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US4335126A Expired / Lapsed US ⏱️ 0.0 years remaining

1-[3-(3,4,5-Trimethoxyphenoxy)-2-hydroxy-propyl]-4-aryl-piperazine-derivatives having pharmaceutical activity

Assignee: Evonik Operations GmbH
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Filing: 1980-10-03
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Granted: 1982-06-15
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Expires: 2000-10-03
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Abstract

Abstract There are prepared compounds corresponding to the general formula ##STR1## in which R 1 is a hydrogen atom, a C 2 to C 6 -alkanoyl group, a C 3 to C 6 -alkenoyl group, a C 3 to C 6 -cycloalkyl carbonyl group, a benzoyl group, an alkoxybenzoyl group, a nicotinoyl group, a thienyl carbonyl group, a furyl carbonyl group, a phenylacetyl group or a C 1 to C 4 -alkoxyphenyl acetyl group and R 2 represents a phenyl, naphthyl or pyridyl group or such group substituted by the groups R 3 and R 4 , the groups R 3 and R 4 , which may be the same or different, each representing hydrogen, hydroxyl, fluorine, chlorine, bromine, a nitro group, a trifluoromethyl group, a C 1 to C 6 -alkyl group, a C 1 to C 6 -alkoxy group, a C 1 to C 6 -alkyl thio group, a C 1 to C 6 -alkyl sulphonyl group, a C 2 to C 6 -alkanoyl group, an amino group, an acylamino group or an acyloxy group in which the acyl is of the type defined in respect to R 1 , and their salts. The compounds are pharmacodynamically active.

Inventors

  • 👤 Axel Kleemann
  • 👤 Vladimir Jakovlev
  • 👤 Klaus Thiemer
  • 👤 Jurgen Engel

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 10:15
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088

