Phenyl Or Naphthyl Bonded Directly To Ring Nitrogen Of The Piperazine Ring Patents (Class 544/392)
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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: 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: 4645862Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.3 each is benzyl or substituted with up to 3 methoxy groups, R.sub.2 is a hydrogen atom and (alkylene) is lower alkyl and the compounds are useful for controlling viral infections.Type: GrantFiled: April 15, 1985Date of Patent: February 24, 1987Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Yoshiyuki Tahara, Yasuhiro Komatsu, Hiroyasu Koyama, Reiko Kubota, Teruhito Yamaguchi, Toshihiro Takahashi
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Patent number: 4613598Abstract: A piperazine derivative according to the present invention has the following general formula [I]: ##STR1## wherein R.sup.1 is --OH, --OR.sup.3, --SR.sup.3, --SOR.sup.3 or --SO.sub.2 R.sup.3 wherein R.sup.3 is alkyl group having 1 to 3 carbon atoms;R.sup.2 is --SO.sub.2 NH.sub.2, --SO.sub.2 NHR.sup.4, --SO.sub.2 NR.sup.4 R.sup.5, --COOH, --COOR.sup.4, --CONH.sub.2, --CONHR.sup.4, --CONR.sup.4 R.sup.5, --NHCONH.sub.2, --NHCSNH.sub.2, --NHCONHR.sup.4, --NHCOR.sup.4 or --NHSO.sub.2 R.sup.4 wherein R.sup.4 and R.sup.5 are independently alkyl group having 1 to 3 carbon atoms; orR.sup.1 and R.sup.2 together with carbon atoms to which they are attached form ##STR2## Z is --CO-- or --CH(OH)--; Ar is pyridyl or substituted or unsubstituted phenyl; andn is an integer of 3 to 5.An acid addition salt of the piperazine derivative having the above formula [I] is included in the present invention.Type: GrantFiled: March 6, 1985Date of Patent: September 23, 1986Assignee: Mitsubishi Chemical Industries LimitedInventors: Harukazu Fukami, Shinya Inoue, Issei Nitta, Kenichiro Nakao, Ryoji Kikumoto
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Patent number: 4593027Abstract: 3-Aryl-7-chloro-3,4-dihydroacridine-1,9(2H,10H)-dione 1-oximes and 1-hydrazone derivatives of the formula I ##STR1## and their physiologically tolerated acid addition and ammonium salts are described, as is a process for their preparation. The new compounds are chemotherapeutic agents and are active against protozoa, especially malaria plasmodia.Type: GrantFiled: October 11, 1983Date of Patent: June 3, 1986Assignee: Hoechst AktiengesellschaftInventors: Erhardt Winklemann, Walter Durckheimer, Wolfgang Raether
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Patent number: 4590193Abstract: This invention relates to 3-(2-(4-phenylpiperazinylethyl)anilino)-isobenzofuranones, their method of preparation and their use in the treatment of conditions such as hypertension, and allergies.These compounds are characterized by the formula: ##STR1## in which R.sub.1 may be one or more substituents located at the ortho, meta, or para positions selected from the group of H, CH.sub.3, CF.sub.3, F, Cl and OCH.sub.3 ; R.sub.2 and R.sub.3 are the same or different and are H or OCH.sub.3. These compounds are in the form of free bases or their pharmaceutically safe salts. They can be obtained by a reaction between a 2-(phenylpiperazinylethyl) aniline and an aromatic aldehyde having an acid function at the ortho position of the carboxaldehyde function.These derivatives are useful for the treatment of hypertension and allergic conditions.Type: GrantFiled: July 27, 1983Date of Patent: May 20, 1986Assignee: Societe Cortial, S.A.Inventors: Marie-Helene Creuzet, Claude Feniou, Francoise Guichard, Gisele Prat, Henri Pontagnier
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Patent number: 4560686Abstract: Compounds of the formula ##STR1## (wherein R.sub.1 is a lower alkyl group, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxyl group, a trifluoromethyl group or a lower alkoxycarbonyl group; two adjacent groups of R.sub.2, R.sub.3 and R.sub.4 may combine to form a methylenedioxy group; n is an integer of 2 to 6) or salts thereof, are disclosed.These compounds are useful as agents for treating circulatory diseases because they have hypotensive action and are capable of increasing the cerebral blood flow, decreasing the heart rate and suppressing ventricular arrhythmia due to myocardial ischemia.Type: GrantFiled: September 14, 1983Date of Patent: December 24, 1985Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Hiroyuki Nagano, Mitiro Takagi, Noboru Kubodera, Isao Matsunaga, Hiroyuki Nabata, Yasuhiro Ohba, Kazushige Sakai, Shun-ichi Hata, Yasumi Uchida
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Patent number: 4518712Abstract: An analgesic composition containing as active ingredient a piperazine derivative represented by the general formula (1) ##STR1## wherein R.sub.1 represents a cyclopropylmethyl group, an isopropyl group or an allyl group and R.sub.2 represents a phenyl group having as substituent a halogen atom or a trifluoromethyl group.Type: GrantFiled: June 22, 1981Date of Patent: May 21, 1985Assignee: Taiho Pharmaceutical Company LimitedInventors: Hajime Fujimura, Yasuzo Hiramatsu, Tomio Yamazaki, Shozo Yamada, Takaji Honna
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Patent number: 4515793Abstract: A compound of the formula ##STR1## in which A is ##STR2## n is 1, 2 or 3, and R is phenyl optionally substituted with halogen, alkyl, phenyl, cyano, hydroxy, alkoxy, mercapto, sulfinyl, sulfonyl, amino, nitro, trifluoromethyl and/or naphthyl radicals; or a furan, thiophene, pyridine, benzofuran, dibenzothiophene or thianthrene radical,or a pharmacologically acceptable salt thereof, for treating schistosomiasis.Type: GrantFiled: July 27, 1983Date of Patent: May 7, 1985Assignee: Edna McConnell Clark FoundationInventors: Leslie M. Werbel, Norman Colbry, William Turner, Donald F. Worth
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Patent number: 4487721Abstract: The present invention is directed to a process for producing 2-amino-2-arylacetonitriles of general formula I: ##STR1## wherein R and R.sup.1 independently represent hydrogen, hydroxy, hydroxy(C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.6)alkyl, 2-furyl, 2-thienyl, 4-pyridinyl, 1-pyrrolydinyl, 1-piperidinyl, 4-morpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl, 4-phenylpiperazinyl, or phenyl which can optionally be substituted with from 1 to 3 substituents independently selected from (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy, or R and R.sup.1 independently represent a phenyl(C.sub.1 -C.sub.4)alkyl or a phenyl(C.sub.1 -C.sub.4)alkoxy group wherein the phenyl group can be either unsubstituted or substituted as above.An arylaldehyde derivative of formula II ##STR2## is reacted with chloroform in base and in the presence of ammonia to give the 2-amino-2-arylacetonitrile derivative.Type: GrantFiled: June 7, 1983Date of Patent: December 11, 1984Assignee: Gruppo Lepetit S.p.A.Inventor: Romeo Ciabatti
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Patent number: 4477664Abstract: A 1-(4-aminobenzyl)-2,3-dioxopiperazine derivative represented by the formula: ##STR1## and an acid addition salt thereof have excellent carcinostatic activity but a low toxicity. Therefore, said compounds are useful as medicines and also as intermediates.Type: GrantFiled: February 22, 1982Date of Patent: October 16, 1984Assignee: Toyama Chemical Co., Ltd.Inventors: Takako Hori, Chosaku Yoshida, Yasuo Kiba, Ryuko Takeno, Joji Nakano, Jun Nitta, Sumiko Kishimoto, Shohachi Murakami, Hisatsugu Tsuda, Isamu Saikawa
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Patent number: 4474783Abstract: A compound having the formula ##STR1## in which R is hydrogen or alkyl having 1 to 4 carbon atoms; R.sub.1 is hydrogen, alkyl having 1 to 5 carbon atoms, cycloalkylmethyl in which the cycloalkyl group has from 3 to 6 carbon atoms, 2-hydroxyethyl, alkoxycarbonyl in which the alkoxy group has 1 or 2 carbon atoms, 2-carboxypropyl, N-benzyl-2-carbamoyl propyl, phenyl, phenyl substituted by methoxy, trifluoromethyl or acetyl, benzyl, benzyl substituted by halogen, benzoyl, benzoyl substituted by three methoxy groups, 3,5-dimethoxy-4-acetoxy or 3,5-dimethoxy-4-ethoxycarbonyloxy, cinnamoyl, cinnamoyl in which the phenyl ring is substituted with trifluoromethyl or by one or more methoxy groups, phenoxyacetyl, phenoxyacetyl in which the phenyl ring is substituted with halogen or methoxy, and ##STR2## in which m is 2 or 3 and R.sub.2 and R.sub.Type: GrantFiled: September 25, 1981Date of Patent: October 2, 1984Assignee: InnotheraInventors: Max F. Robba, Michel E. Aurousseau
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Patent number: 4469694Abstract: 2-(1-Piperazinyl)-2,4,6-cycloheptatrien-1-one derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions of the derivatives are disclosed. The derivatives exhibit dopamine-receptor stimulating activity in a mammal and are useful for treating hyperprolactinemia, galactorrhea, amenorrhea, impotence, Parkinsonism, diabetes, acromegaly, hypertension and other central nervous system disorders.Type: GrantFiled: February 25, 1980Date of Patent: September 4, 1984Assignee: Ayerst, McKenna & Harrison Inc.Inventors: Jehan F. Bagli, Tibor Bogri, Katherine Voith
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Patent number: 4456756Abstract: Piperazinyl derivatives containing a spiro-2,4-thiazolidinedione heterocyclic component with relatively selective psychotropic properties are disclosed. The compound 2-[4-[4-(7,9-dioxo-6-thia-8-azaspiro[4.4]nonan-8-yl)butyl]-1-piperazinyl]p yridine-3-carbonitrile which has selective anti-psychotic activity constitutes a typical embodiment of the invention.Type: GrantFiled: August 3, 1981Date of Patent: June 26, 1984Assignee: Mead Johnson & CompanyInventors: Davis L. Temple, Jr., Richard E. Yeager
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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: 4438268Abstract: This invention relates to new nematic liquid crystal substances for electro-optical components.The object of this invention is to create substances for electro-optical components combining chemical and thermal stability with low melting and high clear points at low operational voltage, as well as to processes for their production.It has been found that new liquid-crystal trans-6-n-alkyl-decalin-2-carbonic acid ester of the general formula ##STR1## can be introduced into electro-optical components. These substances are produced by the catalytic high-pressure hydrogenation of 6-n-alkylnaphthalene-2-carbonic acids, separation of the trans-isomers by distillation, and esterification with the corresponding hydroxy compounds of the acyl chlorides obtained through reaction with thionyl chloride.Type: GrantFiled: September 14, 1981Date of Patent: March 20, 1984Inventors: Horst Zaschke, Wolfgang Schafer, Hans-Joachim Deutscher, Dietrich Demus, Gerhard Pelzl
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Patent number: 4421753Abstract: This disclosure describes novel 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-substituted-piperazines which are useful as hypotensive agents in mammals.Type: GrantFiled: March 22, 1982Date of Patent: December 20, 1983Assignee: American Cyanamid CompanyInventors: Andrew S. Tomcufcik, Walter E. Meyer, John P. Dusza
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Patent number: 4413006Abstract: A piperazine derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl (C.sub.1-8), alkyl (C.sub.1-4)-sulfonyl or an acyl group of the formula: R.sup.3 CO--(wherein R.sup.3 is hydrogen, alkyl (C.sub.1-7), halogenoalkyl (C.sub.1-4), alkoxy (C.sub.1-4)-carbonyl-alkyl (C.sub.1-4), cycloalkyl (C.sub.3-6), alkenyl (C.sub.2-5), alkoxy (C.sub.1-4), amino, alkyl (C.sub.1-4)-amino or anilino), R.sup.2 is hydrogen, alkyl (C.sub.1-4), alkoxy (C.sub.1-4)-carbonyl-alkyl (C.sub.1-4), carboxy-alkyl (C.sub.1-4), alkenyl (C.sub.2-5) or alkyl (C.sub.1-4)-sulfonyl, or R.sup.1 and R.sup.2 are combined together to form succinyl group, Ring A is phenyl, alkyl (C.sub.1-4)-phenyl or halogenophenyl, and n is an integer of 2 to 6, or a pharmaceutically acceptable acid addition salt thereof. The piperazine derivative (I) has an intracranial pressure-lowering activity. Said derivative also has a depressing effect on central nervous system.Type: GrantFiled: May 3, 1982Date of Patent: November 1, 1983Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Takeshi Kanno, Mitsunori Gaino, Michio Yamamura, Ryuichi Ishida, Keiichi Shintomi
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Patent number: 4411904Abstract: Compounds of the formula ##STR1## where X and Y are hydrogen, halogen, lower alkyl, nitro are useful as neuroleptics.Type: GrantFiled: June 14, 1982Date of Patent: October 25, 1983Assignee: Warner-Lambert CompanyInventor: Ian C. Pattison
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Patent number: 4397855Abstract: New 4-(substituted-.alpha., .alpha.-dimethyl-1-piperazine pentanoic acids and derivatives which are useful as anti-arteriosclerotic agents are disclosed. These compounds elevate the high density lipoprotein fraction of cholesterol, and also lower the low density lipoprotein fraction of cholesterol.Type: GrantFiled: June 26, 1981Date of Patent: August 9, 1983Assignee: Warner-Lambert CompanyInventor: Ila Sircar
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Patent number: 4395413Abstract: The invention relates to novel oxime ethers of the general formula /I/ and acid addition salts and quaternary ammonium derivatives thereof, ##STR1## wherein A represents a C.sub.2-6 straight or branched alkylene chain,R and R.sup.1 each represent a C.sub.1-6 alkyl group or they form together with the adjacent nitrogen atom a heterocyclic ring containing 4 to 7 carbon atoms and optionally a further hetero atom, i.e. an oxygen, sulfur or nitrogen atom, and said ring may be optionally substituted by a C.sub.1-3 alkyl, phenyl or benzyl group,R.sup.2 and R.sup.3 each denote a hydrogen atom or together form a valency bond,R.sup.4 denotes a C.sub.1-10 alkyl or C.sub.2-10 alkenyl group, andn denotes an integer from 3 to 7.The compounds of the general formula /I/ are prepared according to the invention by reacting a cycloalkane derivative of the general formula /II/ ##STR2## wherein R.sup.2, R.sup.3, R.sup.4 and n have the same meaning as above, whereasY denotes an oxygen or sulphur atom or a .dbd.Type: GrantFiled: June 24, 1980Date of Patent: July 26, 1983Assignee: Egyt Gyogyszervegyeszeti GyarInventors: Zoltan Budai, Aranka Lay nee Konya, Tibor Mezei, Lujza Petocz, Katalin Grasser, Ibolya Kosoczky, Eniko Szirt nee Kiszelly, Peter Gorog
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Patent number: 4367339Abstract: There are provided di- tri- and tetrasubstituted N-nitroaniline compounds and inorganic and organic salts thereof which are effective for increasing axillary branching, improving canopy and enhancing flowering of herbaceous ornamental plants and graminaceous crops, leguminous crops, cotton and sunflowers. The salts are also effective as yield enhancing agents and lodging inhibitors for the crops.Type: GrantFiled: August 18, 1980Date of Patent: January 4, 1983Assignee: American Cyanamid CompanyInventors: Thomas D. O'Neal, Prithvi R. Bhalla, Barrington Cross
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Patent number: 4364954Abstract: Compounds of the formula ##STR1## where X and Y are hydrogen, halogen, lower alkyl, nitro are useful as neuroleptics.Type: GrantFiled: May 29, 1981Date of Patent: December 21, 1982Assignee: Warner-Lambert CompanyInventor: Ian C. Pattison
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Patent number: 4342762Abstract: The invention relates to novel basic ethers of the general formula /I/ and pharmaceutically acceptable acid addition salts and quaternary salts thereof, ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and represent a C.sub.1-5 alkyl group or a C.sub.3-6 cycloalkyl group or they form, together with the adjacent nitrogen atom, a heterocyclic ring containing 4-7 carbon atoms and optionally a further hetero atom, e.g. an oxygen, sulfur or nitrogen atom, and this latter may be optionally substituted by a C.sub.1-3 alkyl, benzyl or phenyl group,R represents a phenyl, phenyl-/C.sub.1-3 alkyl/ or thienyl group optionally substituted by one or more halogen or C.sub.1-3 alkoxy substituent/s/,A represents a C.sub.2-5 straight or branched alkylene chain, and represents a valence bond of .alpha. or .beta. configuration.Type: GrantFiled: December 11, 1980Date of Patent: August 3, 1982Assignee: Egyt Gyogyszervegyeszeti GyarInventors: Zoltan Budai, Laszlo Magdanyi, Aranka Lay nee Konya, Tibor Mezei, Katalin Grasser, Lujza Petocz, Ibolya Kosoczky
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Patent number: 4335124Abstract: The compounds are 4-phenyl-4-lower alkyl-substituted-3-buten-2-ones, and -2-halo-1,3-butadienes, e.g., 2-(p-biphenylyl)-2-penten-4-one, and are useful as pharmaceuticals.Type: GrantFiled: October 14, 1980Date of Patent: June 15, 1982Assignee: Sandoz, Inc.Inventor: Eugene E. Galantay
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Patent number: 4330476Abstract: To synthesize triarylmethane dyestuffs of the general formula ##STR1## in which R.sup.1 and R.sup.2 represent optionally substituted alkyl, aryl or aralkyl orR.sup.1 and R.sup.2, together or with the ortho-position of the phenyl ring, form a heterocyclic ring and R.sup.1 can additionally represent hydrogen,R.sup.3 and R.sup.4 denote hydrogen or non-ionic substituents,n represents an integer from 1 to 4 andX.sup.- denotes an anion,by a one-pot process, an aldehyde of the general formula ##STR2## in which R.sup.4 and n have the abovementioned meaning,is subjected to a condensation reaction with an aromatic amine of the general formula ##STR3## in which R.sup.1, R.sup.2, R.sup.Type: GrantFiled: June 26, 1980Date of Patent: May 18, 1982Assignee: Bayer AktiengesellschaftInventor: Karl H. Hermann
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Patent number: 4322437Abstract: The present invention relates to a compound of formula I, ##STR1## wherein A is straight chain alkylene of 2 to 4 carbon atoms, or straight chain alkenylene of 2 to 4 carbon atoms,n is 1, 2 or 3,R is hydrogen or halogen of atomic number from 9 to 35, andeither (i) R.sub.1 is a group of formula II, ##STR2## wherein R.sub.2 and R.sub.3, independently, are hydrogen or alkyl of 1 to 4 carbon atoms, andR.sub.4 is alkyl of 1 to 4 carbon atoms, alkoxyalkyl of 2 to 5 carbon atoms, alkylthioalkyl of 2 to 5 carbon atoms, phenylalkyl or phenoxyalkyl or phenylthioalkyl, wherein the alkyl moiety has from 1 to 3 carbon atoms, or phenyl, the phenyl ring of each of the last four radicals being unsubstituted or mono-substituted by, or disubstituted independently by, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, hydroxy or halogen of atomic number from 9 to 35, andR.sub.5 is hydrogen,or (ii) R.sub.1 and R.sub.Type: GrantFiled: May 10, 1977Date of Patent: March 30, 1982Assignee: Sandoz Ltd.Inventors: Richard Berthold, Trevor G. Payne
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Patent number: 4308266Abstract: The present invention provides tetraline derivatives, useful for the treatment of hypertension, a process for their preparation and compositions containing these compounds.Type: GrantFiled: September 7, 1979Date of Patent: December 29, 1981Assignee: Sandoz Ltd.Inventor: Max-Peter Seiler
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Patent number: 4292321Abstract: Compounds of the formula ##STR1## where Q is defined hereinafter and X and Y are hydrogen, halogen, lower alkyl, nitro are useful as neuroleptics.Type: GrantFiled: January 10, 1980Date of Patent: September 29, 1981Assignee: Warner-Lambert CompanyInventor: Ian C. Pattison
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Patent number: 4273787Abstract: The compounds are 4-phenyl-4-lower alkyl-substituted-3-buten-2-ones, and -2-halo-1,3-butadienes, e.g., 2-(p-biphenylyl)-2-penten-4-one, and are useful as pharmaceuticals.Type: GrantFiled: August 9, 1979Date of Patent: June 16, 1981Assignee: Sandoz, Inc.Inventor: Eugene E. Galantay
