CS195337B2 - Process for selective production of optical acive 6a,10a-trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,7,10,10a-hexahydro-9h-dibenzo/b,d/pyran-9-ones - Google Patents
Process for selective production of optical acive 6a,10a-trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,7,10,10a-hexahydro-9h-dibenzo/b,d/pyran-9-ones Download PDFInfo
- Publication number
- CS195337B2 CS195337B2 CS774519A CS451977A CS195337B2 CS 195337 B2 CS195337 B2 CS 195337B2 CS 774519 A CS774519 A CS 774519A CS 451977 A CS451977 A CS 451977A CS 195337 B2 CS195337 B2 CS 195337B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- pyran
- hexahydro
- hydroxy
- dibenzo
- dimethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 230000003287 optical effect Effects 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- -1 5-substituted resorcinol Chemical class 0.000 claims abstract description 31
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- NNPXUZFTLBPVNP-UHFFFAOYSA-N 6,6-dimethylbicyclo[3.1.1]hept-2-en-4-one Chemical compound C1C2C(C)(C)C1C=CC2=O NNPXUZFTLBPVNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XMHXPSAHLRZYKH-UHFFFAOYSA-N 2,3,4,4a,6,6a-hexahydrobenzo[c]chromen-1-one Chemical class C1=CC=CC2=C3C(=O)CCCC3OCC21 XMHXPSAHLRZYKH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000000707 stereoselective effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XMHXPSAHLRZYKH-JOYOIKCWSA-N (4aR,6aR)-2,3,4,4a,6,6a-hexahydrobenzo[c]chromen-1-one Chemical class C1=CC=CC2=C3C(=O)CCC[C@H]3OC[C@@H]21 XMHXPSAHLRZYKH-JOYOIKCWSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NNPXUZFTLBPVNP-BQBZGAKWSA-N (1r,5r)-6,6-dimethylbicyclo[3.1.1]hept-2-en-4-one Chemical compound C1[C@@H]2C(C)(C)[C@H]1C=CC2=O NNPXUZFTLBPVNP-BQBZGAKWSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- NFRKUDYZEVQXTE-UHFFFAOYSA-N 2-chloropentane Chemical compound CCCC(C)Cl NFRKUDYZEVQXTE-UHFFFAOYSA-N 0.000 description 1
- GWBGUJWRDDDVBI-UHFFFAOYSA-N 5-(2-methyloctan-2-yl)benzene-1,3-diol Chemical compound CCCCCCC(C)(C)C1=CC(O)=CC(O)=C1 GWBGUJWRDDDVBI-UHFFFAOYSA-N 0.000 description 1
- HOZPFQGNHPSZTC-UHFFFAOYSA-N 5-heptan-4-ylbenzene-1,3-diol Chemical compound CCCC(CCC)C1=CC(O)=CC(O)=C1 HOZPFQGNHPSZTC-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000008096 xylene Substances 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/740,507 US4075230A (en) | 1976-11-10 | 1976-11-10 | Preparation of optically active trans-hexahydrodibenzopyranones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195337B2 true CS195337B2 (en) | 1980-01-31 |
Family
ID=24976797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS774519A CS195337B2 (en) | 1976-11-10 | 1977-07-06 | Process for selective production of optical acive 6a,10a-trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,7,10,10a-hexahydro-9h-dibenzo/b,d/pyran-9-ones |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4075230A (fr) |
| JP (1) | JPS5943469B2 (fr) |
| AR (1) | AR213651A1 (fr) |
| AT (1) | AT351533B (fr) |
| AU (1) | AU511606B2 (fr) |
| BE (1) | BE856414A (fr) |
| BG (1) | BG28059A3 (fr) |
| CA (1) | CA1088081A (fr) |
| CH (1) | CH633789A5 (fr) |
| CS (1) | CS195337B2 (fr) |
| DD (1) | DD132967A5 (fr) |
| DE (1) | DE2729844C2 (fr) |
| DK (1) | DK146852C (fr) |
| ES (1) | ES460390A1 (fr) |
| FR (1) | FR2370743A1 (fr) |
| GB (1) | GB1580488A (fr) |
| GR (1) | GR66416B (fr) |
| HU (1) | HU177202B (fr) |
| IE (1) | IE45249B1 (fr) |
| IL (1) | IL52426A (fr) |
| MX (1) | MX4739E (fr) |
| NL (1) | NL180315C (fr) |
| NZ (1) | NZ184525A (fr) |
| PH (1) | PH13818A (fr) |
| PL (1) | PL104313B1 (fr) |
| PT (1) | PT66747B (fr) |
| SE (1) | SE428021B (fr) |
| SU (1) | SU740155A3 (fr) |
| YU (1) | YU163777A (fr) |
| ZA (1) | ZA773956B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL80411A (en) * | 1986-10-24 | 1991-08-16 | Raphael Mechoulam | Preparation of dibenzopyranol derivatives and pharmaceutical compositions containing them |
| CN102766128A (zh) * | 2005-09-29 | 2012-11-07 | 阿尔巴尼分子研究公司 | δ-9-四氢大麻酚的生成方法 |
| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856823A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | DIBENZO (b,d) PYRANS |
| US3856821A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | ALKOXY DIBENZO (b,d) PYRANS |
-
1976
- 1976-11-10 US US05/740,507 patent/US4075230A/en not_active Expired - Lifetime
-
1977
- 1977-06-29 GB GB27111/77A patent/GB1580488A/en not_active Expired
- 1977-06-30 ZA ZA00773956A patent/ZA773956B/xx unknown
- 1977-06-30 NZ NZ184525A patent/NZ184525A/xx unknown
- 1977-06-30 PT PT66747A patent/PT66747B/pt unknown
- 1977-06-30 SE SE7707634A patent/SE428021B/xx not_active IP Right Cessation
- 1977-06-30 PH PH19937A patent/PH13818A/en unknown
- 1977-06-30 IL IL52426A patent/IL52426A/xx unknown
- 1977-06-30 CA CA281,750A patent/CA1088081A/fr not_active Expired
- 1977-07-01 AU AU26683/77A patent/AU511606B2/en not_active Expired
- 1977-07-01 DE DE2729844A patent/DE2729844C2/de not_active Expired
- 1977-07-01 BG BG036776A patent/BG28059A3/xx unknown
- 1977-07-01 YU YU01637/77A patent/YU163777A/xx unknown
- 1977-07-04 ES ES460390A patent/ES460390A1/es not_active Expired
- 1977-07-04 AR AR268311A patent/AR213651A1/es active
- 1977-07-04 SU SU772502044A patent/SU740155A3/ru active
- 1977-07-04 MX MX775868U patent/MX4739E/es unknown
- 1977-07-04 CH CH819577A patent/CH633789A5/de not_active IP Right Cessation
- 1977-07-04 JP JP52081490A patent/JPS5943469B2/ja not_active Expired
- 1977-07-04 BE BE1008248A patent/BE856414A/fr not_active IP Right Cessation
- 1977-07-04 PL PL1977199367A patent/PL104313B1/pl unknown
- 1977-07-05 DD DD7700199896A patent/DD132967A5/xx unknown
- 1977-07-05 NL NLAANVRAGE7707463,A patent/NL180315C/xx not_active IP Right Cessation
- 1977-07-05 FR FR7720646A patent/FR2370743A1/fr active Granted
- 1977-07-05 HU HU77EI754A patent/HU177202B/hu unknown
- 1977-07-05 GR GR53878A patent/GR66416B/el unknown
- 1977-07-05 IE IE1390/77A patent/IE45249B1/en unknown
- 1977-07-05 DK DK301577A patent/DK146852C/da not_active IP Right Cessation
- 1977-07-06 CS CS774519A patent/CS195337B2/cs unknown
- 1977-07-06 AT AT483777A patent/AT351533B/de not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3278159B2 (ja) | （３ｒ，４ｒ）−δ▲上６▼−テトラヒドロカンナビノール−７−酸 | |
| KR100395280B1 (ko) | 신규한3환성화합물및그를함유하는의약조성물 | |
| US10538790B2 (en) | Bioenzymatic synthesis of THC-v, CBV and CBN and their use as therapeutic agents | |
| US20160184261A1 (en) | Methods for purifying trans-(-)-delta9-tetrahydrocannabinol and trans-(+)-delta9-tetrahydrocannabinol | |
| EP0506532A1 (fr) | Nouveaux dérivés de l'indole, procédé de préparation et médicaments les contenant | |
| JP3908270B2 (ja) | アシルフルベン類似体およびその医薬組成物 | |
| KR100709317B1 (ko) | 살리실산아미드유도체 | |
| JPS5943467B2 (ja) | トランス−ヘキサヒドロジベンゾ〔ｂ，ｄ〕ピラン−９−オン類の製造法 | |
| US5015666A (en) | Triarylcyclopropanes as antiestrogens and antitumor agents | |
| KR100335169B1 (ko) | 포화 고리를 갖는 신규한 트리시클릭 화합물 및 이를포함하는 의약 조성물 | |
| US4395560A (en) | Preparation of 6a,10a-trans-hexahydrodibenzopyranones | |
| FI68048C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade oxirankarboxylsyror | |
| De la Torre et al. | [60] Fullerene–flavonoid dyads | |
| US4988682A (en) | Myo-inositol analogs and method for their use | |
| Mewett et al. | Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors | |
| CS195337B2 (en) | Process for selective production of optical acive 6a,10a-trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,7,10,10a-hexahydro-9h-dibenzo/b,d/pyran-9-ones | |
| JPS5943468B2 (ja) | ６ａ，１０ａ−トランス−ヘキサヒドロジベンゾピラノン誘導体の製造方法 | |
| KR810000429B1 (ko) | 트랜스-헥사하이드로디벤조피라논의 제조방법 | |
| EP0259228B1 (fr) | Dérivés 5-aminoéthylés de l'oxazolidinone-2, leur procédé de préparation et leur application en thérapeutique | |
| US4937390A (en) | Compound useful for the production of 3-deoxy-3-fluoro-myo-inositol | |
| US4283413A (en) | Method for inhibiting aggregation of human thrombocytes | |
| JP2587979B2 (ja) | テルペン系化合物 | |
| CN108395431B (zh) | 一类吴茱萸碱拼合adt-oh类h2s供体衍生物及其制备方法和用途 | |
| FR2545488A1 (fr) | Nouveaux carbamates cycliques a chaine laterale du type arylmethyle ou aryloxymethyle, leurs procedes de preparation et leur application en therapeutique | |
| SU1098228A1 (ru) | Бисульфитное производное (1-фенил-2-метилиндено /1,2- @ / пиррол-4-онил-3)глиоксал обладающее противовирусной активностью |