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US4144337A Expired / Lapsed US ⏱️ 0.0 years remaining

1,4-Substituted piperazinyl derivatives useful as psychostimulants

Assignee: Sandoz AG
•
Filing: 1977-02-14
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Granted: 1979-03-13
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Expires: 1997-02-14
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Abstract

Abstract The invention provides compounds of formula I, <IMAGE> I wherein each of R1 and R4, which may be the same or different, is hydrogen, halogen, alkyl or alkoxy; each of R2 and R3 is hydrogen, or together, oxygen; B and D together with the carbon atoms to which they are bound may be a benzene ring or a substituted or unsubstituted thiophene ring and A may, for example, be oxygen, sulpur, -CH2-O-, -CH2-S, ethylene or vinylene, useful as psychostimulants and vigilance-increasing agents.

Inventors

  • 👤 Jean-Michel Bastian

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 02:23
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/02; C07D295/027; C07D295/03; A; A61; A61P; A61P25/00; A61P25/26; C07D311/00; C07D311/02; C07D311/78; C07D311/80; C07D311/82; C07D311/84; C07D311/88; C07D333/00; C07D333/50; C07D333/78; C07D333/80

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 252 words
A compound of formula I, ##STR17## wherein each of R 1 and R 4 , which may be the same or different, is hydrogen, halogen of atomic number from 9 to 35, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, either each of R 2 and R 3 is hydrogen or R 2 and R 3 together are oxygen, either B and D together with the carbon atoms to which they are bound form a benzene ring, or B is sulphur and B and D together with the carbon atoms to which they are bound form a thiophene ring which may be substituted in the position α- to the sulphur atom with halogen of atomic number from 9 to 35 or alkyl of 1 to 4 carbon atoms, and when B and D together with the caron atoms to which they are bound form a benzene ring, A is oxygen, sulphur, --CH 2 --O-- or --CH 2 --S-- in either orientation, or when B is sulphur and B and D together with the carbon atoms to which they are bound form a substituted or unsubstituted thiophene ring, A is a group of formula ##STR18## wherein each of R 7 and R 8 , which may be the same or different, is hydrogen or alkyl of 1 to 4 carbon atoms and either each of E and F is hydrogen or E and F together form a bond, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 252 words
A compound of formula I, ##STR17## wherein each of R 1 and R 4 , which may be the same or different, is hydrogen, halogen of atomic number from 9 to 35, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, either each of R 2 and R 3 is hydrogen or R 2 and R 3 together are oxygen, either B and D together with the carbon atoms to which they are bound form a benzene ring, or B is sulphur and B and D together with the carbon atoms to which they are bound form a thiophene ring which may be substituted in the position α- to the sulphur atom with halogen of atomic number from 9 to 35 or alkyl of 1 to 4 carbon atoms, and when B and D together with the caron atoms to which they are bound form a benzene ring, A is oxygen, sulphur, --CH 2 --O-- or --CH 2 --S-- in either orientation, or when B is sulphur and B and D together with the carbon atoms to which they are bound form a substituted or unsubstituted thiophene ring, A is a group of formula ##STR18## wherein each of R 7 and R 8 , which may be the same or different, is hydrogen or alkyl of 1 to 4 carbon atoms and either each of E and F is hydrogen or E and F together form a bond, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 28 words
A method of increasing vigilance in animals, which comprises administering to an animal in need of such treatment a therapeutically effective amount of a compound of claim 1.
Claim 4
Dependent Claim 31 words
A method of stimulating the central nervous system in animals, which comprises administering to an animal in need of such treatment a therapeutically effective amount of a compound of claim 1.
Claim 5
Dependent Claim 18 words
A pharmaceutical composition comprising a compound of claim 1, in association with a pharmaceutically acceptable diluent or carrier.
Claim 6
Dependent Claim 8 words
A compound of claim 1, which is 1-cinnamyl-4-(9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-yl)-piperazine.
Claim 7
Dependent Claim 44 words
A compound of claim 1, wherein R 1 , R 2 , R 3 and R 4 are as previously defined, B and D together with the carbon atoms to which they are bound form a benzene ring and A is oxygen or sulphur.
Claim 8
Dependent Claim 48 words
A compound of claim 1, wherein R 1 , R 2 , R 3 and R 4 are as previously defined, B and D together with the carbon atoms to which they are bound form a benzene ring and A is --CH 2 --O-- or --CH 2 --S--.
Claim 9
Dependent Claim 80 words
A compound of claim 1, wherein B is sulphur and B and D together with the carbon atoms to which they are bound form a substituted or unsubstituted thiophene ring, A is a group of formula ##STR19## wherein each of R 7 and R 8 , which may be the same or different, is hydrogen or alkyl of 1 to 4 carbon atoms and either each of E and F is hydrogen or E and F together form a bond.
Claim 10
Dependent Claim 14 words
A compound of claim 1, wherein R 2 and R 3 together are oxygen.
Claim 11
Dependent Claim 32 words
The compound according to claim 8 in which R 1 is hydrogen, R 2 and R 3 together is oxygen, R 4 is hydrogen and A is --CH 2 --CH 2 --.
Claim 12
Dependent Claim 32 words
The compound according to claim 7 in which R 1 , R 2 , R 3 , R 4 , and A are H, H, H, H and --CH 2 --S--, respectively.
Claim 13
Dependent Claim 30 words
The compound according to claim 7 in which R 1 is hydrogen, R 2 and R 3 together is oxygen, R 4 is hydrogen and A is --CH 2 --S--.
Claim 14
Dependent Claim 9 words
The compound according to claim 6 which is 1-cinnamyl-4-(thioxanthen-9-yl)-piperazine.
Claim 15
Dependent Claim 29 words
The compound according to claim 6 in which R 1 , R 2 , R 3 , R 4 and A are H, H, H, H and --O--, respectively.

References Cited (Backward Citations)

US2882271A Cited
US3459745A Cited
US3480624A Cited
US3511841A Cited
US3719679A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-03-12 1982-09-11 1983-03-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-03-12 1986-09-11 1987-03-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-03-12 1990-09-11 1991-03-13 $7700.00 Window Closed / Lapsed

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