The University of North Carolina at Chapel Hill

Biotech Research Laboratories

Other

Panacos Pharmaceuticals, Inc.

Biotech Research Labs, Inc.

Niigata University of Pharmacy and Applied Life Sciences

Yoshiki Kashiwada

Kuo-Hsiung Lee

Lan Xie

Mark Manak

Li Huang

Mark Cosentino

Jim Snider

Thomas Tung-Ying Lee

Louis Mark Cosentino

Yung-Chi Cheng

Graham P Allaway

Carl Thomas Wild

Fumio Hashimoto

Mark Manax

Robert Kilkulskie

Jing-Xi Xie

Betulin and dihydrobetulin acyl derivatives according to the present invention have been found to have potent anti-HIV activity. The compounds of the present invention have Formula I as described herein, or pharmaceutically acceptable salts thereof; wherein Ris a C-Csubstituted or unsubstituted carboxyacyl or ester thereof; Ris hydrogen, halogen, hydroxyl or &#x2014;OR, Ris C-Csubstituted or unsubstituted carboxyacyl; and Ris hydrogen or C(CH); wherein the dashed line represents an optional double bond between C20 and C29.

Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof

The present invention is directed to compounds that are analogs of the natural product suksdorfin. Compounds of the present invention include those having Formula IV:

Suksdorfin analogs, compositions thereof, and methods for making and using thereof

The present invention is directed to compounds that are analogs of the natural product suksdorfin. Compounds of the present invention include those having Formula I: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined herein. The invention is also directed to methods of making these compounds, pharmaceutical compositions including these compounds and methods of using the compounds to inhibit retroviral infections in cells and tissues of animals. A method for stereoselectively preparing compounds within the scope of the invention by catalytic asymmetric dihydroxylation is also disclosed.

Suksdorfin analogs, compositions thereof, and methods for making and

Some betulinic acid and dihydrobetulinic acid acyl derivatives according to the present invention have been found to have potent anti-HIV activity. Introducing a C.sub.2 -C.sub.20 substituted or unsubstituted acyl group at the C.sub.3 -hydroxy group of betulinic acid and dihydrobetulinic acid produces the corresponding 3-O-acyl derivatives. The compounds of the present invention have the following formulae: ##STR1## where R may be a mono- or dicarboxylacyl group, substituted or unsubstituted, of from about 2 to about 20 carbon atoms, and R' may be hydrogen or a C.sub.2 -C.sub.10 substituted and unsubstituted alkyl or aryl group.

Betulinic acid and dihydrobetulinic acid derivatives and uses therefor

Compounds, including compositions and methods of making and using these compounds for treating retroviral infections, are provided according to formula (G-1): ##STR1## wherein M is O or NH; Z is O, NH or S; R.sup.240, and R.sup.250 are each H, C.sub.1-10 alkyl, C.sub.1-10 aryl, alkyl, amide, or CH.sub.2 COOR.sup.260, where R.sup.260 is C.sub.1-10 alkyl or acyl; R.sup.200, R.sup.210, R.sup.220 and R.sup.230 are each H, halogen, hydroxyl, NH.sub.2, NH-alkyl, N-(alkyl).sub.2, O-alkyl, O-acyl, COCF.sub.3, OCF.sub.3 or CH.sub.2 COO NH-alkyl; or R.sup.200 and R.sup.210 form C.sub.5 -C.sub.10 cyclo or heterocyclo optionally substituted with one or more of halogen, hydroxyl, NH.sub.2, NH-alkyl, N-(alkyl).sup.2, O-acyl, O-alkyl, CO, CF.sub.3, OCF.sub.3 or CH.sub.2 COONH-alkyl; wherein C3 and C4 can be bound by a single or double bond; configurations at 3' or 4' can be (R) or (S); and R.sup.240 and R.sup.250 are either cis-.beta. or cis.alpha., or trans-3'-.alpha. or trans-3'-.beta. oriented. Stereoselectivity can be enhanced by preparing these compounds by catalytic asymmetric dihyroxylation.

Suksdorfin, analogs, compositions thereof, and methods for making and

Disclosed herein are derivatives of 4,4'-dimethoxy-5,6,5'6'-bimethylenedioxy 2,2'-dimethoxycarbonyl biphenyl (DDB) which were synthesized and found to have anti-HIV activity. Of the compounds studied, 3,3'-dibromo DDB and 3-bromo-DDB initially exhibited the greatest anti-HIV activity.

Brominated hexahydroxybiphenyl derivatives

Growing community of inventors

Niigata, Japan

Yoshiki Kashiwada