Claims
- 1. A compound of the formula ##STR97## wherein R.sub.1, which can be singly or multiply substituted in any position of the pyridine ring not already substituted by R.sub.2, is selected from the group consisting of hydrogen, alkyl and substituted alkyl wherein the alkyl portion is from 1 to 8 carbon atoms, inclusive, and isomeric forms thereof, cycloalkyl and substituted cycloalkyl, of from 3 to 8 carbon atoms, inclusive substituted oxygen, substituted nitrogen, halogen, phenyl, and substituted phenyl, --(CH.sub.2).sub.n --OH, --(CH.sub.2).sub.n --NR.sub.4 R.sub.5, and branched chain isomers thereof wherein n is an integer of from 1 to 8, inclusive, R.sub.4 and R.sub.5 are H or alkyl of from 1 to 8 carbon atoms, inclusive, and isomeric forms thereof; wherein R.sub.2, which can be singly substituted in any position of the pyridine ring not already substituted by R.sub.1, is ##STR98## and X is the amino function of a compound selected from the group 7(R)-hydroxy-methyl 1-thio-.alpha.-lincosaminide, 7(S)-hydroxy-methyl 1-thio-.alpha.-lincosaminide, 7(S)-halo-methyl 1-thio-.alpha.-lincosaminide, 7(R)-halo-methyl 1-thio-.alpha.-lincosaminide, 7(S)-methoxy-methyl 1-thio-.alpha.-lincosaminide, 7-deoxy-7(S)-(methylthio)-methyl 1-thio-.alpha.-lincosaminide, 7-deoxy-7(S)-(2-hydroxyethylthio)-methyl 1-thio-.alpha.-lincosaminide and 7-deoxy-7(S)-(3-hydroxypropylthio)-methyl 1-thio-.alpha.-lincosaminide; and the pharmaceutically acceptable acid-addition salts thereof.
- 2. A compound of the formula ##STR99## wherein R.sub.1 and R.sub.2, which can be in the 2, 3, 4, 5, 6, 7, 8, or 9 position of the ring, are as defined in claim 1; wherein R.sub.3 is selected from the group consisting of H, CH.sub.3, C.sub.2 H.sub.5, and --CH.sub.2 --CH.sub.2 --OH; wherein n is an integer of from 1 to 4, inclusive; and the pharmaceutically acceptable acid-addition salts thereof.
- 3. A compound, according to claim 1, wherein R.sub.1 is in the 4 position and is alkyl of from 1 to 8 carbon atoms, inclusive, and isomeric forms thereof; wherein R.sub.2 is in the 2 or 3 position; and the pharmaceutically acceptable acid addition salts thereof.
- 4. A compound, according to claim 2, wherein R.sub.1 is in the 4 position and is alkyl of from 1 to 8 carbon atoms, inclusive, and isomeric forms thereof; and the pharmaceutically acceptable acid-addition salts thereof.
- 5. A compound of the formula, according to claim 1, ##STR100## wherein R.sub.1, which can be singly or multiply substituted in the 3, 4, 5, or 6 position of the pyridine ring, is selected from the group consisting of hydrogen, alkyl and substituted alkyl wherein the alkyl portion is from 1 to 8 carbon atoms, inclusive, and branched chain isomers thereof cycloalkyl and substituted cycloalkyl, of from 3 to 8 carbon atoms, inclusive substituted oxygen, substituted nitrogen, halogen, phenyl, and substituted phenyl, --(CH.sub.2).sub.n --OH, --(CH.sub.2).sub.n --NR.sub.4 R.sub.5, and isomeric forms thereof, wherein n is an integer of from 1 to 8, inclusive, R.sub.4 and R.sub.5 are H or alkyl of from 1 to 8 carbon atoms, inclusive, and isomeric forms thereof; wherein Y is selected from the group consisting of 7(R)-hydroxy, 7(S)-hydroxy, 7(S)-halo, 7(R)-halo, 7(S)-methoxy, 7(S)-(methylthio), 7(S)-(2-hydroxyethylthio), and, 7(S)-(3-hydroxypropylthio); and the pharmaceutically acceptable acid-addition salts thereof.
- 6. A compound of the formula, according to claim 2, ##STR101## wherein R.sub.1, which can be singly or multiply substituted in the 3, 4, 5, 7, 8 or 9 position of the ring, is selected from the group consisting of hydrogen, alkyl and substituted alkyl wherein the alkyl portion is from 1 to 8 carbon atoms, inclusive, and branch chain isomers thereof cycloalkyl and substituted cycloalkyl, of from 3 to 8 carbon atoms, inclusive substituted oxygen, substituted nitrogen, halogen, phenyl, and substituted phenyl, --(CH.sub.2).sub.n --OH, --(CH.sub.2).sub.n --NR.sub.4 R.sub.5, and branched chain isomers thereof, wherein n is an integer of from 1 to 8, inclusive, R.sub.4 and R.sub.5 are H or alkyl of from 1 to 8 carbon atoms, inclusive, and branched chain isomers thereof; wherein R.sub.3 is selected from the group consisting of H, CH.sub.3, C.sub.2 H.sub.5, and --CH.sub.2 --CH.sub.2 --OH; wherein n is an integer of from 1 to 4, inclusive, wherein Y is selected from the group consisting of 7(R)-hydroxy, 7(S)-hydroxy, 7(S)-halo, 7(R)-halo, 7(S)-methoxy, 7(S)-(methylthio), 7(S)-(2-hydroxyethylthio), and 7(S)-(3-hydroxypropylthio); and the pharmaceutically acceptable acid-addition salts thereof.
- 7. A compound, according to claim 5, wherein Y is selected from the group consisting of 7(R)-hydroxy and 7(S)-halo.
- 8. A compound, according to claim 6, wherein Y is selected from the group consisting of 7(R)-hydroxy and 7(S)-halo.
- 9. A compound, according to claim 7, wherein 7(S)-halo is 7(S)-chloro.
- 10. A compound, according to claim 8, wherein 7(S)-halo is 7(S)-chloro.
- 11. A compound, according to claim 5, wherein Y is 7(S)-halo and R is alkyl of from 1 to 8 carbon atoms, inclusive, and isomeric forms thereof.
- 12. A compound, according to claim 6, wherein Y is 7(S)-halo; wherein R.sub.1 is alkyl of from 1 to 8 carbon atoms, inclusive, and isomeric forms thereof, and R.sub.3 is hydrogen.
- 13. A compound, according to claim 12, wherein Y is 7(S)-halo; wherein R.sub.1 is C.sub.2 H.sub.5 ; and wherein R.sub.3 is hydrogen.
- 14. A compound according to claim 12, wherein Y is 7(S)-halo; wherein R.sub.1 is C.sub.4 H.sub.9 ; and wherein R.sub.3 is hydrogen.
- 15. A compound, according to claim 11, wherein 7(S)-halo is 7(S)-chloro.
- 16. A compound, according to claim 12, wherein 7(S)-halo is 7(S)-chloro.
- 17. A compound, according to claim 13, wherein 7(S)-halo is 7(S)-chloro.
- 18. A compound, according to claim 14, wherein 7(S)-halo is 7(S)-chloro.
- 19. A compound of the formula: ##STR102## and the pharmaceutically acceptable acid-addition salts thereof.
- 20. A compound of the formula ##STR103## and the pharmaceutically acceptable acid-addition salts thereof.
- 21. A compound, according to claim 5, wherein R.sub.1 is hydrogen, and Y is 7(S)-halo.
- 22. A compound, according to claim 1, wherein R.sub.1 is hydrogen, and R.sub.2, which is in the 3 position, is ##STR104## wherein X is 7(S)-halo-methyl 1-thio-.alpha.-lincosaminide.
- 23. A compound, according to claim 1, wherein R.sub.1 is hydrogen, and R.sub.2, which is in the 4 position, is ##STR105## wherein X is 7(S)-halo-methyl 1-thio-.alpha.-lincosaminide.
- 24. A compound, according to claim 6, wherein R.sub.1 and R.sub.3 are hydrogen, and Y is 7(S)-halo.
- 25. A compound, according to claim 6, wherein R.sub.1 is hydrogen, R.sub.3 is CH.sub.3, and Y is 7(S)-halo.
- 26. A compound, according to claim 5, wherein R.sub.1, which is in the 5 position, is ethyl, and Y is 7(S)-halo.
- 27. A compound, according to claim 5, wherein R.sub.1, which is in the 4 position, is ethyl, and Y is 7(S)-halo.
- 28. A compound, according to claim 6, wherein R.sub.1, which is in the 5 position, is ethyl, R.sub.3 is methyl, and Y is 7(S)-halo.
- 29. A compound, according to claim 6, wherein R.sub.1, which is in the 5 position, is ethyl, R.sub.3 is H, and Y is 7(S)-halo.
- 30. A compound, according to claim 6, wherein R.sub.1 is H, R.sub.3 is --CH.sub.2 --CH.sub.2 --OH, and Y is 7(S)-halo.
- 31. A compound, according to claim 1, wherein R.sub.1, which is in the 2 position, is chloro, and R.sub.2, which is in the 3 position, is ##STR106## wherein X is 7(S)-halo-methyl 1-thio-.alpha.-lincosaminide.
