1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino 1,3-propanediols and related compounds
AssigneeAventis Pharmaceuticals Inc.
InventorsJohn Joseph Tegeler, Barbara Seavey Rauckman, Russell Richard Lee Hamer, Brian Scott Freed, Gregory Harold Merriman
Life of this patent
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Abstract
Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
Claims5
A method of inhibiting bacterial or fungal growth in a mammal in need of bacterial or fungal growth inhibition which comprises administering to such a mammal a bacterial or fungal growth inhibiting effective amount of a compound of the formula
- RCH(OR1)CH(NR2R3)R4 or RCH2CR35(NR2R3)R4
- wherein R is
- wherein R5 is CH3(CH2)mCΞC, CH3(CH2)mCH═CH CH3(CH3)(CH2)mCH2CH2,
- wherein m is 3 to 15, n is 0 to 12, and W and X are independently hydrogen, hydroxy, loweralkyl, loweralkoxy, halogen, or trifluoromethyl or
- wherein R23 is loweralkyl;
- R1 is hydrogen, loweralkyl,
- wherein R24 is loweralkyl or
- wherein R6 is hydrogen, loweralkyl, loweralkoxy, N(R21)2
- wherein R21 is hydrogen,. loweralkyl, or
- wherein W is as above, or
- R2 is hydrogen or loweralkyl;
- R3 is hydrogen, loweralkyl or
- wherein R6 is as above or NHR27 wherein R27 is loweralkyl;
- R35 is
- wherein R36 is loweralkyl;
- R4 is
- wherein R7 is hydrogen or loweralkyl, C(R25)2OR8 wherein R8 is hydrogen, loweralkyl, or
- wherein R6 is as above and R25 is hydrogen or loweralkyl;
- R1 and R8 taken together with the oxygen to which they are attached from a group of the formula
- wherein R9 and R10 are independently hydrogen or loweralkyl;
- the optical isomers thereof, or the pharmaceutically acceptable salts thereof.
A method of inhibiting bacterial or fungal growth in a mammal in need of bacterial or fungal growth inhibition which comprises administering to such a mammal a bacterial or fungal growth inhibiting effective amount of a compound of the formula
- RCH(OR1)CH(NR2R3)R4 or RCH2CR35(NR2R3)R4
- wherein R is
- wherein R5 is CH3(CH2)mCΞC, CH3(CH2)mCH═CH, CH3(CH2)mCH2CH2,
- wherein m is 3 to 15, n is 0 to 12, and W and X are independently hydrogen, hydroxy, loweralkyl, loweralkoxy, halogen, or trifluoromethyl, or
- wherein R23 is loweralkyl;
- R1 is hydrogen, loweralkyl, Si(R23)2C(R23), wherein R23 is loweralkyl,
- wherein R24 is loweralkyl or
- wherein R6 is hydrogen, loweralkyl, loweralkoxy, N(R21)2
- wherein R21 is hydrogen, loweralkyl, or
- wherein W is as above, or
- R2 is hydrogen or loweralkyl;
- R3 is hydrogen, loweralkyl or
- wherein R6 is as above or NHR27 wherein R27 is loweralkyl;
- R35 is
- wherein R36 is loweralkyl;
- R4 is
- wherein R7 is hydrogen or loweralkyl C(R25)2OR8 wherein R8 is hydrogen, loweralkyl, or
- wherein R6 is as above and R25 is hydrogen or loweralkyl;
- R1 and R8 taken together with the oxygen to which they are attached form a group of the formula
- wherein R9 and R10 are dependently hydrogen or loweralkyl;
- R2, R3 and R4 taken together with the nitrogen and oxygen to which they are attached form a group of the formula
- wherein W is as above;
- R2 and R3 taken together with the nitrogen atom to which it is attached form a group of the formula
- wherein W is as above;
- R3 and R4 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula
- wherein R2 is as above and R25 is loweralkyl;
- R1, R2 and R3 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula
- wherein R26is loweralkyl;
- the optical isomers thereof, or the pharmaceutically acceptable salts thereof.
