Nitrogen Bonded Directly To The Bicyclo Ring System Patents (Class 549/404)
  • Patent number: 5637709
    Abstract: Polychromatic compounds of pyrans having a substituted adamantane or a polycyclic ring system, with the exception of adamantane, in the 2-position of the pyran ring, having the structure ##STR1## whereby the residues R.sub.1 -R.sub.4 are independently substituents selected from the series H, alkyl, substituted phenyl, phenyl, naphthyl, OH, alkoxy (C.sub.1 -C.sub.4), halogen, alkylamino, dialkylamino, cyan, trifluormethyl, or, R.sub.1 and R.sub.2 or R.sub.3 and R.sub.4 or R.sub.2 and R.sub.3 are constituents of at least one condensed aromatic, heteroaromatic or an alkane ring, wherein said heteroaromatic ring is selected from the group consisting of pyridine, pyrimidine, pyridazine, quinoline, isoquinoline, naphthyridine, quinazoline, quinoxaline, phthalazine, pteridine, phenazine, and benzoquinoline which are substituted by the same residues as R.sub.1 -R.sub.
    Type: Grant
    Filed: February 9, 1995
    Date of Patent: June 10, 1997
    Assignee: Optische Werke G. Rodenstock
    Inventor: Manfred Melzig
  • Patent number: 5629429
    Abstract: A method of preparing compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof which comprises converting a compound of the formula ##STR2## where the R.sup.2 substituent contains a hydrogen atom which is more acidic than the starred (*) hydrogen atom in formula II, to the corresponding dianion of formula ##STR3## where M is a counterion preferably lithium or magnesium, using two equivalents of a base in an inert solvent such as tetrahydrofuran; then reacting compounds of formula IIA with an epoxide of formula ##STR4## to produce the compounds of formula I.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: May 13, 1997
    Assignee: Bristol-Myers Squibb Company
    Inventors: David R. Kronenthal, Richard H. Mueller, Jollie D. Godfrey, Jr.
  • Patent number: 5616610
    Abstract: Compounds of the general formula ##STR1## wherein R.sub.1 is n-propyl or cyclobutyl;R.sub.2 is isopropyl, tertiary butyl, cyclobutyl, cyclopentyl or cyclohexyl;R.sub.3 is hydrogen;R.sub.4 is hydrogen or methyl;as (R)-enantiomer in the form of free base or pharmaceutically acceptable salts thereof, process for their preparation, pharmaceutical composition, use of and method of treatment of disorders in CNS.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: April 1, 1997
    Assignee: Astra Aktiebolag
    Inventors: John L. Evenden, Eva M. Hammarberg, Hans S. Hansson, Sven E. Hellberg, Lars G. Johansson, Johan R. M. Lundkvist, Svante B. Ross, Daniel D. Sohn, Seth O. Thorberg
  • Patent number: 5612370
    Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein a, b and d are all carbon atoms or one of a, b and d is a nitrogen atom or --N(O)-- and the others are carbon atoms; Y is a single bond, --CH.sub.2 --, --C(O)--, --O--, --S-- or --N(R.sup.8)--; and R.sup.1 to R.sup.7 are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 18, 1997
    Assignee: Bristol-Myers Squibb Company
    Inventor: Karnail S. Atwal
  • Patent number: 5574061
    Abstract: A benzopyran derivative represented by the formula (I) or its pharmaceutically acceptable salt: ##STR1## wherein either one of X and Y stands for the following formula ##STR2## and the other one of X and Y and R.sup.1 -R.sup.10 stand for various substituents,and ACAT inhibitor, anti-hyperlipidemia agent and anti-atherosclerosis agent compositions containing the same as an active ingredient.
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: November 12, 1996
    Assignee: Teijin Limited
    Inventors: Tatsuki Shiota, Takumi Takeyasu, Kenichiro Kataoka, Tsutomu Mochizuki, Hirofumi Tanabe, Mikio Ota, Hisao Yamaguchi
  • Patent number: 5556996
    Abstract: Compounds of the formula ##STR1## wherein all the symbols in the formula are as defined in the specification, have retinoid-like activity.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: September 17, 1996
    Assignee: Allergan
    Inventors: Richard L. Beard, Roshantha A. Chandraratna
  • Patent number: 5536833
    Abstract: A process for preparing compounds of the formula ##STR1## where a, b, c, R.sub.1, R.sub.2, and R.sub.3 are as defined herein including the step of alkylating a phenol of formula ##STR2## with an acetylene of formula ##STR3## where X is chlorine; bromine; --OC(O)--R.sub.5, where R.sub.5 is alkyl, aryl or substituted aryl; or --OCO.sub.2 R.sub.6, where R.sub.6 is alkyl or ##STR4## in the presence of a catalytic amount of a cuprous or cupric salt. The compounds of formula I are intermediates useful in the preparation of pyranyl cyanoguanidine derivatives.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 16, 1996
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jollie D. Godfrey, Jr., Richard H. Mueller, Thomas C. Sedergran, Nachimuthu Soundararajan
  • Patent number: 5534536
    Abstract: Fused phenol compounds of the formula (I): ##STR1## (wherein R.sup.1 and R.sup.2 each, independently, is H, halogen, trifluoromethyl, cyano, (substituted) alkyl, alkoxy, cycloalkyl, COOH, COOR.sup.6 (in which R.sup.6 is C1-6 alkyl), alkenyl or R.sup.1 and R.sup.2, taken together, is --CH.dbd.CH--CH.dbd.CH--, when R.sup.1 and R.sup.2 are ortho to each other; A is alkylene, alkenylene, oxyalkylene or ##STR2## (in which m is 1-6); B is a monocyclic hetero ring containing a nitrogen atom; G is --OR.sup.3A or --NR.sup.3B R.sup.3C (in which R.sup.3A, R.sup.3B and R.sup.3C each, independently, is H, alkyl, acyl, or alkoxyalkyl); R.sup.4 and R.sup.5 each, independently, is H, alkyl, or R.sup.4, R.sup.5 together with the carbon atom to which they are attached represent C4-7 cycloalkyl; and n is 1-3; non-toxic salts thereof, non-toxic acid addition salts thereof, and hydrates thereof.The compounds of the formula (I) have inhibitory activities on TXA.sub.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: July 9, 1996
    Assignee: Ono Pharmaceuticals Co. Ltd.
    Inventors: Shuichi Ohuchida, Fumio Nambu, Masaaki Toda
  • Patent number: 5510374
    Abstract: The invention relates to compounds of the formula (I): ##STR1## in which: Z represents oxygen,R.sub.1 represents alkyl,R.sub.2 represents hydrogen or alkyl,n represents 1 through 6,R.sub.3 represents unsubstituted or substituted phenylacylamino, and antidepressive and other medicinal products containing the same.
    Type: Grant
    Filed: July 18, 1994
    Date of Patent: April 23, 1996
    Assignee: Adir et Compagnie
    Inventors: Gerald Guillaumet, Beatrice Guardiola
  • Patent number: 5500425
    Abstract: Compounds of the formula I ##STR1## processes for their preparation, pharmaceutical preparations, use of and method of treatment of disorders in CNS by using compounds of formula I.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: March 19, 1996
    Assignee: Aktiebolaget Astra
    Inventors: Lars-Gunnar Larsson, Lucy A. Renyl, Svante B. Ross, Daniel D. Sohn, Seth-Olov Thorberg
  • Patent number: 5498634
    Abstract: The present invention provides a thioformamide derivative represented by the following general formula (I) or a pharmacologically acceptable salt thereof, which is highly safe, easy to use, and useful as an excellent hypotensive or heart disease remedy: ##STR1## wherein Y represents ##STR2## or the like [wherein R.sup.7 represents benzyloxy or the like; R.sup.11 and R.sup.12 each represent hydrogen, hydroxyl, benzoyloxy, benzyloxy, ##STR3## (wherein R.sup.14 and R.sup.15 each represent hydrogen, benzyl or the like) or the like];Z represents --CH.sub.2 -- or the like; A represents imidazolyl or imidazopyridyl which may have one or two substituents, or the like; R.sup.1 and R.sup.2 each represent hydrogen, lower alkyl or the like; and R.sup.3 and R.sup.4 each represent hydrogen, lower alkyl or the like.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: March 12, 1996
    Assignee: Eisai Co., Ltd.
    Inventors: Yasuhiro Kabasawa, Fumihiro Ozaki, Keiji Ishibashi, Takashi Hasegawa, Hitoshi Oinuma, Toshiaki Ogawa, Hideyuki Adachi, Hiroshi Katoh, Kohtarou Kodama, Hideto Ohara, Nobuyuki Mori, Norio Minami
  • Patent number: 5495026
    Abstract: A phenol, a formaldehyde and an unsaturated compound having carbon-carbon double bond are reacted in the presence of a secondary amine and an acid at a temperature of 100.degree. to 250.degree. C., to give a chroman.
    Type: Grant
    Filed: September 13, 1994
    Date of Patent: February 27, 1996
    Assignee: Kuraray Company Ltd.
    Inventors: Eriko Fukumoto, Masahiro Torihara, Yoshin Tamai
  • Patent number: 5482966
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: January 9, 1996
    Assignees: Zeneca Limited, Zeneca Pharma S.A.
    Inventors: Thomas G. C. Bird, Patrick Ple
  • Patent number: 5482942
    Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: January 9, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 5472979
    Abstract: R.sub.1 and R.sub.2 form, with the carbon atoms to which they are attached, cyclopentane or cyclohexane,R.sub.3 represents hydroxyl, linear or branched (C.sub.1 -C.sub.6) alkoxy or unsubstituted or substituted amino,R.sub.4 represents alkyl, unsubstituted or substituted phenyl, naphthyl, pyridyl or thienyl, X represents methylene or oxygen or sulfur,its enantiomers and its addition salts with a pharmaceutically acceptable base, and medicinal products containing the same are useful as anti-thrombotic.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: December 5, 1995
    Assignee: Adir et Compagnie
    Inventors: Gilbert Lavielle, Thierry Dubuffet, Olivier Muller, Michel Laubie, Tony Verbeuren, Serge Simonet, Jean-Jacques Descombes
  • Patent number: 5470977
    Abstract: The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes, including their corresponding sulfoxides and sulfones, which ring-substituted compounds exhibit agonist activity at the serotonin 1A receptor.
    Type: Grant
    Filed: March 14, 1995
    Date of Patent: November 28, 1995
    Assignee: Eli Lilly and Company
    Inventors: John M. Schaus, Craig S. Hoechstetter, Diane Huser, Charles J. Paget, Robert D. Titus
  • Patent number: 5470872
    Abstract: Novel CompoundsA compound of formula (I): ##STR1## where the substituents are defined later in the specification. The compounds are useful as muscle relaxants and as such have a number of pharmaceutical uses.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: November 28, 1995
    Assignee: Beecham Group plc
    Inventors: Derek R. Buckle, Ivan L. Pinto, David G. Smith
  • Patent number: 5468878
    Abstract: Cyclohexanedione derivatives of the general formula (I), ##STR1## wherein: R is a C.sub.1 -C.sub.4 alkyl group,each of R.sup.1 to R.sup.6 is independently hydrogen or a C.sub.1 -C.sub.4 alkyl group,X.sup.1 is a C.sub.1 -C.sub.4 alkyl group,X.sup.2 is hydrogen or a C.sub.1 -C.sub.4 alkyl group, andn is an integer of 0 to 2.or salta thereof exhibit high selectivity for corn, wheat and barley, can control gramineous weeds and broad-leaved weeds at a low dosage, and can be desirably used as an active ingredient of a herbicide.
    Type: Grant
    Filed: February 2, 1995
    Date of Patent: November 21, 1995
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Ichiro Nasuno, Mitsuru Shibata, Masashi Sakamoto, Kazuyoshi Koike
  • Patent number: 5468870
    Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 or CN;R.sup.4 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent substituted or unsubstituted amino, or R.sup.5 and R.sup.
    Type: Grant
    Filed: October 20, 1994
    Date of Patent: November 21, 1995
    Assignee: AGFA-GAVAERT, N.V.
    Inventor: Luc J. Vanmaele
  • Patent number: 5466709
    Abstract: The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes, including their corresponding sulfoxides and sulfones, which ring-substituted compounds exhibit agonist activity at the serotonin 1A receptor.
    Type: Grant
    Filed: March 14, 1995
    Date of Patent: November 14, 1995
    Assignee: Eli Lilly and Company
    Inventors: John M. Schaus, Craig S. Hoechstetter, Diane Huser, Charles J. Paget, Robert D. Titus
  • Patent number: 5453421
    Abstract: Novel compounds useful, for example, for the treatment of ischemic conditions and arrhythmia are disclosed. The compounds have the formula ##STR1## wherein X is oxygen or sulfur and the R groups are as defined herein.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: September 26, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Karnail S. Atwal, Syed Z. Ahmed, Dinos P. Santafianos
  • Patent number: 5430060
    Abstract: The invention concerns novel N-phenylacetyl and related acyl derivatives of (4-amino-2,6-dimethylphenylsulphonyl)nitromethane and pharmaceutically acceptable salts thereof which are inhibitors of the enzyme aldose reductase and are of value, for example, in the treatment of certain peripheral effects of diabetes and galactosemia. Also disclosed are pharmaceutical compositions containing one of the derivatives and processes for the manufacture and use of the derivatives.
    Type: Grant
    Filed: September 15, 1993
    Date of Patent: July 4, 1995
    Assignee: Zeneca Limited
    Inventors: David R. Brittain, Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey J. Morris, John Preston, Linda Slater
  • Patent number: 5428027
    Abstract: Certain substituted semicarbazones, including all geometric and stereoisomers thereof, agricultural compositions containing them and their use as arthropodicides.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: June 27, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John P. Daub, George P. Lahm, Bradford S. Marlin
  • Patent number: 5426229
    Abstract: The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes, including their corresponding sulfoxides and sulfones, which ring-substituted compounds exhibit agonist activity at the serotonin 1A receptor.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: June 20, 1995
    Assignee: Eli Lilly and Company
    Inventors: John M. Schaus, Craig S. Hoechstetter, Diane Huser, Charles J. Paget, Robert D. Titus
  • Patent number: 5420151
    Abstract: 3-amino-5-carbamoylchromans and 8-fluoro-3-amino-5-carbamoylchromans, as well as enantiomers and salts thereof, are disclosed. Pharmaceutical compositions containing the compounds as active ingredients are also disclosed. The compounds are useful in the treatment of 5-hydroxytryptamine-mediated disorders of the central nervous system.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: May 30, 1995
    Assignee: Aktiebolaget Astra
    Inventors: Eva M. Hammarberg, Lars G. Johansson, Svante B. Ross, Seth-Olov Thorberg
  • Patent number: 5416118
    Abstract: Novel bicyclic amides of the formula ##STR1## wherein Ar.sup.1 and Ar.sup.2 are phenyl, R.sup.2 -substituted phenyl, heteroaryl or R.sup.2 -substituted heteroaryl, wherein R.sup.2 is 1 to 3 substituents independently selected from the group consisting of halogeno, hydroxy, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino and lower dialkylamino;X, Y and Z are --CH.sub.2 --, --CH(alkyl)--, --C(alkyl).sub.2 --, --NH--, --N(alkyl)--, --O-- or --SO.sub.r, wherein r is 0, 1 or 2, and m, n and p are 0 or 1;R.sup.1 is an alkyl chain of 1 to 25 carbon atoms; an alkyl chain substituted by one or more optionally substituted phenyl or heteroaryl groups; an alkyl chain --O--, --SO.sub.r, phenylene, R.sup.2 -substituted phenylene, heteroarylene or R.sup.
    Type: Grant
    Filed: September 28, 1993
    Date of Patent: May 16, 1995
    Assignee: Schering Corporation
    Inventors: John W. Clader, Thomas Fevig, Wayne Vaccaro, Joel G. Berger
  • Patent number: 5412117
    Abstract: Benzopyran derivatives represented by formula (I): ##STR1## wherein X represents =O, =S, =N-Z (Z represents a lower alkyl group, etc.), or =CHNO.sub.2 ; Y represents a substituted amino group, an alkoxy group, an alkylthio group, etc., and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 each represent a hydrogen atom, a lower alkyl group, etc., are disclosed. The benzopyran derivatives exhibit K.sup.+ channel activating activities and are widely applicable as antiasthmatics, antiepileptics, and the like.
    Type: Grant
    Filed: January 26, 1993
    Date of Patent: May 2, 1995
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Hiroshi Koga, Hiroyuki Nabata
  • Patent number: 5412104
    Abstract: Compounds useful as antihypertensive agents and useful as antiviral agents against DNA-containing viruses, such as herpes group viruses, are disclosed. The compounds are represented by Formula 1.0: ##STR1## and their pharmaceutically acceptable salts and solvates. Pharmaceutical compositions containing compounds represented by Formula 1.0 are disclosed. Methods of treating a viral infection using compounds represented by Formula 1.0 are disclosed.Also disclosed are methods of treating hypertension using compounds of Formula 1.0 wherein R is selected from the group consisting of H, halogen and --C(O)OR.sup.6 ; and R.sup.1 is selected from the group consisting of --OR.sup.14, --O(CH.sub.2).sub.a C(H).sub.3-i Z.sub.i and --O(CH.sub.2).sub.h N(R.sup.15).sub.2.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: May 2, 1995
    Assignee: Schering Corporation
    Inventors: Adriano Afonso, Jay Weinstein, Margaret J. Gentles
  • Patent number: 5405976
    Abstract: Dyes comprising an inner salt of a compound of the formula:Q.sup.1 =Z-Q.sup.2wherein:Q.sup.1 is a 4-(benz[b]-4H-pyrylium)methylidene, 4-(benz[b]-4H-thiopyrylium)methylidene or 4-(benz[b]-4H-selenopyrylium)methylidene grouping;Z is a 1,3-(2-hydroxy-4-oxo-2-cyclobutylidene) hydroxide or 1,3-(2-hydroxy-4,5-dioxo-2-cyclopentylidene) hydroxide ring; andQ.sup.2 is a 4-(benz[b]-4H-pyran-4-ylidene)methyl, 4-(benz[b]-4H-thiopyran-4-ylidene)methyl or 4-(benz[b]-4H-selenopyran-4-ylidene)methyl grouping;wherein at least one of the groupings Q.sup.1 and Q.sup.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: April 11, 1995
    Assignee: Polaroid Corporation
    Inventors: Stephen J. Telfer, Robert P. Short, Stephen G. Stroud, Anthony J. Puttick, Socorro Ramos, Michael J. Zuraw
  • Patent number: 5393771
    Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.
    Type: Grant
    Filed: May 12, 1993
    Date of Patent: February 28, 1995
    Assignee: Brisol-Myers Squibb Company
    Inventor: Karnail S. Atwal
  • Patent number: 5380748
    Abstract: A trialkylamine derivative represented by the formula (1) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different from each other and each represents lower alkyl;R.sup.3, R.sup.4 and R.sup.5 may be the same or different from one another and each represents hydrogen, lower alkyl, lower alkoxy, lower alkoxycarbonyl or halogen;R.sup.6 and R.sup.7 may be the same or different from each other and each represents hydrogen or lower alkyl;R.sup.8 represents hydrogen, lower alkyl, lower alkoxy or halogen;X represents oxygen, sulfur, --CH.dbd.N-- or --CH.dbd.CH--;Y represents oxygen, sulfur, methylene, N--R.sup.11 (wherein R.sup.11 represents lower alkyl), SO or SO.sub.2 ;Z represents --OCO(CH.sub.2).sub.p .about. or --OCH.sub.2 (CH.sub.2).sub.p .about. (wherein p represents a number of 0 to 4 and symbol .about.
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Zeria Pharmaceutical Co., Ltd.
    Inventors: Yoshiaki Muto, Hiromi Ichikawa, Kuniyoshi Ogura, Kyoji Chaki, Masao Seiki, Toshihiko Takemasa
  • Patent number: 5371228
    Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, alkyl, cycloalkyl, aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 ;R.sup.4 represents hydrogen, alkyl, cycloalkyl, aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent amino, or R.sup.5 and R.sup.6 together represent the necessary atoms to close a heterocyclic nucleus, including a heterocyclic nucleus with an aliphatic or aromatic ring fused-on;R.sup.7 and R.sup.
    Type: Grant
    Filed: August 24, 1992
    Date of Patent: December 6, 1994
    Assignee: Agfa-Gevaert, N.V.
    Inventor: Luc J. Vanmaele
  • Patent number: 5371084
    Abstract: Compounds having the formula (I): ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryloxy, optionally substituted heteroaryloxy, nitro, halo, cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein n is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: December 6, 1994
    Assignee: Zeneca Limited
    Inventors: Paul J. de Fraine, Anne Martin
  • Patent number: 5354873
    Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an aromatic unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an acyl, aliphatic, cycloaliphatic, aromatic or heterocyclic group, subject to the proviso that one of R.sup.3 and R.sup.4 may be an amino or substituted amino group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a nitrogenous heterocyclic ring) are useful as near infra-red absorbers.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: October 11, 1994
    Assignee: Polaroid Corporation
    Inventors: Richard M. Allen, Peter K. Chu, John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
  • Patent number: 5348976
    Abstract: The present invention provides a condensed heterocyclic derivative represented by a formula: ##STR1## wherein R.sup.1 represents a lower alkyl group, an alkenyl group, or the like, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 independently represent a hydrogen atom, a lower alkyl, or the like, W is represented by --OC(O)--, --SC(O)--, or the like, and Z represents a 2-indolyl group or the like. The present invention also provides an agricultural or horticultural fungicide which comprises an amount of the condensed derivative known to be effective as a fungicide. The agricultural or horticultural fungicide according to the present invention exhibits a superior control effect for downy mildew and late blight, without harm to nonfungal, photosynthesizing plants.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: September 20, 1994
    Assignees: Kumai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masaru Shibata, Shigekazu Ito, Jun-etsu Sakai, Shigeru Hayashi
  • Patent number: 5346916
    Abstract: The invention relates to compounds of the formula (I): ##STR1## in which: Z represents an oxygen atom or a sulfur atom,R.sub.1 represents a hydrogen atom or an alkyl group,R.sub.2 represents a hydrogen atom or an alkyl group,n is one to six, inclusive,R.sub.3 represents an amino group, substituted with phenylsulfonyl, andmedicinal products containing the same.
    Type: Grant
    Filed: March 16, 1993
    Date of Patent: September 13, 1994
    Assignee: Adir Et Compagnie
    Inventors: Gerald Guillaumet, Beatrice Guardiola
  • Patent number: 5326784
    Abstract: New cycloalkylalkylamines which are sigma-receptor ligands of formule (I) ##STR1## in which: R.sub.1 is H or lower alkyl; X and Y are H, OH, lower alkyl, lower alkoxy, halogen or nitrile; V.sub.1 and V.sub.2 together form a double bond attached to an oxygen atom or to a hydroxyimino radical, or are linked as an ethylenedioxy chain; A represents a valency bond, an oxygen atom, a methylene or an ethylene group; m is equal to 0, 1 or 2; n has the value of an integer from 1 to 5. Psychotropic drug which is also useful in gastroenterology.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: July 5, 1994
    Assignee: Institut de Recherche Jouveinal
    Inventors: Jean-Louis Junien, Alain Calvet, Henri Jacobelli, Francois Roman
  • Patent number: 5318969
    Abstract: A benzopyran compound of the general formula (I) ##STR1## wherein A represents --OR.sup.1 or --NH--COR.sup.2 ; R.sup.3 represents hydrogen, a lower alkyl, a lower alkoxy, amino, a mono- or di-lower alkylamino, an amino-lower alkyl, a hydroxy-lower alkyl, a halo-lower alkyl, a lower alkoxy-lower alkyl, an acyloxy-lower alkyl, a lower alkoxycarbonyl-lower alkyl, an aryl or a heteroaryl, or R.sup.2 and R.sup.3 combinedly together form an alkylene having 1 to 2 carbon atoms; R.sup.4 and R.sup.5 are the same or different, and respectively represent hydrogen or a lower alkyl, or combinedly together form an alkylene having 2 to 5 carbon atoms; R.sup.6 represents hydroxyl group, formyloxy, an alkanoyloxy, a haloalkanoyloxy, a lower alkoxycarbonyloxy, an aroyloxy, a heteroaroyloxy, carbamoyloxy, a mono- or di-lower alkylcarbamoyloxy and R.sup.7 represents hydrogen, or R.sup.6 and R.sup.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: June 7, 1994
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tsutomu Yamanaka, Toshio Seki, Tohru Nakajima, Osamu Yaoka
  • Patent number: 5306830
    Abstract: The present invention is directed to novel chromane derivatives substituted in the 3-position by a substituted amino moiety and substituted on the aromatic ring with one or two substituents. The novel chromane derivatives have useful CNS properties.
    Type: Grant
    Filed: December 21, 1992
    Date of Patent: April 26, 1994
    Assignee: The Upjohn Company
    Inventors: Bengt R. Andersson, Per A. E. Carlsson, Kjell A. I. Svensson, Hakan V. Wikstrom, Anders R. Hallberg
  • Patent number: 5300646
    Abstract: A novel heterocyclic amine derivative of the general formula: ##STR1## wherein a ring A and a ring B stand independently for an optionally substituted benzene ring, Z.sup.o stands for O or S or ##STR2## stands for --CH.sub.2 --, X stands for O, S or NR.sup.1 wherein R.sup.1 stands for hydrogen atom or an alkyl group, Y stands for NH, O or (CH.sub.2).sub.n wherein n denotes 0 to 2, and R.sup.2 stands for an optionally substituted hydrocarbon group, or their salts.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: April 5, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideaki Natsugari, Hiroyuki Tawada, Hitoshi Ikeda
  • Patent number: 5300522
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen. acyl, lower-alkyl or --CHO, --CH.sub.2 OR.sup.10, --COR.sup.7 or OR.sup.13 ; R.sup.2, R.sup.3 and R.sup.4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.5 and R.sup.5 are, independently, hydrogen or lower-alkyl; R.sup.7 is hydroxy, lower-alkoxy or NR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR.sup.14 R.sup.15, --O--, --S--, >SO, >SO.sub.2 or >NR.sup.18 ; R.sup.10 and R.sup.18 are, independently, hydrogen, lower-alkyl or acyl; M is --C(R.sup.11).dbd.C(R.sup.12)--, --CONH-- or --NH--CO--; R.sup.11, R.sup.12, R.sup.14 and R.sup.15 are, independently, hydrogen or lower-alkyl, R.sup.
    Type: Grant
    Filed: August 18, 1992
    Date of Patent: April 5, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 5294635
    Abstract: Certain spirocyclic heterocyclic compounds, and their pharmaceutically-acceptable salts, are inhibitors of the aldose reductase enzyme, and so are useful for the control of diabetic complications.
    Type: Grant
    Filed: September 17, 1992
    Date of Patent: March 15, 1994
    Assignee: Pfizer, Inc.
    Inventors: James F. Eggler, Eric R. Larson
  • Patent number: 5286753
    Abstract: The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes, including their corresponding sulfoxides and sulfones, which ring-substituted compounds exhibit agonist activity at the serotonin 1A receptor.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: February 15, 1994
    Assignee: Eli Lilly and Company
    Inventors: John M. Schaus, Craig S. Hoechstetter, Diane Huser, Charles J. Paget, Robert D. Titus
  • Patent number: 5276168
    Abstract: A new method for the treatment of ischemic conditions and arrhythmia is disclosed. The method uses compounds of the formula ##STR1## wherein A can be --CH.sub.2 --, --O--, --NR.sub.9 --, --S--, --SO--, --SO.sub.2 --; X can be oxygen or sulfur; Y can be --NR.sub.8, --O--, --S--, --CH.sub.2 -- and the R groups are as defined herein. Novel compounds within the definition of formula I are also disclosed.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: January 4, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 5270342
    Abstract: The invention concerns novel N-phenylacetyl and related acyl derivatives of (4-amino-2,6-dimethylphenylsulphonyl)nitromethane and pharmaceutically acceptable salts thereof which are inhibitors of the enzyme aldose reductase and are of value, for example, in the treatment of certain peripheral effects of diabetes and galactosemia. Also disclosed are pharmaceutical compositions containing one of the derivatives and processes for the manufacture and use of the derivatives.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: December 14, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David R. Brittain, Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey J. Morris, John Preston, Linda Salter
  • Patent number: 5268386
    Abstract: A novel heterocyclic compound capable of lowering the uric acid levels in plasma and urine having the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, lower alkyl, phenyl or substituted phenyl, or R.sup.1 and R.sup.2 may form a four- to eight-membered carbon ring together with the carbon atom to which they are attached; R.sup.3 is hydrogen or lower alkyl; R.sup.4 is one or two radicals selected from a group consisting of hydrogen, halogen, nitro, lower alkyl, phenyl, substituted phenyl, --OR.sup.5 and --SO.sub.2 NR.sup.6 R.sup.6' ; R.sup.5 is hydrogen, lower alkyl, phenyl-substituted lower alkyl, carboxymethyl or ester thereof, hydroxyethyl or ether thereof, or allyl; R.sup.6 and R.sup.6' are independently hydrogen or lower alkyl; R.sup.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: December 7, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Hiroshi Harada, Eiichi Ohsugi, Yukio Yonetani, Toshihiro Shinosaki
  • Patent number: 5262549
    Abstract: 4-[3-(benz[b]pyran-4-ylidene)prop-1-enyl]benz[b]pyrylium, 4-[5-(4H-benz[b]pyran-4-ylidene)penta-1,3-dienyl]benz[b]pyrylium and 4-[7-(4H-benz[b]pyran-4-ylidene)hepta-1,3,5-trienyl]benz[b]pyrylium dyes, wherein at least one of the benzpyrylium nuclei carries at its 2-position a substituent in which a non-aromatic carbon atom is bonded directly to the benzpyrylium nucleus, subject to the proviso that if the or each 2-substituent contains an aromatic nucleus, this aromatic nucleus is not conjugated with the benzpyrylium nucleus, are useful as visible and near infra-red absorbers, having high extinction coefficients and a reduced tendency to develop absorptions at shorter wavelengths when dispersed in polymeric media.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: November 16, 1993
    Assignee: Polaroid Corporation
    Inventors: Stephen J. Telfer, Socorro M. Ramos, Michael J. Zuraw
  • Patent number: 5232944
    Abstract: Novel chroman derivatives of the formula I ##STR1## in which X is O or NR.sup.11,Z is CH.sub.2, O, S or CHHal,R.sup.1 and R.sup.5 are each A,R.sup.2 is H or A,R.sup.1 and R.sup.2 together are also alkylene having 3-6 C atoms,R.sup.3 is OH or OAc,R.sup.4 is H,R.sup.3 and R.sup.4 together are also a bond,R.sup.6 and R.sup.7 are each H, A, HO, AO, CHO, ACO, ACS, HOOC, AOOC, AO--CS, ACOO, A--CS--O, hydroxyalkyl, NO.sub.2, NH.sub.2, NHA, NA.sub.2, CN, F, Cl, Br, I, CF.sub.3, ASO, ASO.sub.2, AO--SO, AO--SO.sub.2, AcNH, AO--CO--NH, H.sub.2 NSO, HANSO, A.sub.2 NSO, H.sub.2 NSO.sub.2, HANSO.sub.2, A.sub.2 NSO.sub.2, H.sub.2 NCO, HANCO, A.sub.2 NCO, H.sub.2 NCS, HANCS, A.sub.2 NCS, ASONH, ASO.sub.2 NH, AOSONH, AOSO.sub.2 NH, ACO-alkyl, nitro-alkyl, cyanoalkyl, A--C(.dbd.NOH) or A--C(.dbd.NNH.sub.2),R.sup.8 and R.sup.9 are each H or A or together are .dbd.O or .dbd.S,R.sup.10 is H, Hal, CHO or CH.sub.2 OH,R.sup.11 is H, A, Ac or CH.sub.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: August 3, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rolf Gericke, Manfred Baumgarth, Ingeborg Lues, Jacques De Peyer, Rolf Bergmann
  • Patent number: 5231190
    Abstract: Squarylium compounds of the formula: ##STR1## wherein Q.sup.1 and Q.sup.2 are each independently a pyrylium, thiopyrylium, selenopyrylium, benzpyrylium, benzthiopyrylium or benzselenopyrylium nucleus, and R.sup.1 and R.sup.2 are each independently an aliphatic or cycloaliphatic group, can be prepared by reacting a squaric acid derivative of the formula: ##STR2## with a compound of the formula Q.sup.2 CH.sub.2 R.sup.2 in the presence of a base. The derivatives of Formula II may be prepared by condensing a 2,3,4,4-tetrahalocyclobut-2-en-1-one with a compound of the formula Q.sup.1 CH.sub.2 R.sup.1 in the presence of a base to produce a compound of the formula: ##STR3## wherein Q.sup.1 and R.sup.1 are as defined above, and X represents chlorine or bromine, and hydrolyzing the compound of Formula III. Alternatively, the derivatives of Formula II may be prepared by reacting a diester, monoacid chloride monoester or diacid chloride of squaric acid with a compound of the formula Q.sup.1 CH.sub.2 R.sup.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: July 27, 1993
    Assignee: Polaroid Corporation
    Inventors: Donald A. McGowan, Paulina P. Garcia, John W. Lee, Thomas K. Spencer, Stephen J. Telfer, Michael J. Zuraw
  • Patent number: 5227498
    Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a cycloaliphatic or aromatic ring) are useful as near infra-red absorbers.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: July 13, 1993
    Assignee: Polaroid Corporation
    Inventors: John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer