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US3976776A Expired / Lapsed US ⏱️ 0.0 years remaining

Tranquilizer process employing N-(heteroarcyclic)piperazinylalkylazaspiroalkanediones

Assignee: Mead Johnson and Co LLC
•
Filing: 1975-07-14
•
Granted: 1976-08-24
•
Expires: 1995-07-14
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Abstract

Abstract The present invention concerns the class of heterocyclic carbon compounds comprised of N-(heteroarcyclic)piperazinylalkyl derivatives of azaspiroalkanediones which have potent and specific tranquilizing action and anti-emetic properties. Typical embodiments of this invention are 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione and 8-[4-[4-(2-pyridyl)-1-piperazinyl]-butyl]-8-azaspiro[4.5]decane-7,9-dione.

Inventors

  • 👤 Yao Hua Wu
  • 👤 James W. Rayburn

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 12:54
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/14; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/495

Claims Analysis

Total Claims: 42
Claim 1
Independent Claim 183 words
The process for eliciting tranquilizing effect in a mammal which comprises administering systemically to a mammal in need thereof an effective tranquilizer dose of from about 0.01 to about 40 mg./kg. of body weight of said host of a compound selected from a group consisting of compounds having the formula: ##SPC13## wherein n is the integer 4 or 5; A is a divalent straight or branched alkylene chain of 2 to 6 carbon atoms inclusive and connects the nitrogen atoms as shown through at least 2 carbon atoms; B is a heteroarcyclic represented by the symbol ##SPC14## W and Y are independently selected from the group consisting of CH and nitrogen, R 1 and R 2 are independently selected from the group consisting of hydrogen, lower alkyl from 1 to 4 carbon atoms inclusive, lower alkoxy of from 1 to 4 carbon atoms inclusive, hydroxy, amino, alkylthio of from 1 to 4 carbon atoms inclusive, halogen, trifluoromethyl, alkanoamido of 1 to 6 carbon atoms inclusive, and alkanesulfonamido of 1 to 6 carbon atoms inclusive, and a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 183 words
The process for eliciting tranquilizing effect in a mammal which comprises administering systemically to a mammal in need thereof an effective tranquilizer dose of from about 0.01 to about 40 mg./kg. of body weight of said host of a compound selected from a group consisting of compounds having the formula: ##SPC13## wherein n is the integer 4 or 5; A is a divalent straight or branched alkylene chain of 2 to 6 carbon atoms inclusive and connects the nitrogen atoms as shown through at least 2 carbon atoms; B is a heteroarcyclic represented by the symbol ##SPC14## W and Y are independently selected from the group consisting of CH and nitrogen, R 1 and R 2 are independently selected from the group consisting of hydrogen, lower alkyl from 1 to 4 carbon atoms inclusive, lower alkoxy of from 1 to 4 carbon atoms inclusive, hydroxy, amino, alkylthio of from 1 to 4 carbon atoms inclusive, halogen, trifluoromethyl, alkanoamido of 1 to 6 carbon atoms inclusive, and alkanesulfonamido of 1 to 6 carbon atoms inclusive, and a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 10 words
The process of claim 1 comprising the administration of 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]-decane-7,9-dione.
Claim 4
Dependent Claim 11 words
The process of claim 1 comprising the administration of 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]-decane-7,9-dione hydrochloride.
Claim 5
Dependent Claim 10 words
The process of claim 1 comprising the administration of 8-[4-[4-(2-pyridyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 6
Dependent Claim 11 words
The process of claim 1 comprising the administration of 8-[4-[4-(2-pyridyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 7
Dependent Claim 10 words
The process of claim 1 comprising the administration of 8-[2-[4-(2-pyridyl)-1-piperazinyl]ethyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 8
Dependent Claim 11 words
