30 alkyl ether or C 7-60 alkylaryl ether) 1-100 , -R 1 -NH-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 2-50 alkyl ester or C 8-70 alkylaryl ester) 1-100 , -R 1 -NH-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 1-30 alkyl ether or C 7-60 alkylaryl ether) 1-100 , -CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-, -R 1 -O-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-NH-(C 2-50 alkyl amide or C 7-70 alkylaryl amide) 1-100 , or -R 1 -NH-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-NH-(C 2-50 alkyl amide or C 7-70 alkylaryl amide) 1-100; and each C is independently -R-, -R-Ph in which Ph is p-phenylene or a salt thereof.
Claim 4
Dependent Claim
68 words
A compound of formula I as claimed in any one of claims 1 to 3 wherein each D is independently -SO 3 - , -OSO 3 - , -CO 2 - , -PO 3 - , -O-PO 3 2- , -O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-CH 2 -CH 2 -NH 3 + , or a salt thereof.
Claim 5
Dependent Claim
23 words
A compound of formula I as claimed in any one of claims 1 to 4 wherein m is 0, or a salt thereof.
Claim 6
Dependent Claim
29 words
A compound of formula I as claimed in any one of claims 1 to 5 wherein m is 0 and n is 4 to 16, or a salt thereof.
Claim 7
Dependent Claim
42 words
A compound of formula I as claimed in any one of claims 1 to 4 wherein m and n each have a value of up to 16 and the sum of m and n is 4 to 16, or a salt thereof.
Claim 8
Dependent Claim
804 words
A composition comprising a biologically compatible substance and a compound of formula I F(-X) m (-Y-Z) n (I) wherein F is a fullerene core; each X is independently -CO 2 - , -SO 3 - , -OH, -SH, -PO 3 - , -O-PO 3 2- , -O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-CH 2 -CH 2 -NH 3 + , -NH 2 , -NH 3 + , -N + H 2 R a , -N + HR a R b or -N + R a R b R c ; each Y is -A-B-, in which A is independently -CH 2 -, -O-, -S-, -NH-CO-NH-, or -NH-CO-; and B is independently -R d -O-[Si(CH 3 ) 2 -O-] 1-100 , C 1-2000 alkyl, C 6-40 aryl, C 7-60 alkylaryl, C 7-60 arylalkyl, (C 1-30 alkyl ether) 1-100 , (C 6-40 aryl ether) 1-100 , (C 7-60 alkylaryl ether) 1-100 , (C 7-60 arylalkyl ether) 1-100 , (C 1-30 alkyl thioether) 1-100 , (C 6-40 aryl thioether) 1-100 , (C 7-60 alkylaryl thioether) 1-100 , (C 7-60 arylalkyl thioether) 1-100 , (C 2-50 alkyl ester) 1-100 , (C 7-60 aryl ester) 1-100 , (C 8-70 alkylaryl ester) 1-100 , (C 8-70 arylalkyl ester) 1-100 , -R-CO-O-(C 1-30 alkyl ether) 1-100 , -R-CO-O-(C 6-40 aryl ether) 1-100 , -R-CO-O-(C 7-60 alkylaryl ether) 1-100 , -R-CO-O-(C 7-60 arylalkyl ether) 1-100 , (C 4-50 alkyl urethane) 1-100 , (C 14-60 aryl urethane) 1-100 , (C 10-80 alkylaryl urethane) 1-100 , (C 10-80 arylalkyl urethane) 1-100 , (C 5-50 alkyl urea) 1-100 , (C 14-60 aryl urea) 1-100 , (C 10-80 alkylaryl urea) 1-100 , (C 10-80 arylalkyl urea) 1-100 , (C 2-50 alkyl amide) 1-100 , (C 7-60 aryl amide) 1-100 , (C 8-70 alkylaryl amide) 1-100 , (C 8-70 arylalkyl amide) 1-100 , (C 3-30 alkyl anhydride) 1-100 , (C 8-50 aryl anhydride) 1-100 , (C 9-60 alkylaryl anhydride) 1-100 , (C 9-60 arylalkyl anhydride) 1-100 , (C 2-30 alkyl carbonate) 1-100 , (C 7-50 aryl carbonate) 1-100 , (C 8-60 alkylaryl carbonate) 1-100 , (C 8-60 arylalkyl carbonate) 1-100 , -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 1-30 alkyl ether, c 6-40 aryl ether, C 7-60 alkylaryl ether, or C 7-60 arylalkyl ether) 1-100 , -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 2-50 alkyl ester, C 7-60 aryl ester, C 8-70 alkylaryl ester, or C 8-70 arylalkyl ester) 1-100 , -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 1-30 alkyl ether, C 6-40 aryl ether, C 7-60 alkylaryl ether, or C 7-60 arylalkyl ether) 1-100 -CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-, -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 2-50 alkyl ester, C 7-60 aryl ester, C 8-70 alkylaryl ester, or C 8-70 arylalkyl ester) 1-100 -R 3 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-, -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 1-30 alkyl ether, C 6-40 aryl ether, C 7-60 alkylaryl ether, or C 7-60 arylalkyl ether) 1-100 , -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 2-50 alkyl ester, C 7-60 aryl ester, C 8-70 alkylaryl ester, or C 8-70 arylalkyl ester) 1-100 , -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 1-30 alkyl ether, C 6-40 aryl ether, C 7-60 alkylaryl ether, or C 7-60 arylalkyl ether) 1-100 -CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-, -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-(C 2-50 alkyl ester, C 7-60 aryl ester, C 8-70 alkylaryl ester, or C 8-70 arylalkyl ester) 1-100 -R 3 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-O-, -R 1 -O-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-NH- (C 2-50 alkyl amide, C 7-60 aryl amide, C 8-70 alkylaryl amide, or C 8-70 arylalkyl amide) 1-100 , or -R 1 -NH-CO-NH-(R 2 or Ar-R 2 -Ar)-NH-CO-NH-(C 2-50 alkyl amide, C 7-60 aryl amide, C 7-70 alkylaryl amide, or C 7-70 arylalkyl amide) 1-100 ; each Z is -C-D, wherein C is independently -R-, - R-Ar-, -Ar-, or -Ar-R-; and D is independently -OH, -SH, -SO 3 - , -OSO 3 - , -CO 2 - , -PO 3 - , -O-PO 3 2- , -O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-CH 2 -CH 2 -NH 3 + , -NH 2 , -NH 3 + , -N + H 2 R a' , -N + HR a' R b' or -N + R a' R b' R c' ; and m is 0-30, n is 0-30 and the sum of m and n is 2-30; in which each of R, R 1 , R 2 , R 3 , R a , R b , R c , R d , R a' , R b' and R c' is independently C 1-20 alkyl, and Ar is independently C 6-40 aryl, or a salt thereof.
