WO2014167575A2 - Composition stable de tigécycline - Google Patents
Composition stable de tigécycline Download PDFInfo
- Publication number
- WO2014167575A2 WO2014167575A2 PCT/IN2014/000186 IN2014000186W WO2014167575A2 WO 2014167575 A2 WO2014167575 A2 WO 2014167575A2 IN 2014000186 W IN2014000186 W IN 2014000186W WO 2014167575 A2 WO2014167575 A2 WO 2014167575A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tigecycline
- pharmaceutical composition
- maltose
- stable pharmaceutical
- solution
- Prior art date
Links
- 229960004089 tigecycline Drugs 0.000 title claims abstract description 68
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- FPZLLRFZJZRHSY-HJYUBDRYSA-N tigecycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O FPZLLRFZJZRHSY-HJYUBDRYSA-N 0.000 title claims abstract description 13
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims abstract description 41
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims abstract description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 37
- 239000000243 solution Substances 0.000 claims abstract description 30
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims abstract description 27
- 239000008364 bulk solution Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 238000004108 freeze drying Methods 0.000 claims description 6
- 238000011049 filling Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 238000011068 loading method Methods 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- SOVUOXKZCCAWOJ-HJYUBDRYSA-N (4s,4as,5ar,12ar)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O SOVUOXKZCCAWOJ-HJYUBDRYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000008215 water for injection Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 6
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 229960001375 lactose Drugs 0.000 description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000006345 epimerization reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229960001021 lactose monohydrate Drugs 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 229940009662 edetate Drugs 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000005414 inactive ingredient Substances 0.000 description 2
- 238000012792 lyophilization process Methods 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 201000001178 Bacterial Pneumonia Diseases 0.000 description 1
- 208000036209 Intraabdominal Infections Diseases 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000006652 catabolic pathway Effects 0.000 description 1
- 239000008380 degradant Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 229960005219 gentisic acid Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940061267 tygacil Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
Definitions
- the present invention relates to a stable pharmaceutical composition comprising Tigecycline and maltose. Further the present invention discloses process for the preparation of the said composition.
- Tigecycline is a tetracycline derivative (a glycylcycline) which is a chemically (4S,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7bis(dimethylamino)- I.,4,4a,5,5a,6, 11,12a-octahydro-3, 10,12,12a-tetrahydroxy- 1,11 -dioxo-2- naphthacenecarboxamide.
- Molecular formula of Tigecycline is C29H39N5OS a
- USRE40I83 discloses 7-substituted-9-substituted amino-6-demethyl-6- deoxytetracyclines which cover Tigecycline.
- Tigecycline is marketed as lyophilized powder for reconstitution for intravenous infusion under trade name TYGACIL® by Wyeth; which contains Tigecycline as active ingredient and lactose monohydrate as inactive ingredient.
- Tigecycline is approved for complicated skin and skin structure infections, complicated intra-abdominal infections and community-acquired bacterial pneumonia.
- Tigecycline is currently marked as TYGAC!L® by Wyeth; which contains lactose monohydrate as inactive ingredient.
- the pH of the composition after reconstitution is acidic.
- the composition uses lactose monohydrate as stabilizer to control the degradation of Tigecycline by epimerization pathways.
- US7879828 discloses a composition comprising tigecycline, lactose, and an acid •selected from hydrochloric acid and gentisic acid, and the pH of the composition in a solution is between about 3.0 and about 7.0. Focus of US7879828 is to use lactose and lower pH to get stable composition of Tigecycline.
- US7705168 discloses a manufacturing process for the production of tigecycline as a reconstitutable powder having less than 0.9% total degradants comprising the steps of reducing and maintaining the oxygen level in water for injection to less than or equal to 0.5 ppm. Focus of US7705I68 is to control oxidation0 pathway by controlling oxygen level.
- US2009275660 discloses stable parenteral formulations of tigecycline and process of preparation thereof, wherein the formulation comprises of an edetate, a pH modifying agent or an antioxidant, such that the formulation remains stable5 for at least 45 hours. Focus of US2009275660 is to provide stable composition by using edetate.
- US2010035845 discloses a frozen pharmaceutical formulation suitable for administration to a subject parenteraily, comprising a therapeutically effective0 amount of tigecycline and an agent selected from the group consisting of lactose, dextrose, glucose, mannose, sucrose, ribose, xylose and a combination thereof. Focus of US201 0035845 is to use lactose, dextrose, glucose, mannose, sucrose, ribose, xylose to get stable composition of Tigecycl ine.
- the present invention relates to a stable pharmaceutical composition
- a stable pharmaceutical composition comprisi ng Tigecycl ine and maltose.
- Another object of the present invention is to provide process for the preparation of a stable pharmaceutical composition comprising Tigecycl ine and maltose.
