HRP20161485T1 - Polimorfna forma n-[4-(trifluorometil)benzil)-4-metoksibutiramida - Google Patents
Polimorfna forma n-[4-(trifluorometil)benzil)-4-metoksibutiramida Download PDFInfo
- Publication number
- HRP20161485T1 HRP20161485T1 HRP20161485TT HRP20161485T HRP20161485T1 HR P20161485 T1 HRP20161485 T1 HR P20161485T1 HR P20161485T T HRP20161485T T HR P20161485TT HR P20161485 T HRP20161485 T HR P20161485T HR P20161485 T1 HRP20161485 T1 HR P20161485T1
- Authority
- HR
- Croatia
- Prior art keywords
- trifluoromethyl
- benzyl
- methoxybutyramide
- polymorphic form
- accordance
- Prior art date
Links
- QLZOWJNFLXSDSH-UHFFFAOYSA-N 4-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]butanamide Chemical compound COCCCC(=O)NCC1=CC=C(C(F)(F)F)C=C1 QLZOWJNFLXSDSH-UHFFFAOYSA-N 0.000 title claims 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- PRDBLLIPPDOICK-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=C(C(F)(F)F)C=C1 PRDBLLIPPDOICK-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- VHDGWXQBVWAMJA-UHFFFAOYSA-N methyl 4-methoxybutanoate Chemical compound COCCCC(=O)OC VHDGWXQBVWAMJA-UHFFFAOYSA-N 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000002747 voluntary effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Addiction (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (14)
1. Polimorfni oblik A N-[4-(trifluorometil)benzil]-4-metoksibutiramida formule:
[image]
sa narednim maksimumima na difrakcijskim stupnjevima (2-theta) u difrakciji X-zraka na prahu ± 0.2:
9.7; 12.0; 18.0; 24.1; 25.9.
2. Poliformni oblik A u skladu sa zahtjevom 1, sa narednim maksimumima na difrakcijskim stupnjevima u difrakciji X-zraka na praškastom kristalu ± 0.2:
[image]
3. Postupak dobijanja polimorfnog oblika A N-[4-(trifluorometil)benzil]-4-metoksibutiramida iz zahtjeva 1 ili 2, koji uključuje slijedeće korake:
i) reakciju 4-trifluorometil-benzilamina sa metil 4-metoksibutiratom, u prisustvu katalizatora, čime se dobija nepročišćeni N-[4-(trifluorometil)benzil]-4-metoksibutiramid; i
(ii) dobijanje kristalnog polimorfnog oblika A iz otopine nepročišćenog N-[4-(trifluorometil)benzil]-4-metoksibutiramida u organskom otapalu, iz kojeg se kristalizira polimorfni oblik A N-[4-(trifluorometil)benzil]-4-metoksibutiramida, naznačeno time što je organsko otapalo izabrano između toluena i smjese etilacetata/n-heksana.
4. Postupak u skladu sa zahtjevom 3, naznačen time što je 4-trifluorometil-benzil amin dobijen u reakciji 4-trifluorometil-benzaldehida sa hidroksilamin-HCl, prema narednoj shemi:
[image]
5. Postupak u skladu sa zahtjevima 3 i 4, naznačen time što je u koraku (i), kao katalizator uporabljen 30% natrijev-metilat u metanolu.
6. Postupak u skladu sa zahtjevom 5, naznačen time što je organsko otapalo smjesa etilacetata/n-heksana.
7. Postupak u skladu sa zahtjevom 6, naznačen time što je smjesa etilacetata : n-heksana je u odnosu od 1:4 do 1:2, poželjno 1:3.
8. Polimorfni oblik A N-[4-(trifluorometil)benzil]-4-metoksibutiramida u skladu sa zahtjevima 1 ili 2, za primjenu kao medikamenta.
9. Farmaceutski pripravak koji kao aktivni sastojak uključuje efektivnu količinu polimorfnog oblika A N-[4-(trifluorometil)benzil]-4-metoksibutiramida, u skladu sa zahtjevima 1 ili 2 i neki farmaceutski prihvatljiv nosač.
10. Farmaceutski pripravak u skladu sa zahtjevom 9, naznačen time što je spoj u polimorfnom obliku A prisutan u količini od 12.5 do 50% mase.
11. Polimorfni oblik A N-[4-(trifluorometil)benzil]-4-metoksibutiramida, u skladu sa zahtjevima 1 ili 2, za primjenu u terapiji ovisnosti od narkotika i alkoholizma.
12. Polimorfni oblik A N-[4-(trifluorometil)benzil]-4-metoksibutiramida, za primjenu u skladu sa zahtjevom 11 u smanjenju voljne konzumacije etil-lkohola i/ili u terapiji apstinencijalnog sindroma.
13. Polimorfni oblik N-[4-(trifluorometil)benzil]-4-metoksibutiramida, za primjenu u skladu sa zahtjevom 11, naznačen time što je polimorfni oblik A N-[4-(trifluorometil)benzil]-4-metoksibutiramida u dozi od 5 do 50 mg/kg.
14. Polimorfni oblik A N-[4-(trifluorometil)benzil]-4-metoksibutiramida, za primjenu u skladu sa zahtjevom 13, naznačen time što je polimorfni oblik A N-[4-(trifluorometil)benzil]-4-metoksibutiramida u dozi od 5 do 10 mg/kg.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07120551A EP2062875A1 (en) | 2007-11-13 | 2007-11-13 | New polymorphic forms of n-[4-(trifluoromethyl)benzyl]-4-methoxybutyramide |
| EP08849561.9A EP2220027B1 (en) | 2007-11-13 | 2008-11-12 | Polymorphic form of n-[4-(trifluoromethyl)benzyl)-4-methoxybutyramide |
| PCT/EP2008/065367 WO2009062949A1 (en) | 2007-11-13 | 2008-11-12 | New polymorphic forms of n-[4-(trifluoromethyl)benzyl]-4-methoxybutyramide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20161485T1 true HRP20161485T1 (hr) | 2016-12-30 |
Family
ID=39186150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20161485TT HRP20161485T1 (hr) | 2007-11-13 | 2016-11-10 | Polimorfna forma n-[4-(trifluorometil)benzil)-4-metoksibutiramida |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | USRE47078E1 (hr) |
| EP (3) | EP2062875A1 (hr) |
| JP (1) | JP5448197B2 (hr) |
| CN (1) | CN101855200B (hr) |
| AU (1) | AU2008323005B2 (hr) |
| BR (1) | BRPI0819370A2 (hr) |
| CA (2) | CA2911120C (hr) |
| CY (1) | CY1118305T1 (hr) |
| DK (1) | DK2220027T3 (hr) |
| EA (1) | EA017718B9 (hr) |
| ES (1) | ES2602358T3 (hr) |
| HK (1) | HK1223606A1 (hr) |
| HR (1) | HRP20161485T1 (hr) |
| HU (1) | HUE031858T2 (hr) |
| IL (2) | IL205661A (hr) |
| LT (1) | LT2220027T (hr) |
| NZ (1) | NZ586109A (hr) |
| PL (1) | PL2220027T3 (hr) |
| PT (1) | PT2220027T (hr) |
| RS (1) | RS55310B1 (hr) |
| SI (1) | SI2220027T1 (hr) |
| UA (1) | UA101816C2 (hr) |
| WO (1) | WO2009062949A1 (hr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITUA20164040A1 (it) * | 2016-06-01 | 2017-12-01 | Laboratorio Farm C T S R L | Procedimento per la preparazione di polimorfo a |
| US20200253196A1 (en) * | 2017-11-03 | 2020-08-13 | Dow Global Technologies Llc | Solvents for agricultural applications and pesticide formulations |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1283782B1 (it) * | 1996-08-09 | 1998-04-30 | Ct Lab Farm Srl | Uso di ammidi dell'acido gamma-idrossibutirrico nel trattamento di tossicodipendenze,ed in particolare sell'alcolismo |
| JP2000273069A (ja) * | 1999-03-23 | 2000-10-03 | Central Glass Co Ltd | トリフルオロメチルベンジルアミンの製造方法 |
| JP2001294559A (ja) * | 2000-04-13 | 2001-10-23 | Central Glass Co Ltd | トリフルオロメチルベンジルアミンの製造方法 |
-
2007
- 2007-11-13 EP EP07120551A patent/EP2062875A1/en not_active Withdrawn
-
2008
- 2008-11-12 CN CN200880115643.3A patent/CN101855200B/zh active Active
- 2008-11-12 AU AU2008323005A patent/AU2008323005B2/en active Active
- 2008-11-12 NZ NZ586109A patent/NZ586109A/en unknown
- 2008-11-12 UA UAA201005771A patent/UA101816C2/ru unknown
- 2008-11-12 DK DK08849561.9T patent/DK2220027T3/en active
- 2008-11-12 ES ES08849561.9T patent/ES2602358T3/es active Active
- 2008-11-12 LT LTEP08849561.9T patent/LT2220027T/lt unknown
- 2008-11-12 BR BRPI0819370 patent/BRPI0819370A2/pt not_active Application Discontinuation
- 2008-11-12 CA CA2911120A patent/CA2911120C/en active Active
- 2008-11-12 EP EP08849561.9A patent/EP2220027B1/en active Active
- 2008-11-12 WO PCT/EP2008/065367 patent/WO2009062949A1/en active Application Filing
- 2008-11-12 HU HUE08849561A patent/HUE031858T2/en unknown
- 2008-11-12 RS RS20160975A patent/RS55310B1/sr unknown
- 2008-11-12 CA CA2705508A patent/CA2705508C/en active Active
- 2008-11-12 EA EA201000801A patent/EA017718B9/ru unknown
- 2008-11-12 US US15/172,283 patent/USRE47078E1/en active Active
- 2008-11-12 PT PT88495619T patent/PT2220027T/pt unknown
- 2008-11-12 SI SI200831704A patent/SI2220027T1/sl unknown
- 2008-11-12 EP EP15192055.0A patent/EP3012246B1/en active Active
- 2008-11-12 JP JP2010532617A patent/JP5448197B2/ja active Active
- 2008-11-12 PL PL08849561T patent/PL2220027T3/pl unknown
- 2008-11-12 US US12/742,304 patent/US8742172B2/en not_active Ceased
-
2010
- 2010-05-10 IL IL205661A patent/IL205661A/en active IP Right Grant
-
2015
- 2015-11-23 IL IL242736A patent/IL242736B/en active IP Right Grant
-
2016
- 2016-10-19 HK HK16112023.8A patent/HK1223606A1/zh unknown
- 2016-11-10 HR HRP20161485TT patent/HRP20161485T1/hr unknown
- 2016-11-17 CY CY20161101190T patent/CY1118305T1/el unknown
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