Diazooxide Or Diazotate (e.g., -n=n-o-, Etc.) Patents (Class 534/556)
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Publication number: 20140315865Abstract: 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: ApplicationFiled: October 18, 2012Publication date: October 23, 2014Inventors: Anna E. Maciag, Larry K. Keefer, Joseph E. Saavedra, Xinhua Ji, Vandana Kumari
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Patent number: 8623846Abstract: 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: GrantFiled: May 16, 2011Date of Patent: January 7, 2014Assignee: Merck Sharp & Dohme Corp.Inventors: Amjad Ali, Lin Yan, Pei Huo, Ravi Nargund
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Publication number: 20130296278Abstract: 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: ApplicationFiled: January 12, 2012Publication date: November 7, 2013Applicant: Merck Sharp & Dohme Corp.Inventors: Amjad Ali, Michael Man-Chu Lo, Edward Metzger, Shrenik K. Shah, James Dellureficio
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Patent number: 8530133Abstract: 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: GrantFiled: September 28, 2011Date of Patent: September 10, 2013Assignee: Promerus, LLCInventors: Andrew Bell, Keitaro Seto, Hiroaki Makabe, Edmund Elce
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Patent number: 8377911Abstract: A compound having the structure formula (I) or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating hypertension.Type: GrantFiled: September 20, 2010Date of Patent: February 19, 2013Assignee: Merck Sharp & Dohme Corp.Inventors: Amjad Ali, Michael Man-Chu Lo, Lin Yan
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Patent number: 8361994Abstract: 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: GrantFiled: March 5, 2012Date of Patent: January 29, 2013Assignee: Merck Sharp & Dohme CorpInventors: Amjad Ali, Michael Man-Chu Lo, Zhiqiang Guo, Brent Whitehead, Timothy J. Henderson, Lin Yan, Shrenik K. Shah
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Patent number: 8354394Abstract: 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: GrantFiled: October 22, 2010Date of Patent: January 15, 2013Assignee: Merck Sharp & Dohme Corp.Inventors: Amjad Ali, Christopher Franklin, Ravi Nargund, Michael Man-Chu Lo, Lin Yan, Pei Huo
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Patent number: 8318402Abstract: 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: GrantFiled: December 30, 2009Date of Patent: November 27, 2012Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Joo Hyeon Park, Seok Chan Kang, Jung Hwan Cho, Kyung Chul Son
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Patent number: 8263579Abstract: 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: GrantFiled: January 24, 2011Date of Patent: September 11, 2012Assignee: Piramal Healthcare LimitedInventors: Koteppa Pari, Girish Badrinath Mahajan, Nidhi Tomar, Vijaya Phani Kumar Yemparala, Asha Adrian Kulkarni-Almeida, Saji George
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Publication number: 20120190651Abstract: 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: ApplicationFiled: January 24, 2011Publication date: July 26, 2012Inventors: Koteppa Pari, Girish Badrinath Mahajan, Nidhi Tomar, Vijaya Phani Kumar Yemparala, Asha Adrian Kulkarni-Almeida, Saji George
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Patent number: 8101589Abstract: 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: GrantFiled: July 2, 2009Date of Patent: January 24, 2012Assignee: Noxilizer, Inc.Inventors: Ernst V. Arnold, Blaine G. Doletski, Robert E. Raulli
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Patent number: 8012664Abstract: 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: GrantFiled: November 6, 2006Date of Patent: September 6, 2011Assignee: AZ Electronic Materials USA Corp.Inventors: Wolfgang Zahn, Ralf Grottenmüller, Dieter Wagner
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Patent number: 7829553Abstract: 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: GrantFiled: January 6, 2005Date of Patent: November 9, 2010Assignee: Amulet Pharmaceuticals, Inc.Inventors: Ernst V. Arnold, Blaine G. Doletski, Robert E. Raulli
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Patent number: 7569559Abstract: 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: GrantFiled: February 9, 2005Date of Patent: August 4, 2009Assignee: Noxilizer, Inc.Inventors: Ernst V. Arnold, Blaine G. Doletski, Robert E. Raulli
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Patent number: 7511029Abstract: 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: GrantFiled: February 20, 2008Date of Patent: March 31, 2009Assignee: Chemtura CorporationInventors: Mark A. Dekeyser, Paul T. McDonald
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Publication number: 20080288176Abstract: 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: ApplicationFiled: October 13, 2006Publication date: November 20, 2008Inventors: Yun Kau Tam, Christopher Mark Diaper, Hugh A. Semple, Douglas Thacher Ridgway, Yi-Chan James Lin, Brian Duff Sloley
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Patent number: 7399757Abstract: 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: GrantFiled: May 16, 2007Date of Patent: July 15, 2008Assignee: Chemtura CorporationInventors: Mark A. Dekeyser, Paul T. McDonald
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Patent number: 7399841Abstract: 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: GrantFiled: September 15, 2005Date of Patent: July 15, 2008Assignee: The United States of America as represented by the Secretary of the NavyInventors: William M. Koppes, Farhrad Forohar, Jesse Moran, David M. Rosenberg, Joseph D. Mannion, Brian W. Vos
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Patent number: 7355021Abstract: 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: GrantFiled: March 20, 2006Date of Patent: April 8, 2008Assignee: Council of Scientific & Industrial ResearchInventors: Vummadi Venkat Reddy, Boddu Ananda Rao, Maruthi Janaki Ram Reddy, Chiguru Srinivas, Chilukuri Ramesh, Vaidya Jayathirtha Rao
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Patent number: 7122529Abstract: 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: GrantFiled: July 12, 2002Date of Patent: October 17, 2006Assignee: The Johns Hopkins UniversityInventors: Patrick H. Ruane, John P. Toscano
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Patent number: 7081524Abstract: 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: GrantFiled: April 12, 2005Date of Patent: July 25, 2006Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Joseph E Saavedra, Larry K Keefer
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Patent number: 6911433Abstract: 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: GrantFiled: January 7, 2003Date of Patent: June 28, 2005Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Joseph E. Saavedra, Larry K. Keefer, Aloka Srinivasan, Christian Bogdan, William G. Rice, Xinhua Ji
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Publication number: 20030220228Abstract: 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 inhiType: ApplicationFiled: June 18, 2003Publication date: November 27, 2003Inventors: Ramani R. Bandarage, Upul K. Bandarage, Xinqin Fang, David S. Garvey, L. Gordon Letts, Joseph D. Schroeder, Sang William Tam
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Publication number: 20030175613Abstract: 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: ApplicationFiled: March 11, 2003Publication date: September 18, 2003Inventors: Hirotada Iida, Miharu Suwa, Yuichi Hagiwara, Katsumi Tada, Suehiro Katori, Tsuneaki Miyazaki
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Publication number: 20030166619Abstract: 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: ApplicationFiled: January 22, 2003Publication date: September 4, 2003Applicant: Government of the U.S.A., represented by the Secretary of Dept. of Health and Human ServicesInventors: Joseph A. Hrabie, Larry K. Keefer
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Patent number: 6610660Abstract: 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: GrantFiled: May 3, 1999Date of Patent: August 26, 2003Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Joseph E. Saavedra, Larry K. Keefer, Aloka Srinivasan, William G. Rice, Xinhua Ji, Christian Bogdan
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Publication number: 20030147845Abstract: 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: ApplicationFiled: January 7, 2003Publication date: August 7, 2003Applicant: Government of the USA, the Secretary Department of Health and Human ServicesInventors: Joseph E. Saavedra, Larry K. Keefer, Aloka Srinivasan, Christian Bogdan, William G. Rice, Xinhua Ji
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Patent number: 6566031Abstract: 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: GrantFiled: September 26, 2000Date of Patent: May 20, 2003Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takako Suzuki, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6077941Abstract: 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: GrantFiled: June 15, 1999Date of Patent: June 20, 2000Assignee: Toyo Gosei Kogyo Co., Ltd.Inventors: Hirotada Iida, Nobuhiro Yoneyama, Seiju Tobishima, Toshio Itahana, Kunihiko Kojima
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Patent number: 5795878Abstract: 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: GrantFiled: June 6, 1997Date of Patent: August 18, 1998Assignee: American Cyanamid CompanyInventor: Werner Simon
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Patent number: 5726295Abstract: 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: GrantFiled: March 7, 1997Date of Patent: March 10, 1998Assignee: Hoechst Celanese Corp.Inventors: Mohammad Aslam, Michael T. Sheehan, Debasish Kuila
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Patent number: 5726296Abstract: 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: GrantFiled: March 7, 1997Date of Patent: March 10, 1998Assignee: Hoechst Celanese Corp.Inventors: Mohammad Aslam, Michael T. Sheehan, Debasish Kuila
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Patent number: 5683668Abstract: 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: GrantFiled: February 2, 1996Date of Patent: November 4, 1997Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Joseph A. Hrabie, Larry K. Keefer
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Patent number: 5644038Abstract: 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: GrantFiled: March 15, 1996Date of Patent: July 1, 1997Assignee: International Business Machines CorporationInventors: Ari Aviram, William Ross Brunsvold, Daniel Bucca, Willard Earl Conley, Jr., David Earle Seeger
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Patent number: 5627175Abstract: 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: GrantFiled: July 24, 1995Date of Patent: May 6, 1997Assignee: ShellInternationale Research Maatschappij B.V.Inventor: Werner E. J. Simon
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Patent number: 5475093Abstract: 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: GrantFiled: April 7, 1995Date of Patent: December 12, 1995Assignee: American Cyanamid Co.Inventor: Werner E. J. Simon
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Patent number: 5439897Abstract: 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: GrantFiled: August 16, 1994Date of Patent: August 8, 1995Assignee: American Cyanamid CompanyInventor: Werner E. J. Simon
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Patent number: 5439774Abstract: 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: GrantFiled: September 28, 1994Date of Patent: August 8, 1995Assignee: Kansai Paint Co., Ltd.Inventors: Naozumi Iwasawa, Junichi Higashi
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Patent number: 5393874Abstract: 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: GrantFiled: September 14, 1993Date of Patent: February 28, 1995Assignee: BASF AktiengesellschaftInventors: Klemens Massonne, Martin Fischer
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Patent number: 5374710Abstract: 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: GrantFiled: May 26, 1993Date of Patent: December 20, 1994Assignee: Regents of the University of CaliforniaInventors: Roger Y. Tsien, Lewis R. Makings
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Patent number: 5358824Abstract: 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: GrantFiled: September 10, 1993Date of Patent: October 25, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Shiro Tan, Yasunori Takata, Yoshimasa Aotani, Fumiyuki Nishiyama
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Patent number: 5312905Abstract: 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: GrantFiled: July 26, 1991Date of Patent: May 17, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Kan Wakamatsu, Yuichi Wakata, Masato Satomura, Tomizo Namiki
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Patent number: 5298606Abstract: 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: GrantFiled: May 28, 1992Date of Patent: March 29, 1994Assignee: Shell Research LimitedInventor: William W. Wood
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Patent number: 5290658Abstract: 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: GrantFiled: April 24, 1992Date of Patent: March 1, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuya Uenishi, Yasumasa Kawabe, Tadayoshi Kokubo
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Patent number: 5256517Abstract: 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: GrantFiled: May 1, 1991Date of Patent: October 26, 1993Assignee: Hoechst AktiengesellschaftInventors: Horst Roeschert, Georg Pawlowski, Hans-Joachim Merrem, Ralph Dammel, Walter Spiess
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Patent number: 5250669Abstract: 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: GrantFiled: April 23, 1992Date of Patent: October 5, 1993Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Kazufumi Ogawa, Masayuki Endo, Keiji Ohno, Mamoru Nagoya
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Patent number: 5238775Abstract: 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: GrantFiled: February 19, 1991Date of Patent: August 24, 1993Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Toru Kajita, Takao Miura, Yoshiji Yumoto, Chozo Okuda
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Patent number: 5227473Abstract: 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: GrantFiled: May 10, 1991Date of Patent: July 13, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Kouichi Kawamura, Satoshi Takita
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Patent number: 5219714Abstract: 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: GrantFiled: September 14, 1992Date of Patent: June 15, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Medhat A. Toukhy, Alfred T. Jeffries, III
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Patent number: RE40211Abstract: 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: GrantFiled: March 15, 2001Date of Patent: April 1, 2008Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Fumiyoshi Urano, Masaaki Nakahata, Hirotoshi Fujie, Keiji Oono