HU193651B - Process for producing 6a, 10a-trans-hexahydro-dibenzo-pyranone derivatives - Google Patents
Process for producing 6a, 10a-trans-hexahydro-dibenzo-pyranone derivatives Download PDFInfo
- Publication number
- HU193651B HU193651B HU831705A HU170583A HU193651B HU 193651 B HU193651 B HU 193651B HU 831705 A HU831705 A HU 831705A HU 170583 A HU170583 A HU 170583A HU 193651 B HU193651 B HU 193651B
- Authority
- HU
- Hungary
- Prior art keywords
- trans
- hexahydro
- reaction
- methoxy
- dibenzo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- -1 5-substituted resorcinol Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 description 2
- 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 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- JMTOWIGWAQDRBE-UHFFFAOYSA-N cyclohexene;methanol Chemical class OC.C1CCC=CC1 JMTOWIGWAQDRBE-UHFFFAOYSA-N 0.000 abstract description 2
- 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 12
- 150000001875 compounds Chemical class 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 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 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 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
- 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
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical class C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229960002967 nabilone Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010028813 Nausea Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000008693 nausea Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YLMWDSLFJDMXIU-UHFFFAOYSA-N 2-(4-butoxycyclohexa-1,4-dien-1-yl)propan-2-ol Chemical compound CCCCOC1=CCC(C(C)(C)O)=CC1 YLMWDSLFJDMXIU-UHFFFAOYSA-N 0.000 description 1
- FIYBVKKMZRGMCO-UHFFFAOYSA-N 2-(4-ethoxycyclohexa-1,4-dien-1-yl)propan-2-ol Chemical compound CCOC1=CCC(C(C)(C)O)=CC1 FIYBVKKMZRGMCO-UHFFFAOYSA-N 0.000 description 1
- NYKMRKNTESSVPT-UHFFFAOYSA-N 2-(4-propan-2-yloxycyclohexa-1,4-dien-1-yl)propan-2-ol Chemical compound CC(C)OC1=CCC(C(C)(C)O)=CC1 NYKMRKNTESSVPT-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
- MCQMRGXDWOPCJZ-UHFFFAOYSA-N 3-ethoxy-5-heptan-3-ylphenol Chemical compound CCCCC(CC)C1=CC(O)=CC(OCC)=C1 MCQMRGXDWOPCJZ-UHFFFAOYSA-N 0.000 description 1
- UIZLQTOVRARHJY-UHFFFAOYSA-N 3-ethoxy-5-octylphenol Chemical compound CCCCCCCCC1=CC(O)=CC(OCC)=C1 UIZLQTOVRARHJY-UHFFFAOYSA-N 0.000 description 1
- GUCHZXIUGZWJNI-UHFFFAOYSA-N 3-methoxy-5-(3-methyloctan-2-yl)phenol Chemical compound CCCCCC(C)C(C)C1=CC(O)=CC(OC)=C1 GUCHZXIUGZWJNI-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000001062 anti-nausea Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000003254 palate Anatomy 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005406 washing 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)
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/381,111 US4395560A (en) | 1982-05-24 | 1982-05-24 | Preparation of 6a,10a-trans-hexahydrodibenzopyranones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU193651B true HU193651B (en) | 1987-11-30 |
Family
ID=23503705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU831705A HU193651B (en) | 1982-05-24 | 1983-05-16 | Process for producing 6a, 10a-trans-hexahydro-dibenzo-pyranone derivatives |
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 |
| 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 |
| CA1188702A (en) | 1985-06-11 |
| IL68626A (en) | 1986-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |