Patent US4924808A successfully refreshed from Google Patents.
US4980368A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Tryptamine compounds, and methods of cerebrovascular treatment therewith
Assignee: Beecham Wuelfing GmbH and Co KG
•
Filing: 1986-12-23
•
Granted: 1990-12-25
•
Expires: 2006-12-23
Abstract
Abstract A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein: R 1 is hydrogen, C 1-6 alkyl, C 1-6 alkoxy or halogen; R 2 and R 3 are both hydrogen or together represent a bond; R 4 is selected from C 1-6 alkyl, phenyl, phenyl C 1-4 alkyl, COR 8 where R 8 is hydroxy, C 1-6 alkoxy or NR 9 R 10 where R 9 and R 10 are independently hydrogen or C 1-4 alkyl and CH 2 OR 11 and R 11 is hydrogen, C 1-4 alkyl or C 1-4 alkanoyl; R 5 is hydrogen, C 1-6 alkyl or phenyl C 1-4 alkyl; R 6 is phenyl C 1-7 alkyl in which the phenyl moiety is optionally substituted by one or two of halogen, ortho-nitro, meta- or para-methoxy, methyl or NR 12 R 13 wherein R 12 and R 13 are independently hydrogen or C 1-6 alkyl or R 12 and R 13 together are C 2-6 polymethylene or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or C 1-4 alkyl, processes for its preparation and its use as a pharmaceutical.
Inventors
- 👤 Dietrich Thielke
- 👤 Dagmar Hoeltje
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 13:31
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/42; A; A61; A61P; A61P9/00; C07D209/10; C07D209/14; C07D209/16
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
219 words
A compound of the formula I ##STR25## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is alkyl of 1-6 carbon atoms, phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl moiety, COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylaminoethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole.
Claim 2
Dependent Claim
219 words
A compound of the formula I ##STR25## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is alkyl of 1-6 carbon atoms, phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl moiety, COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylaminoethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole.
Claim 3
Dependent Claim
202 words
A compound according to claim 1 of the formula II ##STR26## wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is alkyl of 1-6 carbon atoms, phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl moiety, COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; and R 7 is hydrogen or alkyl of 1-4 carbon atoms; R 6 1 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety unsubstituted or monosubsubstituted by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1- 6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy.
Claim 4
Dependent Claim
205 words
A compound according to claim 1 of the formula IIA ##STR27## wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is alkyl of 1-6 carbon atoms, phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl moiety, COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylamino-ethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole; and R 6 2 is phenylalkyl of 1-4 carbon atoms in the alkyl moiety unsubstituted or monosubstituted by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy.
Claim 5
Dependent Claim
250 words
A pharmaceutical composition useful for the treatment of cerebrovascular discorders and disorders associated with cerebral senility in humans and animals, which comprises a therapeutically effective amount of a compound of the formula I ##STR28## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is alkyl of 1-6 carbon atoms, phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl moiety, COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, in combination with a pharmaceutically acceptable carrier.
Claim 6
Dependent Claim
250 words
A pharmaceutical composition useful for the treatment of cerebrovascular discorders and disorders associated with cerebral senility in humans and animals, which comprises a therapeutically effective amount of a compound of the formula I ##STR28## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is alkyl of 1-6 carbon atoms, phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl moiety, COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, in combination with a pharmaceutically acceptable carrier.
Claim 7
Independent Claim
255 words
A method of treating cerebrovascular disorders and disorders associated with cerebral senility in humans and animals which comprises administering to a human or animal in need thereof a therapeutically effective amount of a compound of the formula I ##STR29## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is alkyl of 1-6 carbon atoms, phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl moiety, COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, in combination with a pharmaceutically acceptable carrier.
Claim 8
Independent Claim
255 words
A method of treating cerebrovascular disorders and disorders associated with cerebral senility in humans and animals which comprises administering to a human or animal in need thereof a therapeutically effective amount of a compound of the formula I ##STR29## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is alkyl of 1-6 carbon atoms, phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl moiety, COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, in combination with a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
13 words
A method according to claim 5 wherein R 4 is methyl or methoxycarbonyl.
Claim 10
Dependent Claim
206 words
A compound of the formula I ##STR30## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylamino-ethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole.
Claim 11
Dependent Claim
206 words
A compound of the formula I ##STR30## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylamino-ethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole.
Claim 12
Dependent Claim
11 words
A compound according to claim 7 wherein R 7 is hydrogen.
Claim 13
Dependent Claim
11 words
A compound according to claim 7 wherein R 1 is hydrogen.
Claim 14
Dependent Claim
15 words
A compound according to claim 7 wherein R 2 and R 3 are a bond.
Claim 15
Dependent Claim
11 words
A compound according to claim 7 wherein R 4 is methoxycarbonyl.
Claim 16
Dependent Claim
14 words
A compound according to claim 7 wherein R 5 is hydrogen, methyl or ethyl.
Claim 17
Dependent Claim
38 words
A compound according to claim 7 wherein R 6 is benzyl or 1-methyl-2-phenylethyl unsubstituted or substituted at the meta- or para- position by amino which moiety is unsubstituted or substituted by one or two methyl or ethyl moieties.
Claim 18
Dependent Claim
22 words
A compound according to claim 7 which is 1,2-dimethyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl]indole; 1,2-dimethyl-3-[2-(4-dimethylaminobenzyl)aminoethyl]indole; 2-methyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl]indole; 2-methyl-3-[2-(4-dimethylaminobenzyl)aminoethyl]indole; 2-methoxycarbonyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl)indole; or 2-methoxycarbonyl-3-[2-(4-dimethylaminobenzyl) aminoethyl)indole or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
47 words
A compound according to claim 7 or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen or alkyl of 1 to 6 carbon atoms; R 2 and R 3 together are a bond: and R 5 is hydrogen or alkyl of 1 to 6 carbon atoms.
Claim 20
Dependent Claim
14 words
The compound according to claim 7 which is 2-methoxycarbonyl-3-[(2-(4-dimethylaminobenzyl)aminoethyl]indole or the dihydrochloride salt thereof.
Claim 21
Dependent Claim
241 words
A pharmaceutical composition useful for the treatment of cerebrovascular disorders and disorders associated with cerebral senility in humans and animals which comprises a therapeutically effective amount of a compound of the formula I ##STR31## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or unsubstituted by 1 or 2 halo, ortho-nitro, meta- or para-methoxy, methyl or by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylamino-ethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole, in combination with a pharmaceutically acceptable carrier.
Claim 22
Dependent Claim
241 words
A pharmaceutical composition useful for the treatment of cerebrovascular disorders and disorders associated with cerebral senility in humans and animals which comprises a therapeutically effective amount of a compound of the formula I ##STR31## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or unsubstituted by 1 or 2 halo, ortho-nitro, meta- or para-methoxy, methyl or by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylamino-ethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole, in combination with a pharmaceutically acceptable carrier.
Claim 23
Dependent Claim
11 words
A composition according to claim 17 wherein R 7 is hydrogen.
Claim 24
Dependent Claim
11 words
A composition according to claim 17 wherein R 1 is hydrogen.
Claim 25
Dependent Claim
15 words
A composition according to claim 17 wherein R 2 and R 3 are a bond.
Claim 26
Dependent Claim
13 words
A composition according to claim 17 wherein R 4 is methyl or methoxycarbonyl.
Claim 27
Dependent Claim
14 words
A composition according to claim 17 wherein R 5 is hydrogen, methyl or ethyl.
Claim 28
Dependent Claim
38 words
A composition according to claim 17 wherein R 6 is benzyl or 1-methyl-2-phenylethyl unsubstituted or substituted at the meta- or para position by amino which moiety is unsubstituted or substituted by one or two methyl or ethyl moieties.
Claim 29
Dependent Claim
23 words
A composition according to claim 17 wherein the compound is 1,2-dimethyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl]indole; 1,2-dimethyl-3-[2-(4-dimethylaminobenzyl)aminoethyl]indole; 2-methyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl]indole; 2-methyl-3-[2-(4-dimethylaminobenzyl)aminoethyl]indole; 2-methoxycarbonyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl)indole; or 2-methoxycarbonyl-3-[2-(4-dimethylaminobenzyl)aminoethyl)indole or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim
186 words
A composition according to claim 17 of the formula II ##STR32## wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; and R 7 is hydrogen or alkyl of 1-4 carbon atoms; R 6 1 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety unsubstituted or monosubsubstituted by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy.
Claim 31
Dependent Claim
190 words
A composition according to claim 17 of the formula IIA ##STR33## wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylamino-ethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole; and R 6 2 is phenylalkyl of 1-4 carbon atoms in the alkyl moiety unsubstituted or monosubsubstituted by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy.
Claim 32
Dependent Claim
41 words
A composition according to claim 18 wherein R 1 is hydrogen or alkyl of 1 to 6 carbon atoms; R 2 and R 3 together are a bond; and R 5 is hydrogen or alkyl of 1 to 6 carbon atoms.
Claim 33
Dependent Claim
16 words
A composition according to claim 17 wherein the compound is 2-methoxycarbonyl-3-[2-(4-dimethylaminobenzyl)aminoethyl]indole or the dihydrochloride salt thereof.
