CS196376B2 - Method for the stereoselective production of optical isomers of hexahydrodibenzopyranone derivatives - Google Patents
Method for the stereoselective production of optical isomers of hexahydrodibenzopyranone derivatives Download PDFInfo
- Publication number
- CS196376B2 CS196376B2 CS774518A CS451877A CS196376B2 CS 196376 B2 CS196376 B2 CS 196376B2 CS 774518 A CS774518 A CS 774518A CS 451877 A CS451877 A CS 451877A CS 196376 B2 CS196376 B2 CS 196376B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- dimethyl
- reaction
- trans
- cis
- Prior art date
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 27
- 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 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 230000000707 stereoselective effect Effects 0.000 title claims 2
- -1 4-(4-substituted-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone Chemical class 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000002841 Lewis acid Substances 0.000 claims abstract description 7
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 235000011150 stannous chloride Nutrition 0.000 claims description 5
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- YFJDGZZRPOYOFP-UHFFFAOYSA-N (4-acetyloxy-6,6-dimethyl-2-bicyclo[3.1.1]hept-3-enyl) acetate Chemical compound CC(=O)OC1C=C(OC(C)=O)C2C(C)(C)C1C2 YFJDGZZRPOYOFP-UHFFFAOYSA-N 0.000 abstract description 2
- TUJQDYIBTVJMMM-UHFFFAOYSA-N (4-acetyloxy-6,6-dimethyl-4-bicyclo[3.1.1]hept-2-enyl) acetate Chemical compound CC(=O)OC1(OC(C)=O)C=CC2C(C)(C)C1C2 TUJQDYIBTVJMMM-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001591 beta-pinene derivatives Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 208000019901 Anxiety disease Diseases 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 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 3
- 241000124008 Mammalia Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- PBVMIPXCKZYJMA-UHFFFAOYSA-N bicyclo[3.1.1]hept-4-ene Chemical compound C1C2=CCCC1C2 PBVMIPXCKZYJMA-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CZQBNTFHWGYINW-UHFFFAOYSA-N (4-acetyloxy-2-bicyclo[3.1.1]hept-4-enyl) acetate Chemical class CC(=O)OC1CC(OC(C)=O)=C2CC1C2 CZQBNTFHWGYINW-UHFFFAOYSA-N 0.000 description 1
- KRDHHMGOAHHUPH-UHFFFAOYSA-N (4-acetyloxy-4-bicyclo[3.1.1]hept-2-enyl) acetate Chemical compound CC(=O)OC1(OC(C)=O)C=CC2CC1C2 KRDHHMGOAHHUPH-UHFFFAOYSA-N 0.000 description 1
- XMHXPSAHLRZYKH-JOYOIKCWSA-N (4aR,6aR)-2,3,4,4a,6,6a-hexahydrobenzo[c]chromen-1-one Chemical compound C1=CC=CC2=C3C(=O)CCC[C@H]3OC[C@@H]21 XMHXPSAHLRZYKH-JOYOIKCWSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- NBQYFMKBZLSPIY-UHFFFAOYSA-N 3,4,4a,5,6,7-hexahydrochromen-2-one Chemical compound C1CCC=C2OC(=O)CCC21 NBQYFMKBZLSPIY-UHFFFAOYSA-N 0.000 description 1
- ICBZSKCTKKUQSY-YUWZRIFDSA-N 4-[(1r,2s)-1-hydroxy-2-(methylamino)propyl]phenol;hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 ICBZSKCTKKUQSY-YUWZRIFDSA-N 0.000 description 1
- KBOQXVVZFSWICE-FIJLXMTKSA-N 5-[(8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-1,2,7,8,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one Chemical compound C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CCC=CC5=CC4)C)CC[C@@]32C)C=CC(=O)OC=1 KBOQXVVZFSWICE-FIJLXMTKSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003556 assay Methods 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
- SHOMMGQAMRXRRK-UHFFFAOYSA-N bicyclo[3.1.1]heptane Chemical group C1C2CC1CCC2 SHOMMGQAMRXRRK-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS782081A CS196377B2 (cs) | 1976-11-10 | 1978-03-31 | Způsob výroby opticky aktivních derivátů norpinenu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/740,502 US4102902A (en) | 1976-11-10 | 1976-11-10 | Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196376B2 true CS196376B2 (en) | 1980-03-31 |
