HETEROCYCLIC ALKYLENE TRIAZINONES

Abstract: Heterocyclic alkyl s-triazine compounds are prepared from the corresponding amidinourea and amidinothiourea compounds by reacting with an activated form of an acid amide to give respectively substituted s-triazinones and thiones of the formula <IMAGE> which have pharmacological properties that render them suitable for use for a variety of medicinal purposes, including use as antidiarrheal agents, and which are also useful derivatives in analyzing for the corresponding amidinourea or amidinothiourea precursors.

Description: HETEROCYCLIC ALKYLENE TRIAZINONES Field of the Invention This invention relates to a method for cyclizing a idinoureas and amidinothioureas and to heterocyclic com- pounds produced by the method. More specifically, this invention relates to heterocyclic al ylene triazinones and triazinthiones. Summarv of the Invention In accordance with the present invention, there is provided a class of compounds comprising 1,4-substituted- 1,2-dihydro-l,3,5-triazine-2-ones and thiones of Formula I. R, ? I wherein: n is 1 to 3; X is oxygen or sulfur; R. is a 5 or 6 membered heterocycle or a substituted 5 or 6 membered heterocycle; R- is hydrogen or lower alkyl; and and R. are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkyl amino, aryl or aryl-lower alkyl, lower alkoxy, phenoxy, a 5 or 6 membered heterocycle or a lower alkyl substituted 5 or 6 membered heterocycle or R_ and R. together with the nitrogen to which they are attached form a 3 to 7 membered heterocyclic ring, selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, azepinyl, piperazinyl, thiamorpholinyl, trimethylenetri- aminyl, ethyleneiminyl, and morpholinyl; and wherein: aryl means phenyl in which one or more of the phenyl hy¬ drogens has been replaced by the sa~e or different sub- stituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkyl acyl- amino, lower alkyl acyloxy, hydroxy, lower alkoxy, phenyl- lower alkoxy, lower alkanoyl, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and 5 or 6 membered heterocycle means a heterocyclic substit- uent selected from the group consisting of pyridyl, pyri - idyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl; and the ncn-toxic pharmaceutically acceptable salts there¬ of. OMPΪ WIPO AL RNATlO Detailed Description of the Invention Depending upon the specific substitution, compounds of Formula I above may be present in enolized or tautomeric forms. Certain of the compounds can also be obtained as hydrates or in different polymorphic forms. The structures used herein to designate novel compounds are intended to include the compound shown along with its alternative or transient states. The nomenclature generally employed to identify the novel triazine derivatives as disclosed here¬ in is based upon the ring structure shown in Formula I with the triazine ring positions numbered counterclockwise beginning with the nitrogen having the R, substitution. Heterocyclic alkylene s-triazinones and s-triazin- thiones of this invention which form a preferred class of novel compounds are those represented by Formula I, where R-, is pyridyl. The preferred pyridyl group is 2-pyridyl or substituted 3- or 4-pyridyls in which one or both py¬ ridyl ring carbons vicinal to the carbon attached to the triazinone ring are substituted by lower alkyl, lower alkoxy, or halo lower alkyl. When R, is substituted 3- or 4-pyridyl, thienyl or furyl, the preferred substituents on the heterocylic ring moiety are lower alkyl, hydroxyl, halo, and lower alkoxy. A preferred group of novel triazir.or.es are cc~pcur.cs OMPI _ of the formula wherein: n is 1 to 3; R 2 is hydrogen or lower alkyl; Ro_- r Rr r A~. and R 0 o are the same or different and are C, to C . alkyl, bromo, chloro, hydrox , acyloxy, lower alkanoyl, or C- to C , alkoxy; and R, and R. are each hydrogen, lower alkyl, hydroxy, lower alkoxy, phenoxy, dilower alkyl amino lower alkyl, lower alkanoyl, lower alkenyl, and lower alkvr.yl; or R 3 and R. together with the nitrogen to which they are ■ 5- attached form a 5 or 6 membered heterocyclic ring which may be pyrrolidinyl, oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, or 0 morpholinyl. A most preferred group of heterocyclic alkylene triazinones are compounds of the formula I-b. w 5 n is 1 to 3; R 3 is hydrogen, hydroxy, lower alkyl, lower alkoxy, or o dilower alkyl amino lower alkyl; and R-. is lower alkyl, hydrogen, hydroxy, halo, halo lower alkyl, cr 5 lower alkoxy. -6- A special embodiment of this invention comprises pyridyl-N-oxides of 1-(2-pyridyl-alkylene) triazinones. As employed above and throughout the disclosure, the following terms, unless otherwise indicated, shall be unde stood to have the following meanings: "alkyl" means a saturated aliphatic hydrocarbon which may be either straight or branched chain preferably having no more than about 20 carbon atoms; lower alkyl being preferred; also included are the cyclo alkyl groups such as cyclo hexyl, cyclo propyl etc., and the cyclo- alkyl alkyl groups such as cyclo propylmethyl and the like. "lower alkyl" means an alkyl group as above, having 1 to 6 carbon atoms, suitable lower alkyl groups are methy ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl and isopentyl. "cycloalkyl" means an aliphatic monocyclic saturated carbocyclic group having 3 to 6 carbcn atoms preferably cyclopropyl, cyclopentyl, and cyclohexyl. "alkenyl" means an unsaturated aliphatic hydrocarbon having no more than about 20 carbon atoms and which con¬ tains one or more double bonds and which may be straight or branched chain with lower alkenyl, i.e. alkenyl of 2 to 6 carbons, being preferred. "lower alkenyl" means alkenyl of 2 to 6 carbon atoms such as ethylene, propylene, butylene, isobutylene, etc. "alkynyl" means an unsaturated aliphatic hydrocarbon 'BUREA T OMPI ^ having no more than about 20 carbon atoms and containing one or more triple bonds with lower alkynyl, i.e. alkynyl of 2 to 6 carbon atoms such as propargyl, butynyl, pentynyl etc. "aryl" means phenyl and substituted phenyl. "substituted phenyl" means a phenyl group in which one or more of the phenyl hydrogens has been replaced by the same or different substituents including halo, lower alkyl, halo lower alkyl, nitro, amino, acylamino, hydroxy, lower alkoxy, aryl-lower alkoxy, acyloxy, cyano, halo- lower alkoxy, or lower alkyl sulfonyl. "aralkyl" means an alkyl (preferably a lower alkyl) in which one or more hydrogens is substituted by an aryl moiety (preferably phenyl or substituted phenyl), e.g. benzyl, phenethyl, etc. "5 and 6 membered heterocyclic group" means a 5 or 6 membered ring having 1 to 3 hetero atoms which may be nitrogen, oxygen or sulfur including pyridyl, (2-pyridyl, 3-pyridyl or 4-pyridyl) , pyrazolyi, iπiidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl, morpholinyl. "substituted 5 or 6 membered heterocycle" means a heterocycle in which one or more of the hydrogens on the ring carbons have been replaced by substituents as given above with respect to substituted phenyl. The terms "halo" and "halcger." include all four halogens, r-arr.ely, fluorine, chlorine, bromine and iodine. The halo alkyls, halophenyl and halosubstitutea pyridyl include groups having more than one halo substituent which may be the same or different such as trifluoromethyl, l-chloro-2-bromo ethyl, chlorophenyl, 4-chloropyridyl, etc. The term "acyloxy" is intended to mean an organic acid radical such as acetoxy, propionoxy, and the like. The term "lower alkanoyl" is intended to include the acid radical of a lower alkanoic acid such as acetyl, propionyl, and the like. The novel compounds of this invention may be syn¬ thesized according to the novel cyclizing reaction as illustrated schematically below: \ - wherein X is sulfur or oxygen indicating that the reaction can employ as starting material either an amidinourea or amidinothiourea. The dangling bonds may be substituted by an appropriate substituent determined by available amidinourea or amidinothiourea starting material. The dangling bonds on the end product l,3,5-triazin-2-one or 1,3,- 5-triazine-2-thione, will be substituted by groups corresponding to similar substituents on the starting materials. It has been found that an amidinourea can be cyclized to the corresponding s-^triazinone by condensing the amid- ■ inourea with an organic reagent having an activated methyl¬ idene group or capable of forming an activated methylidene, for example, a methylidene group having at least one available hydrogen atom and a leaving group such as a di- substituted amino group attached to the methylidene carbon. The organic reagent used for condensing the amidinourea starting material to form the corresponding s-triazinone may be an activated form of an acid amide, an ortho ester or acyl derivative, such as, a Vi ' lsmeir reagent which will bring about acylation and ring closure of the amidino¬ urea or thiourea to give s-triazinones of Formula I above. The cyclizing process can be used in the same manner to prepare s-triazinthiones from the corresponding amidino- thioureas and it will be understood that in referring to the preparation of triaziones it is intended' to include also the thiones. The reagent may be the dialkylacetal of a di-alkyl-lower carboxylic acid amide or the reaction product of a di-alkyl-lower carboxylic acid amide and an alkylating agent. The reagent can be prepared in situ or in advance depending upon its stability. The synthesis of triazinones according to this invention can employ as starting material known amidinoureas or similar starting materials also known in the art, or the materials employed as precursors for cyclizing to form s-triazinones can be readily prepared by analogy to the preparation of the known starting materials. Suitable amidinourea starting mat¬ erials are those disclosed in ccpending U.S. Patent Ap- plication Serial No. 262,808, the disclosure of which are incorporated herein by reference. Thus, the novel cycliz¬ ing process of this invention can be used to derivatize amidinoureas and thioureas of Formula II below. g FREA (T OMPI _ -10- X NH V R. - (CH, ) - NH - C NH II 1 n - 'N. \ © © R. R, - (CH- ) - NH - Il-a x n - 0 > wherein n is 1 to 3 and X, R 1. , R3_ and R4. have the same meanings as above. 5 It should be understood that whereas the structure of the starting materials are shown here in a particular configuration for the purposes of illustration, it is in¬ tended to include the various structural isomers as previously noted. By way of illustration, an alternative 10 structure is shown by Formula Il-a. Where reference is made to the terminal nitrogens, it is intended to denote the urea nitrogen designated as position 1 in Formula II and the unsubstituted amidino nitrogen. The l,3,5-triazin-2-ones and l,3,5-triazin a -2-thiones 15 may be prepared according to this invention utilizing as starting materials any of the prior art amidinoureas or amidinothioureas including the 1-pyridylalkylene amidino¬ ureas and thioureas of Formula IV below which constitute a preferred group of starting materials. -fϋREAC OMPI wherein: n is 1 to 3; and X and the R-, through R R substituents have the same meanings as the corresponding substituents on the novel triazines of Formula I-a described herein¬ above. Amidinourea starting materials which can be used to prepare a preferred group of triazine derivatives are those wherein R-. and R. are hydrogen, hydroxy, lower alkyl, lower alkoxy, halo lower alkyl, or aralkyl, or R- " and R. together may form with the nitrogen to which they are attached a 5 to 7 atom ring which may include 0 to 2 hetero atoms of N, O or S. An even more preferred group of starting materials include those where: R Z c Z>, R r O , ?._ J and R o 0 are hvdroσen, halo , lower alkyl . -BU E U OMPI -12- halo lower alkyl, nitro, hydroxy or lower alkoxy. 5 A special embodiment of this invention comprises compounds prepared from starting materials according to Formula IV wherei : n is 1 or 2; X is oxygen; _0 Rj. and R g are the same or different and are hydrogen, lower alkyl, lower alkoxy, or halo; and one of R, and R. is hydrogen and the other is lower alkyl, halo lower alkyl, τ_5 hydroxy, lower alkoxy or acyl. . Using the general method for cyclizing amidinoureas described above, and employing, by way of illustration, 2o as the starting material any of the amidinoureas in Tables I and I-a below, there can be obtained the cor¬ responding triazinones. Tables II, Il-a and V " set forth examples of triazinones within the scope of the " present invention. 25 The thione analogs and their salts are prepared in th same manner using the corresponding amidinothiourea as starting material. Examples of amidinothiourea starting materials are given in Table III. Examples of triazine thiones within the scope of the present invention are 30 set forth in Tables IV and V. "BlJ El? OMPI «- TABLE -I 1- (2'-pyridylmethyl)-3-methylamidinourea 1-(2'-pyridylmethyl)-3-methylamidinourea 1-(2'-pyridylmethyl) 3-propylamidinourea 1-(2'-pyridylmetnyl)-3-i-propylamidinourea 1-(2'-pyridylmethyl)-3-butylamidinourea 1- (2'-pyridylmethyl)-3-i-butylamidinourea 1- (2*-pyridylmethyl)-3-pentylamidinourea 1-(2'-pyridylmethyl)-3-propargylamidinourea 1~ (2'-pyridylmethyl)-3-allylamidinourea 1-(2'-pyridylmethyl)-3-methoxyethylamidinourea 1-(2'-pyridylmethyl)-3-benzyloxyethylamidinourea 1-(2'-pyridylmethyl)-3-phenethoxyethylamidinourea 1- (2'-pyridylmethyl)-3- (N,N-dimethylamidino)urea 1- (2'-pyridylmethyl)-3- (N,N-diethylamidino)urea 1-(2'-pyridylmethyl)-3- (N,N-tetramethyleneamidino) rea 1-(2'-pyridylmethyl)-3- (N,N-pentamethyleneamidino)urea 1-(2'-pyridylmethyl)-3- (N,N-hexamethyleneamidino)urea 1- (3'-methyl-2'pyridylmethyl)-3-methylamidinourea 1- (3'-methyl-2'-pyridylmethyl)-3-ethylamidinourea 1-(3'-methyl-2 '-pyridylmethyl)-3-propylamidinourea 1- (3'-methyl-2'-pyridylmethyl)-3-i-propylamidinoμrea 1- (3'-methyl-2'-pyridylmethyl) 3-i-butylamidinourea 1- (3'-methyl-2*-pyridylmethyl)-3-pentylamidinourea 1- (3'-methyl-2 1 -pyridylmethyl)-3-allylamidinourea 1- (3'-methyl-2'-pyridylmethyl)-3-propargylamidinourea 1-(3'-methyl-2'-pyridylmethyl)-3-cyclopropylamidinourea 1-(3'-methyl-2*-pyridylmethyl)-3-methoxyethylamidinourea 1- (3'-methyl-2'-pyridylmethyl)-3-benzyloxyethylamidinourea 1- (3 '-methyl-2'-pyridylmethyl)-3-phenethoxyethylamidinourea 1- (3 '-methyl-2 '-pyridylmethyl)-3-benzylamidinourea 1- (3' ■ -methyl-2'-pyridylmethyl)-3- (N,N-dimetnylamidino)urea 1- (3'-methyl-2'-pyridylmethyl)-3- (N,N-diethylamidino)urea lilS ΕAtr OMPI 1-(3'-methyl-2'-pyridylmethyl)-3-(N,N-tetramethyleneamidino) urea 1- (3'-methyl-2'-pyridylmethyl)-3-(N,N-pentamethyleneamidino) urea 1-(3'-chloro-2*-pyridylmethyl)-3-methylamidinourea 1-(3'-chloro-2'-pyridylmethyl-3-ethylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-propylamidinourea 1-(3'-chloro-2*-pyridylmethyl)-3-i-propylamidinourea 1-(3*-chloro-2'-pyridylmethyl)-3-butylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-i-butylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-t-butylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-pentylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-allylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-propargylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-cyclopropylamidinourea 1- (3'-chloro-2*-pyridylmethyl)-3-cyclobutylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3- (N-[3'-cyclopentenylj- amidino)urea 1-(3'-chloro-2'-pyridylmethyl)-3-cyclopropylmethylamidino- urea 1-(3'-chloro-2'-pyridylmethyl)-3-methoxyethylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-benzyloxyethylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-phenethoxyethylamidinourea 1-(3'-chloro-2'-pyridylmethyl)-3-benzylamidinourea I-(3'-chloro-2*-pyridylmethyl)-3-(N,N-dimethylamidino)urea 1-(3'-chloro-2'-pyridylmethyl)-3- (N,N-diethylamidino)urea 1-(3'-chloro-2'-pyridylmethyl)-3-(N,N-tetramethyleneamid- ino)urea 1-(2'-pyridylmethyl)-3- (N,NI3'-raethyl-3'-azapentaraethyl- ene]amidino)urea 1-(2'-pyridylmethyl)-3-(N, 13*-oxapenta ethylenelamidino)- urea 1- (3'-pyridylmethyl)-3-methylamidinourea 'BUREACT OMPI Z~° 1-(3'-pyridylmethyl)-3-ethylamidinourea 1-(3'-pyridylmethyl)-3-propylamidinourea 1- (3'-pyridylmethyl)-3-i-propylamidinourea 1-(3'-pyridylmethyl)-3-butylamidinourea 1-(3'-pyridylmethyl)-3-i-butylamidinourea 1-(3'-pyridylmethyl)-3-t-butylamidinourea 1-(3'-pyridylmethyl)-3-pentylamidinourea 1-(3'-pyridylmethyl)-3-allylamidinourea 1-(3'-pyridylmethyl)-3-propargylamidinourea 1-(3'-pyridylmethyl)-3-cyclobutylamidinourea 1- (3'-pyridylmethyl)-3-cyclohexylamidinourea 1- (3'-pyridylmethyl)-3~benzylamidinourea 1- (3'-pyridylmethyl)-3-ιtιethoxyethylamidinourea 1- (3'-pyridylmethyl)-3-^benzyloxy thylamidinourea 1-(3 '-pyridylmethyl)-3-phenethoxyethylamidinourea 1- (3'-pyridylmethyl)-3- (N,N-dimethylamidino)urea 1-(3'-pyridylmethyl)-3- (N,N-diethylamidino) rea 1- (3'-pyridylmethyl)-3->(N,N-pentamethyleneamidino)urea 1-(4'-pyridylmethyl)-3-methylamidinourea 1- (4'-pyridylmethyl)-3-ethylamidinourea 1- (4'-pyridylmethyl)-3-propylamidinourea 1- (4'-pyridylmethyl)-3-i-propylamidinourea 1-(4'-pyridylmethyl)-3-butylamidinourea 1- (4'-pyridylmethyl)-3-t-butylamidinourea 1-(4'-pyridylmethyl)-3-pentylamidinourea 1-(4'-pyridylmethyl)-3-hexylamidinourea 1-(4'-pyridylmethyl)-3-propargylamidinourea 1-(4'-pyridylmethyl)-3-allylamidinourea 1- (4'-pyridylmethyl)-3-methoxyethylamidinourea 1- (4'-pyridylmethyl)-3-benzyloxyethylamidinourea 1- (4'-pyridylmethyl)-3-phenethoxyethylamiάinourea l--(4 '-pyridylmethyl)-3- (N,N-dimethyla-r.idiro)urea 1-^(4'-pyridylmethyl)-3- (N,N-diethylamidino)urea 1- (4 '-pyridylmethyl)-3- (N-methyl-N-ethylamidino)urea 1- 4 '-pyridylmethyl)-3- (N,N-tetramethyleneamidino)urea 1- 4 '—pyridylmethyl)-3- (N,N-pentamethyleneamidino)urea 1- 4 '-pyridylmethyl)-3- (N,N-hexamethyleneamidino)urea 1- 2'-ethyl-4 '-pyridylmethyl)-3-methylamidinourea 1- 2*-ethyl-4'-pyridylmethyl)-3-ethylamidinourea 1- 2'-ethyl-4 '-pyridylmethyl)-3-propylamidinourea 1- 2 '-ethyl-4 '-pyridylmethyl)-3-butylamidinourea 1- 2'-ethyl-4 '-pyridylmethyl)-3-i-butylamidinourea 1- 2 '-ethyl-4'-pyridylmethyl)-3-pentylamidinourea 1- 2'-ethyl-4'-pyridylmethyl)-3-a±lylamidinourea 1- 2'-ethyl-4 '-pyridylmethyl)-3-propargylamidinourea 1- 2 '-ethyl-4 '-pyridylmethyl)-3-methoxyethylamidinourea 1- 2'-ethyl-4 '-pyridylmethyl) -3-benzyloxyethylamidinourea 1- 2'-ethyl-4*-pyridylmethyl)-3- (N,N-dimethylamidino) rea 1- 2'-ethyl-4'-pyridylmethyl)-3-(N,N-diethylamidino)urea 1- 2'-ethyl-4 '-pyridylmethyl)-3- (N,N-tetramethylene- amidino)urea 1- 2' , 6'-dichloro-4 '-pyridylmethyl)-3-methylamidinourea 1- 2 ' , 6 '-dimethyl-. -4 '-pyridylmethyl)-3-methylamidinourea 1- 2'-methyl,6'-chloro-4 *-pyridylmethyl)-3-methylaraidino- urea 1- 2'-thiophenylmethyl)-3-methylamidinourea 1- 3'-thiophenylmethyl) -3-methylamidinourea 1- 5'-methyl-2 *-thiophenylmethyl)-3-methylamidinourea 1- 5'-chloro-2'-thiophenylmethyl)-3-methylamidinourea 1- 2'-pyridylmethyl-N-oxide)-3- (N,N-dimethylamidino)urea 1- 3'-cyano-2'-pyridylmethyl)-3- (N-methylamidino) rea 1- 3 '-carbomethoxy-2'-pyridylmethyl-3- (N-methylamidino)urea 1- 3'-carboethoxy-2'-pyridylmethyl)-3-(N-methylamidino)urea 1- 6 -chloro-2 '-pyridylmethyl)-3- (N-methylamidino)urea 1 - I (Z -methyl-2 '-pyridylmethyl " , -3- (2ϊ-methyiamidino}urea 1- (3 '-ethyl-2'-pyridylmethyl) -3- (N-methylamidino)urea 1-(2'-methyl-3'-pyridylmethyl)-3- (N-methylamidino)urea 1-(2'•-ethyl-3'-pyridylmethyl)-3-(N-methylamidino)urea 1-(2' ,6'-dimethyl-3'-pyridylmethyl)-3-(N-methylamidino) rea 1- (3'-cyano-2'-thiophenylmethyl)-3- (N-methylamidino) rea 1-(3'-carbomethoxy-2'-thiophenylmethyl)3- (N-methylamid¬ ino(urea 1-(3'-carboethoxy-2'-thiophenylmethyl)-3-(N-methylamidino)- urea 1- (2'-methoxy-3'-pyridylmethyl)-3- (N-methylamidino)urea 1-(2'-ethoxy-3'-pyridylmethyl)-3-(N-methylamidino) rea 1-(2'-chloro-3'-pyridylmethyl)-3- (methyla idino)urea 1-furfuryl-3-amidinourea 1-(3'-methyl-furfuryl)-3-amidinourea 1-furfuryl-3- (N-ethylamidino)urea 1-furfuryl-3- (N-propylamidino)urea l-furfuryl-3- (N-i-propylamidino)urea l-furfuryl-3- (N-butylamidino)urea l-furfuryl-3-(N-i-butylamidino)urea l-furfuryl-3- (N-sec-butylamidino)urea 1-furfury1-3- (N-t-butylamidino)urea l-furfuryl-3- (N-pentylamidino)urea 1-furfuryl-3- (N-hexylamiάino)urea 1-furfuryl-3-(N-heptylamidino)urea 1-furfury1-3- (N-cyclopropylamidino) rea l-furfuryl-3- (N-cyclobutylamidino)urea 1-(2'-pyridylmethyl-N-oxide)-3-methylamidinourea 1-(3'-pyridylmethyl-N-oxide)-3-methylamidinourea 1- (4'-pyridylmethyl-N-oxide)-3-methylamidinourea l-furfuryl-3-methylamidinourea l-tetrahydrofurfuryl-3-ιr.ethylamidinourea 1- (1'-irr.idazolylmethyl)-3-r.ethylamidinourea 1- (2'-imidazolylmethyl)-3-methylamidinourea -18- 1-(4'-imidazolylmethyl)-3-methylamidinourea 1-(2'-oxazolylmethyl)-3-methylamidinourea 1- (4'-oxazolylmethyl)-3-meth lamidinourea 1-(5'-oxazolylmethyl)-3-methylamidinourea 1-(2'-thiazolylmethyl)-3-me hylamidinourea 1-(4'-thiazolylmethyl)-3-meth lamidinourea 1-(5'-thiazolylmethyl)-3-methylamidinourea 1-(1'-pyrazolylmethyl)-3-methylamidinourea 1-(1'-[3'-pyrrolidinyl]methl)-3-methylamidinourea 1-(2'-pyrrolidinylmethyl)-3-me hylamidinourea 1-(4'-morpholinylmethyl)-3-methylamidinourea 1-(2'-morpholinylmethyl)-3-πethylamidinourea 1-(2'-pyrimidinylmethyl)-3- ethylamidinourea 1-(4'-pyrimidinylmethyl)-3-methylamidinourea 1-(2'-quinolylmethyl)-3-methylamidinourea 1- (4'-quinolylmethyl)-3-methylamidinourea 1-(1'-isoquinolylmethyl)-3-methylamidinourea 1-furfuryl-3-(N-cyclopentylamidino)urea 1-furfuryl-3- (N-cyclohexylamidino)urea 1-furfuryl-3- (N-phenylamidino)urea 1-furfuryl-3-(N-benzylamidino)urea 1-furfuryl-3-(N-phenethylamidino)urea 1-furfuryl-3-(N-methyl-N-benzylamidino)urea 1-furfuryl-3-(N,N-dibenzylamidino)urea l-tetrahydrofurfuryl-3-amidinourea 1-(3'-methyl-tetrahydrofurf ryl)-3-amidinourea 1-(2'-methyl-tetrahydrofurf ryl)-3-amidinourea 1-(1'-imidazolylmethyl)-3-a— dinourea 1-(2'-methyl-1'-imidazolylmethyl)-3-amidinourea 1-(4'-imidazolylmethyl)-3-a~.idinourea 1-(1'-methyl-4'-imidazolyl—e hyl)-3-a-r.idinourea 1-(2'-methyl-4'-imidazolylmethyl)-3-a idinourea 1-(2'-imidazolylmethyl)-3-a-_idinourea " BURE U OMPI k ?NATIC 1-(2'-oxazolylmethyl)-3-amidinourea 1- ■ (4'-methyl-2'-oxazolylmethyl)-3-amidinourea 1- ■ (4'-oxazolylmethyl)-3-amidinourea 1- ■ (4'-methyl-2'-oxazolylmethyl)-3-amidinourea 1- •(4'-oxazolylmethyl)-3-amidinourea 1- • (2'-methyl-4 '-oxazolylmethyl)-3-amidinourea 1- ■ (5'-oxazolylmethyl)-3-amidinourea 1- •(2'-methyl-5'-oxazolylmethyl)-3-amidinourea 1- (4'-thiazolylmethyl)-3-amidinourea 1- (5'-methyl-4'-thiazolylmethyl)-3-amidinourea 1- (5'-thiazolylmethyl)-3-amidinourea 1- (4'-methyl-5 1 -thiazolylmethyl)-3-amidinourea 1- (1'-pyrazolylmethyl)-3-amidinourea 1-(3'-pyrrolylmethyl)-3-amidinourea 1-(2'-methyl-3'-pyrrolylmethyl)-3-amidinourea 1-(3'-methyl-2'-pyrrolylmethyl)-3-amidinourea 1-(1'-pyrrolodinylmethyl)-3-amidinourea 1- (2'-methyl-1'-pyrrolidmylmethyl)-3-amidinourea 1-(1'-methyl-2'-pyrrolidmylmethyl)-3-amidinourea 1- (4'-morpholinylmethyl)-3-amidinourea 1-(2'-methyl-4 '-morpholinylmethyl)-3-amidinourea 1-(2'-morpholinylmethyl)-3-amidinourea 1- (4'-methyl-2'-morpholinylmethyl)-3-amidinourea 1-(3'-methyl-2'-morpholinylmethyl)-3-amidinourea 1- (3'-morpholinylmethyl)-3-amidinourea 1-(4'-methyl-3'-morpholinylmethyl)-3-amidinourea 1-(2'-methyl-3'-morpholinylmethyl)-3-amidinourea 1- (2'-pyrimidinylmethyl)-3-amidinourea 1-(4'-methyl-2'-pyrimidinylmethyl)-3-amidinourea 1- (4'-pyrimidinylmethyl)-3-amidinourea 1- (2'-methvl- 4 '-pyrimidinylmethyl)-3-amidinourea 1- (3'-quinolylmethyl)-3-aιr.iαinourea 1- (3'-methyl-2'-quinolylmethyl)-3-amidinourea 1- (.4'-quinolylmethyl)-3-amidinourea 1- (3'-methyl-4'-quinolylmethyl)-3-amidinourea 1- (l'-isoquinolylmethyl)-3-amidinourea 1-12- -pyridyl)ethylj-3-methylamidinourea 1-12- -pyridyl)ethylj-3-ethylamidinourea 1-12- -pyridyl)ethyl -3-propylamidinourea 1-12- -pyridyl)ethylj-3-i-propylamidinourea 1-12- -pyridyl)ethyl -3-butylamidinourea 1-12- -pyridyl)ethylj-3-i-butylamidinourea 1-12- -pyridyl)ethyl -3-pentylamidinourea l-{2- -pyridyl)ethylj-3-propargylamidinourea l-[2- -pyridyl)ethylj-3-allylamidinourea l-[2- -pyridyl)ethylj-3-methoxyethylamidinourea l-{2- -pyridyl)ethylj-3--benzyloxyethylamidinourea l-[2- -pyridyl)ethylj-3-phenethoxyethylamidinourea l-[2- -pyridyl)ethylj-3- (N,N-dime hylamidino)urea 1-E2- -pyridyl)ethylj-3^-(N,N-diethylamidino) rea l-[2- -pyridyl)ethyl]-3-(N,N-tetramethyleneamidino)urea 1-12- -pyridyl)ethylj-3-(N,N-pentamethyleneamidino)urea 1-12- -pyridyl)ethylj-3-(N,N-hexamethyleneamidino)urea 1-12- -methyl-2 ' -pyridyl) ethyl] -3-methy lamidinourea 1-12- -methyl-2 1 -pyridyl) ethyl] -3 -ethy lamidinourea l-[2- -methyl-2 ' -pyridyl) ethyl] -3-propylamidinourea l-[2- -methyl- 2 ' -pyridyl) ethyl] -3-i-propylamidinourea 1-12- -methyl-2 ' -pyridyl) ethyl] -3-i-butylamidinourea 1-12- -methyl-2. ' -pyridyl) ethyl] - 3 -penty lamidinourea l-[2- -methyl-2 ' -pyridyl) thyl] -3-allylamidinourea 1-12- -methyl-2 ' -pyridyl) ethyl] -3-propargylanidinourea 1-12- -methyl-2 ' -pyridyl) ethyl] -3-cyclopropylaminourea l-[2- -methyl-2 ' -pyridyl) ethyl] -3-methoxyethylamidinourea 1-12- -methyl-2 ' -pyridyl) ethylj -3-benzyloxyethylaτnidinourea 1-12- -methyl-2 ' -pyridyl) ethylj -3-phenethoxyethyjamiάι-noure 1-12- -methyl-2 ' -pyridyl ) ethyl] -3-benzylamidinourea 1-12- — methvl— 2 ' -pyridyl ) ethyl] -3- (.r ,N-dimet yi miά r-θ) rea 1-12- ' -pyridyl) ethyl] -3- C-^ ,N-dietϊrr 3amidxno) urea 1-I2- (3'-methyl-2'-pyridyl)ethylj-3-( ,N-tetramethylene- amidino)urea l-[2- (3'-methyl-2'-pyridyl)ethyl]-3-(N,N-pentamethylene- amidino)urea 1-12- (3'-chloro-2'-pyridyl)ethylj-3-methylamidinourea 1-12- (3'-chloro-2'-pyridyl)ethylj-3-ethylamidinourea 1-12- (3'-chloro-2*-pyridyl)ethylj-3-propylamidinourea l-{2- (3'-chloro-2'-pyridyl)ethylj-3-i-propylanidinourea l-[2-(3'-chloro-2'-pyridyl)ethylj-3-butylamidinourea l-[2- (3'-chloro-2'-pyridyl)ethyl -3-i-butylamidinourea l-[2- (3'-chloro-2'-pyridyl)ethylj-3-t-butylamidinourea 1-12- (3'-chloro-2'-pyridyl)ethyl -3-pentylamidinourea 1-12-(3'-chloro-2'-pyridyl)ethyl -3-allylamidinourea l-[2- (3'-chloro-2'-pyridyl)ethyl J-3-propargylamidinourea l-[2- (3'-chloro-2'-pyridyl)ethyl]-3-cyclopropylamidinourea l-{2- (3'-chloro-2'-pyridyl)ethyl -3-cyclobutylamidinourea 1-12- (3'-chloro-2'-pyridyl)ethylj-3- (N-13'-cyclopentenyl]- amidino)urea l-[2-(3'-chloro-2'-pyridyl)ethyl]-3-cyclopropyImethylamid- inourea 1-12- (3'-chloro-2'-pyridyl)ethylj-3-methox eth lamidinourea 1-12- (3 '-chloro-2'-pyridyl)ethyI]-3-benzyloxyethylamidino- urea 1-12-(3'-chloro-2'-pyridyl)ethyl]-3- (N, -dimethy amidino)- urea l-[2-(3'-chloro-2'-pyridyl)ethylτ-3-(N,N-diethylamidino)- urea 1-{2- (3'-chloro-2'-pyridyl)ethyl]-3- (N,N-tetramethylene- amidino)urea 1-12- (2'-pyridyl)ethylj-3- (N,NI3'-methyl-3'-azapenta ethy- lenejamidino) rea 1-12- (2 '-pyridyl) ethyl]-3- (N,NI3 '-cxazentarr.et ylene]ami¬ dino)urea 1-12- (2'-pyridyl)ethylj-3-methylamidinourea —pyridyl -3-eth lamidinourea -pyridyl -3-propylamidinourea -pyridyl !-3-i-prop lamidinourea -pyridyl -3-butylamidinourea -pyridyl -3-i-butylamidinourea -pyridyl I-3-t-butylamidinourea -pyridyl -3-pentylamidinourea -pyridyl -3-allylamidinourea -pyridyl -3-propargylamidinourea -pyridyl [-3-cyclobutylamidinourea -pyridyl -3-cyclohexylamidinourea -pyridyl -3-benzylamidinourea -pyridyl -3-methoxyethylamidinourea -pyridyl -3-benzyloxyethylamidinourea -pyridyl -3-phenethoxyethylamidxnourea pyridyl -3- (N,N-dimethylamidino)urea pyridyl I-3-(N,N-pentamethyleneamidino)urea pyridyl i-3-methylamidinourea pyridyl -3-ethylamidinourea -pyridyl -3-propylamidinourea pyridyl I-3-i-propylamidinourea pyridyl -3-butylamidinourea pyridyl -3-t-butylamidinourea pyridyl ! -3-pentylamidinourea pyridyl -3-hexylamidinourea pyridyl !-3-propargylamidinourea pyridyl !-3-allylamidinourea pyridyl I—3-methoxyethylamidinourea -pyridyl -3-benzyloxyethylamidinourea pyridyl -3-phenethoxyethylamidinourea -pyridyl ethyl]-3- ( , -di e hylamidino)urea -pyridyl ethyl]-3- (N,N-diethylamidino)urea -pyridyl ethylj-3- (N-methyl-N-ethylamidino)urea OMPI WIPO _ 1-[3-(2'-pyridyl) ropyl]-3-methylamidinourea 1-13-(2'-pyridyl)propylJ-3-ethylamidinourea 1-13- (2'-pyridyl)propyl]-3-propylamidinourea 1-13- (2'-pyridyl)propylj-3-i-propylamidinourea 1-13-(2'-pyridyl)propyl -3-butylamidinourea 1-13- (2'-pyridyl)propyl]-3-i-butylamidinourea l-{3-(2 • -pyridyl)propyl -3-pentylamidinourea 1-[3-(2*-pyridyl)propyl]-3-propargylamidinourea l-[3- (2'-pyridyl)propylj-3-allylamidinourea l-[3- (2'-pyridyl)propylj-3-methoxyethylamidinourea 1-[3- (2'-pyridyl)propyl]-3-benzyloxyethylamidinourea 1-13-(2'-pyridyl)propyl -3-phenethoxyethylamidinourea 1-[3- (2'-pyridyl)propylj-3-(N,N-dimethylamidino)urea 1-[3-(2'-pyridyl)propyl -3-(N,N-diethylamidino)urea l-[3-(2*-pyridyl)propyl -3-(N,N-tetramethyleneamidino)urea l-[3-(2'-pyridyl)propylj-3- (N,N-pentamethyleneamidino)urea 1-13- (2'-pyridyl)propyl]-3-(N,N-hexamethyleneamidino)urea 1-13- (3'-methyl-2'-pyridyl)propylj-3-methylamidinourea 1-13-(3 '-methyl-2'-pyridyl)propylj-3-ethylamidinourea 1-13- (3'-methyl-2'-pyridyl)propyl]-3-propylamidinourea 1-[3- (3'-methyl-2'-pyridyl)propyl]-3-i-propylamidinourea 1-13- (3'-methyl-2'-pyridyl)propyl]-3-i-butylamidinourea 1-13- (3'-methyl-2'-pyridyl)propyl]-3-pentylamidinourea 1-13-(3'-methyl-2'-pyridyl)propyl]-3-allylamidinourea 1-13- (3'-methyl-2'-pyridyl)propyl]-3-propargylamidinourea 1-13- (3'-methyl-2'-pyridyl)propyl]-3-cyclopropylamidinourea 1-13-(3'-methyl-2'-pyridyl)propyl]-3-methoxyethylamidinourea 1-[3- (3'-methyl-2'-pyridyl)propyl]-3-benzyloxyethylamidino¬ urea 1-13- (3'-methyl-2'-pyridyl)propyl]-3-phenethoxyethylamid- inourea 1-13- (3'-methyl-2'-pyridyl)propyl]-3-benzylamidinourea 1- (3- (3'-methyl-2'-pyridyl)propylj-3- (N, -dimethylamidino) urea 1- 13- ( 3 * -methyl- 2 -pyridyl)propylj-3-(N,N-diethy amidino)- urea 1- 13- (3 » -methyl-2 -pyridyl) ropyl -3-(N,N-tetramethylene- amidino)urea 1-13-(3'-methyl-2 -pyridyl) ropyl -3-(N,N-pentamethylene- amidino) rea l-[3-(3*-chloro-2 -pyridyl) ropylj-3-methylamidinourea l-[3-(3*-chloro-2 -pyridyl)propyl -3-ethylamidinourea 1-13-(3'-chloro-2 -pyridyl)propyl -3-propylamidinourea l-[3-(3'-chloro-2 -pyridyl)propyl]-3-i-propylamidinourea l-[3-(3'-chloro-2 -pyridyl) ropylj-3-butylamidinourea l-[3-(3'-chloro-2 -pyridyl)propylj-3-i-butylamidinourea l-[3-(3 « -chloro-2 -pyridyl)propylj-3-t-butylamidinourea l-[3-(3'-chloro-2 -pyridyl)propylj-3-pentylamidinourea 1-[3-(3'-chloro-2 —pyridyl)propyl -3—allylamidinourea l-£3-(3'-chloro-2 -pyridyl) ropyl]-3-propargylamidinourea l-[3-(3*-chloro-2 -pyridyl)propyl -3-cyclopropylamidinoure 1-13-(3*-chloro-2 -pyridyl)propylj-3-cyσlobutylamidinourea l-[3-(3'-chloro-2 -pyridyl)propylj-3- (N-[3'cyclopentenyl]- amidino)urea l-[3-(3'-chloro-2 -pyridyl)propyl]-3-cyclopropylmethyl- amidinourea l-[3-(3'-chloro-2 -pyridyl)propylJ-3-methoxyethylamidino- urea l-I3-(3'-chloro-2 -pyridyl)propylj-3-benzyloxye ~ thylamidino urea l-[3-(3'-chloro-2 -pyridyl)propylj-3-phenethoxyethylamid- inourea l-[3-(3'-chloro-2 -pyridyl)propyl -3-benzylamidinourea 1-[3- (3'-chloro-2 -pyridyl)propyl -3- (N, -dimethylamidino) urea 1-13- (3'-chloro-2 -pyridyl)propylj-3-{N, -dieth lamidino)- urea l-I3-(3'-chloro-2 -pyridyl)propylj-3τN,N-tetramethylene- amidino)urea l- [3- (2 ' -pyridyl) propylj -3- (N,Nβ ''-methyl-3 ' -azapenta- methylenejamidino) rea 1-13-(2'-pyridyl)propyl -3-(N,NI3'-oxapentamethylene - amidino)urea l-[3- (2'-pyridyl)propylj-3-methylamidinourea l-[3- (2'-pyridyl) ropyl]-3-ethylamidinourea l-[3-(2'-pyridyl)propylj-3-propylamidinourea 1-[3- (2*-pyridyl)propyl -3-i-propylamidinourea l-[3-(2'-pyridyl)propyl]-3-butylamidinourea l-[3-(2'-pyridyl)propylj-3-i-butylamidinourea l-[3- (3'-pyridyl)propylj-3-t-butylamidinourea 1-[3-(3'-pyridyl)propyl -3-pentylamidinourea l-[3- (3'-pyridyl)propyl -3-allylamidinourea l-[3-(3'-pyridyl)propyl -3-propargylamidinourea l-[3-(3'-pyridyl)propylj-3-cyclobutylamidinourea l-[3- (3 '-pyridyl)propylj-3-cyclohexylamidinourea l-[3- (3'-pyridyl)propyl -3-benzylamidinourea 1-[3- (3'-pyridyl)propyl -3-methoxyethylamidinourea l-[3- (3'-pyridyl)propylj-3-benzyloxyethylamidinourea l-{3-(3'-pyridyl)propylj-3-methoxyethylamidinourea 1- [3- (3'-pyridyl)propyl -3-benzyloxyethylamidinourea 1-[3-(3'-pyridyl) ropylj-3-phenethoxyethylamidinourea 1—13- (3 '-pyridyl)propylj-3- (N, -dimethylamidino)u-rea l-[3-(3 '-pyridyl)propylj-3- (N,N-diethylamidino)urea 1-13-(3'-pyridyl)propyl -3-(N,N-pentamethyleneamidino)urea 1-13-( '-pyridyl)propyl]-3-methylamidinourea 1-13-(4'-pyridyl)propyl]-3-ethylamidinourea l-[3-(4'-pyridyl)propylj-3-propylamidinourea 1-13-( '-pyridyl)propylj-3-i-propylamidinourea l-[3- (4'-pyridyl)propyl]-3-butylamidinourea 1-13- (4 '-pyridyl)propyl]-3-r.-butylaniidinourea 1-[3- (4 '-pyridyl) ropyl]-3-pe ylamidinourea 1-13- (4'-pyridyl)propylj-3-hexylamidinourea OMPI -26- 1-[3- (4'-pyridyl)propylj-3-propargylamidinourea 1-13—(4'-pyridyl)propylj-3-allylamidinourea 1-13- (4'-pyridyl)propylj-3-methoxyethylamidinourea 1-[3-(4'-pyridyl)propylj-3-benzyloxyethylamidinourea 1-[3-(4'-pyridyl)propyl -3-phenethoxyethylamidinourea 1-[3- (4'-pyridyl)propyl -3-(N, -dimethylamidino)urea 1-13- (4'-pyridyl)propylj-3-(N,N-diethylamidino)urea 1-[3- (4'-pyridyl)propylj-3-(N-methyl-N-ethylamidino)urea l J EAS * * OMPI fy. WIPO _ " H -C 2 H 5 ~cH: H -CH. H '- H -CH. CH -CH. -CH. ζ CH. -H -CH. 0 CH: -H -C 2 H 5 ^>"CH - H -CH- 10- TABLE I-a NH H / 2 R 1 -N - - N = C N"~R. V S N U ' ^ H 2 CH 2 " H -CH- -BUREA OMPI TABLE I-a R, R R H 2 CH 2 - H -OCH. & -C 2 H 5 "C 2 H 5. BTT TABLE I-a N τ V- * C 2 H 2 CH 2 - -CH. -C 2 H 5 TABLE T-a N~~ R. ^ CH 2 - H -CH H -CH. TABLE I-a H -NH R, - N i y^ a . C -• N = 2 λ N *~~ - \ R. i R. R, R, R- R H 2 - H -CH. CH. t * X H -CH. CH 2 CH 2 - r CH. PI CH 2 -CH 2 - H -CH. > z> CH 2 -CH 2 - H - C 2 H 5 • TABLE II 1- (2-p [ yridylmet yl) -4-inet-hylamino-l , 2-di ydro-l , 3 , 5- riazin-2-one 1- (2-pyridylιrethyl ) -4-ethylaτnino-l , 2-di ydro-l , 3 , 5-triazin-2-one 1- (2-pyridylrrethyl) -4-propylamino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-pyridylnethyl) -4-i-ρropγlaπιino-l , 2 , -dihydro-1 , 3 , 5— triazin-2-one 1- (2-pyridylmethyl) -4-bu ylan no-l, 2-dihydro-l, 3 , 5-triazin-2-one 1- (2-pyridylnvethyl) -4-i-butylamLno-l , 2-dihydro—l , 3 , 5-triazin-2-one 1- (2-pyridylmethyl) -4-t-butylaτnino-l , 2-diftydro-l , 3 , 5-triazin-2-one 1- ( 2-pyridylmethyl) -4-pentyla ino-l , 2-di ydro-l , 3 , 5-txiazin-2-one 1- (2-pyridylrnethyl) -4-a 11 yla ino-1 , 2-d ydro-l , 3 , 5- riazin-2-one 1- (2-pyridylmethyl) -4-proparα^lamino-l, 2-diJnydro-l / 3 , 5-triazin-2-one 1- ( 2-pyridylmethyl) -4-cyclopropylaιnino-l , 2-dihydro-l , 3 , 5-triazin-2-on 1- (2-pyridylrreth.yl) -4-Η)ethαxyethylaιr±no-l , 2-dihydro-l , 3 , 5-triazin-2-o 1- (2-pyridylmet yl) -4-benzylα_^ethylaιrtino-l , 2- Lhydro-l , 3 , 5- riazin- 2-one 2-one 1- (2-pyridylmethyl) -4-benzylamino-l , 2-ό J ydro-l , 3 , 5-triazin-2-αne 1- (2-pyridylmethyl) -4- (N,N-dJιτιe .ylaιr rio) -1 , 2-dihydro-l , 3 , 5-txiazin- 2-one 1- (2-pyridylπethyl ) -4- (N ,N-c&e1±ιylaτrdjιo) -1 , 2-di ydro-l , 3 , 5-triazixι- 2-one 1- ( 2-pyridylmethyl ) — 4- ( -pyrrolidinyl ) -1 , 2-di ydrc-l , 3 , 5-triazirι- 2-one 1- (2-pyridylmethyl) -4- (N-piperidyl) -1 , 2-di ydrc>— 1 , 3 , 5-triazin-2-αne 1- (3-^met-αyl-2-pyriά imethyl) -4-net-hylamino-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- ( 3-ιrethyl-2-pyridylmethyl) -4-ethylaπ no-l , 2-dihydrσ-l , 3 , 5-triazin- 2-one 1- (3-ιne hyl-2-pyridylιrιethyl) -4-propylaτr-ino-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-n^t yl-2-pyrid _L er v-l) -4-i-propylarr±no-l , 2-dihydro-l ,3, 5- triaz in- 2-one 1- (3-in^1±yl-2-pyrid\'lrnet i'l) -4-butylaτr no-l , 2-dihydro-l , 3 , 5— fcriazin- 2-one -40- 1- -4-i-buiylaτπino-l,2-dihydro-l,3,5-triazin- 2-one 1- (3^τe hyl-2-pyridylιrethyl) -4-t-buiylaτr±rιo-l , 2-dihydro-l , 3 , 5-triazin- 2-one 5 1- (3-irethyl-2-pyridylrrethyl)-4-pentylaιι rιc^l,2 2-one 1- (3-rrethyl-2-pyridylmethyl) 4-allylaτrtir-θ-l 2-dihydro-l / 3,5-triazin^ 2-one 1- ( 3-ϊiiet-hyl-2-pyridylmethyl) -4-propargylaιτidno-l , 2-di-hydro-l , 3 , 5-triaziιι- 10 2-one 1- {3-iiethyl-2-pyridylrret-hyl) -4-cyclop.-Opylaιrd_αo-l, 2-dihydro-l ,3,5- triaz-Ln-2-one 1- (3-^iiethyl-2-pyridy2 r 1 e hyl) -4-cγclobutylaτr±no—l , 2-dihydro-l ,3,5- triazin-2-one 15 1- (3-πet±ιyl-2-pyriιdylrae hyl ) -4-cγclopenten-3-yl-aιrri-r-θ-l , 3 , 5-triazin- 2-one 1- ( 3-ιτethyl-2-pyridylιr thyl ) -4- ^lopropy.Lιτethylamino-l , 2-dihydro-l ,3,5- triazin— 2-one 1- ( 3-ιrιet- yl-2-py^idylιret-fιyl ) -4-ϊiιethoxye hylaιrιino-l , 2-d_L2ιydro-l ,3,5- 20 triazin-2-one 1- ( 3-ιrethyl-2-pyridy.Lπe hyl ) -4-ber-zyloxyei±.ylaιnino-l , 2-c_Lhydro-l ,3,5- riazirt-2-one 1- ( 3-aπrøthyl-2-pyridylmethyl ) -4-phenetboxyethylaτiiino-l , 2-d.Lhydro-l ,3, 5- triazin-2-one 25 1- (3-πιet-hyl-2-pyridylιrethyl) -4-benzylaτrιii-i3-l,2-d-U^ydro-l,3,5-triaz-Ln- 2-one 1- (3-^nethyl-2-pyridy_Lτnethyl) -4- (N,N-din-e hylair_ino) -1, 2-d-Lhydro-l,3 , 5- triazin-2-one 1- (3-mei±yl-2-pyridylme hyl) -4- (N,N-diethylamino) -1 , 2-di_hydro-l, 3 , 5- 30 triazin-2-on3 1- (3-ιre ±ιyl-2-pyridylmethyl) -4- (N-py-rrolid-lnyl) -1 , 2-d-U^dro-l ,3,5- triazin- 2-oπe 1- (3-ιre hyl-2-pyridylme ±Lyl) -4-13- Cr-rπethyl-piperi yl) j 1, 2-dihydro— 1,3, 5-txiazin-2-on3 35 1- -4-Ωet.πylaτπinD-l , 2-diJ ydro-l , 3 , 5-txiazin- 2-one OJMPI 1- (3-cMoro-2-pyridy-Lιrιet±ιyl) -4- (N-itDrpholinyl) -1, 2-dihydro-i,3 , 5- triazin-2-one 1- ( 3-chloro-2-pyridylmethyl) -4-ei±ιylamino-l , 2-dihydro-l , 3 , 5-triazin-2- one 1- 3-cMoro-2-pyridylιrethyl) -4-propylarruLno-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-chloro-2-pyridylmethyl) -4-i-propylaτπino-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-cMoro-2-pyridylmethyl) -4-butyla ino-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-chloro-2-pyridyl e ±ιyl) -4-i-butylaiϊiino-l, 2-dihydro— 1, 3, 5-triazin- 2-one 1- (3-cMoro-2-pyridylπεthyl) -4-t-butylaτrti_πo-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-cMoro-2-pyridyliBethyl ) -4-pentylaτrάno-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-chloro-2-pyridy.Lιτιe hyl) -4-propargylan-inc— 1, 2-dihydro-l , 3 , 5- riazin- 2-one 1- (3-chlorc -2-pyridylπιe hyl) -4-cyclobutylamino-l , 2-dihydrc—l , 3 , 5-triazin -2-one ■ 1- (3-chloro-2-pyridylπet-hyl) -4-cyclohexylaτ ιιc— 1 , 2-dihydro-l ,3,5- triazirt-2-oπe 1- (3-chloro-2-pyridylιi-etnyl)-4-^ -1,3,5-triazin- 2-one 1- (3-chloro-2-pyridylιαe ±iyl) -4-ιιet±ιo-^et±ιylaτrιino-l, 2-dihydrc—l, 3 , 5- triazin-2-one 1- (3-cMoro-2-pyridylme hy) -4-benzyloxyethylaτr±no-l , 2-dihydro—l ,3,5- triazin-2-one 1- ( 3-chlorc -2-pyridylmethyl ) -4-phene hoxyethylaτ7.ι ττα-1 , 2-dihydro-l ,3,5- triazin-2-one 1- (3-chloro-2-pyridy-Lτrethyl) -4- (N,N-diethylamino) -1 , 2-dihydro-l ,3,5- triazirt-2-one 1- -4- (N- pipe idinyi)-l, 2-di ydro-l,3 ,5-rria- zin— 2-one 1- (3-pyridylmethyl) -4-ιre hyl ami no-l , 2-d_Lhydrc-l , 3 , 5-triazin-2-one - REA Γ OMPI 1- ( 3-pyridylmsthyl) -4-ethylaιr rιc—l , 2-dihydrc—l , 3 , 5— fcriazin-2-one 1- (3-pyridyl ethyl) -4-propylamino-l, 2-dinydro-l,3, 5-triazih-2-one 1- (3-pyridylmεthyl) -4-i-propylaπ no-l , 2-dihydro-l , 3 , 5-txiazin-2-one 1- (3-pyridylmethyl) -4-butylaπti_αo-l, 2-dihydr HL ,3 , 5- riazin-2-one 1- (3-pyridylπethyl) -4-t-butylaτrtinσ-l , 2-dilιydro-l , 3 , 5-triazin-2-one 1- (3-pyridylmethyl) -4-pentylaπιiιτD-l, 2-dihydro-l -3 , 5-triazin-2-one 1- (3-pyridylrnethyl) -4-hexylaτninc-l , 2 , -dihydro-1 , 3 , 5-triazin-2-one 1- (3-pyridylιτethyl) -4-proparc^laπιino—l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (3-pyridylmei±iyl) -4-allyla ino— 1 , 2-dihydro-l , 3 , 5-triazin-2-one 1- (3-pyridylmei±ιyl) -4-ιrethσ yethyl ami no-1 , 2-dihydro-l , 3 , 5-triazin-2-one 1- (3-pyridylmethyl) -4-benzylα-ςyethylaτninc-l , 2-diJhydrc— 1 , 3 , 5-triazin- 2-one 1- (3-pyridylιrtethyl) -4-phenethαxyethyl ami no— 1 , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-pyridyιrk3thyl)-4- (N,N-dimethy1 amino) -1 , 2-dihydro— 1, 3 ,5-triazin-2- one 1- (3-pyridylrnethyl-4- (N,N-diethylaτnino) -1, 2-dihydro-l ,3 , 5- riazin-2-one 1- (3-pyridylιrEthyl) -4- (N-^rethyl-N-ethylamino) -1, 2-dihydro—l, 3 , 5- triazin-2-one 1- (3-pyridylιrethyl) -A- (N-pyrrolidyl) -1 , 2-dihydrc—l , 3 , 5-triazin-2-one 1- (3-pyridylιrιei±.yl) -4- (N-piperidyl) -1 , 2-dihydro-l , 3 , 5— hriazin-2-one 1- (3-pyridylmethyl) -4- (N-azipinyl) -1, 2-dihydro-l, 3 , 5-triazin-2-one „ 1- (4-pyridylmethyl) -4-nethylaτnino-l , 2-dihydro-l , 3 , 5-txiazin-2-one 1- (4-pyridylnie hyl) -4-ethylaιnino-l , 2-dihydro—l , 3 , 5-txiazin—2-one 1- (4-pyτridylmet-hyl) -4-propylaιnino— 1 , 2-dihydrc—l , 3 , 5-triazin-2-one 1- (4-pyridylmethyl) -4-butylaτrιinc— 1 , 2-dihydro—l , 3 , 5-triazin-2-one 1- (4-pyridylmethyl) -4-i-butylaτιιino-l , 2-dihydrc—l , 3 , 5-tria zin-2-one 1- (4-pyridy3methyl ) -^-pentylantino-1 , 2-dihydrσ-l , 3 , 5-triazin-2-one 1- ( 4-pyridylmethyl) -4-allylamino—l , 2-dihydro-l , 3 , 5-txiazin-2-one 1- (4-pyridylmethyl} -4-propargylaiir--no—l , 2-dihydrσ-l , 3 , 5-tria zin-2-one 1- (4-pyridylrrethyi} -4-ιτet κyet±ς 7 laιr-inc— 1 , 2-dihydro-l, 3 , 5-triazin-2-one 2-one 1- (4-pyridylmethyl) -4- (N,N-dimethylphenyl) -1 , 2-dihydrσ-l , 3 , 5-triazin- 2-one l- (4-pyridy0ιnethyl)-4- (N,N-diethylphenyl)-l,2-dihydrc-l,3, 5-t iazin- 2-one 1- (4-pyridylmethyl) -4- (N-pyrrolidinyl) -1, 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-methyl-4-f luoro-3-pyridylrnethyl) -4-methylaιr Lno-l, 2-dihydro— 1,3, 5-triaz in-2-one 1- ( 2 , 4-diirethyl-3-pyridylmethyl ) -4-ιret.hylam-Lno- 1 , 2-dihydro- 1 , 3 , 5-tria- zin-2-one 1- ( 2 , 4-diethyl-3-pyr idylraethyl ) -4-iiethylaτnino-l , 2-dihydro-l ,3,5- triazin-2-one 1- (2-ιrethyl-4-cMorc>-3-pyridylmethyl) -4-ittei±Lylami.no-l , 2-dihdyro-l ,3,5- triazin-2-one 1- ( 2-^raethyl-4-broπιo-3-pyridylrnethyl ) -4-roethylamino-l , 2-di-hydro-l ,3,5- triazin-2-one triazin-2-one 1- (2-ιτethyl-4-ethyl-3-pyridylrrethyl) -4-ιτethylaτrάnc— 1 , 2-dihydrc—l ,3,5- triazin-2-one 1- (2-e -hyl-4-chlorc^3-pyridylmethyl) -4-ιrethylamino-l, 2-dihydro-l, 3, 5- triazin-2-one 1- (2-ethyl-4-brcrD-3-pyridylmethyl) -4-ιτethylart±no-l , 2-d-Lhydro—l ,3, 5- triazin-2-one 1- (2-ethyl-4-f luoro-3-pyridylmethyl) -4-roethylamino-l , 2-dihydro-l ,3,5- triazin-2-one 1- ( 2 , 4-dircεthyl-3-pyridylethyl) -4-ιnethylamirιo-l , 2-dihydro-ϊ , 3 , 5-tria- zin-2-one 1- (2 , 6-die1±cyl-4-pyridylιnethyl) -4-ιτιei±ιylaιrιino-l , 2-dihydro-l , 3 , 5-tria- zin-2-one 1- {2- (2-mεthyl-6-ethyl-4-pyridyl) ethyl] -4-ϊτethylamino-l , 2-dihydro-l , 3- 5-triazin-2-one 1- (2-i±ιiophenylιr≤thyl) -4-^et^larr-ino-l , 2-dihycro— 1 , 3 , 5-triazin-2-one 1- ( 3-thiophenylre -hyl ) -4--τerhylaπιino-l , 2-d-Lhy ro-l , 3 , 5-triazin-2-one 1-12- (2-thiophenyl) ethyl] -4-ιrBthylaταino-l, 2-dihydro-l, 3 , 5-triazin-2-one 1-J3- (2-thiophenyl) propyl] -4-ιre ±ιylaτniικ>— l,2--d-i±ydrσ-l,3,5-triazi -2- one 1- [ 2- ( 3-thiophenyl ) ethyl] -4-methylaτnino-l , 2-di ydro-l , 3 , 5— riazin-2-one -BU EA OMPI 1- [ 3- (2-thiophenyl) propyl] -4-methylaπtino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- £2- (3-thiophenyl) ethyl] -4-methylaιπino-l , 2-dihydro-l, 3, 5-triazin-2-one 1- (5-ethyl-2-thiόphenylmethyl) -4-methylaτnino-l, 2-dihydro-l,3, 5-triazin- 2-one 1- ( 5-chlorc -2-tMophenyliΩethyl ) -4-ιτethylaιιιino-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-cyano-2-pyridylrrEthyl) -4-ιret-hylaτrύiϊθ-l, 2-dihydro-l , 3 , 5-triaziα-2- one 1- (3-carbαreι thc^-2-pyridylrretnyl) -4-ιtethylamino— 1 , 2-dihydrc—l ,3,5- triazin-2-one 1- ( 3-carboethQxy-2-pyridylmethyl) -4-jret-hylamLno-l , 2-dihydro-l ,3,5- triazin-2-one 1- ( 3-iπιethyl-2-pyridylrnethyl) -4-ιτEthylamino-l , 2-dihydro-l , 3 , 5-triazin- 2-σne 1- ( 2-methyl-3-pyridylmethyl) -4-πιethylatnino-l , 2-dihydro-l , 3 , 5-triazin- 2-one 2-one 1- ( 2 , 6-di[reti yl-3-ryridyl ethyl) -4-ιnethylaτnino-l , 2-dihydro-l ,3,5- triazin-2-one 1- (2-ethyl-6-br r ^3-pyridylmethyl) -4-πethylaτninc— 1, 2-dihydrc—l, 3 , 5- triazin-2-one 1- ( 2-ethyl- 6-f l ιoro-3-pyr idylmethyl ) -4-ιr-at±Lylaιιιino-l , 2-dihydro-l ,3,5- triazin-2-one 1- (3-cyanc^-2-t ophenylrnethyl) -4-ιnethylaraino-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-carbcιmεtbo-^-2-t ophenylιi3et±tyl) -4-jiEtl^laiiiinc^l,2-dihydro-l,3,5- triazin-2-one 1- (3-carbc>ethDxy-2-tMophenylιnethyl) -4-roethylamino-l , 2-dihy Lro—l ,3,5- triazin-2-one 1- (2-πιethαxy-3-pyridyl-τιethyl) -4- (N, N-diethylarnino) -1 , 2-dihycro-l ,3,5- triazi-n-2-one 1- (2-ethcc^-3-pyridylrnethyl) -4- (N-ethyl-N-ιrethylaιrιino) -1,2-dihydrσ— 1,3, 5-triazin-2-one OMPI _ 1- (2-chloro-3-pyridylmethyl) -4- (N-πethyl-N-propylamino) -1, 2-dihydro- 1,3, 5-triazin-2-one l-f rfuryl-4- (N-ιr i±tyl-N-butylaτnino) -1 , 2-dihydro-l , 3 , 5-triazin-2-one l-furfuryl-4- (N ,N-dipropylaιrιino) -1 , 2-dihydro-l , 3 , 5-triazin-2-one l-f rfuryl-4- (N-et±iyl-N-propylarriino) -1 , 2-dihydro-l , 3 , 5-triazin-2-one l-furfuryl-4- (N-πiethyl-N-benzylo^^^ropylaτnirio) -1 , 2-dihydro-l , 3 , 5-tria- zin— 2-one l-furfuryl-4- (N-^nrøttiyl-N-phenetho^ethylaiiiino) -1 , 2-dihydro-l ,3 ,5- triazin-2-one l-furfuryl-4- (l^ιτethyl-N-ben2ylαxye1±Lylaπιino) -1 , 2-dihydro-l ,3,5- triazin-2-one l-furfuryl-4- (N-pyrrolidinyl) -1 , 2-dihydro—l , 3 , 5-triazin-2-one l-furfuryl-4- (N-piperidyl) -1 , 2-dihydro-l , 3 , 5-triazin-2-αne l-furfuryl-4- (N-azipinyl) -1 , 2-dihydro-l , 3 , 5-triazin-2-one l-furfuryl-4- (N-πorpholinyl) -1, 2-dihydro-l, 3, 5-triazin-2-one l-f rfuryl-4- 13- (N-methylpiperidyl) -1 , 2-dihydro-l , 3 , 5-triazin-2-one " l-furfuryl-4- [3- (N-inethyl azipinyl) -l,2-dihydrc^l,3,5-triazin-2-one l-furfuryl-4- IN- (3-thicιτDrpnolinyl) ]-l,2-dihydr<o-l,3 ,5-triazin-2-one l-furfuryl-4- IN- (1-thioazolinyl ) ] -1 , 2-dihydro-l , 3 , 5-triazJLn-2-one l-furfuryl-4- (2-butenylami.no) -1 , 2-dihydro-l , 3 , 5-triazin-2-one l-furfuryl-4- (2-butylaτrdno) -1 , 2-dihydro-l , 3 , 5-triazin-2-one l-furfuryl-4- (3-butylamino) -l,2-dihydro-l,3, 5— riazin-2-one l-furfuryl-4- (N-methyl-N-allylamino) -1 , 2-dihydro-l , 3 , 5-triazin-2-one l-furfuryl-4- (N-irethyl-N-propargylainino) -1 , 2-dihydro-l , 3 , S^triazin- 2-one l-furfuryl-4- (N-iret3^1-N-cyclopropylainino) -1 , 2-dihydro-l , 3 , 5-triazin- 2-αne l-furfuryl-4-ϊτπet±ιylaα ιijιo-l, 2-dihydrc—l, 3 , 5-triazin-2-one l-furfuryl-4- (N,N-diπethylamino) -1 , 2-dihydro-l , 3 , 5-triazin-2-one l-tetrahyάlrofurfuryl-4-ιrethylaτnino-l , 2-dihydro-l , 3 , 5-triazin-2-one l-tetrahydrofurfuryl-4-methylaτr ι^N-l , 2-dihydro-l , 3 , 5-tria zin-2-one 1- (l--br-idazolylmethyl) -4-irethylaιr no-l , 2-d-Lhydro-l , 3 , 5- riazir.-2-one 1- (2-ii-iidazoiylmethyl) -4-ιτe1±ιylaιtιiικ>-l, 2-dihydro-l, 3 , 5- xiazir.-2-one 1- (4-imidazolylmethyl) -4- ethylaτr no-l, 2-dihydrc-l, 3 , 5-triazin-2-one 1- (2-αxazolylnethyl) -4-met_hylaτrtino-l, 2-dihydrσ-l , 3 , 5-triazin-2-one 1- ( 4-oxazolylmethyl) -4-methylaπύno-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 5-αxazolylιret.hyl) -4-!met±ιylaιr±rιo-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-t azolylπ^thyl)-4-ιιethylaιrώ o-l,2-dihydr 1- (4-thiazolylmεthyl) -4-methylaιπino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (5-thiazolylmεthyl) -4-rrethylamino-l, 2-dihydro-l , 3 , 5-triazin-2-one 1- (1-pyrazolylmethyl) -4--methylaπ no-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (1- 13-pyrrolidinyl] methyl) -4-roet±yi laminc— 1 , 2-dihydrc—l , 3 , 5-triazin- 2-one 1- (2-pyrroliάinylmethyl) -4-methylaτnino-l, 2-dihydro—l , 3 , 5-triazin-2-one 1- (l-πDrpholinylmethyl) -4-ιrethylaτr no-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-ιnorpholinylmethyl) -4-ιrethylamino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-pyrimidinylmethyl) -4-methylaτninc—l, 2-d i hydro— 1 , 3 , 5-triazin-2-one 1- ( 4-pyrinridinylπeth.yl) -4-ιrethylam_Lno-l , 2-dihydro— 1 , 3 , 5-tr iazin-2-one 1- (2-quinolinylιret-hyl)-4-me^ 1- (4-guiικNlinylraethyl) -4-methylami nc—1, 2-dihydro-l,3, 5-triazin-2-one 1- (1-iscquiιχNlinylmethyl) -4-ιrethylaιr no-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-dihydroinό jlinylmεthyl) -4-roethylaπuLno—l, 2-dihydro-l, 3, 5-triazin- 2-one 1-fur fury 1-4-ethylamino-l , 2-dihydro-l , 3 , 5-triazix.-2-one 1-fur furyl-4-prσpylaιrLino-l , 2-dihydro-l , 3 , 5-tr iaziιι-2-one l-furfuryl-4-i-propylaτπino-l , 2-dihydro-l , 3 , 5-tr i a zin-2-one l-furfuryl-4-buiγlaιrdrιo-l , 2-dihydro-l , 3 , 5-triazin-2-one l-furfuryl-4- (i-buiylamino) -l, 2-dihydro-l, 3, 5-triazin-2-one l- (2-pyridylrrethyl}-4-(sec-butyla-^^ 5-triazin-2-one 1- (2-pyridylmethyl) -4- (t-butylami no) -1, 2-dihydro-l, 3 , 5-triazin-2-one 1- ( 2-pyridylmethyl) -4-pen ylamino-l , 2-dihydro— 1 , 3 , 5-triazin-2-one 1- ( 2-pyridylmethyl) -4-he^laιtιino-l , 2-dihydro-l , 3 , 5-triazin-2-one l- (2-pyridylιrethyl)-4-heρtylaπιino-l, 2-dihydro— 1, 3, 5-triazin-2-one 1- (2-pyridylire1±tyl)-4-cyclopropylair^^ 1- (2-pyridylτrιethyl) -4-cyclobutylaπάriσ-l,2-di±ιydrcι-l,3,5-triazin-2-one 1- (2-pyridylmethyl) 1- (2-pyridy-Lιτ<etnyl} 1- ( 2-pyridylmethyl) -4-anilino-l , 2-dihydro—l , 3 , 5-triazin-2-one - U EA U OMPI 1- (2-pyridylmethyl) -4-benzylaιrύ.no-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-pyridylιrethyl) -4-phenei±ιylaτnino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-pyridylmethyl) -4- triazin-2-one 1- ( 2-pyridylmethyl-4- (N , N-dibenz lami o ) -1 , 2-dihydro-l , 3 , 5-triaz_Ln-2-one 1- (3-meth.yl-tet ahydrofurfuryl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one l-tet Dhydrofurfuryl-4-amino-l , 2-dihydrc—l , 3 , 5-triazin-2-one 1- (2-ιrtethyl-tetr«ahydrofι_ :furyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (l-j dazolylmethyl) -4-aτ no-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-methyl-l-irrddazolylrtιethyl) -4-amino-l , 2-dihydrc—l , 3 , 5-triazin-2-one 1- (4-irnidazolylmethyl) -4-aπιino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (l-πιethyl-4-i raά^zolyl-røthyl) -4-amino-l, 2-dihydro-l, 3 , 5-triazin-2-one 1- (2-methyl-4-i-nidazolylιnethyl) -4-amLno-l , 2-dihydro— 1, 3 , 5— triazin-2-one 1- ( 2-irtiidazolylmethyl) -4-amino-l , 2-dϋ ydro-l , 3 , 5-triazin-2-one 1- (2-oxazolylmεthyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 4-methyl-2- oxazolylmethyl ) -4-aminσ-l , 2-dihydro-l , 3 , 5-tr iazin-2-one 1- (4-oxazolylmethyl ) -4-aιtιino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-ιτethyl-4-oxazolylmethyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 5-oxazoϊylmethyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-mathyl-5-oxazolylraethyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 4-t azolylιrιethyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (5-ιrethyl-4-thiazolylιrethyl) -4-aminσ-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 5-t azolylmethyl) -4-amino-l , 2-dihydrc * -l , 3 , 5-triazin-2-one 1- (4-jriet±yl-5-i±ιiazolylrtiethyl) -4-aminc— 1 , 2-dihydrc—l , 3 , 5-triazin-2-one 1- (1-pyrazolylmethyl) -4-aιrtino-l , 2-dihydro— 1 , 3 , 5-triazin-2-one 1- (l-I3-pyrrolidinyl]methyl) -4-amino-l , 2-dihydro-l, 3 , 5-triazin-2-one 1- (2- [3-pyrrolidinyl]methyl) -4-amino-l, 2-dihydro-l,3 ,5-triazin-2-one 1- (1- I2-ιrethyl-3-pyrrolidiιιyl]ιrethyl) -4-aιnino-l , 2-dihydro-l , 3 , 5-triazin- 2-one 1- (1- [ 3-inethyl-2-pyrrolidinyl] methyl ) -4-aπ no-l , 2-dihydro— 1 , 3 , 5-triazin- 2-one 1- (l-pyrroiidinyl) -4-amino- 1, 2-dihydro— 1,3 , 5-txiazin-2-cne 1- (l-rnethyl-2-pyrrolidixιy_Lmethyl ) -4-amino-l , 2-dihi'dro-l , 3 , 5-triazin- 2-one -48- 1- (1-ιτorpholinylmethyl) -4-amino-l, 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 2-methyl-l-roorpholiny lmethyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-ιrDrpholinylmethyl) -4-«aτnino—l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (2-methyl-l-iιorρholinylιιιethyl) -4-aιnino-l, 2-dihydro-l,3 , 5-triazin-2-one 1- (2-ιtOrpholinylmethyl) -4-aτπino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (l-ιrethyl-2-morpholinylmethyl) -1, 2-dihydro-l,3 ,5-triazin-2-one 1- (3-ιτBthyl-2-rτDrpholiny3ιrethyl) -4-amino-l, 2-dihydro-l , 3 , 5-triazin- 2-one 1- (3-^tethyl-l-ιrorpholinyln^thyl) -4-amino-l, 2-dihydrσ-l, 3 , 5-triazin- 2-one 1- (3-OTorpholiny lmethyl) -4-amino-l , 2-άlihydro-l , 3 , 5-triazin-2-one 1- ( l-methyl-3-^TDrpholinyln.'ethyl) -4-aτr±no-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 2-ιιethyl-3-^ιorpholinylraethyl) -4-aιnino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 2-pyriιr .dinylmethyl) -4-aτπino-l , 2-dihy-dro— 1 , 3 , 5-triazin-2-one 1- ( 4τπrethyl-2-pyrimidinylmethyl) -4-aτπino-l , 2-dih.ydro-l , 3 , 5-triazin-2-one 1- (4-pyrirr dinylιriethyl) -4-aτnino-l, 2-dihydro-l , 3 , 5-triazin-2-one 1- ( 2-ιτethyl-4-pyrimidiny lmethyl ) -4-amino-l , 2-dihydro-l , 3 , 5— riazin-2-one 1- ( 2-quinolinylmεthyl) -4-amino— 1 , 2-dihydro-l , 3 , 5-triazin-2-one 1- (3-methyl-2-o^rJiκDlinylιτethyl) -4-aπtino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (4-giuinolinylmethyl) -4-aτπino-l, 2-dihydro-l, 3 , 5-triazin-2-one 1- (2-^rethyl-4-φαirolinylmethyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one 1- (3-methyl-4-quirκ_»linylπ^thyl) -4-amino-l , 2-dihydro-l, 3 , 5-triazixι-2-one 1- (1-isoquinol±nylmethyl) -4-amino-l , 2-dihydro-l , 3 , 5-triazin-2-one IJUREA^ OMPI . WIPO CH 2 - H ^2*5 CH Qπ H H -BVT OM TABLE III 1- (2-pyridylroethyl)-3-roethylaτr diι^ 1- (2-pyridylmethyl) -3-ethylamidiι »thiσurea 1- (2-pyridylroethyl)-3-propylaτr