US3717634A - N-(heteroarcyclic)piperazinylalkyl-azaspiroalkanediones - Google Patents

N-(heteroarcyclic)piperazinylalkyl-azaspiroalkanediones Download PDF

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Publication number
US3717634A
US3717634A US00879604A US87960469A US3717634A US 3717634 A US3717634 A US 3717634A US 00879604 A US00879604 A US 00879604A US 87960469 A US87960469 A US 87960469A US 3717634 A US3717634 A US 3717634A
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United States
Prior art keywords
formula
heteroarcyclic
compounds
reaction
piperazine
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Expired - Lifetime
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US00879604A
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English (en)
Inventor
Y Wu
J Rayburn
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Mead Johnson and Co LLC
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Mead Johnson and Co LLC
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Publication date
Priority to BE759371D priority Critical patent/BE759371A/xx
Application filed by Mead Johnson and Co LLC filed Critical Mead Johnson and Co LLC
Priority to US00879604A priority patent/US3717634A/en
Priority to ZA707826A priority patent/ZA707826B/xx
Priority to NL7017031A priority patent/NL7017031A/xx
Priority to FR7041860A priority patent/FR2073406B1/fr
Priority to DK589670AA priority patent/DK141753B/da
Priority to CH341874A priority patent/CH552608A/xx
Priority to GB5590870A priority patent/GB1332194A/en
Priority to CY886A priority patent/CY886A/xx
Priority to CH1741770A priority patent/CH552607A/xx
Priority to DE19702057845 priority patent/DE2057845A1/de
Priority to US312543A priority patent/US3907801A/en
Publication of US3717634A publication Critical patent/US3717634A/en
Application granted granted Critical
Priority to KE2691A priority patent/KE2691A/xx
Priority to HK61/77A priority patent/HK6177A/xx
Priority to MY151/77A priority patent/MY7700151A/xx
Priority to ES530335A priority patent/ES530335A0/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members

