ME02403B - POSTUPCI ZA PREČIŠĆAVANJE TRANS-(-)-Δ9-TETRAHIDROKANABINOLA l TRANS-(+) - Δ9 - TETRAHIDROKANABINOLA - Google Patents
POSTUPCI ZA PREČIŠĆAVANJE TRANS-(-)-Δ9-TETRAHIDROKANABINOLA l TRANS-(+) - Δ9 - TETRAHIDROKANABINOLAInfo
- Publication number
- ME02403B ME02403B MEP-2016-55A MEP5516A ME02403B ME 02403 B ME02403 B ME 02403B ME P5516 A MEP5516 A ME P5516A ME 02403 B ME02403 B ME 02403B
- Authority
- ME
- Montenegro
- Prior art keywords
- tetrahydrocannabinol
- trans
- phase
- composition
- alcoholic
- Prior art date
Links
Classifications
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- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- 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
- A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4875—Compounds of unknown constitution, e.g. material from plants or animals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Botany (AREA)
- Zoology (AREA)
- Otolaryngology (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Nutrition Science (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Claims (11)
1.Postupak za uklanjanje nečistoća iz kompozicije koja sadrži trans-(-) Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol pre kristalizacije (±)-Δ9-tetrahidrokanabinola, a postupak obuhvata:(a) dovođenje u kontakt trans-(-)-Δ9-tetrahidrokanabinola i trans-(+)-Δ9 tetrahidrokanabinola sa prvim organskim rastvaračem koji se ne meša sa vodom, alkoholom koji se meša sa vodom, vodom, i hidroksidom alkalnog metala, na taj način obrazujući bifaznu kompoziciju koja sadrži (i) prvu organski fazu i (ii) alkoholnu-kaustičnu fazu koja sadrži trans-(-)- Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol;(b) odvajanje alkoholno-kaustične faze koja sadrži trans-(-)-Δ9-tetrahidrokanabinol i trans-(+)-Δ9-tetrahidrokanabinol od prve organske faze;(c) dovođenje u kontakt alkoholno-kaustične faze sa kiselinom da bi se dobila alkoholna faza tretirana kiselinom.
2.Postupak za uklanjanje nečistoća iz kompozicije koja sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol pre kristalizacije (±)-Δ9-tetrahidrokanabinola, a postupak obuhvata: (a) dovođenje u kontakt trans-(-)-Δ9-tetrahidrokanabinola ili trans-(+)-Δ9-tetrahidrokanabinola sa prvim organskim rastvaračem koji se ne meša sa vodom, aloholom koji se meša sa vodom, vodom, i hidroksidom alkalnog metala, tako obrazujući bifaznu kompoziciju koja sadrži (i) prvu ogransku fazu, i (ii) alkoholno-kaustičnu fazu koja sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol; (b) odvajanje alkoholno-kaustične faze koja sadrži trans-(-)-Δ9-tetrahidrokanabinol ili trans-(+)-Δ9-tetrahidrokanabinol od prve organske faze; (c) dovođenje u kontakt alkoholno-kaustične faze sa kiselinom da bi se dobila alkoholna faza tretirana kiselinom.
3.Postupak prema zahtevu 1 ili 2, gde je kiselina limunska kiselina ili sirćetna kiselina.
4.Postupak prema bilo kom od zahteva 1 do 3, gde je kiselina dodata u količini dovoljnoj da se postigne pH od 5 do 9.
5.Postupak prema bilo kom od zahteva 1 do 4, koji obuhvata dodatni korak: (d) dovođenja u kontakt alkoholne faze tretirane sa drugim organskim rastvaračem koji se ne meša sa vodom da bi se obrazovala (i) druga organska faza koja sadrži Δ9-tetrahidrokanabinol i (ii) alkoholna faza tretirana kiselinom.
6.Postupak prema zahtevu 5, koji obuhvata dodatni korak (e) odvajanja druge organske faze od alkoholne faze koja je tretirana kiselinom.
7.Postupak dobijanja kristalnog (±)-Δ9-tetrahidrokanabinola koji obuhvata: omogućavanje kristalizacije trans-(-)-Δ9-tetrahidrokanabinola i trans-(+)-Δ9-tetrahidrokanabinola iz prve kompozicije koja sadrži trans-(-)-Δ9-tetrahidrokanabinol, trans-(+)-Δ9-tetrahidrokanabinol, i nepolarni organski rastvarač da bi se dobio kristalni (±)-Δ9-tetrahidrokanabinol, pri čemu je prva kompozicija dobijena (a) izvođenjem postupka prema bilo kom od zahteva 1 do 6, (b) odvajanjem Δ9-tetrahidrokanabinola iz dobijene faze koja sadrži Δ9-tetrahidrokanabinol; i (c) dovođenjem u kontakt Δ9-tetrahidrokanabinola iz koraka (b) sa nepolarnim organskim rastvaračem i opciono njegovim enantiomerom da bi se obrazovala prva kompozicija.
