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US3873576A Expired / Lapsed US ⏱️ 0.0 years remaining

Tetrahydrodibenzopyrans

Assignee: Individual
•
Filing: 1972-10-05
•
Granted: 1975-03-25
•
Expires: 1992-10-05
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Abstract

Abstract (-)-1-Hydroxy-3-alkyl-6,6-dimethyl-9-hydroxymethyl-6a,10a-trans6a,7,10,10a -tetrahydrodibenzo-(b,d)-pyrans (Formula 1) are produced in good yields from the corresponding 9-methylene-1,8di-acyl compounds (Formula 2) by thermal conversion of the latter into the corresponding 1,11-di-acyl compounds (Formula 3) which are converted into the target compound (Formula 1) by removal of the two acyl groups. Formula 1 compounds, where the alkyl group is a straight or branched chain alkyl of from 1-4 and 6-10 Catoms are novel homologues of the 3-n-pentyl compound, a metabolite of tetrahydrocannabinol known per se. Formula 1 compounds have bactericidic, sedative, analgetic and psychomimetic effect when applied to the human organism. Novel compounds (Formulae 4a, 5b, 6 and 7) are disclosed as starting materials and/or intermediates, some of them having pharmacological utility similar to the Formula 1 compounds.

Inventors

  • 👤 Theodor Petrzilka

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 17:59
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/04; C07D311/00; C07D311/02; C07D311/78; C07D311/80; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 9 words
A PROCESS FOR PREPARING A COMPOUND OF THE FORMULA
Claim 2
Dependent Claim 9 words
A PROCESS FOR PREPARING A COMPOUND OF THE FORMULA
Claim 3
Dependent Claim 28 words
The process as claimed in claim 1, wherein said compound of formula (2) is heated to a temperature in the range of from about 200*C to about 300*C.
Claim 4
Dependent Claim 18 words
The process as claimed in claim 2, wherein said compound of formula (2) is heated to about 290*C.
Claim 5
Dependent Claim 13 words
The process as claimed in claim 1, wherein R1 is the n-pentyl radical.
Claim 6
Dependent Claim 13 words
The process as claimed in claim 1, wherein R is the methyl group.
Claim 7
Dependent Claim 9 words
A process for preparing a compound of the formula
Claim 8
Dependent Claim 9 words
A process for preparing a compound of the formula
Claim 9
Dependent Claim 9 words
A process for preparing a compound of the formula
Claim 10
Dependent Claim 9 words
A process for preparing a compound of the formula
Claim 11
Dependent Claim 5 words
A compound of the formula
Claim 12
Dependent Claim 5 words
A compound of the formula
Claim 13
Dependent Claim 5 words
A compound of the formula
Claim 14
Dependent Claim 5 words
A compound of the formula
Claim 15
Dependent Claim 5 words
A compound of the formula
Claim 16
Dependent Claim 5 words
A compound of the formula
Claim 17
Dependent Claim 5 words
A compound of the formula
Claim 18
Dependent Claim 5 words
A compound of the formula
Claim 19
Dependent Claim 5 words
A compound of the formula
Claim 20
Dependent Claim 5 words
A compound of the formula

References Cited (Backward Citations)

US3388136A Cited
US3668224A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-03-24 1978-09-23 1979-03-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-03-24 1982-09-23 1983-03-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-03-24 1986-09-23 1987-03-25 $7700.00 Window Closed / Lapsed

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