HRP20200755T1 - Postupak kristalizacije za dobivanje kristala kanagliflozin hemihidrata - Google Patents
Postupak kristalizacije za dobivanje kristala kanagliflozin hemihidrata Download PDFInfo
- Publication number
- HRP20200755T1 HRP20200755T1 HRP20200755TT HRP20200755T HRP20200755T1 HR P20200755 T1 HRP20200755 T1 HR P20200755T1 HR P20200755T T HRP20200755T T HR P20200755TT HR P20200755 T HRP20200755 T HR P20200755T HR P20200755 T1 HRP20200755 T1 HR P20200755T1
- Authority
- HR
- Croatia
- Prior art keywords
- canagliflozin
- temperature
- crystallization
- amount
- liter
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 12
- 229960001713 canagliflozin Drugs 0.000 title claims 10
- VHOFTEAWFCUTOS-TUGBYPPCSA-N canagliflozin hydrate Chemical compound O.CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=C(F)C=C1.CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=C(F)C=C1 VHOFTEAWFCUTOS-TUGBYPPCSA-N 0.000 title claims 10
- 238000002425 crystallisation Methods 0.000 title claims 9
- 230000008025 crystallization Effects 0.000 title claims 9
- 239000013078 crystal Substances 0.000 title claims 8
- 239000002904 solvent Substances 0.000 claims 4
- 239000000725 suspension Substances 0.000 claims 4
- 238000001816 cooling Methods 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 238000010951 particle size reduction Methods 0.000 claims 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000007873 sieving Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
Claims (11)
1. Postupak za pripravu kristala kanagliflozin hemihidrata naznačen time što sadrži uzastopne korake
a) pripremanje otopine u posudi za kristalizaciju kanagliflozina u sustavu otapala koji sadrži vodu u količini od 0,37 mas.% do 1,50 mas.% u uvjetima koncentracije i temperature koji omogućuju potpuno otapanje kanagliflozina;
b) hlađenje navedene otopine do takve temperature da kristalizacija započne dodavanjem zametka kristala;
c) sijanje otopine iz koraka b) s kristalnim kanagliflozin hemihidratom;
d) hlađenje otopine iz koraka c) na temperaturu u rasponu od 35°C do 47°C kako bi se dobila kristalna suspenzija;
e) uklanjanje dijela kristalne suspenzije iz posude za kristalizaciju u količini manjoj od cjelokupnog sadržaja i podvrgavanje navedenog dijela smanjenju veličine čestica, zagrijavanje navedenog dijela na temperaturu veću od temperature kristalne suspenzije u posudi za kristalizaciju, te vraćanje navedenog dijela u posudu za kristalizaciju;
f) ponavljanje koraka e) sve dok cjelokupni sadržaj kristalizacijske posude ne prođe između 0,8 i 100 okretaja;
g) izoliranje tako nastalih kristala kristalnog kanagliflozin hemihidrata.
2. Postupak prema patentnom zahtjevu 1 naznačen time što je sustav otapala organski alkilni ester, naročito izopropil acetat.
3. Postupak prema patentnom zahtjevu 1 ili zahtjevu 2 naznačen time što se kanagliflozin u koraku a) dodaje sustavu otapala u obliku bezvodnog kanagliflozina.
4. Postupak prema patentnom zahtjevu 1 ili zahtjevu 2 naznačen time što se kanagliflozin u koraku a) dodaje sustavu otapala u obliku hemihidrata ili monohidrata.
5. Postupak prema patentnom zahtjevu 3 ili zahtjevu 4 naznačen time što je temperatura u koraku a) od 65°C do 80°C, ili od 70°C do 75°C.
6. Postupak prema patentnom zahtjevu 5 naznačen time što se temperatura u koraku b) kreće u rasponu od 50°C do 64°C, ili od 52°C do 60°C, ili od 54°C do 58°C.
