US5576321A
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Compounds having effects on serotonin-related systems
Assignee: Eli Lilly and Co
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Filing: 1995-06-06
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Granted: 1996-11-19
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Expires: 2015-06-06
Abstract
Abstract A series of hetero-oxy alkanamines are effective pharmaceuticals for the treatment of conditions related to or affected by the reuptake of serotonin and by the serotonin 1A receptor. The compounds are particularly useful for alleviating the symptoms of nicotine and tobacco withdrawal, and for the treatment of depression and other conditions for which serotonin reuptake inhibitors are used.
Inventors
- 👤 Joseph H. Krushinski, Jr.
- 👤 Kurt Rasmussen
- 👤 Vincent P. Rocco
- 👤 John M. Schaus
- 👤 Dennis C. Thompson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:30
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/08; A; A61; A61P; A61P13/00; A61P13/02; A61P15/00; A61P25/00; A61P25/04; A61P25/18; A61P25/20; A61P25/24; A61P25/26; A61P25/28; A61P25/30; A61P3/00; A61P3/04; A61P43/00; A61P9/00; A61P9/12; C07D401/00; C07D401/02; C07D401/10; C07D401/12; C07D401/14; C07D403/00; C07D403/02; C07D403/10; C07D403/12; C07D405/00; C07D405/02; C07D405/12; C07D405/14; C07D409/00; C07D409/02; C07D409/12; C07D409/14; C07D413/00; C07D413/02; C07D413/12; C07D471/00; C07D471/02; C07D471/08; C07D471/10; C07D491/00; C07D491/02; C07D491/10; C07D495/00; C07D495/02; C07D495/10; C07D513/00; C07D513/02; C07D513/04
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
193 words
A compound of the formula ##STR46## wherein r is 0-4; s is 0-1; D is a residue which combines with the carbon atoms to which it is attached to complete a pyrrolyl group; wherein X is hydrogen, phenyl, hydroxy or methoxy; provided that X is hydrogen or phenyl when r is 0; R is --NH--R.sup.1 II R 1 is piperidinyl, piperazino, morpholino or pyrrolyl, substituted with 0-1 phenyl or benzyl group or 0-4 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; which phenyl or benzyl group is substituted with 0-2 C 1 -C 3 alkyl, halo, trifluoromethyl or C 1 -C 3 alkoxy groups; or R 1 is ##STR47## n and m are independently 4-5, and the group of Formula VI may be substituted with 0-1 oxo group and 0-2 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; or R 1 is C 1 -C 4 alkyl, substituted with pyrrolyl, furyl, thienyl, morpholinyl, piperidinyl, tetrahydropyrrolyl, piperazinyl, tetrahydrofuryl, benzazepinyl, dibenzazepinyl or quinotinyl, substituted with 0-4 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
193 words
A compound of the formula ##STR46## wherein r is 0-4; s is 0-1; D is a residue which combines with the carbon atoms to which it is attached to complete a pyrrolyl group; wherein X is hydrogen, phenyl, hydroxy or methoxy; provided that X is hydrogen or phenyl when r is 0; R is --NH--R.sup.1 II R 1 is piperidinyl, piperazino, morpholino or pyrrolyl, substituted with 0-1 phenyl or benzyl group or 0-4 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; which phenyl or benzyl group is substituted with 0-2 C 1 -C 3 alkyl, halo, trifluoromethyl or C 1 -C 3 alkoxy groups; or R 1 is ##STR47## n and m are independently 4-5, and the group of Formula VI may be substituted with 0-1 oxo group and 0-2 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; or R 1 is C 1 -C 4 alkyl, substituted with pyrrolyl, furyl, thienyl, morpholinyl, piperidinyl, tetrahydropyrrolyl, piperazinyl, tetrahydrofuryl, benzazepinyl, dibenzazepinyl or quinotinyl, substituted with 0-4 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
17 words
A compound of claim 1 wherein X is hydrogen or hydroxy, and D completes a pyrrolyl group.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein r is 1-3.
Claim 5
Dependent Claim
9 words
A compound of claim 3 wherein s is 0.
Claim 6
Dependent Claim
16 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a compound of claim 1.
