1. A method for manipulating one or more data entries from a group of data entries in a user interface, the method comprising:
a computer displaying a first subset of data entries from the group of data entries within a display window of the user interface, wherein the group of data entries contains more data entries than can fit within the display window;
the computer determining that a second subset of data entries from the group of data entries will not fit within the display window of the user interface concurrently with the first subset of data entries;
responsive to determining that the second subset of data entries will not fit within the display window of the user interface concurrently with the first subset of data entries, the computer generating and displaying a marker representative of the second subset of data entries, wherein the marker is displayed within the display window of the user interface with the first subset of data entries; and
the computer manipulating the data entries in the second subset of data entries based on an operation request directed at the marker representative of the second subset of data entries.
2. The method of claim 1, wherein the second subset of data entries contains one or more data entries from the group of entries not included in the first subset of data entries.
3. The method of claim 1, wherein the second subset of data entries contains all data entries, from the group of data entries, not included in the first subset of data entries.
4. The method of claim 1, wherein the marker representative of the second subset of data entries is a line of text.
5. The method of claim 1, wherein the marker representative of the second subset of data entries of a graphical icon.
6. The method of claim 1, further comprising the computer manipulating the data entries in the first subset of data entries based on the operation request directed at the marker representative of the second subset of data entries.
7. The method of claim 1, wherein the step of the computer manipulating the data entries of the second subset comprises one or more of: the computer altering the data entries, the computer editing the data entries, the computer moving the data entries, the computer organizing the data entries, the computer using the data entries in a subsequent operation, the computer using respective fields within the data entries in a subsequent operation, and the computer using the data entries to determine a response to a query where the operation request directed at the marker is the query.
8. The method of claim 1, further comprising the computer determining that the operation request is directed at the marker by the computer receiving a selection of the marker from a user and the computer subsequently receiving the operation request from the user.
9. A computer program product for manipulating one or more data entries from a group of data entries in a user interface, the computer program product comprising:
one or more computer-readable tangible storage devices and program instructions, for execution by one or more computer processors and stored on at least one of the one or more storage devices, the program instructions comprising:
program instructions to display a first subset of data entries from the group of data entries within a display window of the user interface, wherein the group of data entries contains more data entries than can fit within the display window;
program instructions to determine that a second subset of data entries from the group of data entries will not fit within the display window of the user interface concurrently with the first subset of data entries;
program instructions to, responsive to determining that the second subset of data entries will not fit within the display window of the user interface concurrently with the first subset of data entries, generate and display a marker representative of the second subset of data entries, wherein the marker is displayed within the display window of the user interface with the first subset of data entries; and
program instructions to manipulate the data entries in the second subset of data entries based on an operation request directed at the marker representative of the second subset of data entries.
10. The computer program product of claim 9, wherein the second subset of data entries contains one or more data entries from the group of data entries not included in the first subset of data entries.
11. The computer program product of claim 9, wherein the second subset of data entries contains all data entries, from the group of data entries, not included in the first subset of data entries.
12. The computer program product of claim 9, wherein the marker representative of the second subset of data entries is a line of text.
13. The computer program product of claim 9, wherein the marker representative of the second subset of data entries of a graphical icon.
14. The computer program product of claim 9, further comprising program instructions, for execution by one or more computer processors and stored on at least one of the one or more storage devices, to manipulate the data entries in the first subset of data entries based on the operation request directed at the marker representative of the second subset of data entries.
15. The computer program product of claim 9, wherein the program instructions to manipulate the data entries of the second subset comprises one or more of: program instructions to alter the data entries, program instructions to edit the data entries, program instructions to move the data entries, program instructions to organize the data entries, program instructions to use the data entries in a subsequent operation, program instructions to use respective fields within the data entries in a subsequent operation, and program instructions to use the data entries to determine a response to a query where the operation request directed at the marker is the query.
16. The computer program product of claim 9, further comprising program instructions, for execution by one or more computer processors and stored on at least one of the one or more storage devices, to:
receive a selection of the marker from a user;
receive the operation request from the user; and
determine that the operation request is directed at the marker by receiving the selection of the marker from the user and subsequently receiving the operation request from the user.
