US4720587A
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US
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Fluoranthene derivatives
Assignee: SmithKline Beecham Corp
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Filing: 1984-10-17
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Granted: 1988-01-19
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Expires: 2004-10-17
Abstract
Abstract The present invention relates to compounds of formula (I) ArCH.sub.2 R.sup.1 (I) or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a fluoranthene or substituted fluoranthene ring system; R 1 contains not more than eight carbon carbon atoms and is a group ##STR1## wherein m is 0 or 1; R 5 is hydrogen; R 6 and R 7 are the same or different and each is hydrogen or C 1-3 alkyl optionally substituted by hydroxy; R 8 and R 9 are the same or different and each is hydrogen or C 1-3 alkyl; ##STR2## is a five- or six-membered saturated carbocyclic ring; R 10 is hydrogen, methyl or hydroxymethyl; R 11 , R 12 and R 13 are the same or different and each is hydrogen or methyl; R 14 is hydrogen, methyl, hydroxy, or hydroxymethyl.
Inventors
- 👤 Kenneth W. Bair
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 03:12
CPC Classifications
C; C07; C07C; C07C215/00; C07C215/02; C07C215/04; C07C215/20; A; A61; A61K; A61K31/00; A61K31/045; A61P; A61P31/00; A61P35/00; C07C205/00; C07C205/13; C07C205/14; C07C205/15; C07C215/06; C07C215/10; C07C215/22; C07C215/28; C07C215/42; C07C217/00; C07C217/02; C07C217/48; C07C217/54; C07C217/56; C07C217/58; C07C255/00; C07C255/49; C07C255/58; C07C317/00; C07C317/26; C07C317/32; C07C323/00; C07C323/23; C07C323/31; C07C323/32; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D263/00; C07D263/52; C07D263/62; C07D263/64; C07D295/00; C07D295/04; C07D295/12; C07D295/135; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07D319/00; C07D319/04; C07D319/06; C07J; C07J63/00; C07J63/008; C07C2601/00; C07C2601/12; C07C2601/14; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/22; C07C2603/24; C07C2603/26; C07C2603/40; C07C2603/42; C07C2603/48; C07C2603/50
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
247 words
A compound of formula (I) ArCH.sub.2 R.sup.1 (I) wherein Ar is a fluoranthene ring optionally substituted by one or two substituents, said substituents containing not more than four carbon atoms in total when taken together, being the same or different and are selected from halogen; cyano; C 1-4 alkyl or C 1-4 alkoxy, each optionally substituted by hydroxy or C 1-2 alkoxy; halogen substituted C 1-2 alkyl or C 1-2 alkoxy; a group S(O) n R 2 wherein n is an integer 0, 1 or 2 and R 2 is C 1-2 alkyl optionally substituted by hydroxy or C 1-2 alkoxy; or the fluoranthene ring is optionally substituted by a group NR 3 R 4 containing not more than 5 carbon atoms wherein R 3 and R 4 are the same or different and each is a C 1-3 alkyl; R 1 contains not more than eight carbon atoms and is a group ##STR11## wherein m is 0 or 1; R 5 is hydrogen; R 6 and R 7 are the same or different and each is hydrogen or C 1-3 alkyl optionally substituted by hydroxy; R 8 and R 9 are the same or different and each is hydrogen or C 1-3 alkyl; ##STR12## is a five- or six-membered saturated carbocyclic ring; R 10 is hydrogen, methyl or hydroxymethyl; R 11 , R 12 and R 13 are the same or different and each is hydrogen or methyl; R 14 is hydrogen, methyl, hydroxy, or hydroxymethyl.
Claim 2
Dependent Claim
247 words
A compound of formula (I) ArCH.sub.2 R.sup.1 (I) wherein Ar is a fluoranthene ring optionally substituted by one or two substituents, said substituents containing not more than four carbon atoms in total when taken together, being the same or different and are selected from halogen; cyano; C 1-4 alkyl or C 1-4 alkoxy, each optionally substituted by hydroxy or C 1-2 alkoxy; halogen substituted C 1-2 alkyl or C 1-2 alkoxy; a group S(O) n R 2 wherein n is an integer 0, 1 or 2 and R 2 is C 1-2 alkyl optionally substituted by hydroxy or C 1-2 alkoxy; or the fluoranthene ring is optionally substituted by a group NR 3 R 4 containing not more than 5 carbon atoms wherein R 3 and R 4 are the same or different and each is a C 1-3 alkyl; R 1 contains not more than eight carbon atoms and is a group ##STR11## wherein m is 0 or 1; R 5 is hydrogen; R 6 and R 7 are the same or different and each is hydrogen or C 1-3 alkyl optionally substituted by hydroxy; R 8 and R 9 are the same or different and each is hydrogen or C 1-3 alkyl; ##STR12## is a five- or six-membered saturated carbocyclic ring; R 10 is hydrogen, methyl or hydroxymethyl; R 11 , R 12 and R 13 are the same or different and each is hydrogen or methyl; R 14 is hydrogen, methyl, hydroxy, or hydroxymethyl.
Claim 3
Dependent Claim
68 words
A compound of claim 1 wherein Ar is 3 or 7-fluoranthenyl, ##STR13## R 1 is ##STR14## wherein m is 0; R 16 is CH 2 OH, CH(CH 3 )OH or CH 2 CH 2 OH; R 17 is hydrogen, C 1-3 alkyl or CH 2 OH; R 18 is hydrogen or methyl; or a monomethyl or monoethyl ether thereof containing no more than 28 carbon atoms in total.
Claim 4
Dependent Claim
30 words
A compound of claim 2 wherein R 16 is CH 2 OH or CH(CH 3 )OH and R 17 is hydrogen, methyl, ethyl or CH 2 OH; Ar is 3-fluoranthenyl.
Claim 5
Dependent Claim
30 words
A compound of claim 3 wherein R 1 is a diol of the structure ##STR15## wherein R 19 is hydrogen or methyl and R 20 is hydrogen, methyl or ethyl.
Claim 6
Dependent Claim
10 words
A compound of claim 4 wherein R 20 is methyl.
Claim 7
Dependent Claim
28 words
A compound of claim 1 wherein a compound of formula I is selected from: 3-Methoxy-2-((3-fluoranthenylmethyl)amino)-2-methyl-1-propanol, (+-)(2R*,3S*)-2-((3-Fluoranthenylmethyl)amino)-2-methyl-1,3-butanediol, 2-Ethoxymethyl-2-((3-fluoranthenylmethyl)amino)-1,3-propanediol, (1α,2β,3α)-2-((3-Fluoranthenylmethyl)amino)-1,3-cyclohexanediol, 2-((3-Fluoranthenylmethyl)amino)-2-isopropyl-1,3-propanediol, 2-((3-Fluoranthenylmethyl)amino)-2-methyl-1,4-butanediol, 2-((4-Ethyl-3-fluoranthenyl)methyl)amino)-2-methyl-1,3-propanediol, 2-((8-Fluoranthenylmethyl)amino)-2-methyl-1,3-propanediol, 2-(((3-Chloro-8-fluoranthenyl)methyl)amino)-2-methyl-1,3-propanediol and 2-(((4-Chloro-8-fluoranthenyl)methyl)amino)-2-methyl-1,3-propanediol, 2-(((3-Ethyl-8-fluoranthenyl)methyl)amino)-2-methyl-1,3-propanediol and 1-(((4-Ethyl-8-fluoranthenyl)methyl)amino)-2-methyl-1,3-propanediol.
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