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  • 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…

    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Yanping Xu
    Patent Number:
    US 6310058 B2
    Description:

    Compounds represented by the formula [1] ##STR1## R.sub.1 is H or a substituent; R.sub.2 and R.sub.3 are C.sub.1 -C.sub.3 alkyl; R.sub.4 is siderophore group e.g. CH.sub.3 –(CH.sub.2).sub.n –C(O)–N(OH)–(CH.sub.2).sub.m – with n=10-22, m=2-6; X is O, S, or NH; X.sub.1 is O or NH; Y is H or alkyl; Z is H or substituted amino, e.g., t-BocNH or CbzNH, and r is 2-4; are useful in the method provided for treating tuberculosis. [1] is prepared by coupling [7], wherein HX.sub.1 is HO– or H.sub….

    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…

    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…

    Resource Type
    Patent
  • Inventor(s):
    Catherine M. Gasparski, Marvin J. Miller, Min Teng
    Patent Number:
    US 5250676 B2
    Description:

    Provided is a process for diastereoselectively preparing compounds of the formula ##STR1## which includes the step of subjecting a compound of the formula ##STR2## to a salt whose anion is a nucleophilic base whose conjugate acid has a pKa in the range of between about -7 to about 14, or a silylated derivative of the salt; wherein R.sub.1 is said nucleophile; R is hydrogen, or protected amino, R.sub.2 is R.sub.4 as defined herein below; R.sub.3 is a leaving group; and R.sub.4 is hydrogen, C.s…

    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…

    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller, Matthew A. Williams
    Patent Number:
    US 5106968 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 alkoxy)-2-oxo-4-azetidinyl)-.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 solvent at a tempera…

    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller
    Patent Number:
    US 5266468 B2
    Description:

    .beta.-Hydroxy-.alpha.-amino acids are obtained via serine hydroxymethyltransferase catalyzed condensation of aldehydes with glycine. The predominant product with most aldehydes is the L-erythro diastereomer. For example, succinic semialdehyde methylester is condensed with glycine in the process to provide L-erythro .alpha.-amino hydroxy adipic acid mono methyl ester.

    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…

    Resource Type
    Patent
  • Inventor(s):
    Marvin J. Miller
    Patent Number:
    US 4992544 B2
    Description:

    Monocyclic .beta.-lactam compounds represented by the formula ##STR1## wherein R.sub.1 is H, NH.sub.2, acylamino, C.sub.1 -C.sub.4 alkyl, etc.; R.sub.2 is e.g. C.sub.1 -C.sub.4 alkyl, hydroxyalkyl, aminoalkyl, carboxy, esterified carboxy, esterified carboxyalkyl, or carboxyalkyl; and R.sub.3 is hydrogen, benzyl, substituted benzyl, pivaloyl, –SO.sub.3 M, or –P(C.dbd.O)(OM’)2; are obtained by the cyclization of an O-substituted hydroxamate of a .beta.-substituted alkylcarboxylic acid. Fo…

    Resource Type
    Patent
  • 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…

    Resource Type
    Patent
  • Inventor(s):
    Chi-Nung W. Hsiao, Marvin J. Miller
    Patent Number:
    US 4745201 B2
    Description:

    A stereoselective process for chiral intermediates to 1-carbapenum 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…

    Resource Type
    Patent