Diazooxide Or Diazotate (e.g., -n=n-o-, Etc.) Patents (Class 534/556)
  • Publication number: 20140315865
    Abstract: Disclosed are hybrid compounds that release both nitric oxide and a moiety that inhibits poly (ADP-ribose) polymerase (PARP), e.g., a compound or a pharmaceutically acceptable salt thereof of formula (I), wherein R1-4 and m-p are as described herein. Also disclosed are pharmaceutical compositions and methods of use including treating cancer and enhancing the chemotherapeutic treatment of chemotherapeutic agents and high energy radiation.
    Type: Application
    Filed: October 18, 2012
    Publication date: October 23, 2014
    Inventors: Anna E. Maciag, Larry K. Keefer, Joseph E. Saavedra, Xinhua Ji, Vandana Kumari
  • Patent number: 8623846
    Abstract: A compound having the structure (I) or a pharmaceutically acceptable salt thereof, wherein R3 is hydrogen, deuterium, —OH, —OC1-6alkyl, or halogen; R8 is hydrogen, deuterium, or C1-6alkyl; R11 and R12 are independently hydrogen, —C1-6alkyl, —OH, —OC1-6alkyl, or halogen; R13 and R14 are independently —C1-6alkyl, —(CH2)1-2OH, or —OC1-6alkyl, or, together with the nitrogen atom to which they are attached, form a 4- to 7-membered heterocyclic ring containing one nitrogen atom and 0 or 1 oxygen atoms, wherein said ring is unsubstituted or mono-, di- or tri-substituted with halogen or —C1-6alkyl; R15 is —C(O)OH, —C(O)OCH2CH2N+CH3)3 wherein n is 0, 1 or 2, —C(O)NHCH(R17)OR16, or —C(O)NHCH(R17)C(O)NHCH(R18)C(O)OR16; R16 is hydrogen, C1-6alkyl, or (CH2)1-2N+R19R20R21; R1, R2, R4, R5, R6, R7, R9, R10, R17, R18, R19, R20, and R21 are independently hydrogen or —C1-6alkyl; and stereoisomers thereof, and pharmaceutically acceptable salts thereof, and pharmaceutically acceptable salts of stereoisomers thereof.
    Type: Grant
    Filed: May 16, 2011
    Date of Patent: January 7, 2014
    Assignee: Merck Sharp & Dohme Corp.
    Inventors: Amjad Ali, Lin Yan, Pei Huo, Ravi Nargund
  • Publication number: 20130296278
    Abstract: A compound having the structure (I) useful for treating hypertension, pulmonary arterial hypertension, congestive heart failure, conditions resulting from excessive water retention, cardiovascular disease, diabetes, oxidative stress, endothelial dysfunction, cirrhosis, pre-eclampsia, osteoporosis or nephropathy.
    Type: Application
    Filed: January 12, 2012
    Publication date: November 7, 2013
    Applicant: Merck Sharp & Dohme Corp.
    Inventors: Amjad Ali, Michael Man-Chu Lo, Edward Metzger, Shrenik K. Shah, James Dellureficio
  • Patent number: 8530133
    Abstract: Embodiments in accordance with the present invention provide for norbornane-type ballast materials, norbornane-type photoactive compounds derived from such ballast materials and alkali-soluble positive-tone polymer compositions that encompass such norbornane-type photoactive compounds and one of a PBO or PNB resin.
    Type: Grant
    Filed: September 28, 2011
    Date of Patent: September 10, 2013
    Assignee: Promerus, LLC
    Inventors: Andrew Bell, Keitaro Seto, Hiroaki Makabe, Edmund Elce
  • Patent number: 8377911
    Abstract: A compound having the structure formula (I) or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating hypertension.
    Type: Grant
    Filed: September 20, 2010
    Date of Patent: February 19, 2013
    Assignee: Merck Sharp & Dohme Corp.
    Inventors: Amjad Ali, Michael Man-Chu Lo, Lin Yan
  • Patent number: 8361994
    Abstract: A compound having the structure useful for treating hypertension, Pulmonary Arterial Hypertension (PAH), congestive heart failure, conditions resulting from excessive water retention, cardiovascular disease, diabetes, oxidative stress, endothelial dysfunction, cirrhosis, pre-eclampsia, osteoporosis or nephropathy.
    Type: Grant
    Filed: March 5, 2012
    Date of Patent: January 29, 2013
    Assignee: Merck Sharp & Dohme Corp
    Inventors: Amjad Ali, Michael Man-Chu Lo, Zhiqiang Guo, Brent Whitehead, Timothy J. Henderson, Lin Yan, Shrenik K. Shah
  • Patent number: 8354394
    Abstract: A compound having the structure (I) wherein R is selected from the group consisting of 1) and 2), or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating hypertension.
    Type: Grant
    Filed: October 22, 2010
    Date of Patent: January 15, 2013
    Assignee: Merck Sharp & Dohme Corp.
    Inventors: Amjad Ali, Christopher Franklin, Ravi Nargund, Michael Man-Chu Lo, Lin Yan, Pei Huo
  • Patent number: 8318402
    Abstract: Disclosed are a photosensitive compound and a method of manufacturing the same. The photosensitive is composed of a naphthoquinonediazide sulfonic ester compound having at least one naphthoquinonediazide sulfoxy group, and having either at least one carboxy group with 1 to 8 carbon atoms or at least one alkoxy group with 1 to 8 carbon atoms, in one molecule.
    Type: Grant
    Filed: December 30, 2009
    Date of Patent: November 27, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Joo Hyeon Park, Seok Chan Kang, Jung Hwan Cho, Kyung Chul Son
  • Patent number: 8263579
    Abstract: This invention relates to novel compounds obtained by fermentation of Myxobacteria strain (PM0670013/MTCC 5570). The present invention further relates to the processes for the production of the novel anti-inflammatory compounds, to the culture no. PM0670013 (MTCC 5570), and to pharmaceutical compositions containing compounds of the present invention as an active ingredient and its use in medicines for the treatment of inflammatory diseases or disorders mediated by proinflammatory cytokines such as Tumor Necrosis Factor-alpha (TNF-?) and/or interleukins such as IL-6, having anti-inflammatory activity The invention also includes all stereoisomeric forms of compounds of the present invention.
    Type: Grant
    Filed: January 24, 2011
    Date of Patent: September 11, 2012
    Assignee: Piramal Healthcare Limited
    Inventors: Koteppa Pari, Girish Badrinath Mahajan, Nidhi Tomar, Vijaya Phani Kumar Yemparala, Asha Adrian Kulkarni-Almeida, Saji George
  • Publication number: 20120190651
    Abstract: This invention relates to novel compounds obtained by fermentation of Myxobacteria strain (PM0670013/MTCC 5570). The present invention further relates to the processes for the production of the novel anti-inflammatory compounds, to the culture no. PM0670013 (MTCC 5570), and to pharmaceutical compositions containing compounds of the present invention as an active ingredient and its use in medicines for the treatment of inflammatory diseases or disorders mediated by proinflammatory cytokines such as Tumor Necrosis Factor-alpha (TNF-?) and/or interleukins such as IL-6, having anti-inflammatory activity The invention also includes all stereoisomeric forms of compounds of the present invention.
    Type: Application
    Filed: January 24, 2011
    Publication date: July 26, 2012
    Inventors: Koteppa Pari, Girish Badrinath Mahajan, Nidhi Tomar, Vijaya Phani Kumar Yemparala, Asha Adrian Kulkarni-Almeida, Saji George
  • Patent number: 8101589
    Abstract: This invention relates to compositions comprising carbon-based diazeniumdiolates that release nitric oxide (NO). The carbon-based diazeniumdiolated molecules release NO spontaneously under physiological conditions without subsequent nitrosamine formation. The present invention also relates to methods of preparing the carbon-based diazeniumdiolated molecules, compositions comprising such molecules, methods of using such compositions, and devices employing such molecule compositions.
    Type: Grant
    Filed: July 2, 2009
    Date of Patent: January 24, 2012
    Assignee: Noxilizer, Inc.
    Inventors: Ernst V. Arnold, Blaine G. Doletski, Robert E. Raulli
  • Patent number: 8012664
    Abstract: A compound of the formula (I) where the symbols and indices are each defined as follows: A is A?, R or O—R; where R is a straight-chain, branched or cyclic, saturated or unsaturated aliphatic radical having 1-8 carbon atoms; A? is the same or different and is B is a bond, —O—C(O)—, —C(O)—O—, —O—C(O)—, —C(O)—NH—, —NH—C(O)—, —C(O)—O—CH2—CH(OH)—CH2—O, —O—CH2—CH(OH)—CH2—O—(O)C—, —O—C(O)—O—, —O—C(O)—NH— or —NH—C(O)—O—; R1 is H or OH; m is 1, 2, 3, 4 or 5; Y is n is a positive rational number ?3; E is the same or different and is —CH—CHR2—, —CHR2—CH2—, —CH2—CHR2—O—, —O—CHR2—CH2—, —(CH2)r—O— or —O—(CH2)—; R2 is H or CH3 and r is 1 or 4, is suitable as a light-sensitive component for photoresists.
    Type: Grant
    Filed: November 6, 2006
    Date of Patent: September 6, 2011
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Wolfgang Zahn, Ralf Grottenmüller, Dieter Wagner
  • Patent number: 7829553
    Abstract: This invention relates to compositions comprising carbon-based diazeniumdiolates attached to hydrophobic polymers that releases nitric oxide (NO). The carbon-based diazeniumdiolated polymers release NO spontaneously under physiological conditions without subsequent nitrosamine formation. The present invention also relates to methods of preparing the carbon-based diazeniumdiolated polymers, compositions comprising such polymers, methods of using such compositions, and devices employing such polymer compositions.
    Type: Grant
    Filed: January 6, 2005
    Date of Patent: November 9, 2010
    Assignee: Amulet Pharmaceuticals, Inc.
    Inventors: Ernst V. Arnold, Blaine G. Doletski, Robert E. Raulli
  • Patent number: 7569559
    Abstract: This invention relates to compositions comprising carbon-based diazeniumdiolates that release nitric oxide (NO). The carbon-based diazeniumdiolated molecules release NO spontaneously under physiological conditions without subsequent nitrosamine formation. The present invention also relates to methods of preparing the carbon-based diazeniumdiolated molecules, compositions comprising such molecules, methods of using such compositions, and devices employing such molecule compositions.
    Type: Grant
    Filed: February 9, 2005
    Date of Patent: August 4, 2009
    Assignee: Noxilizer, Inc.
    Inventors: Ernst V. Arnold, Blaine G. Doletski, Robert E. Raulli
  • Patent number: 7511029
    Abstract: Pesticidal compounds having the structural formula wherein: R2 is C1-C6 branched or straight chain alkyl; C1-C4 branched or straight-chain haloalkyl; or C3-C6 cycloalkyl; m is 0, 1, or 2; X is selected from the group consisting of: C1-C6 branched or straight-chain alkoxy; halogen; C1-C6 branched or straight-chain alkyl; or C1-C6 branched or straight-chain alkylthio; n is 0 or 1; A is O; CH2; or NR?, wherein R? is (C1-C6 alkyl)carbonyl; Y is phenyl; benzyl; thiazolyl; thienyl; pyridyl; or tetrahydrofuranyl, the aromatic ring of each substituent being optionally substituted with one or more of halogen, C1-C6 branched or straight-chain alkyl, or C1-C6 branched or straight-chain haloalkyl; use of the compounds as pesticides and pesticidal compositions comprising the compounds.
    Type: Grant
    Filed: February 20, 2008
    Date of Patent: March 31, 2009
    Assignee: Chemtura Corporation
    Inventors: Mark A. Dekeyser, Paul T. McDonald
  • Publication number: 20080288176
    Abstract: The present invention provides a method of using a physiologically-based pharmacokinetic model to select a prodrug molecule (NO—X) comprising a therapeutic agent X (e.g. nonsteroidal anti-inflammatory drug, (NSAID)) and an appropriate nitric oxide donor NO. The NSAID can be a non-selective or selective cyclooxygenase inhibitor or other biocompatible compound comprising a carboxyl group. The pharmacokinetic model uses in vitro and/or in silico data to estimate an optimal set of parameters that can predict whether a particular NO—X candidate is capable of producing desirable therapeutic effects, e.g. enhanced anti-inflammatory activity, reduced intestinal, cardiac and renal toxicity. Accordingly, the present invention can greatly enhance proper selection of an appropriate candidate for drug development, thereby minimizing development time and conserving costs.
    Type: Application
    Filed: October 13, 2006
    Publication date: November 20, 2008
    Inventors: Yun Kau Tam, Christopher Mark Diaper, Hugh A. Semple, Douglas Thacher Ridgway, Yi-Chan James Lin, Brian Duff Sloley
  • Patent number: 7399841
    Abstract: A compound possesses the chemical structure of: wherein n is greater than zero. The compound is useful in energetic composition, particularly in linear, branched, dendritric, oligomer and cyclic oligomer azo-triazine forms.
    Type: Grant
    Filed: September 15, 2005
    Date of Patent: July 15, 2008
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Farhrad Forohar, Jesse Moran, David M. Rosenberg, Joseph D. Mannion, Brian W. Vos
  • Patent number: 7399757
    Abstract: Pesticidal compounds having the structural formula wherein R1 and R2 are each, independently, C1-6 alkyl, compositions comprising the compounds and methods for their use as pesticides.
