Back to results
US 5,977,147 AGranted
1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino- 1,3-propanediols and related compounds
AssigneeHoechst Marion Roussel, Inc.
InventorsJohn Joseph Tegeler, Barbara Seavey Rauckman, Russell Richard Lee Hamer, Brian Scott Freed, Gregory Harold Merriman
Life of this patent
Estimating the term…
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 treating leukemia, sarcoma, carcinoma, or glioma in a mammal comprising administering to a mammal in need of leukemia, sarcoma, carcinoma, or glioma treatment a leukemia, sarcoma, carcinoma, or glioma treating effective amount of a compound of the formula
- RCH(OR.sup.1)CH(NR.sup.2 R.sup.3)R.sup.4 or RCH.sub.2 CR.sup.35 (NR.sup.2 R.sup.3)R.sup.4
- wherein R is ##STR62## wherein R.sup.5 is CH.sub.3 (CH.sub.2).sub.m C.tbd.C, CH.sub.3 (CH.sub.2).sub.m CH.dbd.CH CH.sub.3 (CH.sub.3)(CH.sub.2).sub.m CH.sub.2 CH.sub.2, ##STR63## 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 ##STR64## wherein R.sup.23 is loweralkyl;
- R.sup.1 is hydrogen, loweralkyl, ##STR65## wherein R.sup.24 is loweralkyl or ##STR66## wherein R.sup.6 is hydrogen, loweralkyl, loweralkoxy, N(R.sup.21).sub.2 wherein R.sup.21 is hydrogen, loweralkyl, or ##STR67## wherein W is as above, or ##STR68## R.sup.2 is hydrogen or loweralkyl;
- R.sup.3 is hydrogen, loweralkyl or ##STR69## wherein R.sup.6 is as above or NHR.sup.27 wherein R.sup.27 is loweralkyl;
- R.sup.35 is ##STR70## wherein R.sup.36 is loweralkyl;
- R.sup.4 is ##STR71## wherein R.sup.7 is hydrogen or loweralkyl, C(R.sup.25).sub.2 OR.sup.8 wherein R.sup.8 is hydrogen, loweralkyl, or ##STR72## wherein R.sup.6 is as above and R.sup.25 is hydrogen or loweralkyl;
- R.sup.1 and R.sup.8 taken together with the oxygen to which they are attached form a group of the formula ##STR73## wherein R.sup.9 and R.sup.10 are independently hydrogen or loweralkyl;
- the optical isomers thereof, or the pharmaceutically acceptable salts thereof.
5 more elements
A method of treating leukemia, sarcoma, carcinoma, or glioma in a mammal comprising administering to a mammal in need of leukemia, sarcoma, carcinoma, or glioma treatment a leukemia, sarcoma, carcinoma, or glioma treating effective amount of a compound of the formula
- RCH(OR.sup.1)CH(NR.sup.2 R.sup.3)R.sup.4 or RCH.sub.2 CR.sup.35 (NR.sup.2 R.sup.3)R.sup.4
- wherein R is ##STR74## wherein R.sup.5 is CH.sub.3 (CH.sub.2).sub.m C.tbd.C, CH.sub.3 (CH.sub.2).sub.m CH.dbd.CH, CH.sub.3 (CH.sub.2).sub.m CH.sub.2 CH.sub.2, ##STR75## 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 ##STR76## wherein R.sup.23 is loweralkyl;
- R.sup.1 is hydrogen, loweralkyl, Si(R.sup.23).sub.2 C(R.sup.23), wherein R.sup.23 is loweralkyl ##STR77## wherein R.sup.24 is loweralkyl or ##STR78## wherein R.sup.6 is hydrogen, loweralkyl, loweralkoxy, N(R.sup.21).sub.2 wherein R.sup.21 is hydrogen, loweralkyl, or ##STR79## wherein W is as above, or ##STR80## R.sup.2 is hydrogen or loweralkyl;
- R.sup.3 is hydrogen, loweralkyl or ##STR81## wherein R.sup.6 is as above or NHR.sup.27 wherein R.sup.27 is loweralkyl;
- R.sup.35 is ##STR82## wherein R.sup.36 is loweralkyl;
- R.sup.4 is ##STR83## wherein R.sup.7 is hydrogen or loweralkyl, C(R.sup.25).sub.2 OR.sup.8 wherein R.sup.8 is hydrogen, loweralkyl, or ##STR84## wherein R.sup.6 is as above and R.sup.25 is hydrogen or loweralkyl;
- R.sup.1 and R.sup.8 taken together with the oxygen to which they are attached form a group of the formula ##STR85## wherein R.sup.9 and R.sup.10 are independently hydrogen or loweralkyl;
- R.sup.2, R.sup.3 and R.sup.4 taken together with the nitrogen and oxygen to which they are attached form a group of the formula ##STR86## wherein W is as above;
- R.sup.2 and R.sup.3 taken together with the nitrogen atom to which it is attached form a group of the formula ##STR87## wherein W is as above;
- R.sup.3 and R.sup.4 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula ##STR88## wherein R.sup.2 is as above and R.sup.25 is loweralkyl;
- R.sup.1, R.sup.2 and R.sup.3 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula ##STR89## wherein R.sup.26 is loweralkyl;
- the optical isomers thereof, or the pharmaceutically acceptable salts thereof.