17. A computer system for manipulating one or more data entries from a group of data entries in a user interface, the computer system comprising:
one or more processors, one or more computer-readable memories, one or more computer-readable tangible storage devices and program instructions which are stored on the one or more storage devices for execution by the one or more processors via the one or more memories, the program instructions comprising:
program instructions to display a first subset of data entries from the group of data entries within a display window of the user interface, wherein the group of data entries contains more data entries than can fit within the display window;
program instructions to determine that a second subset of data entries from the group of data entries will not fit within the display window of the user interface concurrently with the first subset of data entries;
program instructions to, responsive to determining that the second subset of data entries will not fit within the display window of the user interface concurrently with the first subset of data entries, generate and display a marker representative of the second subset of data entries, wherein the marker is displayed within the display window of the user interface with the first subset of data entries; and
program instructions to manipulate the data entries in the second subset of data entries based on an operation request directed at the marker representative of the second subset of data entries.
18. The computer system of claim 17, wherein the second subset of data entries contains one or more data entries from the group of data entries not included in the first subset of data entries.
19. The computer system of claim 17, wherein the second subset of data entries contains all data entries, from the group of data entries, not included in the first subset of data entries.
20. The computer system of claim 17, wherein the marker representative of the second subset of data entries is a line of text.
21. The computer system of claim 17, wherein the marker representative of the second subset of data entries of a graphical icon.
22. The computer system of claim 17, further comprising program instructions, stored on at least one of the one or more storage devices for execution by at least one of the one or more processors via at least one of the one or more memories, to manipulate the data entries in the first subset of data entries based on the operation request directed at the marker representative of the second subset of data entries.
23. The computer system of claim 17, wherein the program instructions to manipulate the data entries of the second subset comprises one or more of: program instructions to alter the data entries, program instructions to edit the data entries, program instructions to move the data entries, program instructions to organize the data entries, program instructions to use the data entries in a subsequent operation, program instructions to use respective fields within the data entries in a subsequent operation, and program instructions to use the data entries to determine a response to a query where the operation request directed at the marker is the query.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A process for the preparation of compound of formula (I) (Telithromycin) or its pharmaceutically acceptable salts
where, R is
the process comprising the steps of
(a) reacting compound of formula (IX)
with carbonyldiimidazole in presence of a polar solvent and base to obtain the compound of formula (X)
where R1 and R2 are same or different protecting groups represented by
Rb is C1 to C10 alkyl group or aryl group, preferably Rb is C1-C4 alkyl group, aryl represents substituted or unsubstituted phenyl group; more preferably R1 and R2 are same or different selected from acetyl, benzyl or benzoyl group
(b) condensing the compounds of formula (X) with R\u2014NH2 in a suitable polar solvent to obtain compounds of formula (XI)
where R is as defined above and R1 and R2 are same or different protecting groups as described above;
(c) treating the obtained compound formula (XI) with an acid to give the compound of formula (XII)
(d) oxidizing the resulting compounds of formula (XII) in presence of oxidizing agent to formula (XIII)
(e) removing the protecting group at 2\u2032 position of formula (XIII) by treating with an alcohol to give Telithromycin of Formula (I)
2. A process for the preparation of compounds of formula (I) or its pharmaceutically acceptable salts
where, R is
the process comprising the steps of
(a) reacting compound of formula (IX)
with carbonyldiimidazole in presence of a polar solvent and base to obtain the compound of formula (X),
where R1 and R2 are same or different protecting groups represented by
Rb is C1 to C10 alkyl group or aryl group, preferably Rb is C1-C4 alkyl group, aryl represents substituted or unsubstituted phenyl group, more preferably R1 and R2 are same or different selected from acetyl, benzyl or benzoyl group;
(b) condensing the compounds of formula (X) with R\u2014NH2 in a suitable polar solvent to obtain compounds of formula (XI)
where R is as defined above and R1 and R2 are same or different protecting groups as described above;
(c) treating the obtained compound formula (XI) with an acid to give compound of formula (XII)
(d) treating compounds of formula (XII) with an alcohol to give compounds of formula (XIV)
(e) oxidizing the resulting compounds of formula (XIV) of step (d) selectively in presence of oxidizing agent to obtain Telithromycin formula (I).
3. A process as claimed in claim 1, wherein said polar solvent in step (a) is selected from dimethylformamide, tetrahydrofuran, acetonitrile and mixtures thereof.
4. A process as claimed in claim 1, wherein said base in step (a) is selected from DBU, triethylamine, diisopropylethylamine.
5. A process as claimed in claim 1, wherein said polar solvent in step (b) is selected from group comprising of methanol, ethanol, isopropanol, n-propanol, n-butanol, iso butyl alcohol, tert-butyl alcohol, methoxyethanol, ethoxyethanol, pentanol, neo-pentyl alcohol, tert-pentyl alcohol, cyclohexanol, ethylene glycol, propylene glycol, benzyl alcohol, phenol, glycerol, dimethylformamide (DMF), dimethylacetamide (DMAC), 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), 1,3-dimethyl-2-imidazolidinone (DMI), N-methylpyrrolidinone (NMP), formamide, N-methylacetamide, N-methylformamide, acetonitrile, dimethylsulfoxide, propionitrile, ethyl formate, methyl acetate, hexachloroacetone, HMPA, HMPT, acetone, ethyl methyl ketone, ethyl acetate, isopropyl acetate, t-butyl acetate, sulfolane, N,N-dimethylpropionamide, nitromethane, nitrobenzene, tetrahydrofuran (THF), dioxane, water, polyethers or mixtures thereof.
6. A process as claimed in claim 5, wherein said polar solvent is selected from dimethylformamide or acetonitrile.
7. A process as claimed in claim 1, wherein said step (b) is carried out in presence or absence of base selected from DBU, triethylamine, diisopropylethylamine
8. A process as claimed in claim 1, wherein said step (b) is carried out at a temperature 5\xb0 C. to 120\xb0 C.
9. A process as claimed in claim 8, wherein the said step (b) is carried out preferably at a temperature 30\xb0 C. to 60\xb0 C.
10. A process as claimed in claim 1, wherein the said acid in step (c) is selected from organic or inorganic acid.
11. A process as claimed in claim 10, wherein the said acid is selected from the group comprising of hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid or hydrofluoric acid.
12. A process as claimed in claim 11, wherein the acid is preferably hydrochloric acid.
13. A process as claimed in claim 1, wherein step (c) is carried out in a solvent selected from water, polar organic solvents or mixtures thereof.
14. A process as claimed in claim 13, wherein said solvent is selected from water, alcohol or mixtures thereof.
15. A process as claimed in claim 14, wherein said solvent is selected from water, methanol, ethanol, isopropanol, n-propanol, tert-butanol, n-butanol or mixtures thereof.
16. A process as claimed in claim 1, wherein said step (c) is carried out at a temperature 0\xb0 C. to 70\xb0 C.
17. A process as claimed in claim 16, where in step (c) is carried out at a temperature 20\xb0 C. to 60\xb0 C.
18. A process as claimed in claim 1, wherein oxidation said in step (d) is carried out using Corey-Kim oxidation method, Dess-Martin reagent, Pfitzner Moffat method or modifications thereof or with dimethyl sulfoxide in presence of oxalyl chloride or phosphorous pentoxide or p-Toluene sulfonyl chloride or acetic anhydride or N-chlorosuccinimide or by manganese or chromium or selenium reagents, tert-amine oxides or any said oxidant in presence or absence of phase transfer catalyst.
19. A process as claimed in claim 1, wherein alcohol said in step (e) is selected from group comprising of methanol, ethanol, n-propanol, iso propanol, tert-butanol, n-butanol or mixtures thereof.
20. A process as claimed in claim 19, wherein the said alcohol is preferably methanol.
21. A process as claimed in claim 1, wherein said step (e) is carried out in presence or absence of mineral acid selected from HCl, H2SO4
22. A process as claimed in claim 1, wherein said step (e) is carried out at a temperature of 0\xb0 C. to 100\xb0 C.
23. A process as claimed in claim 22, wherein step (e) is carried out preferably at a temperature of 20\xb0 C. to 70\xb0 C.
24. A process as claimed in claim 2, wherein said alcohol in step (d) is selected from group comprising of methanol, ethanol, n-propanol, iso propanol, tert-butanol, n-butanol or mixtures thereof.
25. A process as claimed in claim 24, wherein said alcohol is preferably methanol.
26. A process as claimed in claim 2, wherein said step (d) is carried out at a temperature of 0 to 70\xb0 C.
27. A process as claimed in claim 26, wherein the temperature is between 20 to 65\xb0 C.
28. A process as claimed in claim 2, wherein said oxidation in step (e) is carried out using Corey-Kim oxidation method, Des-Martins reagent, Pfitzner moffat method or modifications thereof or with dimethyl sulfoxide in presence of oxalyl chloride or phosphorous pentoxide or p-Toluene sulfonyl chloride or acetic anhydride.
29. A process as claimed in claim 2, wherein oxidation in step (e) is carried out by manganese or chromium or selenium reagents, tert-amine oxides or any above oxidant in presence of phase transfer catalyst.