Definitions

  • n is the integer 4 or 5.
  • the symbol -A which connects the spiroglutarimide and the N-(heteroarcyolic)piperazine represents a divalent alkylene chain of 2 to 6 carbon atoms inclusive. Said alkylene chain can be straightor branched-chain hydrocarbon grouping in which the ring connecting bonds are on different carbon atoms such as hexamethylene (CH2 CH2 CH2CH CHzCHz) 2-methyl-1,2-propylene OH2C and the like.
  • the piperazine substituent represented by the symbol B is selected from the group consisting of imidazoyl and a heteroarcyclic. Said heteroarcyclic is represented by the symbol:
  • W and Y are independently selected from th group consisting of CH and nitrogen.
  • heteroancyclic as used herein, it is meant substituents comprised of nitrogen, carbon, and hydrogen which when taken together form a heteroaromatic system.
  • R and R substituents of the heteroarcyclic referred to above are independently selected from the group consisting of hydrogen, lower alkyl from 1 to 4 carbon atoms inclusive, alkoxy of from 1 to 4 carbon atoms inclusive, hydroxy, amino, alkylthio of 1 to 4 carbon atoms inclusive, halogen, trifiuoromethyl, alkanoamido of from 1 to 6 carbon atoms inclusive, and alkanesulfonamido of 1 to 6 carbon atoms inclusive.
  • lower alkyl as employed herein it is meant straight or branched chain alkyl radicals including methyl, ethyl, propyl, isopropyl, l-butyl, l-methylpropyl, Z-methylpropyl, and tert.-butyl.
  • alkyl fragment of the alkylthio substituent refers to straight or branched chain radicals described above.
  • Straight or the branched chain alkanes of 1 to 6 carbon atoms inclusive comprise the alkane radical of alkanoamido and alkanesulfonamido groupings.
  • non-toxic pharmaceutically acceptable acid addition salts refers to a combination of compounds of the present invention with relatively nontoxic inorganic or organic acids.
  • acids which may be used are sulfuric, phosphoric, hydrochloric, hydrobromic, hydroiodic, sulfamic, methanesulfonic, benzenesulfonic, para-toluenesulfonic, acetic, lactic, succinic, maleic, tartaric, citric, gluconic, ascorbic, benzoic, cinnamic, and related acids.
  • Conversion of the compounds of the present invention to pharmaceutically acceptable acid addition salts is accomplished by admixture of these compounds with substantially one chemical equivalent of any of the various acids hereinbefore defined.
  • the reactions are carried out in an inert solvent.
  • Suitable solvents are ethanol, benzene, ethyl acetate, ether, and halogenated hydrocarbons.
  • Method A is carried out by reacting a spiro-substituted glutaric anhydride of Formula II with the l-(w-aminoalkyl) 4 (heteroarcyclic)piperazines of Formula III to provide products of Formula I.
  • the reaction is carried out at elevated temperatures in a reaction inert organic solvent.
  • inert organic solvent as referred to herein is meant any protic or aprotic solvent or diluent which does not enter into the reaction to any substantial degree.
  • Pyridine is the preferred solvent.
  • Temperatures of about 100 C. to about 200 C. are preferred to facilitate completion of the reaction.
  • the duration of the reaction is critical only to the extent of providing maximum yields and reaction periods of from about 16 hr. to as much as 11 days are preferred. The lengthy reaction periods are necessary in some instances to obtain complete conversion of glutaric acid half-amides of Formula VIII which are initially formed when an anhydride of Formula II is combined with an amine of Formula III.
  • the glutaric acid half-amides of Formula VIII may be also transformed into Formula I products by heating in boiling acetic anhydride which is a well known standard organic procedure for ring closure useful in the formation of cyclic imides.
  • Method B is carried out under reaction conditions amply described in literature wherein teritary amines are formed by alkylation of a secondary amine with an alkyl halide, sulfate, phosphate, tosylate, or mesylate.
  • the Formula IV and Formula V intermediates are preferably reacted in an inert liquid reaction medium at temperatures of from about 60 C. to about 200 C. in the presence of a base suitable for use as an acid binding agent.
  • Sodium carbonate is a particularly preferred acid binding agent but other inorganic and tertiary organic base may be employed including other alkali and alkaline earth metal carbonates, bicarbonates, or hydrides and tertiary amines. Reaction periods ranging from about 2 hrs.
  • a particularly preferred solvent is n-butanol but any inert reaction medium is generally applicable to use in this reaction.
  • the duration of the reaction period depends upon the temperature and reaction solvent selected. By way of illustration, alkylation is facilitated and the reaction period is appreciably shortened if dimethylformamide is employed as the reaction medium compared to a solvent such as benzene.
  • Method C is another method useful for preparation of compounds of Formula I.
  • the spiroglutarirnide metal salt depicted by Formula VI is reacted with substituted piperazines of Formula VII.
  • Standard laboratory procedures are employed in carrying out the reaction such as those described for the alkylation step of the Gabriel synthesis-S. Gabriel, Ber. 20, 2224 (1887).
  • the reactants are combined in an inert reaction medium at temperatures ranging from about 25 C. to 200 C.
  • Preferred solvents for carrying out the reaction are dimethylformamide, acetone, benzene, n-butanol, ethanol and the like.
  • N (heteroarcyclic)piperazines of Formula V have been described by K. L. Howard at al. in J. Org. Chem., 18, 1484 (1953). Their procedures are applicable to the preparation of other N-(heteroarcyclic)piperazine intermediates not specifically disclosed but which are required for the preparation of compounds embraced in the present invention.
  • the l-(w-aminoalkyl)-4-(heteroarcyclic)piperazine of Formula III are obtained according to methods described in U.S. Pat. 3,398,151 by alkylation of N- (heteroarcyclic)piperazines of Formula V with haloalkylnitriles to provide 1 (w cyanoalkyl) 4 (heteroarcyclic)piperazine intermediates which are subsequently reduced to the Formula III substituted piperazines.
  • Reduction of the cyano intermediate may be carried out catalytically, preferably with W-6 Raney Nickel catalyst under high pressure, or alternatively with hydrazine and W-6 Raney Nickel.
  • the intermediate azaspirodecane-and undecanediones of Formula IV having the -A-X- group attached to the nitrogen atom are prepared according to procedures described in U.S. Pat. 3,398,151. Reaction 'of the glutaric anhydrides of Formula II with an alkanolamine of the formula H NAOH are carried out under conditions similar to those described hereinabove for Method A.
