CA1100979A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1100979A
Authority: CA; Canada
Prior art keywords: hydroxy; ketal; dimethyl; pyran; dibenzo
Prior art date: 1976-07-06
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

CA356,593A

Other languages

English (en)

Inventor

William B. Blanchard

Charles W. Ryan

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.)

1976-07-06

Filing date

1980-07-18

Publication date

1981-05-12

1976-07-06 Priority claimed from US05/702,804 external-priority patent/US4054581A/en

1980-07-18 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1980-07-18 Priority to CA356,593A priority Critical patent/CA1100979A/fr

1981-05-12 Application granted granted Critical

1981-05-12 Publication of CA1100979A publication Critical patent/CA1100979A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 4
239000000543 intermediate Substances 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 15
238000004519 manufacturing process Methods 0.000 claims abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 8
-1 cyclohexenone carboxylate Chemical class 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
239000000126 substance Substances 0.000 claims 4
RCZLCLVMJHKZAJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)cyclohex-3-en-1-one Chemical compound CC(C)(O)C1=CCC(=O)CC1 RCZLCLVMJHKZAJ-UHFFFAOYSA-N 0.000 abstract description 2
230000000875 corresponding effect Effects 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Natural products OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
229940035437 1,3-propanediol Drugs 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-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
235000019270 ammonium chloride Nutrition 0.000 description 2
230000036506 anxiety Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
150000003509 tertiary alcohols Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-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
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000000049 anti-anxiety effect Effects 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
229960000956 coumarin Drugs 0.000 description 1
235000001671 coumarin Nutrition 0.000 description 1
ANQAZDNMUFDCFU-UHFFFAOYSA-N cyclohexen-1-yloxysilane Chemical compound C1(=CCCCC1)O[SiH3] ANQAZDNMUFDCFU-UHFFFAOYSA-N 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
SHALBPKEGDBVKK-VOTSOKGWSA-N danishefsky's diene Chemical compound CO\C=C\C(=C)O[Si](C)(C)C SHALBPKEGDBVKK-VOTSOKGWSA-N 0.000 description 1
238000006567 deketalization reaction Methods 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000005907 ketalization reaction Methods 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
MPXHGMFNVXPWFF-UHFFFAOYSA-N methyl 4-oxocyclohexene-1-carboxylate Chemical compound COC(=O)C1=CCC(=O)CC1 MPXHGMFNVXPWFF-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA356,593A 1976-07-06 1980-07-18 Traduction non-disponible Expired CA1100979A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA356,593A CA1100979A (fr)	1976-07-06	1980-07-18	Traduction non-disponible

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US702,804		1976-07-06
US05/702,804 US4054581A (en)	1976-07-06	1976-07-06	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
CA281,764A CA1090813A (fr)	1976-07-06	1977-06-30	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
CA356,593A CA1100979A (fr)	1976-07-06	1980-07-18	Traduction non-disponible

Publications (1)

Publication Number	Publication Date
CA1100979A true CA1100979A (fr)	1981-05-12

Family

ID=27165165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA356,593A Expired CA1100979A (fr)	1976-07-06	1980-07-18	Traduction non-disponible

Country Status (1)

Country	Link
CA (1)	CA1100979A (fr)

1980
- 1980-07-18 CA CA356,593A patent/CA1100979A/fr not_active Expired

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Legal Events

Date	Code	Title	Description
1998-05-12	MKEX	Expiry