9 more elements
A method of treating leukemia, sarcoma, carcinoma, or glioma in a mammal comprising administering to a mammal in need of leukemia, sarcoma, carcinoma, or glioma treatment a leukemia, sarcoma, carcinoma, or glioma treating effective amount of a compound of the formula
- RCH(OR.sup.1)CH(NR.sup.2 R.sup.3)R.sup.4 or RCH.sub.2 CR.sup.35 (NR.sup.2 R.sup.3)R.sup.4
- wherein R is ##STR90## wherein R.sup.5 is CH.sub.3 (CH.sub.2).sub.m C.tbd.C, CH.sub.3 (CH.sub.2).sub.m CH.dbd.CH, CH.sub.3 (CH.sub.2).sub.m CH.sub.2 CH.sub.2, ##STR91## 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 ##STR92## wherein R.sup.23 is loweralkyl;
- Z is S, O or C.dbd.O;
- and A is S or O;
- R.sup.1 is hydrogen, loweralkyl, ##STR93## wherein R.sup.24 is loweralkyl or ##STR94## wherein R.sup.6 is hydrogen, loweralkyl, loweralkoxy, N(R.sup.21).sub.2 wherein R.sup.21 is hydrogen, loweralkyl, or ##STR95## wherein W is as above, or ##STR96## R.sup.2 is hydrogen or loweralkyl;
- R.sup.3 is hydrogen, loweralkyl or ##STR97## wherein R.sup.6 is as above or NHR27 wherein R.sup.27 is loweralkyl;
- R.sup.35 is ##STR98## wherein R.sup.36 is loweralkyl;
- R.sup.4 is ##STR99## wherein R.sup.7 is hydrogen or loweralkyl, C(R.sup.25).sub.2 OR.sup.8 wherein R.sup.8 is hydrogen, loweralkyl, or ##STR100## wherein R.sup.6 is as above and R.sup.25 is hydrogen or loweralkyl;
- R.sup.1 and R.sup.8 taken together with the oxygen to which they are attached forrn a group of the formula ##STR101##
6 more elements
A method of treating leukemia, sarcoma, carcinoma, or glioma in a mammal comprising administering to a mammal in need of leukemia, sarcoma, carcinoma, or glioma treatment a leukemia, sarcoma, carcinoma, or glioma treating effective amount of a compound of the formula
- RCH(OR.sup.1)CH(NR.sup.2 R.sup.3)R.sup.4 or RCH.sub.2 CR.sup.35 (NR.sup.2 R.sup.3)R.sup.3
- wherein R is ##STR102## wherein R.sup.5 is CH.sub.3 (CH.sub.2).sub.m C.tbd.C, CH.sub.3 (CH.sub.2).sub.m CH.dbd.CH, CH.sub.3 (CH.sub.2).sub.m CH.sub.2 CH.sub.2, ##STR103## 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 ##STR104## wherein R.sup.23 is loweralkyl;
- R.sup.1 is hydrogen, loweralkyl, Si(R.sup.23).sub.2 C(R.sup.23).sub.3 wherein R.sup.23 is loweralkyl, ##STR105## wherein R.sup.24 is loweralkyl or ##STR106## wherein R.sup.6 is hydrogen, loweralkyl, loweralkoxy, N(R.sup.21).sub.2 wherein R.sup.21 is hydrogen, loweralkyl, or ##STR107## wherein W is as above, or ##STR108## R.sup.2 is hydrogen or loweralkyl;
- R.sup.3 is hydrogen, loweralkyl or ##STR109## wherein R.sup.6 is as above or NHR.sup.27 wherein R.sup.27 is loweralkyl;
- R.sup.35 is ##STR110## wherein R.sup.36 is loweralkyl;
- R.sup.4 is ##STR111## wherein R.sup.7 is hydrogen or loweralkyl, C(R.sup.25).sub.2 OR.sup.8 wherein R.sup.8 is hydrogen, loweralkyl, or ##STR112## wherein R.sup.6 is as above and R.sup.25 is hydrogen or loweralkyl;
- R.sup.1 and R.sup.8 taken together with the oxygen to which they are attached form a group of the formula ##STR113## wherein R.sup.9 and R.sup.10 are independently hydrogen or loweralkyl;
- R.sup.2, R.sup.3 and R.sup.4 taken together with the nitrogen and oxygen to which they arc attached form a group of the formula ##STR114## wherein W is as above;
- R.sup.2 and R.sup.3 taken together with the nitrogen atom to which it is attached form a group of the formula ##STR115## wherein W is as above;
- R.sup.3 and R.sup.4 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula ##STR116## wherein R.sup.2 is as above and R.sup.25 is loweralkyl;
- R.sup.1, R.sup.2 and R.sup.3 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula ##STR117## wherein R.sup.26 is loweralkyl;
- the optical isomers thereof, or the pharmaceutically acceptable salts thereof.
9 more elements
A method of treating leukemia, sarcoma, carcinoma, or glioma in a mammal comprising administering to a mammal in need of leukemia, sarcoma, carcinoma, or glioma treatment a leukemia, sarcoma, carcinoma, or glioma treating effective amount of a compound of the formula
- RCH(OR.sup.1)CH(NR.sup.2 R.sup.3)R.sup.4 or RCH.sub.2 CR.sup.35 (NR.sup.2 R.sup.3)R.sup.4
- wherein R is ##STR118## wherein R.sup.5 is CH.sub.3 (CH.sub.2).sub.m C.tbd.C, CH.sub.3 (CH.sub.2).sub.m CH.dbd.CH, CH.sub.3 (CH.sub.2).sub.m CH.sub.2 CH.sub.2, ##STR119## 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 ##STR120## wherein R.sup.23 is loweralkyl;
- R.sup.1 is hydrogen, loweralkyl, ##STR121## wherein R.sup.24 is loweralkyl or ##STR122## wherein R.sup.6 is hydrogen, loweralkyl, loweralkoxy, N(R.sup.21).sub.2 wherein R.sup.21 is hydrogen, loweralkyl, or ##STR123## wherein W is as above, or ##STR124## R.sup.2 is hydrogen or loweralkyl, R.sup.3 is hydrogen, loweralkyl or ##STR125## wherein R.sup.6 is as above or NHR.sup.27 wherein R.sup.27 is loweralkyl, R.sup.35 is ##STR126## wherein R.sup.36 is loweralkyl;
- R.sup.4 is ##STR127## wherein R.sup.7 is hydrogen or loweraklyl, C(R.sup.25).sub.2 OR.sup.8 wherein R.sup.8 is hydrogen, loweralkyl, or ##STR128## wherein R.sup.6 is as above and R.sup.25 is hydrogen or loweralkyl;
- R.sup.40 is loweralkyl or a group of the formula ##STR129## wherein W is as above;
- R.sup.1 and R.sup.8 taken together with the oxygen to which they are attached form a group of the formula ##STR130## wherein R.sup.9 and R.sup.10 are independently hydrogen or loweralkyl;
- R.sup.2 and R.sup.3 taken together with the nitrogen atom to which it is attached form a group of the formula ##STR131## wherein W is as above, R.sup.1, R.sup.2 and R.sup.3 taken together with the nitrogen and oxygen atoms to which they are attached form a group of the formula ##STR132## wherein R.sup.26 is loweralkyl;
- the optical isomers thereof, or the pharmaceutically acceptable salts thereof.
5 more elements
Dependencies are inferred from the claim text.