# US 2014/0155607 A1 · Novel Salts of Raltegravir > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0155607 A1 - Document ID: US20140155607A1 - Status: Published application - Kind: A1 - Application number: 14/009,178 - Filed: 2012-04-04 - Published: 2014-06-05 - Earliest claimed: 2011-04-06 - Assignees: Lupin Limited - Inventors: Purna Chandra Ray; Ashok Sopanrao Yadav; Dnyaneshwar Tukaram Singare; Surinder Kumar Arora; Girij Pal Singh - Web page: https://patentgrep.com/patent/US20140155607A1 ## CPC - C07D 413/12: linked by a chain containing hetero atoms as chain links - A61K 31/513: having oxo groups directly attached to the heterocyclic ring, e.g. cytosine - A61P 31/12: Antivirals - C07C 211/04: Mono-, di- or tri-methylamine - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The present invention provides novel salts of raltegravir, viz., meglumine salt, erbumine salt, ammonium salt, tris salt and L-arginine salt of raltegravir and processes for their preparation. ## Claims ### Claim 1 Meglumine salt of raltegravir. ### Claim 2 A crystalline meglumine salt of raltegravir, represented by formula I, which is characterized by XRPD (X-ray powder diffractogram) comprising of peaks expressed as 2θ at 7.9, 8.2, 8.9, 12.4, 13.4, 14.9, 15.9, 17.2, 19.4, 21.5, 21.9, 22.4, 22.8, 25.0, 26.3 and 27.1±0.2 degrees. ### Claim 3 (depends on 2) A process for preparation of crystalline meglumine salt of raltegravir of claim 2, which comprises of treating raltegravir with meglumine in an alcohol solvent followed by addition of an anti-solvent to precipitate the meglumine salt. ### Claim 4 (depends on 3) A process according to claim 3, wherein the alcohol solvent is selected from methanol, ethanol, n-propanol and isopropanol. ### Claim 5 (depends on 4) A process according claim 4, wherein the alcohol solvent is methanol. ### Claim 6 (depends on 3) A process according to claim 3, wherein the anti-solvent is selected from ethers such diethyl ether, diisopropyl ether, ethyl methyl ether, diethyl ether; cyclic ethers such as tetrahydrofuran and dioxane. ### Claim 7 (depends on 6) A process according to claim 6, wherein the anti-solvent is diisopropyl ether. ### Claim 8 (depends on 3) A process according to claim 3, wherein the molar ratio of meglumine with respect to raltegravir is in the range of 1 to 3. ### Claim 9 Erbumine salt of raltegravir. ### Claim 10 A crystalline erbumine salt of raltegravir, represented by formula II, which is characterized by XRPD (X-ray powder diffractogram) comprising of peaks expressed as 2θ at 4.2, 8.4, 9.1, 11.7, 12.6, 13.8, 15.2, 16.9, 18.0, 18.4, 18.8, 19.0, 20.8, 21.2, 22.0, 22.4 and 22.7±0.2 degrees. ### Claim 11 (depends on 10) A process for preparation of crystalline erbumine salt of raltegravir of claim 10, which comprises of treating raltegravir with tert-butyl amine in an alcohol. ### Claim 12 (depends on 11) A process according to claim 11, wherein the alcohol is selected from methanol, ethanol, n-propanol and isopropanol. ### Claim 13 (depends on 12) A process according to claim 12, wherein the alcohol is methanol. ### Claim 14 (depends on 11) A process according to claim 11, wherein the molar ratio of tertiary butyl amine with respect to raltegravir is in the range of 1 to 3. ### Claim 15 Ammonium salt of raltegravir. ### Claim 16 A crystalline ammonium salt of raltegravir, represented by formula III, which is characterized by XRPD (X-ray powder diffractogram) comprising of peaks expressed as 2θ at 6.0, 8.8, 9.9, 11.3, 12.4, 16.2, 17.2, 17.7, 18.7, 19.4, 20.0, 20.8, 21.6, 24.6, 25.4, 26.4±0.2 degrees. ### Claim 17 (depends on 16) A process for preparation of crystalline ammonium salt of raltegravir of claim 16, which comprises of treating raltegravir with ammonia in an alcohol solvent. ### Claim 18 (depends on 17) A process according to claim 17, wherein the alcohol is selected from methanol, ethanol, n-propanol and isopropanol. ### Claim 19 (depends on 18) A process according to claim 18, wherein the alcohol is methanol. ### Claim 20 (depends on 17) A process according to claim 17, wherein ammonia is employed in gaseous form or in the form of alcoholic solution. ### Claim 21 Tris salt of raltegravir. ### Claim 22 A crystalline tris salt of raltegravir, represented by formula IV, which is characterized by XRPD (X-ray powder diffractogram) which comprises of peaks expressed as 2θ at 7.6, 7.9, 8.1, 11.3, 11.6, 13.4, 14.9, 15.4, 15.8, 15.9, 16.2, 20.0, 22.4, 22.8, 23.3, 23.8, 25.0, 25.3, 26.5, 27.0, 29.2, 29.9, 32.3±0.2 degrees. ### Claim 23 (depends on 22) A process for preparation of crystalline tris salt of raltegravir of claim 22, which comprises of treating raltegravir with tris(hydroxymethyl)aminomethane in an alcohol solvent. ### Claim 24 (depends on 23) A process according to claim 23, wherein the alcohol is selected from methanol, ethanol, n-propanol, and isopropanol. ### Claim 25 (depends on 24) A process according to claim 24, wherein the alcohol is methanol. ### Claim 26 (depends on 23) A process according to claim 23, wherein the molar ratio of tris(hydroxymethyl)aminomethane with respect to raltegravir is in the range of 1 to 3. ### Claim 27 L-arginine salt of raltegravir. ### Claim 28 An amorphous L-arginine salt of raltegravir, represented by formula V, which is characterized by XRPD (X-ray powder diffractogram) which comprises of a single broad peak expressed as 2θ at about 20.2±0.2 degrees. ### Claim 29 (depends on 28) A process for preparation of amorphous L-arginine salt of raltegravir of claim 28, which comprises of treating raltegravir with L-arginine in an alcohol solvent followed by addition of anti-solvent. ### Claim 30 (depends on 29) A process according to claim 29, wherein the alcohol is selected from methanol, ethanol, n-propanol and isopropanol. ### Claim 31 (depends on 30) A process according to claim 30, wherein the alcohol is methanol. ### Claim 32 (depends on 29) A process according to claim 29, wherein the anti-solvent is selected from ethers such as diethyl ether, diisopropyl ether, ethyl methyl ether, diethyl ether; cyclic ethers such as tetrahydrofuran and dioxane, ### Claim 33 (depends on 32) A process according to claim 32, wherein the anti-solvent is diisopropyl ether. ### Claim 34 (depends on 29) A process according to claim 29, wherein the molar ratio of L-arginine with respect to raltegravir is in the range of 1 to 3.