Phenyl Or Naphthyl Bonded Directly To Ring Nitrogen Of The Piperazine Ring Patents (Class 544/392)
  • Patent number: 4686220
    Abstract: This disclosure describes certain substituted piperazine-1,4-naphthalenediones useful as anti-asthmatic agents.
    Type: Grant
    Filed: December 19, 1985
    Date of Patent: August 11, 1987
    Assignee: American Cyanamid Company
    Inventors: Jeffrey B. Medwid, Lawrence W. Torley, Andrew S. Tomcufcik
  • Patent number: 4666911
    Abstract: 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: Grant
    Filed: July 8, 1981
    Date of Patent: May 19, 1987
    Assignee: Taiho Pharmaceutical Company Limited
    Inventors: Hajime Fujimura, Yasuzo Hiramatu, Takahiro Yabuuchi, Masakatu Hisaki, Katsuo Takikawa, Takaji Honna, Hidekazu Miyake, Makoto Kajitani
  • Patent number: 4645862
    Abstract: 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: Grant
    Filed: April 15, 1985
    Date of Patent: February 24, 1987
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Yoshiyuki Tahara, Yasuhiro Komatsu, Hiroyasu Koyama, Reiko Kubota, Teruhito Yamaguchi, Toshihiro Takahashi
  • Patent number: 4613598
    Abstract: 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: Grant
    Filed: March 6, 1985
    Date of Patent: September 23, 1986
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Harukazu Fukami, Shinya Inoue, Issei Nitta, Kenichiro Nakao, Ryoji Kikumoto
  • Patent number: 4593027
    Abstract: 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: Grant
    Filed: October 11, 1983
    Date of Patent: June 3, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erhardt Winklemann, Walter Durckheimer, Wolfgang Raether
  • Patent number: 4590193
    Abstract: 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: Grant
    Filed: July 27, 1983
    Date of Patent: May 20, 1986
    Assignee: Societe Cortial, S.A.
    Inventors: Marie-Helene Creuzet, Claude Feniou, Francoise Guichard, Gisele Prat, Henri Pontagnier
  • Patent number: 4560686
    Abstract: 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: Grant
    Filed: September 14, 1983
    Date of Patent: December 24, 1985
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Hiroyuki Nagano, Mitiro Takagi, Noboru Kubodera, Isao Matsunaga, Hiroyuki Nabata, Yasuhiro Ohba, Kazushige Sakai, Shun-ichi Hata, Yasumi Uchida
  • Patent number: 4518712
    Abstract: 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: Grant
    Filed: June 22, 1981
    Date of Patent: May 21, 1985
    Assignee: Taiho Pharmaceutical Company Limited
    Inventors: Hajime Fujimura, Yasuzo Hiramatsu, Tomio Yamazaki, Shozo Yamada, Takaji Honna
  • Patent number: 4515793
    Abstract: 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: Grant
    Filed: July 27, 1983
    Date of Patent: May 7, 1985
    Assignee: Edna McConnell Clark Foundation
    Inventors: Leslie M. Werbel, Norman Colbry, William Turner, Donald F. Worth
  • Patent number: 4487721
    Abstract: 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: Grant
    Filed: June 7, 1983
    Date of Patent: December 11, 1984
    Assignee: Gruppo Lepetit S.p.A.
    Inventor: Romeo Ciabatti
  • Patent number: 4477664
    Abstract: 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: Grant
    Filed: February 22, 1982
    Date of Patent: October 16, 1984
    Assignee: 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
  • Patent number: 4474783
    Abstract: 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: Grant
    Filed: September 25, 1981
    Date of Patent: October 2, 1984
    Assignee: Innothera
    Inventors: Max F. Robba, Michel E. Aurousseau
  • Patent number: 4469694
    Abstract: 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: Grant
    Filed: February 25, 1980
    Date of Patent: September 4, 1984
    Assignee: Ayerst, McKenna & Harrison Inc.
    Inventors: Jehan F. Bagli, Tibor Bogri, Katherine Voith
  • Patent number: 4456756
    Abstract: 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: Grant
    Filed: August 3, 1981
    Date of Patent: June 26, 1984
    Assignee: Mead Johnson & Company
    Inventors: Davis L. Temple, Jr., Richard E. Yeager
  • Patent number: 4446133
    Abstract: 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: Grant
    Filed: February 13, 1981
    Date of Patent: May 1, 1984
    Assignee: Misuitoatsu Chemicals, Inc.
    Inventors: Yutaka Okazaki, Hiroshi Tokuda, Shiyoichiro Miyahara, Yoshitsugu Yamada
  • Patent number: 4438268
    Abstract: 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: Grant
    Filed: September 14, 1981
    Date of Patent: March 20, 1984
    Inventors: Horst Zaschke, Wolfgang Schafer, Hans-Joachim Deutscher, Dietrich Demus, Gerhard Pelzl
  • Patent number: 4421753
    Abstract: 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: Grant
    Filed: March 22, 1982
    Date of Patent: December 20, 1983
    Assignee: American Cyanamid Company
    Inventors: Andrew S. Tomcufcik, Walter E. Meyer, John P. Dusza
  • Patent number: 4413006
    Abstract: 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: Grant
    Filed: May 3, 1982
    Date of Patent: November 1, 1983
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Takeshi Kanno, Mitsunori Gaino, Michio Yamamura, Ryuichi Ishida, Keiichi Shintomi
  • Patent number: 4411904
    Abstract: Compounds of the formula ##STR1## where X and Y are hydrogen, halogen, lower alkyl, nitro are useful as neuroleptics.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: October 25, 1983
    Assignee: Warner-Lambert Company
    Inventor: Ian C. Pattison
  • Patent number: 4397855
    Abstract: 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: Grant
    Filed: June 26, 1981
    Date of Patent: August 9, 1983
    Assignee: Warner-Lambert Company
    Inventor: Ila Sircar
  • Patent number: 4395413
    Abstract: 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: Grant
    Filed: June 24, 1980
    Date of Patent: July 26, 1983
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Zoltan Budai, Aranka Lay nee Konya, Tibor Mezei, Lujza Petocz, Katalin Grasser, Ibolya Kosoczky, Eniko Szirt nee Kiszelly, Peter Gorog
  • Patent number: 4367339
    Abstract: 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: Grant
    Filed: August 18, 1980
    Date of Patent: January 4, 1983
    Assignee: American Cyanamid Company
    Inventors: Thomas D. O'Neal, Prithvi R. Bhalla, Barrington Cross
  • Patent number: 4364954
    Abstract: Compounds of the formula ##STR1## where X and Y are hydrogen, halogen, lower alkyl, nitro are useful as neuroleptics.
    Type: Grant
    Filed: May 29, 1981
    Date of Patent: December 21, 1982
    Assignee: Warner-Lambert Company
    Inventor: Ian C. Pattison
  • Patent number: 4342762
    Abstract: 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: Grant
    Filed: December 11, 1980
    Date of Patent: August 3, 1982
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Zoltan Budai, Laszlo Magdanyi, Aranka Lay nee Konya, Tibor Mezei, Katalin Grasser, Lujza Petocz, Ibolya Kosoczky
  • Patent number: 4335124
    Abstract: 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: Grant
    Filed: October 14, 1980
    Date of Patent: June 15, 1982
    Assignee: Sandoz, Inc.
    Inventor: Eugene E. Galantay
  • Patent number: 4330476
    Abstract: 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: Grant
    Filed: June 26, 1980
    Date of Patent: May 18, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventor: Karl H. Hermann
  • Patent number: 4322437
    Abstract: 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: Grant
    Filed: May 10, 1977
    Date of Patent: March 30, 1982
    Assignee: Sandoz Ltd.
    Inventors: Richard Berthold, Trevor G. Payne
  • Patent number: 4308266
    Abstract: The present invention provides tetraline derivatives, useful for the treatment of hypertension, a process for their preparation and compositions containing these compounds.
    Type: Grant
    Filed: September 7, 1979
    Date of Patent: December 29, 1981
    Assignee: Sandoz Ltd.
    Inventor: Max-Peter Seiler
  • Patent number: 4292321
    Abstract: 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: Grant
    Filed: January 10, 1980
    Date of Patent: September 29, 1981
    Assignee: Warner-Lambert Company
    Inventor: Ian C. Pattison
  • Patent number: 4273787
    Abstract: 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: Grant
    Filed: August 9, 1979
    Date of Patent: June 16, 1981
    Assignee: Sandoz, Inc.
    Inventor: Eugene E. Galantay
  • Patent number: 4267328
    Abstract: 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: Grant
    Filed: July 27, 1979
    Date of Patent: May 12, 1981
    Assignee: Synthelabo
    Inventors: Henry Najer, Philippe Manoury
  • Patent number: 4242343
    Abstract: 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: Grant
    Filed: June 15, 1979
    Date of Patent: December 30, 1980
    Assignee: Synthelabo
    Inventors: Henry Najer, Philippe Manoury
  • Patent number: 4235914
    Abstract: Butyrophenone compounds having excellent psychotropic activity and represented by the formula: ##STR1## wherein Z is defined hereinbelow.
    Type: Grant
    Filed: October 17, 1978
    Date of Patent: November 25, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kikuo Sasajima, Keiichi Ono, Hisao Yamamoto
  • Patent number: 4223144
    Abstract: 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: Grant
    Filed: September 5, 1978
    Date of Patent: September 16, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Hellmut Kast, Klaus Grychtol, Franz Feichtmayr
  • Patent number: 4216326
    Abstract: 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: Grant
    Filed: May 3, 1978
    Date of Patent: August 5, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4210646
    Abstract: 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: Grant
    Filed: April 11, 1978
    Date of Patent: July 1, 1980
    Assignee: Janssen Pharmaceutica N.V.
    Inventor: Marcel A. C. Janssen
  • Patent number: 4162316
    Abstract: 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: Grant
    Filed: August 4, 1977
    Date of Patent: July 24, 1979
    Assignee: Dainippon Pharmaceutical Co., Ltd.
    Inventors: Haruki Nishimura, Hitoshi Uno, Kagayaki Natsuka, Noriaki Shimokawa, Masanao Shimizu, Hideo Nakamura
  • Patent number: 4130646
    Abstract: 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: Grant
    Filed: April 22, 1976
    Date of Patent: December 19, 1978
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: B. Richard Vogt, David A. Cullison
  • Patent number: 4128643
    Abstract: (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: Grant
    Filed: May 26, 1977
    Date of Patent: December 5, 1978
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wulf Merkel, Hans G. Alpermann, Karl Geisen, Norbert Kothe, Walter Ried
  • Patent number: 4122178
    Abstract: 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: Grant
    Filed: June 3, 1976
    Date of Patent: October 24, 1978
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Gen Hasegawa, Takanori Oe, Chiaki Kitami
  • Patent number: 4101659
    Abstract: Benzhydryl derivatives of guanidine (Formula I) having blood sugar lowering activity; pharmaceutical hypoglycemic compositions thereof and methods of administering same to hyperglycemic individuals.
    Type: Grant
    Filed: August 29, 1977
    Date of Patent: July 18, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris Royce Rasmussen
  • Patent number: 4100282
    Abstract: 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: Grant
    Filed: May 4, 1977
    Date of Patent: July 11, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Ernst-Otto Renth, Anton Mentrup, Kurt Schromm, Peter Danneberg