CA1097370A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1097370A
Authority: CA; Canada
Prior art keywords: dimethyl; norpinanone; trans; hexahydro; optically active
Prior art date: 1976-11-10
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

Application number

CA354,413A

Other languages

English (en)

Inventor

Robert A. Archer

William A. Day

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

Priority date (The priority date 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 date listed.)

1976-11-10

Filing date

1980-06-19

Publication date

1981-03-10

1976-11-10 Priority claimed from US05/740,502 external-priority patent/US4102902A/en

1980-06-19 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1980-06-19 Priority to CA354,413A priority Critical patent/CA1097370A/fr

1981-03-10 Application granted granted Critical

1981-03-10 Publication of CA1097370A publication Critical patent/CA1097370A/fr

Status Expired legal-status Critical Current

Links

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 description 8
239000000543 intermediate Substances 0.000 title description 8
238000002360 preparation method Methods 0.000 title description 7
230000000707 stereoselective effect Effects 0.000 title 1
-1 4-(4-substituted-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone Chemical class 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 21
230000008569 process Effects 0.000 claims abstract description 16
239000011541 reaction mixture Substances 0.000 claims description 18
239000003960 organic solvent Substances 0.000 claims description 11
XZFDKWMYCUEKSS-UHFFFAOYSA-N 6,6-Dimethylbicyclo[3.1.1]heptan-2-one Chemical compound C1C2C(C)(C)C1CCC2=O XZFDKWMYCUEKSS-UHFFFAOYSA-N 0.000 claims description 9
238000010992 reflux Methods 0.000 claims description 8
JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims description 7
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
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 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
150000002085 enols Chemical class 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 abstract description 30
150000001875 compounds Chemical class 0.000 abstract description 20
239000002253 acid Substances 0.000 abstract description 19
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 11
230000003287 optical effect Effects 0.000 abstract description 10
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 10
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 8
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
239000000047 product Substances 0.000 description 51
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 39
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
239000002904 solvent Substances 0.000 description 18
238000001704 evaporation Methods 0.000 description 16
230000008020 evaporation Effects 0.000 description 16
239000003921 oil Substances 0.000 description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
239000012044 organic layer Substances 0.000 description 13
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 12
FNTPCMPJXYNWGS-UHFFFAOYSA-N 2-[2,6-dihydroxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC(O)=C1C1C(C2(C)C)CC2C(=O)C1 FNTPCMPJXYNWGS-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
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 7
239000002841 Lewis acid Substances 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 7
230000000694 effects Effects 0.000 description 7
150000007517 lewis acids Chemical class 0.000 description 7
VOXMSDBFCQUNDP-UHFFFAOYSA-N (4-acetyloxy-2-bicyclo[3.1.1]hept-3-enyl) acetate Chemical compound CC(=O)OC1C=C(OC(C)=O)C2CC1C2 VOXMSDBFCQUNDP-UHFFFAOYSA-N 0.000 description 6
229910015900 BF3 Inorganic materials 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
PBVMIPXCKZYJMA-UHFFFAOYSA-N bicyclo[3.1.1]hept-4-ene Chemical compound C1C2=CCCC1C2 PBVMIPXCKZYJMA-UHFFFAOYSA-N 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 5
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 5
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 4
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 4
ROVVOYDQNXKGHL-UHFFFAOYSA-N 2-(2,6-dihydroxy-4-pentylphenyl)-6,6-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound OC1=CC(CCCCC)=CC(O)=C1C1C(C2(C)C)CC2C(=O)C1 ROVVOYDQNXKGHL-UHFFFAOYSA-N 0.000 description 4
208000019901 Anxiety disease Diseases 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000036506 anxiety Effects 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000006260 foam Substances 0.000 description 4
IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 description 4
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 3
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
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
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 2
CVELEVINKSHGGZ-UHFFFAOYSA-N (4-acetyloxy-4-bicyclo[3.1.1]hept-5-enyl) acetate Chemical class CC(=O)OC1(OC(C)=O)CCC2C=C1C2 CVELEVINKSHGGZ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
230000036592 analgesia Effects 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
BAZWVAPEOUHZEW-UHFFFAOYSA-N (4-acetyloxy-3-bicyclo[3.1.1]hept-4-enyl) acetate Chemical class CC(=O)OC1CC(C2)CC2=C1OC(C)=O BAZWVAPEOUHZEW-UHFFFAOYSA-N 0.000 description 1
GECBBEABIDMGGL-RBUKOAKNSA-N (6ar,10as)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6ah-benzo[c]chromen-9-one Chemical compound C1C(=O)CC[C@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@H]21 GECBBEABIDMGGL-RBUKOAKNSA-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
125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
DQMGNYBUVKROBC-UHFFFAOYSA-N 2-(2,6-dihydroxy-4-non-4-enylphenyl)-6,6-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound OC1=CC(CCCC=CCCCC)=CC(O)=C1C1C(C2(C)C)CC2C(=O)C1 DQMGNYBUVKROBC-UHFFFAOYSA-N 0.000 description 1
JWLPNAQYDZMCCT-UHFFFAOYSA-N 2-(4-cyclohex-3-en-1-yl-2,6-dihydroxyphenyl)-6,6-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound CC1(C)C2CC1C(=O)CC2C(C(=C1)O)=C(O)C=C1C1CCC=CC1 JWLPNAQYDZMCCT-UHFFFAOYSA-N 0.000 description 1
FLZOOPMHGHHWOG-UHFFFAOYSA-N 2-(4-cyclohexyl-2,6-dihydroxyphenyl)-6,6-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound CC1(C)C2CC1C(=O)CC2C(C(=C1)O)=C(O)C=C1C1CCCCC1 FLZOOPMHGHHWOG-UHFFFAOYSA-N 0.000 description 1
UMVRWKIBYZNRAS-UHFFFAOYSA-N 2-(4-cyclooctyl-2,6-dihydroxyphenyl)-6,6-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound CC1(C)C2CC1C(=O)CC2C(C(=C1)O)=C(O)C=C1C1CCCCCCC1 UMVRWKIBYZNRAS-UHFFFAOYSA-N 0.000 description 1
JPEVXKVCPWKOLR-UHFFFAOYSA-N 2-(4-hex-3-enyl-2,6-dihydroxyphenyl)-6,6-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound OC1=CC(CCC=CCC)=CC(O)=C1C1C(C2(C)C)CC2C(=O)C1 JPEVXKVCPWKOLR-UHFFFAOYSA-N 0.000 description 1
SSORSZACHCNXSJ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NCC(C)O SSORSZACHCNXSJ-UHFFFAOYSA-N 0.000 description 1
VNJOEUSYAMPBAK-UHFFFAOYSA-N 2-methylbenzenesulfonic acid;hydrate Chemical compound O.CC1=CC=CC=C1S(O)(=O)=O VNJOEUSYAMPBAK-UHFFFAOYSA-N 0.000 description 1
125000006024 2-pentenyl group Chemical group 0.000 description 1
125000006041 3-hexenyl group Chemical group 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease 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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
SEQIMZPSZATKQD-UHFFFAOYSA-N benzo[c]chromen-9-one Chemical class C1=CC=C2C3=CC(=O)C=CC3=COC2=C1 SEQIMZPSZATKQD-UHFFFAOYSA-N 0.000 description 1
DEVHXDJLQMAWLM-UHFFFAOYSA-N bicyclo[3.1.1]hept-3-ene Chemical compound C1C2CC1CC=C2 DEVHXDJLQMAWLM-UHFFFAOYSA-N 0.000 description 1
PMAXNHPFNDQMAO-UHFFFAOYSA-N bicyclo[3.1.1]heptan-4-one Chemical compound O=C1CCC2CC1C2 PMAXNHPFNDQMAO-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000006482 condensation reaction Methods 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
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation 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
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
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
229960002967 nabilone Drugs 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA354,413A 1976-11-10 1980-06-19 Traduction non-disponible Expired CA1097370A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA354,413A CA1097370A (fr)	1976-11-10	1980-06-19	Traduction non-disponible

Applications Claiming Priority (4)

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
US740,502		1976-11-10
CA281,784A CA1101875A (fr)	1976-11-10	1977-06-30	Obtention stereo-selective d'hexahydrodibenzopyranones et de leurs intermediaires
CA354,413A CA1097370A (fr)	1976-11-10	1980-06-19	Traduction non-disponible

Publications (1)

Publication Number	Publication Date
CA1097370A true CA1097370A (fr)	1981-03-10

Family

ID=27165168

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA354,413A Expired CA1097370A (fr)	1976-11-10	1980-06-19	Traduction non-disponible

Country Status (1)

Country	Link
CA (1)	CA1097370A (fr)

1980
- 1980-06-19 CA CA354,413A patent/CA1097370A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-03-10	MKEX	Expiry

Publication	Publication Date	Title
CA1101875A (fr)	1981-05-26	Obtention stereo-selective d'hexahydrodibenzopyranones et de leurs intermediaires
US4208351A (en)	1980-06-17	Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
Huffman et al.	1999	3-(1′, 1′-Dimethylbutyl)-1-deoxy-Δ8-THC and related compounds: synthesis of selective ligands for the CB2 receptor
US4176233A (en)	1979-11-27	Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
Archer et al.	1977	Cannabinoids. 3. Synthetic approaches to 9-ketocannabinoids. Total synthesis of nabilone
EP0004753B1 (fr)	1982-05-26	Préparation de tétrahydrobenzoxocines et cis - hexahydrodibenzopyranones
CA1088082A (fr)	1980-10-21	Procede de conversion de cis-hexahydrodibenzo (b,d) pyran-9-ones en trans-hexahydrodibenzo (b,d) pyran-9- ones
Trifonov et al.	1983	Isolation and structure elucidation of three metabolites from Verticillium intertextum: sorbicillin, dihydrosorbicillin and bisvertinoquinol
EP0011928A1 (fr)	1980-06-11	Dérivés d'ester de l'acide 3.5-dihydroxypentanoique à activité antihyperlipémique, leur préparation et compositions pharmaceutiques les contenant
GB2174991A (en)	1986-11-19	Cyclodextrin complexes with dibenzo (bd)pyran derivatives and their preparation and pharmaceutical formulation
US3154565A (en)	1964-10-27	Chromenyl compounds and method of preparing
Banachowicz et al.	2019	Gram-scale carbasugar synthesis via intramolecular seleno-Michael/aldol reaction
HU184194B (en)	1984-07-30	Process for producing new ethers containing chiralic carbon atoms
House et al.	1961	Synthesis of Δ8, 9-and Δ9, 10-Octal-1-one1
Sato et al.	1979	New Synthesis of the Both Enantiomers of (Z)-5-(l-Decenyl)-oxacyclopentan-2-one, the Pheromone of the Japanese Beetle
CA1097370A (fr)	1981-03-10	Traduction non-disponible
US4140701A (en)	1979-02-20	2,6-Methano-2H-1-benzoxocins
GB2125397A (en)	1984-03-07	16-oxa-3-methylbicyclo (10.3.1) pentadec-1-ene
KR820000784B1 (ko)	1982-05-10	헥사하이드로-디벤조피라논 화합물의 광학적 이성체의 제조방법
US3004040A (en)	1961-10-10	Dimethoxy-1,2-chromenes
CA1090813A (fr)	1980-12-02	Obtention de cis-1-hydroxy-substitue en 3-6,6- dimethyl-6,6a-7,8,10,10a-hexahydro-9h-dibenzo ¬bd\| pyran-9-ones et de leurs intermediaires
US2566357A (en)	1951-09-04	Synthesis of di-aryl cyclic ethers
SU988817A1 (ru)	1983-01-15	Способ получени тетрагидрофуранов
US4075230A (en)	1978-02-21	Preparation of optically active trans-hexahydrodibenzopyranones
CA1122992A (fr)	1982-05-04	Benzocycloheptapyranes, substances qui en derivent et leur emploi