    Type: Grant
    Filed: May 16, 2007
    Date of Patent: July 15, 2008
    Assignee: Chemtura Corporation
    Inventors: Mark A. Dekeyser, Paul T. McDonald
  • Patent number: 7355021
    Abstract: The present invention provides a single pot process for the preparation of diazonaphthoquinonesulfonyl ester, a useful organic material for micro electronic and dye industry. This study pertains to the one pot preparation of diazonaphthoquinonesulfonyl esters using the corresponding diazonaphthoquinine sulfonic acid or its sodium salt, diphosgene or triphosgene, variety of hydroxy compounds and tertiary organic base in an organic solvent medium.
    Type: Grant
    Filed: March 20, 2006
    Date of Patent: April 8, 2008
    Assignee: Council of Scientific & Industrial Research
    Inventors: Vummadi Venkat Reddy, Boddu Ananda Rao, Maruthi Janaki Ram Reddy, Chiguru Srinivas, Chilukuri Ramesh, Vaidya Jayathirtha Rao
  • Patent number: 7122529
    Abstract: Chemical compounds which release nitric oxide in a controlled manner upon photolysis with light are provided. These compounds are O2-benzyl, O2-naphthylmethyl and O2-naphthylallyl substituted diazeniumdiolates. Also provided are methods of preparing these novel compounds in high chemical yields as well as methods of using these compounds.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: October 17, 2006
    Assignee: The Johns Hopkins University
    Inventors: Patrick H. Ruane, John P. Toscano
  • Patent number: 7081524
    Abstract: The present invention provides O2-substituted 1-[(2-carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolates (1-[(2-carboxylato)pyrrolidin-1-yl]diazeniumdiolates) of the formula in which R and R22are as described herein. Also provided is a composition comprising such a compound and a carrier. The 1-[(2-carboxylato)pyrrolidin-1-yl]diazeniumdiolates compounds release nitric oxide under physiological conditions and are useful for treating biological disorders.
    Type: Grant
    Filed: April 12, 2005
    Date of Patent: July 25, 2006
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Joseph E Saavedra, Larry K Keefer
  • Patent number: 6911433
    Abstract: Provided are O2-glycosylated 1-substituted diazen-1-ium-1,2-diolates (O2-glycosylated diazeniumdiolates) having the formula: in which R is a saccharide, which is attached to the O2 of the compound by the anomeric carbon of a pyranose ring or a furanose ring.
    Type: Grant
    Filed: January 7, 2003
    Date of Patent: June 28, 2005
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Joseph E. Saavedra, Larry K. Keefer, Aloka Srinivasan, Christian Bogdan, William G. Rice, Xinhua Ji
  • Publication number: 20030220228
    Abstract: The present invention describes novel nitrosated and/or nitrosylated cyclooxygenase 2 (COX-2) inhibitors and novel compositions comprising at least one nitrosated and/or nitrosylated cyclooxygenase 2 (COX-2) inhibitor, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or optionally, at least one therapeutic agent, such as, steroids, nonsteroidal antiinflammatory compounds (NSAID), 5-lipoxygenase (5-LO) inhibitors, leukotriene B4 (LTB4) receptor antagonists, leukotriene A4 (LTA4) hydrolase inhibitors, 5-HT agonists, 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) inhibitors, H2antagonists, antineoplastic agents, antiplatelet agents, decongestants, diuretics, sedating or non-sedating anti-histamines, inducible nitric oxide synthase inhibitors, opioids, analgesics, Helicobacter pylori inhibitors, proton pump inhi
    Type: Application
    Filed: June 18, 2003
    Publication date: November 27, 2003
    Inventors: Ramani R. Bandarage, Upul K. Bandarage, Xinqin Fang, David S. Garvey, L. Gordon Letts, Joseph D. Schroeder, Sang William Tam
  • Publication number: 20030175613
    Abstract: The invention provides a 1,2-naphthoquinone-2-diazidesulfonate ester photosensitive agent which is useful as a photosensitive agent employed in a photoresist for producing semiconductor integrated circuits, liquid crystal displays, EL displays, etc., a method for producing the photosensitive agent, and a photoresist composition containing the photosensitive agent.
    Type: Application
    Filed: March 11, 2003
    Publication date: September 18, 2003
    Inventors: Hirotada Iida, Miharu Suwa, Yuichi Hagiwara, Katsumi Tada, Suehiro Katori, Tsuneaki Miyazaki
  • Publication number: 20030166619
    Abstract: The present invention relates to nitric oxide-releasing amidine- and enamine-derived diazeniumdiolates, compositions comprising such compounds, methods of using such compounds and compositions, and to a method for the preparation of nitric oxide-releasing amidine- and enamine-derived diazeniumdiolates via the direct reaction of nitric oxide with amidines and enamines, and to a method of converting amines into such compounds.
