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1. (WO2007002173) HIV-1 PROTEASE INHIBITORS, AND METHODS OF MAKING AND USING THEM
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/2007/002173 International Application No.: PCT/US2006/024109
Publication Date: 04.01.2007 International Filing Date: 21.06.2006
IPC:
C07D 263/24 (2006.01) ,A61K 31/421 (2006.01) ,A61P 31/18 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
263
Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
02
not condensed with other rings
08
having one double bond between ring members or between a ring member and a non-ring member
16
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
18
Oxygen atoms
20
attached in position 2
24
with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
A HUMAN NECESSITIES
61
MEDICAL OR VETERINARY SCIENCE; HYGIENE
K
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31
Medicinal preparations containing organic active ingredients
33
Heterocyclic compounds
395
having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
41
having five-membered rings with two or more ring hetero atoms, at least one of which is nitrogen, e.g. tetrazole
42
Oxazoles
421
1,3-Oxazoles, e.g. pemoline, trimethadione
A HUMAN NECESSITIES
61
MEDICAL OR VETERINARY SCIENCE; HYGIENE
P
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
31
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
12
Antivirals
14
for RNA viruses
18
for HIV
Applicants:
UNIVERSITY OF MASSACHUSETTS [US/US]; One Beacon Street, 26th Floor Boston, Massachusetts 02108, US (AllExceptUS)
RANA, Tariq, M. [US/US]; US (UsOnly)
ALI, Akbar [PK/US]; US (UsOnly)
CAO, Hong [CN/US]; US (UsOnly)
SAI, Kiran Kumar Reddy Ga [IN/US]; US (UsOnly)
ANJUM, Saima, Ghafoor [PK/US]; US (UsOnly)
Inventors:
RANA, Tariq, M.; US
ALI, Akbar; US
CAO, Hong; US
SAI, Kiran Kumar Reddy Ga; US
ANJUM, Saima, Ghafoor; US
Agent:
WASSERMAN, Jacob, I. ; Patent Group Foley Hoag LLP 155 Seaport Boulevard Boston, MA 02210-2600, US
Priority Data:
60/693,13422.06.2005US
60/749,90212.12.2005US
60/810,23402.06.2006US
Title (EN) HIV-1 PROTEASE INHIBITORS, AND METHODS OF MAKING AND USING THEM
(FR) INHIBITEURS DE LA PROTEASE DU VIH-1, ET LEURS PROCEDES DE FABRICATION ET D'UTILISATION
Abstract:
(EN) One aspect of the invention relates to the design, synthesis and biological activity of novel HIV-1 protease inhibitors incorporating N-phenyloxazolidine-5-carboxamides into the (hydroxyethylamino)sulfonamide scaffold as P2 ligands. For example, the present invention relates to inhibitors with variations at the P2 phenyloxazolidine and the P2' phenylsulfonamide moieties. Remarkably, compounds with an (S)-enantiomer of substituted phenyloxazolidines at P2 show highly potent inhibitory activities against wild-type HIV-1 protease. In certain embodiments, the inhibitors of the invention have Ki values in low picomolar (pM) range. In certain embodiments, the inhibitors of the invention were shown to be active against a variety of multi-drug resistant (MDR) HIV-1 proteases, each representing different paradigm of drug resistance.
(FR) L'invention concerne, dans un aspect, la conception, la synthèse et l'activité biologique de nouveaux inhibiteurs de la protéase du VIH-1 incorporant N-phényloxazolidine-5-carboxamides dans le squelette (hydroxyéthylamino)sulfonamide comme ligands P2. Par exemple, l'invention concerne des inhibiteurs présentant des variations au niveau des fractions de P2 phényloxazolidine et de P2' phénylsulfonamide. A relever que des composés avec un (S)-énantiomère de phényloxazolines substituées à P2 présentent des activités inhibitrices particulièrement puissantes contre la protéase de VIH-1 de type sauvage. Dans certains modes de réalisation, les inhibiteurs ont des valeurs Ki dans une gamme picomolaire basse (pM). D'autres modes de réalisation montrent des inhibiteurs actifs contre une variété de protéases du VIH-1 résistantes à plusieurs médicaments (MDR), chacun représentant un paradigme différent de résistance aux médicaments.
Designated States: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
EP1937655JP2008546790CN101309911CA2667449AU2006262275