NO327128B1 - Fremgangsmate ved fremstilling av delta-9-tetrahydrocannabinalestere under anvendelse av et 4-amino-substituert pyridin - Google Patents
Fremgangsmate ved fremstilling av delta-9-tetrahydrocannabinalestere under anvendelse av et 4-amino-substituert pyridin Download PDFInfo
- Publication number
- NO327128B1 NO327128B1 NO20011999A NO20011999A NO327128B1 NO 327128 B1 NO327128 B1 NO 327128B1 NO 20011999 A NO20011999 A NO 20011999A NO 20011999 A NO20011999 A NO 20011999A NO 327128 B1 NO327128 B1 NO 327128B1
- Authority
- NO
- Norway
- Prior art keywords
- thc
- ether
- reaction mixture
- delta
- hexane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- -1 4-amino-substituted pyridine Chemical class 0.000 title claims description 5
- 150000002148 esters Chemical class 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 3
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims description 35
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical group ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 14
- 229940014800 succinic anhydride Drugs 0.000 claims description 14
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 12
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- XXGMIHXASFDFSM-UHFFFAOYSA-N Delta9-tetrahydrocannabinol Natural products CCCCCc1cc2OC(C)(C)C3CCC(=CC3c2c(O)c1O)C XXGMIHXASFDFSM-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical group FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 229960004242 dronabinol Drugs 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 241000218236 Cannabis Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- YCBKSSAWEUDACY-IAGOWNOFSA-N 11-hydroxy-Delta(9)-tetrahydrocannabinol Chemical compound C1=C(CO)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 YCBKSSAWEUDACY-IAGOWNOFSA-N 0.000 description 1
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 1
- YVOODUUYDJKFDY-RTBURBONSA-N 4-[[(6ar,10ar)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl]oxy]-4-oxobutanoic acid Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(OC(=O)CCC(O)=O)=C3[C@@H]21 YVOODUUYDJKFDY-RTBURBONSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- CYQFCXCEBYINGO-DLBZAZTESA-N Dronabinol Natural products C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@H]21 CYQFCXCEBYINGO-DLBZAZTESA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 206010027603 Migraine headaches Diseases 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 206010029216 Nervousness Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000001663 anti-spastic effect Effects 0.000 description 1
- 239000002948 appetite stimulant Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 238000010579 first pass effect Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/178,644 US6008383A (en) | 1998-10-26 | 1998-10-26 | Method of preparing delta-9-tetrahydrocannabinol esters |
| PCT/US1999/025141 WO2000029402A1 (en) | 1998-10-26 | 1999-10-26 | Method of preparing delta-9-tetrahydrocannabinol esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20011999D0 NO20011999D0 (no) | 2001-04-23 |
| NO20011999L NO20011999L (no) | 2001-06-18 |
| NO327128B1 true NO327128B1 (no) | 2009-04-27 |
Family
ID=22653334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20011999A NO327128B1 (no) | 1998-10-26 | 2001-04-23 | Fremgangsmate ved fremstilling av delta-9-tetrahydrocannabinalestere under anvendelse av et 4-amino-substituert pyridin |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6008383A (da) |
| EP (1) | EP1124817B1 (da) |
| JP (1) | JP2002530279A (da) |
| KR (1) | KR100711951B1 (da) |
| CN (1) | CN1158275C (da) |
| AT (1) | ATE279405T1 (da) |
| AU (1) | AU770382B2 (da) |
| BR (1) | BR9914787A (da) |
| CA (1) | CA2348695C (da) |
| CZ (1) | CZ20011436A3 (da) |
| DE (1) | DE69921170T2 (da) |
| DK (1) | DK1124817T3 (da) |
| ES (1) | ES2232208T3 (da) |
| GB (1) | GB2358397A (da) |
| HU (1) | HU226777B1 (da) |
| IL (1) | IL142668A (da) |
| MX (1) | MXPA01004125A (da) |
| NO (1) | NO327128B1 (da) |
| NZ (1) | NZ511236A (da) |
| PL (1) | PL196944B1 (da) |
| PT (1) | PT1124817E (da) |
| RU (1) | RU2232759C2 (da) |
| SK (1) | SK5442001A3 (da) |
| WO (1) | WO2000029402A1 (da) |
| ZA (1) | ZA200103168B (da) |
Families Citing this family (20)
| 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 |
| WO2000045813A1 (en) * | 1999-02-04 | 2000-08-10 | 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 |
| MXPA05004966A (es) * | 2002-11-12 | 2005-08-02 | Mallinckrodt Inc | Derivados cristalinos de canabinoide y procesos de purificacion de canabinoide. |
| US20060051824A1 (en) * | 2004-09-03 | 2006-03-09 | Haoyun An | Tetrahydrocannabinoid antigens and method of use |
| EP1827393A4 (en) * | 2004-12-09 | 2012-04-18 | Insys Therapeutics Inc | AT ROOM TEMPERATURE, STABLE DRONABINOL FORMULATIONS |