- 32. A compound, according to claim 21, wherein Y is 7(S)-chloro.
- 33. A compound, according to claim 22, wherein R.sub.2 is ##STR107## wherein X is 7(S)-chloro-methyl 1-thio-.alpha.-lincosaminide.
- 34. A compound, according to claim 23, wherein R.sub.2 is ##STR108## wherein X is 7(S)-chloro-methyl 1-thio-.alpha.-lincosaminide.
- 35. A compound, according to claim 24, wherein Y is 7(S)-chloro.
- 36. A compound, according to claim 25, wherein Y is 7(S)-chloro.
- 37. A compound, according to claim 26, wherein Y is 7(S)-chloro.
- 38. A compound, according to claim 27, wherein Y is 7(S)-chloro.
- 39. A compound, according to claim 28, wherein Y is 7(S)-chloro.
- 40. A compound, according to claim 29, wherein Y is 7(S)-chloro.
- 41. A compound, according to claim 30, wherein Y is 7(S)-chloro.
- 42. A compound, according to claim 31, wherein R.sub.2 is ##STR109## wherein X is 7(S)-chloro-methyl 1-thio-.alpha.-lincosaminide.
- 43. A compound, according to claim 5, wherein R.sub.1 is hydrogen, and Y is 7(R)-hydroxy.
- 44. A compound, according to claim 5, wherein R.sub.1, which is in the 4 position, is ethyl, and Y is 7(R)-hydroxy.
- 45. A compound, according to claim 6, wherein R.sub.1 and R.sub.3 are hydrogen, and Y is 7(R)-hydroxy.
- 46. A compound, according to claim 5, wherein R.sub.1 is hydrogen, and Y is 7(S)-hydroxy.
- 47. A compound, according to claim 5, wherein R.sub.1, which is in the 4 position, is ethyl, and Y is 7(S)-hydroxy.
- 48. A compound, according to claim 6, wherein R.sub.1 and R.sub.3 are hydrogen, and Y is 7(S)-hydroxy.
- 49. A compound, according to claim 6, wherein R.sub.1, which is in the 4 position, is ethyl, R.sub.3 is hydrogen, and Y is 7(S)-hydroxy.
- 50. A compound, according to claim 5, wherein R.sub.1 is hydrogen, and Y is 7(R)-halo.
- 51. A compound, according to claim 5, wherein R.sub.1, which is in the 4 position, is ethyl, and Y is 7(R)-halo.
- 52. A compound, according to claim 6, wherein R.sub.1 and R.sub.3 are hydrogen, and Y is 7(R)-halo.
- 53. A compound, according to claim 6, wherein R.sub.1, which is in the 4 position, is ethyl, R.sub.3 is hydrogen, and Y is 7(R)-halo.
- 54. A compound, according to claim 5, wherein R.sub.1, which is in the 5 position, is butyl, and Y is 7(S)-halo.
- 55. A compound, according to claim 50, wherein Y is 7(R)-chloro.
- 56. A compound, according to claim 51, wherein Y is 7(R)-chloro.
- 57. A compound, according to claim 52, wherein Y is 7(R)-chloro.
- 58. A compound, according to claim 53, wherein Y is 7(R)-chloro.
- 59. A compound, according to claim 54, wherein Y is 7(S)-chloro.
- 60. A compound of the formula ##STR110## wherein X is selected from the group consisting of 7(R)-hydroxy-methyl 1-thio-.alpha.-lincosaminide, 7(S)-hydroxy-methyl 1-thio-.alpha.-lincosaminide, 7(S)-halo-methyl 1-thio-.alpha.-lincosaminide, 7(R)-halo-methyl 1-thio-.alpha.-lincosaminide, 7(S)-methoxy-methyl 1-thio-.alpha.-lincosaminide, 7-deoxy-7(S)-(methylthio)-methyl 1-thio-.alpha.-lincosaminide, 7-deoxy-7(S)-(2-hydroxyethylthio)-methyl 1-thio-.alpha.-lincosaminide, and 7-deoxy-7(S)-(3-hydroxypropylthio)-methyl 1-thio-.alpha.-lincosaminide, and the pharmaceutically acceptable acid-addition salts thereof.
- 61. A compound, according to claim 60, wherein halo is chloro.
- 62. A compound of the formula ##STR111## wherein X is as defined in claim 60, and the pharmaceutically acceptable acid-addition salts thereof.
- 63. A compound, according to claim 62, wherein halo is chloro.
- 64. A compound of the formula ##STR112## wherein X is as defined in claim 60, and the pharmaceutically acceptable acid-addition salts thereof.