Claim 9
Dependent Claim
313 words
A composition as claimed in claim 8 wherein in the compound of formula I each B is independently -R d -O-[Si(CH 3 ) 2 -O-] 1-100 , C 1-2000 alkyl, C 6-40 aryl, C 7-60 alkylaryl, C 7-60 arylalkyl, (C 1-30 alkyl ether) 1-100 , (C 7-60 alkylaryl ether) 1-100 , (C 1-30 alkyl thioether) 1-100 , (C 7-60 alkylaryl thioether) 1-100 , (C 2-50 alkyl ester) 1-100 , (C 8-70 alkylaryl ester) 1-100 , -R-CO-O-(C 1-30 alkyl ether) 1-100 , (C 4-50 alkyl urethane) 1-100 , (C 10-80 alkylaryl urethane) 1-100 , (C 5-50 alkyl urea) 1-100 , (C 10-80 alkylaryl urea) 1-100 , (C 2-50 alkyl amide) 1-100 , (C 8-70 alkylaryl amide) 1-100 , (C 3-30 alkyl anhydride) 1-100 , (C 9-60 alkylaryl anhydride) 1-100 , (C 2-30 alkyl carbonate) 1-100 , (C 8-60 alkylaryl carbonate) 1-100 , -R 1 -O-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 1-30 alkyl ether or C 7-60 alkylaryl ether) 1-100 , -R 1 -O-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 2-50 alkyl ester or C 8-70 alkylaryl ester) 1-100 , -R 1 -O-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 1-30 alkyl ether or C 7-60 alkylaryl ether) 1-100 -CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-, -R 1 -NH-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 1-30 alkyl ether or C 7-60 alkylaryl ether) 1-100 , -R 1 -NH-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 2-50 alkyl ester or C 8-70 alkylaryl ester) 1-100 , -R 1 -NH-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-(C 1-30 alkyl ether or C 7-60 alkylaryl ether) 1-100 , -CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-O-, -R 1 -O-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-NH-(C 2-50 alkyl amide or C 7-70 alkylaryl amide) 1-100 , or -R 1 -NH-CO-NH-(R 2 or Ph-R 2 -Ph)-NH-CO-NH-(C 2-50 alkyl amide or C 7-70 alkylaryl amide) 1-100 ; and each C is independently -R-, -R-Ph in which Ph is p-phenylene or a salt thereof.
Claim 10
Dependent Claim
67 words
A composition as claimed in either one of claims 8 and 9 wherein in the compound of formula I each X is independently -CO 2 - , -SO 3 - , -SH, -PO 3 - , -O-PO 3 2- , -O-PO-(O - )-O-PO 3 2- , -O-PO(O - )-O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-CH 2 -CH 2 -NH 3 + ,or a salt thereof.
Claim 11
Dependent Claim
71 words
A composition as claimed in any one of claims 8 to 10 wherein in the compound of formula I each D is independently -SO 3 - , -OSO 3 - , -CO 2 - , -PO 3 - , -O-PO 3 2- , -O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-PO(O - )-O-PO 3 2- , -O-PO(O - )-O-CH 2 -CH 2 -NH 3 + , or a salt thereof.
Claim 12
Dependent Claim
34 words
A composition as claimed in any one of claims 8 to 11 wherein in the compound of formula I, m is 0-16, n is 1-16, and the sum of m and n is 4-16.
Claim 13
Dependent Claim
22 words
A composition as claimed in claim 8 containing a compound or salt as claimed in any one of claims 1 to 7.
Claim 14
Dependent Claim
17 words
A compound of formula I as defined in claim 8 or a salt thereof, for medical use.
Claim 15
Dependent Claim
34 words
The use of a compound of formula I as defined in claim 8 or a salt thereof, for the manufacture of a medicament for the treatment of disorders or diseases associated with free radicals.
References Cited (Backward Citations)
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