The process of claim 1 comprising the administration of 8-[2-[4-(2-pyridyl)-1-piperazinyl]ethyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 9
Dependent Claim 10 words
The process of claim 1 comprising the administration of 8-[2-[4-(2-pyrimidinyl-1-piperazinyl]ethyl]-8-azaspiro[4.5]-decane-7,9-dione.
Claim 10
Dependent Claim 11 words
The process of claim 1 comprising the administration of 8-[2-[4-(2-pyrimidinyl)-1-piperazinyl]ethyl]-8-azaspiro[4.5]-decane-7,9-dione hydrochloride.
Claim 11
Dependent Claim 10 words
The process of claim 1 comprising the administration of 8-[3-[4-(2-pyrimidinyl)-1-piperazinyl]propyl]-8-azaspiro[4.5]-decane-7,9-dione.
Claim 12
Dependent Claim 11 words
The process of claim 1 comprising the administration of 8-[3-[4-(2-pyrimidinyl)-1-piperazinyl]propyl]-8-azaspiro[4.5]-decane-7,9-dione hydrochloride.
Claim 13
Dependent Claim 10 words
The process of claim 1 comprising the administration of 8-[5-[4-(2-pyrimidinyl)-1-piperazinyl]pentyl]-8-azaspiro[4.5]-decane-7,9-dione.
Claim 14
Dependent Claim 11 words
The process of claim 1 comprising the administration of 8-[5-[4-(2-pyrimidinyl)-1-piperazinyl]pentyl]-8-azaspiro[4.5]-decane-7,9-dione hydrochloride.
Claim 15
Dependent Claim 10 words
The process of clam 1 comprising the administration of 8-[3-[4-(6-methoxy-2-pyridyl)-2-piperazinyl]propyl]-8-azaspiro-[4.5]decane-7,9-dione.
Claim 16
Dependent Claim 10 words
The process of clam 1 comprising the administration of 8-[3-[4-(6-methoxy-2-pyridyl)-2-piperazinyl]propyl]-8-azaspiro-[4.5]decane-7,9-dione.
Claim 17
Dependent Claim 11 words
The process of clam 1 comprising the administration of 8-[3-[4-(6-methoxy-2-pyridyl)-1-piperazinyl]propyl]-8-azaspiro-[4.5]decane-7,9-dione hydrochloride.
Claim 18
Dependent Claim 11 words
The process of clam 1 comprising the administration of 8-[3-[4-(6-methoxy-2-pyridyl)-1-piperazinyl]propyl]-8-azaspiro-[4.5]decane-7,9-dione hydrochloride.
Claim 19
Dependent Claim 10 words
The process of claim 1 comprising the administration of 3-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-3-azaspiro[5.5]-undecane-2,4-dione.
Claim 20
Dependent Claim 11 words
The process of claim 1 comprising the administration of 3-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-3-azaspiro[5.5]-undecane-2,4-dione hydrochloride.
Claim 21
Dependent Claim 10 words
The process of claim 1 comprising the administration of 8-[4-[4-(4,6-dimethyl-2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 22
Dependent Claim 11 words
The process of claim 1 comprising the administration of 8-[4-[4-(4,6-dimethyl-2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 23
Dependent Claim 186 words
A pharmaceutical composition in dosage unit form suitable for systemic administration to a mammalian host comprising a pharmaceutical carrier and sufficient compound to provide an effective daily dose of from 0.01 to 40 mg./kg. of body weight of said host, said compound being selected from the group consisting of compounds of the formula: ##SPC15## wherein n is the integer 4 or 5; A is a divalent straight or branched alkylene chain of 2 to 6 carbon atoms inclusive and connects the nitrogen atoms as shown through at least 2 carbon atoms; B is a heteroarcyclic represented by the symbol wherein ##SPC16## W and Y are independently selected from the group consisting of CH and nitrogen, R 1 and R 2 are independently selected from the group consisting of hydrogen, lower alkyl from 1 to 4 carbon atoms inclusive, lower alkoxy of from 1 to 4 carbon atoms inclusive, hydroxy, amino, alkylthio of 1 to 4 carbon atoms inclusive, halogen, trifluoromethyl, alkanoamido of 1 to 6 carbon atoms inclusive, and alkanesulfonamido of 1 to 6 carbon atoms inclusive, and a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 24
Dependent Claim 186 words
A pharmaceutical composition in dosage unit form suitable for systemic administration to a mammalian host comprising a pharmaceutical carrier and sufficient compound to provide an effective daily dose of from 0.01 to 40 mg./kg. of body weight of said host, said compound being selected from the group consisting of compounds of the formula: ##SPC15## wherein n is the integer 4 or 5; A is a divalent straight or branched alkylene chain of 2 to 6 carbon atoms inclusive and connects the nitrogen atoms as shown through at least 2 carbon atoms; B is a heteroarcyclic represented by the symbol wherein ##SPC16## W and Y are independently selected from the group consisting of CH and nitrogen, R 1 and R 2 are independently selected from the group consisting of hydrogen, lower alkyl from 1 to 4 carbon atoms inclusive, lower alkoxy of from 1 to 4 carbon atoms inclusive, hydroxy, amino, alkylthio of 1 to 4 carbon atoms inclusive, halogen, trifluoromethyl, alkanoamido of 1 to 6 carbon atoms inclusive, and alkanesulfonamido of 1 to 6 carbon atoms inclusive, and a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 25
Dependent Claim 7 words
The composition of claim 20 containing 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 26
Dependent Claim 8 words
The composition of claim 20 containing 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 27
Dependent Claim 7 words
The composition of claim 20 containing 8-[4-[4-(2-pyridyl)-1-piperazinyl)]butyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 28
Dependent Claim 8 words
The composition of claim 20 containing 8-[4-[4-(2-pyridyl)-1-piperazinyl)]butyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 29
Dependent Claim 7 words
The composition of claim 20 containing 8-[4-[4-(2-pyridyl)-1-piperazinyl]ethyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 30
Dependent Claim 8 words
The composition of claim 20 containing 8-[2-[4-(2-pyridyl)-1-piperazinyl]ethyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 31
Dependent Claim 7 words
The composition of claim 20 containing 8-[2-[4-(2-pyrimidinyl)-1-piperazinyl]ethyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 32
Dependent Claim 8 words
The composition of claim 20 containing 8-[2-[4-(2-pyrimidinyl)-1-piperazinyl]ethyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 33
Dependent Claim 7 words
The composition of claim 20 containing 8-[3-[4-(2-pyrimidinyl)-1-piperazinyl]propyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 34
Dependent Claim 8 words
The compositon of claim 20 containing 8-[3-[4-(2-pyrimidinyl)-1-piperazinyl]propyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 35
Dependent Claim 7 words
The composition of claim 20 containing 8-[5-[4-(2-pyrimidinyl)-1-piperazinyl]pentyl]-8-azaspiro[4.5]decane-7,9-dione.
Claim 36
Dependent Claim 8 words
The composition of claim 20 containing 8-[5-[4-(2-pyrimidinyl)-1-piperazinyl]pentyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 37
Dependent Claim 7 words
The composition of claim 20 containing 8-[3-[4-(6-methoxy-2-pyridyl)-1-piperazinyl]propyl]-8-azaspiro[4.5]decane-7.9-dione.
Claim 38
Dependent Claim 8 words
The composition of claim 20 containing 8-[3-[4-(6-methoxy-2-pyridyl)-1-piperazinyl]propyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride.
Claim 39
Dependent Claim 7 words
The composition of claim 20 containing 3-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-3-azaspiro[5.5]undecane-2,4-dione.
Claim 40
Dependent Claim 8 words
The composition of claim 20 containing 3-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-3-azaspiro[5.5]undecane-2,4-dione hydrochloride.
Claim 41
Dependent Claim 7 words
The composition of claim 20 containing 8-[4-[4-(4,6-dimethyl-2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]-decane-7,9-dione.
Claim 42
Dependent Claim 8 words
The composition of claim 20 containing 8-[4-[4-(4,6-dimethyl-2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]-decane-7,9-done hydrochloride.

References Cited (Backward Citations)

US3398151A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-08-24 1980-02-23 1980-08-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-08-24 1984-02-23 1984-08-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-08-24 1988-02-23 1988-08-24 $7700.00 Window Closed / Lapsed

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