Nitrogen In Phenolic Moiety Patents (Class 560/136)
  • Patent number: 10882819
    Abstract: 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: Grant
    Filed: September 25, 2019
    Date of Patent: January 5, 2021
    Assignee: Cadila Corporate Campus
    Inventors: Jhillu Singh Yadav, Gyanchander Eppa, Pranav Rameshbhai Vachharajani, Nutan Bharatbhai Vekariya, Chetan Umeshbhai Bhavsar, Rajiv Indravadan Modi, Bakulesh Mafatlal Khamar
  • Patent number: 8637713
    Abstract: 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: Grant
    Filed: December 5, 2012
    Date of Patent: January 28, 2014
    Assignee: Novartis AG
    Inventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
  • Patent number: 8420846
    Abstract: 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: Grant
    Filed: August 25, 2009
    Date of Patent: April 16, 2013
    Assignee: Jubilant Life Sciences Limited
    Inventors: Shailendra Kumar Dubey, Vikas Bansal, Kamaljeet Pannu, Sushil Kumar Dubey
  • Patent number: 8415508
    Abstract: 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: Grant
    Filed: December 17, 2009
    Date of Patent: April 9, 2013
    Assignee: Novartis AG
    Inventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
  • Patent number: 8324429
    Abstract: 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: Grant
    Filed: January 10, 2008
    Date of Patent: December 4, 2012
    Assignees: 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
  • Patent number: 8283453
    Abstract: 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: Grant
    Filed: August 14, 2009
    Date of Patent: October 9, 2012
    Assignee: International Business Machines Corporation
    Inventors: Ali Afzali-Ardakani, Phaedon Avouris, James B. Hannon, Christian Klinke
  • Patent number: 8049031
    Abstract: 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: Grant
    Filed: December 10, 2009
    Date of Patent: November 1, 2011
    Assignee: Chemi S.p.A.
    Inventors: Umberto Ciambecchini, Maurizio Zenoni, Stefano Turchetta
  • Patent number: 8013181
    Abstract: 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: Grant
    Filed: April 10, 2008
    Date of Patent: September 6, 2011
    Assignees: 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
  • Publication number: 20100286437
    Abstract: 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: Application
    Filed: January 10, 2008
    Publication date: November 11, 2010
    Inventors: Fuli Zhang, Meng Hu, Meihua Xie, Anping Lai, Rentong Sun, Daoxin Chen, Rusheng Bao, Hua Bai
  • Publication number: 20100190725
    Abstract: 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: Application
    Filed: July 4, 2008
    Publication date: July 29, 2010
    Applicant: PROXIMAGEN LTD.
    Inventor: Christopher Hobbs
  • Patent number: 7683205
    Abstract: 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: Grant
    Filed: October 31, 2006
    Date of Patent: March 23, 2010
    Assignee: Alembic Limited
    Inventors: Pandurang Balwant Deshpande, Kishore Khemani, Bharat Becharbhai Boda, Tushar Rajnikant Shah, Hitarth Harshendu Acharya, Parven Kumar Luthra
  • Patent number: 7649114
    Abstract: 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: Grant
    Filed: May 29, 2006
    Date of Patent: January 19, 2010
    Assignee: Gruenenthal GmbH
    Inventors: Helmut Heinrich Buschmann, Wolfgang Hell
  • Patent number: 7531684
    Abstract: 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: Grant
    Filed: September 28, 2007
    Date of Patent: May 12, 2009
    Assignee: Synthon BV
    Inventors: Henar Tejedor Vinent, Arjanne Overeem, Lambertus Thijs
  • Publication number: 20080306280
    Abstract: 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 are
    Type: Application
    Filed: June 11, 2007
    Publication date: December 11, 2008
    Inventors: Mohammed Abdul Raheem, Zhi-Xian Wang, Eckardt C.G. Wolf
  • Patent number: 7405239
    Abstract: 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: Grant
    Filed: September 16, 2004
    Date of Patent: July 29, 2008
    Assignee: Merck Patent GmbH
    Inventors: Rolf Gericke, Norbert Beier, Oliver Poeschke, Lars Burgdorf, Helga Drosdat, Florian Lang
  • Patent number: 7385076
    Abstract: 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-isomer
    Type: Grant
    Filed: June 2, 2003
    Date of Patent: June 10, 2008
    Assignee: Sun Pharmaceutical Industries Limited
    Inventors: Hetalkumar Virendrabhai Patel, Rajamannar Thennati
  • Patent number: 6927303
    Abstract: 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: Grant
    Filed: June 19, 2003
    Date of Patent: August 9, 2005
    Assignee: 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
  • Patent number: 6835748
    Abstract: 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: Grant
    Filed: January 23, 2003
    Date of Patent: December 28, 2004
    Assignee: Novartis AG
    Inventor: David Goldblum
  • Publication number: 20040102652
    Abstract: 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: Application
    Filed: June 9, 2003
    Publication date: May 27, 2004
    Inventors: Gabriele Amari, Maurizio Del Canale, Roberta Razzetti, Pier Alessandro Monici Preti, Ivano Rondelli
  • Patent number: 6730700
    Abstract: 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: Grant
    Filed: July 15, 2002
    Date of Patent: May 4, 2004
    Assignee: Renovis, Inc.
    Inventors: L. David Waterbury, Allan L. Wilcox, John M. Carney, Farah Mavandadi, Albert Danielzadeh
  • Publication number: 20040067981
    Abstract: A compound of the formula (I): 1
    Type: Application
    Filed: July 28, 2003
    Publication date: April 8, 2004
    Applicant: SANKYO COMPANY, LIMITED
    Inventors: Kazuo Koyama, Shinji Marumoto, Narihiro Toda, Hiroshi Kogen, Keiko Suzuki
  • Publication number: 20040010038
    Abstract: The subject invention provides derivatives of propargylamino indan (PAI) and propargylamino tetralin that selectively inhibit monoamine oxidase (MAO) in the brain, having the structure: 1
    Type: Application
    Filed: February 27, 2003
    Publication date: January 15, 2004
    Inventors: Eran Blaugrund, Yaacov Herzig, Jeffrey Sterling
  • Patent number: 6573297
    Abstract: 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: Grant
    Filed: October 29, 2001
    Date of Patent: June 3, 2003
    Assignee: Shiseido Co., Ltd.
    Inventors: Koji Kobayashi, Hirotada Fukunishi, Tokuro Iwabuchi
  • Patent number: 6534541
    Abstract: 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: Grant
    Filed: October 11, 2000
    Date of Patent: March 18, 2003
    Assignee: Novartis AG
    Inventor: David Goldblum
  • Patent number: 6512136
    Abstract: 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: Grant
    Filed: December 17, 1999
    Date of Patent: January 28, 2003
    Assignee: Portela & C.A., S.A.
    Inventors: Jan Benes, Patricio Manuel Viera Araujo Soares Da Silva, David Alexander Learmonth
  • Publication number: 20020188020
    Abstract: This invention is directed to compounds of the following formula: 1
    Type: Application
    Filed: August 31, 2001
    Publication date: December 12, 2002
    Applicant: Yissum Research Development Company of the Hebrew University of Jerusalem
    Inventors: Michael Chorev, Tamar Goren, Yacov Herzig, Jeffrey Sterling, Marta Weinstock-Rosin, Moussa B.H. Youdim
  • Patent number: 6342523
    Abstract: 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: Grant
    Filed: December 1, 1999
    Date of Patent: January 29, 2002
    Assignee: Centaur Pharmaceuticals, Inc.
    Inventors: L. David Waterbury, Allan L. Wilcox, John M. Carney, Farah Mavandadi, Albert Danielzadeh
  • Patent number: 6303650
    Abstract: 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: Grant
    Filed: June 18, 1999
    Date of Patent: October 16, 2001
    Assignees: 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
  • Patent number: 6251938
    Abstract: 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: Grant
    Filed: June 18, 1999
    Date of Patent: June 26, 2001
    Assignees: Teva Pharmaceutical Industries, Ltd.,, Technion Research and Development Foundation, Ltd.,, Yissum Research Development Company of the Hebrew University of Jerusalem
    Inventors: Michael Chorev, Tamar Goren, Yacov Herzig, Jeffrey Sterling, Marta Weinstock-Rosin, Moussa B. H. Youdim
  • Patent number: 6153646
    Abstract: A family of platinum complexes which are stable and exhibit anticancer activity.
    Type: Grant
    Filed: December 9, 1998
    Date of Patent: November 28, 2000
    Assignee: Yoshinori Kidani
    Inventors: Yoshinori Kidani, Rolland-Yves Mauvernay, Teruko Irie
  • Patent number: 6022989
    Abstract: A process is disclosed for the preparation of an N-acylated activated derivative of an amino acid or a salt thereof.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: February 8, 2000
    Assignee: Abbott Laboratories
    Inventors: Patricia A. Oliver, Arthur J. Cooper, Joseph B. Paterson, Jr., Denton C. Langridge, Jieh-Heh J. Tien
  • Patent number: 6013606
    Abstract: 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: Grant
    Filed: June 30, 1997
    Date of Patent: January 11, 2000
    Assignee: BASF Akteingesellschaft
    Inventors: 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
  • Patent number: 5981791
    Abstract: 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: Grant
    Filed: June 23, 1997
    Date of Patent: November 9, 1999
    Assignee: Zeneca Limited
    Inventors: David William Heaton, Susan Dines, Robert Ian Dowell
  • Patent number: 5958971
    Abstract: 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: Grant
    Filed: October 22, 1997
    Date of Patent: September 28, 1999
    Assignees: Zeneca Limited, Cancer Research Campaign Technology Limited
    Inventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger, Caroline Joy Springer
  • Patent number: 5714148
    Abstract: 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: Grant
    Filed: September 30, 1996
    Date of Patent: February 3, 1998
    Assignees: Zeneca Limited, Cancer Research Campaign Technology Limited
    Inventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger, Caroline Joy Springer
  • Patent number: 5660829
    Abstract: 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: Grant
    Filed: May 16, 1995
    Date of Patent: August 26, 1997
    Assignees: Zeneca Limited, Cancer Research Campaign Technology
    Inventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger
  • Patent number: 5602176
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: February 11, 1997
    Assignee: Sandoz Ltd.
    Inventor: Albert Enz
  • Patent number: 5587161
    Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT).
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: December 24, 1996
    Assignees: Zeneca Limited, Cancer Research Campaign Technology Limited
    Inventors: Philip J. Burke, Robert I. Dowell, Anthony B. Mauger, Caroline J. Springer
  • Patent number: 5565490
    Abstract: 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: Grant
    Filed: November 10, 1994
    Date of Patent: October 15, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Oliver Wagner, Karl Eicken, Norbert G otz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5466862
    Abstract: 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: Grant
    Filed: September 22, 1994
    Date of Patent: November 14, 1995
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Gary T. Martino, Martin M. Tessler
  • Patent number: 5446194
    Abstract: 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: Grant
    Filed: September 16, 1993
    Date of Patent: August 29, 1995
    Assignee: Orion-yhtyma Oy
    Inventors: 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
  • Patent number: 5405990
    Abstract: 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: Grant
    Filed: July 22, 1993
    Date of Patent: April 11, 1995
    Assignees: Zeneca Limited, Cancer Research Campaign Technology Limited
    Inventors: Philip J. Burke, Robert I. Dowell, Anthony B. Mauger, Caroline J. Springer
  • Patent number: 5371271
    Abstract: 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: Grant
    Filed: August 18, 1993
    Date of Patent: December 6, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Klaus Sasse, Peter Heitkamper, Klaus Konig, Wilhelm Brandes, Gerd Hanssler, Albrecht Marhold
  • Patent number: 5206418
    Abstract: The invention relates to aminotetrahydronaphthalene derivatives which are intermediates for the preparation of sulfonylaminotetrahydronaphthalenes.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: April 27, 1993
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Hideo Nakai, Toyoharu Yamashita, Harumichi Kohno, Yasuhiko Sasaki, Akio Odawara
  • Patent number: 5206417
    Abstract: 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: Grant
    Filed: December 18, 1991
    Date of Patent: April 27, 1993
    Inventors: Andreas Boettcher, Gerd Rehmer
  • Patent number: 5202483
    Abstract: 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: Grant
    Filed: March 1, 1991
    Date of Patent: April 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Rehmer, Kaspar Bott
  • Patent number: 5189058
    Abstract: 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: Grant
    Filed: April 9, 1991
    Date of Patent: February 23, 1993
    Assignee: Warner-Lambert Company
    Inventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
  • Patent number: 5176914
    Abstract: 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: Grant
    Filed: August 15, 1990
    Date of Patent: January 5, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Klaus Sasse, Wilhelm Brandes
  • Patent number: 5066819
    Abstract: 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: Grant
    Filed: March 20, 1990
    Date of Patent: November 19, 1991
    Assignee: Council of Scientific & Industrial Research
    Inventors: Gurunath H. Kulkarni, Rajan H. Naik, Srinivasachari Rajappa
  • Patent number: RE39616
    Abstract: 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: Grant
    Filed: March 25, 2005
    Date of Patent: May 8, 2007
    Assignees: 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