- 65. A compound, according to claim 64, wherein halo is chloro.
- 66. The 2-palmitate of the compounds defined in claim 1.
- 67. The 2-phosphate of the compounds defined in claim 1.
- 68. The 2-palmitate of the compounds defined in claim 2.
- 69. The 2-phosphate of the compounds defined in claim 2.
- 70. The 2-palmitate of the compounds defined in claim 60.
- 71. The 2-phosphate of the compounds defined in claim 60.
- 72. The 2-palmitate of the compounds defined in claim 62.
- 73. The 2-phosphate of the compounds defined in claim 62.
- 74. The 2-palmitate of the compounds defined in claim 64.
- 75. The 2-phosphate of the compounds defined in claim 64.
- 76. A therapeutic composition for treating humans and animals hosting a disease-causing microparasite selected from the group consisting of bacteria, coccidia, and mycoplasma comprising, in unit dosage form, from about 15 to about 500 mg. of a compound of the formula ##STR113## wherein R.sub.1, which can be singly or multiply substituted in any position of the pyridine ring not already substituted by R.sub.2, is selected from the group consisting of hydrogen, alkyl and substituted alkyl wherein the alkyl portion is from 1 to 8 carbon atoms, inclusive, and branched chain isomers thereof, cycloalkyl and substituted cycloalkyl, of from 3 to 8 carbon atoms, inclusive substituted oxygen, substituted nitrogen, halogen, phenyl, and substituted phenyl, --(CH.sub.2).sub.n --OH, --(CH.sub.2).sub.n --NR.sub.4 R.sub.5, and branched chain isomers thereof, wherein n is an integer of from 1 to 8, inclusive, R.sub.4 and R.sub.5 are H or alkyl of from 1 to 8 carbon atoms, inclusive, and branched chain isomers thereof; wherein R.sub.2, which can be singly substituted in any position of the pyridine ring not already substituted by R.sub.1, is ##STR114## and X is the amine function of a sugar amine compound selected from the group consisting of 7(R)-hydroxy-methyl 1-thio-.alpha.-lincosaminide, 7(S)-hydroxy-methyl 1-thio-.alpha.-lincosaminide, 7(S)-halo-methyl 1-thio-.alpha.-lincosaminide, 7(R)-halo-methyl 1-thio-.alpha.-lincosaminide, 7(S)-methoxy-methyl 1-thio-.alpha.-lincosaminide, 7-deoxy-7(S)-(methylthio)-methyl 1-thio-.alpha.-lincosaminide, 7-deoxy-7(S)-(2-hydroxyethylthio)-methyl 1-thio-.alpha.-lincosaminide and 7-deoxy-7(S)-(3-hydroxypropylthio)-methyl 1-thio-.alpha.-lincosaminide; or the pharmaceutically acceptable acid addition salts thereof as an essential active ingredient in combination with a pharmaceutical carrier.
- 77. The composition of claim 76 suitable for parenteral administration wherein said pharmaceutical carrier is a sterile vehicle and said compound is present in a concentration of from about 5% to about 65% weight volume of the composition.
- 78. A therapeutic composition for treating humans and animals hosting a disease-causing microparasite selected from the group consisting of bacteria, coccidia, and mycoplasma comprising, in unit dosage form, from about 15 to about 500 mg. of a compound of the formula: ##STR115## wherein R.sub.1 and R.sub.2 are as defined in claim 1; wherein R.sub.3 is selected from the group consisting of H, CH.sub.3, C.sub.2 H.sub.5, and --CH.sub.2 --CH.sub.2 --OH; wherein n is an integer of from 1 to 4, inclusive; or the pharmaceutically acceptable acid addition salts thereof as an essential active ingredient in combination with a pharmaceutical carrier.
- 79. The composition of claim 78 suitable for parenteral administration wherein said pharmaceutical carrier is a sterile vehicle and said compound is present in a concentration of from about 5% to about 65% weight volume of the composition.
- 80. The composition of claim 78 wherein said compound has the following formula: ##STR116##
- 81. The composition of claim 78 wherein said compound has the following formula: ##STR117##
DESCRIPTION
This is a continuation-in-part of my pending application Ser. No. 096,652, filed on Nov. 23, 1979 now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3086912 |
Bergy et al. |
Apr 1963 |
|
3496163 |
Birkenmeyer et al. |
Feb 1970 |
|
3758454 |
Argoudelis et al. |
Sep 1973 |
|
Non-Patent Literature Citations (1)
Entry |
Noller, "Chem. of Organic Compounds", 3rd Ed., W. B. Saunders Co., Phila, Pa., 1965, pp. 661 and 666. |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
96652 |
Nov 1979 |
|