diιx>i±-iourea 1- (2-pyridy lmethyl) -3-i-propylamidinothiourea 1- (2-pyridylmethyl) -3-butylamid±nothiourea 1- (2-pyridylmethyl) -3-i-bu ylaιi-idirothiourea 1- (2-pyridylπethyl) -3-pentylaπ dinothiourea 1- (2-pyridylraethyl) -3-propargylaπtidi.not ourea 1- (2-pyridyImethyl) -3-allylam.idinothiourea 1- (2-pyridylmethyl) -3-πethoxyethylaιrάdinot ourea 1- (2-pyridylmethyl) -3-benzylcκyetihylamidinothiourea 1- (2-pyridylmethyl) -3-phenethcιχyethylaτr dinot±Lioi3rea 1- (2-pyridylroethyl) -3- (N,N-diπethylamidino) thiourea 1- (2-ρyridylmethyl) -3- (N,N-diethylaιτήdino) thiourea 1- (2-pyridylmethyl) -3- 0^,N-tetraτr thyleneamidino) thiourea 1- (2-pyridylmethyl) -3- (N,N-pentamethyleneaιradino) thiourea 1- (2-pyridylmethyl)-3- (N,N-hexaιrεthyleneamidino) thiourea 1- (3-πethyl-2-pyridylmethyl) -3-methylaτr dinothiourea 1- (3-met-hyl-2-pyridylrrethyl)-3-etiιyl^^ 1- (3-ιrethyl-2-py^idylιrιethyl} -3-propylamidiιιothiourea 1- (3-methyl-2-pyriάylmethyl) -3-i-propylaτr αinothiourea 1- (3-ιret±iyl-2-pyridylmethyl) -3-i-bu lamidiιιothiourea 1- (3-methyl-2-pyridylmethyl) -3-pen ylamidinothiooτrea 1- (3-ιτethyl-2-pyridyl ethyl) -3-«allylamidinothiourea 1- (3-ιretbyl-2-pyridylιretihyl) -3-propargylaπ dinothiourea 1- (3-ιrethyl-2-pyridylraethyl) -3-cyclcpropylarnidinothiourea 1- (3-methyl-2-pyridylmethyl) -3-methcιxyet±ιyl.amidijιot±ιiourea 1- (3-ιtιethyl-2-pyridylιrethyl) -3-benzylα^et.hylaιradinothiourea 1- (3-methyl-2-pyridylmethyl) -3-phenethoxyethylaιτάdinothiσ ιrea 1- (3-methyl-2-pyridylmethyl) -3-ber-zylamidinothiourea 1- (3-ιτ^th.yl-2-pyridy lmethyl) -3- ( ,!7-diιrethylaιτ diπo) thiourea 1- (3-met-hyl-2-pyridyLmethyl) -3- (N,N-tetramet-hyleneamidino) thiourea 1- (3-methyl-2-pyridylιrethyl) -3- (N,N-pentaιrethyleneaιτddino) thiourea 1- (3-chloro-2-pyridylmethyl) -3-πιethylamidinothiourea 1- (3-chloro-2-pyridy lmethyl) -3-et±ιylamidi-^i_hiourea 1- (3-chloro-2-pyridylmethyl) -3-propylaιιιLdinothiourea 1- (3-chloro-2-pyridylmethyl) -3-i^propylaτιadiιιothiourea 1- (3-chloro-2-pyridylmethyl) -3-butylaτrάdiιιothiourea 1- (3-chloro-2-pyridylmethyl) -3-i-butylaπadinothiourea 1- (3~chloro-2-pyridylmethyl) -3-t-butylaτπJ.d i nothiourea 1- (3-c± orc>-2-pyridylmethyl) -3-pentylaτnidinothiourea 1- (3-chloro-2-pyridylmethyl) -3-allylaιradinothiourea 1- (3-chloro-2-pyridylmethyl) -3-propargylamidinothiourea 1- (3-chloro-2-pyri(fylmethyl) -3-cyclopropylamLdiriθthiourea 1- (3-chJ.oro-2-pyridy lmethyl) -3-cyclobutylaιrddincrfc ourea 1- (3-c±tlorc>-2-pyridylιrethyl) -3- (N- I3-cyclopentenyl] air dino) thiourea 1- (3-chlor -2-pyridylraethyl) -3-cyclopropylιret±iylaπάdirκ3t± ourea 1- (3-c±uorcr-2-pyridylrr-athyl) -3-methoxyethylami i nothiourea 1- (3-chloro-2-pyridy lmethyl) -3-benzyloxyethylami dj.nothiourea 1- (3-chlαro-2-pyridylmethyl) -3-phenel± -cyethylaτridinoi± .ourea 1- ( 3-chloro-2-pyridylrrethyl ) -3-benzylamidinothiσurea 1- (3-chloro-2-pyridy lmethyl) -3- (N,N-diιrEthylaιrddixιo) thiourea 1- (3-chlorc 2-pyridylrnethyl)-3- (N,N-diet±ιylaιιd.dino) thiourea 1- (3-chloro-2-pyridylmethyl) -3- (N,N-tetraπι thyleneamidino) thiourea 1- (2-pyridy lmethyl) -3- (N,Nl3-methyl-3-azapentamei^leri«]aιιιidino) thiourea 1- (2-pyridylmethyl)-3- (N,Nl3-oxapentamethylene] amidino) thiourea 1- (2-pyridylmethyl)-3-methylaιr ^ 1- (2-pyridy lmethyl) -3-ethylamidinothiourea 1- (2-pyriάylmethyl)-3-ρropylaιr dinot± 1- ( 2-pyridy lmethyl ) -3-i-propylamidinothiourea 1- (2-pyridylmethyl) -3-rωtylamidinothiourea 1- (2-pyridy lmethyl) -3-i-butylaιt dinothiσurea 1- (3-pyriάylι et yl) -3-t-bu ^laιr dinothiσurea IJUREATT OMPI • (3-pyridylmethyl .)) -3-pentylaπ dinothiourea • (3-pyridylmethyl .)) -3-allylamidinothiourea • (3-pyridylmethyl .)) -3-propargylaτradinothiσurea ■ (3-pyridylmethyl .)) -3-cyclobutylaπ dinot ourea 1-((33--ppyyrriiddyyllmmeetthhyyll L))) -3-cyclohexylamidinothiσurea ' (3-pyridylmethyl .)) -3-benzylamidinoi± ourea ■ (3-pyridylmethyl .)) -3-methoxyethylamidinot± ourea • (3-pyridylmethyl .)) -3-benzylc>xyethylaτrddinothioι-xea ■ (3-pyridylmethyl .)) -3-phenethoxyethylamidincnihiourea 1- ■ (3-pyridylmethyl .)) -3- (N,Nr-dinethylamidino) thiourea ■ (3-pyridylmethyl .)] -3- ■ (3-pyridylιrsethyl .)) -3- (N,l^pentaτrethyleneaπ dino) thiourea • (4-pyridylmethyl .)) -3-ιrethyla dinothiourea • (4-pyridylmethyl .)) -3-et.hylaπ dinothiourea 1- • (4-pyridylmethyl .)) -3-propylamiά±r-othiourea • (4-pyridylmεthyl .)) -3-i-propylamidinothiσurea ■ (4-pyridylmethyl .)) -3-butylaιι_idinothiourea • (4-pyridylmethyl .)) -3-t-butylaιr dinotαiourea • (4-pyridylmethyl .)) -3-peniylaτπidinothiourea ■ (4-pyridylmethyl .)] -3-hexylaπύdiιιotlιiσurea ■ (4-pyridylroethyl .)) -3-p2^Dpargylaτώdi iDt±iάourea • (4-pyridylmethyl .)) -3-allylaιτάdirothiourea • (4-pyridylmethyl . )) -3-methoxyethylamiάlincrfchiσurea ■ (4-pyridylmethyl .)) -3-t^nzylc-xyerhylamidirιot±ιiourea 1- ■ ( (44--ppvyrriiddvyllmmeetthhyvll L))) -3-phenetx3xyethylaιrάdinothiourea • (4-pyridylmethyl .)) -3- (N,N-diιije&ylaτnidino) thiourea • (4-pyridylmethyl .)) -3- (N,N-diethylamidir)θ) thiourea ■ (4-pyridylmethyl .)) —3- (N-nethyl-N-ethylamidino) thiourea • 12- (2-pyridyl) ethyl] -3-ιι.ethylaιιιLdinothiourea 1-12- (2-pyridyl) ethyl] -3-ethylaπύdirothiourea ■ 12- (2-pyridyl) ethyl] -3-propylaπ dinothiourεa 1- [2- (2-pyridyl) ethyl] -3-i-prcpylanidinothic- .rea 1- [2- (2-pyridyl) ethyl] -3-butylamidirothiourea 1- [2- (2-pyridyl) ethyl] -3-i-bu1ylamidinothiourea 1- [2- (2-pyridyl) ethyl] -3-pentylamidinothiourea 1- 2- ( 2-pyridyl ) ethyl] -3-propargylarαidinothiourea 1- 2- (2-pyridyl) ethyl] -3-allylamidinothiourea 1- [2- (2-pyridyl) ethyl] -3-πethoxyethylamidinothiourea 1- 2- (2-pyridyl) ethyl] -3-benzyloxyethylaπ dinotiιiourea 1- [2- (2-pyridyl) ethyl] -3-phenet± 2-cyethylamidiιιothiourea 1- [2- (2-pyridyl) ethyl] -3- (N, N-dimethylamidino) thiourea 1- [2- (2-pyridyl) ethyl] -3- (N,N-diethylamidino) thiourea 1- [2- (2-pyridyl) ethyl] -3- (N,N-tet amet-hylenean dino) thiourea 1- [2- (2-pyridyl) ethyl] -3- (N,N-pentanethyleneamidino) thiσαrea 1- [2- ( 2-pyridyl) ethyl] -3- (N, N-hexamethyleneamidino) thiourea ■ 1- 2- (3-methyl-2-pyridyl) ethyl] -3-methylaττιidinothiourea 1- [2- (3-methyl-2-pyridyl) ethyl] -3-ethylaτιύdijothiσurea 1- [2- (3-methyl-2-pyridyl) ethyl] -3-propylamidinothiourea 1- 12- (3-methyl-2-pyridyl) ethyl] -3-i-propylamidinothiσurea 1-12- (3-methy 1-2-pyridyl) ethyl] -3-i-bu1γlamidinothiourea 1- 12- (3-methyl-2-pyridyl) ethyl] -3-pentylamidinothiourea 1- 2- ( 3-methyl-2-pyridyl ) ethyl] -3-allylaτr dinothiourea 1- 2- (3-methyl-2-pyridyl) ethyl] -3-propargylamidinothiourea 1- 12- (3-nethyl-2-pyridyl ) ethyl] -3-cyclopropylarrύdir-othioιιrea 1- 2- (3-methyl-2-pyridyl) ethyl] -3-ιrethoxyethylaτιd.dirκDt ourea 1- 2- (3-methyl-2-pyridyl) ethyl] -3-benzyloxyethylaτrύdinothiourea 1-12- (3-methyl-2-pyridyl ) ethyl] -3-phenethoxyet±ylaιnidi κNtiιiourea 1- 2- (3-methyl-2-pyridyl) ethyl] -3-benzylantidinothiourea 1- 2- (3- j methyl-2-pyridyl) ethyl] -3- (N,N-dimethylaιrύdino) thiourea 1-12- (3-methyl-2-pyridyl) ethyl] -3- (N,N-diethylamidino) thiourea 1-12- (3-methyl-2-pyridyl) ethyl] -3- (N,N-tetraτrethyleneaιrddino) thiourea 1-12- (3--ιιethyl-2-pyridyl) ethyl] -3- (N,N-pentaιικthyleneamidino) thiourea 1- 2- (3-chloro-2-pyridyl) ethyl] -3-methylamidinothiourea 1-J2- (3-chloro-2-pyridyl) ethyl] -3-ethylaτnidinothiourea 1-12- (3-chloro-2-pyridyl) ethyl] -3-propylarr dir.ct-hicurea 1-12- (3-cMorc>-2-pyridyl) ethyl] -3-i-propylaτrύdiιιothiourea -BϋR t AΪr OMPI -ciιlόro-2-pyridyl) ethyl] -3-butylaτtύdinothiourea -chloro-2-pyridyl) ethyl] -3-i-butylaττιidinothiourea -chloro-2-pyridyl) ethyl] -3-t-butylaιr dinothiourea -chlorc— 2-pyridyl) ethyl] -3-pen ylamidinothiourea -chloro-2-pyridyl) ethyl] -3-allylarrύdinothiourea -chloro-2-pyridyl) ethyl] -3-propargylamidinothiourea -chloro-2-pyridyl) ethyl] -3-cyclopropylamidiικ^thiourea -chloro-2-pyridyl) ethyl] -3-cyclobutylamidinothiourea -chloro-2-pyridyl) ethyl] -3- (N-I3-cyclopentenyl] amidino) thiourea -chloro-2-pyridyl) ethyl] -3-cycloprcpylii-e ±iyla]m.diiK)thiourea -chloro-2-pyridyl) ethyl] -3.-msi±oxyethylaτrddinothiourea -chloro-2-pyridyl) ethyl] -3-benzylαxyethylaιιήdinothiourea -chloro-2-pyridyl) ethyl] -3- (N,N-dirrethylan dino) thiourea -chloro-2-pyridyl) ethyl] -3- (N,N-diethylaιr dino) thiourea -dhloro-2-pyridyl) ethyl] -3- (N,l^te xamethyleneamidino)thiθιurea -pyridyl) ethyl] -3- (N,N -methyl-3-azapentamethylene] amidino) - -pyridyl) ethyl] - ■3- (N,N[3-αxapentamethylene] amidino) thiourea -pyridyl) ethyl] - ■3-methylamidinothiourea -pyridyl) ethyl] - ■3-ethylamidino thiourea -ρyridyl) ethyl] - •3-propylamidinothiourea -pyridyl) ethyl] - •3-i-propylaιτ dirothiourea -pyridyl) ethyl] - ■3-butylamidirothiourea -pyridyl) ethyl] - -i-butylaιr dinothiourea -pyridyl) ethyl] - -3-t-butylaιrάdirLθ ourea -pyridyl) ethyl] - -3-pen ylamidii )thiourea -pyridyl) ethyl] - ■3-allylaιnidiιχNthiourea -pyridyl) ethyl] - -3-propargylamidi ιcrthiourea -pyridyl) ethyl] - -3-cyclobutylamiά^crt±iourea -pyridyl) ethyl] - -3-cyclohexylaτrύd_lrx3tr .ourea -pyridyl) ethyl] - -3-benzylaτπidir-o ic rea -pyridyl) ethyl] - -3-methoxyet±ylaιrύdirισt±άourea -pyridyl) ethyl] • ■3-benzyloxyethylaιι dinothiourea - URE U" OMPI . WIPO . 1- [2- (3-pyridyl) ethyl] -3-phenet-hoxyethylamidύ ot± ourea 1- [2- (3-pyridyl) ethyl] -3- (N,N-din^1±ιylaπιidino) thiourea 1- [2- (3-pyridyl) ethyl] -3- (N,N-diethylamidino) thiourea 1- 2- (3-pyridyl) ethyl] -3- (N,N-pentamethyleneamidino) thiourea 1-12- (4-pyridyl) ethyl] -3-mei±ylaτrάdinothiourea 1- 2- (4-pyridyl) ethyl] -3-ethylamidirιothiourea 1- 2- (4-pyridyl) ethyl] -3-propylaπ dinothiourea 1- [2- (4-pyridyl) ethyl] -3-i-propylamid i nothiourea 1- [2- (4-pyridyl) ethyl] -3-butylamidinothiourea 1- [2- (4-pyridyl) ethyl] -3- t-butylami d i nothiourea 1- [2- (4-pyridyl) ethyl] -3-pentylarr dinothiourea 1- [2- (4-pyridyl) ethyl] -3-hexylamidixothiourea 1- 12- ( 4-pyr idy 1 ) ethyl] - 3-propargylarrύdiικyt±iourea 1-12- (4-pyridyl) ethyl] -3-allylaτnidinothiourea 1- [2- (4-pyridyl) ethyl] -3-ιrethc^ethylaτr dinothiourea 1- [2- (4-pyridyl) ethyl] -3-benzylc^ethylaτιύdinothiourea 1- 12- (4-pyridyl) ethyl] -3-phenethoxyethylaτr diι-ot±ιiourea 1- 2- (4-pyridyl) ethyl] -3- (N,N-dimethylaιrάdino) thiourea 1- 2- (4-pyridyl) ethyl] -3- (N,N-diethylamidino) thiourea 1-12- (4-pyridyl) ethyl] -3- (N-methyl-N-ethylamidino) thiourea 1- 3- (2-pyr idyl) propyl] -3-met±ylaπ dinothiourea 1-13- (2-pyridyl) propyl]— 3-ethylaττ dinothiσurea 1-13- (2-pyridyl) propyl] -3-propylamdinothiourea 1-13- (2-pyridyl ) propyl] -3-i-propylamidinothiourea 1-13- ( 2-pyridyl) propyl] -3-butylamidinothiourea 1- 13- (2-pyridyl) propyl] -3-i-butylaτιύdinothiourea 1- [3- (2-pyridyl) ropyl] -3-peniylamidinothiourea 1- 13- (2-pyridyl) propyl] -3-propargylan dinothiourea 1- [3- (2-pyridyl) propyl] -3-allylaιmdinothiourea 1- [3- (2-pyridyl) propyl] -3-ιυethoxyethylaιr diJHDthiourea 1-13- (2-pyridyl) propyl] -3-benzylc.jς^ethylamidinothiourea 1-13- (2-pyridyl) propyl] -3-phenet-hoxyεthylaπ d-L- >thiourea 1-13- (2-pyr idyl) propyl] -3- (N,N-dimethy lamidino) thiourea 1- 13- ( 2-pyridyl ) propyl] -3- (N , N-diethylamidino ) thiourea • 1-13- (2-pyridyl) propyl] -3- (N,N-tetrame1-hyleneamidino) thiourea 1- 13- (2-pyridyl) propyl] -3- (N,N-pentamethyleneamidino) thiourea 1-13- (2-pyridyl) propyl] -3- (N,N-hexaιrεthyleneaιr dino) thiourea 1- [3- (3-methyl-2- -pyridyl) propyl] -3-methylaτnidinothiourea 1- [3- (3-methyl-2 -pyridyl) propyl] -3-ethylamidinothiourea 1- 3- (3-jnethyl-2 -pyridyl) propyl] -3-propylaτrύdinothiourea 1- 13- (3-methyl-2- -pyridyl) propyl] -3-i-propylamidinothiourea 1- 3- (3-methyl-2- -pyridyl) propyl] -3-butylaιr diικ)tl iourea 1- 13- (3-methyl-2- -pyridyl) propyl] -3-i-butylamidinothiourea 1- 3- (3-methyl-2- -pyridyl) propyl] -3-pentylamidinothiourea 1- [3- (3-methyl-2- -pyridyl) propyl] -3-propaxgylaιτώdinothiourea 1- [3- (3-methyl-2- -pyridyl) ropyl] -3-allylamidinothiourea 1- [3- (3-methyl-2- • pyridyl) propyl] -3^netlx-^ethylaτr dinothiourea 1- [3- (3-methyl-2- ■ pyridyl) propyl] -3-benzylα^ethylamid-Lr«ot ourea 1- [3- (3-methyl-2- pyridyl) propylj -3-phenetho^ethylaτr dincrthiourea 1- [3- (3-methyl-2- pyridyl) propyl] -3-ben2ylamidinothiourea 1- [3- (3-ιrethyl-2- pyridyl) propyl] -3- (N,N-dimethylamidino) thiourea 1- [3- (3-^ιethyl-2- pyridyl) propyl] -3- (N,N-diet]^laτrddino) thiourea 1- 3- (3Hmethyl-2- pyridyl) propyl] -3- 1- 13- (3-methyl-2- pyridyl) propyl] -3- (N,N-pentamethyleneaτπidino) thiourea 1- [3- (3-chloro-2- pyridyl) propyl] -3-ιrethylaπιidirothiourea 1- 13- (3-chlόro-2- pyridyl) propyl] -3-^i±ylaτιtidinothiourea 1- 3- (3-chloro-2- pyridyl) propyl] -3-proρylamidinothiourea 1- 3- (3-chloro-2- pyridyl) propylj -3-i-propylaτι dinothiσurεa 1- 13- (3-chloro-2- pyridyl) propylj -3-butylamidinothiourea 1- 13- (3-chloro-2- pyridyl) propylj -3-i-butylamidinothiourea - 1- 13- (3-chloro-2- pyridyl) propyl] -3-t-butylaπύdinothiourea - 1- 13- (3-chloro-2- pyridyl ) propyl] -3-p«ntylaιnidiιχy hiourea 1- 13- (3-chloro-2- pyridyl) propyl] -3-allyl ami d i nothiourea 1- 13- (3-chloro-2- pyridyl) propyl] -3-propargylamidinothiourea 1- 13- (3-chloro-2- pyridyl) propyl] -3-cyclopropylaτr dinothiσαrea 1- [3- (3-chloro-2- • pyridyl) propyl] -3-cyclobutylaπύdinothiourea 1- 13- (3-chloro-2- pyridyl) propyl] -3- (Iv-I3-cyclopentenyl] arridino) thiourea 1- 13- (3-chloro-2- pyridyl) cropyl] —3—r- -rl n—~rzrrγl TT T-pyl ~τ.i r. - ~--r,τ"~ i m ?