Halogen Or Acyclic Nitrogen Bonded Directly To The -c(=x)- Group Patents (Class 544/390)
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Patent number: 4810725Abstract: 1-Aryloxy-3-(substituted aminoalkylamino)-2-propanols and pharmaceutically acceptable salts thereof have .beta.-adrenergic blocking activity with some cardioselectivity and hence are useful as anti-hypertensive, antianginal, antiarrhythmic and cardioprotective agents and in the treatment of elevated intraocular pressure such as glaucoma.Type: GrantFiled: October 14, 1986Date of Patent: March 7, 1989Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Gerald S. Ponticello, Sandor L. Varga
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Patent number: 4782071Abstract: Certain tetrasubstituted alkyl, aryl, pyridinyl, piperidinyl, and piperazinyl urea compounds stimulate the release of acetylcholine and are thus useful analgesic agents for alleviating pain or as cholinergic agents which are useful for the amelioration of the symptoms of cognitive decline in the elderly.These compounds have the general formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.4 are phenyl or substituted phenyl, and R.sub.3 is pyridinyl.Pharmaceutical compositions including these compounds as well as methods for the preparation of the compounds are also disclosed.Type: GrantFiled: November 3, 1986Date of Patent: November 1, 1988Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, David M. Lustgarten, Walter H. Moos, Anthony J. Thomas
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Patent number: 4778915Abstract: The invention relates to fluoroacrylic monomers of formula: ##STR1## in which R.sub.f denotes a perfluoroalkyl radical, R is hydrogen or a methyl radical, R' denotes an alkyl or cycloalkyl radical, or --NR'-- denotes a 1, 4-piperazinylene radical, W and Z denote divalent connecting groups, Q is oxygen or sulphur or an --NR"-- group, R" denoting hydrogen an alkyl radical, and A is a C.sub.2 or C.sub.3 alkylene group. The polymers (homo- or copolymers) derived from these monomers may be used for the water-repellency and oil-repellency treatment of various substrates, particularly leather.Type: GrantFiled: October 16, 1986Date of Patent: October 18, 1988Assignee: AtochemInventors: Marie-Jose Lina, Andre Dessaint
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Patent number: 4778789Abstract: Novel compounds of formula (I), wherein R.sub.1 is selected from hydrogen, halogen; or trifluoromethyl; X is oxygen or sulfur; R.sub.2 and R.sub.3 are the same or different and selected from hydrogen or lower alkyl; m is 2 or 3; Y is oxygen or sulphur; Z is selected from: --NR.sub.4 R.sub.5, formulae (II), (III) or (IV), wherein R.sub.4 and R.sub.5 are the same or different and selected from hydrogen, alkyl, cycloalkyl, cycloalkyl-alkyl, hydroxy-alkyl, alkoxyalkyl or alkanoyloxyalkyl, phenyl or phenyl-alkyl, wherein the phenyl groups may be unsubstituted or monosubstituted with halogen or CF.sub.3 ; n is 0, 1, 2 or 3; R.sub.6 and R.sub.7 are the same or different and selected from hydrogen, lower alkyl, hydroxy, lower alkoxy or lower alkanoyloxy; p is 2 or 3; R.sub.8 and R.sub.9 are the same or different and selected from hydrogen or lower alkyl; R.sub.10 is hydrogen, lower alkyl or lower alkanoyl. The new compounds can be used for treating mental disorders.Type: GrantFiled: November 26, 1986Date of Patent: October 18, 1988Assignee: Aktiebolaget LeoInventors: Tomas Fex, Knut G. Olsson, Aina L. Abramo, Erik G. Christensson
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Patent number: 4766116Abstract: A diaryl butyric acid derivative having the general formula: ##STR1## wherein R.sup.1 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an acyl group having 2 to 4 carbon atoms; R.sup.2 represents an alkyl group having 1 to 3 carbon atoms; andX represents a variety of substituents.This diaryl butyric acid derivative or the pharmaceutically acceptable salt thereof can be prepared by reacting a benzoxepin derivative having the general formula: ##STR2## wherein R.sup.2 is the same as defined above with an amine or alcohol derivative having the general formula;X--Hwherein X is the same as defined above in the presence of an acid catalyst at room temperature or at an elevated temperature and, optionally, further reading the reaction product with an alkylation agent having 1 to 3 carbon atoms or an acylation agent having 2 to 4 carbon atoms.Type: GrantFiled: December 19, 1985Date of Patent: August 23, 1988Assignee: Suntory LimitedInventors: Toshio Tatsuoka, Kenji Suzuki, Kayoko Imao, Kunihiro Sumoto
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Patent number: 4762829Abstract: A novel polyprenyl compound such as a polyprenyl carboxylic acid amide is disclosed. It has antithrombic and antiplatelet aggregation activity.Type: GrantFiled: October 23, 1986Date of Patent: August 9, 1988Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Tohru Fujimori, Koukichi Harada, Shinichi Kitamura
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Patent number: 4719221Abstract: A class of novel thiosemiarbazones has been found to be active against a number of protozoa which cause serious diseases, mainly in the tropical areas of the world.Type: GrantFiled: July 27, 1984Date of Patent: January 12, 1988Assignee: Burroughs Wellcome Co.Inventor: Jr. Morrison
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Patent number: 4708954Abstract: Pharmaceutical compositions containing an oxaluric acid derivative of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2, which may be the same or different, is hydrogen; an alkyl group or a cycloalkyl group; or R.sub.1 and R.sub.2 are joined to form a heterocyclic ring with the nitrogen atom to which they are both attached; and R.sub.3 is hydrogen or an alkyl group. These compounds have excellent hypoglycemic effects with low toxcicity and safety.Type: GrantFiled: February 7, 1986Date of Patent: November 24, 1987Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventors: Kazuharu Ienaga, Ko Nakamura, Akira Ishii
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Patent number: 4686220Abstract: This disclosure describes certain substituted piperazine-1,4-naphthalenediones useful as anti-asthmatic agents.Type: GrantFiled: December 19, 1985Date of Patent: August 11, 1987Assignee: American Cyanamid CompanyInventors: Jeffrey B. Medwid, Lawrence W. Torley, Andrew S. Tomcufcik
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Patent number: 4684639Abstract: A compound having the partial structure (I) ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and each is hydrogen or a group --COR.sup.5 or --CO--OR.sup.5 wherein R.sup.5 represents an optionally substituted hydrocarbon group; R.sup.3 is halogen and R.sup.4 is hydrogen, methoxy, hydroxymethyl or formamido.These compounds are suitably bicyclic .beta.-lactam antibiotics.Type: GrantFiled: July 5, 1984Date of Patent: August 4, 1987Assignee: Beecham GroupInventors: George Burton, Desmond J. Best
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Patent number: 4666911Abstract: An analgesic compositon containing as active ingredient an allophanoylpiperazine compound represented by the general formula ##STR1## wherein R.sup.1 represents a lower alkyl group or phenyl group; R.sup.2 and R.sup.3 each represents a hydrogen atom or a lower alkyl group; and R.sup.4 represents a phenyl group or a substituted phenyl group having as substituent a halogen atom or methyl, trifluoromethyl, hydroxyl, methoxy, methylenedioxy, nitro, or carboxyl group; pyridyl group, pyrimidyl group, thiazolyl group, benzyl group, cinnamyl group, cyclohexyl group, a lower alkyl group, a substituted lower alkyl group having chlorine atom or hydroxyl group as substituent; or a lower alkenyl group.Type: GrantFiled: July 8, 1981Date of Patent: May 19, 1987Assignee: Taiho Pharmaceutical Company LimitedInventors: Hajime Fujimura, Yasuzo Hiramatu, Takahiro Yabuuchi, Masakatu Hisaki, Katsuo Takikawa, Takaji Honna, Hidekazu Miyake, Makoto Kajitani
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Patent number: 4612313Abstract: The present invention provides phenylacetonitrile derivatives of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5, which can be the same or different, are hydrogen or haolgen atoms or alkyl, alkoxy, nitro, amino or acylamino radicals and two adjacent substituents can together also form a methylenedioxy or ethylenedioxy radical, A is a radical of the general formula: ##STR2## in which R.sub.6 is a straight-chained, cyclic or branched, saturated or unsaturated alkyl radical containing 2 to 12 carbon atoms, R.sub.Type: GrantFiled: September 10, 1985Date of Patent: September 16, 1986Assignee: Boehringer Mannheim GmbHInventors: Herbert Leinert, Wolfgang Kampe, Klaus Strein, Bernd Muller-Beckmann, Wolfgang Bartsch
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Patent number: 4599338Abstract: Xanthine compounds of the formula: ##STR1## in which: R.sub.1 is hydrogen or (C.sub.1 -C.sub.5) alkyl;R.sub.2 is hydrogen, (C.sub.1 -C.sub.5) alkyl optionally having a double bond, or benzyl;R.sub.3 is hydrogen or methyl;A is (CH.sub.2).sub.n, in which n is an integer from 1 to 4, optionally substituted, when n is higher than 1, by hydroxy;X is nitrogen or ##STR2## and the substituents R are each (C.sub.1 -C.sub.5) alkyl or they form together a polymethylene chain from C.sub.4 to C.sub.6, optionally containing an oxygen or a sulfur atom.These compounds and physiologically tolerable acid addition salts thereof may be used as medicines especially in the treatment of migraine and asthenia.Type: GrantFiled: January 16, 1985Date of Patent: July 8, 1986Assignee: Adir, S.A.R.L.Inventors: Gilbert Regnier, Claude Guillonneau, Jacques Duhault, Francois Roman
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Patent number: 4599419Abstract: (3-Aminopropoxy)bibenzyl derivatives are prepared and found useful as pharmaceutical agents, particularly as inhibitors of platelet aggregation.Type: GrantFiled: July 9, 1984Date of Patent: July 8, 1986Assignee: Mitsubishi Chemical Industries, Inc.Inventors: Ryoji Kikumoto, Harukazu Fukami, Hiroto Hara, Kunihiro Ninomiya, Mamoru Sugano
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Patent number: 4582855Abstract: Novel compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted aromatic or heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 momoered heterocyclic group; and the pharmaceutically acceptable salts thereof. These compounds exhibit .beta.-adrenergic blocking activity and are also useful in the treatment of glaucoma.Type: GrantFiled: November 12, 1981Date of Patent: April 15, 1986Assignee: American Hospital Supply CorporationInventors: Sheung T. Kam, William L. Matier
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Patent number: 4510142Abstract: This invention relates to new derivatives of biphenyl alkyl carboxylates, to a process for the preparation thereof and the use thereof as medicaments.The new derivatives according to the present invention correspond to general formula (I): ##STR1## wherein X represents a hydrogen atom or a halogen atom,R represents a hydrogen atom or an alkyl group, andR.sub.1 represents the following groups: ##STR2## These compounds will notably be used in the treatment of obstinate pains and inflammatory syndromes.Type: GrantFiled: October 12, 1982Date of Patent: April 9, 1985Assignee: Pierre Fabre S.A.Inventors: Henry Cousse, Gilbert Mouzin, Jean-Pierre Tarayre, Jean-Pierre Rieu
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Patent number: 4479952Abstract: Monosubstituted piperazines of the formula: ##STR1## in which: A is --(CH.sub.2).sub.n --, n being 1, 2 or 3, or ##STR2## R being alkyl up to C.sub.5 inclusive, trifluoromethyl, phenyl, halophenyl, lower-alkylphenyl, lower-alkoxyphenyl or trifluoromethylphenyl andAr is phenyl, halophenyl, lower-alkylphenyl, lower-alkoxyphenyl, methylenedioxyphenyl, hydroxyphenyl, or ##STR3## in which X is a single bond, oxygen, sulfur or carbonyl and Y is hydrogen, halogen, lower alkyl or lower alkoxy.These compounds and their physiologically tolerable acid addition salts thereof may be used as medicines especially in the treatment of inflammation with immunological component.Type: GrantFiled: April 9, 1979Date of Patent: October 30, 1984Assignee: Science Union Et CieInventors: Gilbert R/e/ gnier, Jacques Bur/e/
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Patent number: 4446133Abstract: The present invention relates to a novel piperazine compound represented by the following general formula (I): ##STR1## wherein X stands for a hydrogen or halogen atom, an alkoxy, carboxy or alkoxycarbonyl group or a group R.sup.3 CO-- in which R.sup.3 stands for an alkyl group having 1 to 4 carbon atoms, R.sup.1 stands for a hydrogen atom or an alkyl group, and R.sup.2 stands for a hydrogen atom or an alkyl group.These compounds are valuable as immunopotentiators, such as for the treatment of chronic rheumatoid arthritis and other diseases accompanied by reduction or abnormal change of the immune function.Type: GrantFiled: February 13, 1981Date of Patent: May 1, 1984Assignee: Misuitoatsu Chemicals, Inc.Inventors: Yutaka Okazaki, Hiroshi Tokuda, Shiyoichiro Miyahara, Yoshitsugu Yamada
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Patent number: 4443477Abstract: The invention provides sulphonamides of the formula ##STR1## wherein R is a hydrogen atom or a lower alkyl radical;R.sub.1 is alkyl, aryl, aralkyl or aralkenyl, the aryl moiety of which in each case can be optionally substituted one or more times by hydroxyl, halogen, trifluoromethyl, lower alkyl or alkoxy or by acyl, carboxy or alkoxycarbonyl;n is 1, 2 or 3; andW is a valence bond or a divalent aliphatic hydrocarbon linkageand the physiologically acceptable salts, esters and amides of such compound. These compounds have excellent pharmacological lipid depressing activity and inhibit thrombocyte aggregation.Type: GrantFiled: July 7, 1982Date of Patent: April 17, 1984Assignee: Boehringer Mannheim GmbHInventors: Ernst-Christian Witte, Hans P. Wolfe, Karlheinz Stegmeier, Egon Roesch
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Patent number: 4435397Abstract: 4-(3-Aryloxy-2-hydroxypropyl)piperazines bearing a carbamyl group in the 1-position are .beta.-adrenergic blockers. A typical example is 1-carbamyl-4-{3-[2-allyl-3-(2-carbethoxyaminoethyl)phenoxy]-2-hydroxypropy l}piperazine.Type: GrantFiled: March 26, 1981Date of Patent: March 6, 1984Assignee: Nippon Shinyaku Co., Ltd.Inventors: Shingo Matsumura, Hiroshi Enomoto, Yoshiaki Aoyagi, Haruo Tanaka
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Patent number: 4418209Abstract: This invention describes a new class of 1-amidino-3-phenylthiourea and N'-phenylamidinothiourea compounds wherein the phenyl group is ortho substituted, and processes for their preparation. The phenylamidinothiourea compounds may be incorporated into pharmaceutical preparations which are useful for producing anti-ulcerogenic, antisecretory, antispasmodic, antihypertensive, anti-arrhythmic, anesthetic, antidiarrheal and antiparasitic action.Type: GrantFiled: December 21, 1981Date of Patent: November 29, 1983Assignee: William H. Rorer, Inc.Inventors: George H. Douglas, Julius Diamond, William L. Studt, Stuart A. Dodson
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Patent number: 4374990Abstract: A compound having the general formula or an acid addition salt thereof ##STR1## in which formula R.sub.1 is selected from the group consisting of(A) an at least mononuclear heterocyclic group having 4 to 10 carbon atoms in the ring system bound to the group ##STR2## through a carbon atom and containing at least one oxygen, nitrogen or sulphur atom,(B) substitution products of (A) containing at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxy, alkoxy of 1 to 3 carbon atoms, unsubstituted amino, amino substituted by up to two alkyl groups each having 1 to 3 carbon atoms and alkyl groups having 1 to 6 carbon atoms,X is oxygen, sulphur or an NH-group,Y is an alkylene group having 1 to 3 carbon atoms in the chain, or an alkylene group having 1 to 3 carbon atoms in the chain substituted by (a) up to 3 alkyl groups each having up to 3 carbon atoms and a total of not more than 8 carbon atoms, or (b) substituted by one or two phenyl groups,R.sub.Type: GrantFiled: October 26, 1979Date of Patent: February 22, 1983Assignee: Hoechst AktiengesellschaftInventors: Rolf-Ortwin Weber, Alfons Soder, Istvan Boksay
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Patent number: 4352891Abstract: There are provided a palatable anthelmintic resinate composition having improved storage and handling characteristics comprising from 2% to 5% of a resinate N,N-dialkylpiperazine carboxamide, from 0% to 7% of a resinated styryl pyridinium compound, from 18% to 60% of dessicated liver, from 20 to 47% of dry whey, and from 1% to 10% of polyvinylpyriolidone, carboxypolymethylene or mixtures thereof, said percentages being all by weight, and a method for preparing the same.Type: GrantFiled: October 14, 1980Date of Patent: October 5, 1982Assignee: American Cyanamid Co.Inventor: James M. Quinlan
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Patent number: 4329344Abstract: This invention provides compounds, having major tranquilizing activity, of the formula (II): ##STR1## wherein R.sub.1 is a phenyl group optionally substituted by a fluorine, chlorine or bromine atom or an alkyl or alkoxyl group of up to 3 carbon atoms; R.sub.2 is a hydrogen atom or an alkyl group of up to 4 carbon atoms; R.sub.3 is a hydrogen atom or an amino group, a nitro group or a group of the formula NHCOR.sub.4 or NHCO.sub.2 R.sub.4 where R.sub.4 is an alkyl group of up to 4 carbon atoms optionally substituted by one, two or three chlorine atoms or by three fluorine atoms attached to the same carbon atom; n is 0, 1 or 2; and X is a group of the sub-formula (a), (b), (c) or (d): ##STR2## wherein R.sub.5 is an alkyl group of up to 4 carbon atoms; or a N-oxide thereof of the nitrogen atom to which the CHR.sub.2 --(CH.sub.2).sub.n --R.sub.1 moiety is attached; and salts thereof; pharmaceutical compositions containing them; processes for their preparation; and intermediates useful in said process.Type: GrantFiled: May 12, 1980Date of Patent: May 11, 1982Assignee: Beecham Group LimitedInventor: Michael S. Hadley
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Patent number: 4323388Abstract: There have been produced novel cyanoalkyl-phenylureas which have herbicidal activity and which exhibit good selectivity in various crops of cultivated plants.Type: GrantFiled: March 3, 1981Date of Patent: April 6, 1982Assignee: Ciba-Geigy CorporationInventors: Georg Pissiotas, Dieter Durr, Otto Rohr, Alfons Lukaszczyk
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Patent number: 4312663Abstract: Cyclicacylaminoperfluoroalanesulfonanilides and agriculturally acceptable salts thereof are useful as herbicides and plant growth regulators.Type: GrantFiled: September 18, 1980Date of Patent: January 26, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventor: Ezzat A. Mikhail
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Patent number: 4308387Abstract: Compounds having the general formula ##STR1## as herein defined and pharmaceutically acceptable acid addition salts thereof. Pharmaceutical compositions containing said compounds. Methods of treatment of humans and animals by such compounds and compositions.Type: GrantFiled: October 18, 1979Date of Patent: December 29, 1981Assignee: AB FerrosanInventors: Anders K. K. Bjork, Knut G. Olsson, Aina L. Abramo, Erik G. Christensson
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Patent number: 4281188Abstract: This invention provides benzodiazepine derivatives of the general formula ##STR1## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a hydrogen atom or a lower alkyl group, R.sup.3 represents a halogen atom and R.sup.4 represents a hydrogen or halogen atom and either R.sup.5 represents a hydrogen atom or a lower alkyl group and R.sup.6 represents a lower alkyl, lower hydroxyalkyl or lower acyloxyalkyl group or R.sup.5 represents a hydrogen atom and R.sup.6 represents an aryl or lower aralkyl group or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached represent a 3-membered to 7-membered heterocycle which, when it is at least 5-membered, can contain as a ring member an oxygen or sulphur atom or a group of the formula >N--R.sup.7 in which R.sup.Type: GrantFiled: September 11, 1980Date of Patent: July 28, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Albert E. Fischli, Andre Szente
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Patent number: 4269838Abstract: 4-(3-Aryloxy-2-hydroxypropyl)piperazines bearing a carbamyl, N-alkyl or N,N-dialkylcarbamyl group in the 1-position are .beta.-adrenergic blockers. A typical example is 1-carbamyl-4-(3-phenoxy-2-hydroxypropyl)piperazine.Type: GrantFiled: October 23, 1979Date of Patent: May 26, 1981Assignee: Nippon Shinyaku Co. Ltd.Inventors: Shingo Matsumura, Hiroshi Enomoto, Yoshiaki Aoyagi, Haruo Tanaka
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Patent number: 4247549Abstract: Piperazine-1-carboxylic acid esters which are useful as antidepressants and as analgesics.Type: GrantFiled: December 27, 1978Date of Patent: January 27, 1981Assignee: ICI Americas Inc.Inventors: Cyrus J. Ohnmacht, Jeffrey B. Malick
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Patent number: 4243665Abstract: Compounds corresponding to the formula ##STR1## in which R' is a hydrogen atom or a methyl radical and R represents a radical ##STR2## in which Z is O, S, S.fwdarw.O, SO.sub.2 or NR.sub.1, in which R.sub.1 is a hydrogen atom or an alkyl, CONR.sub.2 R.sub.3, COOR.sub.2, COR.sub.2 or SO.sub.2 R.sub.2 radical, R.sub.2 and R.sub.3 each representing, independently of one another, a hydrogen atom, an alkyl radical having 1 to 4 carbon atoms, a phenyl radical or a CF.sub.3 radical, in the form of racemates or enantiomers if R' is CH.sub.3, and also, where appropriate, their addition salts with pharmaceutically acceptable acids.The compounds and salts are useful as anti-inflammatory agents, e.g. for treatment of arthritis. A process for preparing them and pharmaceutical compositions containing them are also claimed.Type: GrantFiled: November 21, 1978Date of Patent: January 6, 1981Assignee: SynthelaboInventors: Thomas A. Purcell, Braham Shroot, Daniel J. M. Galtier
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Patent number: 4239761Abstract: The present invention is related to new basically substituted ureas having the general Formula I ##STR1## and the pharmaceutically acceptable acid addition salts thereof which produce an improved antiviral activity against DNS- and RNS-viruses. The invention is further related to the treatment of humans or animals suffering from diseases caused by viruses by administering compositions containing such ureas or salts thereof as active agent.Type: GrantFiled: August 23, 1979Date of Patent: December 16, 1980Assignee: Asta-werke Aktiengesellschaft, Chemische FabrikInventors: Rolf Rebling, Gerhard Scheffler, Klaus Pressler, Klaus D. Schenk
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Patent number: 4091220Abstract: Novel N-benzylpiperazine derivatives of the general formula ##STR1## wherein R.sup.1 and R.sup.2 are same or different and each stands for a hydrogen atom or an acyl group; R.sup.3 stands for a hydrogen atom; a carbamoyl group, an acyl group which is unsubstituted or substituted by mercapto or morpholino, or an alkyl group which is unsubstituted or substituted by hydroxy, aryl or aminocarbonyl represented by the formula ##STR2## wherein each of R.sup.4 and R.sup.5 is a hydrogen atom, a lower alkyl group having 1 to 3 carbon atoms or a cyclohexyl group, or R.sup.4 and R.sup.5 form a morpholino or piperidino ring together with the nitrogen atom adjacent thereto, and X stands for a halogen atom, and pharmaceutically acceptable acid addition salts thereof. These compounds and salts thereof have respiratory tract fluid secretion stimulatory properties and are useful as medicines such as respiratory track fluid secretion stimulators.Type: GrantFiled: May 3, 1977Date of Patent: May 23, 1978Assignee: Takeda Chemical Industries, Ltd.Inventors: Toshihiro Ishiguro, Yasushi Sanno