Claims Analysis

Total Claims: 44
Claim 1
Independent Claim 87 words
A compound corresponding to the formula ##STR13## in which R 1 is hydrogen atom or C 2 to C 6 -alkanoyl group, and R 2 represents phenyl substituted by the groups R 3 and R 4 , the R 3 and R 4 each representing hydrogen, hydroxyl, C 1 to C 6 -alkanoxy group, C 2 to C 6 -alkanoyloxy group, amino group or C 2 -C 6 -alkanoylamino group with proviso at least one of R 3 and R 4 is not hydrogen and their salts.
Claim 2
Dependent Claim 87 words
A compound corresponding to the formula ##STR13## in which R 1 is hydrogen atom or C 2 to C 6 -alkanoyl group, and R 2 represents phenyl substituted by the groups R 3 and R 4 , the R 3 and R 4 each representing hydrogen, hydroxyl, C 1 to C 6 -alkanoxy group, C 2 to C 6 -alkanoyloxy group, amino group or C 2 -C 6 -alkanoylamino group with proviso at least one of R 3 and R 4 is not hydrogen and their salts.
Claim 3
Dependent Claim 13 words
A compound according to claim 1 in the form of the free base.
Claim 4
Dependent Claim 16 words
A compound according to claim 1 in the form of a pharmaceutically acceptable acid addition salt.
Claim 5
Dependent Claim 20 words
A compound according to claim 1 wherein R 3 and R 4 substituents are in the ortho and para positions.
Claim 6
Dependent Claim 18 words
A compound according to claim 1 wherein R 3 is hydrogen and R 4 is other than hydrogen.
Claim 7
Dependent Claim 11 words
A compound according to claim 1 wherein R 1 is hydrogen.
Claim 8
Dependent Claim 11 words
A compound according to claim 6 wherein R 3 is hydrogen.
Claim 9
Dependent Claim 16 words
A compound according to claim 7 wherein R 4 is C 1 to C 4 alkoxy.
Claim 10
Dependent Claim 16 words
A compound according to claim 8 wherein R 4 is C 1 to C 6 alkoxy.
Claim 11
Dependent Claim 11 words
A compound according to claim 9 wherein R 4 is methoxy.
Claim 12
Dependent Claim 11 words
A compound according to claim 10 wherein R 4 is 2-methoxy.
Claim 13
Dependent Claim 11 words
A compound according to claim 10 wherein R 4 is 3-methoxy.
Claim 14
Dependent Claim 11 words
A compound according to claim 7 wherein R 4 is hydroxy.
Claim 15
Dependent Claim 11 words
A compound according to claim 13 wherein R 4 is 2-hydroxy.
Claim 16
Dependent Claim 15 words
A compound according to claim 7 wherein R 4 is C 2 -C 6 -alkanoylamino.
Claim 17
Dependent Claim 11 words
A compound according to claim 15 wherein R 4 is acetamido.
Claim 18
Dependent Claim 11 words
A compound according to claim 16 wherein R 4 is 2-acetamido.
Claim 19
Dependent Claim 11 words
A compound according to claim 7 wherein R 4 is amino.
Claim 20
Dependent Claim 11 words
A compound according to claim 18 wherein R 4 is 2-amino.
Claim 21
Dependent Claim 16 words
A compound according to claim 7 wherein R 4 is C 2 to C 6 alkanoyloxy.
Claim 22
Dependent Claim 11 words
A compound according to claim 20 wherein R 4 is acetoxy.
Claim 23
Dependent Claim 11 words
A compound according to claim 21 wherein R 4 is 2-acetoxy.
Claim 24
Dependent Claim 16 words
A compound according to claim 1 where R 1 is C 2 to C 6 -alkanoyloxy.
Claim 25
Dependent Claim 11 words
A compound according to claim 23 where R 1 is acetyl.
Claim 26
Dependent Claim 11 words
A compound according to claim 24 wherein R 3 is hydrogen.
Claim 27
Dependent Claim 16 words
A compound according to claim 25 wherein R 4 is C 1 to C 6 alkoxy.
Claim 28
Dependent Claim 11 words
A compound according to claim 26 where R 4 is methoxy.
Claim 29
Dependent Claim 11 words
A compound according to claim 27 where R 4 is 2-methoxy.
Claim 30
Dependent Claim 26 words
A medicament containing as an active ingredient in an amount sufficient to exert a tranquilizing effect a compound of claim 1 together with a pharmaceutical excipient.
Claim 31
Dependent Claim 30 words
A method of imparting a neuroleptic or tranquilizing effect in a mammal comprising administering to the mammal an amount of a compound of claim 1 sufficient to cause said effect.
Claim 32
Dependent Claim 12 words
A method according to claim 30 wherein the compound is administered orally.
Claim 33
Dependent Claim 20 words
A method according to claim 31 wherein there is administered orally at least 0.1 mg/kg body weight of the mammal.
Claim 34
Dependent Claim 12 words
A method according to claim 30 wherein the compound is administered intravenously.
Claim 35
Dependent Claim 20 words
A method according to claim 33 wherein there is administered intravenously at least 0.01 mg/kg body weight of the mammal.
Claim 36
Dependent Claim 40 words
A method according to claim 30 wherein R 1 is hydrogen, R 3 is hydrogen and R 4 is 2-methoxy, 3-methoxy, 2-hydroxy, 2-acetamido, 2-amino or 2-acetoxy or R 1 is acetyl, R 3 is hydrogen and R 4 is 2-methoxy.
Claim 37
Dependent Claim 11 words
A method according to claim 35 wherein R 1 is hydrogen.
Claim 38
Dependent Claim 11 words
A method according to claim 36 where R 4 is 2-methoxy.
Claim 39
Dependent Claim 11 words
A method according to claim 36 where R 4 is 2-hydroxy.
Claim 40
Dependent Claim 11 words
A method according to claim 38 where R 4 is 2-acetamido.
Claim 41
Dependent Claim 11 words
A method according to claim 36 where R 4 is 2-amino.
Claim 42
Dependent Claim 11 words
A method according to claim 36 where R 4 is 2-acetoxy.
Claim 43
Dependent Claim 11 words
A method according to claim 36 where R 4 is 3-methoxy.
Claim 44
Dependent Claim 20 words
A method according to claim 35 wherein R 1 is acetyl, R 3 is hydrogen and R 4 is 2-methoxy.

References Cited (Backward Citations)

DE2814168A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-06-14 1985-12-14 1986-06-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-06-14 1989-12-14 1990-06-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-06-14 1993-12-14 1994-06-15 $7700.00 Window Closed / Lapsed

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