Family
ID=24976773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS774518A CS196376B2 (en) | 1976-11-10 | 1977-07-06 | Method for the stereoselective production of optical isomers of hexahydrodibenzopyranone derivatives |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4102902A (en, 2012) |
| JP (2) | JPS5925792B2 (en, 2012) |
| AT (1) | AT356103B (en, 2012) |
| AU (1) | AU509355B2 (en, 2012) |
| BE (1) | BE856413A (en, 2012) |
| BG (2) | BG28061A3 (en, 2012) |
| CA (1) | CA1101875A (en, 2012) |
| CH (2) | CH632506A5 (en, 2012) |
| CS (1) | CS196376B2 (en, 2012) |
| DD (2) | DD140455A5 (en, 2012) |
| DE (3) | DE2760006C2 (en, 2012) |
| DK (1) | DK301477A (en, 2012) |
| ES (3) | ES460387A1 (en, 2012) |
| FR (1) | FR2370742A1 (en, 2012) |
| GB (2) | GB1584182A (en, 2012) |
| GR (1) | GR66417B (en, 2012) |
| HU (2) | HU183286B (en, 2012) |
| IE (1) | IE45247B1 (en, 2012) |
| IL (3) | IL52427A (en, 2012) |
| MX (1) | MX5172E (en, 2012) |
| NL (1) | NL7707467A (en, 2012) |
| NZ (1) | NZ184526A (en, 2012) |
| PH (3) | PH13827A (en, 2012) |
| PL (2) | PL104432B1 (en, 2012) |
| PT (1) | PT66746B (en, 2012) |
| RO (1) | RO78780A (en, 2012) |
| SE (3) | SE428020B (en, 2012) |
| SU (2) | SU786898A3 (en, 2012) |
| YU (1) | YU163677A (en, 2012) |
| ZA (1) | ZA773960B (en, 2012) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL55274A (en) * | 1978-08-02 | 1982-08-31 | Yissum Res Dev Co | 4-(2,6-dihydroxy-4-(dimethylheptyl)phenyl)substituted 2-pinen-10-ol and pinane derivatives,their preparation and pharmaceutical compositions comprising them |
| US4939169A (en) * | 1985-09-20 | 1990-07-03 | The Upjohn Company | 1,4-naphthalenediol and 1,4-hydroquinone derivatives |
| JPS63501288A (ja) * | 1985-09-20 | 1988-05-19 | ジ・アップジョン・カンパニ− | １，４−ナフタレンジオ−ルおよび１，４−ヒドロキノン誘導体 |
| IL80411A (en) * | 1986-10-24 | 1991-08-16 | Raphael Mechoulam | Preparation of dibenzopyranol derivatives and pharmaceutical compositions containing them |
| JPH0315035A (ja) * | 1989-03-03 | 1991-01-23 | Konica Corp | カメラ |
| JP2577671B2 (ja) * | 1990-06-11 | 1997-02-05 | 高砂熱学工業株式会社 | 気化式精密加湿装置 |
| ATE247097T1 (de) * | 1998-05-04 | 2003-08-15 | Univ Connecticut | Analgetische und immunomodulierende cannabinoiden |
| US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| US7897598B2 (en) * | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | 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 |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| DE60033545T2 (de) * | 1999-10-18 | 2007-10-31 | The University Of Connecticut, Farmington | Neue bizyklische cannabinoid-agonisten für den cannabinoid-rezeptor |
| US7119108B1 (en) * | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US6943266B1 (en) * | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| 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 |
| US6900236B1 (en) * | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| EP1361876A4 (en) * | 2001-01-26 | 2004-03-31 | Univ Connecticut | NEW CANNABIMIMETIC LIGANDS |
| JP2005503998A (ja) | 2001-01-29 | 2005-02-10 | ユニバーシティ オブ コネチカット | 受容体選択性のカンナビミメティックアミノアルキルインドール |
| 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 |
| JP2005510492A (ja) * | 2001-10-26 | 2005-04-21 | ユニバーシティ オブ コネチカット | 新規な種類の効力のあるカンナビミメティックリガンド |
| WO2003091189A1 (en) * | 2002-04-25 | 2003-11-06 | Virginia Commonwealth University | Cannabinoids |
| WO2004017922A2 (en) | 2002-08-23 | 2004-03-04 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
| EP2578577A1 (en) * | 2005-09-29 | 2013-04-10 | Albany Molecular Research, Inc. | Sulfonyl esters of tetrahydrocannabinol and derivatives thereof |
| US9763894B2 (en) * | 2006-12-05 | 2017-09-19 | Virginia Commonwealth University | Inflammation therapy |
| PL222532B1 (pl) | 2012-04-05 | 2016-08-31 | Akademia Morska W Szczecinie | Sposób i układ do diagnozowania układu wtryskowego silników o zapłonie samoczynnym, zwłaszcza silników okrętowych |
| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856822A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | 3-alkenyl dibenzo (b,d)pyrans |
| US3856820A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | 2-AMINOMETHYL DIBENZO (b,d) PYRANS |
| US3856821A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | ALKOXY DIBENZO (b,d) PYRANS |
| US3928598A (en) * | 1973-11-05 | 1975-12-23 | Lilly Co Eli | Hexahydro-dibenzo{8 b,d{9 pyran-9-ones as an anti-anxiety drug |
-
1976
- 1976-11-10 US US05/740,502 patent/US4102902A/en not_active Expired - Lifetime
-
1977
- 1977-06-29 GB GB1144/80A patent/GB1584182A/en not_active Expired
- 1977-06-29 GB GB27138/77A patent/GB1584181A/en not_active Expired
- 1977-06-30 CA CA281,784A patent/CA1101875A/en not_active Expired
- 1977-06-30 NZ NZ184526A patent/NZ184526A/xx unknown
- 1977-06-30 ZA ZA00773960A patent/ZA773960B/xx unknown
- 1977-06-30 SE SE7707633A patent/SE428020B/xx not_active IP Right Cessation
- 1977-06-30 PH PH19935A patent/PH13827A/en unknown
- 1977-06-30 PT PT66746A patent/PT66746B/pt unknown
- 1977-06-30 IL IL52427A patent/IL52427A/xx unknown
- 1977-07-01 YU YU01636/77A patent/YU163677A/xx unknown
- 1977-07-01 BG BG036778A patent/BG28061A3/xx unknown
- 1977-07-01 BG BG037819A patent/BG28411A4/xx unknown
- 1977-07-01 DE DE2760006A patent/DE2760006C2/de not_active Expired
- 1977-07-01 AU AU26684/77A patent/AU509355B2/en not_active Expired
- 1977-07-01 DE DE2729859A patent/DE2729859C2/de not_active Expired
- 1977-07-01 DE DE2760005A patent/DE2760005C2/de not_active Expired
- 1977-07-04 JP JP52081489A patent/JPS5925792B2/ja not_active Expired
- 1977-07-04 ES ES460387A patent/ES460387A1/es not_active Expired
- 1977-07-04 SU SU772497362A patent/SU786898A3/ru active
- 1977-07-04 ES ES460389A patent/ES460389A1/es not_active Expired
- 1977-07-04 BE BE1008247A patent/BE856413A/xx not_active IP Right Cessation
- 1977-07-04 CH CH819477A patent/CH632506A5/de not_active IP Right Cessation
- 1977-07-04 PL PL1977206420A patent/PL104432B1/pl unknown
- 1977-07-04 ES ES460388A patent/ES460388A1/es not_active Expired
- 1977-07-04 MX MX775872U patent/MX5172E/es unknown
- 1977-07-04 PL PL1977199362A patent/PL104356B1/pl unknown
- 1977-07-05 GR GR53879A patent/GR66417B/el unknown
- 1977-07-05 IE IE1389/77A patent/IE45247B1/en unknown
- 1977-07-05 HU HU81113A patent/HU183286B/hu unknown
- 1977-07-05 HU HU77EI755A patent/HU177308B/hu unknown
- 1977-07-05 DD DD77208796A patent/DD140455A5/de unknown
- 1977-07-05 RO RO7798966A patent/RO78780A/ro unknown
- 1977-07-05 DK DK301477A patent/DK301477A/da not_active Application Discontinuation
- 1977-07-05 DD DD77199899A patent/DD134350A5/xx unknown
- 1977-07-05 FR FR7720645A patent/FR2370742A1/fr active Granted
- 1977-07-05 NL NL7707467A patent/NL7707467A/xx not_active Application Discontinuation
- 1977-07-06 AT AT483677A patent/AT356103B/de not_active IP Right Cessation
- 1977-07-06 CS CS774518A patent/CS196376B2/cs unknown
- 1977-10-28 PH PH20381A patent/PH13890A/en unknown
- 1977-10-28 PH PH20382A patent/PH14708A/en unknown
-
1978
- 1978-07-06 SU SU782633652A patent/SU1128829A3/ru active
-
1980
- 1980-07-15 IL IL60590A patent/IL60590A0/xx unknown
- 1980-07-15 IL IL60589A patent/IL60589A0/xx unknown
- 1980-07-22 SE SE8005314A patent/SE8005314L/sv not_active Application Discontinuation
- 1980-07-22 SE SE8005316A patent/SE434510B/sv unknown
-
1982
- 1982-02-05 CH CH71882A patent/CH632481A5/de not_active IP Right Cessation
- 1982-04-16 JP JP57064621A patent/JPS5912654B2/ja not_active Expired
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