US2023225985A1PendingUtilityA1
Terpenophenolic compounds and their use
Est. expiryMar 31, 2040(~13.7 yrs left)· nominal 20-yr term from priority
C07C 39/23A61K 31/05A61P 25/08C07C 37/14C07C 37/003C07C 39/15C07B 2200/09C07C 29/32C07C 33/38C07C 2601/16
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Claims
Abstract
The present disclosure describes terpenophenolic compounds and their use in medicine. The present disclosure further describes perrottetinene-like compounds, the manufacture thereof, formulations containing same and their use in medicine. Such compounds include (1′R,2′R)-5′-methyl-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol (CBD-PET) or (1′R,2′R)-4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol (CBD-PET-OH).
Claims
exact text as granted — not AI-modified1 . A method for treating a medical condition in a patient, comprising administering to the patient a therapeutically effective amount of a compound, which is any one selected from the group consisting of:
5′-methyl-4-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol having the following structure
4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol having the following structure
or a pharmaceutically acceptable salt or hydrate thereof.
2 . The method according to claim 1 , wherein the compound is 5′-methyl-4-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol (CBD-PET) having the following structure
or a pharmaceutically acceptable salt or hydrate thereof.
3 . The method according to claim 1 , wherein the compound is 4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol (CBD-PET-OH)
or a pharmaceutically acceptable salt or hydrate thereof.
4 . The method according to claim 1 , wherein the compound is (1′R,2′R)-5′-methyl-4-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((−) trans-CBD-PET)
or a pharmaceutically acceptable salt or hydrate thereof.
5 . The method according to claim 1 , wherein the compound is (1′S,2′S)-5′-methyl-4-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol) ((+)-cis-CBD-PET)
or a pharmaceutically acceptable salt or hydrate thereof.
6 . The method according to claim 1 , wherein the compound is (1′R,2′S)-5′-methyl-4-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((−) cis-CBD-PET)
or a pharmaceutically acceptable salt or hydrate thereof for use as a medicament.
7 . The method according to claim 1 , wherein the compound is (1′S,2′R)-5′-methyl-4-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol) ((+)-cis-CBD-PET)
or a pharmaceutically acceptable salt or hydrate thereof.
8 . The method according to claim 1 , wherein the compound is (1′R,2′R)-4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((−) trans-CBD-PET-OH)
or a pharmaceutically acceptable salt or hydrate thereof.
9 . The method according to claim 1 , wherein the compound is (1′S,2′S)-4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((+) cis CBD-PET-OH)
or a pharmaceutically acceptable salt or hydrate thereof.
10 . The method according to claim 1 , wherein the compound is (1′R,2′S)-4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((−) cis-CBD-PET-OH)
or a pharmaceutically acceptable salt or hydrate thereof.
11 . The method according to claim 1 , wherein the compound is (1′S,2′R)-4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((+) cis CBD-PET-OH)
or a pharmaceutically acceptable salt or hydrate thereof.
12 . The method according to claim 1 , wherein the compound is an o-isomer of trans-CBD-PET having a structure:
or a pharmaceutically acceptable salt or hydrate thereof.
13 . The method according to claim 1 , wherein the compound is o-isomer of trans-CBD-PET-OH having a structure:
or a pharmaceutically acceptable salt or hydrate thereof.
14 . The method according to claim 1 , wherein the compound is present as an isomer with a purity of at least 90% for use as a medicament.
15 . The method according to claim 1 , wherein the compound is present as a racemic mix of a respective (+) or (−) trans or (+) or (−) cis form for use as a medicament.
16 . The method according to claim 1 , wherein the compound is a p isomer with a purity of at least 90% for use as a medicament.
17 . The method according to claim 12 , wherein the compound is an o isomer with a purity of at least 90% for use as a medicament.
18 . The method according to claim 16 , wherein the isomer of the compound is at greater than 95% purity for use as a medicament.
19 . The method according to claim 1 , wherein the compound is a mixture of both p and o isomers for use as a medicament.
20 . The method according to claim 19 , wherein the two isomers forming the mixture of the compound are together present at greater than 95% purity for use as a medicament.
21 - 33 . (canceled)
34 . A pharmaceutical composition comprising a compound, which is any one selected from the group consisting of:
(a) 4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol (CBD-PET-OH)
and
(b) (1′R,2′R)-4 (4 hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((−) trans-CBD-PET-OH)
and
(c) compound (1′S,2′S)-4 (4 hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((+) cis CBD-PET-OH)
and
(d) (1′R,2′S)-4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((−) cis-CBD-PET-OH)
and
(e) (1′S,2′R)-4-(4-hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol ((+) cis CBD-PET-OH)
and
(f) an o-isomer of trans-CBD-PET-OH having a structure:
or a pharmaceutically acceptable salt or hydrate of one of (a) through (f) thereof;
or
(g) 5′-methyl-4-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol having the following structure
together with one or more pharmaceutically acceptable excipient(s).
35 .- 44 . (canceled)
45 . A method of manufacturing a perrottetinene-like compound comprising reacting menthadienol with dihydropinosylvin or dihydroresvratrol, suitably in the presence of a Lewis acid.
46 . The method according to claim 45 , wherein the Lewis acid is a zinc based acid.
47 . The method according to claim 46 , wherein the zinc based acid is zinc triflate.
48 . The method according to claim 47 , wherein the initial amount of the zinc triflate is at 0.01-0.05 mole equivalent to menthadienol.
49 . The method according to claim 45 to 48 , wherein the reaction of menthadienol with dihydropinosylvin or dihydroresvratrol takes place at or under the temperature ranging 80-120° C.
50 . The method according to claim 45 to 48 , wherein the perrottetinene-like compound is (1′R,2′R)-5′-methyl-4-phenethyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol (CBD-PET) when menthadienol is reacted with dihydropinosylvin.
51 . The method according to claim 45 to 48 , wherein the perrottetinene-like compound is (1′R,2′R)-4 (4 hydroxyphenethyl)-5′-methyl-2′-(prop-1-ene-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol (CBD-PET-OH) when menthadienol is reacted with dihydroresvratrol.
52 . The method of claim 51 , further comprising the step of producing dihydroresvratrol by hydrogenating trans-resveratrol in the presence of palladium on carbon (Pd/C).
53 . The method according to claim 45 , wherein menthadienol is p-menthadienolJoin the waitlist — get patent alerts
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