US4847254A
Expired / Lapsed
US
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CNS affecting 5-oxy-3-aminomethyl-dihydro-benzofurans and benzothiophenes
Assignee: H Lundbeck AS
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Filing: 1988-02-12
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Granted: 1989-07-11
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Expires: 2008-02-12
Abstract
Abstract The present invention relates to 3-aminomethyl derivatives of indane, dihydrobenzofurane, dihydrobenzothiophene, and indoline, acid addition salts thereof, isomers thereof, methods of preparation, pharmaceutical compositions and method of treating CNS-disorders such as schizophrenia, Parkinson's disease, depression, anxiety, migraine and senile dementia, or in the cure of cardiovascular diseases, by administering such a derivative.
Inventors
- 👤 Klaus P. Boegesoe
- 👤 Jens K. Perregaard
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 02:06
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/14; A; A61; A61P; A61P25/00; A61P25/04; A61P25/18; A61P25/24; A61P25/26; A61P43/00; A61P9/00; C07D307/00; C07D307/77; C07D307/78; C07D307/79; C07D307/81; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/58
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
175 words
A dihydrobenzofuran- or, dihydrobenzothiophene- of the following formula: ##STR14## wherein X is O or S, R 1 is hydrogen, lower alkyl (1-6 C-atoms) or lower alkenyl (2-6 C-atoms), branched or unbranched, optionally substituted with a hydroxy group, aralkyl with from 4-13 C-atoms inclusive, the aromatic group being phenyl, thienyl, imidazolyl, pyridyl or pyrimidyl, or cycloalkyl (3-6 C-atoms), R 2 is hydrogen, lower alkyl (1-6 C-atoms), branched or unbranched, provided that both R 1 and R 2 may not be hydrogen, R 3 is 5-hydroxy, optionally substituted with ##STR15## in which R 5 is alkyl (1-20 C-atoms), branched or unbranched, cycloalkyl (3-6 C-atoms), adamantyl, aralkyl (4-13 C-atoms inclusive) or a phenyl or lower alkylphenyl group, R 6 is hydrogen or as R 5 , R 7 and R 8 are defined as R 6 , R 4 is hydrogen, halogen, lower alkyl (1-6 C-atoms), branched or unbranched, trifluoromethyl, cyano, nitro, SH, or NH 2 optionally substituted as shown above for R 3 , as well as enantiomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
175 words
A dihydrobenzofuran- or, dihydrobenzothiophene- of the following formula: ##STR14## wherein X is O or S, R 1 is hydrogen, lower alkyl (1-6 C-atoms) or lower alkenyl (2-6 C-atoms), branched or unbranched, optionally substituted with a hydroxy group, aralkyl with from 4-13 C-atoms inclusive, the aromatic group being phenyl, thienyl, imidazolyl, pyridyl or pyrimidyl, or cycloalkyl (3-6 C-atoms), R 2 is hydrogen, lower alkyl (1-6 C-atoms), branched or unbranched, provided that both R 1 and R 2 may not be hydrogen, R 3 is 5-hydroxy, optionally substituted with ##STR15## in which R 5 is alkyl (1-20 C-atoms), branched or unbranched, cycloalkyl (3-6 C-atoms), adamantyl, aralkyl (4-13 C-atoms inclusive) or a phenyl or lower alkylphenyl group, R 6 is hydrogen or as R 5 , R 7 and R 8 are defined as R 6 , R 4 is hydrogen, halogen, lower alkyl (1-6 C-atoms), branched or unbranched, trifluoromethyl, cyano, nitro, SH, or NH 2 optionally substituted as shown above for R 3 , as well as enantiomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
50 words
A compound according to claim 1, wherein X is O or S, R 3 is hydroxy or an acylated derivative thereof, R 4 is hydrogen, and R 1 and R 2 are each ethyl or propyl, or one is propyl and the other is either methyl, phenethyl, 2-thienylethyl or hydroxyethyl.
Claim 4
Dependent Claim
22 words
Compound of claim 1 selected from 2,3-Dihydro-3-(N,N-dipropylaminomethyl)-5-hydroxybenzofuran 2,3-dihydro-3-(N,-methyl-N-propylaminomethyl)-5-hydroxybenzofuran 2,3-dihydro-3-(N,N-dipropylaminomethyl)-5-isopropylaminocarbonyloxybenzofuran 2,3-dihydro-3-(N,N-dipropylaminomethyl)-5-(2-methylbenzoyloxy)-benzofuran and 2,3-dihydro-3-(N-propyl-N-(2-phenylethyl)aminomethyl)-5-hydroxybenzofuran, as well as enantiomers and non-toxic acid addition salts thereof.
Claim 5
Dependent Claim
32 words
A pharmaceutical composition suitable for treating central nervous system disorders in unit dosage form comprising--as an active ingredient--a compound as defined in claim 1, and one or more pharmaceutical diluents or carriers.
Claim 6
Dependent Claim
26 words
A pharmaceutical composition in unit dosage form, according to claim 4, wherein the active ingredient is present in an amount from 0.1-100 milligrams per unit dosage.
Claim 7
Dependent Claim
39 words
A method for the treatment of disorders of the central nervous system, comprising administering an effective amount of a compound of claim 1, as an active ingredient, and one or more pharmaceutical diluents or carriers, to a warmblooded animal.
Claim 8
Dependent Claim
24 words
A method according to claim 6, wherein the active ingredient is present in an amount from 0.1 to about 100 mg per unit dosage.
Claim 9
Dependent Claim
13 words
A method according to claim 6 wherein the animal is a human being.
Claim 10
Dependent Claim
35 words
A method for the treatment of disorders of the central nervous system, comprising the step of administering an effective amount of a compound of claim 1, as active ingredient, to a subject in need thereof.
Claim 11
Dependent Claim
25 words
A method according to claim 9, wherein the active ingredient is present in an amount of about 0.1 to about 100 mg per unit dosage.
References Cited (Backward Citations)
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