2,2,1-bicyclo Patents (Class 560/120)
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Patent number: 6531627Abstract: An ester compound of the following formula (1) is provided. R1 is H, methyl or CH2CO2R3, R2 is H, methyl or CO2R3, R3 is C1-C15 alkyl, R4 is branched or cyclic, tertiary C5-C20 alkyl group, Z is a divalent C1-C10 hydrocarbon group, and k is 0 or 1. A resist composition comprising as the base resin a polymer resulting from the ester compound is sensitive to high-energy radiation, has excellent sensitivity, resolution, and etching resistance, and is suited for micropatterning using electron beams or deep-UV.Type: GrantFiled: April 26, 2001Date of Patent: March 11, 2003Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeru Watanabe, Takeshi Kinsho, Mutsuo Nakashima, Seiichiro Tachibana, Jun Hatakeyama
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Patent number: 6524765Abstract: A polymer comprising units of formula (1-1) or (1-2) and having a weight average molecular weight of 1,000 to 500,000 is provided. R1 is an acid labile group, R2 is H or straight or branched C1-4 alkyl, Z is a tetravalent C2-10 hydrocarbon group, and k=0 or 1. A resist composition comprising the polymer as a base resin has significantly improved sensitivity, resolution and etching resistance and is very useful in microfabrication.Type: GrantFiled: November 14, 2000Date of Patent: February 25, 2003Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Takeru Watanabe, Jun Hatakeyama, Takeshi Kinsho, Koji Hasegawa, Seiichiro Tachibana
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Patent number: 6521781Abstract: A 2-hydrocarbyl-2-adamantyl acrylate compound represented by the following Formula 6: is produced easily and stably with high yields by reacting a 2-adamantanone compound represented by the following Formula 1: with at least one organometallic compound represented by the following Formula 2 or 3: R1MgX (2) R1Li (3) and at least one acrylic compound represented by the following Formula 4 or 5: wherein, R1, R2, R3, X, Y and n in the above formulae being as defined in the disclosure.Type: GrantFiled: December 6, 2001Date of Patent: February 18, 2003Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Minoru Kakuda, Yoshihisa Arai, Kikuo Furukawa, Takehiko Isobe
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Patent number: 6469197Abstract: It is an object of the present invention to provide a negative photoresist composition for lithography, using short-wavelength light such as ArF excimer laser beam as a light source. The negative photoresist composition of the present invention is a negative photoresist composition comprising at least a polymer having a unit represented by the general formula (1) a crosslinking agent and a photo-acid generating agent, and the crosslinking agent is capable of crosslinking the polymer in the presence of an acid catalyst, whereby the polymer is insolubilized in a developer. Since the negative resist composition of the present invention is insolubilized in the developer by an action of an acid produced from the photo-acid generating agent at the exposed portion, a negative pattern can be obtained.Type: GrantFiled: September 25, 2000Date of Patent: October 22, 2002Assignee: NEC CorporationInventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
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Patent number: 6465551Abstract: Compounds and compositions comprising specific metal salts of bicyclo[2.2.1 ]heptane dicarboxylate salts in order to provide highly desirable properties within polyolefin articles are provided. The inventive salts and derivatives thereof are useful as nucleating and/or clarifying agents for such polyolefin, provide excellent crystallization temperatures, stiffness, and calcium stearate compatibility within target polyolefin. Also, such compounds exhibit very low hygroscopicity and therefore excellent shelf stability as powdered or granular formulations. Polyolefin additive compositions and methods of producing polyolefin with such compounds are also contemplated within this invention.Type: GrantFiled: March 24, 2001Date of Patent: October 15, 2002Assignee: Milliken & CompanyInventors: Xiaodong Edward Zhao, Darin L. Dotson
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Patent number: 6433215Abstract: A novel tricyclodecanyl (meth)acrylate compound and a method of producing the same are provided. The compound is 8-alkyl-8-tricyclodecanyl (meth)acrylate represented by formula (1): wherein R1 is methyl or ethyl and R2 is hydrogen or methyl.Type: GrantFiled: March 1, 2000Date of Patent: August 13, 2002Assignee: Chem Search Corp.Inventor: Hyun-jin Jung
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Patent number: 6426171Abstract: The present invention provides novel bicyclic photoresist monomers, and photoresist copolymer derived from the same. The bicyclic photoresist monomers of the present invention are represented by the formula: where m, n, R, V and B are those defined herein. The photoresist composition comprising the photoresist copolymer of the present invention has excellent etching resistance and heat resistance, and remarkably enhanced PED stability (post exposure delay stability).Type: GrantFiled: July 28, 2000Date of Patent: July 30, 2002Assignee: Hyundai Electronics Industries Co., Ltd.Inventors: Min Ho Jung, Jae Chang Jung, Geun Su Lee, Ki Ho Baik
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Patent number: 6410748Abstract: A monomer represented by the following general formula (m-1): wherein R is a group having an alicyclic skeleton, R2s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group, X1 is a bivalent organic group containing a heteroatom, j is an integer of 0 to 3, and R1 is a group selected from the following groups, a monovalent organic group having Si (R1-1), and —(X2)k—R4—(X3)m—C(R6)3 (R1-2), wherein X2 and X3 are a bivalent organic group containing a heteroatom, k and m are an integer of 0 to 3, R4 is a bivalent alkyl group, R6s may be the same or different and are individually hydrogen atom, halogen atom or monovalent organic group.Type: GrantFiled: May 3, 2001Date of Patent: June 25, 2002Assignee: Kabushiki Kaisha ToshibaInventors: Naomi Shida, Toru Ushirogouchi, Koji Asakawa, Takeshi Okino, Shuji Hayase, Yoshihiko Nakano, Makoto Nakase
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Patent number: 6376700Abstract: An alicyclic compound of the formula (1) is disclosed: wherein R1 and R2 each independently is a hydroxyl group, a C1-8 hydroxyalkyl group, or a C3-8 hydroxycycloalkyl group; R3, R4 and R5 each independently is a hydrogen, a C1-8 hydroxyalkyl group, a C1-6 carboxylic acid or a C3-8 carboxylic acid ester; k is an integer of 0, 1, 2, 3, 4, 5 or 6. The compound of the formula (1) can be applied to dissolution inhibitors for preparing positive photoresist composition.Type: GrantFiled: June 30, 2000Date of Patent: April 23, 2002Assignee: Everlight USA, Inc.Inventors: Shang-Wern Chang, Yen-Cheng Li, Shang-Ho Lin, Wen-Chieh Wang
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Patent number: 6368770Abstract: The present invention provides a novel photoresist monomer, photoresist copolymer derived from the same, and the photoresist composition comprising the same. In particular, the present invention provides a photoresist monomer of the formula: wherein, A, A′, X, m and n are those defined herein. The photoresist composition of the present invention has an excellent etching and heat resistance, and enhances the resolution and profile of the photoresist film.Type: GrantFiled: July 21, 2000Date of Patent: April 9, 2002Assignee: Hyundai Electronics Industries Co. Ltd.Inventors: Min Ho Jung, Jae Chang Jung, Geun Su Lee, Ki Ho Baik
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Patent number: 6369194Abstract: The invention relates to compounds of formula where R is a structural diversity element selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, peptidyl, heteroatom-substituted alkyl, cycloalkyl, and amines; and Nu is a structural diversity element derived from a nucleophile, NuH, selected from the group consisting of amines, amino acids, peptide, water, hydrogen sulfide, alcohols, and thiols. The invention also relates to arrays and combinatorial libraries of such compounds, and to a method of preparing such compounds.Type: GrantFiled: November 9, 1998Date of Patent: April 9, 2002Assignee: Yale UniversityInventor: Harry H. Wasserman
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Patent number: 6358675Abstract: The polymers of the invention are characterized by having at least one pendent ester group having a tertiary carbon atom attached to the ester oxygen atom in which at least one substituent of the tertiary carbon atom comprises at least one silicon atom. The polymer compositions of the present invention are useful as resist materials for lithography, in particular as the imaging layer or as the top imaging layer in a bilayer resist scheme for use in the manufacture of integrated circuits. The silicon-containing tertiary alcohols and esters of the present invention enable the preparation of polymers with relatively high silicon content.Type: GrantFiled: September 30, 1999Date of Patent: March 19, 2002Assignee: 3M Innovative Properties CompanyInventors: Larry D. Boardman, Carl R. Kessel
