Chalcogen Attached Directly To Ring Nitrogen Of The Five-membered Hetero Ring By Nonionic Bonding (e.g., Pyrrolidine-n-oxides, Etc.) Patents (Class 548/542)
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Patent number: 5523464Abstract: The present invention relates to benzenesulfonamide derivatives represented by Formula (I): ##STR1## in which R.sup.1 and R.sup.2 independently represent hydrogen or lower alkanoyl; and R.sup.3 and R.sup.4 independently represent hydrogen, lower alkyl, cycloalkyl, substituted or unsubstituted polycycloalkyl, substituted aryl, or a substituted or unsubstituted heterocyclic group, or R.sup.3 and R.sup.4 are combined together with the adjacent nitrogen atom to form a substituted or unsubstituted aliphatic heterocyclic group, or a pharmaceutically acceptable salt thereof. The derivatives are useful as therapeutic agents for osteoporosis.Type: GrantFiled: June 30, 1994Date of Patent: June 4, 1996Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Iwao Kinoshita, Haruki Takai, Nobuo Kosaka, Katsura Sugawara, Akio Ishii, Hiroyuki Ishida, Katsushige Gomi
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Patent number: 5519134Abstract: Novel pyrrolidine monomers bearing various functional groups are used to prepare oligomeric structures. The pyrrolidine monomers can be joined via standard phosphate linkages including phosphodiester and phosphorothioate linkages. Useful functional groups include nucleobases as well as polar groups, hydrophobic groups, ionic groups, aromatic groups and/or groups that participate in hydrogen-bonding.Type: GrantFiled: January 11, 1994Date of Patent: May 21, 1996Assignee: Isis Pharmaceuticals, Inc.Inventors: Oscar L. Acevedo, Normand Hebert
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Patent number: 5514826Abstract: The present invention is directed to novel vinyl sulfenic acid derivatives, useful for the synthesis of benzo b!thiophenes, in particular 2-arylbenzo b!thiophenes.Type: GrantFiled: June 7, 1995Date of Patent: May 7, 1996Assignee: Eli Lilly and CompanyInventors: David W. Hoard, Wayne D. Luke
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Patent number: 5512701Abstract: The present invention is directed to a new process for the synthesis of vinyl sulfenic acid derivatives. These compounds are useful for the synthesis of benzo b!thiophenes, in particular 2-aryl-benzo b!thiophenes.Type: GrantFiled: June 7, 1995Date of Patent: April 30, 1996Assignee: Eli Lilly and CompanyInventors: David W. Hoard, Wayne D. Luke
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Patent number: 5498725Abstract: A 5-aminodihydropyrrole of the formula (1): ##STR1## in which R.sup.1 and R.sup.2 independently represent a hydrogen atom, a lower alkyl group or a lower haloalkyl group, or together form a C.sub.2 -C.sub.10 alkylene group optionally substituted with a halogen by reducing an oxidepyrrole of the formula (2): ##STR2## in which R.sup.1 and R.sup.2 are the same as defined above, with hydrogen in the presence of a catalyst.Type: GrantFiled: December 13, 1994Date of Patent: March 12, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Misuhiro Matsumoto, Kunihiko Fujita
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Patent number: 5493031Abstract: N-hydroxysuccinimide monohydrate is precipitated from an aqueous solution of N-hydroxysuccinimide. N-hydroxysuccinimide monohydrate is a new compound that can be used to produce anhydrous N-hydroxysuccinimide which is substantially pure. It can also be used as a substitute for N-hydroxysuccinimide when the presence of water is not detrimental.Type: GrantFiled: June 16, 1994Date of Patent: February 20, 1996Assignee: PPG Industries, Inc.Inventor: Cheruthur Govindan
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Patent number: 5466828Abstract: Chiral 3-cyanopyrrolidines of the following formula are disclosed, wherein R' is as defined herein. The compounds are useful as intermediates for naphthyridine and quinoline antibiotics.Type: GrantFiled: May 5, 1994Date of Patent: November 14, 1995Assignee: Warner-Lambert CompanyInventors: Victor Fedij, Mark J. Suto, James N. Wemple, James R. Zeller
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Patent number: 5461045Abstract: A fused benzeneoxyacetic acid derivative of the formula: ##STR1## wherein ##STR2## is (i) ##STR3## (ii) ##STR4## (iii) ##STR5## or (iv) ##STR6## A is (i) ##STR7## or (ii) ##STR8## R.sup.1 is hydrogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen, C.sub.1-6 alkyl or phenyl;R.sup.3 is(i) C.sub.1-15 alkyl,(ii) C.sub.1-8 alkyl substituted by one or two of benzene, C.sub.4-7 cycloalkane or 4-7 ring-membered monocyclic ring which contains one nitrogen atom or(iii) C.sub.10-15 condensed tricyclic ring;e is 3-5;f is 1-3;p is 0-4;q is 0-2;s is 0-3With the proviso that, ring(s) in R.sup.3 may be substituted by one to three of C.sub.1-4 alkyl, .sub.1-4 alkoxy, halogen atom, nitro or trihalomethyl. And, when D--B is the formula (iii) or (iv), --(CH2)p- or .dbd.CH--(CH2)s- is attached at the position of a or b on the ring.Type: GrantFiled: July 14, 1992Date of Patent: October 24, 1995Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Nobuyuki Hamanaka, Kanji Takahashi, Hidekado Tokumoto
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Patent number: 5453516Abstract: A process for preparing 5-membered ring heterocycles of the general formula I ##STR1## where R.sup.1 is methyl or hydroxyethyl,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are hydrogen, C.sub.1 - to C.sub.12 -alkyl, C.sub.2 - to C.sub.12 -alkenyl, aryl, C.sub.3 - to C.sub.8 -cycloalkyl, C.sub.1 - to C.sub.12 -alkoxy, halogen, C.sub.2 - to C.sub.20 -alkoxycarbonylalkyl, C.sub.2 - to C.sub.20 -alkylcarbonyloxy, formyl, C.sub.2 - to C.sub.20 -formylalkyl, benzoyl or --CH(OR.sup.3)(OR.sup.5), or R.sup.3 and R.sup.5 together are a C.sub.2 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by R.sup.4 or a .dbd.CH--CH.dbd.CH--CH.dbd. unit which is unsubstituted or monosubstituted to tetrasubstituted by R.sup.4,X is oxygen or N--R.sup.4by reacting 5-membered ring heterocycles of the general formula II ##STR2## where R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the abovementioned meanings and Y is hydrogen, acetyl or C.sub.2 - to C.sub.Type: GrantFiled: December 13, 1993Date of Patent: September 26, 1995Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rolf Pinkos
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Patent number: 5436352Abstract: The present invention provides metal chelating compounds, to chelates and chelate-targeting agent conjugates formed from the chelating compounds, and to methods for making and using these compositions. The chelating compounds incorporate two nitrogen atoms and three sulfur atoms ("N.sub.2 S.sub.3 "), two nitrogen atoms and four sulfur atoms ("N.sub.2 S.sub.4 "), or three nitrogen atoms and three sulfur atoms ("N.sub.3 S.sub.3 "). Metals, and metal oxides, capable of being chelated by the compounds include those that are radionuclides, such as .sup.99m Tc and .sup.186/188 Re.The targeting agent portion of the chelate-targeting agent conjugates provided includes antibodies, peptides, hormones, enzymes and biological response modifiers. Methods for making the conjugates are provided and encompass the addition of a metal, or metal oxide, to a chelating compound prior to attachment to a targeting agent as well as subsequent to the attachment.Type: GrantFiled: December 6, 1991Date of Patent: July 25, 1995Assignee: NeoRx CorporationInventors: Ananthachari Srinivasan, Alan R. Fritzberg, David S. Jones
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Patent number: 5431901Abstract: Selective isotopic-labeling of spin label compounds, used in electron spin resonance spectroscopy to detect, measure and monitor the presence of paramagnetic species, increases the sensitivity of the electron spin resonance technique in assays for paramagnetic species, such as the determination of oxygen tension in solution or in a biological sample, like a living organism. Spin label compounds, such as nitroxides, like 3-carbamoyl-2,2,5,5-tetramethyl-3-pyrroline-1-yloxyl (CTPO), are selectively, but not completely, isotopically-labeled, such as partially deuterated, to increase the sensitivity and reliability of assays employing electron spin resonance spectroscopic measurements.Type: GrantFiled: August 3, 1988Date of Patent: July 11, 1995Inventors: Howard J. Halpern, Beverly A. Teicher
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Patent number: 5426190Abstract: Acylated derivatives of N-hydroxysuccinimide are produced from succinic anhydride, hydroxylamine, and acylating agent without purification of the intermediate N-hydroxysuccinimide.Type: GrantFiled: June 16, 1994Date of Patent: June 20, 1995Assignee: PPG Industries, Inc.Inventors: Cheruthur Govindan, Suresh B. Damle
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Patent number: 5414089Abstract: Provided is a long chain carboxylic acid imide ester (I) represented by the following general formula (I) ##STR1## wherein W is a divalent long chain hydrocarbon group which may optionally be interrupted by one or more groups each independently selected from the group consisting of an oxygen atom, a sulfur atom, and a group of --N(R.sup.1)-- (R.sup.1 being a lower alkyl group) and X represents a divalent hydrocarbon group which may optionally be substituted, or salts thereof. The above long chain carboxylic acid imide ester or its salts is useful for modifying enzymes or proteins having biological activities to give their derivatives which have, while retaining most of the original biological activities, an extremely prolonged plasma half-life as compared with the proteins and have no antigenecities and can be administered to animals.Type: GrantFiled: August 16, 1993Date of Patent: May 9, 1995Assignee: Kuraray Co., Ltd.Inventors: Iwao Ebashi, Tetsuo Takigawa, Masayasu Inoue
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Patent number: 5407946Abstract: Components of formula (I): ##STR1## in which: R.sub.1 represents optionally substituted phenylsulfonyl, naphthylsulfonyl, quinolyl, or isoquinolyl,R.sub.2 represents hydrogen, optionally substituted phenyl, or optionally substituted 3-pyridyl or 2-pyridyl,R.sub.3 represents ##STR2## in which m is equal to 2, 3, or 4; n is equal to 4, 5, 6, or 7; and R represents hydrogen or alkyl, as thromboxane A.sub.2 receptor inhibitors or thromboxane A.sub.2 -synthase inhibitors, and pharmaceutical compositions containing the same.Type: GrantFiled: June 14, 1994Date of Patent: April 18, 1995Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Thierry Dubuffet, Olivier Muller, Michel Laubie, Tony Verbeuren
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Patent number: 5405967Abstract: Novel spin traps comprising 2-trifluoromethyl-1-DMPO or derivatives thereof have now been found. An effective synthesis method for these spin traps is also disclosed.Type: GrantFiled: October 22, 1993Date of Patent: April 11, 1995Assignee: Oklahoma Medical Research FoundationInventors: Edward G. Janzen, Yong-Kang Zhang
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Patent number: 5399716Abstract: Novel N-oxygenated arylpyrrole compounds which are effective for the control of insects, acarids and nematodes are described. A method for the insecticidal, acaricidal and nematicidal use of said compounds and a method for the preparation of said compounds are presented.Type: GrantFiled: March 26, 1993Date of Patent: March 21, 1995Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
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Patent number: 5393750Abstract: A compound of the general formula ##STR1## or a salt or complex thereof, in which X, Y and Z are all optionally substituted carbon atoms and R is hydrogen, optionally substituted hydrocarbyl or acyl or --COOR.sup.7 and R.sup.7 is hydrocarbyl has anti-microbial properties. Particular examples are compounds in which X is --CH.sub.2 -- or --C(CH.sub.3).sub.2 -- and Y and Z are both --CH.sub.2 -- or X is is --CH.sub.2 -- and Y and Z are carbon atoms of a benzene ring. The zinc complexes have useful properties.Type: GrantFiled: February 24, 1992Date of Patent: February 28, 1995Assignee: Zeneca, LimitedInventors: Mark R. James, Gordon A. Thomson
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Patent number: 5391765Abstract: The present invention relates to novel nitroxides which are useful for cholesterol lowering and as antioxidant agents. Also provided is a process for preparing the nitroxides of the present invention, pharmaceutical compositions, and a method of treating or inhibiting hypercholesterolemia, hyperlipidemia, atherosclerosis, and LDL oxidation which comprises administering to birds and mammals, in need of such treatment an effective amount of a compound of the present invention.Type: GrantFiled: April 16, 1993Date of Patent: February 21, 1995Assignee: Bristol-Myers Squibb CompanyInventors: Bradley C. Pearce, John J. Wright
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Patent number: 5387591Abstract: Compounds of formula (I): ##STR1## in which: R.sub.1 represents:optionally substituted alkyl,optionally substituted phenyl,pyridyl,optionally substituted phenylsulfonyl,acyl,optionally substituted benzoyl or pyridylcarbonyl,alkylaminocarbonyl or phenylaminocarbonyl,acylamino or benzoylamino,R2 represents:hydrogen,optionally substituted phenyl,optionally substituted 3-pyridyl or 2-pyridyl,R.sub.3 represents any one of the following groups: ##STR2## in which m is equal to 2, 3 or 4,n is equal to 4, 5, 6 or 7, and R represents hydrogen or alkyl.Type: GrantFiled: February 11, 1993Date of Patent: February 7, 1995Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Thierry Dubuffet, Olivier Muller, Michel Laubie, Tony Verbeuren
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Patent number: 5364844Abstract: Compounds of formula (I): ##STR1## A is a carbon-carbon bond or C.sub.1 -C.sub.3 alkylene; B is imino group or C.sub.1 -C.sub.2 alkylene; R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, heterocyclic or optionally substituted amino; R.sup.2 is optionally substituted phenyl or optionally substituted naphthyl; R.sup.3 is thiazolyl, isoxazolyl or imidazolyl; R.sup.4 is isopropyl or cyclohexyl; R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl, or, together with the carbon atom to which they are attached, C.sub.3 -C.sub.7 cycloalkyl; R.sup.7 is hydrogen, optionally substituted C.sub.1 -C.sub.6 alkyl group; and R.sup.8 is hydrogen or C.sub.1 -C.sub.4 alkyl. These compounds have renin-inhibitory and, hence, hypotensive activities. The invention also provides a method for the treatment or prophylaxis of hypertension induced by failures in the renin-angiotensin system.Type: GrantFiled: August 27, 1992Date of Patent: November 15, 1994Assignee: Sankyo Company, LimitedInventors: Yasuhiro Morisawa, Mitsuru Kataoka, Yuichiro Yabe, Hiroyuki Koike, Yasuteru Iijima, Hidekuni Takahagi, Tatsuo Kokubu, Kunio Hiwada
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Patent number: 5362477Abstract: Methods and compositions are disclosed for enhancing .sup.19 F magnetic resonance imaging which utilize .sup.19 F magnetic resonance contrast media having enhanced .sup.19 F relaxivity. Fluorine-containing compounds having enhanced .sup.19 F relaxation properties resulting from direct association with an unpaired spin are disclosed. The fluorine-containing compound is associated with the unpaired spin by covalent attachment of a stable free radical, by complexation of a fluorinated complexing agent with a paramagnetic metal ion, or by salt formation or charge neutralization of a paramagnetic ion.Type: GrantFiled: December 1, 1992Date of Patent: November 8, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: Dennis A. Moore, Max D. Adams, William P. Cacheris, David H. White, Muthunadar P. Periasamy, Raghavan Rajagopalan, Lynn A. deLearie, Steven R. Woulfe
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Patent number: 5356923Type: GrantFiled: October 22, 1992Date of Patent: October 18, 1994Assignee: Orion-yhtyma OyInventors: Reijo Backstrom, Erkki Honkanen, Atso Raasmaja, Inge-Birtt Linden
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Patent number: 5354871Abstract: Derivatives of 3,5-substituted pyrroline N-oxides having substituents in the 4-position have been prepared, with the 4-position substituents being selected from certain ester, polyether, and alkanoyl groups, the latter having components which bind to biological substrates. These specific derivatives are effective as spin traps for different types of free radicals to form persistent nitroxide adducts of extended half life. These adducts can be characterized by ESR spectrometry technique and provide information e.g. concerning the identification of free radicals.Type: GrantFiled: April 16, 1993Date of Patent: October 11, 1994Assignee: National Research Council of CanadaInventors: Prabhat Arya, David Griller
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Patent number: 5347017Abstract: The process for the preparation of chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted-pyrrolidines used as key intermediates for the preparation of naphthyridine and quinolone antibacterial agents which comprises reacting readily available chiral 1-substituted-3-pyrrolidinols to their corresponding chiral sulfonate esters; converting the sulfonate esters to chiral 1-substituted-3-cyanopyrrolidines having an inverse configuration, and then dialkylating the chiral cyanopyrrolidines with alkyl lithium in the presence of a Lewis acid without racemization at the asymmetric carbon atom is described.Type: GrantFiled: July 7, 1993Date of Patent: September 13, 1994Assignee: Warner-Lambert CompanyInventors: Victor Fedij, Mark J. Suto, James N. Wemple, James R. Zeller
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Patent number: 5346879Abstract: Plant growth regulators comprising, as an active ingredient, a substituted dicarboxylic acid derivative having the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as defined in the present specification, the substituted dicarboxylic acid derivatives, and processes for preparing the same, are disclosed. The plant growth regulators provided according to the present invention have a regulating activity on plant growth; more specifically, an action thereof of lowering the content of endogenous ethylene in a plant is utilized.Type: GrantFiled: April 14, 1993Date of Patent: September 13, 1994Assignee: Sumitomo Chemical Company LimitedInventors: Akio Manabe, Masato Mizutani, Naonori Hirata, Sachiko Uwayokote, Kazuo Izumi, Kenji Arai
