Nitrogen In Phenolic Moiety Patents (Class 560/136)
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Patent number: 10882819Abstract: The present invention relates to novel intermediate(s), which are useful for the preparation of Rivastigmine compound of formula (I) and its pharmaceutically acceptable salts. The present invention further relates to the processes for the preparation of such novel intermediate(s) and preparation of Rivastigmine using such novel intermediate(s).Type: GrantFiled: September 25, 2019Date of Patent: January 5, 2021Assignee: Cadila Corporate CampusInventors: Jhillu Singh Yadav, Gyanchander Eppa, Pranav Rameshbhai Vachharajani, Nutan Bharatbhai Vekariya, Chetan Umeshbhai Bhavsar, Rajiv Indravadan Modi, Bakulesh Mafatlal Khamar
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Patent number: 8637713Abstract: A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and transfer hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate.Type: GrantFiled: December 5, 2012Date of Patent: January 28, 2014Assignee: Novartis AGInventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
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Patent number: 8420846Abstract: Disclosed herein are novel intermediates and process for large scale production of (S)-3-[(1-dimethylamino)ethyl]phenyl-N-ethyl-N-methyl-carbamate (rivastigmine) or its pharmaceutically acceptable salts employing the novel intermediates. Further provided are methods for producing the novel intermediates thereof.Type: GrantFiled: August 25, 2009Date of Patent: April 16, 2013Assignee: Jubilant Life Sciences LimitedInventors: Shailendra Kumar Dubey, Vikas Bansal, Kamaljeet Pannu, Sushil Kumar Dubey
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Patent number: 8415508Abstract: A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and transfer hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate.Type: GrantFiled: December 17, 2009Date of Patent: April 9, 2013Assignee: Novartis AGInventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
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Patent number: 8324429Abstract: The present invention provides N-methylethylcarbamino-3-[(S)-1-(methyl-[(S)-1-phenylethyl]amino)ethyl]phenyl ester represented by formula (II) and its preparation method. The present invention also provides (S)-1-(3-methoxyphenyl)-N-methyl-N—[(S)-1-phenylethyl]ethylamine and 3-[(S)-1-(methyl-[(S)-1-phenylethyl]amino)ethyl]phenol as intermediates of the compound represented by formula (II), and the use of the compound represented by formula (II) for preparing rivastigmine used for treating Alzheimer disease.Type: GrantFiled: January 10, 2008Date of Patent: December 4, 2012Assignees: Shanghai Institute of Pharmaceutical Industry, Zhejian Hisun Pharmaceutical Co., Ltd.Inventors: Fuli Zhang, Meng Hu, Meihua Xie, Anping Lai, Rentong Sun, Daoxin Chen, Rusheng Bao, Hua Bai
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Patent number: 8283453Abstract: The present invention provides a method for selectively placing carbon nanotubes on a substrate surface by using functionalized carbon nanotubes having an organic compound that is covalently bonded to such carbon nanotubes. The organic compound comprises at least two functional groups, the first of which is capable of forming covalent bonds with carbon nanotubes, and the second of which is capable of selectively bonding metal oxides. Such functionalized carbon nanotubes are contacted with a substrate surface that has at least one portion containing a metal oxide. The second functional group of the organic compound selectively bonds to the metal oxide, so as to selectively place the functionalized carbon nanotubes on the at least one portion of the substrate surface that comprises the metal oxide.Type: GrantFiled: August 14, 2009Date of Patent: October 9, 2012Assignee: International Business Machines CorporationInventors: Ali Afzali-Ardakani, Phaedon Avouris, James B. Hannon, Christian Klinke
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Patent number: 8049031Abstract: New solid forms of fesoterodine fumarate are described. In particular, amorphous fesoterodine fumarate, characterized by a powder X-ray diffraction spectrum as shown in FIG. 1 and by an IR spectrum as shown in FIG. 2 is described. Also fesoterodine fumarate in crystalline form I, characterized by a powder X-ray diffraction spectrum as shown in FIG. 3, by a DSC profile as shown in FIG. 4, by an IR spectrum as shown in FIG. 5, by a solid state 13C-NMR spectrum as shown in FIG. 6 and by a Raman spectrum as shown in FIGS. 7, 8 and 9 is described.Type: GrantFiled: December 10, 2009Date of Patent: November 1, 2011Assignee: Chemi S.p.A.Inventors: Umberto Ciambecchini, Maurizio Zenoni, Stefano Turchetta