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Patent number: 6348296Abstract: The present invention relates to a copolymer resin for a photoresist used with ultra-short wavelength light source such as KrF or ArF, a process for preparation thereof, and a photoresist comprising said resin. By introducing 2,3-di-t-butyl-5-norbornene-2,3-dicarboxylate unit into the structure of a norbornene-maleic anhydride copolymer, the copolymer resin according to the present invention is easily prepared by conventional radical polymerization, has high transparency at 193 nm wavelength, provides increased etching resistance, prevents the top loss phenomenon, exhibits enhanced adhesive strength due to increasing protection ratio in the copolymer resin, and shows excellent resolution.Type: GrantFiled: December 30, 1998Date of Patent: February 19, 2002Assignee: Hyundai Electronics Industries Co., Ltd.Inventors: Min Ho Jung, Cha Won Koh, Hyung Gi Kim
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Publication number: 20020019560Abstract: The present invention is directed to photoresist cross-linkers selected from the group consisting of a cross-linker monomer represented by following Chemical Formula 1, and homopolymers and copolymers thereof. Such cross-linkers are suitable for use in photolithography processes employing KrF(248nm), ArF(193nm), E-beam, ion-beam or EUV light sources.Type: ApplicationFiled: September 11, 2001Publication date: February 14, 2002Inventors: Keun Kyu Kong, Jae Chang Jung, Myoung Soo Kim, Hyoung Gi Kim, Hyeong Soo Kim, Ki Ho Baik
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Publication number: 20020007031Abstract: An ester compound of the following formula (1) is provided.Type: ApplicationFiled: April 26, 2001Publication date: January 17, 2002Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeru Watanabe, Takeshi Kinsho, Mutsuo Nakashima, Seiichiro Tachibana, Jun Hatakeyama
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Publication number: 20010051742Abstract: Ester compounds of formula (1) are useful as monomers to form base resins for use in chemically amplified resist compositions adapted for micropatterning lithography.Type: ApplicationFiled: April 26, 2001Publication date: December 13, 2001Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Koji Hasegawa, Takeru Watanabe, Takeshi Kinsho, Mutsuo Nakashima, Seiichiro Tachibana, Tsunehiro Nishi, Jun Hatakeyama
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Publication number: 20010051741Abstract: Ester compounds of formula (1) are useful as monomers to form base resins for use in chemically amplified resist compositions adapted for micropatterning lithography.Type: ApplicationFiled: April 26, 2001Publication date: December 13, 2001Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Koji Hasegawa, Takeshi Kinsho, Mutsuo Nakashima, Seiichiro Tachibana, Tsunehiro Nishi, Jun Hatakeyama
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Patent number: 6313327Abstract: This invention relates to novel carboxylic acid derivatives represented by the following formula I and their synthesis: wherein, R1 is an hydrogen atom, an alkyl group or an alkoxy group of 1 to 20 carbon atoms in a linear, branched or cyclic form; R2 is a carboxy group of 1 to 40 carbon atoms in a linear, branched or cyclic form which is unsubstituted, or substituted into a hydroxy group, an ester group and an ether group. The novel carboxylic acid derivatives are more easily decomposed by acid than t-butyl ester compounds but are not dissolved in basic aqueous solution. According to this invention, carboxylic acid is under condensation with halogen compounds designed to prepare a larger monomolecular compound compared to the conventional method. Further, the condensed site is easily decomposed by acid but is extremely insoluble by basic aqueous solution.Type: GrantFiled: October 25, 1999Date of Patent: November 6, 2001Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Dong Seoul Seo, Joo Hyeon Park, Jae Young Kim, Seong Ju Kim
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Publication number: 20010031420Abstract: The present invention provides photoresist monomers, photoresist polymers derived from the same, processes for producing such photoresist polymers, photoresist compositions comprising such polymers, and processes for producing a photoresist pattern using such photoresist compositions.Type: ApplicationFiled: February 15, 2001Publication date: October 18, 2001Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