- Another object of the present invention is to provide a stable pharmaceutical composition
- a stable pharmaceutical composition comprising Tigecycl ine and maltose wherei n the pH of the composition after reconstitution is in between 3 - 6 preferably between 4 - 5 and more preferably between 4.3 - 4.9.
- Another object of the present invention is to provide a stable pharmaceutical composition comprising Tigecycl ine and maltose wherein the composition is prepared from bulk solution comprises Tigecycl ine from 1 5 - 50 mg/mL, maltose from 30 - 1 00 mg/mL and pH of the bu lk solution is in between 3 - 6, preferably between 4 - 5 and more preferably between 4.3 - 4.9.
- Another object of the present invention is to provide process for preparation of a stable pharmaceutical composition comprising Tigecycl ine and maltose wherein the pH o f the composition after reconstitution is in between 3 - 6 preferably between 4 - 5 and more preferably between 4.3 - 4.9.
- Another object of the present invention is to disclose use of maltose as stabilizing agent for preparation of stable Tigecycline composition.
- Present invention provides a stable pharmaceutical composition comprising Tigecycline and maltose. Further the invention provides a use of maltose as stabilizing agent for preparation of stable Tigecycline composition. In another embodiment the present invention provides a process for preparation of stable pharmaceutical composition comprising Tigecycline and maltose. In one another embodiment the present invention also provides a stable pharmaceutical composition comprising Tigecycline and maltose wherein the pH of the composition after reconstitution is in between 3-6.
- Present invention provides a stable pharmaceutical composition comprising Tigecycline and maltose and a process for the preparation of the said composition.
- the stable pharmaceutical composition comprises Tigecyciine and maltose; wherein the composition is prepared from bulk solution comprises Tigecycline from 15 - 50 mg/mL. maltose from 30 - 100 mg/mL and pH of the bulk solution is in between 3-6.
- a stable pharmaceutical composition is defined as a lyophilized composition comprising Tigecycline and maltose; wherein impurity 4-epimer of Tigecycline, is less than 3% throughout shelf life.
- 4-epimer of Tigecycline is having following structure:
- the stable pharmaceutical composition of the present invention is analyzed by HPLC method.
- the method of analysis by HPLC is well known in the art.
- a bulk solution is defined as a solution comprising Tigecycline and maltose, which is further lyophilized to obtain a stable pharmaceutical composition according to the present invention.
- the pH of the bulk solution is in between 3 - 6, wherein pH is attained by addition of pH adjusting agents like NaOH or HCI.
- Lyophilization also known as freeze drying, is a process in which solvent is removed from a bulk solution after it is frozen and placed under a vacuum, allowing the solvent to change directly from solid to gaseous phase without passing through a liquid phase. Lyophilization process is well known to the person skilled in the art.
- desired dissolved oxygen (DO) level refers to low amount of dissolved oxygen in solvent, preferably in the range of 0.5 ppm to 2 ppm.
- the present invention provides a process for the preparation of a stable pharmaceutical composition comprising Tigecycline and maltose comprising step of:
- step I 1. Taking WFI in manufacturing tank, sparging inert gas until desired dissolved oxygen level is attained. 2. Adding Maltose and Tigecycline to the solution of step I. in any order and adjusting pH of the solution in between 3 - 6.
- a process for preparation of a stable pharmaceutical composition comprising step of adding maltose and Tigecycline to the water for injection (WFI) in any order and adjusting pfl of the solution in between 3 -6.
- a process for preparation of a stable pharmaceutical composition comprising a step of adding maltose and Tigecycline to the water for injection (WFI) in any order; wherein Hydrochloric acid is added prior to the addition Tigecycline.
- WFI water for injection
- the present invention provides a process for the preparation of a stable pharmaceutical composition comprising Tigecycline and ' maltose comprising step of:
- step 2 2. Adding Maltose to the solution of step 1 and stir.
- the present invention provides a stable pharmaceutical composition comprising Tigecycline and maltose wherein the pH of the composition after reconstitution is in between 3-6 preferably between 4-5 and more preferably between 4.3 - 4.9 and process for preparation of the same.
- the present invention discloses use of maltose as stabilizing agent for preparation of stable Tigecycline composition.
- Example 1 Composition of Tigecycline bulk solution:
- step 2 2. Adding Maltose and Tigecycline to the solution of step 1 in any order.
- Example 2 Composition of Tigecycline bulk solution:
- pH of the bulk / reconstituted solution is approx.4.7.
- step II 2. Adding Maltose to the solution of step I and stir.
- Lyophilized product obtained according to example 1 and 2 comprises of Tigecycline and maltose; wherein the pH of the composition after reconstitution is in between 3-6.
- Stability study The stability study of the composition obtained by example 2 was carried out at 25°C and 60% RH, 40°C and 75% RH and 50°C for 1 month. The results obtained in the stability study are given below:
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
La présente invention concerne une composition pharmaceutique stable de Tigécycline et un procédé de préparation de celle-ci. La composition comprend de la Tigécycline et du maltose, le pH de la solution principale ou de la solution après reconstitution se situant entre 3 et 6.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI201431458T SI2978426T1 (sl) | 2013-03-26 | 2014-03-25 | Stabilni sestavek tigeciklina |
| PL14782395T PL2978426T3 (pl) | 2013-03-26 | 2014-03-25 | Stabilna kompozycja tygecykliny |
| CA2905645A CA2905645C (fr) | 2013-03-26 | 2014-03-25 | Composition stable de tigecycline |
| EP14782395.9A EP2978426B1 (fr) | 2013-03-26 | 2014-03-25 | Composition stable de tigécycline |
| ES14782395T ES2766832T3 (es) | 2013-03-26 | 2014-03-25 | Composición estable de tigeciclina |
| US14/779,889 US9511145B2 (en) | 2013-03-26 | 2014-03-25 | Stable tigecycline composition |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1127/MUM/2013 | 2013-03-26 | ||
| INMU11272013 | 2013-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2014167575A2 true WO2014167575A2 (fr) | 2014-10-16 |
| WO2014167575A3 WO2014167575A3 (fr) | 2014-12-24 |
Family
ID=51690086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2014/000186 WO2014167575A2 (fr) | 2013-03-26 | 2014-03-25 | Composition stable de tigécycline |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2014167575A2 (fr) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090275660A1 (en) | 2008-05-01 | 2009-11-05 | Chauhan Bhaskar | Stable parenteral formulations of tigecycline |
| US20100035845A1 (en) | 2008-08-06 | 2010-02-11 | Wyeth | Tigecycline formulations |
| US7705168B2 (en) | 2005-06-16 | 2010-04-27 | Wyeth Llc | Manufacturing process for tigecycline |
| US7879828B2 (en) | 2005-03-14 | 2011-02-01 | Wyeth Llc | Tigecycline compositions and methods of preparation |
| WO2011143503A2 (fr) | 2010-05-12 | 2011-11-17 | Rempex Pharmaceuticals, Inc. | Compositions de tétracycline |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009285632A1 (en) * | 2008-08-28 | 2010-03-04 | Astrazeneca Ab | Compositions and methods of treatment comprising ceftaroline |
-
2014
- 2014-03-25 WO PCT/IN2014/000186 patent/WO2014167575A2/fr active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7879828B2 (en) | 2005-03-14 | 2011-02-01 | Wyeth Llc | Tigecycline compositions and methods of preparation |
| US7705168B2 (en) | 2005-06-16 | 2010-04-27 | Wyeth Llc | Manufacturing process for tigecycline |
| US20090275660A1 (en) | 2008-05-01 | 2009-11-05 | Chauhan Bhaskar | Stable parenteral formulations of tigecycline |
| US20100035845A1 (en) | 2008-08-06 | 2010-02-11 | Wyeth | Tigecycline formulations |
| WO2011143503A2 (fr) | 2010-05-12 | 2011-11-17 | Rempex Pharmaceuticals, Inc. | Compositions de tétracycline |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP2978426A4 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014167575A3 (fr) | 2014-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101354093B1 (ko) | 티게사이클린 조성물 및 이의 제조방법 | |
| JP6182262B2 (ja) | 抗がん剤を含む安定な水溶性医薬組成物 | |
| US10253031B2 (en) | Stable pemetrexed arginine salt and compositions comprising it | |
| US20190105392A1 (en) | Caspofungin Acetate Formulations | |
| US9446091B2 (en) | Caspofungin or salts thereof with high purity, as well as preparation method and use thereof | |
| EP3037431A1 (fr) | Dérivé de vancomycine et procédé de préparation et application correspondants | |
| EP3058958B1 (fr) | Composition d'anidulafungine | |
| US20170196899A1 (en) | Stable pharmaceutical compositions | |
| EP2978426A2 (fr) | Composition stable de tigécycline | |
| WO2014167575A2 (fr) | Composition stable de tigécycline | |
| WO2017185030A1 (fr) | Formulation de caspofungine à faible taux d'impuretés | |
| KR20110111494A (ko) | 티게사이클린의 단리방법 | |
| US20140323443A1 (en) | Tigecycline formulations | |
| WO2017118994A1 (fr) | Composition parentérale lyophilisée de tigécycline et procédé de préparation associé | |
| WO2014191552A1 (fr) | Procédé de stabilisation de tigecycline | |
| WO2014032956A1 (fr) | Formulations de tigécycline | |
| WO2023173615A1 (fr) | Solution aqueuse médicamenteuse à base d'ester de peptide stable | |
| AU2014241481A1 (en) | Hydrochloride salts of an antibiotic compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENP | Entry into the national phase in: |
Ref document number: 2905645 Country of ref document: CA |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 14779889 Country of ref document: US |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 2014782395 Country of ref document: EP |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14782395 Country of ref document: EP Kind code of ref document: A2 |