    Type: Application
    Filed: January 22, 2003
    Publication date: September 4, 2003
    Applicant: Government of the U.S.A., represented by the Secretary of Dept. of Health and Human Services
    Inventors: Joseph A. Hrabie, Larry K. Keefer
  • Patent number: 6610660
    Abstract: Diazeniumdiolates, wherein the N1 position is substituted by an inorganic or organic moiety and the O2-oxygen is bound to a substituted or unsubstituted aromatic group, are provided. Also provided are O2-glycosylated 1-substituted diazen-1-ium-1,2-diolates (O2-glycosylated diazeniumdiolates) and O2-substituted 1-[(2-carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolates (1-[(2-carboxylato)pyrrolidin-1-yl]diazeniumdiolates). The O2-aryl diazeniumdiolates are stable with respect to the hydrolytic generation of nitric oxide in neutral to acidic solutions and generate nitric oxide in basic or nucleophilic environments or microenvironments. Also provided are compositions, including pharmaceutical compositions, comprising such compounds and methods of using such compounds.
    Type: Grant
    Filed: May 3, 1999
    Date of Patent: August 26, 2003
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Joseph E. Saavedra, Larry K. Keefer, Aloka Srinivasan, William G. Rice, Xinhua Ji, Christian Bogdan
  • Publication number: 20030147845
    Abstract: Diazeniumdiolates, wherein the N1 position is substituted by an inorganic or organic moiety and the O2-oxygen is bound to a substituted or unsubstituted aromatic group, are provided. Also provided are O2-glycosylated 1-substituted diazen-1-ium-1,2-diolates (O2-glycosylated diazeniumdiolates) and O2-substituted 1-[(2-carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolates (1-[(2-carboxylato)pyrrolidin-1-yl]diazeniumdiolates). The O2-aryl diazeniumdiolates are stable with respect to the hydrolytic generation of nitric oxide in neutral to acidic solutions and generate nitric oxide in basic or nucleophilic environments or microenvironments. Also provided are compositions, including pharmaceutical compositions, comprising such compounds and methods of using such compounds.
    Type: Application
    Filed: January 7, 2003
    Publication date: August 7, 2003
    Applicant: Government of the USA, the Secretary Department of Health and Human Services
    Inventors: Joseph E. Saavedra, Larry K. Keefer, Aloka Srinivasan, Christian Bogdan, William G. Rice, Xinhua Ji
  • Patent number: 6566031
    Abstract: A positive photoresist composition includes (A) an alkali-soluble resin, (B) a photosensitizer including, for example, a quinonediazide ester of bis[2,5-dimethyl-3-(2-hydroxy-5-methylbenzyl)-4-hydroxyphenyl]methane, and (C) a compound having a gram absorption coefficient of 5 to 60 with respect to light with a wavelength of 365 nm.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: May 20, 2003
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takako Suzuki, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6077941
    Abstract: An effective method for producing a 1,2-naphthoquinone-2-diazide or a sulfo-substituted compound thereof from a 2-diazo-1-naphthalenesulfonic acid or a sulfo-substituted compound thereof. A 1,2-naphthoquinone-2-diazide derivative or a sulfo-substituted compound thereof is derived from a 2-diazo-1-naphthalenesulfonic acid or a sulfo-substituted compound thereof by use of an aqueous alkaline solution containing iodine; an aqueous alkaline solution containing iodine which is dissolved in an organic solvent; or an aqueous alkaline solution containing an oxidizing agent and iodine or an iodine compound.
    Type: Grant
    Filed: June 15, 1999
    Date of Patent: June 20, 2000
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Nobuhiro Yoneyama, Seiju Tobishima, Toshio Itahana, Kunihiko Kojima
  • Patent number: 5795878
    Abstract: A phenylazoxycyanide compound of formula I ##STR1## is useful as an antimicrobial and fungicidal composition. A method for using the antimicrobial and fungicidal compositions, and for manufacturing the compound is also disclosed.
    Type: Grant
    Filed: June 6, 1997
    Date of Patent: August 18, 1998
    Assignee: American Cyanamid Company
    Inventor: Werner Simon
  • Patent number: 5726295
    Abstract: A new class of 3,4-dihydrocoumarin derivatives which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include ether, ester, carbonate, and sulfonate derivatives of 5-hydroxy, 6-hydroxy, and 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarins. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: March 10, 1998
    Assignee: Hoechst Celanese Corp.
    Inventors: Mohammad Aslam, Michael T. Sheehan, Debasish Kuila
  • Patent number: 5726296
    Abstract: Novel processes for the preparation of a new class of coumarin derivatives, which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications, are disclosed and claimed. The process involves a multi-step synthetic method for the preparation of ether, ester, carbonate, or sulfonate derivative of 5-hydroxy, 6-hydroxy, or 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarin starting from the corresponding dihydroxyacetophenone. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: March 10, 1998
    Assignee: Hoechst Celanese Corp.
    Inventors: Mohammad Aslam, Michael T. Sheehan, Debasish Kuila
  • Patent number: 5683668
    Abstract: The present invention provides a method for the generation of NO gas by exposing zwitterionic polyamine-nitric oxide adducts of the formula RN?N(O)NO.sup.- !(CH.sub.2).sub.x NH.sub.2.sup.+ R', wherein R=C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 aminoalkyl, or cyclohexy, R'=hydrogen or C.sub.1 -C.sub.6 alkyl, and x=2-6, to suitable conditions to effect the release of NO, such as by contact with a mildly acidic solvent or water of neutral or slightly alkaline pH.
    Type: Grant
    Filed: February 2, 1996
    Date of Patent: November 4, 1997
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Joseph A. Hrabie, Larry K. Keefer
  • Patent number: 5644038
    Abstract: Quinone diazo compounds having bonded to the diazo ring or directly bonded to a ring of the compound, certain non-metallic atoms that improve the photosensitivity thereof are provided. These quinone diazo compounds are useful as photoactive compounds in photoresist compositions, and particularly positive photoresist composition employed in x-ray or electron beam radiation. Also provided is a method for preparing compounds of the present invention.
    Type: Grant
    Filed: March 15, 1996
    Date of Patent: July 1, 1997
    Assignee: International Business Machines Corporation
    Inventors: Ari Aviram, William Ross Brunsvold, Daniel Bucca, Willard Earl Conley, Jr., David Earle Seeger
  • Patent number: 5627175
    Abstract: The invention is directed to azoxycyanobenzene derivatives of the formula: ##STR1## wherein n is 0-3; each R represents halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, or haloalkoxy; and each R.sup.1 and R.sup.2 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, or aralkyl group. The compounds may be used as fungicides.
    Type: Grant
    Filed: July 24, 1995
    Date of Patent: May 6, 1997
    Assignee: ShellInternationale Research Maatschappij B.V.
    Inventor: Werner E. J. Simon
  • Patent number: 5475093
    Abstract: The invention relates to a process for the preparation of azoxycyanide compounds of the general formula ##STR1## in which R represents an optionally substituted aryl or heterocyclyl group, which comprises treating a compound of the general formulaR--N.dbd.O (II)in which R is as defined above, with cyanamide or a metal salt thereof and a compound of the general formula ##STR2## in which R.sup.1 represents an optionally substituted alkyl or aryl group and R.sup.2 represents a hydrogen atom or an optionally substituted alkyl or aryl group or R.sup.1 and R.sup.2 together represent a group ##STR3## where m is 2, 3, 4 or 5, k is 0 or 1 and each of R.sup.3 and R.sup.4 independently represents a hydrogen atom or an alkyl group, and X represents a chlorine, bromine or iodine atom or a cyano or --SO.sub.2 R.sup.5 group where R.sup.5 represents a hydrogen atom or an optionally substituted alkyl or aryl group. Compounds of general formula I exhibit biocidal activity.
    Type: Grant
    Filed: April 7, 1995
    Date of Patent: December 12, 1995
    Assignee: American Cyanamid Co.
    Inventor: Werner E. J. Simon
  • Patent number: 5439897
    Abstract: This invention relates to certain azoxycyanobenzene derivatives of the general formula. ##STR1## in which R represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl group; R.sup.1 represents a halogen atom, nitro, cyano or optionally substituted alkyl, alkoxy, aryl or aryloxy group; and R.sup.2 represents a hydrogen or halogen atom, nitro, cyano or optionally substituted alkyl or alkoxy group; process for their preparation, compositions containing such compounds and their use as fungicides.
    Type: Grant
    Filed: August 16, 1994
    Date of Patent: August 8, 1995
    Assignee: American Cyanamid Company
    Inventor: Werner E. J. Simon
  • Patent number: 5439774
    Abstract: A positive-type photosensitive electrodeposition coating composition comprising a water-soluble or water-dispersible resin having an ionic group and containing at least one modified quinonediazidesulfone unit represented by the following formula (I) or (II) ##STR1## wherein R.sub.1 represents ##STR2## R.sub.2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl ether group, andR.sub.3 represents an alkylene group, a cycloalkylene group, an alkylene ether group,a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, or an alkylene, cycloalkylene or alkylene ether group containing in its chain a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, in the molecule.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: August 8, 1995
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Naozumi Iwasawa, Junichi Higashi
  • Patent number: 5393874
    Abstract: The preparation of N-hydroxy-N'-diazenium oxides of the general formula I ##STR1## where R is an aliphatic or cycloaliphatic radical, by reacting a hydroxylamine of the general formula IIR--NH--OH IIor its salt with nitrosyl chloride or nitrosylsulfuric acid in aqueous solution is described.The process products are intermediates for fine chemicals and are used in the form of their metal salts as wood preservatives.
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: February 28, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Klemens Massonne, Martin Fischer
  • Patent number: 5374710
    Abstract: Chemical derivatives of nitric oxide are provided which are stable indefinitely in oxygen-containing solutions until photolysis, whereupon they release NO. These compounds have the general formulaA--N.sup.+ (O.sup.-)=N--O--B (I)wherein A is typically a nitrogen- or oxygen-containing substituent and B is a group lablie to photolysis. The compounds are stable and inert in oxygenated aqueous solutions, but release NO upon illumination. Given the ease with which the intensity, timing and location of illumination may be controlled, these compounds are particularly useful in investigating the biological effects of NO with much higher spatial or temporal resolution than heretofore possible.
    Type: Grant
    Filed: May 26, 1993
    Date of Patent: December 20, 1994
    Assignee: Regents of the University of California
    Inventors: Roger Y. Tsien, Lewis R. Makings
  • Patent number: 5358824
    Abstract: The photosensitive resin composition of the present invention comprises an admixture of 5 to 100 weight parts of a photosensitive material having the following general formula (A) and 100 weight parts of an alkali-soluble resin:General formula (A) ##STR1## where R.sub.1 to R.sub.8 each independently represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an aralkyl group, an aryl group, an amino group, a monoalkylamino group, a dialkylamino group, an acylamino group, an alkylcarbamoyl group, an arylcarbamoyl group, an alkylsulfamoyl group, an arylsulfamoyl group, a carboxyl group, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, or --OD, --N(R)--D (where R represents a hydrogen atom or an alkyl group, and D represents a 1,2-napthoquinoediazide-5-sulfonyl group or a 1,2-napthoquinoediazide-4-sulfonyl group), and at least one of R.sub.1 to R.sub.8 represents --OD or --N(R)--D; R.sub.9 to R.sub.
    Type: Grant
    Filed: September 10, 1993
    Date of Patent: October 25, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shiro Tan, Yasunori Takata, Yoshimasa Aotani, Fumiyuki Nishiyama
  • Patent number: 5312905
    Abstract: A 2-diazo-1,2-quinone compound having a substituent group containing an alkyl group which is substituted by at least one fluorine atom is described. This compound has a capacity to change its polarity when exposed to light. The invention also provides an image forming material in which the invention compound is added to at least one of laminated layers. When these laminated layers are exposed to light, the adhesiveness of the compound-containing layer to its adjoining layer is reduced effectively due to the polarity-changing ability of the compound, thus making the easy delamination of the layers possible. This compound is applicable to many instances in which image receiving sheets are used, such as the formation of a multi-color image by a transfer method (a color proof, for example) and the preparation of a printing plate of the delamination development type.
    Type: Grant
    Filed: July 26, 1991
    Date of Patent: May 17, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kan Wakamatsu, Yuichi Wakata, Masato Satomura, Tomizo Namiki
  • Patent number: 5298606
    Abstract: A process for the preparation of a compound of general formula ##STR1## wherein X represents a cyano group, a group --COOH or a salt, ester or amido derivative thereof, R.sup.1 represents a hydrogen atom or an optionally substituted alkyl group, R.sup.2 represents an optionally substituted alkyl or phenyl group, Z represents an alkyl group or a halogen atom and n represents 0, 1, 2, 3 or 4, the process comprising reacting a compound of general formula ##STR2## with a first reactant capable of both dehydrating the amide group of said compound of general formula IV, to form a group X wherein X represents a cyano group, and reacting with the carboxy group of said compound of general formula IV to form a group with which a compound of general formula R.sup.1 R.sup.2 NH may react; subsequently reacting the resulting compound with a compound of general formula R.sup.1 R.sup.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: March 29, 1994
    Assignee: Shell Research Limited
    Inventor: William W. Wood
  • Patent number: 5290658
    Abstract: A positive photoresist composition is provided, which comprises an alkali-soluble novolak resin and at least one light-sensitive material represented by formula (III), ##STR1## wherein R.sub.27 and R.sub.28 may be the same or different and which represents --OH, ##STR2## R.sub.29 and R.sub.33 may be the same or different and each represents --H, --OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted acyloxy group, a halogen, a nitro group, a cyano group, ##STR3## R.sub.34 to R.sub.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: March 1, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Yasumasa Kawabe, Tadayoshi Kokubo
  • Patent number: 5256517
    Abstract: A positive-working radiation-sensitive mixture is described which essentially contains a photoactive component and a water-insoluble binder which is soluble, or at least swellable, in aqueous alkaline solution, wherein a compound is used, as photoactive component, which contains .alpha.-diazo-.beta.-keto ester units and sulfonate units of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are an unsubstituted or substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical having 4 to 20 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by N or NH groups and/or contain keto groups,X is an unsubstituted or substituted aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by the groups --NR.sup.3 --, --C(O)--0--, --C(O)--NR.sup.3 --, ##STR2## --NR.sup.3 --C(O)--NR.sup.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: October 26, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Roeschert, Georg Pawlowski, Hans-Joachim Merrem, Ralph Dammel, Walter Spiess
  • Patent number: 5250669
    Abstract: Photosensitive compounds having preferably a functional group such as --SO.sub.2 Cl, --SO.sub.3 H, --SO.sub.3 R, ##STR1## (R, R', R" being alkyl) on a terminal benzene or naphthalene ring connected via a methylene group and ##STR2## moiety are improved in sensitivity to light and thermal stability, and thus useful in a photo resist.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: October 5, 1993
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Kazufumi Ogawa, Masayuki Endo, Keiji Ohno, Mamoru Nagoya
  • Patent number: 5238775
    Abstract: A radiation-sensitive resin composition containing an alkali-soluble resin, comprising a polyhydroxy compound having the following formula: ##STR1## or a quinonediazidesulfonate of the polyhydroxy compound. The radiation-sensitive resin composition is suitable for use as a positive type photoresist which has such excellent developability as to inhibit effectively the generation of scum in the formation of a photoresist pattern, has high sensitivity and is excellent in heat resistance and remained thickness ratio upon development.
    Type: Grant
    Filed: February 19, 1991
    Date of Patent: August 24, 1993
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Toru Kajita, Takao Miura, Yoshiji Yumoto, Chozo Okuda
  • Patent number: 5227473
    Abstract: A quinone diazide of formula (I) or formula (II):(S)l--(L.sup.1)m=-(Q).sub.n (I)--(L.sup.2 (-S))o-(L.sup.3 (--Q))p- (II)wherein S is a light absorbing portion having an absorption coefficient of greater than 1000 in wavelengths longer than 360 nm; Q is a quinone diazide residue; L.sup.1, L.sup.2 and L.sup.3 are connecting groups connecting S and Q, provided, however, that L.sup.1, L.sup.2 and L.sup.3 do not conjugate S and Q; l, m, n, o and p are integers; andwherein the emission intensity of the compound of formulas (I) and (II) is smaller than the emission intensity of the chromophoric group alone. Also disclosed is a light sensitive composition comprising an alkali soluble resin and the above quinone diazide compound. The quinone diazide compound of the present invention have spectral sensitization with respect to visible light and are useful in visible light projection plates and as visible laser sensing materials.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: July 13, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kouichi Kawamura, Satoshi Takita
  • Patent number: 5219714
    Abstract: A process of developing an image-wise exposed photoresist-coated substrate comprising: coating a substrate with a positive working photoresist comprising an admixture of an alkali soluble binder resin and photoactive formula (V): ##STR1## wherein R.sub.2 is selected from the group consisting of an OD group, a halide group, a lower alkyl group having 1 or 4 carbon atoms and a lower alkoxy group having 1 to 4 carbon atoms, and D is selected from the group consisting of o-naphthoquinone diazide sulfonyl group and hydrogen; with the proviso that at least four D's are o-naphthoquinone diazide sulfonyl groups; subjecting the coating on the substrate to an image-wise exposure of radiation; and subjecting the image-wise coated substrate to a developing solution to remove the exposed areas of the radiation-exposed coating, leaving a positive image pattern.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: June 15, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Medhat A. Toukhy, Alfred T. Jeffries, III
  • Patent number: RE40211
    Abstract: wherein R1 is a C3-8 branched or cyclic alkyl group, and R2 is a C1-8 straight-chain, branched or cyclic alkyl group, is effective as a photoacid generator when used in a photoresist material for light of 300 nm or less.
    Type: Grant
    Filed: March 15, 2001
    Date of Patent: April 1, 2008
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Fumiyoshi Urano, Masaaki Nakahata, Hirotoshi Fujie, Keiji Oono