The Three-membered Hetero Ring Is Unsubstituted Or Alkyl Substituted Only Patents (Class 548/969)
  • Patent number: 8558010
    Abstract: A process for aziridination of olefins using NaIO4/alkali metal bromide/H+/Chloramine-T combination in presence of dipolar aprotic solvent under ambient conditions to obtain aziridines is disclosed.
    Type: Grant
    Filed: October 7, 2011
    Date of Patent: October 15, 2013
    Assignee: Council of Scientific & Industrial Research
    Inventors: Pratibha Uttam Karbal, Pandurang Vilasrao Chouthaiwale, Gurunath Mallappa Suryavanshi, Arumugam Sudalai, Tanveer Mahamadali Shaikh
  • Patent number: 8507612
    Abstract: A crosslinkable, pre-adhesive composition is described comprising an acid-functional (meth)acrylate copolymer and an aziridine crosslinking agent, which when crosslinked provides a pressure-sensitive adhesive and pressure-sensitive adhesive articles.
    Type: Grant
    Filed: February 22, 2010
    Date of Patent: August 13, 2013
    Assignee: 3M Innovative Properties Company
    Inventors: Peiwang Zhu, Zhong Chen, Babu N. Gaddam, Larry R. Krepski, Jingjing Ma, David B. Olson, Andrew Satrijo, Dong-Wei Zhu
  • Patent number: 7838110
    Abstract: A photoactive compound that is the Michael addition reaction product of an aziridine compound and a photoinitiator-functional (meth)acrylate is described. The compound can be used to crosslink (meth)acrylic polymers via a hydrogen abstracting or an alpha-cleavage mechanism.
    Type: Grant
    Filed: December 2, 2008
    Date of Patent: November 23, 2010
    Assignee: 3M Innovative Properties Company
    Inventors: Peiwang Zhu, Maureen A. Kavanagh, Kelly S. Anderson, Larry R. Krepski, Guy D. Joly, Belma Erdogan, Babu N. Gaddam
  • Publication number: 20100191000
    Abstract: Process for preparing an N-unsubstituted or N-substituted aziridine of the formula which comprises reacting an olefin of the formula I where R1 to R5 are each, independently of one another, hydrogen, a linear or branched alkyl radical having from 1 to 16 carbon atoms, a hydroxyalkyl radical having from 1 to 4 carbon atoms, a cycloalkyl radical having from 5 to 7 carbon atoms, a benzyl or phenyl radical which in each case may be substituted in the o, m or p position of the phenyl radical by methoxy, hydroxy, chlorine or alkyl radicals having from 1 to 4 carbon atoms and the radical R1 or R2 together with the radical R3 or R4 may be closed to form a 5- to 12-membered ring or the radicals R1 and R2 may be closed to form a 5- to 12-membered ring, with ammonia or a primary amine of the formula R5NH2 in the presence of iodine or bromine.
    Type: Application
    Filed: June 18, 2008
    Publication date: July 29, 2010
    Applicant: BASF SE
    Inventors: Johann-Peter Melder, Martin Ernst, Till Gerlach, Ekkehard Schwab, Csaba Varszegi, Bert Sels, Dirk de Vos
  • Patent number: 7268228
    Abstract: This invention relates to compounds of Formula I having an aziridine-2-carboxylic group and a menthol group, a process for preparing such compounds, a method for obtaining optically active aziridine-2-carboxylate derivatives by optical resolution of such compounds, and optically active aziridine-2-carboxylate derivatives obtained by the same method: wherein R1 is hydrogen; alkyl; cycloalkyl; 4-chlorophenyl; 4-methoxyphenyl; s-triazinyl or pyridinyl acyl; benzyl; hydrocarbon residue which may be substituted with a substituent selected from the group consisting of hydroxy, alkoxy, dialkylamino, phenyl, 4-chlorophenyl and 4-methoxyphenyl; 2,4-dimethoxyphenyl; substituted phenyl including (1R)-phenylethyl or (1S)-phenylethyl. Preferences are given to (1R)-phenylethyl and (1S)-phenylethyl. Menthol is selected from the group consisting of (+)-menthol and (?)-menthol.
    Type: Grant
    Filed: August 10, 2001
    Date of Patent: September 11, 2007
    Assignee: Imagene Co., Ltd.
    Inventors: Won Koo Lee, Chan Sun Park, Yeon Hwa Lim, Hyun J on Ha
  • Patent number: 6841667
    Abstract: The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.
    Type: Grant
    Filed: July 7, 2003
    Date of Patent: January 11, 2005
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, Makoto Tokunaga, Jay F. Larrow
  • Patent number: 6800766
    Abstract: The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.
    Type: Grant
    Filed: July 26, 2002
    Date of Patent: October 5, 2004
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, Makoto Tokunaga, Jay F. Larrow
  • Patent number: 6749988
    Abstract: Novel amine compounds having a nitrogen-containing cyclic structure and a hydrating group such as a hydroxy, ether, ester, carbonyl, carbonate group or lactone ring are useful for use in resist compositions for preventing a resist film from thinning and also for enhancing the resolution and focus margin of resist.
    Type: Grant
    Filed: November 28, 2001
    Date of Patent: June 15, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tomohiro Kobayashi, Takeru Watanabe, Takeshi Nagata
  • Patent number: 6743564
    Abstract: Amine compounds having a cyano group are useful in resist compositions for preventing a resist film from thinning and also for enhancing the resolution and focus margin of resist.
    Type: Grant
    Filed: December 6, 2001
    Date of Patent: June 1, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tomohiro Kobayashi, Takeru Watanabe
  • Patent number: 6573388
    Abstract: This invention is related to new ethylaziridine derivatives of formula (I) and their preparation. The compounds are useful synthetic intermediates for the synthesis of HIV protease inhibitors and oligopeptide mimetics.
    Type: Grant
    Filed: February 18, 2002
    Date of Patent: June 3, 2003
    Assignee: Samchully Pharm. Co., Ltd.
    Inventors: Byung Moon Kim, Sung Jin Bae, Soon Mok So, Jae Sung Kang, Joong Hwan Lee
  • Patent number: 6559323
    Abstract: A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I), wherein X is oxygen, NR4 or CHR5; R1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R2 is hydrogen, alkyl, aryl, heteroaromatic, CO2R8, CHR14NHR13, heterocyclic or cycloalkyl; or R1 and R2 join together to form a cycloalkyl ring; R3 and R10 are, independently, hydrogen, alkyl, aryl, heteroaromatic, CO2R8, R83Sn, CONR8R9, trialkylsilyl or triarylsilyl; R4 is an electron withdrawing group; R5 is alkyl, cycloalkyl, aryl, heteroaromatic, SO2R8, SO3R8, COR8, CO2R8, CONR8R9, PO(R8)2, PO(OR8)2 or CN; R8 and R9 are independently alkyl or aryl; and R13 and R14 are independently hydrogen, alkyl or aryl is provided. The process comprises degrading a compound of formula (II), (IIa), (IIb) or (IIc): wherein R3 and R10 are as defined above; Y is a cation; depending on the nature of Y, r is 1 or 2; and L is a suitable leaving group, to form a diazo compound.
    Type: Grant
    Filed: February 28, 2000
    Date of Patent: May 6, 2003
    Assignees: Avecia Limited, University of Sheffield
    Inventors: John Richard Studley, Varinder Kumar Aggarwal
  • Patent number: 6500250
    Abstract: Organometallic compounds useful for forming aluminum films by chemical vapor deposition are disclosed. Also disclosed are methods of preparing the organometallic compound and methods of forming aluminum films. The compounds are selected from R′R″R′″Al:Ln wherein R′, R″, R′″ are independently selected from alkyl, perfluroalkyl or alkoxy or borate. L is one or more organic Lewis bases selected from thiophene, thriopyran and, or as defined in the instant specification.
    Type: Grant
    Filed: April 29, 2002
    Date of Patent: December 31, 2002
    Assignee: Rohn and Haas Company
    Inventor: Hyun-Koock Shin
  • Patent number: 6448414
    Abstract: The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.
    Type: Grant
    Filed: July 5, 2001
    Date of Patent: September 10, 2002
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, Makoto Tokunaga, Jay F. Larrow
  • Patent number: 6262278
    Abstract: The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.
    Type: Grant
    Filed: August 14, 1998
    Date of Patent: July 17, 2001
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, Makoto Tokunaga, Jay F. Larrow
  • Patent number: 6048979
    Abstract: Aziridines may be subjected to a cyclooligomerization reaction to produce polyazacycloalkane compounds useful for example in the preparation of chelating agents for use in diagnostic imaging contrast agents. N-benzyl-aziridine in particular is useful as it can be cyclotetramerized and debenzylated to yield cyclen, a key intermediate in chelating agent preparation. The invention provides a particularly attractive route to production of N-benzyl and other N-arylmethyl aziridines of formula (I) where each R.sub.1 is independently hydrogen or a group AR and Ar is an optionally substituted phenyl group. The process comprises reacting a purified N-arylmethylethanolaminesulphonate ester with a base. N-arylmethyl-ethanolamine sulphonate ester of the formula R'NHCH.sub.2 CH.sub.2 OSO.sub.3 H, wherein the N-arylmethyl group R' is an N-(bisarylmethyl) or N-(triarylmethyl) group, as intermediates. In a further aspect, the invention provides compounds of formula (II) ##STR1## where Ar and R.sub.
    Type: Grant
    Filed: December 2, 1997
    Date of Patent: April 11, 2000
    Assignees: Nycomed Salutar, Inc., University of Iowa Foundation
    Inventors: Janis Vasilevskis, John Varadarajan, Martha Garrity, Jere Douglas Fellmann, Louis Messerle, Gandara Amarasinghe
  • Patent number: 5929232
    Abstract: The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic chiral catalyst to produce a stereoisomerically or regioselectively enriched product.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: July 27, 1999
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, James L. Leighton, Luis E. Martinez
  • Patent number: 5852205
    Abstract: Production of aziridines comprising reacting an ethylenically unsaturated compound, such as styrene or methyl cinnamate, with a nitrene donor, such as (N-(p-tolylsulphonyl) imino) phenyliodinane in the presence of an acidic zeolitic material having a pore size large enough for the reactants to enter, and the aziridination product to leave, the zeolite supercage, said zeolite having been impregnated, or preferably exchanged, with ions of at least one metal selected from Groups VIA, VIIA, VIII, IB and IIB of the 4th to the 6th periods of the Periodic Table. The metal is preferably copper and the zeolite is preferably zeolite Y.Asymmetric aziridines may be made by treating the catalyst with a chiral modifier such as a 4,4'-disubstituted bis(oxazoline) before contact with the nitrene donor.
    Type: Grant
    Filed: September 22, 1997
    Date of Patent: December 22, 1998
    Assignee: Imperial Chemical Industries PLC
    Inventors: Donald Bethell, Graham John Hutchings, Christopher Langham, Philip Charles Bulman Page, Darren Frank Lee
  • Patent number: 5703246
    Abstract: A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I) wherein, X is oxygen, NR.sup.4 or CHR.sup.5 ; R.sup.1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R.sup.2 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, CHR.sup.14 NHR.sup.13, heterocyclic or cycloalkyl; or R.sup.1 and R.sup.2 join together to form a cycloalkyl ring; R.sup.3 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, R.sup.8.sub.3 Sn, CONR.sup.8 R.sup.9 or trimethylsilyl; R.sup.4 and R.sup.5 are, independently, alkyl, cycloalkyl, aryl, heteroaromatic, SO.sub.2 R.sup.8, SO.sub.3 R.sup.8, COR.sup.8, CO.sub.2 R.sup.8, CONR.sup.8 R.sup.9 or CN, or R.sup.4 can also be P(O)(aryl).sub.2 ; R.sup.8 and R.sup.9 are independently alkyl, aryl or arylalkyl; R.sup.13 and R.sup.14 are independently hydrogen, alkyl or aryl; the process comprising reacting a mixture of a compound of formula (II), wherein R.sup.1, R.sup.2 and X are as defined above, and a sulphide of formula SR.sup.6 R.
    Type: Grant
    Filed: March 15, 1996
    Date of Patent: December 30, 1997
    Assignee: Zeneca Limited
    Inventors: Varinder Kumar Aggarwal, Hesham Nimer Hasan Abdel-Rahman, Hee Yoon Lee
  • Patent number: 5693825
    Abstract: A process for the preparation of an aziridine, especially ethyleneimine but also its derivatives in which one or both of its carbon atoms may be substituted once or twice by C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl or aryl, and the nitrogen atom is substituted by hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl benzyl, C.sub.1 -C.sub.8 -hydroxyalkyl or C.sub.1 -C.sub.8 - aminoalkyl wherein ethanolamine or its derivatives bearing the same carbon and nitrogen substituents is reacted in the gas phase for dehydration at from 200.degree. to 600.degree. C. and from 0.001 to 5 bar, especially 0.1 to 1 bar, over a heterogeneous catalyst shaped as presintered moldings and maintained as a steady-state or as a circulating fluidized bed catalyst. The preferred fluidizable presintered moldings are those prepared from a ceramic powder as a catalyst or catalyst carrier having a uniform pore size in the macroporous range.
    Type: Grant
    Filed: August 30, 1996
    Date of Patent: December 2, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Dingerdissen, Gunter Lauth, Peter Trubenbach, Ulrich Steuerle
  • Patent number: 5646295
    Abstract: The invention concerns diazapentalene derivatives of formula I ##STR1## in which X and Y represent leaving groups which are less nucleophilic than thiol compounds, as thiol-specific fluorochromes for the detection of compounds containing thiol groups, in particular in cells.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: July 8, 1997
    Assignee: Boehringer Mannheim GmbH
    Inventors: Rudolf Gompper, Manfred Kubbies, Axel Schmidt, Bernhard Virnekas
  • Patent number: 4977118
    Abstract: A method for regeneration of catalyst which comprises phosphorus and alkali metal element and/or alkaline earth metal element and was deteriorated by use to produce aziridine compound represented by the general formula ##STR1## wherein R is hydrogen, a methyl group or an ethyl group, by a catalytic vapor-phase intramolecular dehydration reaction of alkanolamine represented by the general formula ##STR2## wherein R is as defined in the formula (II), X is OH or NH.sub.2, and Y is either NH.sub.2 when X is OH or OH when X is NH.sub.2, characterized in that the deteriorated catalyst is contacted with gaseous volatile phosphorus compound.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: December 11, 1990
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Hideaki Tsuneki, Kimio Ariyoshi, Atusi Moriya, Michio Ueshima
  • Patent number: 4918199
    Abstract: This disclosure describes an improved process for preparing N,N', N"-triethylenethiophosphoramide by the in situ generation of ethyleneimine.
    Type: Grant
    Filed: January 21, 1988
    Date of Patent: April 17, 1990
    Assignee: American Cyanamid Company
    Inventor: John Kazan
  • Patent number: 4841060
    Abstract: Catalytic vapor phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR1## wherein each of R and R' is selected from hydrogen, a methyl group and an ethyl group, and n is an integer of 2 to 5, to convert it into a cyclic amine represented by the general formula ##STR2## wherein R, R' and n are as defined above. The catalyst is an oxide composition represented by the following formulaSi.sub.a X.sub.x Y.sub.y O.sub.bwherein Si is silicon, X is at least one element selected from alkali metals and alkaline earth metals, Y is at least one element selected from B, Al, Ti, Zr, Sn, Zn and Ce, and O is oxygen; and the suffixes a, x, y and b represent the atomic ratios of the elements Si, X, Y and O respectively, and when a=1, x=0.0005-1 and y=0-1, and b is a value determined by a, x and y.
    Type: Grant
    Filed: April 15, 1988
    Date of Patent: June 20, 1989
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Youichi Hino, Yuuji Shimasaki, Michio Ueshima
  • Patent number: 4841061
    Abstract: A process for producing a cyclic amine represented by the general formula ##STR1## wherein each of R and R' is selected from hydrogen, a methyl group and an ethyl group, and n is an integer of 2 to 5, which comprises vapor-phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR2## wherein R, R' and n are as defined above, said reaction being carried out in the presence of, as a catalyst, an oxide composition represented by the following formulaX.sub.a P.sub.b Y.sub.c O.sub.dwherein X is at least one element selected from transition metal elements of Groups I through VIII, lanthanide elements, actinide elements and elements of Group IIIA in the periodic table, Si, Ge, Sn, Pb, Sb and Bi, P is phosphorus, Y is at least one element selected from alkali metal elements and alkaline earth metal elements, O is oxygen, the suffixes a, b, c and d are the atomic ratios of the elements X, P, Y and O respectively, and when a=1, b=0.01-6, preferably 0.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: June 20, 1989
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuuji Shimasaki, Michio Ueshima, Hideaki Tuneki, Kimio Ariyoshi
  • Patent number: 4833248
    Abstract: A catalyst for the vapor phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR1## wherein each of R and R' is selected from hydrogen, a methyl group and an ethyl group, and n is an integer of 2 to 5,to convert it into a cyclic amine represented by the general formula ##STR2## wherein R, R' and n are as defined above. The catalyst is an oxide composition represented by the following formulaX.sub.a P.sub.b Y.sub.c O.sub.dwherein X is at least one element selected from alkali metals and alkaline earth metals, P is phosphorus, Y is at least one element selected from B, Al, Si, S, Sc, Ti, Cu, Y, Zr, Nb, Mo, Sn, Sb, La, Ce, Ta, W, Tl, Pb, Bi and Th, O is oxygen, the suffixes a, b, c and d represent the atomic ratios of the elements X, P, Y and O, and when a=1, b=0.01-3 and c=0-100, and d is a value determined by a, b and c and the state of bonding of the constituent elements.
    Type: Grant
    Filed: March 2, 1988
    Date of Patent: May 23, 1989
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuuji Shimasaki, Hideaki Tuneki, Youichi Hino, Hitoshi Yano, Michio Ueshima
  • Patent number: 4795627
    Abstract: The present invention describes novel tritium labelled nitrogen mustard type compounds, and their aziridinium type analog, and a process for the production of same. The compounds are of value in medical research and development and also as active ingredients of pharmaceutical compositions. The compounds can be used to develop analogs of human disease states and can also be used to evaluate the mechanism of neurotransmitter regulation and function, both in vitro and in vivo.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: January 3, 1989
    Assignee: University of Pittsburgh
    Inventors: Abraham Fisher, Israel Hanin, Donald J. Abraham
  • Patent number: 4774218
    Abstract: A catalyst for the vapor phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR1## wherein each of R and R' is selected from hydrogen, a methyl group and an ethyl group, and n is an integer of 2 to 5, to convert it into a cyclic amine represented by the general formula ##STR2## wherein R, R' and n are as defined above. The catalyst is an oxide composition represented by the following formulaX.sub.a P.sub.b Y.sub.c O.sub.dwherein X is at least one element selected from alkali metals and alkaline earth metals, P is phosphorus, Y is at least one element selected from B, Al, Si, S, Sc, Ti, Cu, Y, Zr, Nb, Mo, Sn, Sb, La, Ce, Ta, W, Tl, Pb, Bi and Th, O is oxygen, the suffixes a, b, c and d represent the atomic ratios of the elements X, P, Y and O, and when a=1, b=0.01-3 and c=0-100, and d is a value determined by a, b and c and the state of bonding of the constituent elements.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: September 27, 1988
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuuji Shimasaki, Hideaki Tuneki, Youichi Hino, Hitoshi Yano, Michio Ueshima