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Patent number: 6284429Abstract: A novel ester compound having an exo-form 2-alkylbicyclo[2.2.1]heptan-2-yl group as the protective group is provided as well as a polymer comprising units of the ester compound. The polymer is used as a base resin to formulate a resist composition having a higher sensitivity, resolution and etching resistance than conventional resist compositions.Type: GrantFiled: February 24, 2000Date of Patent: September 4, 2001Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeshi Kinsho, Tsunehiro Nishi, Hideshi Kurihara, Mutsuo Nakashima, Koji Hasegawa, Takeru Watanabe
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Patent number: 6222061Abstract: A novel norbornene carboxylate compound and a method of producing the same are provided. The norbornene carboxylate compound is 2-alkyl-2-adamantyl 5-norbornene-2-carboxylate represented by formula (1): wherein R is methyl or ethyl.Type: GrantFiled: March 1, 2000Date of Patent: April 24, 2001Assignee: Chem Search Corp.Inventor: Hyun-jin Jung
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Patent number: 6200731Abstract: The present invention discloses a cross-linking monomer for a photoresist polymer represented by following Chemical Formula 1: <Chemical Formula 1> wherein, V represents CH2, CH2CH2, oxygen or sulfur; Y is selected from the group consisting of straight or branched C1-10 alkyl, oxygen, and straight or branched C1-10 ether; R′ and R″ individually represent H or CH3; i is a number of 1 to 5; and n is a number of 0 to 3; and a process for preparing a photoresist copolymer comprising the same.Type: GrantFiled: December 16, 1999Date of Patent: March 13, 2001Assignee: Hyundai Electronics Industries Co., Ltd.Inventors: Geun Su Lee, Cha Won Koh, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
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Patent number: 6187393Abstract: Compounds of formula (I) are provided which are particularly useful in super twisted nematic devices, where n may be 0-5; m may be 0-5; p may be 1-9; q may be 1, 1, or 2; A1, A2 are independently chosen from 1-4, -disubstituted benzene, 2,5-disubstituted pyrimidine, or 2,5-disubstituted pyridine, trans- 1,4-disubstituted cyclohexane, trans- 2,5-disubstitued dioxane. The aromatic rings may be laterally substituted with F, Cl, Br or CN; Z1 may be O, COO, OOC; Z2, Z3 are independent chosen from a direct bond, COO, OOC, C2H4, CH2O, OCH2, or -c≡c-, provided that when Z1 is O and m is 1, 3 or 5 the carbon—carbon double bond configuration is E; provided that when Z1 is O and m is 2 or 4 the carbon—carbon double bond configuration is Z; provided that when Z1 is COO or OOC and m is 0, 2 or 4 the carbon—carbon double bond configuration is E; and provided that when Z1 is COO or OOC and m is 1, 3 or 5 the carbon—carbon double bond configuration is Z.Type: GrantFiled: March 19, 1999Date of Patent: February 13, 2001Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Warren L. Duffy, Stephen M Kelly, John W Goodby
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Patent number: 6180818Abstract: A silver halide photographic material is disclosed, comprising a support having thereon at least one light-sensitive silver halide emulsion layer, wherein said silver halide photographic material contains a compound by formula (IA), or which contains at least one hydroxamic acid compound having a bicyclo ring as a partial structure and represented by formula (IB).Type: GrantFiled: November 3, 1999Date of Patent: January 30, 2001Assignee: Fuji Photo Film Co., Ltd.Inventors: Hisashi Mikoshiba, Hiroo Takizawa, Junichiro Hosokawa, Yoshio Ishii, Keiji Mihayashi, Masakazu Morigaki, Mamoru Sakurazawa
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Patent number: 6153785Abstract: A novel norbornene carboxylate compound and a method of producing the same are provided. The norbornene carboxylate compound is 8-alkyl-8-tricyclodecanyl 5-norbornene-2-carboxylate represented by formula (1): ##STR1## wherein R is methyl or ethyl.Type: GrantFiled: March 1, 2000Date of Patent: November 28, 2000Assignee: Chem Search Corp.Inventor: Hyun-jin Jung
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Patent number: 6147249Abstract: A novel ester compound having an alkylcycloalkyl or alkylcycloalkenyl group as the protective group is provided as well as a polymer comprising units of the ester compound. The polymer is used as a base resin to formulate a resist composition having a higher sensitivity, resolution and etching resistance than conventional resist compositions.Type: GrantFiled: May 10, 1999Date of Patent: November 14, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Takeshi Kinsho, Tsunehiro Nishi, Mutsuo Nakashima, Koji Hasegawa, Jun Hatakeyama
