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United States Patent Office Paterated June 29, 1965

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United States Patent Office Paterated June 29, 1965 3,92,225 United States Patent Office Paterated June 29, 1965 2 appear. The morpholino compounds are especially po tent analeptics. Some other compounds of the series are 3,192,221 preferred as hypotensives, particularly those amino com 4-(OMEGA SUBSTITUTED ALKYL)-3,3-EDSUBST pounds wherein the amino group is dialkylamino, espe TUTE D-1-SUBSTITUTED - 2 - PYERROLDENONES cially dimethylamino, piperidino, and pyrrollidino. In AND 4-(OMEGA-SJBSTITUTED ALKYEL)-3,3-DE. 5 SUBSTITUTED. SUBSTITUTEED-2-TESNPYR addition, as will be apparent and become more obvious ROLDENONES AND PRODUCTION THEREGF hereinafter, some compounds, though active in them Carl D. Lunsford, Richmond, and Albert D. Cale, Jr., selves, are also valuable as intermediates in preparing Bon Air, Va., assignors to A. H. Robins Company, ac., other and still more active compounds of Formula X, Richmond, Va., a corporation of Virginia O e.g., the omega-haloalkyl compounds. Those compounds No Drawing. Filed Dec. 4, 1963, Ser. No. 156,945 having a reactive functional group in the side-chain are 29 Caims. (C. 260-295) of course useful, as shown herein, as reactants in stand ard-type reactions characteristic of the functional group contained therein. While the degree and relative degree The present application is a continuation-in-part of our 5 of their activities varies, all compounds tested exhibited prior-filed co-pending application Serial No. 88,036, filed analeptic activity although, as stated, because of the rela February 9, 1961. tive degree of analeptic vs. hypotensive activity, some are The present invention relates to certain heterocyclic or preferred as hypotensives. The amine quaternary am ganic compounds which may be referred to as 4-(omega monium salts tested, in addition to being respiratory substituted alkyl)-2-pyrrollidinones and 4-(omega-sub 20 stimulants, evidence ganglionic blocking activity. stituted alkyl)-2-thionpyrrolidinones and is more particu It is accordingly an object of this invention to provide arly concerned with 4-(omega-substituted alkyl)-3,3- novel and useful 4-(omega-substituted alkyl)-2-pyrroli disubstituted-i-substituted-2-pyrrolidinones and 4-(omega dinones and -2-thion pyrrollidinones, processes for their substituted alkyl)-3,3-disubstituted-1-Substituted - 2 - thion production, intermediate products useful in their prepara pyrrollidinones, processes for the production thereof, 25 tion, and processes for preparing such intermediates which intermediate products useful in the preparation thereof, in themselves have useful pharmacological activity. Other and processes for the preparation of such intermediates. objects of the invention will be apparent to one skilled in The invention is especially concerned with such com the art, and still other objects will become apparent here pounds of the formula: inafter. 30 In the definitions of symbols in foregoing Formula X and where they appear elsewhere throughout this specifi A R. cation, the terms have the following significance. By "monocarbocyclic aryl' radical is meant an aryl R---(CHR), CEIR'CHR'-B' radical of the benzene series, having six ring carbon 35 atoms, and this term includes the unsubstituted phenyl Ea NN/ -R radical and phenyl radicals substituted by any radical or radicals which are not reactive or otherwise interfering k (X) under conditions of the reaction, such as nitro, lower alkoxy, lower-alkylmercapto, lower-alkyl, halo, and the 40 like. The substituted-phenyl radicals have preferably no wherein: A is lower-alkyl, cycloalkyl, monocarbocyclic more than one to three substituents such as those given aryl, or monocarbocyclic aralkyl; R is lower-alkyl, lower above and, furthermore, these substituents can be in alkenyl, cycloalkyl, monocarbocyclic aryl, monocarbo various available positions of the phenyl nucleus and, cyclic araikyl, pyridyl, thienyl, or thenyl; R is lower where more than one substituent is present, can be the aikyl, lower-alkenyl, cycloalkyl, cycloalkenyi, or mono 45 same or different and can be in various position combin carbocyclic aralkyl; R' is hydrogen or methyl, a maxi ations relative to each other. The lower-alkyl, lower mum or one R' being other than hydrogen; n is Zero or alkoxy, and lower-alkylmercapto substituents each have one; B is halogen, hydroxy, mercapto, lower-alkylmer preferably from one to three carbon atoms which can be capto, lower-alkoxy, phenoxy, benzyloxy, benzoyloxy, arranged as straight or branched chains. hydroxybenzoyloxy, nicotinoyloxy, lower-alkanoyloxy, 50 Among the suitable amino radicals included within the cyano, carboxy, carbonyl halide, carb-lower alkoxy, symbol B are primary, secondary, and tertiary amino carbamyl, lower-alkanoyl, -N-(lower-alkanoyl)-amino, radicals, such as unsubstituted amino (-NH2), (lower phthalimido, and amino; and E is oxygen or sulfur. alkyl)-amino; di- (lower-alkyl)-amino; (lower-alkenyl)- The compounds of the invention having the foregoing. amino; di- (lower-alkenyl)-amino; phenylamino; (hy Formula X are generally characterized by important 55 pharmacological activity, indicative of their use in coun droxy-lower-alkyl)-amino; di- (hydroxy - lower - alkyl)- teracting certain physiological abnormalities in an animal amino; basic saturated monocyclic heterocyclic radicals body. The compounds are analeptics, hypotensives, or of less than twelve carbon atoms, as exemplified by both. Certain compounds of the series are extremely piperidino; (lower-alkyl)-piperidino, e.g., 2-, 3-, or potent and long acting analeptics, stimulating respiration 60 4-(lower-alkyl)piperidino; di- (lower - alkyl)-piperidino, and antagonizing central nervous system depression and e.g., 2,4-, 2,6-, or 3,5-di-(lower-alkyl)-piperidino; (lower exhibiting a particularly durable antagonism against alkoxy)-piperidino; pyrrolidino; (lower-alkyl)-pyrrolidino; barbiturate-induced depression or poisoning at dose levels di-(lower-alkyl)-pyrrollidino; (lower-alkoxy)-pyrrolidino; considerably below that at which untoward side effects morpholino; (lower-alkyl)-morpholino; di- (lower-alkyl)- 3,192,221 5 6 CHART I-PREPARATION OF STARTING In the same manner, starting from the appropriate 1 ACETONITRELES (IV) substituted-3-chloropyrrolidine (II) and the selected alpha, alpha-disubstituted-acetonitrile (II), in turn pro NaNE A-CHCN - - A-CEICN duced by reaction of the selected alpha-substituted-aceto RC k nitrile () and the chloride or bromide of the other sub stituent R desired to be introduced into the alpha position, (I) (II) or by introducing the pyrrolidyl substituent (III) before the second alpha substituent, various other alpha-(1-Sub stituted -3-pyrrolidyl)-alpha, alpha-disubstituted-acetoni O triles are prepared. Other compounds within the scope of Formula IV which are prepared according to the man ner of foregoing Preparation 1 are as follows: O-(1-isopropyl-3-pyrrolidyl)-cy-allyl-a-phenylacetonitrile, ox-(1-allyl-3-pyrrolidyl)-ox,c-dicyclohexylacetonitrile, 5 g-(1-phenyl-3-pyrrolidyl)-cy,c-dimethylacetonitrile, ca-(1-isopropyl-3-pyrrollidyl)-ox-benzyl-O-phenylaceto nitrile, cx,c-bis-(1-isopropyl-3-pyrrollidyl)-cy-phenylacetonitrile, cx-(1-isopropyl-3-pyrrolidyl)-O-(2- or 3-thienyl)-cyphenyl (IV) 20 acetonitrile, oz-(1-isopropyl-3-pyrrolidyl)-a-(2- or 3-thenyl)-cy-phenyl The alpha-(1-substituted-3-pyrrolidyl)-alpha, alpha acetonitrile, disubstituted- (e.g., dimethyl or diphenyl) acetonitriles c-(1-isopropyl-3-pyrrollidyl)-ox-(p-methoxyphenyl)-ox (IV) are generally prepared by alkylating the alkali metal, phenylacetonitrile, e.g., sodium, salt of the appropriate alpha, alpha-disub 25 ox-(1-isopropyl-3-pyrrolidyl)-ox-(m-chlorophenyl)-or stituted-acetonitrile (II), e.g., dimethylacetonitrile or di phenylacetonitrile, - phenylacetonitrile, with the appropriate 1-substituted-3- O-(1-isopropyl-3-pyrrolidyl)-a-(o-methylphenyl)-ox halo (e.g., chloro)-pyrrolidine in a suitable solvent such phenylacetonitrile, as dry toluene. The sodium salt of the alpha, alpha-disub a-(1-isopropyl-3-pyrrolidyl)-o-methyl-c-cyclopentyl stituted-acetonitrile (II) is formed by reaction of the nitrile 30 acetonitrile, with sodium amide in the dry solvent, e.g., toluene. The ox-(1-isopropyl-5-methyl-3-pyrrolidyl)-ca,c-diphenyl condensation with the 3-chloro-pyrrollidine (III) is usually acetonitrile, carried out with the application of heat, e.g., in refluxing c-(1-isopropyl-4-methyl-3-pyrrolidyl)-cy,o-diphenyl benzene, toluene, or like solvent, for an extended period, acetonitrie, e.g., approximately three hours. The solvent, e.g., toluene, 35 c-(1-isopropyl-3-methyl-3-pyrrolidyl)-ox,c-diphenyl solution is then washed with water and the product ex acetonitrile, tracted, as with one normal hydrochloric acid. This acid c-(1-isopropyl-2-methyl-3-pyrrolidyl)-ox,c-diphenyl extract may then be basified with sodium hydroxide, ex acetonitrile, tracted with a water-insoluble solvent such as ether or 40 a-(1-imethyl-3-pyrrollidyl)-ciphenyl-O-(2-piperidyl)- chloroform, the solution washed and dried, as over sodium acetonitrile, and sulfate, concentrated, and the residue distilled in vacuo. a-(1-isopropyl-3-pyrrolidyl)ox-phenyl-cy-4-(N-methyl In most cases, the product crystallizes on standing and may piperidyl)-acetonitrile, be recrystallized from an appropriate solvent or solvents. The following preparation illustrates this method in which, respectively prepared as indicated in the foregoing by the if desired, the radical R may alternatively by introduced reaction of into the acetonitrile molecule after the pyrrolidyl radical, rather than before the pyrrolidyl radical, which
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