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US 5,854,213 AGranted
Antifungal cyclohexapeptides
AssigneeMerck & Co., Inc.
InventorFrances A. Bouffard
Life of this patent
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Abstract
The present invention is directed to novel carba cyclohexapeptide compounds of the formula ##STR1## where all substituents are defined herein, which are useful as antifungal agents and for the treatment of Pneumocystis carinii infections. Compositions containing the compounds of the invention are also disclosed.
Claims17
A compound having the formula ##STR35## wherein R.sub.1 is OH;
- R.sub.2 is H;
- R.sub.3 is CH.sub.2 CONH.sub.2, CH.sub.2 CN or CH.sub.2 CH.sub.2 NR.sup.II R.sup.III ;
- R.sub.4 is CH.sub.3 ;
- R.sub.5 is H;
- R.sub.6 is OH;
- R.sup.I is C.sub.9 -C.sub.21 alkyl, C.sub.9 -C.sub.21 alkenyl, C.sub.1 -C.sub.10 alkoxyphenyl, C.sub.1 -C.sub.10 alkoxynaphthyl, or ##STR36## wherein R.sup.a is C.sub.1 -C.sub.10 alkyl;
- or (CH.sub.2).sub.q NR.sup.b R.sup.c wherein R.sup.b and R.sup.c are independently H, C.sub.1 -C.sub.10 alkyl or R.sup.b and R.sup.c taken together with
- the nitrogen atom are ##STR37## wherein R.sup.d is C.sub.1 -C.sub.16 alkyl, cyclohexylmethyl, phenyl or benzyl;
- p is 1 or 2;
- and
- q is 2, 3 or 4;
- R.sup.II is H, C.sub.1 -C.sub.4 alkyl, (CH.sub.2).sub.2-4 OH, C.dbd.NH(R.sup.VII), (CH.sub.2).sub.2-4 NR.sup.V R.sup.VI, (CH.sub.2).sub.2-4 N(R.sup.IV).sub.3.sup.+ X.sup.-, (CH.sub.2).sub.2-4 NH(C.dbd.NH)R.sup.VII, (CH.sub.2).sub.1-4 CH(NR.sup.V R.sup.VI)(CH.sub.2).sub.1-4 NR.sup.V R.sup.VI, (CH.sub.2).sub.2-4 NR.sup.V (CH.sub.2).sub.2-4 NR.sup.V R.sup.VI, CO(CH.sub.2).sub.1-4 NR.sup.V R.sup.VI, COCH(NR.sup.V R.sup.VI)(CH.sub.2).sub.1-4 NR.sup.V R.sup.VI ;
- R.sup.III is H, C.sub.1 -C.sub.4 alkyl, (CH.sub.2).sub.2-4 NR.sup.V R.sup.VI, (CH.sub.2).sub.2-4 N(R.sup.IV).sub.3.sup.+ X.sup.-, (CH.sub.2).sub.2-4 NH(C.dbd.NH)R.sup.VII, (CH.sub.2).sub.1-4 CH(NR.sup.V R.sup.VI)(CH.sub.2).sub.1-4 NR.sup.V R.sup.VI, (CH.sub.2).sub.2-4 NR.sup.V (CH.sub.2).sub.2-4 NR.sup.V R.sup.VI ;
- or
- R.sup.II and R.sup.III taken together are --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --, or --(CH.sub.2).sub.2 NH(CH.sub.2).sub.2 --;
- R.sup.IV is C.sub.1 -C.sub.4 alkyl;
- R.sup.V is H or C.sub.1 -C.sub.4 alkyl;
- R.sup.VI is H or C.sub.1 -C.sub.4 alkyl;
- R.sup.VII is H, C.sub.1 -C.sub.4 alkyl or NH.sub.2 ;
- X is Cl, Br or I;
- or
- a pharmaceutically acceptable salt thereof.
19 more elements
A compound having the formula ##STR38## wherein R.sub.1 is OH;
- R.sub.2 is H;
- R.sub.3 is CH.sub.2 CONH.sub.2, CH.sub.2 CN or CH.sub.2 CH.sub.2 NR.sup.II R.sup.III ;
- R.sub.4 is CH.sub.3 ;
- R.sub.5 is H;
- R.sub.6 is OH;
- R.sup.I is C.sub.9 -C.sub.21 alkyl, C.sub.9 -C.sub.21 alkenyl, C.sub.1 -C.sub.10 alkoxyphenyl,
- C.sub.1 -C.sub.10 alkoxynaphthyl, or ##STR39## wherein R.sup.a is C.sub.1 -C.sub.10 alkyl;
- or (CH.sub.2).sub.q NR.sup.b R.sup.c wherein R.sup.b and R.sup.c are independently H, C.sub.1 -C.sub.10 alkyl or R.sup.b and R.sup.c taken together with
- the nitrogen atom are ##STR40## wherein R.sup.d is C.sub.1 -C.sub.16 alkyl, cyclohexylmethyl, phenyl or benzyl;
- p is 1 or 2;
- q is 2, 3 or 4;
- R.sup.IV is C.sub.1 -C.sub.4 alkyl;
- and
- X is Cl, Br or I.
11 more elements
A compound having the formula ##STR41## wherein R.sub.1 is OH;
- R.sub.2 is H;
- R.sub.3 is CH.sub.2 CONH.sub.2, CH.sub.2 CN or CH.sub.2 CH.sub.2 NR.sup.II R.sup.III ;
- R.sub.4 is CH.sub.3 ;
- R.sub.5 is H;
- R.sub.6 is OH;
- R.sup.II is H, C.sub.1 -C.sub.4 alkyl, (CH.sub.2).sub.2-4 OH, C.dbd.NH(R.sup.VII), (CH.sub.2).sub.2-4 NR.sup.V R.sup.VI, (CH.sub.2).sub.2-4 N(R.sup.IV).sub.3.sup.+ X.sup.-, (CH.sub.2).sub.2-4 NH(C.dbd.NH)R.sup.VII, (CH.sub.2).sub.1-4 CH(NR.sup.V R.sup.VI)(CH.sub.2).sub.1-4 NR.sup.V R.sup.VI, (CH.sub.2).sub.2-4 NR.sup.V (CH.sub.2).sub.2-4 NR.sup.V R.sup.VI, CO(CH.sub.2).sub.1-4 NR.sup.V R.sup.VI, COCH(NR.sup.V R.sup.VI)(CH.sub.2).sub.1-4 NR.sup.V R.sup.VI ;
- R.sup.III is H, C.sub.1 -C.sub.4 alkyl, (CH.sub.2).sub.2-4 NR.sup.V R.sup.VI, (CH.sub.2).sub.2-4 N(R.sup.IV).sub.3.sup.+ X.sup.-, (CH.sub.2).sub.2-4 NH(C.dbd.NH)R.sup.VII, (CH.sub.2).sub.1-4 CH(NR.sup.V R.sup.VI)(CH.sub.2).sub.1-4 NR.sup.V R.sup.VI, (CH.sub.2).sub.2-4 NR.sup.V (CH.sub.2).sub.2-4 NR.sup.V R.sup.VI ;
- or
- R.sup.II and R.sup.III taken together are --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --, or --(CH.sub.2).sub.2 NH(CH.sub.2).sub.2 --;
- R.sup.IV is C.sub.1 -C.sub.4 alkyl;
- R.sup.V is H or C.sub.1 -C.sub.4 alkyl;
- R.sup.VI is H or C.sub.1 -C.sub.4 alkyl;
- R.sup.VII is H, C.sub.1 -C.sub.4 alkyl or NH.sub.2 ;
- X is Cl, Br or I;
- or
- a pharmaceutically acceptable salt thereof.
13 more elements
Dependencies are inferred from the claim text.