8.Postupak prema zahtevu 7, gde je nepolarni organski rastvarač ravnolančani ili razgranati (C4-C10)alifatični ugljovodonik, (C4-C10)cikloalifatični ugljovodonik, ili bilo koja njihova smeša, gde je ravnolančani ili razgranti ugljovodonik poželjno pentan, heksan, heptan, izooktan, ili bilo koja njihova smeša, a poželjnijo je n-heptan.
9.Postupak dobijanja kompozicije trans-(-)-Δ9-tetrahidrokanabinola, koji obuhvata: omogućavanje odvajanja kompozicije koja sadrži (±)-Δ9-tetrahidrokanabinol i eluacioni rastvarač na hiralnoj stacionarnoj fazi da se dobije kompozicija trans-(-)-Δ9-tetrahidrokanabinola, ili kompozicije trans-(+)-Δ9-tetrahidrokanabinola, koji obuhvata: omogućavanje odvajanja kompozicije koja sadrži (±)-Δ9-tetrahidrokanabinol i eluacioni rastvarač na hiralnoj stacionarnoj fazi da bi se dobila kompozicija trans-(+)-Δ9-tetrahidrokanabinola, gde je (±)-Δ9-tetrahidrokanabinol dobijen iz kristalnog (±)-Δ9-tetrahidrokanabinola, i gde je kristalni (±)-Δ9-tetrahidrokanabinol dobijen postupkom prema zahtevu 7 ili 8.
10.Postupak prema bilo kom od zahteva 7 do 9, gde trans-(-)-Δ9-tetrahidrokanabinol je prisutan u prvoj kompoziciji u količini od 0.75 do 1.25 molarnih ekvivalenata, poželjno od 0.9 do 1.1 molarnih ekvivalenata, poželjnije od 0.95 do 1.25 molarnih ekvivalenata i čak poželjnije 1 molarni ekvivalent po molarnom ekvivalentu trans-(+)-Δ9-tetrahidrokanabinola.
11.Postupak prema bilo kom od zahteva 7 do 10, gde (±)-Δ9-tetrahidrokanabinol obuhvata bar 95% u odnosnu na težinu, poželjno bar 98% u odnosu na težinu i poželjnije bar 99% u odnosu na težinu trans-(-)-Δ9-tetrahidrokanabinola i trans-(+)-Δ9-tetrahidrokanabinola u odnosu na ukupnu količinu kanabinoida.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63055604P | 2004-11-22 | 2004-11-22 | |
| EP10179374.3A EP2356987B1 (en) | 2004-11-22 | 2005-11-18 | Methods for purifying trans-(-)-delta9-tetrahydrocannabinol and trans-(+)-delta9-tetrahydrocannabinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02403B true ME02403B (me) | 2016-09-20 |
Family
ID=35789123
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2015-186A ME02306B (me) | 2004-11-22 | 2005-11-18 | Postupci za prečišćavanje trans-(-)-Δ⁹-tetrahidrokanabinola i trans-(+)- Δ⁹-tetrahidrokarabinola |
| MEP-2016-55A ME02403B (me) | 2004-11-22 | 2005-11-18 | POSTUPCI ZA PREČIŠĆAVANJE TRANS-(-)-Δ9-TETRAHIDROKANABINOLA l TRANS-(+) - Δ9 - TETRAHIDROKANABINOLA |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2015-186A ME02306B (me) | 2004-11-22 | 2005-11-18 | Postupci za prečišćavanje trans-(-)-Δ⁹-tetrahidrokanabinola i trans-(+)- Δ⁹-tetrahidrokarabinola |
Country Status (30)
| Country | Link |
|---|---|
| US (6) | US8383842B2 (me) |
| EP (3) | EP1824475B1 (me) |
| JP (3) | JP4995728B2 (me) |
| KR (1) | KR100919719B1 (me) |
| CN (2) | CN102151259A (me) |
| AR (1) | AR054989A1 (me) |
| AT (1) | ATE500824T1 (me) |
| AU (2) | AU2005305944B2 (me) |
| BR (1) | BRPI0519803A2 (me) |
| CA (2) | CA2587957C (me) |
| CY (1) | CY1111471T1 (me) |
| DE (1) | DE602005026852D1 (me) |
| DK (3) | DK2356987T3 (me) |
| EA (1) | EA012299B1 (me) |
| ES (3) | ES2556802T3 (me) |
| HR (3) | HRP20110385T1 (me) |
| HU (2) | HUE025904T2 (me) |
| IL (1) | IL183306A (me) |
| ME (2) | ME02306B (me) |
| MX (1) | MX2007006104A (me) |
| NO (1) | NO331831B1 (me) |
| NZ (1) | NZ556038A (me) |
| PL (3) | PL2289509T3 (me) |
| PT (2) | PT2289509E (me) |
| RS (3) | RS54338B1 (me) |
| SI (3) | SI2289509T1 (me) |
| TW (2) | TWI369203B (me) |
| UA (1) | UA88491C2 (me) |
| WO (1) | WO2006053766A1 (me) |
| ZA (1) | ZA200706837B (me) |
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| GB0702895D0 (en) * | 2007-02-14 | 2007-03-28 | Resolution Chemicals Ltd | Delta 9 tetrahydrocannabinol derivatives |
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