Claim 7
Independent Claim
219 words
A method of affecting the serotonin 1A receptor which comprises administering to a subject in need of such treatment an effective amount of a compound of the formula ##STR48## wherein r is 0-4; s is 0-1; D is a residue which combines with the carbon atoms to which it is attached to complete a pyrrolyl group; wherein X is hydrogen, phenyl, hydroxy or methoxy; provided that X is hydrogen or phenyl when r is 0; R is --NH--R.sup.1 II R 1 is piperidinyl, adamantyl, piperazino, morpholino or pyrrolyl, substituted with 0-1 phenyl or benzyl group or 0-4 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; which phenyl or benzyl group is substituted with 0-2 C 1 -C 3 alkyl, halo, trifluoromethyl or C 1 -C 3 alkoxy groups; or R 1 is ##STR49## n and m are independently 4-5, and the group of Formula VI may be substituted with 0-1 oxo group and 0-2 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; or R 1 is C 1 -C 4 alkyl, substituted with pyrrolyl, adamantyl, furyl, thienyl, pyridinyl, morpholinyl, piperidinyl, tetrahydropyrrolyl, piperazinyl, tetrahydrofuryl, benzazepinyl, dibenzazepinyl or quinolinyl, substituted with 0-4 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; or a pharmaceutically acceptable salt thereof.
Claim 8
Independent Claim
219 words
A method of affecting the serotonin 1A receptor which comprises administering to a subject in need of such treatment an effective amount of a compound of the formula ##STR48## wherein r is 0-4; s is 0-1; D is a residue which combines with the carbon atoms to which it is attached to complete a pyrrolyl group; wherein X is hydrogen, phenyl, hydroxy or methoxy; provided that X is hydrogen or phenyl when r is 0; R is --NH--R.sup.1 II R 1 is piperidinyl, adamantyl, piperazino, morpholino or pyrrolyl, substituted with 0-1 phenyl or benzyl group or 0-4 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; which phenyl or benzyl group is substituted with 0-2 C 1 -C 3 alkyl, halo, trifluoromethyl or C 1 -C 3 alkoxy groups; or R 1 is ##STR49## n and m are independently 4-5, and the group of Formula VI may be substituted with 0-1 oxo group and 0-2 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; or R 1 is C 1 -C 4 alkyl, substituted with pyrrolyl, adamantyl, furyl, thienyl, pyridinyl, morpholinyl, piperidinyl, tetrahydropyrrolyl, piperazinyl, tetrahydrofuryl, benzazepinyl, dibenzazepinyl or quinolinyl, substituted with 0-4 C 1 -C 3 alkyl, C 1 -C 3 alkoxy or halo groups; or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
24 words
A method of claim 6 wherein the compound is a compound wherein r is 1-3, s is 0, and X is hydrogen or hydroxy.
Claim 10
Dependent Claim
29 words
A method of preventing or alleviating the symptoms caused by withdrawal or partial withdrawal from the use of tobacco or of nicotine which comprises the method of claim 6.
Claim 11
Dependent Claim
24 words
A method of claim 8 wherein the compound is a compound wherein r is 1-3, s is 0, and X is hydrogen or hydroxy.
Claim 12
Dependent Claim
12 words
A method of treating anxiety which comprises the method of claim 6.
Claim 13
Dependent Claim
24 words
A method of claim 6 wherein the compound is a compound wherein r is 1-3, s is 0, and X is hydrogen or hydroxy.
Claim 14
Dependent Claim
45 words
A method of treating a condition chosen from the group consisting of hypertension, cognitive disorders, psychosis, sleep disorders, gastric motility disorders, sexual dysfunction, brain trauma, memory loss, eating disorders and obesity, substance abuse, obsessive-compulsive disease, panic disorder and migraine, comprising the method of claim 6.
Claim 15
Dependent Claim
45 words
A method of potentiating the action of a serotonin reuptake inhibitor in increasing the availability of serotonin, norepinephrine and dopamine in the brain, comprising administering to a subject in need of such treatment a serotonin reuptake inhibitor in combination with the method of claim 6.
Claim 16
Dependent Claim
16 words
A method of claim 8 wherein a serotonin reuptake inhibitor is also administered to the subject.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-11-19 | 2000-05-20 | 2000-11-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-11-19 | 2004-05-20 | 2004-11-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-11-19 | 2008-05-20 | 2008-11-19 | $7700.00 | Window Closed / Lapsed |