30. The novel compounds
(i) 10,11-Anhydro-2\u2032,4\u2033-di-O-benzoyl-12-O-imidazolylcarbonyl-6-O-methylerythromycin A of formula (Xa)
(ii) 2\u2032,4\u2033-di-O-benzoyl-11-amino-11-N-4-4-(3-pyridyl)imidazol-1-ylbutyl-11-deoxy-6-O-methylerythromycin A 11,12-cyclic carbamate of formula (XIa)
(iii) 2\u2032-O-benzoyl-11-amino-11-N-4-4-(3-pyridyl)imidazol-1-ylbutyl-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate of formula (XIIa)
(iv) 2\u2032-benzoyl-11-amino-11-N-4-4-(3-pyridyl)imidazol-1-ylbutyl-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate of formula (XIIa)
where R is
31. A process for the preparation of compound of formula (XIIIa)
where, R is
the process comprising the steps of
(a\u2032) reacting 2\u2032,4\u2033-di-O-benzoyl-6-O-methylerythromycin A compound of formula (IXa)
with carbonyldiimidazole in presence of a polar solvent and base to obtain 10,11-anhydro-2\u2032,4\u2033-di-O-benzoyl-12-O-imidazolylcarbonyl-6-O-methylerythromycin A (Xa)
(b\u2032) condensing the compounds of formula (Xa) with R\u2014NH2 in a suitable polar solvent in presence of base to obtain 2\u2032,4\u2033-di-O-benzoyl-11-amino-11-N-4-4-(3-pyridyl)imidazol-1-ylbutyl-11-deoxy-6-O-methylerythromycin A 11,12-cyclic carbamate of formula (XIa)
where R is as defined above
(c\u2032) treating the obtained compound formula (XIa) with an acid to give 2\u2032-O-benzoyl-11-amino-11-N-4-4-(3-pyridyl)imidazol-1-ylbutyl-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate of formula (XIIa)
(d\u2032) oxidizing the resulting compounds of formula (XIIa) in presence of oxidizing agent to obtain the compound of formula (XIIIa)
32. A process as claimed in claim 31, wherein said polar solvent in step (a\u2032) is selected from dimethylformamide, tetrahydrofuran, acetonitrile and mixtures thereof.
33. A process as claimed in claim 31, wherein said base in step (a)\u2032 is selected from DBU, triethylamine, diisopropylethylamine.
34. A process as claimed in claim 31, wherein said polar solvent in step (b\u2032) is selected from group comprising of methanol, ethanol, isopropanol, n-propanol, n-butanol, iso butyl alcohol, tert-butyl alcohol, methoxyethanol, ethoxyethanol, pentanol, neo-pentyl alcohol, tert-pentyl alcohol, cyclohexanol, ethylene glycol, propylene glycol, benzyl alcohol, phenol, glycerol, dimethylformamide (DMF), dimethylacetamide (DMAC), 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), 1,3-dimethyl-2-imidazolidinone (DMI), N-methylpyrrolidinone (NMP), formamide, N-methylacetamide, N-methylformamide, acetonitrile, dimethylsulfoxide, propionitrile, ethyl formate, methyl acetate, hexachloroacetone, HMPA, HMPT, acetone, ethyl methyl ketone, ethyl acetate, isopropyl acetate, t-butyl acetate, sulfolane, N,N-dimethylpropionamide, nitromethane, nitrobenzene, tetrahydrofuran (THF), dioxane, water, polyethers or mixtures thereof.
35. A process as claimed in claim 31, wherein said polar solvent is selected from dimethylformamide or acetonitrile.
36. A process as claimed in claim 31, wherein base said in step (b\u2032) is selected from DBU, triethylamine, diisopropylethylamine.
37. A process as claimed in claim 31, wherein the said step (b\u2032) is carried out preferably at a temperature 30\xb0 C. to 60\xb0 C.
38. A process as claimed in claim 31, wherein the said acid in step (c\u2032) is selected from organic or inorganic acid selected from the group comprising of hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid or hydrofluoric acid.
39. A process as claimed in claim 31, wherein step (c\u2032) is carried out in a solvent selected from water, methanol, ethanol, isopropanol, n-propanol, tert-butanol, n-butanol or mixtures thereof.
40. A process as claimed in claim 31, where in step (c\u2032) is carried out at a temperature 20\xb0 C. to 60\xb0 C.
41. A process as claimed in claim 31, wherein oxidation said in step (d\u2032) is carried out using Corey-Kim oxidation method, Dess-Martin reagent, Pfitzner Moffat method or modifications thereof or with dimethyl sulfoxide in presence of oxalyl chloride or phosphorous pentoxide or p-Toluene sulfonyl chloride or acetic anhydride or N-chlorosuccinimide by manganese or chromium or selenium reagents, tert-amine oxides or any said oxidant in presence of phase transfer catalyst.
42. Use of compounds of formula (Xa), (XIa), (XIIa), (XIIIa) for the preparation of Telithromycin (I)