CA1188702A - Preparation of 6a,10a-trans-hexahydrodibenzopyranones - Google Patents
Preparation of 6a,10a-trans-hexahydrodibenzopyranonesInfo
- Publication number
- CA1188702A CA1188702A CA000427823A CA427823A CA1188702A CA 1188702 A CA1188702 A CA 1188702A CA 000427823 A CA000427823 A CA 000427823A CA 427823 A CA427823 A CA 427823A CA 1188702 A CA1188702 A CA 1188702A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- trans
- methoxy
- carbinol
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title description 3
- JMTOWIGWAQDRBE-UHFFFAOYSA-N cyclohexene;methanol Chemical class OC.C1CCC=CC1 JMTOWIGWAQDRBE-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 32
- -1 5-substituted resorcinol Chemical class 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- XMKIECVHJJJPDQ-UHFFFAOYSA-N 2-(4-methoxycyclohexa-1,4-dien-1-yl)propan-2-ol Chemical compound COC1=CCC(C(C)(C)O)=CC1 XMKIECVHJJJPDQ-UHFFFAOYSA-N 0.000 claims 1
- RYLDHIKECAWTEK-UHFFFAOYSA-N 3-methoxy-5-(2-methyloctan-2-yl)phenol Chemical compound CCCCCCC(C)(C)C1=CC(O)=CC(OC)=C1 RYLDHIKECAWTEK-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- PTWFEJFERQFMAX-UHFFFAOYSA-N 1-ethoxy-6,6-dimethyl-7,8,10,10a-tetrahydro-6ah-benzo[c]chromen-9-one Chemical class O1C(C)(C)C2CCC(=O)CC2C2=C1C=CC=C2OCC PTWFEJFERQFMAX-UHFFFAOYSA-N 0.000 abstract 1
- VBIKLMJHBGFTPV-UHFFFAOYSA-N 3-ethoxyphenol Chemical compound CCOC1=CC=CC(O)=C1 VBIKLMJHBGFTPV-UHFFFAOYSA-N 0.000 abstract 1
- 238000007257 deesterification reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical class C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010028813 Nausea Diseases 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000008693 nausea Effects 0.000 description 4
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 2
- 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 2
- MWWIDYNYLZQEQP-UHFFFAOYSA-N 3-methoxy-5-pentylphenol Chemical compound CCCCCC1=CC(O)=CC(OC)=C1 MWWIDYNYLZQEQP-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- GECBBEABIDMGGL-RTBURBONSA-N nabilone Chemical compound C1C(=O)CC[C@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@@H]21 GECBBEABIDMGGL-RTBURBONSA-N 0.000 description 2
- 229960002967 nabilone Drugs 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- XBYKJURLZXSZII-UHFFFAOYSA-N 2-ethoxy-5-octylphenol Chemical compound C(C)OC1=C(C=C(C=C1)CCCCCCCC)O XBYKJURLZXSZII-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- ZEVPGIMZVLSBLY-UHFFFAOYSA-N 3-(cyclohexen-1-yl)-5-methoxyphenol Chemical compound COC1=CC(O)=CC(C=2CCCCC=2)=C1 ZEVPGIMZVLSBLY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PHOBVERAPLEAOA-UHFFFAOYSA-N 3-cyclohept-2-en-1-yl-5-methoxyphenol Chemical compound COC1=CC(O)=CC(C2C=CCCCC2)=C1 PHOBVERAPLEAOA-UHFFFAOYSA-N 0.000 description 1
- ZFDHQCPQRWMMSM-UHFFFAOYSA-N 3-cycloheptyl-5-ethoxyphenol Chemical compound CCOC1=CC(O)=CC(C2CCCCCC2)=C1 ZFDHQCPQRWMMSM-UHFFFAOYSA-N 0.000 description 1
- CDSXUTKQLPUSCB-UHFFFAOYSA-N 3-cyclohexyl-5-ethoxyphenol Chemical compound CCOC1=CC(O)=CC(C2CCCCC2)=C1 CDSXUTKQLPUSCB-UHFFFAOYSA-N 0.000 description 1
- MLWJZJMXRCGITG-UHFFFAOYSA-N 3-cyclooctyl-5-methoxyphenol Chemical compound COC1=CC(O)=CC(C2CCCCCCC2)=C1 MLWJZJMXRCGITG-UHFFFAOYSA-N 0.000 description 1
- LCSGWGFNPIQQIG-UHFFFAOYSA-N 3-dec-7-en-3-yl-5-ethoxyphenol Chemical compound CCOC1=CC(O)=CC(C(CC)CCCC=CCC)=C1 LCSGWGFNPIQQIG-UHFFFAOYSA-N 0.000 description 1
- BJKOWQIXKSLEJH-UHFFFAOYSA-N 3-decyl-5-methoxyphenol Chemical compound CCCCCCCCCCC1=CC(O)=CC(OC)=C1 BJKOWQIXKSLEJH-UHFFFAOYSA-N 0.000 description 1
- JZFMXUIZAHCDGM-UHFFFAOYSA-N 3-ethoxy-5-(2-methylheptan-2-yl)phenol Chemical compound CCCCCC(C)(C)C1=CC(O)=CC(OCC)=C1 JZFMXUIZAHCDGM-UHFFFAOYSA-N 0.000 description 1
- JKUCRSJSJWSGDR-UHFFFAOYSA-N 3-hex-3-enyl-5-methoxyphenol Chemical compound CCC=CCCC1=CC(O)=CC(OC)=C1 JKUCRSJSJWSGDR-UHFFFAOYSA-N 0.000 description 1
- ZKLHUKDDRUCGEG-UHFFFAOYSA-N 3-methoxy-5-(2-methyloct-5-en-2-yl)phenol Chemical compound CCC=CCCC(C)(C)C1=CC(O)=CC(OC)=C1 ZKLHUKDDRUCGEG-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SEQIMZPSZATKQD-UHFFFAOYSA-N benzo[c]chromen-9-one Chemical compound C1=CC=C2C3=CC(=O)C=CC3=COC2=C1 SEQIMZPSZATKQD-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003560 cancer drug Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- LJJVZJSGXHJIPP-UHFFFAOYSA-N ethylpentyl Chemical group [CH2+]CCC[CH]C[CH2-] LJJVZJSGXHJIPP-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 239000003960 organic solvent Substances 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US381,111 | 1982-05-24 | ||
| US06/381,111 US4395560A (en) | 1982-05-24 | 1982-05-24 | Preparation of 6a,10a-trans-hexahydrodibenzopyranones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1188702A true CA1188702A (en) | 1985-06-11 |
Family
ID=23503705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000427823A Expired CA1188702A (en) | 1982-05-24 | 1983-05-10 | Preparation of 6a,10a-trans-hexahydrodibenzopyranones |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4395560A (enExample) |
| EP (1) | EP0096480B1 (enExample) |
| JP (1) | JPS58210079A (enExample) |
| KR (1) | KR860001030B1 (enExample) |
| CA (1) | CA1188702A (enExample) |
| DE (1) | DE3378119D1 (enExample) |
| DK (1) | DK210083A (enExample) |
| GB (1) | GB2121038B (enExample) |
| GR (1) | GR79272B (enExample) |
| HU (1) | HU193651B (enExample) |
| IE (1) | IE55184B1 (enExample) |
| IL (1) | IL68626A (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2340445A1 (en) * | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Novel analgesic and immunomodulatory cannabinoids |
| US7897598B2 (en) * | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
| US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
| US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| EP1223808B1 (en) | 1999-10-18 | 2007-03-07 | The University Of Connecticut | Peripheral cannabinoid receptor (cb2) selective ligands |
| US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| US6943266B1 (en) * | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| US7119108B1 (en) * | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US6900236B1 (en) * | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| JP2004532185A (ja) * | 2001-01-26 | 2004-10-21 | ユニバーシティ オブ コネチカット | 新規なカンナビミメティックリガンド |
| ATE478670T1 (de) | 2001-01-29 | 2010-09-15 | Univ Connecticut | Rezeptor-selektive cannabimimetische aminoalkylindole |
| JP4312594B2 (ja) * | 2001-07-13 | 2009-08-12 | ユニバーシティ オブ コネチカット | 新規な二環式及び三環式カンナビノイド |
| CA2464333C (en) * | 2001-10-26 | 2011-07-26 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| JP2006511460A (ja) | 2002-08-23 | 2006-04-06 | ユニバーシティ オブ コネチカット | 治療適応を持つケトカンナビノイド |
| CA2638940C (en) * | 2008-08-28 | 2009-09-15 | Dalton Chemical Laboratories Inc. | Improved synthesis of hexahydrodibenzopyranones |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4054583A (en) * | 1976-07-06 | 1977-10-18 | Eli Lilly And Company | Process for converting 2,7-dihydroxy-5-isopropylidene-9-substituted-2,6-methano-3,4,5,6-tetrahydro-2H-1-benzoxocin to trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo(b,d)pyran-9-one |
| US4054582A (en) * | 1976-07-06 | 1977-10-18 | Eli Lilly And Company | Process for converting cis-hexahydrodibenzo[b,d]pyran-9-ones to trans-hexahydrodibenzo[b,d]-pyran-9-ones |
| CA1096390A (en) * | 1976-07-06 | 1981-02-24 | Edward R. Lavagnino | PROCESS FOR PREPARING DL-CIS-1-HYDROXY-3-SUBSTITUTED- 6,6-DIMETHYL-6,6.alpha.,7,8,10,10.alpha.-HEXAHYDRO-9H- DIBENZO(B,D,)PYRAN-9-ONES |
| PT66744B (en) * | 1976-07-06 | 1978-11-27 | Lilly Co Eli | Process for preparing cis-hexahydrodibenzopyranones |
| US4054581A (en) * | 1976-07-06 | 1977-10-18 | Eli Lilly And Company | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
| GB1582564A (en) * | 1976-07-06 | 1981-01-14 | Lilly Co Eli | Dibenzopyrans |
| US4171315A (en) * | 1978-03-31 | 1979-10-16 | Eli Lilly And Company | Preparation of cis-hexahydrodibenzopyranones |
-
1982
- 1982-05-24 US US06/381,111 patent/US4395560A/en not_active Expired - Lifetime
-
1983
- 1983-05-09 IL IL68626A patent/IL68626A/xx unknown
- 1983-05-10 CA CA000427823A patent/CA1188702A/en not_active Expired
- 1983-05-11 DK DK210083A patent/DK210083A/da not_active Application Discontinuation
- 1983-05-12 JP JP58083965A patent/JPS58210079A/ja active Pending
- 1983-05-13 IE IE1115/83A patent/IE55184B1/en unknown
- 1983-05-16 KR KR1019830002130A patent/KR860001030B1/ko not_active Expired
- 1983-05-16 EP EP83302745A patent/EP0096480B1/en not_active Expired
- 1983-05-16 HU HU831705A patent/HU193651B/hu not_active IP Right Cessation
- 1983-05-16 DE DE8383302745T patent/DE3378119D1/de not_active Expired
- 1983-05-16 GB GB08313470A patent/GB2121038B/en not_active Expired
- 1983-05-20 GR GR71411A patent/GR79272B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58210079A (ja) | 1983-12-07 |
| DK210083A (da) | 1983-11-25 |
| GB2121038B (en) | 1986-01-22 |
| GB2121038A (en) | 1983-12-14 |
| HU193651B (en) | 1987-11-30 |
| EP0096480B1 (en) | 1988-09-28 |
| KR860001030B1 (ko) | 1986-07-28 |
| GR79272B (enExample) | 1984-05-20 |
| IE831115L (en) | 1983-11-24 |
| EP0096480A3 (en) | 1985-04-03 |
| GB8313470D0 (en) | 1983-06-22 |
| US4395560A (en) | 1983-07-26 |
| IE55184B1 (en) | 1990-06-20 |
| IL68626A0 (en) | 1983-09-30 |
| KR840004737A (ko) | 1984-10-24 |
| DK210083D0 (da) | 1983-05-11 |
| DE3378119D1 (en) | 1988-11-03 |
| EP0096480A2 (en) | 1983-12-21 |
| IL68626A (en) | 1986-12-31 |
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