2-(9-fluorenonyl)-carbapenem intermediates

Details 2-(9-fluorenonyl)-carbapenem intermediates 2-(9-fluorenonyl)-carbapenem intermediates

1992-10-26

1994-10-18

Richter, Johann

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540302, A01N 4300, A61K 31395, C07D48700

Patent

active

053568893

ABSTRACT:
Disclosed are carbapenems of the formula ##STR1## which are 2-(9-fluorenonyl)-carbapenems useful as antibacterial agents. Intermediates for preparation of these compounds is also disclosed.

REFERENCES:
patent: 4260627 (1981-04-01), Christensen et al.
patent: 4465632 (1984-08-01), Christensen et al.
patent: 4543257 (1985-09-01), Cama et al.
patent: 4675317 (1987-06-01), DiNinno et al.
patent: 4775669 (1988-10-01), Cama et al.
patent: 4892869 (1990-01-01), Christensen et al.
patent: 4962101 (1990-10-01), DiNinno et al.
patent: 4988703 (1991-01-01), Norbeck et al.
patent: 5003099 (1991-03-01), Mettler et al.
patent: 5011832 (1991-04-01), DiNinno et al.
patent: 5011848 (1991-04-01), Semeraro et al.
patent: 5015260 (1991-05-01), Tamura et al.
patent: 5023250 (1991-06-01), Adams et al.
patent: 5025006 (1991-06-01), DiNinno
patent: 5025007 (1991-06-01), Greenlee et al.
patent: 5026869 (1991-06-01), Flaugh
patent: 5034384 (1991-07-01), Greenlee et al.
Ihara et al. J Chem Soc Chem Commun. 1988 pp. 9-10.
Bayles, R. et al. "A Versatile Synthesis of Carbapenems from Substituted Dihydropyrans" Tet// :et/ 20(48):6345-6348 (1988).
Bender, D. R. et al. "Diastereoselective Routes to a 1.beta.-Methylcarbapenem Key Intermediate, Scope of Ate Complex Formation between Exter Enolates and Organoboranes and -alanes" J. Org. Chem. 57:2411-2418 (1992).
Bryce, M. R. et al. "Electrophilic Fluorination of Tin and Mercury Derivatives as a Route to Fluoroaromatics" Bull. Soc. Chi. 6:930-932 (1986).
Cama, L. D. et al. "Total Synthesis of Thienamycin Analogs-III Syntheses of 2-Aryl and 2-Heteroaryl Analogs of Thienamycin" Tetrahedron 39(15): 2531 to 2549 (1983).
Endo, M. "Syntheses of Chiral Intermediates of 1.beta.-Methylcarbapenems: (3S),4R)-3-[1(R)-tert-butyldimethylsilyoxyethyl]-4-chloroazetidin-2-one and (3S,4S)-3-[1(R)-tert-butyldimethylsilyloxyethyl]4][1(R)-tert-butylthio carbonylethyl]azetidin-2-one"Can. J. Chem. 65: 2140-2145 (1987).
Endo, M. "1.beta.-Methylcarbapenem Intermediates. Stereoselective Synthesis of (3S,4R)-3-[1(R)-Tert-Butyldimethylsilyoxyethyl]-4-](1R)-3-Methoxycarbonyl- 1-Methyl-2-Oxopropylazetidin-2-one and its Related Chemistry"Can. J. Chem. 66: 1400-1404 (1988).
Deziel, R. et al. "An Expeditious Synthesis of a 1.beta.-Methylcarbapenem Key Intermediate" Tet. Let. 29(1):61-64(1988).
Fuentes, L. M. et al. "A Sterocontrolled Synthesis of an Important Intermediate for the Preparation of 1.beta.-Methylcarbapenem Antibiotics" J. Org. Chem. 52:2563-2567 (1987).
Guthikonda, R. N. et al. "Structure-Activity Relationships in the 2-Arylcarbapenem Series: Synthesis of 1-Methyl-2-Arylcarbapenems" J. Med. Chem. 30: 871-880 (1987).
Hatanaka, M. "A Stereoselective Approach to 1.beta.-Methylcarbapenem Antibiotic Starting from (R)-(-)-3-Hydroxybutyric Acid Ester" Tet. Let. 28(1): 83-86 (1987).
Ihara, M. et al. "Enantioselective Synthesis of the Key Intermediate of a 1.beta.-Methycarbapenem Antibiotic by Way of Nitrone 1,3-Dipolar Cycloaddition" J. Chem. Soc. Perkin Trans I 2215-2221(1989).
Ihara, M. et al. "Highly Stereocontrolled Synthesis of the Key Intermediate of 1.beta.-Methylcarbapenem Antibiotic via Intramolecular Nitrone 1,3-Dipolar Cycloaddition" J. Chem. Soc. Chem. Commun. 9-10 (1988).
Iimori, T. et al. "Simple, Stereocontrolled Synthesis of 1.beta.Methylcarbapenem Antibiotics from 3(R)-Hydroxybutyric Acid" Tet. Let. 27(19): 2149-2152 (1986).
Ito, Y. et al. "Highly Stereocontrolled Synthesis of the 1.beta.-Methylcarbapenem Key Intermediate by the Reformatsky Reaction of 3-(2-Bromopropionyl-2-Oxazolidone Derivatives with a 4-Acetoxy-2-Azetidinone" Tet. Let. 47(16/17): 2801-2820 (1991).
Ito, Y. et al. "A Highly Stereoselective Synthesis of a Key Intermediate of 1.beta.-Methylcarbapenems Employing the Reformatsky Reaction of 3-(2-Bromopropionyl)-2-Oxazolidone Derivatives" Tet. Let. 28(52): 6625-6628 (1987).
Kaga, H. et al. "A Stereoselective Route to the Key Intermediate of 1.beta.-Methylcarbapenems by Chemicoenzymatic Approach" Tet. Let. 30(1): 113-116 (1989).
Kawabata, T. et al. "A Novel and Efficient Synthesis of the Key Intermediate of 1.beta.-Methylcarbapenem Antibiotics from (S)-Methyl 3-Hydroxy-3-Methylpropionate" Tet. Let. 27(51): 6241-6244 (1986).
Kim, C. U. et al. "Stereoselective Synthesis of 1.beta.-Methylcarbapenem" Tet. Let. 28(5) 507-510 (1987).
Kitamura, M. et al. "Stereoselective Synthesis of a Precursor of 1.beta.-Methylcarbapenems" Tet. Let. 31(4): 549-552 (1990).
Kobayashi, Y. et al. "A Highly Stereoselective Synthesis of the 1.beta.-Methycarbapenem Key Intermediate from (R)-3-Hydroxybutyric Acid" Tet. Let. 48(1): 55-66 (1992).
Martel, A. et al. "2-Picolyl Thioesters; a useful Synthon for the preparation of 1-.beta.-Alkyl Carbapenem Intermediates" Can. J. Chem. 66: 1537-1539 (1988).
Nagao, Y. et al. "Highly Diastereoselective Alkylation onto 4-Acetoxy-2-Azetidinones Employing Tin(II) Enolates of C4-Chiral 3-Acyl-1,3-Thiazolidine-2-Thiones" J. Am. Chem. Soc. 108: 4673-4675 (1986).
Ohta, T. et al. "Asymmetric Hydrogenation of Unsaturated Carboxylic Acids Catalyzed by BINAP-Ruthenium (II) Complexes" J. Org. Chem. 52: 3174-3176 (1987).
Kawabata, T. et al. "A Novel and Efficient Synthesis of the Key Intermediate of 1.beta.-Methylcarbepenem Antibiotics Employing [2+2]-Cycloaddition Reaction of Diketene with a Chiral Imine" Tet. Let. 44(8): 2149-2165 (1988).
Prasad, J. S. et al. "Acyclic Stereochemical Control Using Hexacarbonyldicobalt Stabilized Propargyl Cations. A Highly Stereoselective Route to 1.beta.-Methylcarbapenem Precursors" Tet. Let. 28(17): 1857-1860 (1987).
Rama Rao, A. V. et al. "A Simple Route to the Key Intermediate of 1.beta.-Methyl Thienamycin" Tetrahedron: Asymmetry 2(4): 255-256 (1991).
Rama Rao, A. V. et al. "Stereocontrolled Approaches to the Key Intermediate of 1.beta.-Methylthienamycin" Tet. Let. 31(2): 271-274 (1990).
Shibata, T. et al. "Synthetic Study of 1-Substituted Carbapenem Antibiotics" Tet. Let. 26(39): 4739-4742 (1985).
Sowin, T. J. et al. "Enantioselective Synthesis of the 1.beta.-Methylcarbapenems via Cycoaddition of 3-Siloxypentadiene and 4-Acetoxyazetidinone" J. Org. Chem. 53: 4154-4156 (1988).
Shirai, F. et al. "A Novel, Double-Asymmetric Aldol Approach to the Synthesis of a 1.beta.-Methyl Carbapenem Antibiotic Precursor" Tet. Let. 29(49): 6461-6464 (1988).
Shirai, F. et al. "A New Approach to the Chiral Synthesis of the 1.beta.-Methylcarbapenem Key Precursor Using an Achiral Ketone Sn(II) Enolate" J. Org. Chem. 52: 5491-5492(1987).
Shirai, F. et al. "A New Synthetic Route to the Key Precursor of 1.beta.-Methylcarbapenem Antibiotics from (S)=-Methyl 3-Hydroxy-2-Methylpropanoate" Chem. Let. 445-448 (1989).
Udodong, U. E. et al. "Formal Total Synthesis of 1.beta.-Methylcarbapenem via a Novel Route to Deoxyamino Sugars" J. Org. Chem. 54: 2103-2112 (1989).
Udodong, U. E. et al. "Electrophilic Amination as a Route to Deoxyamino Sugars: Synthesis of the Key Intermediate for 1.beta.-Methylcarbapenem" J. Org. Chem. 53: 2131-2132 (1988).
Uyeo, S. et al. "A Simple and Stereocontrolled Synthesis of a 1.beta.-Methylcarbapenem Key Intermediate by Means of Organosilicon Chemistry" Tet. Let. 32(19): 2143-2144 (1991).

Affiliated with

Also associated with

Rating

2-(9-fluorenonyl)-carbapenem intermediates does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 2-(9-fluorenonyl)-carbapenem intermediates, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-(9-fluorenonyl)-carbapenem intermediates will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2372558