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Patent number: 8013181Abstract: There are provided processes for making rivastigmine. In one embodiment, the process includes reacting S-(?)-[1-(3-hydroxyphenyl)ethyl]dimethylamine with N-ethyl-N-methyl carbamoyl chloride in the presence of an organic base to obtain a free base of rivastigmine.Type: GrantFiled: April 10, 2008Date of Patent: September 6, 2011Assignees: Dr. Reddy's Laboratories Limited, Dr. Reddy's Laboratories, Inc.Inventors: Venkata Naga Brahmeswara Rao Mandava, Venkata Reddy Vajrala, Ganesh Varanasi, Vijay Kumar Adla, Mukund Reddy Jambula, Vijaypal Reddy Kanumathi Reddy
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Publication number: 20100286437Abstract: The present invention provides N-methylethylcarbamino-3-[(S)-1-(methyl-[(S)-1-phenylethyl]amino)ethyl]phenyl ester represented by formula (II) and its preparation method. The present invention also provides (S)-1-(3-methoxyphenyl)-N-methyl-N—[(S)-1-phenylethyl]ethylamine and 3-[(S)-1-(methyl-[(S)-1-phenylethyl]amino)ethyl]phenol as intermediates of the compound represented by formula (II), and the use of the compound represented by formula (II) for preparing rivastigmine used for treating Alzheimer disease.Type: ApplicationFiled: January 10, 2008Publication date: November 11, 2010Inventors: Fuli Zhang, Meng Hu, Meihua Xie, Anping Lai, Rentong Sun, Daoxin Chen, Rusheng Bao, Hua Bai
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Publication number: 20100190725Abstract: Compounds of formula (I) or formula (II) have dopaminergic activity: wherein: R1 is a carboxyl, carboxyl ester, or carboxamide group; R2 is a group —C(?O)—NR3R4, or —S(?O)2—NR3R4; R3 and R4 are independently selected from hydrogen, optionally substituted C1-C6 alkyl, (C1-C5 fluoroalkyl)-CH2—, -Q, and —CH2Q, wherein Q is an optionally substituted monocyclic carbocyclic or heterocyclic ring of (3) to (6) ring atoms; or R3 and R4 together with the nitrogen to which they are attached form an optionally substituted monocyclic cycloalkyl or non-aromatic heterocyclic ring of (3) to (8) ring atoms; R5 is hydrogen, or a natural or non-natural alpha amino acid residue linked via a peptide bond; R6 is hydrogen or a group R7C(?O)—; and R7 is C1-C6 alkyl, C1-C6 fluoroalkyl or cyclopropyl.Type: ApplicationFiled: July 4, 2008Publication date: July 29, 2010Applicant: PROXIMAGEN LTD.Inventor: Christopher Hobbs
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Patent number: 7683205Abstract: The present invention relates to an improved process for preparation of Rivastigmine of formula (I) or pharmaceutically acceptable salts thereof comprising a step of N-methylation of compound of formula (III), wherein R1=R2=H or R1=H and R2=CH3 or an acid addition salt thereof, using paraformaldehyde in the presence of Raney Nickel and hydrogen in a suitable solvent to obtain compound of formula (II).Type: GrantFiled: October 31, 2006Date of Patent: March 23, 2010Assignee: Alembic LimitedInventors: Pandurang Balwant Deshpande, Kishore Khemani, Bharat Becharbhai Boda, Tushar Rajnikant Shah, Hitarth Harshendu Acharya, Parven Kumar Luthra
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Patent number: 7649114Abstract: The invention concerns a method for the isolation of a stereoisomer from a mixture comprising the two stereoisomers of the general formulae (I-A) and (I-A?) and/or the two stereoisomers of the general formulae (I-B) and (I-B?) in which R1, R2 and R3, identical or different, are selected from the group consisting of —H, —F, —Cl, —C1-C6-alkyl, —S—C1-C6-alkyl, —OH, —O—C1-C6-alkyl, —O—C1-C6-alkylenephenyl, —OCO—C1-C6-alkyl, —OCON(C1-C6-alkyl)2 and —O—SiR8R9R10 (in which R8, R9 and R10, identical or different, are —C1-C6-alkyl or -phenyl); R4 is —H or —C1-C6-alkyl; R5 is —C1-C6-alkyl; and R6 and R7, identical or different, are —H or —C1-C6-alkyl; or their salts with organic or inorganic acids; comprising the step (a) manipulating the mixture ratio of the stereoisomers in the mixture so that at least one of the stereoisomers is present in an enantiomeric excess.Type: GrantFiled: May 29, 2006Date of Patent: January 19, 2010Assignee: Gruenenthal GmbHInventors: Helmut Heinrich Buschmann, Wolfgang Hell
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Patent number: 7531684Abstract: A process for making aminoalkylphenyl carbamates, especially rivastigmine, can use less severe conditions using bis(p-nitrophenyl)carbonate (IX) as a phenol activator compound.Type: GrantFiled: September 28, 2007Date of Patent: May 12, 2009Assignee: Synthon BVInventors: Henar Tejedor Vinent, Arjanne Overeem, Lambertus Thijs
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Publication number: 20080306280Abstract: This invention relates to a process for the preparation of an aminoalkyl phenyl carbamate compound of formula 1, wherein R1 and R2 independently are hydrogen or C1-6 alkyl; R3 and R4 are the same or different and each is a lower alkyl; or R3 and R4 together with the nitrogen to which they are attached form a cyclic moiety of a three to eight-member ring, with or without a hetero atom like nitrogen or oxygen; R5 and R6 independently are hydrogen, linear, branched or cyclic C1-6 alkyl, allyl, propargyl or benzyl; or R5 and R6 together with the nitrogen to which they are attached form a cyclic moiety of three to eight member ring, with or without a hetero atom like nitrogen or oxygen; the carbon center marked with “*” is racemic or enantiomerically enriched (R)- or (S)-configuration; and pharmaceutically acceptable addition salts, and crystalline and amorphous forms thereof comprising the steps of: i) converting an amine R5R6NH to a carbamoylimidazolium salt of formula 3 wherein R5 and R6 areType: ApplicationFiled: June 11, 2007Publication date: December 11, 2008Inventors: Mohammed Abdul Raheem, Zhi-Xian Wang, Eckardt C.G. Wolf
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Patent number: 7405239Abstract: The invention relates to acylhydrazone derivatives of formula (I), which are SGK inhibitors and can be used for the treatment of diseases and afflictions associated with SGK, such as diabetes, obesity, metabolic syndrome (dyslipidaemia), systematic and pulmonary hypertension, cardiovascular diseases and kidney diseases and in general for all types of fibroses and inflammatory processes. In said formula: R1 and R5 independently of one another represent H, OH, OA, OAc or methyl; R2, R3, R4, R6, R7, R8, R9 and R10 independently of one another represent H, OH, OA, OAc, OCF3, Hal, NO2, CF3, A, CN, OSO2CH3, SO2CH3, NH2, or COOH; R11 represents H or CH3; A represents an alkyl comprising 1, 2, 3, or 4 C atoms; X represents CH2, CH2CH2, OCH2 or —CH(OH)— and Hal represents F, Cl, Br or I.Type: GrantFiled: September 16, 2004Date of Patent: July 29, 2008Assignee: Merck Patent GmbHInventors: Rolf Gericke, Norbert Beier, Oliver Poeschke, Lars Burgdorf, Helga Drosdat, Florian Lang
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Patent number: 7385076Abstract: A process for the preparation of compound of formula (I); wherein R1 is hydrogen, linear, branched or cyclic lower alkyl, cyclohexyl, allyl, propargyl or benzyl; R2 is hydrogen, methyl, ethyl or propyl; or R1 and R2 together with the nitogen to which they are attached form a cyclic moiety of three to eight-membered ring, with or without a hetero atom like nitrogen or oxygen; R3 is hydrogen or lower alkyl; R4 and R5 are the same or different and each is a lower alkyl; comprising reacting compound of formula (II); wherein R3, R4 and R5 are as defined above, with compound of formula (III); wherein R1 and R2 are as defined above, in the presence of a base, and further resolving the compound of formula (I) to obtain (S)-isomer of compound of formula (I), substantially free of R-isomerType: GrantFiled: June 2, 2003Date of Patent: June 10, 2008Assignee: Sun Pharmaceutical Industries LimitedInventors: Hetalkumar Virendrabhai Patel, Rajamannar Thennati
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Patent number: 6927303Abstract: The present invention relates to a tetrafluorobenzyl derivative and a pharmaceutical composition for prevention and treatment of acute and chronic neurodegenerative disease in central nervous system and ophthalmic diseases containing the same. The tetrafluorobenzyl derivative of the present invention can effectively be used to prevent and treat chronic neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease and Huntington's disease, degenerative brain disease such as epilepsy and ischemic brain disease such as stroke.Type: GrantFiled: June 19, 2003Date of Patent: August 9, 2005Assignee: Neurotech Co., Ltd.Inventors: Byoung-Joo Gwag, Sung-Hwa Yoon, Ho-Sang Moon, Eun-Chan Park, Seok-Joon Won, Young-Ae Lee, Hae-Un Lee
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Patent number: 6835748Abstract: The present invention is in particular related to the use of rivastigmine in the manufacture of a medicament for the treatment of ocular disorders.Type: GrantFiled: January 23, 2003Date of Patent: December 28, 2004Assignee: Novartis AGInventor: David Goldblum
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Publication number: 20040102652Abstract: The use of the optically active forms of 5,6-dihydroxy-2-methylaminotetralin and acyl esters thereof as medicaments for cardiovascular diseases a process for the preparation thereof and their use in pharmaceutical compositions.Type: ApplicationFiled: June 9, 2003Publication date: May 27, 2004Inventors: Gabriele Amari, Maurizio Del Canale, Roberta Razzetti, Pier Alessandro Monici Preti, Ivano Rondelli
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Patent number: 6730700Abstract: Disclosed are 3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical compositions containing such compounds. The 3,4,5-trisubstituted aryl nitrone compounds have formula (I); where R1-R4 are as defined in the specification. The disclosed compositions are useful as therapeutics for inflammation-related conditions in mammals, such as arthritis, and as analytical reagents for detecting free radicals.Type: GrantFiled: July 15, 2002Date of Patent: May 4, 2004Assignee: Renovis, Inc.Inventors: L. David Waterbury, Allan L. Wilcox, John M. Carney, Farah Mavandadi, Albert Danielzadeh
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Publication number: 20040067981Abstract: A compound of the formula (I): 1Type: ApplicationFiled: July 28, 2003Publication date: April 8, 2004Applicant: SANKYO COMPANY, LIMITEDInventors: Kazuo Koyama, Shinji Marumoto, Narihiro Toda, Hiroshi Kogen, Keiko Suzuki
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Publication number: 20040010038Abstract: The subject invention provides derivatives of propargylamino indan (PAI) and propargylamino tetralin that selectively inhibit monoamine oxidase (MAO) in the brain, having the structure: 1Type: ApplicationFiled: February 27, 2003Publication date: January 15, 2004Inventors: Eran Blaugrund, Yaacov Herzig, Jeffrey Sterling
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Patent number: 6573297Abstract: A (2-substituted oxyphenyl)alkanamide derivative or a salt thereof expressed by the following Formula (I): wherein one of A and B is a hydrocarbon group of C3-30 expressed by R1 and the other is —(CH2)n-NR2R3; Z is —CO— or —CONR6—; R2 and R3 individually represent H, lower alkyl or benzyl, or —NR2R3 may be a heterocycle having 3-7 members; wherein —CONR5—(CH2)n-NR2R3 or —CONR6—(CH2)n-NR2R3 may be the following Group (II): wherein ring Y is a heterocycle of 6 or 7 members; R4 is selected from the group consisting of H, halogen, lower alkyl, lower acyl and etc; R5 and R6 are individually H, lower alkyl, lower acyl or lower alkylcarbamoyl, or may form a part of said Group(II); 1 is 0 or 1; m is 1 or 2; and n is an integer of 0-5.Type: GrantFiled: October 29, 2001Date of Patent: June 3, 2003Assignee: Shiseido Co., Ltd.Inventors: Koji Kobayashi, Hirotada Fukunishi, Tokuro Iwabuchi
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Patent number: 6534541Abstract: The present invention is in particular related to the use of rivastigmine in the manufacture of a medicament for the treatment of ocular disorders.Type: GrantFiled: October 11, 2000Date of Patent: March 18, 2003Assignee: Novartis AGInventor: David Goldblum
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Patent number: 6512136Abstract: New compounds of formula I are described The compounds have potentially valuable pharmaceutical properties in the treatment of some central and peripheral nervous system disorders, where a reduction in the O-methylation of catecholamines may be of therapeutical benefit, such as Parkinson's disease and parkinsonian disorders, gastrointestinal disturbances, edema formation states and hypertension.Type: GrantFiled: December 17, 1999Date of Patent: January 28, 2003Assignee: Portela & C.A., S.A.Inventors: Jan Benes, Patricio Manuel Viera Araujo Soares Da Silva, David Alexander Learmonth
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Publication number: 20020188020Abstract: This invention is directed to compounds of the following formula: 1Type: ApplicationFiled: August 31, 2001Publication date: December 12, 2002Applicant: Yissum Research Development Company of the Hebrew University of JerusalemInventors: Michael Chorev, Tamar Goren, Yacov Herzig, Jeffrey Sterling, Marta Weinstock-Rosin, Moussa B.H. Youdim
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Patent number: 6342523Abstract: Disclosed are 3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical compositions containing such compounds. The 3,4,5-trisubstituted aryl nitrone compounds have the formula: where R1-R4 are as defined in the specification. The disclosed compositions are useful as therapeutics for inflammation-related conditions in mammals, such as arthritis, and as analytical reagents for detecting free radicals.Type: GrantFiled: December 1, 1999Date of Patent: January 29, 2002Assignee: Centaur Pharmaceuticals, Inc.Inventors: L. David Waterbury, Allan L. Wilcox, John M. Carney, Farah Mavandadi, Albert Danielzadeh
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Patent number: 6303650Abstract: This invention is directed to compounds of the following formula wherein when a is O, b is 1 or 2; when a is 1, b is 1, m is from 0-3 X is O or S, Y is halogeno, R1 is hydrogen C1-4 alkyl, R2 is hydrogen, C1-4 alkyl, or optionally substituted propargyl and R3 and R4 are each independently hydrogen, C1-8 alkyl, C6-12 aryl, C6-12 aralkyl each optionally substituted. This invention is also directed to the use of these compounds for treating depression, Attention Deficit Disorder (ADC), Attention Deficit and Hyperactivity Disorder (ADHD), Tourette's Syndrome, Alzheimer's Disease and other dementia's such as senile dementia, dementia of the Parkinson's type, vascular dementia and Lewy body dementia. This invention is further directed to a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.Type: GrantFiled: June 18, 1999Date of Patent: October 16, 2001Assignees: Yissum Research Development Company of the Hebrew University of Jerusalem, Technion Research and Development Foundation, Ltd., Teva Pharmaceutical Industries, Ltd.Inventors: Michael Chorev, Tamar Goren, Yacov Herzig, Jeffrey Sterling, Marta Weinstock-Rosin, Moussa B. H. Youdim
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Patent number: 6251938Abstract: This invention is directed to compounds of the following formula: wherein m is from 0-4; X is O or S; Y is halogeno; R1 is hydrogen or C1-4 alkyl; R2 is hydrogen, C1-4 alkyl or optionally substituted propargyl; and R3 and R4 are each independently hydrogen, C1-8 alkyl, C6-12 aryl, C6-12 cycloalkyl or C6-12 aralkyl, R5 is hydrogen or C1-4 alkyl; and pharmaceutically acceptable salts thereof, provided that when X is O, R2 is optionally substituted propargyl. This invention is also directed to the use of these compounds for treating depression, Attention Deficit Disorder (ADD), Attention Deficit and Hyperactivity Disorder (ADHD), Tourette's Syndrome, Alzheimer's Disease and other dementia's such as senile dementia, dementia of the Parkinson's type, vascular dementia and Lewy body dementia. This invention is further directed to a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.Type: GrantFiled: June 18, 1999Date of Patent: June 26, 2001Assignees: Teva Pharmaceutical Industries, Ltd.,, Technion Research and Development Foundation, Ltd.,, Yissum Research Development Company of the Hebrew University of JerusalemInventors: Michael Chorev, Tamar Goren, Yacov Herzig, Jeffrey Sterling, Marta Weinstock-Rosin, Moussa B. H. Youdim
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Patent number: 6153646Abstract: A family of platinum complexes which are stable and exhibit anticancer activity.Type: GrantFiled: December 9, 1998Date of Patent: November 28, 2000Assignee: Yoshinori KidaniInventors: Yoshinori Kidani, Rolland-Yves Mauvernay, Teruko Irie
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Patent number: 6022989Abstract: A process is disclosed for the preparation of an N-acylated activated derivative of an amino acid or a salt thereof.Type: GrantFiled: June 28, 1996Date of Patent: February 8, 2000Assignee: Abbott LaboratoriesInventors: Patricia A. Oliver, Arthur J. Cooper, Joseph B. Paterson, Jr., Denton C. Langridge, Jieh-Heh J. Tien
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Patent number: 6013606Abstract: Substituted cinnamic oxime derivatives I and cinnamic hydroxamide derivatives II ##STR1## (R.sup.1= halogen, NO.sub.2, CN, CF.sub.3 ; R.sup.2 =H, halogen; R.sup.3= H, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, hydroxy-C.sub.1 -C.sub.6 -alkyl;R.sup.4= H, halogen, CN, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl orR.sup.3 +R.sup.4 =chemical bond;Y=--O--, --S--, --O--CO--, --O--SO.sub.2 -- or chemical bond;Y'=--O-- or --S--;R.sup.5= unsubst. or subst. C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, unsubst. or subst. phenyl or phenyl-C.sub.1 -C.sub.6 -alkyl, or, if Y is --O--, --S-- or a chemical bond, is (C.sub.1 -C.sub.6 -alkyl)carbonyl or (C.sub.1 -C.sub.6 -alkoxy)carbonyl; or, if Y is a chemical bond, is hydrogen or halogen;R.sup.5 '=R.sup.5, H or (C.sub.1 -C.sub.6 -haloalkyl)carbonyl;R.sup.6= H, C.sub.1 -C.Type: GrantFiled: June 30, 1997Date of Patent: January 11, 2000Assignee: BASF AkteingesellschaftInventors: Ralf Klintz, Gerhard Hamprecht, Elisabeth Heistracher, Peter Schafer, Christoph-Sweder von dem Bussche-Hunnefeld, Peter Munster, Reinhard Kirstgen, Albrecht Harreus, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
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Patent number: 5981791Abstract: A new salt of a prodrug useful in antibody directed enzyme prodrug therapy (ADEPT) is disclosed. A hydrogen iodide salt of the prodrug N-(4-[N,N-bis(2-iodoethyl)amino]phenoxycarbonyl)-L-glutamic acid is prepared which can be obtained in crystalline form. Preparation of the crystalline form of the prodrug enables preparation of the prodrug in highly pure form.Type: GrantFiled: June 23, 1997Date of Patent: November 9, 1999Assignee: Zeneca LimitedInventors: David William Heaton, Susan Dines, Robert Ian Dowell
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Patent number: 5958971Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT). The prodrugs are substrates for carboxypeptidase G2 (CPG2) and yield more active cytotoxic drugs than known products of CPG2 catalyzed reactions.Type: GrantFiled: October 22, 1997Date of Patent: September 28, 1999Assignees: Zeneca Limited, Cancer Research Campaign Technology LimitedInventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger, Caroline Joy Springer
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Patent number: 5714148Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT). The prodrugs are substrates for carboxypeptidase G2 (CPG2) and yield more active cytotoxic drugs than known products of CPG2 catalysed reactions.Type: GrantFiled: September 30, 1996Date of Patent: February 3, 1998Assignees: Zeneca Limited, Cancer Research Campaign Technology LimitedInventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger, Caroline Joy Springer
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Patent number: 5660829Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT). The prodrugs are substrates for carboxypeptidase G2 (CPG2) and yield more active cytotoxic drugs than known products of CPG2 catalysed reactions.Type: GrantFiled: May 16, 1995Date of Patent: August 26, 1997Assignees: Zeneca Limited, Cancer Research Campaign TechnologyInventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger
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Patent number: 5602176Abstract: The (S)-N-ethyl-3-[(1-dimethylamino)ethyl]-N-methyl-phenylncarbamate in free base or acid addition salt form is useful as pharmaceutical, particularly for systemic transdermal administration.Type: GrantFiled: June 6, 1995Date of Patent: February 11, 1997Assignee: Sandoz Ltd.Inventor: Albert Enz
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Patent number: 5587161Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT).Type: GrantFiled: December 21, 1994Date of Patent: December 24, 1996Assignees: Zeneca Limited, Cancer Research Campaign Technology LimitedInventors: Philip J. Burke, Robert I. Dowell, Anthony B. Mauger, Caroline J. Springer
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Patent number: 5565490Abstract: p-Hydroxyaniline derivatives of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is hydrogen, or unsubstituted or substituted alkyl;R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl,OR.sup.5 or NR.sup.6 R.sup.7, whereR.sup.5, R.sup.6 are unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, andR.sup.7 is hydrogen or alkyl,and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests, and also compounds of the formula VI ##STR2## and their salts, processes for their preparation, compositions containing them and their use as intermediates and for controlling pests are described.Type: GrantFiled: November 10, 1994Date of Patent: October 15, 1996Assignee: BASF AktiengesellschaftInventors: Oliver Wagner, Karl Eicken, Norbert G otz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5466862Abstract: Low molecular weight polyaldehydes are prepared by converting the acetal groups of the low molecular weight polyacetal to aldehyde groups or by reacting an aldehyde-containing reagent (e.g., glyoxal) with a polyamide.Type: GrantFiled: September 22, 1994Date of Patent: November 14, 1995Assignee: National Starch and Chemical Investment Holding CorporationInventors: Gary T. Martino, Martin M. Tessler
