Organic compounds -- part of the class 532-570 series – Organic compounds – Azides
Reexamination Certificate
2011-03-15
2011-03-15
Dentz, Bernard (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azides
C562S470000
Reexamination Certificate
active
07906662
ABSTRACT:
The compounds trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide and trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropanaminium (2R)-2-hydroxy-2-phenylethanoate.
REFERENCES:
patent: 4767777 (1988-08-01), Bass et al.
patent: 5286736 (1994-02-01), Soyka et al.
patent: 5929291 (1999-07-01), Bajgrowicz et al.
patent: 873 018 (1961-07-01), None
patent: WO 98/57640 (1998-12-01), None
patent: 9905143 (1999-02-01), None
patent: WO 99/05143 (1999-02-01), None
Evans, D.A., et al; “A Convergent Total Synthesis of (+−)-Colchicine and (+−) Desacetamidoisocolchicine”;J. Am. Chem. Soc.;vol. 103, No. 19, pp. 5813-5821 (1981); XP002476378.
Orr, F.G., “Inhibition o furidine Phosphorylase: Synthesis and Structure-Activity Relationships of Aryl-Substituted 5-Benzyluracils and 1-[(2-Hydroxyethoxy)methyl]-5-benzyluracils”; et al;J. Med. Chem.,vol. 38, No. 19; pp. 3850-3856 (1995) XP002476381.
Journal of the American chemicals society, vol. 87, 1965, E.J. Vorey et al, “Dimethyloxosulfonium Methylide ((CH3)2S0CH2) and Dimethylsulfonium Methlide ((CH3)2S0CH2). Formation and Application to Organic Synthesis” p. 1353-p. 1364.
Advancedd Organic Chemistry, Fourth Edition, Jerry Mark, Reactions, Mechanisms, and structure, John Wiley & Sons, New York, 1992, pp. 872, 741 pp. 428-429, pp. 1091-1095.
Organic Chemisty, Fifth Edition, T.W. Graham Solomons, John Wiley & Sons, Inc., New York, 1992, pp. 781-782, p. 775, pp. 846-848; pp. 830-832; pp. 834-835.
STN International, File CAPLUS, CAPLUS accession No. 1998: 429075, Document No. 129:135904 Diaz-Requejo et al: “BpCu-Catalyzed Cyclopropanation of Olefins: A simple System That operates under andHeterogeneous Conditions (BP = Dihydridobis (pyraxoly)borate)”; Organometallics (1998), 17(14), 3051-3057, RN 91393-54-3.
STN International, File CAPLUS, CAPLUS accession No. 1998:250346, Document No. 128:321223,Galardon, Erwan et al: “Asymmetric Cyclopropanation of a alkenes and diazocarbonyl insertion into S-H bonds catalyzed by a chiral porphyrin Ru(II) complex”; Tetrahedron Lett. (1998), 39(16), 2333-2334, Rn 207279-36-5.
STN International, File CAPLUS, CAPLUS accession No. 1995:927375, Document No. 124:116326, Demonceau, A. et al: “Cyclopropanation catalyzed by RuC13 (PPh3) and OsC12(PPh3)3”; Tetrahedron Lett. (1995), 36(46), 8419-22, RN 4103-56-4, 4103-57-5.
STN International, File CAPLUS, CAPLUS accession No. 1995:597880, Document No. 123:169063, Demonceau, A. et al: “Cyclopropanation of activated olefins catalyzed by Ru-phosphine complexes”; Tetrahedron Lett. (1995), 36(20), 3519-22, RN 4103-56-4, 4103-57-5.
STN International, File CAPLUS, CAPLUS accession No. 1998:200362, Document No. 128:270257, Kusuyama, Yoshiaki: “Solvolysis of 1-(trans-2-(m-or p-substituted phenyl) cyclopropyl)-1-methyl-ethyl p-nitrobensoates”; Bull. Chem Soc. Jpn. (1998), 71(3), 685-691, RN 4103-57-5, 205674-79-9.
Chemical Abstracts, vol. 59 (1962), (Columbus, Ohio, USA), Kaiser, Carl et al, “2-Substituted cyclopropylamines. I. Derivatives and analogs of 2-phenylcyclopropylamine”, The Abstract No. 504f, Med Pharm. Chem. 1962, 5, 1243-1265, RN 91329-59-8, 91393-53-2, 92576-45-9.
STN International, File CAPLUS, CAPLUS accession No. 2000:6701, Document No. 132:122310, Wu, Xin-Yan et al: “Asymmetric synthesis of 5-hydroxtryptamine recepter agonist (1R,2S)-(−)-2-(2-hydroxyphenyl)-N, N-dipropyl-cyclopropamine”; & Gaodeng Xuexiao Huaxue Xuebao (1999), 20(12), 1982-1896, RN256431-75-1, 256431-73-9.
Chemical Abstract, vol. 57 (1962), (Columbus, Ohio, USA), Richard Fuchs et al, “Transmision of electronic effects by the cyclopropane ring.Ionization constants of m- and p-substituted.bet.-phenylpropionic, cis-and trans-2-phenylcyclopropanecarboxylic acids in 50% ethanol”, The Abstract No. 3347I, J. Org. Chem. 1962, 27 733-736, RN 91329-60-1.
STN International, File CAPLUS, CAPLUS accession No. 1996:148289, Document No. 124:250558, Vallgaarda, Jerk et al: “trans-2-Aryl-N,N-dipropyl-cyclopropylamines: Synthesi and Interaction with 5-HT 1A Receptors”; & J. Med Chem. (1996), 39(7), 1485-93, RN175168-73-7.
Roberts et al, Basic Principles of Organic Chemistry, W.A. Benjamin, Inc., pp. 530-531 and 562 (1965).
Kaiser et al, J. Organic. Chem., vol. 30, p. 3972-3975 (1965).
Corey et al, JACS, 87:6, pp. 1353-1364 (1965).
The Merck Index, Merck & Co., p. ONR-60 (1976).
Spence, E.L., et al; “Cis-TransIsomerization of a Cyclopropyl Radical Trap Catalyzed by Extradiol Catechol Dioxygenases: Evidence for a Semiquinone Intermediate”;J. Am. Chem. Soc.;vol. 118, No. 35, pp. 8336-8343 (1996); XP002476377.
Corey, E.J., et al; “Dimethyloxosulfonium Methylide ((CH3)2soch2) and Dimethylsulfonium Methylide ((CH3)2SCH2). Formation and Application to Organic Synthesis”;Journal of the American Chemical Society,vol. 87, pp. 1353-1364 (1965); XP000916647.
March, J.; “Advanced Organic Chemistry”; New York, John Wiley & Sons, US; pp. 738-741, 428 (1992); XP002946373.
Patro, B., et al; “Acid-Induced Ring Opening of α-[Bis(methylthio)methylene]alkyl Cyclopropyl Ketones: A Novel Route to Substituted Cyclopentanones through Carbocationic cyclizations”;J. Org. Chem.,vol. 57, No. 8, pp. 2257-2263 (1992); XP002476379.
Merz, A., et al; “Phase-transfer-catalyzed Production of Sulfur Ylides in an Aqueous System”;Angew. Chem. Internat. Edit.,vol. 12, No. 10; pp. 845-846 (1973); XP002476380.
Galardon, E., et al; “Asymmetric Cyclopropanation of Alkenes and Diazocarbonyl Insertion Into S-H Bonds Catalyzed by a Chiral Porphyrin Ru(II) Complex”;Tetrahedron Letters,vol. 39, No. 16; pp. 2333-2334 (1998); XP004111165.
Demonceau et al; “Cyclopropanation Catalyzed by RuCl2(PPh3)3and OsCl2(PPh3)3”; Tetrahedron Letters,vol. 36, No. 46; pp. 8419-8422 (1995); XP005270638.
Demonceau, A., et al; “Cyclopropanation of Activated Olefins Catalysed by Ru-Phosphine Complexes”;Tetrahedron Letters,vol. 36, No. 20; pp. 3519-3522 (1995); XP004028095.
Kusuyama, Y.; “Solvolysis of 1-[trans-2-(m- orp-Substituted Phenyl)cyclopropy1]-1-methylethylp-Nitrobenzoates1)”; Bulletin of the Chemical Society of Japan;vol. 71, No. 3; pp. 685-691 (1998); XP009032176.
Kaiser, C., et al; “2-Substituted Cyclopropylamines. I. Derivatives and Analogs of 2-Phenylcyclopropylamine”;Journal of Medicinal and Pharmaceutical Chemistry;vol. 5; pp. 1243-1265 (1962); XP009032189.
Fuchs, R., et al; “Transmission of Electronic Effects by the Cyclopropane Ring. Ionization Constants ofm- andp-Substituted β-Phenylpropionic,cis-andtrans-2-Phenylcyclopropanecarboxylic Acids in 50% Ethanol”; Journalof Organic Chemistry,vol. 27, pp. 733-736 (1962); XP009032177.
Vallgarda, J., et al; “trans-2-Aryl-N,N-dipropylcyclopropylamines: Synthesis and Interactions with 5-HT1AReceptors”;Journal of Medicinal Chemistry,vol. 39, No. 7; pp. 1485-1493 (1996); XP002262871.
Database Beilstein; Beilstein Institute for Organic Chemistry, Frankfurt-Main, DE; Database Accession No. BRN 2583176 (Abstr); & Fuchs; Bloomfield:J. Org. Chem.;vol. 28; pp. 910-911 (1963); XP002476383.
Database Beilstein;Beilstein Institute for Organic Chemistry,Frankfurt-Main, DE; Database Accession No. BRN 2598637 (Abstr); & White, W.L., et al;J. Chem. Soc. C; pp. 2062-2068 (1971); XP002476384.
Filler, R., et al; “New Reactions of Polyfluoroaromatic Compounds. Part II. Polyfluoroaralkyl Amines1”; Journal of the Chemical Society, Section C: Organic Chemistry;pp. 2062-2068 (1971); XP009102773.
Coutts, R.T., et al; “Neurochemical and Neuropharmacological Properties of 4-Fluorotranylcypromine”;Cellular and Molecular Neurobiology,vol. 7, No. 3; pp. 271-290 (1987); XP009103506.
Houben-Weyl;Methoden der Organischen Chemie,fourth edition, vol. VIII, pp. 467-469 (1952); XP002489140.
Matsuda, F., et al; “Total Synthesis
Clark Adrian
Jones Elfyn
Larsson Ulf
Minidis Anna
Astrazeneca AB
Dentz Bernard
Nixon & Vanderhye
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