A method of inhibiting bacterial or fungal growth in a mammal in need of bacterial or fungal growth inhibition which comprises administering to such a mammal a bacterial or fungal growth inhibiting effective amount of a compound of the formula
- RCH(OR1)CH(NR2R3)R4 or RCH2CR35(NR2R3)R4
- wherein R is
- wherein R5 is CH3(CH2)mCΞC, CH3(CH2)mCH═CH, CH3(CH2)mCH2CH2,
- wherein m is 3 to 15, n is 0 to 12, and W and X are independently hydrogen, hydroxy, loweralkyl, loweralkoxy, halogen, or trifluoromethyl, or
- wherein R23 is loweralkyl;
- Z is S, O or C═O;
- and A is S or O;
- R1 is hydrogen, loweralkyl,
- wherein R24 is loweralkyl or
- wherein R6 is hydrogen, loweralkyl, loweralkoxy, N(R21)2
- wherein R21 is hydrogen, loweralkyl. or
- wherein W is as above, or
- R2 is hydrogen or loweralkyl;
- R3 is hydrogen, loweralkyl or
- wherein R6 is as above or NHR27 wherein R27 is loweralkyl;
- R35 is
- wherein R36 is loweralkyl;
- R4 is
- wherein R7 is hydrogen or loweralkyl, C(R25)2OR8 wherein R8 is hydrogen, loweralkyl, or
- wherein R6 is as above and R25 is hydrogen or loweralkyl;
- R1 and R8 taken together with the oxygen to which they are attached form a group of the formula
A method of inhibiting bacterial or fungal growth in a mammal in need of bacterial or fungal growth inhibition which comprises administering to such a mammal a bacterial or fungal growth inhibiting effective amount of a compound of the formula
- RCH(OR1)CH(NR2R3)R4 or RCH2CR35(NR2R3)3
- wherein R is
- wherein R5 is CH3(CH2)mCΞC, CH3(CH2)mCH═CH, CH3(CH2)mCH2CH2,
- wherein m is 3 to 15, n is 0 to 12, and W and X are independently hydrogen, hydroxy, loweralkyl, loweralkoxy, halogen, or trifluoromethyl, or
- wherein R23 is loweralkyl;
- R1 is hydrogen, loweralkyl, Si(R23)2C(R23)3 wherein R23 is loweralkyl,
- wherein R24 is loweralkyl or
- wherein R6 is hydrogen, loweralkyl, loweralkoxy, N(R21)2
- wherein R21 is hydrogen, loweralkyl, or
- wherein W is as above, or
- R2 is hydrogen or loweralkyl;
- R3 is hydrogen, loweralkyl or
- wherein R6 is as above or NHR27 wherein R27 is loweralkyl;
- R35 is
- wherein R36 is loweralkyl;
- R4 is
- wherein R7is hydrogen or loweralkyl, C(R25)2OR8 wherein R8 is hydrogen, loweralkyl, or
- wherein R6is as above and R25 is hydrogen or loweralkyl;
- R1 and R8 taken together with the oxygen to which they are attached form a group of the formula
- wherein R9 and R10 are independently hydrogen or loweralkyl;
- R2, R3 and R4 taken together with the nitrogen and oxygen to which they arc attached form a group of the formula
- wherein W is as above;
- R2and R3 taken together with the nitrogen atom to which it is attached form a group of the formula
- wherein W is as above;
- R3 and R4 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula
- wherein R2 is as above and R25 is loweralkyl;
- R1, R2 and R3 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula
- wherein R26 is loweralkyl;
- the optical isomers thereof, or the pharmaceutically acceptable salts thereof.
A method of inhibiting bacterial or fungal growth in a mammal in need of bacterial or fungal growth inhibition which comprises administering to such a mammal a bacterial or fungal growth inhibiting effective amount of a compound of the formula
- RCH(OR1)CH(NR2R3)R4 or RCH2CR35(NR2R3)R4
- wherein R is
- wherein R5 is CH3(CH2)mCΞC, CH3(CH2)mCH═CH, CH3(CH2)mCH2CH2,
- wherein m is 3 to 15, n is 3 to 12, and W and X are independently hydrogen, hydroxy, loweralkyl, loweralkoxy, halogen, or trifluoromethyl, or
- wherein R23 is loweralkyl;
- R1 is hydrogen, loweralkyl,
- wherein R24 is loweralkyl or
- wherein R6 is hydrogen, loweralkyl, loweralkoxy, N(R21)2
- wherein R21 is hydrogen, loweralkyl, or
- wherein W is as above, or
- R2 is hydrogen or loweralkyl, R3 is hydrogen, loweralkyl or
- wherein R6 is as above or NHR27 wherein R27 is loweralkyl, R35 is
- wherein R36 is loweralkyl;
- R4 is
- wherein R7 is hydrogen or loweralkyl, C(R25)2OR8 wherein R8 is hydrogen, loweralkyl, or
- wherein R6 is as above and R25 is hydrogen or loweralkyl;
- R40 is loweralkyl or a group of the formula
- wherein W is as above;
- R1 and R8 taken together with the oxygen to which they are attached form a group of the formula
- wherein R9 and R10 are independently hydrogen or loweralkyl;
- R2 and R3 taken together with the nitrogen atom to which it is attached form a group of the formula
- wherein W is as above, R1, R2 and R3 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula
- wherein R26 is loweralkyl;
- the optical isomers thereof, or the pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.