IE45244B1 - Dibenzopyrans - Google Patents
DibenzopyransInfo
- Publication number
- IE45244B1 IE45244B1 IE1386/77A IE138677A IE45244B1 IE 45244 B1 IE45244 B1 IE 45244B1 IE 1386/77 A IE1386/77 A IE 1386/77A IE 138677 A IE138677 A IE 138677A IE 45244 B1 IE45244 B1 IE 45244B1
- Authority
- IE
- Ireland
- Prior art keywords
- temperature
- catalyst
- stannic chloride
- hydroxy
- cis
- Prior art date
Links
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims abstract description 38
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 229910015900 BF3 Inorganic materials 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 77
- 230000008569 process Effects 0.000 claims description 77
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- -1 5-substituted resorcinol Chemical class 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000008282 halocarbons Chemical group 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 16
- 208000019901 Anxiety disease Diseases 0.000 abstract description 3
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 abstract 1
- 208000020401 Depressive disease Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 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 3
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- HUEHIFDXCQVLCS-UHFFFAOYSA-N 5-hex-1-enylbenzene-1,3-diol Chemical compound CCCCC=CC1=CC(O)=CC(O)=C1 HUEHIFDXCQVLCS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- ZKIQRMWOUDMWPY-UHFFFAOYSA-N 2-cyclohexa-1,4-dien-1-ylpropan-2-ol Chemical compound OC(C)(C)C1=CCC=CC1 ZKIQRMWOUDMWPY-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- CBPPEIBCFZIYIM-UHFFFAOYSA-N 5-(2-methylnonan-2-yl)benzene-1,3-diol Chemical compound CCCCCCCC(C)(C)C1=CC(O)=CC(O)=C1 CBPPEIBCFZIYIM-UHFFFAOYSA-N 0.000 description 1
- UBZGVGUDCNTZJA-UHFFFAOYSA-N 5-(3-ethylheptan-2-yl)benzene-1,3-diol Chemical compound CCCCC(CC)C(C)C1=CC(O)=CC(O)=C1 UBZGVGUDCNTZJA-UHFFFAOYSA-N 0.000 description 1
- LFAMTYOOZUPASP-UHFFFAOYSA-N 5-(3-methyloctan-2-yl)benzene-1,3-diol Chemical compound CCCCCC(C)C(C)C1=CC(O)=CC(O)=C1 LFAMTYOOZUPASP-UHFFFAOYSA-N 0.000 description 1
- FMABKTBGUKQFST-UHFFFAOYSA-N 5-(cyclohexen-1-yl)benzene-1,3-diol Chemical compound OC1=CC(O)=CC(C=2CCCCC=2)=C1 FMABKTBGUKQFST-UHFFFAOYSA-N 0.000 description 1
- NEGLHDOUROHUAQ-UHFFFAOYSA-N 5-(cyclopenten-1-yl)benzene-1,3-diol Chemical compound OC1=CC(O)=CC(C=2CCCC=2)=C1 NEGLHDOUROHUAQ-UHFFFAOYSA-N 0.000 description 1
- DEAIBPKVGVMMBW-UHFFFAOYSA-N 5-cyclohept-2-en-1-ylbenzene-1,3-diol Chemical compound OC1=CC(O)=CC(C2C=CCCCC2)=C1 DEAIBPKVGVMMBW-UHFFFAOYSA-N 0.000 description 1
- HMQGWKCZZHQLEF-UHFFFAOYSA-N 5-cycloheptylbenzene-1,3-diol Chemical compound OC1=CC(O)=CC(C2CCCCCC2)=C1 HMQGWKCZZHQLEF-UHFFFAOYSA-N 0.000 description 1
- OHKGJINKTSLQLP-UHFFFAOYSA-N 5-cyclohexylbenzene-1,3-diol Chemical compound OC1=CC(O)=CC(C2CCCCC2)=C1 OHKGJINKTSLQLP-UHFFFAOYSA-N 0.000 description 1
- RQZYGOASPHVIKK-UHFFFAOYSA-N 5-cyclooct-2-en-1-ylbenzene-1,3-diol Chemical compound OC1=CC(O)=CC(C2C=CCCCCC2)=C1 RQZYGOASPHVIKK-UHFFFAOYSA-N 0.000 description 1
- JQXLFGPGLOEPOA-UHFFFAOYSA-N 5-cyclopentylbenzene-1,3-diol Chemical compound OC1=CC(O)=CC(C2CCCC2)=C1 JQXLFGPGLOEPOA-UHFFFAOYSA-N 0.000 description 1
- SLRBBQYNLOLGFV-UHFFFAOYSA-N 5-dec-4-en-3-ylbenzene-1,3-diol Chemical compound CCCCCC=CC(CC)C1=CC(O)=CC(O)=C1 SLRBBQYNLOLGFV-UHFFFAOYSA-N 0.000 description 1
- XECRVULUEJSGBY-UHFFFAOYSA-N 5-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=CC(O)=CC(O)=C1 XECRVULUEJSGBY-UHFFFAOYSA-N 0.000 description 1
- MLTDAQBMPDSTEO-UHFFFAOYSA-N 5-oct-1-enylbenzene-1,3-diol Chemical compound CCCCCCC=CC1=CC(O)=CC(O)=C1 MLTDAQBMPDSTEO-UHFFFAOYSA-N 0.000 description 1
- TUJIXDOPKBTCBL-UHFFFAOYSA-N 5-octylbenzene-1,3-diol Chemical compound CCCCCCCCC1=CC(O)=CC(O)=C1 TUJIXDOPKBTCBL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000049 anti-anxiety effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- NMGSDTSOSIPXTN-UHFFFAOYSA-N cyclohexa-1,2-diene Chemical compound C1CC=C=CC1 NMGSDTSOSIPXTN-UHFFFAOYSA-N 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
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- QYQIKTBQNRWCEW-UHFFFAOYSA-K dichlorosyloxyalumanyl chlorite Chemical compound [Al+3].[O-]Cl=O.[O-]Cl=O.[O-]Cl=O QYQIKTBQNRWCEW-UHFFFAOYSA-K 0.000 description 1
- NNOGMCQLKMLNPL-UHFFFAOYSA-N diethyl 2-acetylpentanedioate Chemical compound CCOC(=O)CCC(C(C)=O)C(=O)OCC NNOGMCQLKMLNPL-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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)
- Pyrane Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70280976A | 1976-07-06 | 1976-07-06 | |
| US70280676A | 1976-07-06 | 1976-07-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE45244L IE45244L (en) | 1978-01-06 |
| IE45244B1 true IE45244B1 (en) | 1982-07-14 |
Family
ID=27107024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1386/77A IE45244B1 (en) | 1976-07-06 | 1977-07-05 | Dibenzopyrans |
Country Status (22)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4171315A (en) * | 1978-03-31 | 1979-10-16 | Eli Lilly And Company | Preparation of cis-hexahydrodibenzopyranones |
| US4395560A (en) * | 1982-05-24 | 1983-07-26 | Eli Lilly And Company | Preparation of 6a,10a-trans-hexahydrodibenzopyranones |
| CA2638940C (en) * | 2008-08-28 | 2009-09-15 | Dalton Chemical Laboratories Inc. | Improved synthesis of hexahydrodibenzopyranones |
-
1977
- 1977-06-29 GB GB27112/77A patent/GB1582564A/en not_active Expired
- 1977-06-30 SE SE7707631A patent/SE428018B/xx not_active IP Right Cessation
- 1977-06-30 IL IL52425A patent/IL52425A/xx unknown
- 1977-06-30 NZ NZ184528A patent/NZ184528A/xx unknown
- 1977-07-01 BG BG036780A patent/BG28063A3/xx unknown
- 1977-07-01 YU YU01634/77A patent/YU163477A/xx unknown
- 1977-07-01 AU AU26682/77A patent/AU511627B2/en not_active Expired
- 1977-07-01 DE DE2729817A patent/DE2729817C2/de not_active Expired
- 1977-07-04 CH CH819177A patent/CH633786A5/de not_active IP Right Cessation
- 1977-07-04 SU SU772499310A patent/SU772483A3/ru active
- 1977-07-04 PL PL1977199361A patent/PL108319B1/pl unknown
- 1977-07-04 JP JP52081486A patent/JPS5943466B2/ja not_active Expired
- 1977-07-04 AR AR268308A patent/AR213440A1/es active
- 1977-07-05 DD DD7700199897A patent/DD131469A5/xx unknown
- 1977-07-05 DK DK301377A patent/DK145100C/da not_active IP Right Cessation
- 1977-07-05 HU HU77EI753A patent/HU176954B/hu unknown
- 1977-07-05 IE IE1386/77A patent/IE45244B1/en unknown
- 1977-07-05 NL NL7707464A patent/NL7707464A/xx not_active Application Discontinuation
- 1977-07-05 GR GR53877A patent/GR66415B/el unknown
- 1977-07-05 FR FR7720642A patent/FR2357555A1/fr active Granted
- 1977-07-06 AT AT483477A patent/AT351531B/de not_active IP Right Cessation
- 1977-07-06 CS CS774516A patent/CS193580B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE428018B (sv) | 1983-05-30 |
| DK145100B (da) | 1982-08-30 |
| SU772483A3 (ru) | 1980-10-15 |
| DE2729817C2 (de) | 1982-05-27 |
| NL7707464A (nl) | 1978-01-10 |
| PL199361A1 (pl) | 1978-04-10 |
| GR66415B (enrdf_load_stackoverflow) | 1981-03-20 |
| DK145100C (da) | 1983-01-31 |
| DK301377A (da) | 1978-01-07 |
| GB1582564A (en) | 1981-01-14 |
| JPS537678A (en) | 1978-01-24 |
| AT351531B (de) | 1979-07-25 |
| HU176954B (hu) | 1981-06-28 |
| JPS5943466B2 (ja) | 1984-10-22 |
| AU511627B2 (en) | 1980-08-28 |
| YU163477A (en) | 1982-06-30 |
| AU2668277A (en) | 1979-01-04 |
| FR2357555B1 (enrdf_load_stackoverflow) | 1980-02-01 |
| AR213440A1 (es) | 1979-01-31 |
| CH633786A5 (en) | 1982-12-31 |
| CS193580B2 (en) | 1979-10-31 |
| IL52425A0 (en) | 1977-08-31 |
| IL52425A (en) | 1980-09-16 |
| NZ184528A (en) | 1978-09-20 |
| PL108319B1 (en) | 1980-04-30 |
| BG28063A3 (en) | 1980-02-25 |
| FR2357555A1 (fr) | 1978-02-03 |
| ATA483477A (de) | 1979-01-15 |
| DE2729817A1 (de) | 1978-01-12 |
| SE7707631L (sv) | 1978-01-07 |
| DD131469A5 (de) | 1978-06-28 |
| IE45244L (en) | 1978-01-06 |
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