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Patent number: 4267328Abstract: Phenylpiperazine derivatives having the general formula (I) ##STR1## in which R.sub.1 represents a radical S(O).sub.m R.sub.3, S(O).sub.n CF.sub.3 or ##STR2## in which radicals m is 0, 1 or 2, n is 1 or 2, R.sub.3 is an alkyl radical having 1 to 10 carbon atoms and R.sub.4 and R.sub.5 independently represent a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms, or the N atom, R.sub.4 and R.sub.5 together form a heterocyclic ring, which can contain another hetero-atom, and R.sub.2 represents a hydrogen atom, the radical CH.sub.2 --CH.sub.2 --OH or a radical of formula CH.sub.2 --CH.sub.2 --O--COR.sub.6, CH.sub.2 --CH.sub.2 --O--CONHR.sub.6 or CH.sub.2 --CH.sub.2 --O--R.sub.6 in which radicals R.sub.6 being an alkyl radical having 1 to 6 carbon atoms and their pharmaceutically acceptable acid addition salts are useful psychotropic agents and analgesics. Compounds in which R.sub.1 is --SCH.sub.3 and simultaneously R.sub.2 is H are not part of the invention.Type: GrantFiled: July 27, 1979Date of Patent: May 12, 1981Assignee: SynthelaboInventors: Henry Najer, Philippe Manoury
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Patent number: 4242343Abstract: Phenylpiperazine derivatives corresponding to the formula (I) ##STR1## in which n is 1, 2 or 3 and R represents the tetrahydrofuryl-2 radical, or the radical CH.sub.2 -SH, or a radical CH.sub.2 -S-alkyl, or a radical CH.sub.2 -O-alkyl or a radical CH.sub.2 -S-CO-alkyl, the alkyls having from 1 to 8 carbon atoms,and also their addition salts with pharmaceutically acceptable acids.These compounds are tranquilizers with psychotropic properties which permit their use in anxiety and depression.Type: GrantFiled: June 15, 1979Date of Patent: December 30, 1980Assignee: SynthelaboInventors: Henry Najer, Philippe Manoury
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Patent number: 4235914Abstract: Butyrophenone compounds having excellent psychotropic activity and represented by the formula: ##STR1## wherein Z is defined hereinbelow.Type: GrantFiled: October 17, 1978Date of Patent: November 25, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Kikuo Sasajima, Keiichi Ono, Hisao Yamamoto
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Patent number: 4223144Abstract: Compounds of the general formula I ##STR1## where B is a bridge member,the radicals R independently of one another are hydrogen or substituted or unsubstituted alkyl, or two radicals R together with the nitrogen are a heterocyclic saturated 5-membered or 6-membered ring,the radicals R.sup.1 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl,the radicals R.sup.2 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl or halogen,the radicals R.sup.3 independently of one another are hydrogen or substituted or unsubstituted alkyl or together are an alkylene group, and X.crclbar. is an anion. The compounds of the formula I are particularly suitable for dyeing paper.Type: GrantFiled: September 5, 1978Date of Patent: September 16, 1980Assignee: BASF AktiengesellschaftInventors: Hellmut Kast, Klaus Grychtol, Franz Feichtmayr
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Patent number: 4216326Abstract: N-{3- and 4-[R.sub.1 -(phenyl)-C(.dbd.X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 3- or 4-[R.sub.1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3- or 4-lithiophenyl-lower-alkylamine with a R.sub.1 -(phenyl)-carboxaldehyde, a R.sub.1 -(phenyl)-lower-alkyl ketone or a R.sub.1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.Type: GrantFiled: May 3, 1978Date of Patent: August 5, 1980Assignee: Sterling Drug Inc.Inventor: Bernard L. Zenitz
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Patent number: 4210646Abstract: Novel antimicrobial compositions comprising a 1-(aryloxyphenyl)piperazine as an active ingredient and a method of combatting the growth of microorganisms by the use of such 1-(aryloxyphenyl)piperazines.Type: GrantFiled: April 11, 1978Date of Patent: July 1, 1980Assignee: Janssen Pharmaceutica N.V.Inventor: Marcel A. C. Janssen
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Patent number: 4162316Abstract: 1-Substituted-4-(1,2-diphenylethyl)piperazine derivatives of the formula: ##STR1## wherein X is 2- or 3-hydroxy, 2-methoxy, 3-methyl, 3-alkoxy having 1 to 4 carbon atoms, or 2- or 3-alkanoyloxy having 2 to 5 carbon atoms; R is allyl, 3-hydroxyisoamyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, propyl, an unsubstituted monocycloalkyl having 5 to 8 carbon atoms, 2-chlorophenyl, or a phenyl substituted by hydroxy or methoxy; with proviso that when X is a substituent at position 2, R is cyclohexyl and when X is 3-methyl, R is 2-methoxyphenyl or an unsubstituted monocycloalkyl having 6 to 8 carbon atoms, and their pharmaceutically acceptable salts, and the preparation thereof, and analgesic or antitussive compositions containing the same as the essentially active ingredient.Type: GrantFiled: August 4, 1977Date of Patent: July 24, 1979Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Haruki Nishimura, Hitoshi Uno, Kagayaki Natsuka, Noriaki Shimokawa, Masanao Shimizu, Hideo Nakamura
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Patent number: 4130646Abstract: Compounds having the structure ##STR1## and pharmaceutically acceptible salts thereof, wherein R.sub.1 is hydrogen, halogen, hydroxy, alkanoyloxy, alkoxy, alkylthio, alkyl, trifluoromethyl or methylenedioxy; R.sub.2 is hydrogen, halogen, alkyl, alkoxy, alkylthio, or trifluoromethyl; R.sub.3 is formyl or alkanoyl; m is 1 or 2; and n is 0, 1 or 2, have useful sedative and muscle relaxant activity, and can be used as tranquilizers.Type: GrantFiled: April 22, 1976Date of Patent: December 19, 1978Assignee: E. R. Squibb & Sons, Inc.Inventors: B. Richard Vogt, David A. Cullison
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Patent number: 4128643Abstract: (2-Amino-4-quinazolinyl)-quanidines of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n have the defined meanings, and their physiologically tolerable acid addition salts, process for preparing these compounds, pharmaceutical preparations containing them and their use as medicines.Type: GrantFiled: May 26, 1977Date of Patent: December 5, 1978Assignee: Hoechst AktiengesellschaftInventors: Wulf Merkel, Hans G. Alpermann, Karl Geisen, Norbert Kothe, Walter Ried
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Patent number: 4122178Abstract: Piperazine compounds useful as analgesics, and having the formula: ##STR1## wherein each of R.sup.1 and R.sup.2 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or CF.sub.3 ; R.sup.3 is hydrogen, hydroxyl, an optionally substituted phenyl (e.g. phenyl, halo-phenyl, C.sub.1-4 alkyl-phenyl, C.sub.1-4 alkoxy-phenyl or CF.sub.3 -phenyl), pyridyl, 2-thienyl or 2-pyrimidinyl; m is 2 or 3; and n is 0, 1 or 2, and pharmaceutically acceptable acid addition salts thereof are disclosed.Type: GrantFiled: June 3, 1976Date of Patent: October 24, 1978Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Gen Hasegawa, Takanori Oe, Chiaki Kitami
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Patent number: 4101659Abstract: Benzhydryl derivatives of guanidine (Formula I) having blood sugar lowering activity; pharmaceutical hypoglycemic compositions thereof and methods of administering same to hyperglycemic individuals.Type: GrantFiled: August 29, 1977Date of Patent: July 18, 1978Assignee: McNeil Laboratories, IncorporatedInventor: Chris Royce Rasmussen
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Patent number: 4100282Abstract: Compounds of the formula ##STR1## wherein R is phenyl; phenyl having one or two substituents attached thereto, said substituents being selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, chlorine and trifluoromethyl; naphthyl; tetrahydronaphthyl; indanyl; pyridyl; isoquinolyl; or thiazolyl;R.sub.1 is ##STR2## where R.sub.3 is hydrogen, alkyl of 1 to 4 carbon atoms,R.sub.4 and R.sub.5 are each hydrogen or alkyl of 1 to 4 carbon atoms, andQ is oxygen or two hydrogens,R.sub.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen,A is a single carbon-to-carbon bond or --OCH.sub.2 --,R.sub.6 is hydrogen, hydroxyl, alkoxy of 1 to 4 carbon atoms or alkanoyloxy of 1 to 4 carbon atoms, andm is 0, 1, 2, 3, 4 or 5, but other than 0 when R.sub.Type: GrantFiled: May 4, 1977Date of Patent: July 11, 1978Assignee: Boehringer Ingelheim GmbHInventors: Ernst-Otto Renth, Anton Mentrup, Kurt Schromm, Peter Danneberg