RU2001114197A - Способ получения сложных эфиров дельта-9-тетрагидроканна-бинола - Google Patents
Способ получения сложных эфиров дельта-9-тетрагидроканна-бинолаInfo
- Publication number
- RU2001114197A RU2001114197A RU2001114197/04A RU2001114197A RU2001114197A RU 2001114197 A RU2001114197 A RU 2001114197A RU 2001114197/04 A RU2001114197/04 A RU 2001114197/04A RU 2001114197 A RU2001114197 A RU 2001114197A RU 2001114197 A RU2001114197 A RU 2001114197A
- Authority
- RU
- Russia
- Prior art keywords
- substituted pyridine
- acid
- group
- formula
- lower alkyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 4-amino-substituted pyridine Chemical class 0.000 claims 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 4
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- 239000001384 succinic acid Substances 0.000 claims 2
- CYQFCXCEBYINGO-ZYMOGRSISA-N (6aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-ZYMOGRSISA-N 0.000 claims 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-Aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical group C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229940014800 succinic anhydride Drugs 0.000 claims 1
Claims (12)
2. Способ по п.1, где 4-аминозамещенным пиридином является соединение формулы:
где R1 и R2 каждый независимо представляет Н, необязательно замещенный низший алкил, необязательно замещенный арил, или, R1 и R2 могут быть взяты вместе с образованием карбоциклического или гетероциклического 5- или 6-членного кольца.
3. Способ по п.1, дополнительно включающий проведение реакции этерификации при дополнительном присутствии дополнительного органического амина.
5. Способ по п.1, где R представляет полуэфир янтарной кислоты.
6. Способ по п.1, где R представляет полуэфир малоновой кислоты.
7. Способ по п.1, где 4-замещенным пиридином является 4-пирролидинопиридин.
8. Способ по п.1, где 4-замещенным пиридином является 4-ди(низший алкил)аминопиридин.
9. Способ по п.1, где 4-замещенным пиридином является 4-диметиламинопиридин.
10. Способ по п.3, где органическим амином является моно-, ди- или три-(низший алкил)амин.
11. Способ по п.10, где органическим амином является триэтиламин.
12. Способ по п.1, где R представляет ацильный остаток янтарной кислоты, ангидридом кислоты является янтарный ангидрид, и основанием является смесь 4-диметиламинопиридина и триэтиламина.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/178,644 | 1998-10-26 | ||
US09/178,644 US6008383A (en) | 1998-10-26 | 1998-10-26 | Method of preparing delta-9-tetrahydrocannabinol esters |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2001114197A true RU2001114197A (ru) | 2003-07-20 |
RU2232759C2 RU2232759C2 (ru) | 2004-07-20 |
Family
ID=22653334
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2001114197/04A RU2232759C2 (ru) | 1998-10-26 | 1999-10-26 | Способ получения сложных эфиров дельта-9-тетрагидроканнабинола |
Country Status (26)
Country | Link |
---|---|
US (1) | US6008383A (ru) |
EP (1) | EP1124817B1 (ru) |
JP (1) | JP2002530279A (ru) |
KR (1) | KR100711951B1 (ru) |
CN (1) | CN1158275C (ru) |
AT (1) | ATE279405T1 (ru) |
AU (1) | AU770382B2 (ru) |
BR (1) | BR9914787A (ru) |
CA (1) | CA2348695C (ru) |
CZ (1) | CZ20011436A3 (ru) |
DE (1) | DE69921170T2 (ru) |
DK (1) | DK1124817T3 (ru) |
ES (1) | ES2232208T3 (ru) |
GB (1) | GB2358397A (ru) |
HK (1) | HK1042088A1 (ru) |
HU (1) | HU226777B1 (ru) |
IL (1) | IL142668A (ru) |
MX (1) | MXPA01004125A (ru) |
NO (1) | NO327128B1 (ru) |
NZ (1) | NZ511236A (ru) |
PL (1) | PL196944B1 (ru) |
PT (1) | PT1124817E (ru) |
RU (1) | RU2232759C2 (ru) |
SK (1) | SK5442001A3 (ru) |
WO (1) | WO2000029402A1 (ru) |
ZA (1) | ZA200103168B (ru) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6008383A (en) * | 1998-10-26 | 1999-12-28 | University Of Mississippi | Method of preparing delta-9-tetrahydrocannabinol esters |
AU3697200A (en) | 1999-02-04 | 2000-08-25 | New Millennium Pharmaceutical Research, Inc. | Method for enhancement of delivery of thc by the administration of its prodrugs via the nasal route |
EP1321159A1 (en) | 2001-12-21 | 2003-06-25 | CHIESI FARMACEUTICI S.p.A. | Pressurized metered dose inhaler (pMDI) actuators with laser drilled orifices |
AU2003287585B2 (en) * | 2002-11-12 | 2009-05-07 | Mallinckrodt Inc. | Cannabinoid crystalline derivatives and process of cannabinoid purification |
US20060051824A1 (en) * | 2004-09-03 | 2006-03-09 | Haoyun An | Tetrahydrocannabinoid antigens and method of use |
US8628796B2 (en) * | 2004-12-09 | 2014-01-14 | Insys Therapeutics, Inc. | Room-temperature stable dronabinol formulations |
JP2009510078A (ja) | 2005-09-29 | 2009-03-12 | エーエムアール テクノロジー インコーポレイテッド | Δ−9−テトラヒドロカンナビノールの生成法 |
WO2008019146A2 (en) * | 2006-08-04 | 2008-02-14 | Insys Therapeutics Inc. | Aqueous dronabinol formulations |
WO2008109027A2 (en) | 2007-03-02 | 2008-09-12 | University Of Tennessee Research Foundation, The | Tri-aryl/heteroaroaromatic cannabinoids and use thereof |
CA2698752A1 (en) * | 2007-08-06 | 2009-02-12 | Insys Therapeutics Inc. | Oral cannabinoid liquid formulations and methods of treatment |
AU2009308665B2 (en) * | 2008-10-31 | 2015-10-22 | The University Of Mississippi | Compositions containing delta-9-THC-amino acid esters and process of preparation |
US10239808B1 (en) | 2016-12-07 | 2019-03-26 | Canopy Holdings, LLC | Cannabis extracts |
WO2019152736A1 (en) | 2018-01-31 | 2019-08-08 | Canopy Holdings, LLC | Hemp powder |
WO2020077153A1 (en) | 2018-10-10 | 2020-04-16 | Canopy Holdings, LLC | Synthesis of cannabigerol |
US10569189B1 (en) * | 2019-05-17 | 2020-02-25 | NextLeaf Solutions Ltd. | Method for acetylation of cannabinoids |
US10954209B1 (en) * | 2019-09-15 | 2021-03-23 | NextLeaf Solutions Ltd. | Acetylation of cannabinoids using sulfuric acid catalyst |
CN113087743B (zh) * | 2020-01-08 | 2023-04-28 | 成都百裕制药股份有限公司 | 四氢大麻酚衍生物及其制备方法和在医药上的应用 |
US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4933633A (en) * | 1981-06-09 | 1990-06-12 | Adec, Inc. | Computer controlled energy monitoring system |
US4933363A (en) * | 1988-08-16 | 1990-06-12 | Elsohly Mahmoud A | Method for effecting systemic delivery of delta-9-tetrahydrocannabinol |
US6008383A (en) * | 1998-10-26 | 1999-12-28 | University Of Mississippi | Method of preparing delta-9-tetrahydrocannabinol esters |
-
1998
- 1998-10-26 US US09/178,644 patent/US6008383A/en not_active Expired - Lifetime
-
1999
- 1999-10-26 DK DK99972211T patent/DK1124817T3/da active
- 1999-10-26 EP EP99972211A patent/EP1124817B1/en not_active Expired - Lifetime
- 1999-10-26 CA CA002348695A patent/CA2348695C/en not_active Expired - Fee Related
- 1999-10-26 BR BR9914787-4A patent/BR9914787A/pt not_active Application Discontinuation
- 1999-10-26 JP JP2000582389A patent/JP2002530279A/ja active Pending
- 1999-10-26 GB GB0109941A patent/GB2358397A/en not_active Withdrawn
- 1999-10-26 SK SK544-2001A patent/SK5442001A3/sk unknown
- 1999-10-26 IL IL14266899A patent/IL142668A/xx not_active IP Right Cessation
- 1999-10-26 PT PT99972211T patent/PT1124817E/pt unknown
- 1999-10-26 ES ES99972211T patent/ES2232208T3/es not_active Expired - Lifetime
- 1999-10-26 RU RU2001114197/04A patent/RU2232759C2/ru not_active IP Right Cessation
- 1999-10-26 NZ NZ511236A patent/NZ511236A/xx unknown
- 1999-10-26 DE DE69921170T patent/DE69921170T2/de not_active Expired - Fee Related
- 1999-10-26 MX MXPA01004125A patent/MXPA01004125A/es not_active IP Right Cessation
- 1999-10-26 WO PCT/US1999/025141 patent/WO2000029402A1/en active IP Right Grant
- 1999-10-26 PL PL348118A patent/PL196944B1/pl not_active IP Right Cessation
- 1999-10-26 AT AT99972211T patent/ATE279405T1/de not_active IP Right Cessation
- 1999-10-26 KR KR1020017005204A patent/KR100711951B1/ko not_active IP Right Cessation
- 1999-10-26 AU AU12349/00A patent/AU770382B2/en not_active Ceased
- 1999-10-26 HU HU0104776A patent/HU226777B1/hu not_active IP Right Cessation
- 1999-10-26 CZ CZ20011436A patent/CZ20011436A3/cs unknown
- 1999-10-26 CN CNB998150606A patent/CN1158275C/zh not_active Expired - Fee Related
-
2001
- 2001-04-18 ZA ZA200103168A patent/ZA200103168B/en unknown
- 2001-04-23 NO NO20011999A patent/NO327128B1/no not_active IP Right Cessation
-
2002
- 2002-05-23 HK HK02103887A patent/HK1042088A1/xx not_active IP Right Cessation
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