HRP20210503T1 - Kristalni oblici soli tapentadola i postupci za njihovu pripremu - Google Patents
Kristalni oblici soli tapentadola i postupci za njihovu pripremu Download PDFInfo
- Publication number
- HRP20210503T1 HRP20210503T1 HRP20210503TT HRP20210503T HRP20210503T1 HR P20210503 T1 HRP20210503 T1 HR P20210503T1 HR P20210503T T HRP20210503T T HR P20210503TT HR P20210503 T HRP20210503 T HR P20210503T HR P20210503 T1 HRP20210503 T1 HR P20210503T1
- Authority
- HR
- Croatia
- Prior art keywords
- tapentadol
- tartrate
- crystalline
- treatment
- free base
- Prior art date
Links
- KWTWDQCKEHXFFR-SMDDNHRTSA-N tapentadol Chemical class CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-SMDDNHRTSA-N 0.000 title claims 23
- 238000000034 method Methods 0.000 title claims 10
- 238000002360 preparation method Methods 0.000 title claims 4
- 229960005126 tapentadol Drugs 0.000 claims 22
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 19
- 229940095064 tartrate Drugs 0.000 claims 15
- 239000012458 free base Substances 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- XKSJVTDZSYZBGF-SBKWZQTDSA-N (2r,3r)-3-(3-methoxyphenyl)-n,n,2-trimethylpentan-1-amine;hydrochloride Chemical compound Cl.CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(OC)=C1 XKSJVTDZSYZBGF-SBKWZQTDSA-N 0.000 claims 2
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims 2
- 239000001358 L(+)-tartaric acid Substances 0.000 claims 2
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 235000002906 tartaric acid Nutrition 0.000 claims 2
- 239000011975 tartaric acid Substances 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000000113 differential scanning calorimetry Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000003759 ester based solvent Substances 0.000 claims 1
- 239000004210 ether based solvent Substances 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000005453 ketone based solvent Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000001757 thermogravimetry curve Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (12)
1. Kristalni spoj tapentadol tartarata formule-1b
[image]
2. Kristalni tapentadol tartarat prema zahtjevu 1, naznačen time što je navedeni kristalni oblik karakteriziran svojim uzorkom difrakcije X-zraka u prahu koji ima vrhove na 12.7, 14.1, 18.6, 20.0, 21.1, 21.6, 22.1, 23.7, 25.6 i 28.5 ± 0.2 stupnja od 2-theta.
3. Kristalni tapentadol tartarat prema zahtjevu 2, ima endotermu na 132°C±3°C u svom diferencijalnom skenirajućem kalorimetrijskom (DSC) termogramu.
4. Kristalni tapentadol tartarat prema zahtjevu 2 ili 3, naznačen time što su apsorpcijski vrhovi na 3319, 3237, 2960, 1731, 1597, 1305, 1263, 1213, 791, 679 i 485 cm-1 u svom infracrvenom spektru.
5. Kristalni tapentadol tartarat prema bilo kojem od zahtjeva 1 do 4, naznačen time što kristalni tapentadol tartarat ima čistoću od >99% pomoću HPLC.
6. Postupak za pripremu kristalnog tapentadol tartarata kako je definiran u zahtjevu 1, navedeni postupak obuhvaća korak: obrada slobodne baze tapentadola vinskom kiselinom u prikladnom otapalu da se dobije tapentadol tartarat formule-1b.
7. Postupak prema patentnom zahtjevu 6, navedeni postupak obuhvaća korake:
a) obrada (2R,3R)-3-(3-metoksifenil)-N,N,2-trimetilpentan-1-amin hidroklorida vodenom otopinom hidrogen bromida da se dobije slobodna baza tapentadola,
b) izborno izoliranje slobodne baze tapentadola,
c) obrada slobodne baze tapentadola dobivene u koraku -a) ili koraku-b) vinskom kiselinom u prikladnom otapalu da se dobije tapentadol tartarat formule-1b,
d) izborno pročišćavanje spoja dobivenog u koraku-c) od prikladnog otapala.
8. Postupak za pripremu kristalnog tapentadol tartarata kako je definiran u zahtjevu 2, navedeni postupak obuhvaća korak: obrada slobodne baze tapentadola s L-(+) vinskom kiselinom u acetonu da se dobije kristalni tapentadol tartarat formule-1b.
9. Postupak za pripremu kristalnog tapentadol tartarata prema zahtjevu 8, navedeni postupak obuhvaća korake:
a) obrada (2R,3R)-3-(3-metoksifenil)-N,N,2-trimetilpentan-1-amin hidroklorida vodenom otopinom hidrogen bromida da se dobije slobodna baza tapentadola,
b) obrada slobodne baze tapentadola in-situ s L-(+) vinskom kiselinom u acetonu da se dobije kristalni spoj tapentadol tartarata formule-1b.
10. Postupak prema bilo kojem od zahtjeva 6 i 7, naznačen time što se prikladno otapalo bira između alkoholnih otapala, ketonskih otapala, esterskih otapala, ugljikovodičnih otapala, eterskih otapala, kloro otapala i njihove mješavine ili izborno u kombinaciji s vodom.
11. Kristalni tapentadol tartarat kako je definiran u bilo kojem od zahtjeva 2 do 5, u farmaceutskom pripravku za uporabu u liječenju boli.
12. Farmaceutski pripravak koji sadrži kristalni tapentadol tartarat kako je definiran u bilo kojem od zahtjeva 2 do 5, i farmaceutski prihvatljiv nosač.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN6191CH2015 | 2015-11-17 | ||
| PCT/IN2016/000270 WO2017085734A1 (en) | 2015-11-17 | 2016-11-16 | Crystalline forms of tapentadol salts and process for preparation thereof |
| EP16865892.0A EP3377049B1 (en) | 2015-11-17 | 2016-11-16 | Crystalline forms of tapentadol salts and process for preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210503T1 true HRP20210503T1 (hr) | 2021-10-15 |
Family
ID=58718521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210503TT HRP20210503T1 (hr) | 2015-11-17 | 2021-03-29 | Kristalni oblici soli tapentadola i postupci za njihovu pripremu |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP3377049B1 (hr) |
| DK (1) | DK3377049T3 (hr) |
| ES (1) | ES2860907T3 (hr) |
| HR (1) | HRP20210503T1 (hr) |
| HU (1) | HUE054338T2 (hr) |
| PL (1) | PL3377049T3 (hr) |
| WO (1) | WO2017085734A1 (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT3650439T (pt) | 2010-07-23 | 2021-03-03 | Gruenenthal Gmbh | Sais ou cocristais de 3-(3-dimetilamino-1-etil-2-metilpropil)fenol |
| LT3995135T (lt) | 2020-11-10 | 2022-08-25 | Grünenthal GmbH | Tapentadolio l-(+)-vyno rūgščių druskos pailginto atpalaidavimo |
| MX2023005472A (es) | 2020-11-10 | 2023-05-22 | Gruenenthal Gmbh | Formas de dosificacion de liberacion sostenida de una sal de tapentadol con acido l-(+)-tartarico. |
| DE202020005470U1 (de) | 2020-11-10 | 2022-01-25 | Grünenthal GmbH | Darreichungsformen mit verlängerter Freisetzung eines Salzes von Tapentadol mit L-(+)-Weinsäure |
| EP4011369A1 (en) | 2020-12-14 | 2022-06-15 | G.L. Pharma GmbH | Aqueous pharmaceutical composition comprising tapentadol tartrate |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4426245A1 (de) | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
| CA2572352A1 (en) | 2004-07-01 | 2006-01-12 | Gruenenthal Gmbh | Oral dosage form safeguarded against abuse containing (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol |
| TWI496762B (zh) | 2006-07-24 | 2015-08-21 | 製備（１ｒ，２ｒ）-３-（３-二甲胺基-１-乙基-２-甲基-丙基）-酚之方法 | |
| DE102007019417A1 (de) | 2007-04-23 | 2008-11-13 | Grünenthal GmbH | Tapentadol zur Schmerzbehandlung bei Arthrose |
| US8288592B2 (en) * | 2009-09-22 | 2012-10-16 | Actavis Group Ptc Ehf | Solid state forms of tapentadol salts |
| PT3650439T (pt) | 2010-07-23 | 2021-03-03 | Gruenenthal Gmbh | Sais ou cocristais de 3-(3-dimetilamino-1-etil-2-metilpropil)fenol |
| WO2012051246A1 (en) * | 2010-10-12 | 2012-04-19 | Ratiopharm Gmbh | Tapentadol hydrobromide and crystalline forms thereof |
| EP2943454B1 (en) | 2013-01-10 | 2021-08-18 | KRKA, tovarna zdravil, d.d. | Tapentadol maleate and crystalline forms thereof |
| CN103553940A (zh) * | 2013-11-07 | 2014-02-05 | 南京艾德凯腾生物医药有限责任公司 | 一种新晶型盐酸他喷他多的制备方法 |
-
2016
- 2016-11-16 HU HUE16865892A patent/HUE054338T2/hu unknown
- 2016-11-16 PL PL16865892T patent/PL3377049T3/pl unknown
- 2016-11-16 ES ES16865892T patent/ES2860907T3/es active Active
- 2016-11-16 WO PCT/IN2016/000270 patent/WO2017085734A1/en active Application Filing
- 2016-11-16 EP EP16865892.0A patent/EP3377049B1/en not_active Revoked
- 2016-11-16 DK DK16865892.0T patent/DK3377049T3/da active
-
2021
- 2021-03-29 HR HRP20210503TT patent/HRP20210503T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUE054338T2 (hu) | 2021-08-30 |
| EP3377049A1 (en) | 2018-09-26 |
| EP3377049B1 (en) | 2021-01-06 |
| ES2860907T3 (es) | 2021-10-05 |
| EP3377049A4 (en) | 2019-06-12 |
| DK3377049T3 (en) | 2021-04-12 |
| PL3377049T3 (pl) | 2021-06-28 |
| WO2017085734A1 (en) | 2017-05-26 |
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