Claim 34
Independent Claim
242 words
A method of treating disorders associated with cerebral senility in humans and animals which comprises administering to a human or animal in need thereof a therapeutically effective amount of a compound of the formula I ##STR34## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylaminoethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole, in combination with a pharmaceutically acceptable carrier.
Claim 35
Independent Claim
242 words
A method of treating disorders associated with cerebral senility in humans and animals which comprises administering to a human or animal in need thereof a therapeutically effective amount of a compound of the formula I ##STR34## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 6 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety wherein the phenyl moiety is unsubstituted or substituted by 1 or 2 halo, ortho-nitro, meta-or para-methoxy, methyl or by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylaminoethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole, in combination with a pharmaceutically acceptable carrier.
Claim 36
Dependent Claim
11 words
A method according to claim 29 wherein R 7 is hydrogen.
Claim 37
Dependent Claim
186 words
A method according to claim 29 of the formula II ##STR35## wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; and R 7 is hydrogen or alkyl of 1-4 carbon atoms; R 6 1 is phenylalkyl of 1-7 carbon atoms in the alkyl moiety unsubstituted or monosubsubstituted by NR 12 R 13 wherein R 12 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy.
Claim 38
Dependent Claim
190 words
A method according to claim 29 of the formula IIA ##STR36## wherein R 1 is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms or halo; R 2 and R 3 are both hydrogen or together are a bond; R 4 is COR 8 wherein R 8 is hydroxy, alkoxy of 1-6 carbon atoms or NR 9 R 10 wherein R 9 and R 10 are each hydrogen or alkyl of 1-4 carbon atoms or CH 2 OR 11 wherein R 11 is hydrogen, alkyl of 1-4 carbon atoms or alkanoyl of 1-4 carbon atoms; R 5 is hydrogen, alkyl of 1-6 carbon atoms or phenylalkyl of 1-4 carbon atoms in the alkyl moiety; R 7 is hydrogen or alkyl of 1-4 carbon atoms, excluding 7-methoxy-2-benzyl-3-(2-N-benzylamino-ethyl)indole and 2-hexyl-3-(2-N-phenethylamino-ethyl)indole; and R 6 2 is phenylalkyl of 1-4 carbon atoms in the alkyl moiety unsubstituted or monosubsubstituted by NR 12 R 13 wherein R 2 and R 13 are each hydrogen or alkyl of 1-6 carbon atoms or R 12 and R 13 together are polymethylene of 2-6 carbon atoms or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy.
Claim 39
Dependent Claim
11 words
A method according to claim 29 wherein R 1 is hydrogen.
Claim 40
Dependent Claim
15 words
A method according to claim 29 wherein R 2 and R 3 are a bond.
Claim 41
Independent Claim
13 words
A method according to claim wherein R 5 is hydrogen, methyl or ethyl.
Claim 42
Dependent Claim
38 words
A method according to claim 29 wherein R 6 is benzyl or 1-methyl-2-phenylethyl unsubstituted or substituted at the meta- or para position by amino which moiety is unsubstituted or substituted by one or two methyl or ethyl moieties.
Claim 43
Dependent Claim
23 words
A method according to claim 29 wherein the compound is 1,2-dimethyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl]indole; 1,2-dimethyl-3-[2-(4-dimethylaminobenzyl)aminoethyl]indole; 2-methyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl]indole; 2-methyl-3-[2-(4-dimethylaminobenzyl)aminoethyl]indole; 2-methoxycarbonyl-3-[2-(1-methyl-2-phenylethyl)aminoethyl)indole; or 2-methoxycarbonyl-3-[2-(4-dimethylaminobenzyl)aminoethyl)indole or a pharmaceutically acceptable salt thereof.
Claim 44
Dependent Claim
41 words
A method according to claim 29 wherein R 1 is hydrogen or alkyl of 1 to 6 carbon atoms; R 2 and R 3 together are a bond; and R 5 is hydrogen or alkyl of 1 to 6 carbon atoms.
Claim 45
Dependent Claim
16 words
A method according to claim 29 wherein the compound is 2-methoxycarbonyl-3-[2-(4-dimethylaminobenzyl)aminoethyl]indole or the dihydrochloride salt thereof.
References Cited (Backward Citations)
CA613852A
Cited
US3042685A
Cited
GB841524A
Cited
GB859223A
Cited
GB888426A
Cited
US3217029A
Cited
US3296072A
Cited
US3639414A
Cited
US3910953A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-12-24 | 1994-06-25 | 1994-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-12-24 | 1998-06-25 | 1998-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-12-24 | 2002-06-25 | 2002-12-25 | $7700.00 | Window Closed / Lapsed |