Back to results
US 7,022,667 B2Granted
O-derivatized nocathiacin derivatives
AssigneeBristol-Myers Squibb Company
InventorsThomas W. Hudyma, Xiaofan Zheng, B. Narasimhulu Naidu, Margaret E. Sorenson, Alicia Regueiro-Ren, Timothy P. Connolly, John D. Matiskella, Oak K. Kim, Yunhui Zhang, Dane M. Springer, Jason Goodrich, Yasutsugu Ueda, Joanne J. Bronson
Life of this patent
Estimating the term…
Abstract
The present invention provides compounds of formula I having potent antibiotic activity, including activity towards Gram-positive bacteria and mycobacteria.
Claims9
A compound of Formula I, including pharmaceutically acceptable salts thereof,
- wherein:
- W is
- Z is selected from the group consisting of —NH2 and
- R1 is selected from the group consisting of
- hydrogen, —P(O)A1A2, —C(O)C1-6alkyl, —C(O)aryl, —C(O)NHC1-6alkyl, —C(O)NHaryl, —(CH2CH2O)mMe, —C1-6alkenyl, —C1-6alkynyl, and —C1-6alkyl;
- wherein said C1-6alkyl is optionally substituted by one to six hydroxy or optionally substituted by one to two same or different substituents selected from the group consisting of (a)–(i):
- (a) CO2R3;
- (b) CONR4R5;
- (c) OP(O)A1A2;
- (d) SO3H;
- (e) —O(CH2)nSiR63;
- (f) heteroalicyclic selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, and morpholinyl;
- (g) cyano;
- (h) epoxy;
- and
- (i) aryl;
- and provided that R1 and R2 are not simultaneously H;
- R2 is selected from the group consisting of
- hydrogen, —P(O)A1A2, —SO3H, —C(O)C1-6alkyl, —C(O)CH═CHCO2R3, —C(O)aryl, —C(O)N(H)(C1-6alkyl-T), —C(O)N(Me)(C1-6alkyl-T), —(CH2CH2O)pH, —(CH2CH2O)qMe, —C1-6alkenyl, —C1-6alkyl and —C1-6alkynyl;
- wherein said —C1-6alkyl is optionally substituted by one to six hydroxy or optionally substituted by one to two same or different substituents selected from the group consisting of (j)–(v):
- (j) halo;
- (k) CO2R3;
- (l) CONR4R5;
- (m) OP(O)A1A2;
- (n) P(O)A1A2;
- (O)SO3H;
- (p) —O(CH2)rSiR63;
- (q) heterocyclic or heteroalicyclic selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, imidazolyl, and pyridyl;
- (r) cyano;
- (s) azido;
- (t) aryl;
- (u) NR4R5;
- and
- (v)
- R3 is selected from the group consisting of hydrogen, C1-6alkyl, allyl, benzyl, 2-hydroxyethyl, and 2-tetrahydropyranyl;
- R4 and R5 are each independently selected from the group consisting of hydrogen, C1-6alkyl, CH2CN, CH2CH2NH(t-butyloxycarbonyl), C(═NH)NH2 and SO2N(C1-6alkyl)2;
- or R4 and R5 taken together with the nitrogen to which they are attached form a heterocyclic or heteroalicyclic selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, imidazolyl, and pyridyl;
- R6 is selected from C1-6alkyl and phenyl;
- A1 and A2 are each independently selected from the group consisting of hydrogen, —C1-6alkyl, —OC1-6alkyl, benzyloxy, 2-chloroethoxy, and hydroxy;
- T is selected from the group consisting of hydrogen, —OH, —(CH2CH2O)sH, —(CH2CH2O)tCH3 and —NR4R5;
- m, n, p, q, r, s and t are independently 1–6;
- and
- aryl consists of a phenyl group optionally substituted with halo or —CO2R3.
40 more elements
Dependencies are inferred from the claim text.