  • the resulting intermediate .g'lutarimide has the structure shown for Formula IV wherein X is OH. Esterification of this material is accomplished by conventional techniques well known to the art to provide the intermediate of Formula IV.
  • Conventional techniques which are adequately described in the literature are employed to provide the bromides, iodides, phosphates, sulfates, tosylates, and mesylates corresponding to Formula IV.
  • the piperazine reactant of Formula VII having the X-A- grouping attached to the nitrogen atom is prepared according to standard organic procedures.
  • Formula VIII This intermediate is then esterified according to conventional techniques well known to the art to provide the Formula VH reactants. For instance, thionyl chloride acting upon the compounds of Formula VIII provides the Formula VII intermediate in which X is chlorine. In a similar fashion, bromides, and iodides are prepared. Phosphates, sulfates, tosylates, mesylates corresponding to Formula VII are obtained with conventional laboratory techniques.
  • azaspiroalkanedione of Formula I are prepared in accordance with the unitary process of the present invention by reacting a piperazine of the Formula Y-bi NB Formula IX wherein Y is selected from the group consisting of hydrogen (Formula IXa), H 'NA- (Formula IXb), or XA-- (Formula IXc), and A and X are as hereinbefore defined, with a spirO-glutaric acid anhydride of Formula II.
  • N- (heteroarcyclic)piperazine alkyl derivatives of azaspirodecanediones and azaspiroundecanediones are highly active and specific tranquilizing agents and in addition also exhibit anti-emetic properties.
  • Present compounds are improved tranquilizing agents compared to the azaspirodecanediones and azaspiroundecanediones of United States Pat. 3,398,151, in that tranquilizing activity is more potent and specific.
  • Tranquilizing properties of the compounds of this invention can be demonstrated in rats by a shuttle box technique described by I. R. Albert and L. E. .Allen in the Ph'armacologist 4, '152 (1962). This test is designed to differentiate tranquilizing agents from non-specific central nervous system depressants such as sedatives and hypnotics. Tranquilizing effects are observed when the compounds of the present invention are administered intraperitoneally to the rat in dosages ranging from 1.5 to mg./kg. of body weight.
  • the tranquilizing action of the compounds of the present invention can be demonstrated in Rhesus monkeys by observing general behavioral effects. Intramuscular administration of present compounds to the monkey in dosages ranging from 2 to 16 mg./kg. of body Weight affords tranquilizing effects similar to those produced by chlorpromazine.
  • the compounds of the present invention are relatively non-toxic compounds.
  • the intraperitoneal 50% lethality dose of 8 [4 [4 (2pyrimidinyl)- 1 piperazinyl1butyl] 8 azaspiro[-4.5]decane-7,9-dione hydrochloride is 146 mg./kg. of body weight in the mouse.
  • Systemic administration of the compounds of the present invention to mammals in dosages ranging from about 0.01 to 40 mg./kg. of body weight per day induce effective tranquilizing responses in the mammalian recipient.
  • Oral, parenteral and rectal routes are preferred forms of systemic administration.
  • Forms of parenteral administration include intramuscular, intravenous, and subcutaneous administration.
  • the dosage of the compounds of the present invention will vary with the form and mode of administration and in some instances with the particular compound chosen. Generally, it will be found that when a compound of the present invention is administered orally, a larger quantity of the active agent is required to produce the same effect as a smaller quantity thereof which is given parenterally. It is generally preferred to administer the compounds of this invention at a concentration level that will produce effective tranquilizing effects without causing any harmful or deleterious side effects.
  • the compounds of Formula I may be administered to mammals in the form of free bases or in the form of non-toxic acid addition salts.
  • the compounds are relatively insoluble in water but are soluble in most organic sol vents such as lower alkyl alcohols, esters, acetones, chloroform and the like.
  • the present compounds in the form their acid addition salts are, in general, soluble in water and methanol but relatively insoluble in solvents such as benzene, ether, petroleum ether and the like.
  • the compounds of Formula I may be compounded and formulated into pharmaceutical compositions and unit dosage suitable for systemic administration.
  • Organic or inorganic Examples of representative compounds of the present invention prepared according to Procedure 1 are indicated in Table I.
  • compositions considered within the scope of this invention may take the form of tablets, powder, granules, capsules, suspensions, solutions, suppositories, elixirs, ointments and the like. Unit dosages ranging from about 1 to 500 mg. are employed.
  • Suitable pharmaceutical carriers comprise both solids and liquids such as corn starch, lactose, calcium phosphate, stearic acid, polyethylene glycol, water, sesame seed oil, peanut oil, propylene glycol, and the like.
  • the azaspiroalkanedione product is purified as the free base by stripping oi the pyridine solvent and crystallizing the residue from a suitable solvent or by vacuum distillation thereof.
  • Suitable acid addition salts of the product are prepared by treating an ethanol solution of the free base with an equi-molar amount of the appropriate acid.
  • Examples 8-28.Additional exemplification of compounds of the present invention is given in Table II along with the mode of preparation according to Method A, Method B, or Method C and the appropriate intermediates. Although only a single method of preparation TABLE II-Contlnued Product Ex. No. 11 A Het. Method Intermediates 21 4 (CHz)4- O-C(CH;); B 8-(4-ehlorobutyl)-8-azaspir0I4.5]decane-7,9-dlone and l-[2-(4-tert.-butylpyrimidinympiperazine.
  • azaspiroalkanedione compounds of the present invention are formulated for parenteral administration according to the following example.
  • a sterile solution suitable for intravenous injection is prepared by dissolving 21.9 g. of 8-[4- [4-(2-pyrimidinyl) 1 piperazinyl]butyl] 8 azaspiro[4.5]decane-7,9-dione hydrochloride in 2 liters of water for injection, USP.
  • the solution is adjusted to pH 4.2 with 0.1 N-sodium hydroxide.
  • the solution is sterilized by passage through a bacteriological filter and ml. glass ampules aseptically filled in order to provide 10 mg. of active ingredient per ampule.
  • 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;
  • R and R are independently selected from the group consisting of hydrogen, lower alkyl from 1 to 4 carbon atoms inclusive, and lower alkoxy of from 1 to 4 carbon atoms inclusive;

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US00879604A 1969-11-24 1969-11-24 N-(heteroarcyclic)piperazinylalkyl-azaspiroalkanediones Expired - Lifetime US3717634A (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
BE759371D BE759371A (fr) 1969-11-24 Azaspirodecanediones heterocycliques et procedes pour leur preparation
US00879604A US3717634A (en) 1969-11-24 1969-11-24 N-(heteroarcyclic)piperazinylalkyl-azaspiroalkanediones
ZA707826A ZA707826B (en) 1969-11-24 1970-11-19 Heterocyclic azaspirodecanediones and process for the preparation thereof
FR7041860A FR2073406B1 (xx) 1969-11-24 1970-11-20
DK589670AA DK141753B (da) 1969-11-24 1970-11-20 Analogifremgangsmåde til fremstilling af azaspirodecan- og -undecandionderivater eller syreadditionssalte deraf.
NL7017031A NL7017031A (xx) 1969-11-24 1970-11-20
DE19702057845 DE2057845A1 (de) 1969-11-24 1970-11-24 Heterocyclische Azaspirodecandione und Verfahren zu ihrer Herstellung
GB5590870A GB1332194A (en) 1969-11-24 1970-11-24 Heterocyclic azaspiroalkanediones
CH341874A CH552608A (de) 1969-11-24 1970-11-24 Verfahren zur herstellung von azaspiroalkandion-derivaten.
CY886A CY886A (en) 1969-11-24 1970-11-24 Heterocyclic azaspiroalkanediones
CH1741770A CH552607A (de) 1969-11-24 1970-11-24 Verfahren zur herstellung von azaspiroalkandion-derivaten.
US312543A US3907801A (en) 1969-11-24 1972-12-06 N-{8 (4-pyridyl-piperazino)-alkyl{9 -azaspiroalkanediones
KE2691A KE2691A (en) 1969-11-24 1977-01-14 Heterocyclic azaspiroalkanediones
HK61/77A HK6177A (en) 1969-11-24 1977-01-27 Heterocyclic azaspiroalkanediones
MY151/77A MY7700151A (en) 1969-11-24 1977-12-30 Heterocyclic azaspiroalkane diones
ES530335A ES530335A0 (es) 1969-11-24 1984-03-07 Procedimiento para la obtencion del clorhidrato de 8-4-4-(2-pirimidinil)-1-piperazinil-butil-8-azaspiro 4,5-decano-7,9- diona.

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US00879604A US3717634A (en) 1969-11-24 1969-11-24 N-(heteroarcyclic)piperazinylalkyl-azaspiroalkanediones

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US312543A Division US3907801A (en) 1969-11-24 1972-12-06 N-{8 (4-pyridyl-piperazino)-alkyl{9 -azaspiroalkanediones

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US00879604A Expired - Lifetime US3717634A (en) 1969-11-24 1969-11-24 N-(heteroarcyclic)piperazinylalkyl-azaspiroalkanediones
US312543A Expired - Lifetime US3907801A (en) 1969-11-24 1972-12-06 N-{8 (4-pyridyl-piperazino)-alkyl{9 -azaspiroalkanediones

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US312543A Expired - Lifetime US3907801A (en) 1969-11-24 1972-12-06 N-{8 (4-pyridyl-piperazino)-alkyl{9 -azaspiroalkanediones

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US (2) US3717634A (xx)
BE (1) BE759371A (xx)
CH (2) CH552607A (xx)
CY (1) CY886A (xx)
DE (1) DE2057845A1 (xx)
DK (1) DK141753B (xx)
ES (1) ES530335A0 (xx)
FR (1) FR2073406B1 (xx)
GB (1) GB1332194A (xx)
HK (1) HK6177A (xx)
KE (1) KE2691A (xx)
MY (1) MY7700151A (xx)
NL (1) NL7017031A (xx)
ZA (1) ZA707826B (xx)

Cited By (106)

* Cited by examiner, † Cited by third party
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US3907801A (en) * 1969-11-24 1975-09-23 Mead Johnson & Co N-{8 (4-pyridyl-piperazino)-alkyl{9 -azaspiroalkanediones
US4123538A (en) * 1977-08-30 1978-10-31 Mcneil Laboratories, Incorporated (2-Amino-2-oxoethoxy)acetic acid compounds, compositions and methods
DE2920739A1 (de) * 1978-05-22 1979-12-06 Bristol Myers Co Verwendung von 8-eckige klammer auf 4-eckige klammer auf 4-(2-pyrimidinyl)-1piperazinyl eckige klammer zu -butyl eckige klammer zu -8-azaspiro eckige klammer auf 4.5 eckige klammer zu decan-7,9-dion
US4305944A (en) * 1980-09-08 1981-12-15 Mead Johnson & Company N-[(4-[3-cyano substituted pyridyl]piperazino)alkyl]-azaspirodecanediones
US4320131A (en) * 1981-03-16 1982-03-16 Mead Johnson & Company N-[(4-Phenyl-1,2,3,6-tetrahydropyridin-1-yl)alkylene]azaspiroalkanediones and N-[(4-hydroxy-4-phenylpiperidin-1-yl)alkylene]azaspiroalkanediones
FR2492383A1 (fr) * 1980-10-16 1982-04-23 Bristol Myers Co Halogenures d'ammonium spiro-quaternaire, leur procede de prepatation et leur utilisation dans un procede de production de n-(2-pyrimidinyl) piperazinyl-alkylazospiro-alcanediones
DE3149011A1 (de) * 1980-12-11 1982-07-15 Bristol-Myers Co., 10022 New York, N.Y. Verfahren zur herstellung von buspiron
US4361565A (en) * 1981-12-28 1982-11-30 Mead Johnson & Company 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyridines
US4367335A (en) * 1981-08-03 1983-01-04 Mead Johnson & Company Thiazolidinylalkylene piperazine derivatives
FR2518993A1 (fr) * 1981-12-28 1983-07-01 Bristol Myers Co 2-(4-((4,4-dialkyl-2,6-piperidinedion-1-yl))-1-piperazinyl) pyrimidines, leur preparation et leur application pharmacologique
FR2521561A1 (fr) * 1981-12-23 1983-08-19 Bristol Myers Co Derives de benzisothiazole et benzisoxale piperazine
US4409223A (en) * 1982-08-06 1983-10-11 Riblet Leslie A Anxiolytic method
US4417049A (en) * 1980-10-16 1983-11-22 Mead Johnson & Company Spiro-quaternary ammonium halides and N-(2-pyrimidinyl)piperazinylalkylazaspiroalkanedione process
WO1984000752A1 (en) * 1982-08-11 1984-03-01 Eastman Kodak Co Acid salts of 1-(cyanoalkyl)-4-guanylpiperazines and methods for their preparation and use
US4438119A (en) 1982-12-23 1984-03-20 Mead Johnson & Company Method for alleviation of extrapyramidal motor disorders
US4452799A (en) * 1981-12-23 1984-06-05 Mead Johnson & Company Benzisothiazole and benzisoxazole piperazine derivatives
US4456756A (en) * 1981-08-03 1984-06-26 Mead Johnson & Company Spirothiazolidinyl piperazine derivatives
FR2540499A1 (fr) * 1983-02-07 1984-08-10 Bristol Myers Co Derive de 5-fluoro-pyrimidine-2-yl piperazine antipsychotique
US4507303A (en) * 1981-12-22 1985-03-26 Sumitomo Chemical Company, Limited Succinimide derivatives, compositions and method of use
US4515947A (en) * 1982-08-11 1985-05-07 Eastman Kodak Company Cyanoalkylpiperazines and methods for their preparation and use
FR2555585A1 (fr) * 1983-09-12 1985-05-31 Bristol Myers Co Derives de la 1-heteroaryl-4 ((2,5-pyrrolidinedion-1-yl) alkyl )piperazine, leur procede de preparation et leur application pharmacologique
US4562255A (en) * 1984-03-30 1985-12-31 American Home Products Corporation Substituted bi-alicyclic imides
FR2567886A1 (fr) * 1984-07-23 1986-01-24 Bristol Myers Co Derives 1-(2-pyrimidinyl)-piperazinyliques de 1-pyrrolidine-2-ones et leur application psychogeriatrique
US4581357A (en) * 1983-02-07 1986-04-08 Mead Johnson & Company Antipsychotic 5-fluoro-pyrimidin-2-yl piperazine compound
US4598078A (en) * 1982-10-21 1986-07-01 Sumitomo Chemical Company, Limited N-(substituted piperazinyl) alkylbicyclic succinimide derivatives
US4612312A (en) * 1984-07-30 1986-09-16 Merrell Dow Pharmaceuticals Inc. Glutarimide antianxiety and antihypertensive agents
US4620002A (en) * 1982-08-11 1986-10-28 Eastman Kodak Company 2-pyrimidyl alkanesulfonates
US4619930A (en) * 1985-01-16 1986-10-28 Bristol-Myers Company Antipsychotic cyclic imide derivatives of 2-(4-butylpiperazin-1-yl)pyridines, compositions and use
US4634703A (en) * 1985-10-25 1987-01-06 Bristol-Myers Company Method for alleviation of panic disorders
US4640921A (en) * 1986-02-04 1987-02-03 Bristol-Myers Treatment of sexual dysfunction with buspirone
DE3622842A1 (de) * 1985-07-08 1987-03-05 Bristol Myers Co Diazinylpiperidin-derivate, verfahren zu ihrer herstellung und pharmazeutische mittel
FR2587342A1 (fr) * 1985-06-22 1987-03-20 Sandoz Sa Nouveaux derives du thiazole, leur preparation et leur utilisation en therapeutique
US4668687A (en) * 1984-07-23 1987-05-26 Bristol-Myers Company Psychogeriatric 1-(2-pyrimidinyl)piperazinyl derivatives of 1-pyrrolidin-2-ones
US4677104A (en) * 1985-05-06 1987-06-30 Bristol-Myers Company Antipsychotic fused-ring pyridinylpiperazine derivatives
US4687772A (en) * 1986-10-07 1987-08-18 Bristol-Myers Company Method for improvement of short term memory
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EP0238905A2 (en) * 1986-03-05 1987-09-30 Merrell Dow Pharmaceuticals Inc. 4-(2-pyrimidinyl)-1-piperazinyl heterocyclic carbonyl derivatives
US4745117A (en) * 1985-03-27 1988-05-17 Sumitomo Pharmaceuticals Company, Limited Imide derivatives and compositions for use as antipsychotic agents
US4777173A (en) * 1987-03-25 1988-10-11 Bristol-Myers Company Method for treatment of alcohol abuse
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US4810789A (en) * 1987-08-28 1989-03-07 Bristol-Myers Company Process for buspirone hydrochloride polymorphic crystalline form conversion
US4812567A (en) * 1985-10-16 1989-03-14 American Home Products Corporation Polycyclic spiroimides with psychotropic activity
US4812461A (en) * 1986-09-26 1989-03-14 Sumitomo Pharmaceuticals Company, Limited Imide derivatives and their use in the treatment psychosis
EP0313535A1 (en) * 1987-10-22 1989-04-26 Bristol-Myers Squibb Company Oral formulation of buspirone and salts thereof
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CH552607A (de) 1974-08-15
MY7700151A (en) 1977-12-31
NL7017031A (xx) 1971-05-26
BE759371A (fr) 1971-05-24
KE2691A (en) 1977-03-04
US3907801A (en) 1975-09-23
FR2073406B1 (xx) 1974-10-11
DK141753B (da) 1980-06-09
FR2073406A1 (xx) 1971-10-01
GB1332194A (en) 1973-10-03
ES8505251A3 (es) 1985-05-16
DK141753C (xx) 1980-11-24
CH552608A (de) 1974-08-15
CY886A (en) 1977-03-18
ZA707826B (en) 1971-07-28
DE2057845A1 (de) 1971-06-09
ES530335A0 (es) 1985-05-16
HK6177A (en) 1977-02-04

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