| CA2623723A1 (en) * | 2005-09-29 | 2007-04-12 | Amr Technology, Inc. | Process for production of delta-9-tetrahydrocannabinol |
| WO2008019146A2 (en) * | 2006-08-04 | 2008-02-14 | Insys Therapeutics Inc. | Aqueous dronabinol formulations |
| CN101668425A (zh) | 2007-03-02 | 2010-03-10 | 田纳西州立大学研究基金会 | 三芳基/杂芳族大麻素类和其应用 |
| JP2010535774A (ja) * | 2007-08-06 | 2010-11-25 | インシス セラピューティクス インコーポレイテッド | 経口カンナビノイド液体製剤および治療方法 |
| HUE032158T2 (en) * | 2008-10-31 | 2017-09-28 | Univ Mississippi | Process for the preparation of delta9-THC amino acid esters |
| US10239808B1 (en) | 2016-12-07 | 2019-03-26 | Canopy Holdings, LLC | Cannabis extracts |
| CA3089994A1 (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 |
| EP4089081B1 (en) * | 2020-01-08 | 2025-07-23 | Chengdu Baiyu Pharmaceutical Co., Ltd. | Tetrahydrocannabinol derivative, and preparation method therefor and medical use thereof |
| WO2021139739A1 (zh) | 2020-01-08 | 2021-07-15 | 成都百裕制药股份有限公司 | 大麻二酚衍生物及其制备方法和在医药上的应用 |
| CN115605195A (zh) | 2020-03-04 | 2023-01-13 | 普利欧制药有限公司（Us） | 用于治疗大麻使用病症和缓解大麻素戒断的方法和组合物 |
| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3728360A (en) * | 1971-08-31 | 1973-04-17 | Little Inc A | Ester derivatives of tetrahydrocannabinol |
| 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 |
| US5389375A (en) * | 1993-05-21 | 1995-02-14 | University Of Mississippi | Stable suppository formulations effecting bioavailability of Δ9 -thc |
| RU2106350C1 (ru) * | 1996-01-16 | 1998-03-10 | Научно-исследовательский институт физической и органической химии Ростовского государственного университета | Производные 8,9-дигидроксантена и способ их получения |
| 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 CN CNB998150606A patent/CN1158275C/zh not_active Expired - Fee Related
- 1999-10-26 DK DK99972211T patent/DK1124817T3/da active
- 1999-10-26 NZ NZ511236A patent/NZ511236A/xx unknown
- 1999-10-26 HU HU0104776A patent/HU226777B1/hu not_active IP Right Cessation
- 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 PT PT99972211T patent/PT1124817E/pt unknown
- 1999-10-26 WO PCT/US1999/025141 patent/WO2000029402A1/en not_active Ceased
- 1999-10-26 KR KR1020017005204A patent/KR100711951B1/ko not_active Expired - Fee Related
- 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 AU AU12349/00A patent/AU770382B2/en not_active Ceased
- 1999-10-26 PL PL348118A patent/PL196944B1/pl not_active IP Right Cessation
- 1999-10-26 IL IL14266899A patent/IL142668A/xx not_active IP Right Cessation
- 1999-10-26 MX MXPA01004125A patent/MXPA01004125A/es not_active IP Right Cessation
- 1999-10-26 CZ CZ20011436A patent/CZ20011436A3/cs unknown
- 1999-10-26 DE DE69921170T patent/DE69921170T2/de not_active Expired - Fee Related
- 1999-10-26 AT AT99972211T patent/ATE279405T1/de not_active IP Right Cessation
- 1999-10-26 GB GB0109941A patent/GB2358397A/en not_active Withdrawn
- 1999-10-26 SK SK544-2001A patent/SK5442001A3/sk unknown
- 1999-10-26 JP JP2000582389A patent/JP2002530279A/ja active Pending
- 1999-10-26 BR BR9914787-4A patent/BR9914787A/pt not_active Application Discontinuation
-
2001
- 2001-04-18 ZA ZA200103168A patent/ZA200103168B/en unknown
- 2001-04-23 NO NO20011999A patent/NO327128B1/no not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO327128B1 (no) | Fremgangsmate ved fremstilling av delta-9-tetrahydrocannabinalestere under anvendelse av et 4-amino-substituert pyridin | |
| US6730519B2 (en) | Method of preparing delta-9-tetrahydrocannabinol | |
| US5389375A (en) | Stable suppository formulations effecting bioavailability of Δ9 -thc | |
| CN101448812A (zh) | 人免疫缺陷病毒复制的抑制剂 | |
| JP2002528718A (ja) | デルタ−９−テトラヒドロカンナビノール調製法 | |
| US5395834A (en) | New benzopyran compounds | |
| NO174050B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive benzopyranforbindelser | |
| EP0046652B1 (en) | Chromanol derivatives, their production and pharmaceutical compositions containing them | |
| JPS5824597A (ja) | ウルソデオキシコリン酸誘導体、その製法およびそれを有効成分とする医薬組成物 | |
| JPH0243749B2 (da) | ||
| CA1271191A (en) | Alpha-tocopherol (halo)uridine phosphoric acid diester, salts thereof, and methods for producing the same | |
| JP2025533244A (ja) | ケトアミド誘導体の結晶形およびその調製方法 | |
| CN109627229B (zh) | 一种酚性化合物 | |
| HK1042088B (en) | Method of preparing delta-9-tetrahydrocannabinol esters | |
| KR820000122B1 (ko) | 치환된 2-비닐-크로몬의 제조방법 | |
| JPH04338330A (ja) | チロシン硫酸塩からなる血小板凝集阻止剤 | |
| PL120365B1 (en) | Process for preparing novel benzocycloheptapyranes | |
| EP0033613A1 (en) | Chromanol derivatives, a process for their preparation and compositions containing them | |
| JPWO1994004520A1 (ja) | アスコフラノン及びアスコフラノン誘導体を主成分とする血中脂質低下剤，血糖低下剤並びにグリケイション阻害物 | |
| JPWO2002016336A1 (ja) | 新規ｆｔ−０５５４ａ物質及びその製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |