Chemistry and Biochemistry

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  • Inventor(s):
    Marvin J. Miller
    Patent Number:
    US 4820815 B2
    Description:

    The invention provides azetidinones of the formula ##STR1## where R.sub.4 is hydrogen, amino or protected amino; R.sup.0 is H when R.sub.4 is amino or protected amino, or C.sub.1 -C.sub.4 alkyl when R.sub.4 is H; R.sub.1 is H, CH.sub.3, –CH.sub.2 –.sub.n Y where Y is OH, protected OH, –CH.sub.2 OH, protected –CH.sub.2 OH, halogen, COOH or protected COOH; n is 1 or 2; –CH.sub.2 –C(O)SR.sub.1 ‘ where R.sub.1 ’ is e.g., C.sub.1 -C.sub.4 alkyl; R.sub.2 is H or protecting group and R…

    Date Issued:
    1989-04-11
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Chi-Nung W. Hsiao, Marvin J. Miller
    Patent Number:
    US 4845229 B2
    Description:

    A stereoselective process for chiral intermediates to 1-carbapenem and 1-carbacephalosporins is provided comprising the use of an N-acyl-(4R)-substituted-1,3-thiazolidine-2-thione as a chiral auxiliary in boron enolate mediated aldol condensation with a protected-.beta.-keto ester aldehyde. E.g., benzyl 3,3-(ethylenedioxy)-4-formylbutyrate is condensed with the boron enolate formed with n-butyryl (4R)-methoxycarbonyl-1,3-thiazolidine-2-thione to provide benzyl 3,3-ethylenedioxy-(5R)-hydroxy-6…

    Date Issued:
    1989-07-04
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Julia M. Dolence, Manuka Ghosh
    Patent Number:
    US 5783689 B2
    Description:

    5’-O-Acyl-5-fluorouridines and 5’-O-acyl-5-sluorocytidines are prepared by the direct acylation of the 5’-hydroxyl group with amino acids under Mitsunobu conditions and the amino acyl derivatives are coupled with other amino acids or peptides to provide antibacterial and antifungal derivatives of the nucleosides. For example, 5-fluorouridine is acylated at the 5’-hydroxyl group with an amino protected L-valine and the acylation product is deprotected to provide 5’-O-(L-val…

    Date Issued:
    1998-07-21
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Matthew A. Williams
    Patent Number:
    US 5051502 B2
    Description:

    1-Carbapenam-2-one-3-carboxylic acid and 1-carba-3-hydroxy-3-cephem-4-carboxylic acid and esters thereof are provided by a process comprising a rhodium C.sub.2 -C.sub.10 carboxylate catalyzed cyclization of an ester of a 4-(1-alkoxy- or 1-substituted alkxoy)-2-oxo-4-azetidinyl)-.alpha.-diazo-.beta.-ketobutyric acid and an ester of a 5-(1-alkoxy- or 1-substituted alkoxy-2-oxo-4-azetidinyl)-.alpha.-diazo-.beta.-ketovaleric acid respectively. The process is carried out in an inert organic solven…

    Date Issued:
    1991-09-24
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Garrett C. Moraski, Jonathan Stefely
    Patent Number:
    US 8729270 B2
    Description:

    Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to anti-cancer compounds, synthesis thereof, and methods of using same. Disclosed herein are various heterocyclic compounds and methods of using the novel anti-cancer compounds to inhibit the growth of a cancer cell, for instance a leukemia, non-small cell lung, central nervous system (CNS), skin, ovarian, renal, prostate, breast, or colon cancer cell. Other embodiments include methods of treating cancer in…

    Date Issued:
    2014-05-20
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Garrett C. Moraski, Lowell D. Markley, George E. Davis
    Patent Number:
    US 9309238 B2
    Description:

    Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to imidazopyridine compounds, synthesis thereof, and methods of using same. Disclosed herein are various imidazo[1,2-a]pyhdine compounds and methods of using the novel compounds to treat or prevent tuberculosis in a subject or to inhibit fungal growth on plant species. Other embodiments include methods of synthesizing imidazo[1,2-a]pyridine compounds, such as the disclosed imidazo[1,2-a]pyridine compounds.

    Date Issued:
    2016-04-12
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Rohit Tiwari
    Patent Number:
    US 9708339 B2
    Description:

    A compound, having the following formula: ##STR00001## or resonance form thereof, or salt thereof, or salt of resonance form thereof is provided, wherein E includes an electrophilic site, and wherein R.sup.1-R.sup.4 and n are defined herein. Compositions and methods including the compound are also provided.

    Date Issued:
    2017-07-18
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Garrett C. Moraski
    Patent Number:
    US 9617249 B2
    Description:

    Embodiments herein provide compounds and methods of making and using such compounds for prevention and treatment of multidrug resistant bacteria. In particular, embodiments are directed to anti-bacterial agents from benzo[d]heterocyclic scaffolds for prevention and treatment of multidrug resistant bacteria.

    Date Issued:
    2017-04-11
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Garrett C. Moraski, Lowell D. Markley, George E. Davis
    Patent Number:
    US 9908876 B2
    Description:

    Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to imidazopyridine compounds, synthesis thereof, and methods of using same. Disclosed herein are various imidazo[1,2-a]pyhdine compounds and methods of using the novel compounds to treat or prevent tuberculosis in a subject or to inhibit fungal growth on plant species. Other embodiments include methods of synthesizing imidazo[1,2-a]pyridine compounds, such as the disclosed imidazo[1,2-a]pyridine compounds.

    Date Issued:
    2018-03-06
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller
    Patent Number:
    US 4595532 B2
    Description:

    N-Mono or N-disubstituted methyl-2-azetidinones are provided via cyclization of .beta.-hydroxy or .beta.-halo substituted acid sec-amides wherein the amide nitrogen is substituted with a mono- or di-substituted methyl group having activating substituents. Cyclization of .beta.-hydroxy acid amides is mediated by triphenylphosphine-dialkylazodicarboxylate while cyclization of .beta.-halo acid amides is mediated by strong bases e.g. lithium dialkylamides. E.g. Diethyl amino-protected L-serylamin…

    Date Issued:
    1986-06-17
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Jingdan Hu
    Patent Number:
    US 6403623 B2
    Description:

    Method for treating tuberculosis with 2-(2-substituted-phenyl)-2-oxazolines and related 5-membered heterocycles represented by the formula ##STR1## Y.sub.1 is e.g. an ester or amide forming group, and X is O, S, or NH; and pharmaceutically acceptable formulations useful therein are provided. A preferred method comprises administering (S)-benzyl2-[2-(benzyloxy)phenyl]-2-oxazoline-4-carboxylate in a suitable formulation. The compounds of the above formula are prepared by known methods, e.g. the…

    Date Issued:
    2002-06-11
    Record Visibility:
    Public
    Resource Type
    Patent
  • Inventor(s):
    Min Teng, Marvin J. Miller
    Patent Number:
    US 5750681 B2
    Description:

    Bicyclic .beta.-lactams comprising a 5- or 6-membered lactone or lactam ring are obtained in a process comprising a base induced intramolecular cyclization of a 4-substututed .beta.-lactam having a leaving group in the 1-position. An intramolecular nucleophile transfer reaction is proposed as the operative mechanism and the bicyclic .beta.-lactams are obtained in the required stereochemical form for biological activity. The compounds provided are useful intermediates for the preparation of an…

    Date Issued:
    1998-05-12
    Record Visibility:
    Public
    Resource Type
    Patent