τ-«=q 1- 13- (3-chloro-2- pyridyl) propyl] -3-x^thoxyethylaιrάdinot iourea 1- 13- (3-chloro-2- pyridyl) propyl] -3-benzylcκyethylamidinothiourea 1- 3- (3-chloro-2- pyridyl) propyl-3-phenethQ-^ethylaτmdiιιotmc>urea -Bϋ EA OMPI 1- [3- (3-chloro-2-pyridyl) propyl] -3-benzylajτddinothiourea 1- [3- (3-chloro-2-pyridyl) propylj -3- (N,N-dimethylaιτ dino) thiourea 1-13- {3-chloro-2-pyridyl) propyl] -3- (N,N-diet±ιylamύdino) thiourea 1-13- (3-chloro-2-ρyridyl) propylj -3- (N,N-tetramethyleneamidino) thiourea 1- 3- (2-pyridyl) propyl] -3- (N ,Nl3-ιrethyl-3-azapentamethylene] amidino) - thiourea 1- [3- (2-pyr idyl) propylj -3- (N,NI3-Qxapentamethylene amidino) thiourea 1- [3- (2-pyridyl) propylj -3-ιrøthylamidinothiourea 1- [3- (2-pyridyl) propylj -3-ethylaτπidino thiourea 1- 13- ( 2-pyridyl ) propylj -3-propylamidinothiourea 1- [ 3- (2-pyridyl ) propylj -3-i-propylaπ dinothiourea 1- 13- (2-pyridyl) propylj -3-butylamidinothiourea 1- 13- ( 2-pyridyl ) propylj -3-i-butylamidinothiourea 1- 3- (3-ρyridyl) propylj -3-t-bu ylaamdiιx3thiourea 1- [ 3- ( 3-pyr idyl ) propyl -3-pentylaιr dinothiourea 1- [3- (3-pyridyl) propylj -3-ally-amidinothiσurea 1- 13- (3-pyridyl) propylj -3-propargylaιrddinothiourea 1- 3- (3-pyridyl) propyl -3-cyclobutylaιι dinothiourea 1- 3- (3-pyridyl) propylj -3-cyclohexylaιιύdix 3thiourea - 13- (3-pyridyl) propylj -3-benzyl-mάdinothiourea 1-13- (3-pyridyl) propyl] -3-mei±ii -xyethyl.amidi-nott ourea 1-13- (3-pyridyl) propylj -3-benzylθ3Q^thylaπudinotlιiσurea 1- 3- (3-pyridyl) propyl] -3-methoxyerhylamiά i χ)thiourea 1- 13- (3-pyridyl) propyl] -3-phenethθ2>iyethylaiiτLdinothiourea 1-13- (3-pyridyl) propyl] -3- (N,N-diιrethylamidino) thiourea 1-13- (3-pyridyl) propyl] -3- (N,N-diethylamidino) thiourea 1-13- (3-pyridyl) propyl] -3- (N,N~peni^methyleneamidino) thiourea 1- 3- ( 4-pyridyl ) propyl] -3-methylami d i nothiourea 1- 13- (4-pyridyl) propyl] -3-ethylaτnidinothiourea 1- [ 3- ( 4-pyridyl ) propyl] -3-propylaτrύdinothiourea 1- 13- (4-pyriαyl ) propyl] -3-i-propylamidir.ot± ourea 1- [3- (4-pyridyl ) propyl] -3-butylaτιύdi_nothiσ-irea 1-13- (4-pyridyl) propyl] -3-t-butylaiιiLd-Lnothiourea 1- [3- (4-pyridyl) propyl] -3-pentylamidinothiourea 1- [3- (4-pyridyl) propyl] -3-he^lamidinothiourea 1- 3- (4-pyridyl ) propyl] -3-propargylaτr diiϋthiσurea 1-13- (4-pyridyl) propyl] -3-allylaπύdiιχNthiourea 1-13- (4-pyridyl) propyl] -3-Ηetho^ethylamidiιx3tMσurea 1-13- (4-pyridyl) propyl] -3-benzyloxyethylaιrύdirκDthiourea 1- 13- (4-pyridyl) propylj -3-phenet±ιo^ethylaraidixιθthiourea 1- 13- (4-pyridyl) propylj -3- (N,N-dimethylamidi-Sθ) thiourea 1- [3- (4-pyridyl) propylj -3- (N,N-diethylamidino) thiourea 1- 3- (4-pyridyl) propylj -3- (N- rethyl-N-ethylaitddino) thiourea I J U E IΓ OMPI s TA3LE IV 1-(2 -pyridylmethyl)-4-methylamino-l,2-dihydro-l,3,5-triazin-2-thione 1-(2 -pyridylmethyl)-4-ethylamino-l,2-dihydro-l,3,5-triazin-2-thione 1-(2 -pyridylmethyl)-4-propylamino-l,2-dihydro-l,3,5,-triazin-2-thione l-(2 -pyridylmethyl)-4-i-propylaraLno-l,2-dihydro-l,3,5-triazin-2- thione 1-(2 -pyrid lmethyl)-4-butylamino-l,2-dihydro-l,3,5-triazin-2-thione 1-(2 -pyridylmethyl)-4-i-butylamino-l,2-dihydro-l,3,5-triazin-2-thione 1-(2 -pyridylmethyl)-4-t-butylamino-l,2-dihydrσ-l,3,5-triazin-2-thione l-(2 -pyridylirethyl)-4-pentylamuo-l,2-^^ 1- ( 2 -pyridylmethyl) -4-allylaπιino-l , 2-dihydro-l , 3 , 5-triazin-2-thione 1- (2 -pyriάylmethyl) -4-propargylamino-l , 2-dihydro-l , 3 , 5-triazin-2- thione 1-(2 -pyridylmethyl)-4-cyclopropylaτrdjno-l,2-dihydro-l,3,5-triazin-2- thione 1-(2 -pyridylmethyl)-4-methθ-^et±ιylamino-l,2-dihydro-l,3,5-triazin-2- thione 1-(2 -pyridylmethyl)-4-benzyloxyethylamino-l,2-dihydro-l,3,5-triazin- 2-thione 1-(2 -pyridylmethyl)-4-phenethoxyethylamino-l,2-dihydro-l,3,5-triazin- 2-thione 1-(2 -pyridylmethyl)-4-benzylamino-l,2-dihydro-l,3,5-triazin-2- thione 1- ( 2 -pyridylmethyl) -4- (N ,N-dimet±ιylaιιιino) -1 , 2-dihydro— 1 , , 5-triazin- 2-thiσne 1-(2 -pyridylmethyl)-4-( ,N-diethylamino)-1,2-dihydro-l,3,5-triazin- 2-thione 1-(2 -pyridylmethyl)-4-(N-pyrrolidinyl)-1,2-dihydro-l,3,5-triazin- 2-thione l- (2 -pyridylmethyl) -4- (N-piperidyl) -1,2-hydro-l, 3, 5-triazin-2-thione 1- (3 -methyl-2-pyridy lmethyl) -4-ιτεthylairιino-l , 2-dihydro-l ,3 ,5- triazin-2-thione 1- ( 3 -methyl-2 -pyridylmethyl ) -4 -et±ιylamino-1 , 2-dihydrc—l ,3,5- triazin-2-thione l- (3 -methyl-2 -pyridylmethyl) -4 -proρylaminσ-l,2-hydro-l, 3, 5-triazin- 2-thione l- (3 -methyl-2 -pyridylmethyl) -4 -i-proρylamino-l,2-dilιydro-l, 3, 5- l-(3 -methyl-2 -pyridylmethyl)-4-butylaτπino-l,2-dihydro-l,3,5-triazin- 2-thione l-(2 -πorpholinylmethyl) -4-met±ιylamino^ 2-thione l-(2 -pyriιιύ.όιny2ιrethyl) -4-methy^ 2-thione 1- (4 -pyriirύdinylmethyl) -4-methylaιιti-no-l , 2-dihydro-l , 3 , 5— riazin- 2-thione 1- (2 -quiixDlinylmethyl) -4-methylamino-l, 2-dihydro-l, 3 ,5— riazin- 2-thiαne 1- (4 - juixolinylmethyl) -4-methylamino-l , 2-dihydro-l , 3 , 5-triazin-2- thione 2-thione l-(2 -dihydroindolinyl eth^ triazin-2-thione l-fLu furyl-4-ei±ylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione l-furfuryl-4-ρropylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione l-furfuryl-4-i-propylamino—l , 2-dihydro-l , 3 , 5-triazin-2-thione l-furfuryl-4-butylaminσ-l , 2-dihydro-l , 3 , 5-triazin-2-thione l-furfuryl-4- (i-butylainino) -1 , 2-dihydro-l ,3 , 5-triazin-2-thione 1- (2 -pyridylmethyl) -4- (sec^butylamino) -1 , 2-dihydro-l , 3 , 5-triazin- 2-thione 1- (2 -pyridylmethyl) -4- (t-bu±ylamino) -1 , 2-dihydro-l , 3 , 5-triazin- 2-thione 1- ( 2 -pyridylmethyl ) -4-pentylamino— 1 , 2-dihydro-l , 3 , 5-triazin-2- thione 1- ( 2 -pyridylmethyl ) -4-he^lamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione 1- (2 -pyridylmethyl) -4-heptylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione l-(2 -pyridyliretihyl) -4-cyclop:π-^ 2-thione 1- ( 2 -pyridylmethyl ) -4 -cyclobutyla-τιino-1 , 2-dihydro-l , 3 , 5-triazin- 2-thione 1-(2 -pyridylmethyl)-4-cyclcpentyiar:.ino-l,2-dihydro-l,3,5-triazin- 2-thione 1- (2 -pyridylmethyl) -4-cyclohe^lamino-l , 2-dihydro-l , 3 , 5-triazin- 2-thione 1- (2 -pyridylmethyl) -4-anilino-l , 2-dihydro-l , 3 , 5-triazin-2-thione 1- (2 -pyridylmethyl ) -4-benzylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione 1- (2 -pyridylmethyl) -4-phenethylamino-l , 2-dihydro-l , 3 , 5-triazin-2- thione 1- ( 2 -pyridylmethyl ) -4- (N-methyl^-benzylamino) -1 , 2-dihydro-l ,3,5- ' triazin-2-thione 1- (2 -pyridylmethyl) -4- (N, -dibenzylamino) -l,2-dihydro-l,3 ,5- triazin-2-thione 1- (3 -iiπethyl-tetrahydrofurfuryl ) -4-amino-l , 2-dihydro-l , 3 , 5-triazin- 2-thione l-tetrahydrofurfuryl-4-aτnino-l , 2-dihydro-l , 3 , 5-triazin-2-thione 1- (2-methyl-tetrahydrofurfuryl ) -4-aτπino-l , 2-dihydro-l , 3 , 5-triazin- 2-thione l- (2 -methyl-3 -pyridylmethyl ) -4-methylaτrdno-l , 2-dihydro-l , 3,5- triazin-2-thione l- (2 -ethyl-3 -pyridylmethyl )-4→rethylamino-l,2-hydro-l, 3, 5-triazin- 2-thione 1- (2 , 6 ' -dimethyl-3 -pyridylmethyl) -4-methylaιrιino-l , 2-hydro-l ,3 ,5- triazin-2-thione l- (2 -ethyl-6 -bromo-3 -pyridyl r t±ιyl) -4-^iιethylaιιdrιo-l,2-dihydro- 1,3, 5-triazin-2-thione l- (2 -ethyl-6 -fluor — 3 -pyridylιi- t-hyl) -4-methylaιr±nc»-l,2-dihydro- 1,3, 5-triazin-2-thione l- (3 -cyano-2 -thiophenylrrethyl) -4-methylaιr _no-l,2-dΛ triazin-2-thione l- (3 -cartx3iιethyoxy-2 -thiσphenylιιethyl) -4-iiιe1 ylamino-l,2-dihydro- 1,3, 5-triazin-2-thione l- (3 -carboethoxy-2 -thiophenylmethyl) 1,3, 5-triazin-2-thione l-(2 -methoxy-3 -pyridylmethyl) -4- (N,N-diethylaιrLirκD) -l,2-ddhydro- l,3,5-triazin-2-thione l-(2 -ethoxy-3 -pyridylirei±iyl) -4- (N-etihyl-N-mεth^ 1,3 , 5-triazin-2-thione l- (2 -chloro-3 -pyridyl ret yl) -4- (N-^nethyl -N-propyla-rino) -1, 2- dihydro-1 , 3 , 5-triazin-2-thicne l-furfuryl-4- (N-met±iyl-N-butylaiiii-no) -1 , 2-dihydro-l , 3 , 5-triazin- 2-thione l-furfuryl-4- (N ,N-diprcpylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione OMPI l-furfuryl-4- (N-ethyl-N-propylainino) 1 , 2-dihydro-l , 3 , 5-triazin- 2-thione l-rurfuryl-4- (N-methyl_N Denzylo ypropylamino) -1 , 2-dihydro-l ,3,5- triazin-2-thione l-furfuryl-4- (N-methyl^-phenethoxylaιιti-no) -1 , 2-dihydro-l ,3 ,5- triazin-2-thione l-furfuryl-4- (N-^tethyl-N-benzyloxyethylamino) -1 , 2-dihydro-l ,3,5- triazi n-2-thione l-furfuryl-4 (N-purrolidinyl ) -1 , 2-dihydrσ-l , 3 , 5-triazin-2-thione l-furfuryl-4- (N-piperitdyl) -1 , 2-dihydro-l , 3 , 5-triazin-2-thiσne l-furfuryl-4- (N-azipinyl) 1 , 2-dihydro-l , 3 , 5-triazin-2-thione l-furfuryl-4- (N-morpholinyl) -l,2-dihydro-l,3 ,5-triazin-2-thione l-furfuryl-4-/3 " - (N-methyl piperidyl) _71 , 2-dihydro-l , 3 , 5-triazin- 2-thione l- (3 -chloro-2 -py^idylmet±ιyl)-4-ρropylarrιino-l,2-dihydro-l,3,5- triazin-2-thione l-(3 -chloro—2 -pyridylmethyl)-4-i-^ropylamino-l,2-dilιydro-l,3,5- triazin-2-thione l-(3 -chloro-2 •^3y^idylιretnyl)-4-butylaτrdχ>-l,2-dihydro-l,3,5- triazin-2-thione l-(3 -dhloro-2 -pyri<^lιrethyl)-4-i-but5d.aπ±no-l,2-dihydro-l,3,5- triazin-2-thione l- (3 -chloro-2 -pyridylmethyl) -4-t-buiylamino-l,2-dihydro-l, 3,5- triazin-2-thione l-(3 -chloro-2 -pyridylii thyl) -4-pentylamirι^ triazin— 2— hione l- (3 -chloro-2 -pyridylitethyl) -4-prcpar^ triazin-2-thione l- (3 -chloro-2 -pyridylπethyl) -4-cyclob iylaτ^ triazin—2-thione l- (3 -chloro-2 -pyridylιrethyl) -4- ^clohe}cylaιr^^ triazin-2-thione 1- ( 3 -chloro— 2 -pyridylirethyl ) -4-benzyl-r±r.o-i , 2-cihydro— 1 ,3 ,5- triazin-2-thione l- (3 -chloro— 2 -pyridylιrethyl)-4-methoxyethylaι^ triazin-2-thione l-(3 -chloro-2 -pyridylιret±ιyl) -4-benzylcκyei±ιyl.amino-l,2-di^ 1,3,5-triazin-2-thione l- (3 -chloro-2 -pyridylmethyl) -4-phenetho^ethylamino-l,2-dihydro- 1,3, 5-triazin-2-thione l- (3 -chloro-2 -pyriάylmethyl-4-(N,N-diethylarnino)-l,2-dihydro- 1,3, 5-triazin-2— hione l- (3 -chloro-2 -pyridylιτethyl)-4- (N-piperidinyl) -l,2-dihydro-l,3,5- triazin-2-thione 1- (3 -pyridylmethyl) -4-methylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione 1- (3 -pyridylmethyl ) -4-ethylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione 1- (3 -pyridylmethyl) -4-propylamino-l , 2-dihydrc—l , 3 , 5-triazin-2-thione l- (3 -pyridylmethyl) -4-i-propylaιr ιιo-l,2-dihydro-l, 3 , 5-triazin-2- thione 1- ( 3 -pyridylmethyl ) -4-butylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione 1- ( 3 -pyridylmethyl ) -4-t~butylamino-l , 2-dihydro-l , 3 , 5-triazin-2- thione 1- (3 -pyridylmethyl) -4-pentylamino-l , 2-dihydro-l , 3 , 5-triazin-2-thione l- (3 -pyridylmethyl) -4-hexylarrάriθ-l , 2-di.hydro-l , 3 , 5-triazin-2 TABLE V X X = O, S R 3 R 4 OMPI TA3LE V C -CH. -CH- J 3 ζ>-- > H TABLE V R-, R- R CH-, TABLE V TABLE V H k O- CH. -CH. -CH. TABLE V R- R, </ \ CH. -CH. -CH. \-=W TA3LE V Rπ R- H ' \\ - ~ -H -CH. TABLE V ~CHCH 2 - -CH. -CH- TABLE V R, R- "BURE OMPI WIPO TABLE V R. R- " URE L OMPI TABLE V R-, R, CH 3 H Q -CH 2 CK 2 - CH. H N 7 CH 2 CH 2 - H -CH. N H 0 \ \\ CF -CF - 2 2 TA3LΞ V 'c " ^ 2: "CH 2- H -CH. TABLE V R. l-aryl-l,2-dihydro-s-triazine derivatives are known to possess a broad spectrum of biological activity (Hetero¬ cyclic Compounds, Vol. 7, John Wiley & Sons, Inc., 1961, p. 717-18) . The novel compounds of this invention consti- tute a new class of l-aralkyl-l,2-dihydro-2-triazines, particularly 1-heterocyclic alkylene-l, " 2-dihydro-l,3,5- triazine-2-ones which similarly have a broad spectrum of biological activity. Thus, these compounds possess useful gastrointestinal actions and can be used for example as antidiarrheal agents for the treatment of gastrointestinal disorders. Whereas amidinoureas also have local anesthetic and other pharmacological effects when admini¬ stered at dose levels for effective antidiarrheal action, certain of the novel triazinones possess good antidiarrheal activity without local anesthetic or other side effects at active dose levels. Certain of the novel triazine derivatives possess other gastrogenic and related effects, particularly antisecretory action, making them useful in the treatment of such gastrointestinal disorders as peptic ulcers. Compounds of this series also possess anti- otility and spasmolytic effects making them useful in the control of muscle spasm particularly stomach or intestinal spasms. Certain of the compounds also exhibit novel effects on nerve impulse transmissions wherein multiple high frequency nerve transmissions are -blocked. The amidinoureas from which the novel triazine deri¬ vatives are prepared according to this invention possess useful pharmacological properties including antidiarrheal activity in mammalian species. Generally, it has been found that the antidiarrheal properties of the amidinourea are not lost in cyclizing to the corresponding triazine derivative. Accordingly, the novel triazine derivatives of this invention are also useful antidiarrheal agents as shown by test results in animals, which, based on previous experience with the corresponding amidinoureas, show good correlation to activity in humans. Various tests can be carried out in animal models to show the ability of the heterocyclic alkylene triazinones of this invention to exhibit reactions that can be correlated with anti-diarrheal activity in humans. The following tests show the ability of the compounds of this invention to inhibit diarrhea in animals and are known to correlate well with antidiarrheal activity in humans. These are considered to be standard tests used to determine antidiarrheal properties. This corre- lation can be shown by the activities of compounds known to be clinically active. The test compound is dissolved in distilled water, unless otherwise stated. The EDJ- Q values and 95% confidence limits are calculated according to a method described by D. F. Finney (Probit Analysis, 2nd Ed., university Press, Cambridge, p. 236, 1964) . 1. Antagonism of Castor Oil-induced Diarrhea in Mice A modified test described by Niemegeers et al. (Arzneim-Forscth 22, 516-518, 1972) was used. Groups of ten male Swiss Webster mice (22-25 g) were randomly selected for dosing. Castor oil (Fischer Scientific Co.), 0.3 ml/mouse, was given orally one hour after an oral dose of test compound or the vehicle. After dos"ing with castor oil, each mouse was placed into an individual wire cage and observed for six hours for diarrhea. 2. Antagonism of Castor Oil-induced Diarrhea in Rats A test described by Niemegeers et al. (supra) was used. Groups of ten female Wistar rats (180-200 g) were randomly selected for dosing. In addition, groups of ten female Sprague-Dawly rats (130-200 g) were used to determine strain difference. Castor oil (Fisher Scienti¬ fic Co.) , 1 ml/rate, was given orally one hour after an oral dose of test compound or the vehicle. After dosing with castor oil, each rat was placed into an individual wire cage and observed for six hours for diarrhea 3. Antagonism of Chemically-induced Diarrhea in Mice Male Swiss Webster mice (18-22 g) in groups of 10-20 mice were randomly selected for oral dosing with test compound or the vehicle one hour before the inter- peritoneal injection of either 400 g/kg of Carbachol (carbamycholine chloride, Sigma Chemical Co., St. Louis, Missouri) ; or, 200 g/kg of serotinin creatine sulfate (Schwartz/Mann Biochemicals, Orangeburg, New York) . After each mouse was injected, it was placed into an individual wire cage and observed for diarrhea. 4. Inhibition of the Gastrointestinal Transit Time of a Charcoal Meal in Mice A charcoal suspension (10 ml/kg of a 10% suspension) was given orally to groups of ten Swiss Webster male mice (18-22 g) one hour after an oral dose of test compound or vehicle. The mice were sacrificed by cervical dislocation 30 minutes after the charcoal meal and the distance in millimeters that the charcoal meal traveled through the small intestine was measured and compared to the controls. Mean distance in controls - mean distance in treated X 100 = % Inhibition Mean distance in controls 5. The Effect of Naloxone on the Inhibitory Actions of Triazinones on Gastrointestinal Motility Male Swiss Webster mice (18-20 g) in groups of ten were randomly selected for dosing with test compound or the vehicle alone and concimitantly with naloxone. The naloxone was dissolved in saline. The mice were given a charcoal meal (10 ml/kg of a 10% suspension) one hour after an oral dose of the vehicle or a test compound(s). Thirty minutes after the charcoal meal the mice were sacrificed by cervical dislocation and the distance in millimeters that the charcoal meal traveled through the small intestine was measured and compared to the controls. 6. Fecal Output Tolerance Study in Rats Male Wistar rats (140-180 g) were given oral doses of either test compound, diphenoxylate HC1 (suspended in methylcellulose or the vehicle (distilled water or methylcellulose) once a day for five consecutive days. Vehicle or the test compound were given daily 30 minutes before fecal collection. The feces were collected in a completely automated four-tiered metabolic cage over a 12-hour period consisting of three, four-hour intervals. Following collection, the feces were dried for four hours at 200°C and weighed. 7. Prostaglandin test An intraperitoneal injection of 100 icrograms per kilogram of PGE2 causes diarrhea in mice within ten minutes. Groups of mice were orally dosed with test compound at various dose levels after which the PGE 2 is given and ten minutes later the mice are checked for diarrhea to determine the ED 5Q . The amidinourea starting materials, in addition to having antidiarrheal properties, possess other pharma¬ cological cativities such as local anesthetic and cardio¬ vascular activity. Unlike the amidinoureas which generally have local anesthetic properties, the pharma¬ ceutically useful 1-he erocyclic alkylene-1,2-dihydro- l,3,5-triazin-2-ones and thiones of this invention are more specific and possess little or no classical local anesthetic effects, nor do they possess significant cardiovascular effects. The compounds of Formula I are particularly useful as antidiarrheal agents where it is desirable to achieve an antidiarrheal effect with a minimum of side effects and these compounds are therefore especially suited to the treatment of gastrogenic diarrhea. The tests employed to determine the separation of local anesthetic and cardiovascular activity at effective antidiarrheal doese with representative compounds of the formula above are described below. Several different procedures generally employed in testing for local anesthetic activity are used to deter¬ mine local anesthetic effects. These tests have been used extensively in the past and have given satisfactory results in defining the local anesthetic properties of compounds. A discussion of experimental methods for evaluating local anesthetic properties of drugs is found in Evaluation of Drug Activities; Pharmacometrics, Vol. 1, Ed by D. R. Lawrence and A.L. Bacharach, Academic Press, Inc. (London) Ltd. (1964) . Applicants herewith incorporate by reference Chapter 9 of this book entitled "Local Anesthetics", pages 204-214. Tests which show the lack of side effects of the preferred triazinone . compounds include the following: 1. Effect of Hexobarbital-Induced Loss of Righting Reflex The test compound and a vehicle given orally thirty minutes before hexobarbital were compared for their effect on the duration of the loss of righting reflex (failure to right within five seconds) induced in groups of Swiss Webster mice (10/group, 18-20 g) by the intraperitoneal injection of hexobarbital (100 mg/kg, I.P.). 2. Effect of Plasma Glucose in Rats Groups of 5-10 male Sprague-Dawleyrats (17-0-210 g) were orally dosed with the test compound or the vehicle. Three hours after dosing, the rats were sacrificed by decapitation and blood was collected for plasma glucose evaluation. 3. Effect of Inducing Emesis in Dogs Female beagle dogs (6-10 kg) were randomly selected for intravenous dosing with the test compound. Each dose of the test compounds was given to either two or four dogs. Immediately after the injection, the dogs were observed for emesis for a period of up to one hour. Certain of the compounds possess differentiated levels of effectiveness as antisecretory or antimotility agents when administered in generally used tests in laboratory animals which tests are known to correlate to human application. The following test is utilized in esta¬ blishing the antisecretory activity of the triazine derivatives. Inhibition of Gastric Acid Secretion in the Rat The method used has been reported by Shay. Male Sprague-Dawley rats (140-160 g) were fasted 24 hours prior to the test. The rats were allowed water ad libitum only during the fasting period. One hour before pyloric ligation, the rats (5/group) were given either the test compound, atropine sulfate or the vehicle. The compounds were prepared in methylcellulose. Pyloric ligation was performed in the rats under sodium methohexital anesthesia. Four hours after pyloric ligation the rats were sacrificed by cervical dislocation, the stomachs were removed, and the gastric contents were assayed for volume, titratable acidity, and titratable acid output (TAO) . A 1 ml aliquot of the gastric contents was titrated with 0.1 N NaOH to pH 7.0 for titratable acidity. The percent of inhibition was calculated according to the formula: Mean control - mean treated X 100 Mean control In general, compounds of Formula I are indicated for use as pharmacotherapeutic agent in a wide variety of mammalian conditions which require relief of symptoms or altering the action of the gastrointestinal or neuro-mus- cular systems. These compounds when used for example, as anti-diarrheal, antisecretory or antispasmodic agents, are effective for these purposes when administered orally and/or parenterally. The term "parenteral" as used herein includes intravenous, intramuscular, interperato- neal and the like injection or infusion techniques. The dosage regimens in carrying out the pharmaco¬ therapeutic methods utilizing the triazin-2-ones and triazin-2-thiones of this invention are those which insure maximum therapeutic response until improvement is obtained and thereafter the minimum effective level which gives relief. Thus, in general, the dosages are those that are therapeutically effective in the treatment of diarrhea and related gastrointestinal disorders. In general, the oral daily dose can be between about 0.1 g/kg and 70 mg/kg (preferably in the range of 0.5-50 mg/kg/day) , bearing in mind, of course, that in selecting the approprate dosage in any specific case, consideration must be given to the patient's weight, general health, age, and other factors which may influence response to the drug. Compositions intended for oral use may be prepared according to any method known to the art for the manufac¬ ture of pharmaceutical compositions and such compositions may contain one or more agents selected from the group consisting of sweetening agents, flavoring agents, coloring agents and preserving agents, in order to provide a phar¬ maceutically elegant and palatable preparation. Orally, they may be administered in tablets, aqueous or oily suspensions, dispersible powders or granules, emulsions, hard or soft capsules, or syrups or elixers. Tablets which contain the active ingredient in admixture with non-toxic pharmaceutically acceptable excipients are suitable for the manufacture of tablets. These excipients may be, for example, inert diluents, for example ' , calcium carbonate, sodium carbonate, lactose, calcium phosphate or sodium phosphate; granulating and distintegrating agents, for example, maize starch or alginic acid; binding agents, for example, starch, gelatin or acacia; and lubricating agents, for example, magnesium stearate, stearic acid or talc. The tablets may be uncoated or they may be coated by known techniques to delay disintg- gration and absorption. Formulations for oral use may also be presented as hard gelatin capsules wherein the active ingredient is mixed with an inert solid diluent, for example, calcium carbonate, calcium phosphate or kaolin, or as soft gelatin capsules wherein the active ingredient is mixed with an oil medium, for example, arachis oil, liquid paraffin or olive oil. Aqueous solutions containing the active substance and similar compositions formulated for ease of adminis- tration depending upon the particular therapeutic or prophylactic objective form a separate development with respect to the active compound disclosed herein. Excipients suitable for aqueous suspensions, may be employed if desired. These excipients are suspending agents, for example, sodium carboxymethyl-cellulose, methyl-cellulose, hydroxypropylmethyl-cellulose, sodium alginate, polyvinylpyrrolidine, gum tragacanth and gum acacia; dispersing or wetting agents may be a naturally occurring phosphatide, for example, lecithin; or condensation products of an alkylene oxide with fatty acids, for example, polyoxyethylene stearate; or conden¬ sation products of ethylene oxide with long-chain aliphatic alcohols, for example, heptadecaethyleneoxy- cetanol; or condensation products of ethylene oxide with partial esters derived from fatty acids and a hexitol, for example, polyoxyethylene sorbitol mono-oleate; or condensation products of ethylene oxide with partial esters derived from fatty acids and hexitol anhydrides, for example polyoxyethylene sorbitan monoleate. The said aqueous suspensions may also contain one or more preserva¬ tives, for example, ethyl, or n-propyl, p-hydroxy benzoate, one or more coloring agents, one or more flavoring agents, and one or more sweetening agents, such as sucrose. Oily suspensions may be formulated by suspending the active ingredient in a vegetable oil, for example, arachis oil, olive oil, sesame oil or coconutoil, or in a mineral oil, such as liquid paraffin. The oily suspen¬ sions may contain a thickening agent, for example, beeswax, hard paraffin or cetyl alcohol. Sweetening agents, such as those set forth above, and flavoring agents may be added to provide a palatable oral preparation. These com¬ positions may be preserved by the addition of an anti- oxidant such as ascorbic acid. * URE Dispersible powders and granules suitable for prepa¬ ration of an aqueous suspension by the addition of water provide the active ingredient in admixture with a dis¬ persing or wetting agent, suspending or wetting agents and suspending agents are exemplified by those already mentioned above. Additional excipients, for example, sweetening, flavoring and coloring agents, may also be present. The compounds of this invention may also be in the form of oil-in-water emulsions. The oily phase may be a vegetable oil, for example, olive oil or arachis oils, or a mineral oil, for example, liquid paraffin or mixtures of these. Suitable emulsifying agents may be naturally- occurring gums, for example, gum acacia or gum tragacanth, naturally-occurring phosphatides, for example, soya, bean lecithin, and esters or partial esters derived from fatty acids and hexitol anhydrides, for example, sorbitan mono-oleage. The emulsions may also contain sweetening and flavoring agents. Syrups and elixirs may be formulated with sweetening agents, for example, glycerol, sorbitoi or sucrose. Such formulations may also contain a demulcent, a preservative and flavoring and coloring agents. The pharmaceutical compositions may be in the form of a sterile i jectionable preparation, for example, as a sterile injectable aqueous suspension. This suspension may be formulated according to the known art using those suitable dispersing or wetting agents and suspending agents which have been mentioned above. The sterile injectable preparation may also be a sterile injectable solution or suspension in a nontoxic parenterally-acceptable diluent or solvent, for example, as an aqueous solution buffered to a pH of 4.0 to 7.0 and made isotonic with scdiu-ϊ. chloride. Further, the active triazine may be administered alone or in admixture with other agents having the same or different pharmacological properties. Further, these compounds may be tableted or otherwise formulated for oral use so that for every 100 parts by weight of the composition, there are present between 5 and 95 parts by weight of the active ingredient. The dosage unit form will generally contain between about 1 g. and about 500 mg. of the active ingredients of this invention. The preferred unit dose is be.tween about 10 g. and about 100 mg. The compositions may be taken 1-8 times daily depending on the dosage unit required. Parenteral administration'may be carried out using comparative dosages taken from the oral compositions. In general, the parenteral dosage will be less than the oral dose and normally within the range of 1/2 to 1/10 the oral dose but, of course, this would depend on the absorption characteristics of the compound employed. Dosages would be in the customary manner; however, in general, parenteral administration may be carried out neat or the compound may be utilized with a sterile vehicle as mentioned above. Dosage unit forms between 1 mg. and 500 mg. and preferably in the range of 10 mg. and 100 mg. are useful. The daily parenteral dose would be between 0.1 mg/Kg/day and 70 mg/Kg/day and preferably in the range of 0.5 g/Kg and 50 mg/Kg/day. The compounds of this invention are also useful as veterinary medicines. In particular, these compounds are useful in the treatment of animal scours, particularly in food animals. When administered in suitable formula¬ tions, for example, as additives to food or water, these compounds prevent or relieve scours in lambs, calves, piglets and fowl. - UREAU OMPI_

Claims: CLAIMS A compound of the formula wherein: n is 1 to 3; X is oxygen or sulfur; R j _ is a 5 or 6 membered heterocycle or a 5 or 6 membered heterocycle in which one or more of the hydrogens on the ring is replaced by the same or different substituents including halo, lower alkyl, halo lower alkyl, nitro, amino, acylamino, hydroxy, lower alkoxy, aryl-lower alkoxy, acyloxy, cyano, halo-lower alkoxy, or lower alkyl sulfonyl; R2 is hydrogen or lower alkyl; and and 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkyl amino, 'aryl or aryl-lower alkyl, lower alkoxy, phenoxy, a 5 or 6 membered heterocycle or a lower alkyl substituted 5 or 6 membered heterocycle or R 3 and R4 together with the nitrogen to which they are attached form a 3 to 7 membered heterocyclic ring, selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, azepinyl, piperazinyl, thiamorpholinyl, trimethylenetri- aminyl, ethyleneiminyl, and morpholinyl; and wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkyl acyla ino, lower alkyl acyloxy, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkanoyl, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and 5 or 6 membered heterocycle means a heterocyclic substi- tuent selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl; and the nontoxic pharmaceutically acceptable salts thereof. 2. A compound of the formula wherein X is oxygen or sulfur; R-, is pyridyl, thiophenyl or furyl; or pyridyl, thiophenyl or furyl in which one or more of the ring hydrogens are substituted by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; R 2 is hydrogen or lower alkyl; and R3 and R4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halo-lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, phenoxy-lower alkyl, di-lower alkyl-amino-lower alkyl or R3 and R4 together with the nitrogen to which they are attached form a 5 or 6 membered nitrogen heterocycle selec¬ ted from the group consisting of oxazolidinyl, thiazoli- ' dinyl, pyrazolidinyl, imidazolidinyl, piperidyl, pipera- zinyl, thiamorpholinyl, and morpholinyl; and the pharma¬ ceutically 7 acceptable nontoxic salts thereof. A compound of the formula where n: n is 1 to 3; R2 is hydrogen or lower alkyl; R 3 and RJ are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkylamino, aryl or aryl-lower alkyl, lower alkoxy, phenoxy and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, piperidyl and morpholinyl, or R 3 and R, together with the nitrogen to which they are attached f.orm a 3 to 7 membered ring selected from the group con¬ sisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, i idazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; and Re, Rg, R and Rg are each independently selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfony1; and wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same of different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkyl acylamino, lower alkyl acyloxy, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkanoyl, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and the nontoxic pharmaceutically acceptable salts thereof. URJ 4. A compound according to Claim 1, 2 or 3 wherein X is oxygen. 5. A compound according to Claim 3 wherein each of Rg, R and g is hydrogen; and the nontoxic phar aceuti- cally acceptable salts thereof. 6. A compound according to Claim 1, 2, 3 or 5 wherein R 3 is hydrogen; and the nontoxic pharmaceutically acceptable salts thereof. 7. A compound according to Claim 3 or 5 wherein Rr is halo, lower alkyl, lower alkoxy, or halo-lower alkyl; and the nontoxic pharmaceutically acceptable salts thereof. 8. A compound of the formula wherein: n is 1 to 3; R2 is hydrogen or lower alkyl; R3 and R4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cycloloweralkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy lower alkyl, phenoxy lower alkyl, diloweralkylamino, aryl or aryl lower alkyl, lower alkoxy, and phenoxy, and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazciyl, f ryl, thienyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl, or R 3 and R, together with the nitrogen to which they are attached form a 3 to 7 membered ring selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazoli- dinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpho- linyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; R5, Rg, Ry and R are each independently selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl, acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; and wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkyl acylamino, lower alkyl acyloxy, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkanoyl, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and the nontoxic pharmaceutically acceptable salts thereof. 9. A compound according to Claim 8 wherein R is hydrogen; and the nontoxic pharmaceutically acceptable salts thereof. 10. A compound according to Claim 9 wherein R 2 is hydrogen and 4 is hydrogen, lower alkyl, hydroxyl or lower alkoxy; and the nontoxic pharmaceutically acceptable salts thereof. 11. A compound according to Claim 10 wherein 5 and R 8 are each independently lower alkyl, lower alkoxy, halo, or halo-lower alkyl. wherein : n is 1 to 3 ; R 2 is hydrogen or lower alkyl; R3 and R4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cycloloweralkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy lower alkyl, phenoxy lower alkyl, diloweralkylamino, aryl or aryl lower alkyl, lower alkoxy, and phenoxy, and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, i idazolyl, furyl, thi- enyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl, or R3 and R4 together with the nitrogen to which they are attached form a 3 to 7 membered ring selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazoli- dinyl, imidazolidinyl, piperidyl, piperazinyl, thia orpho- linyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; R 5' R 6' R 7 an ^ R 8 are eac ^ independently selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl, acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; and wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkyl acylamino, lower alkyl acyloxy, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkanoyl, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and the nontoxic pharmaceutically acceptable salts thereof. 13. A compound according to Claim 12 wherein R_ is hydrogen; and the nontoxic pharmaceutically acceptable salts thereof. 14. A compound according to Claim 13 wherein R 2 is hydrogen and R^ is hydrogen, lower alkyl, hydroxyl or lower alkoxy; and the nontoxic pharmaceutically acceptable salts thereof. 15. A compound according to Claim 14 wherein R^ and Rg are each independently lower alkyl, lower alkoxy, halo, or halo-lower alkyl. 16. A compound of the formul .a wherein: n is 1 to 3 ; R 2 is hydrogen or lower alkyl; R3 and R^ are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl-, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkylamino, aryl or aryl-lower alkyl, lower alkoxy, phenoxy and 5 or i> membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, i idazolyl, furyl, thienyl, oxazolyl , piperidyl and morpholinyl, or R 3 and R^ form a 3 to 7 membered ring selected from the group consist¬ ing of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyi, and morpholinyl; and R 5' R 6' R 7 anc ^ R 8 are eac ^ independently selected from the ϋi group consisting of hydrogen, lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; and wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkyl acylamino, lower alkyl acyloxy, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkanoyl, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and the nontoxic pharmaceutically acceptable salts thereof. 17. A compound according to Claim 16 wherein R-, is hydrogen; and the nontoxic pharmaceutically acceptable salts thereof. 18. A compound according to Claim 15 wherein R>- is halo, lower alkyl, lower alkoxy, or halo-lower alkyl; and the nontoxic pharmaceutically acceptable salts thereof. 19. 1- (2'-pyridylmethyl)-4-methylamino-l,2-dihydro- l,3,5-triazin-2-one; and the non-toxic pharmaceutically acceptable salts thereof. 20. 1- (2*-pyridylmethyl)-4-amino-l,2-dihydro-l,3,5- triazin-2-one; and the non-toxic pharmaceutically acceptable salts thereof. 21. A process for the preparation of a compound according to the Formula I: H 2 C = = N / \ R 3 R l- (CH 2 } n "N C- N \ C '/ .N / which comprises reacting under cyclization conditions an activated methylidene compound and an amidinourea compound of Formula II X NH R-, R 1 -(CH 2 ) n -C f!-NH-C f!-N / 3 II R 4 wherein: n is 1 to 3; X is oxygen or sulfur; R- j _ is a 5 or 6 membered heterocycle or a substituted 5 or 6 membered heterocycle; R 2 is hydrogen or lower alkyl; and R3 and R4 are each independently' selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkyl amino, aryl or aryl-lower alkyl, lower alkoxy, phenoxy, a 5 or 6 membered heterocycle or a lower alkyl substituted 5 or 6 membered heterocycle or R3 and together with the nitrogen to which they are attached form a 3 to 7 membered heterocyclic ring, selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; and wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkyl acylamino, lower alkyl acyloxy, hydroxy, lower alkoxy, phenyl-lower alkoxy, lover alkanoyl, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and 5 or 6 membered heterocycle means a heterocyclic substitu¬ ent selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl; and the nontoxic pharmaceutically acceptable salts thereof. 22. A process according to Claim 21, wherein the activated methylidene compound is a dialkylacetal of a di-alkyl-lower carboxylic acid amide or the reaction product of a di-alkyl-lower carboxylic acid acid" and an alkylating agent. 23. A process according to Claim 21, wherein the activated methylidene compound is a dialkylacetal of a di-alkyl-lower carboxylic acid amide in the presence of hydrogen ion. IJ TR E T / " OMPI

Inventors: DODSON STUART ALAN, DOUGLAS GEORGE HENRY, STUDT WILLIAM LYON, WON CHONG MIN, ZALIPSKY JEROME JAROSLAW
Applicants: RORER INT OVERSEAS, RORER INT OVERSEAS INC
Application year: 1982
Main classification: C07D251
IPC codes: C07D251, C07D401, C07D403, C07D405, C07D409, C07D413, C07D417, C07D521