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Patent number: 5446194Abstract: A compound according to formula 1 ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, carbamoyl which is substituted by an alkyl of 1 to 4 carbon atoms, alkylcarbonyl of 2 to 5 carbon atoms or phenyl carbonyl, X represents halogen nitro or cyano and R.sub.3 represents ##STR2## wherein R.sub.4 represents cyano or alkylcarbonyl of 2 to 5 carbon atoms and R.sub.5 represents carbamoyl which is unsubstituted or substituted with alkyl of 1 to 8 carbon atoms or which is substituted with hydroxyalkyl of 1 to 8 carbon atoms or pharmaceutically acceptable esters and salts thereof, and a pharmaceutically acceptable carrier therefor, as well as pharmaceutical compositions containing said compounds as COMT inhibitors.Type: GrantFiled: September 16, 1993Date of Patent: August 29, 1995Assignee: Orion-yhtyma OyInventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen
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Patent number: 5405990Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT). The prodrugs are substrates for carboxypeptidase G2 (CPG2) and yield more active cytotoxic drugs than known products of CPG2 catalyzed reactions.Type: GrantFiled: July 22, 1993Date of Patent: April 11, 1995Assignees: Zeneca Limited, Cancer Research Campaign Technology LimitedInventors: Philip J. Burke, Robert I. Dowell, Anthony B. Mauger, Caroline J. Springer
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Patent number: 5371271Abstract: Fungicidal substituted aminophenyl carbamates of the formula ##STR1## in which X represents --CO--NR.sup.8 R.sup.9 ; --CO--OR.sup.9 ; --CO--SR.sup.9 ; --CO--R.sup.10 ; --SO.sub.2 R.sup.9 or hydrogen, in whichR.sup.8 represents hydrogen or alkyl,R.sup.9 represents optionally substituted aryl, optionally substituted aralkyl, optionally substituted alkyl, alkenyl, halogenoalkenyl, or in each case optionally substituted cycloalkyl, cycloalkenyl or cycloalkylalkyl, and R.sup.10 has the meaning of R.sup.9 or represents an optionally substituted heterocyclic ring,Y.sup.1 to Y.sup.4 are identical or different and represent hydrogen, halogen, nitro, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, alkylsulfonyl or halogenolkylthio,R.sup.1 to R.sup.Type: GrantFiled: August 18, 1993Date of Patent: December 6, 1994Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Kruger, Klaus Sasse, Peter Heitkamper, Klaus Konig, Wilhelm Brandes, Gerd Hanssler, Albrecht Marhold
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Patent number: 5206418Abstract: The invention relates to aminotetrahydronaphthalene derivatives which are intermediates for the preparation of sulfonylaminotetrahydronaphthalenes.Type: GrantFiled: March 13, 1992Date of Patent: April 27, 1993Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Hideo Nakai, Toyoharu Yamashita, Harumichi Kohno, Yasuhiko Sasaki, Akio Odawara
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Patent number: 5206417Abstract: The ethylenically unsaturated organic compounds are of the general formula ##STR1## where R is alkyl, aryl or a radical R.sup.1, and R.sup.1 is a radical ##STR2## where R.sup.2 to R.sup.6 are each H, alkyl, OH, Oalkyl, SH, Salkyl, halogen, N(alkyl).sub.2 or N(alkyl)(aryl), and not less than one but not more than three of the radicals R.sup.2 to R.sup.6 are each a radical ##STR3## where X is alkylene or oxaalkylene, each of 2 to 10 carbon atoms, and Y is H or CH.sub.3. These compounds have particularly high photochemical reactivity in the medium-wavelength to relatively long-wavelength UV range.Type: GrantFiled: December 18, 1991Date of Patent: April 27, 1993Inventors: Andreas Boettcher, Gerd Rehmer
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Patent number: 5202483Abstract: Ethylenically unsaturated compounds of the general formula I ##STR1## where R.sub.1 is alkyl of 1 to 4 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, phenyl or phenyl in which some or all of the hydrogen atoms have been replaced by radicals R.sup.4, not more than two substituents R.sup.4 being identical, or R.sup.1 together with R.sup.2 or together with R.sup.6 forms a --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 -- bridge,R.sup.4 is alkyl of 1 to 24 carbon atoms, --OH, --O--R.sup.7, --S--R.sup.7, ##STR2## R.sup.2 or R.sup.6, independently of one another, both are hydrogen, or one of the radicals R.sup.4, or, where R.sup.1 is aryl,R.sup.2 or R.sup.6 is a direct bond to R.sup.1 in the ortho-position with respect to the carbonyl group, andR.sup.3 and R.sup.5 are each hydrogen, one of the radicals R.sup.4 or a group the general formula II ##STR3## where R.sup.7 and R.sup.8 are each alkyl of 1 to 4 carbon atoms,R.sup.9 is cycloalkyl of 5 or 6 carbon atoms,R.sup.Type: GrantFiled: March 1, 1991Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Kaspar Bott
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Patent number: 5189058Abstract: The compounds of the present invention have the formula ##STR1## wherein each of X and Y is oxygen or sulfur, R is hydrogen or lower alkyl, and each of R.sub.1 and R.sub.2 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, aralkyl, a hydrocarbon chain, a hetero group, or a heteroalkyl group, and the compounds are useful in treating atherosclerosis.Type: GrantFiled: April 9, 1991Date of Patent: February 23, 1993Assignee: Warner-Lambert CompanyInventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
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Patent number: 5176914Abstract: Fungicidal carbocyclic anilide carbamates of the formula ##STR1## in which X represents optionally alkyl-substituted cycloalkyl or optionally alkyl-substituted cycloalkenyl,Hal represents halogen, andY.sup.1, Y.sup.2 and Y.sup.3 independently of one another represent hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy or optionally halogen-substituted alkylthio, andR.sup.1 represents optionally halogen-substituted alkyl, alkenyl, alkylcarbonyloxyalkyl, alkenylcarbonyloxyalkyl and optionally substituted cycloalkyl which can be interrupted by hetero atoms, or represents optionally substituted phenyl or optionally substituted phenylalkyl, or R.sup.1 additionally can represent alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl if X represents optionally alkyl-substituted cycloalkenyl.Type: GrantFiled: August 15, 1990Date of Patent: January 5, 1993Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Kruger, Klaus Sasse, Wilhelm Brandes
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Patent number: 5066819Abstract: The invention relates to a process for the preparation of aryl esters of N-alkyl carbamic acids. The process comprises reacting an alkyl N-alkyl carbamate of the general formula:R.sub.1 --NH--COO--R.sub.3wherein R.sub.1 and R.sub.3 are both alkyl groups, with a substituted phenol in the presence of a halogen-containing phosphorous compound to produce an aryl ester of N-alkyl carbamic acid having the general formula:R.sub.1 --NH--COO--R.sub.2wherein R.sub.1 is an alkyl group and R.sub.2 is an aryl group derived from the substituted phenol. In a preferred embodiment of the invention, the process is used for the preparation of aryl esters of N-methyl carbamic acid.Type: GrantFiled: March 20, 1990Date of Patent: November 19, 1991Assignee: Council of Scientific & Industrial ResearchInventors: Gurunath H. Kulkarni, Rajan H. Naik, Srinivasachari Rajappa
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Patent number: RE39616Abstract: This invention is directed to compounds of the following formula: wherein when a is 0, b is 1 or 2; when a is 1, b is 1, m is from 0-3, X is O or S, Y is halogeno, R1 is hydrogen C1-4 alkyl, R2 is hydrogen, C1-4 alkyl, or optionally substituted propargyl and R3 and R4 are each independently hydrogen, C1-6 alkyl, C6-12 aryl, C6-12 aralkyl each optionally substituted. This invention is also directed to the use of these compounds for treating depression, Attention Deficit Disorder (ADD), Attention Deficit and Hyperactivity Disorder (ADHD), Tourette's Syndrome, Alzheimer's Disease and other dementia's such as senile dementia, dementia of the Parkinson's type, vascular dementia and Lewy body dementia. This invention is further directed to a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.Type: GrantFiled: March 25, 2005Date of Patent: May 8, 2007Assignees: Teva Pharmaceutical Industries, Ltd., Yissum Research Development Company of the Hebrew University of Jerusalem, Technion Research and Development Foundation, Ltd.Inventors: Michael Chorev, Tamar Goren, Yacov Herzig, Jeffrey Sterling, Marta Weinstock-Rosin, Moussa B. H. Youdim