7. Postupak prema patentnom zahtjevu 6 naznačen time što se temperatura u koraku d) kreće u rasponu od 30°C do 49°C, ili od 35°C do 47°C, ili od 38°C do 45°C, ili od 40°C do 42°C.
8. Postupak prema patentnom zahtjevu 7 naznačen time što se količina kanagliflozina u koraku a) kreće u rasponu od 200 g/litri do 500 g/litri, ili od 400 g/litri do 500 g/litri.
9. Postupak prema patentnom zahtjevu 8 naznačen time što se količina kristala za klijanje koji se koriste u koraku c) kreće u rasponu od 0,1 mas.% do 1,0 mas.%.
10. Postupak prema bilo kojem od patentnih zahtjeva 1 do 9 naznačen time što u koraku e) uklonjeni dio kristalne suspenzije koji je podvrgnut smanjenju veličine čestica, zagrijavanju i vraćanju u posudu za kristalizaciju je u količini koja iznosi od 1% do 80%, ili od 1% do 70%, ili od 2% do 60%, ili od 5% do 50%, cjelokupnog sadržaja posude za kristalizaciju.
11. Postupak prema patentnom zahtjevu 9 naznačen time što broj okretaja u koraku f) iznosi od 5 do 50, ili 10 do 40.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15201459 | 2015-12-21 | ||
| EP16172070 | 2016-05-31 | ||
| PCT/EP2016/081861 WO2017108752A1 (en) | 2015-12-21 | 2016-12-20 | Crystallization procedure for obtaining canagliflozin hemihydrate crystals |
| EP16819899.2A EP3394051B1 (en) | 2015-12-21 | 2016-12-20 | Crystallization procedure for obtaining canagliflozin hemihydrate crystals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20200755T1 true HRP20200755T1 (hr) | 2020-07-24 |
Family
ID=57681580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20200755TT HRP20200755T1 (hr) | 2015-12-21 | 2020-05-11 | Postupak kristalizacije za dobivanje kristala kanagliflozin hemihidrata |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US10323025B2 (hr) |
| EP (1) | EP3394051B1 (hr) |
| JP (1) | JP6851379B2 (hr) |
| KR (1) | KR20180095839A (hr) |
| CN (1) | CN108368096B (hr) |
| AU (1) | AU2016376653B2 (hr) |
| CA (1) | CA3006237C (hr) |
| CY (1) | CY1124885T1 (hr) |
| DK (1) | DK3394051T3 (hr) |
| EA (1) | EA036793B1 (hr) |
| ES (1) | ES2794909T3 (hr) |
| HR (1) | HRP20200755T1 (hr) |
| HU (1) | HUE049895T2 (hr) |
| LT (1) | LT3394051T (hr) |
| PL (1) | PL3394051T3 (hr) |
| PT (1) | PT3394051T (hr) |
| SI (1) | SI3394051T1 (hr) |
| WO (1) | WO2017108752A1 (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021012044A1 (en) | 2019-07-22 | 2021-01-28 | Canopy Growth Corporation | Continuous crystallization of cannabinoids in a stirred-tank reactor |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2780403B3 (fr) * | 1998-06-24 | 2000-07-21 | Sanofi Sa | Nouvelle forme de l'irbesartan, procedes pour obtenir ladite forme et compositions pharmaceutiques en contenant |
| GB0301259D0 (en) * | 2003-01-20 | 2003-02-19 | Novartis Ag | Organic compounds |
| ES2844401T3 (es) | 2003-08-01 | 2021-07-22 | Mitsubishi Tanabe Pharma Corp | Compuestos novedosos que tienen actividad inhibidora frente a transportador de glucosa dependiente de sodio |
| KR101041895B1 (ko) * | 2006-08-15 | 2011-06-16 | 브로드콤 코포레이션 | 패킷 손실 후 디코딩된 오디오 신호의 시간 워핑 |
| UY30730A1 (es) | 2006-12-04 | 2008-07-03 | Mitsubishi Tanabe Pharma Corp | Forma cristalina del hemihidrato de 1-(b (beta)-d-glucopiranosil) -4-metil-3-[5-(4-fluorofenil) -2-tienilmetil]benceno |
| PL2451797T3 (pl) * | 2009-07-10 | 2013-08-30 | Janssen Pharmaceutica Nv | Proces krystalizacji dla 1-(ß-D-glukopiranozylo)-4-metylo-3-[5-(4-fluorofenylo)-2-tienylometylo]benzenu |
| US10323056B2 (en) | 2013-05-08 | 2019-06-18 | Lek Pharmaceuticals D.D. | Crystalline hydrates of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene |
| CZ305172B6 (cs) * | 2014-03-28 | 2015-05-27 | Bochemie A.S. | Diskontinuální krystalizační jednotka pro výrobu kulovitých krystalů |
| CN103896930B (zh) * | 2014-04-02 | 2016-08-17 | 安徽联创生物医药股份有限公司 | 卡格列净半水合物药用晶型的制备方法 |
-
2016
- 2016-12-20 KR KR1020187018513A patent/KR20180095839A/ko not_active Application Discontinuation
- 2016-12-20 HU HUE16819899A patent/HUE049895T2/hu unknown
- 2016-12-20 WO PCT/EP2016/081861 patent/WO2017108752A1/en active Application Filing
- 2016-12-20 ES ES16819899T patent/ES2794909T3/es active Active
- 2016-12-20 EA EA201891470A patent/EA036793B1/ru unknown
- 2016-12-20 JP JP2018532225A patent/JP6851379B2/ja active Active
- 2016-12-20 LT LTEP16819899.2T patent/LT3394051T/lt unknown
- 2016-12-20 CN CN201680074830.6A patent/CN108368096B/zh active Active
- 2016-12-20 SI SI201630770T patent/SI3394051T1/sl unknown
- 2016-12-20 CA CA3006237A patent/CA3006237C/en active Active
- 2016-12-20 AU AU2016376653A patent/AU2016376653B2/en active Active
- 2016-12-20 US US16/064,084 patent/US10323025B2/en active Active
- 2016-12-20 EP EP16819899.2A patent/EP3394051B1/en active Active
- 2016-12-20 DK DK16819899.2T patent/DK3394051T3/da active
- 2016-12-20 PL PL16819899T patent/PL3394051T3/pl unknown
- 2016-12-20 PT PT168198992T patent/PT3394051T/pt unknown
-
2020
- 2020-05-11 HR HRP20200755TT patent/HRP20200755T1/hr unknown
- 2020-07-09 CY CY20201100631T patent/CY1124885T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019504022A (ja) | 2019-02-14 |
| WO2017108752A1 (en) | 2017-06-29 |
| CY1124885T1 (el) | 2022-07-22 |
| SI3394051T1 (sl) | 2020-07-31 |
| CN108368096A (zh) | 2018-08-03 |
| CA3006237C (en) | 2023-10-03 |
| EP3394051A1 (en) | 2018-10-31 |
| JP6851379B2 (ja) | 2021-03-31 |
| PL3394051T3 (pl) | 2020-10-19 |
| DK3394051T3 (da) | 2020-07-20 |
| ES2794909T3 (es) | 2020-11-19 |
| PT3394051T (pt) | 2020-06-08 |
| US20190002449A1 (en) | 2019-01-03 |
| HUE049895T2 (hu) | 2020-11-30 |
| AU2016376653A1 (en) | 2018-06-07 |
| EA036793B1 (ru) | 2020-12-22 |
| KR20180095839A (ko) | 2018-08-28 |
| EP3394051B1 (en) | 2020-04-22 |
| CN108368096B (zh) | 2021-12-10 |
| EA201891470A1 (ru) | 2018-12-28 |
| CA3006237A1 (en) | 2017-06-29 |
| AU2016376653B2 (en) | 2020-07-30 |
| US10323025B2 (en) | 2019-06-18 |
| LT3394051T (lt) | 2020-08-10 |
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