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Patent number: 6114570Abstract: A silver halide photographic material is disclosed, comprising a support having thereon at least one light-sensitive silver halide emulsion layer, wherein said silver halide photographic material contains a compound by formula (IA), or which contains at least one hydroxamic acid compound having a bicyclo ring as a partial structure and represented by formula (IB).Type: GrantFiled: September 2, 1998Date of Patent: September 5, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Hisashi Mikoshiba, Hiroo Takizawa, Junichiro Hosokawa, Yoshio Ishii, Keiji Mihayashi, Masakazu Morigaki, Mamoru Sakurazawa
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Patent number: 6083501Abstract: A drug for prevention and therapy of diseases caused by fibrinoid formation or thrombus formation, as well as a model animal of fibrinoid formation or thrombus formation in the lung is disclosed. The drug for preventing and treating diseases caused by fibrinoid formation or thrombus formation in the lung according to the present invention comprises an inhibitor of interleukin 6 as an effective ingredient. The model animal of the diseases caused by fibrinoid formation or thrombus formation in the lung is a rat in which fibrinoid formation or thrombus formation actually occurs by induction with interleukin 6.Type: GrantFiled: March 14, 1996Date of Patent: July 4, 2000Assignee: Toray Industries, Inc.Inventors: Masayuki Miyata, Reiji Kasukawa, Masanobu Naruto, Nobutaka Ida, Yu-ichiro Sato, Katsuaki Kojima, Nobuo Ida
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Patent number: 6057460Abstract: Polymerizable hybrid monomers with norbornenyl or norbornadienyl groups are described which can be radically cured at room temperature and are suitable in particular for use in the dental field.Type: GrantFiled: February 21, 1997Date of Patent: May 2, 2000Assignee: Ivoclar AGInventors: Norbert Moszner, Volker Rheinberger, Frank Zeuner
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Patent number: 6020370Abstract: Bridged cyclic amino acids of formula ##STR1## are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain and neuropathological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.Type: GrantFiled: May 19, 1998Date of Patent: February 1, 2000Assignee: Warner-Lambert CompanyInventors: David Christopher Horwell, Justin S. Bryans, Clare O. Kneen, Andrew I. Morrell, Giles S. Ratcliffe
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Patent number: 5783724Abstract: Described are allyl esters of 2-norbornane acrylic acids and 2-norbornylidene propionic acids defined according to the generic structure: ##STR1## wherein the wavy line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein one of the dashed lines is carbon-carbon single bond and the other of the dashed lines is a carbon-carbon double bond; and wherein R represents methyl or hydrogen; as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles.Type: GrantFiled: March 6, 1997Date of Patent: July 21, 1998Assignee: International Flavors & Fragrances Inc.Inventors: Wilhelmus Johannes Wiegers, Marie R. Hanna
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Patent number: 5741925Abstract: Vinyl naphthenate monomer mixtures are prepared by transvinylation of naphthenic acid in the presence of a catalyst of a palladium carboxylate complexed with one or more aryl N-containing ligands and distilling the resulting vinyl naphthenate monomers in the presence of the catalyst at pot temperatures exceeding 80.degree. C. The catalyst is stable and can be re-used over several transvinylation reaction runs.Type: GrantFiled: January 13, 1997Date of Patent: April 21, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Chung-Ling Mao, Francis Joseph Waller, Kenneth Merle Kem
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Patent number: 5698514Abstract: Described are allyl esters of 2-norbornane acrylic acids and 2-norbornylidene propionic acids defined according to the generic structure: ##STR1## wherein the wavy line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein one of the dashed lines is carbon-carbon single bond and the other of the dashed lines is a carbon-carbon double bond; and wherein R represents methyl or hydrogen; as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles.Type: GrantFiled: May 25, 1995Date of Patent: December 16, 1997Assignee: International Flavors & Fragrances Inc.Inventors: Wilhelmus Johannes Wiegers, Marie R. Hanna