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Patent number: 5340809Abstract: A compound selected from those of formula (I): ##STR1## with R.sub.1, R.sub.2 and n as defined in the description, and medicinal products containing the same useful in treating or in preventing a disorder resulting from cellular damages following upon ischemia, hypoxia, or anoxia.Type: GrantFiled: August 13, 1992Date of Patent: August 23, 1994Assignee: ADIR et CompagnieInventors: Michel Gaudry, Bruno Pfeiffer, Pierre Renard, Jean-Francois Renaud de la Faverie, Gerard Adam
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Patent number: 5336782Abstract: Provided is a long chain carboxylic acid imide ester (I) represented by the following general formula (I) ##STR1## wherein W is a divalent long chain hydrocarbon group which may optionally be interrupted by one or more groups each independently selected from the group consisting of an oxygen atom, a sulfur atom and a group of --N(R.sup.1)-- (R.sup.1 being a lower alkyl group) and X represents a divalent hydrocarbon group which may optionally be substituted, or salts thereof. The above long chain carboxylic acid imide ester or its salts is useful for modifying enzymes or proteins having biological activities to give their derivatives which have, while retaining most of the original biological activities, an extremely prolonged plasma half-life as compared with the proteins and have no antigenecities and can be administered to animals.Type: GrantFiled: April 23, 1992Date of Patent: August 9, 1994Assignee: Kuraray Co., Ltd.Inventors: Iwao Ebashi, Tetsuo Takigawa, Masayasu Inoue
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Patent number: 5324844Abstract: Poly(ethylene glycol)-N-succinimide carbonate and its preparation are disclosed. Polyethylene glycol (PEG) is converted into its N-succinimide carbonate derivative. This form of the polymer reacts readily with amino groups of proteins in aqueous buffers. The modified proteins have PEG-chains grafted onto the polypeptide backbone by means of stable, hydrolysis-resistant urethane (carbamate) linkages.Type: GrantFiled: January 8, 1992Date of Patent: June 28, 1994Assignee: Enzon, Inc.Inventor: Shmuel Zalipsky
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Patent number: 5310916Abstract: Trifunctional agents useful as inhibitors of A.sub.1 -Adenosine receptors may be formulated into pharmaceutical compositions. These agents are represented by formula (I): ##STR1## wherein X is CH or N, R is an isothiocyanate group, an amino group or --NHCO.sub.2 C(CH.sub.3).sub.3 and R.sup.1 is hydrogen, carboxyl, lower alkoxycarbonyl, aminocarbonyl, ##STR2## lower alkyl, optionally substituted with: --OH, --COOH, lower ester of COOH, carboxamide, NHCOCH.sub.3, NHCOCH.sub.2 Br, halo, dimethylamino, triethylammonium, NHCONH.sub.2, SO.sub.2 NH.sub.2, --SO.sub.3 H, or a reporter group, particularly a spectroscopic reporter group such as a fluorescent dye, photoaffinity probe, or spin label probe, coupled through an amide, sulfonamide, amine or thiourea linkage, biotinylamino- (optionally containing an .epsilon.-aminocaproyl spacer chain or similar spacer chain) or; R.sup.1 is CONH--R.sup.2 or NHCSNH--R.sup.2, wherein R.sup.Type: GrantFiled: August 24, 1990Date of Patent: May 10, 1994Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventors: Kenneth A. Jacobson, Gary L. Stiles, Daniel L. Boring
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Patent number: 5298513Abstract: For treatment of disorders of the central nervous system, the cardiovascular system or the intestinal tract, the new substituted basic 2-aminotetralins of the formula ##STR1## in which R.sup.1 represents hydrogen or alkyl,R.sup.2 represents hydrogen, alkyl or acyl, andR.sup.3 represents quinuclidine ora group of the formula --(CH.sub.2).sub.a --R.sup.4, --CH.sub.2 --CH.dbd.CH--(CH.sub.2).sub.b --R.sup.4, --CH.sub.2 --C.tbd.C--(CH.sub.2).sub.b --R.sup.4, ##STR2## wherein a denotes a number from 1 to 10,b denotes a number 0, 1, 2, 3 or 4,c denotes a number 0, 1 or 2,d denotes a number 2 or 3, andX denotes oxygen, sulphur or NR.sup.5,and their salts.Type: GrantFiled: May 29, 1992Date of Patent: March 29, 1994Assignee: Bayer AktiengesellschaftInventors: Rudolf Schohe, Thomas Glaser, Jorg Traber, George S. Allen
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Patent number: 5296494Abstract: Compounds of formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, m, n, and R are as defined in the Specification.Medicinal products containing the same are useful in the treatment or prevention of thrombotic afflictions due to their thromboxane A.sub.2 receptor antagonistic activity and their thromboxane A.sub.2 synthase inhibitory activity.Type: GrantFiled: December 18, 1992Date of Patent: March 22, 1994Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Patrick Hautefaye, Michel Laubie, Tony Verbeuren
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Patent number: 5292734Abstract: This disclosure describes novel 2, 3, 6 substituted quinazolinones having the formula: ##STR1## wherein X, R, and R.sup.6 are described in the specification which have activity as angiotensin II (AII) antagonists.Type: GrantFiled: April 23, 1993Date of Patent: March 8, 1994Assignee: American Cyanamid CompanyInventors: Jeremy I. Levin, Aranapakam M. Venkatesan
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Patent number: 5292726Abstract: Diacylpiperazines of general structure ##STR1## are: angiotensin II (A-II) antagonists selective for the type 2 (AT.sub.2) subtype useful in the treatment of cerebrovascular, cognitive, and CNS disorders; tachykinin receptor antagonists useful in the treatment of inflammatory diseases and pain or migraine; and calcium channel blockers useful in the treatment of cardiovascular conditions such as angina, hypertension or ischemia.Type: GrantFiled: May 19, 1992Date of Patent: March 8, 1994Assignee: Merck & Co., Inc.Inventors: Wallace T. Ashton, Conrad P. Dorn, William J. Greenlee, Malcolm MacCoss, Sander G. Mills, Mu T. Wu
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Patent number: 5290948Abstract: A process for converting 1,4- and 1,5-dicarbonyl sugars to pyrrolidine and piperidine amino sugars. Novel compounds resulting from this process are also described.Type: GrantFiled: September 17, 1990Date of Patent: March 1, 1994Assignee: McNeilab, Inc.Inventors: Allen B. Reitz, Ellen W. Baxter, Bruce E. Maryanoff
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Patent number: 5281617Abstract: N-succinimidyl and N-phthalimidyl esters of phenylalkanoic acid derivatives which are useful as inhibitors of HLE or HNE.Type: GrantFiled: February 5, 1993Date of Patent: January 25, 1994Assignee: Cortech, Inc.Inventors: Gary P. Kirschenheuter, John C. Cheronis
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Patent number: 5270339Abstract: There are described a phenoxybenzene derivative having the formula (I): ##STR1## wherein R.sup.1 is hydrogen atom; an alkyl group having 1 to 3 carbon atoms; --OR.sup.6 or a halogen atom,R.sup.2 is hydrogen atom, nitro group or amino group,R.sup.3 is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 5 carbon atoms, allyl group, vinyl group or --(CH.sub.2)n.sup.1 R.sup.7R.sup.4 is hydrogen atom, an alkyl group having 1 to 3 carbon atoms or --(CH.sub.2)n.sup.3 R.sup.25R.sup.5 hydrogen atom; an alkyl group having 1 to 3 carbon atoms; or phenyl group,X is ##STR2## wherein Y is oxygen atom or sulfur atom; or --CHR.sup.27 -- and line means a single bond or a double bond provided that n is 2 in case that the line means a single bond and n is 1 in case that the line means a double bond, ora pharmacologically acceptable salt thereof,a cognition enhancer comprising the same as an effective ingredient andan antidepressant comprising the same as an effective ingredient.Type: GrantFiled: December 3, 1992Date of Patent: December 14, 1993Assignee: Kanagafuchi Kagaku Kogyo Kabushiki KaishaInventors: Kozo Yamamoto, Yoshihide Fuse, Hideyuki Kishida, Naoko Yasuhara, Toshiaki Miwa, Ikuo Katsumi, Takayoshi Hidaka
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Patent number: 5264204Abstract: Methods and compositions are disclosed for enhancing magnetic resonance imaging which utilize hydrophilic free radical compounds as magnetic resonance contrast media. Typical magnetic resonance contrast media within the scope of the present invention include stable hydrophilic free radicals having a hydrophilic moiety, such as polyhydroxyalkyl groups and heterocyclic amino-alcohols such as dihydroxypyrrolidine, dihydroxypiperidine, and trihydroxypiperidine, and a stable free radical moiety, such as a nitroxide, phenoxy, or phenoxazinyl free radical moiety.Type: GrantFiled: April 30, 1992Date of Patent: November 23, 1993Assignee: Mallinckrodt Medical, Inc.Inventors: William P. Cacheris, T. Jeffrey Dunn, Lynn deLearie, Youlin Lin, Jeffrey A. Levine
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Patent number: 5256397Abstract: Nitroxides useful as MRI enhancing agents are of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each are alkyl of 1-4 carbon atoms; and R is --alk--COO.sup.- M.sup.+ or --B--N.sup.+ (Alk).sub.3 Hal.sup.- in which alk is alkylene of 1-8 carbon atoms, B is a divalent bond or alkylene of 1-8 carbon atoms, M.sup.+ is an ammonium or metal ion, Alk is alkyl of 1-8 carbon atoms or a corresponding alkyl group substituted by a free or esterified hydroxy group, and Hal.sup.- is Cl.sup.-, Br.sup.- or I.sup.-.Type: GrantFiled: April 2, 1992Date of Patent: October 26, 1993Assignee: M.R.I., Inc.Inventor: Gerald M. Rosen
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Patent number: 5254715Abstract: A compound of the following general formula which is useful in treating hypocholesterolemia and atherosclerosis: ##STR1## wherein X is oxygen or sulfur; R is hydrogen, alkyl having from 1 to 8 carbon atoms, or benzyl; R.sub.1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, an aralkyl group, a heterocyclic group, or a hydrocarbon chain of from 1 to 20 carbon atoms which is saturated or contains 1 to 3 double bonds and each of R.sub.2 and R.sub.3 is selected from hydrogen, provided both are not hydrogen, an aralkyl group, a hydrocarbon chain of from 1 to 20 carbon atoms which is saturated or contains 1 to 3 double bonds, an w-substituted alkylC.sub.1-6, a heterocyclic group, phenyl, substituted phenyl or NR.sub.2 R.sub.3 taken together form a monocyclic heterocyclic group.Type: GrantFiled: August 19, 1991Date of Patent: October 19, 1993Assignee: Warner-Lambert CompanyInventors: Joseph A. Picard, Drago R. Sliskovic
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Patent number: 5250702Abstract: A compound of the formula II: ##STR1## wherein n is an integer of 2 to 10,A' is a bivalent linking group formed by reacting both the reactive groups of a cross linking reagent, andB is a residue of a polypeptide compound,and physiologically acceptable salts thereof are disclosed. Such compound is useful as a non-radioactive carrier for radioactive metal elements.Type: GrantFiled: April 26, 1991Date of Patent: October 5, 1993Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Susumu Kondo, Miki Kurami, Makoto Azuma
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Patent number: 5247084Abstract: Compounds presented by the general formula: ##STR1## [wherein when Y is oxygen, R.sup.2 is H, alkyl, alkoxy, alkoxymethyl, --COOR.sup.3, --CH.sub.2 COOR.sup.3, --CH=CH--COOR.sup.3, halogen, --CF.sub.3, --COR.sup.4, --OCOR.sup.4, --CH.sub.2 OCOR.sup.4, --SO.sub.2 R.sup.4, --OSO.sub.2 R.sup.4, --CONR.sup.5 R.sup.6, --OCONR.sup.5 R.sup.6, --SO.sub.2 NR.sup.5 R.sup.6, --CONH--SO.sub.2 NR.sup.5 R.sup.6, --NHSO.sub.2 R.sup.7, --NO.sub.2, --OH, --CH.sub.2 OH, guanidino, benzyloxy, guanidinophenylthiomethyl, morpholinosulfonylphenoxymethyl, pyridyloxymethyl, or (1,1-dioxothiazol-3-yl)carbonyl, or when Y is sulfur, R.sup.2 is H, alkyl, alkoxy, halogen, --COOR.sup.3, --CH.sub.2 COOR.sup.3, --NO.sub.2, or --SO.sub.2 NR.sup.5 R.sup.6, and n represents an integer of one to five, and when n represents more than two, each of R.sup.2 may be the same group or the different group.Type: GrantFiled: September 26, 1991Date of Patent: September 21, 1993Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Yoshinobu Arai, Hiroyuki Ohno
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Patent number: 5241078Abstract: This invention discloses heterobifunctional coupling agents for making a wide array of molecular conjugates. The agents contain a sterically hindered thiol, linked through a spacer arm to a second group reactive toward nucleophiles such as 1.degree. and 2.degree. amines or reactive thiols that are present on biological and organic materials. The coupling agents are useful for making conjugates containing a sterically hindered linkage.Type: GrantFiled: February 14, 1992Date of Patent: August 31, 1993Assignee: Cetus OncologyInventors: Margaret Moreland, I. Lawrence Greenfield, Danute E. Nitecki
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Patent number: 5229523Abstract: 2-Methyl-5-hydroxymethyl- and 2,5-dimethyl-3,4-dihydroxypyrrolidines, 2,5-dimethyl-3,4-dihydroxypyrrolidines, their processes of preparation and use are disclosed. 5-Azido-5-deoxyhexulose-1-phosphate compounds and processes of making the same are also disclosed.Type: GrantFiled: February 13, 1992Date of Patent: July 20, 1993Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Kun-Chin Liu
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Patent number: 5228899Abstract: Plant growth regulators comprising, as an active ingredient, a substituted dicarboxylic acid derivative having the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, D and G are the same as defined in the present specification, the substituted dicarboxylic acid derivatives, and processes for preparing the same, are disclosed. The plant growth regulators provided according to the present invention have a regulating activity on plant growth; more specifically, an action thereof of lowering the content of endogenous ethylene in a plant is utilized.Type: GrantFiled: August 24, 1990Date of Patent: July 20, 1993Assignee: Sumitomo Chemical Company LimitedInventors: Yoshikazu Itoh, Akio Manabe, Masato Mizutani, Naonori Hirata, Sachiko Uwayokote, Kazuo Izumi, Kenji Arai
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Patent number: 5217982Abstract: This invention relates to compounds which are derivatives of cyclopentane which are useful as antihypertensive agents, to pharmaceutical compositions including such compounds, and to their use in treating hypertension.Type: GrantFiled: November 15, 1990Date of Patent: June 8, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Cynthia A. Fink, Alfred P. Spada
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Patent number: 5218116Abstract: Procedure for the preparation of nitroxyl radicals of sterically hindered amines, consisting of the reaction of amines with hydrogen peroxide in the presence of a titanium containing catalyst, particularly in the presence of titanium silicalites.The catalyst can be recovered at the end of the reaction and recycled.Type: GrantFiled: November 29, 1991Date of Patent: June 8, 1993Assignee: Enichem Synthesis S.p.A.Inventors: Carlo Neri, Silvestro Costanzi, Rosa M. Riva, Mariangela Angaroni
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Patent number: 5204341Abstract: 1-arylsulphonyl-2-pyrrolidone derivatives for treating spasmodic disorders in gastro-enterology, in gynaecology, in obstetrics, in urology; intermediates in the preparation of such products; methods for preparing such products and pharmaceutical preparations containing such products.Type: GrantFiled: December 11, 1991Date of Patent: April 20, 1993Assignee: Roussel UclafInventors: Emilio Toja, Carla Bonetti, Fernando Barzaghi, Giulio Galliani
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Patent number: 5196548Abstract: Diazabicyclo[2.2.1]heptane intermediates are prepared from 4-hydroxy-L-proline in a five step procedure, or from allo-4-hydroxy-D-proline, through a novel 2-(C.sub.1 -C.sub.6)alkyl-5-substituted-2,5-diazabicyclo[2.2.1]heptane intermediate. The diazabicycloheptanes are of use in the preparation of antibiotic quinolones.Type: GrantFiled: July 2, 1992Date of Patent: March 23, 1993Assignee: Pfizer Inc.Inventors: Tamim F. Braish, Darrell E. Fox
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Patent number: 5177069Abstract: The present invention provides a novel class of naphthylsulfonylalkanoic acid compounds such as a structure corrresponding to the formula: ##STR1## or a pharmaceutically acceptable salt thereof. A present invention naphthylsulfonylalkanoic acid compound is useful for prevention or treatment of irritable bowel syndrome, biliary dyskinesia and acute pancreatitis.Type: GrantFiled: December 6, 1990Date of Patent: January 5, 1993Assignee: Kissei Pharmaceutical Co., Ltd.Inventors: Makio Kitazawa, Masuo Akahane, Yasushi Nakano, Atsushi Tsubaki, Kazuaki Sato, Masaaki Ban, Michihiro Kobayashi
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Patent number: 5164514Abstract: Compounds useful for the treatment of patients suffering from muscle spasms of the formula (I) ##STR1## in which R represents the radical ##STR2## in which R.sub.1, in any position on the phenyl nucleus, represents a linear, branched or cyclic alkyl, alkenyl or alkynyl, containing up to 8 carbon atoms, or the radical ##STR3## in which R.sub.2 and R.sub.3, identical or different each represents a hydrogen atom, a linear alkyl, alkenyl or alkynyl, containing up to 8 carbon atoms, or form together with the nitrogen atom to which they are joined, a heterocyclic radical optionally containing another heteroatom, or NO.sub.2, or OR', R' representing hydrogen, a linear, branched or cyclic alkyl containing up to 8 carbon atoms, or aryl containing up to 14 carbon atoms, or an SR.sub.4 or S(O)R.sub.5 radical, R.sub.4 and R.sub.5 representing a linear, branched or cyclic alkyl, alkenyl or alkynyl, containing up to 8 carbon atoms, or R represents naphthyl, optionally substituted by an R.sub.Type: GrantFiled: September 18, 1990Date of Patent: November 17, 1992Assignee: Roussel UclafInventors: Giulio Galliani, Fernando Barzaghi, Michel Fortin, Carlo Gorini, Emilio Toja