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Patent number: 5659070Abstract: A process for preparing alkyl 5-oxo-6-heptenoates of the formula I ##STR1## where X and Y are hydrogen or methyl, and R.sup.1 is C.sub.1 -C.sub.8 -alkyl, byA) reacting 5-acetyl-2-norbornene with a dialkyl carbonate [CO(OR.sup.2).sub.2, where R.sup.2 is C.sub.1 -C.sub.4 -alkyl,] in the presence of a base to give an alkyl 3-(2-norbornen-5-yl)-3-oxopropionate II,B) reacting the ester II on the presence of a base with an unsaturated compound of the formula III ##STR2## where Z is CN or CO.sub.2 R.sup.3, where R.sup.3 is C.sub.1 -C.sub.4 -alkyl, and hydrolyzing the product of the reaction of compound II with compound III to a 5-(2-norbornen-5-yl)-5-oxopentanoic acid of the formula IV,C) esterifying the acid IV to give a 5-(2-norbornen-5-yl)-5-oxopentanoic ester of the formula V, andD) converting the ester V by thermal cleavage into an alkyl 5-oxo-6-heptenoate I.Type: GrantFiled: February 1, 1996Date of Patent: August 19, 1997Assignee: BASF AktiengesellschaftInventors: Klaus Ebel, Matthias Eiermann, Thomas Papkalla
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Patent number: 5616780Abstract: The novel compounds of the formula I ##STR1## in which A is a group of the formula IIa or IIb, ##STR2## Y is oxygen, methylene, ethylidene or a >C.dbd.C(CH.sub.3).sub.2 group, Z is nitrogen, ##STR3## R.sub.1 and R.sub.2 are, for example C.sub.1 -C.sub.5 alkyl, R.sub.3 and R.sub.4 are, for example, hydrogen or methyl, and R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13 and R.sub.14 are, for example, hydrogen, are suitable for stabilizing organic material against oxidative, thermal or light-induced degradation.Type: GrantFiled: January 31, 1996Date of Patent: April 1, 1997Assignee: Ciba-Geigy CorporationInventors: Rita Pitteloud, Bernard Gilg
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Patent number: 5591854Abstract: A process of enantioselective synthesis of seven-membered carbocycles in the presence of di-rhodium(II) tetracarboxylate catalysts.Type: GrantFiled: October 14, 1994Date of Patent: January 7, 1997Assignee: Wake Forest UniversityInventor: Huw M. L. Davies
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Patent number: 5532386Abstract: A process for preparing compounds of the formula I ##STR1## where: Y inter alia is ##STR2## where R.sup.3 is hydrogen or a C.sub.1 -C.sub.10 - hydrocarbon radical. R.sup.1 and R.sup.2, inter alia, are each, independently of one another, hydrogen, a C.sub.1 -C.sub.20 -hydrocarbon radical which optionally carries inert substituents or heteroaryl, wherein a compound of the formula II ##STR3## where Z is ##STR4## is reacted in the presence of catalytic amounts of a carbonic ester and of a nitrogenous base at from 100.degree. to 250.degree. C. under a pressure of from 0.01 to 100 bar.Type: GrantFiled: March 1, 1995Date of Patent: July 2, 1996Assignee: BASF AktiengesellschaftInventor: Rolf Fischer
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Patent number: 5434267Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.Type: GrantFiled: March 14, 1994Date of Patent: July 18, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
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Patent number: 5391571Abstract: The compounds of the formula: ##STR1## in which R.sup.1 is alkyl of 4 or more carbon atoms, cycloalkyl, 1-adamantyl, 2-adamantyl, 3-noradamantyl, 3-methyl-1-adamantyl, 1-fluorenyl, 9-fluorenyl, cycloalkylalkyl, phenyl, substituted phenyl, alkyl, alkoxy, halo, nitro, cyano or trifluoromethyl, phenylalkyl or substituted phenylalkyl, where the substituent on the benzene ring is alkyl, alkoxy, halo, nitro, cyano, trifluoromethyl or phenyl; R.sup.2 is hydrogen, alkyl or R.sup.1 taken with R.sup.2 and the nitrogen atom to which they are attached form a heterocyclic moiety of the formula: ##STR2## wherein ##STR3## in which R.sup.7 is hydrogen, alkyl, hydroxy, alkanoyloxy, hydroxyalkyl, hydroxycarbonyl, alkoxycarbonyl, phenyl or substituted phenyl, in which the substituent is alkyl, alkoxy, halo, nitro, cyano, haloalkyl, perhaloalkyl or dialkylaminoalkyl; R.sup.8 is hydrogen or alkyl or R.sup.7 and R.sup.8 taken together are polymethylene; R.sup.Type: GrantFiled: May 13, 1993Date of Patent: February 21, 1995Assignee: American Home Products CorporationInventors: Richard E. Mewshaw, Thomas J. Commons, Donald P. Strike
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Patent number: 5268489Abstract: Unsaturated cycloaliphatic esters like higher hydrocarbyl, functionally substituted or polyunsaturated cyclohex-3-ene carboxylates, made directly by cycloaddition of dienes with dienophillic (meth/eth)acrylates, and their derivatives like epoxides and urethanes, provide useful thermal and radiation curable coatings, inks, sealants, adhesives, solvents, acid scavengers, and intermediates for other uses.Type: GrantFiled: February 5, 1993Date of Patent: December 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
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Patent number: 5266728Abstract: The present invention provides a method for producing optically active 3-substituted-2-norbornanones which are useful as starting materials for several kinds of physiologically active materials, and to their intermediates, optically active 2-hydroxy-2-norbornanecarboxylic acid and to a method for producing these intermediates.Type: GrantFiled: August 19, 1992Date of Patent: November 30, 1993Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Teruyo Sugiura, Kazutoshi Miyazawa, Yasuyuki Koizumi
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Patent number: 5248748Abstract: Disclosed is a diacetylene compound comprising, as structural units, (a) at least one member selected from diacetylene group-containing organic groups of the formulae (I) and (II):R.sup.I --C.tbd.C--C.tbd.C--R.sup.II -- (I)and--R.sup.III --C.tbd.C--C.tbd.C--R.sup.IV -- (II)wherein R.sup.I is hydrogen or a (C1-16) monovalent organic group, and R.sup.II, R.sup.III and R.sup.IV are a (C1-13) divalent organic group,(b) at least one organic group having at least one carbon-to-carbon double bond, and (c) at least one connecting group connecting the units (a) and (b) , which connecting group is selected from amide, imide, ester, ether, amino, imino, urethane, sulfonyl and carbonyl bonds. A cured shaped article made of this compound exhibits isotropically a high elastic modulus and has excellent mechanical properties.Type: GrantFiled: December 19, 1990Date of Patent: September 28, 1993Assignee: Dir. General of Agency of Industrial Science and TechnologyInventors: Katsuyuki Nakamura, Satoru Yamazaki, Jinichiro Kato, Kensaku Tokushige
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Patent number: 5241104Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.Type: GrantFiled: June 23, 1992Date of Patent: August 31, 1993Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura
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Patent number: 5175341Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.Type: GrantFiled: June 20, 1991Date of Patent: December 29, 1992Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura
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Patent number: 5077309Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.Type: GrantFiled: March 28, 1990Date of Patent: December 31, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5047575Abstract: Compounds, and a process for their preparation, have the formula ##STR1## or corresponding salts thereof wherein R represents a group of the formula ##STR2## wherein R.sub.1 represents oxazolinyl, --C.tbd.N, --CH.sub.2 OR.sub.2 or ##STR3## These compounds in the form of pharmaceutical or cosmetic compositions are useful for the treatment of keratinization disorders.Type: GrantFiled: October 14, 1988Date of Patent: September 10, 1991Assignee: L'OrealInventors: Guy Solladie, Serge Forestier, Gerard Lang
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Patent number: 5047574Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.Type: GrantFiled: December 12, 1989Date of Patent: September 10, 1991Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura
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Patent number: 5043451Abstract: There are provided compounds of the formula: ##STR1## wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.5 alkyl; R.sub.2 is an C.sub.1 -C.sub.10 alkyl, aryl, aralkyl, or pyridyl, where the aryl, aralkyl, or pyridyl are unsubstituted or are substituted by C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro, hydroxy, carboxy, amino, C.sub.1 -C.sub.5 alkylamino, C.sub.1 -C.sub.5 dialkylamino whose two alkyl groups may be different from each other, C.sub.2 -C.sub.3 alkanoylamino, or halogen and X is an C.sub.1 -C.sub.7 alkylene, C.sub.2 -C.sub.7 alkenylene, --CH(F)CH.dbd.CH(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 --S--(CH.sub.2).sub.2 --, --CH.sub.2).sub.2 --S--(CH.sub.2).sub.3 --, --C.sub.6 H.sub.4 --O--CH.sub.2 --or --CH.sub.2 CH.dbd.CH--m--C.sub.6 H.sub.4 --, or their pharmaceutically acceptable salts. The compounds are useful as antithrombotic, anti-vasoconstricting and anti-bronchoconstricting drugs.Type: GrantFiled: April 27, 1990Date of Patent: August 27, 1991Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Fumihiko Watanabe, Tadadiko Tsushima, Kenji Kawada, Susumu Kamata
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Patent number: 4957940Abstract: Certain bicyclo [2.2.1] heptane and bicyclo [2.2.2] octane substituted tetrahydro-2H-pyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.Type: GrantFiled: November 21, 1989Date of Patent: September 18, 1990Assignee: Warner-Lambert CompanyInventor: Bruce D. Roth
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Patent number: 4898977Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst