US 7,105,685 B2Granted

Cannabinol derivatives

OwnerCraig R. Travisinventor

Life of this patent

Estimating the term…

Abstract

The invention provides cannabinol derivatives and pharmaceutical preparations thereof.

Claims6

Dependent claims

A cannabinol derivative having the following formula:

wherein,
R1 is:
a) H,
b) a C1-4 alkyl group or ester thereof,
c) COOH,
d) OH,
e) a O—C1-5 alkyl (preferably OCH3) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups,
f) a O—CO—C3-10 alkyl group containing a carboxyl or amino group,
g)
wherein n=1 to 8
h) a p-aminobenzyl group or a C1-7 aminoalkyl group or an organic or mineral acid addition salt thereof, an isocyanate or isothiocyanate derivative of the p-aminobenzyl or aminoalkyl group, a carboxyl terminated derivative of the aminoalkyl group having from 1 to 7 additional carbon atoms or a salt thereof, and an activated derivative of the carboxyl terminated derivative;
i) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
j) an alpha ketoaldehyde (e.g., COCOH);
or
k) CH(CH3)CO2H or —OCOCH3,
R2 is:
a) H, OH, COOH, or a halogen,
b) C1-6 carboxy or alkoxy group, or
c) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen,
R3 is a dimethyl -pentyl, -hexyl, -heptyl, -octyl, or -nonyl that has a terminal halogen substituent;
R6 and R6′ together form ═O or ═S, or each is independently selected from the group consisting of:
a) hydrogen,
b) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
c) CN,
d) CO2H,
e) CO2—C1-4 alkyl,
f) C(Y)(Z) —OH,
g) C(Y)(Z) —O—C1-4 alkyl, and
h) C1-6 alkyl-CO2—Y, wherein Y and Z are each independently H or C1-6 alkyl,
R7 is:
a) hydroxy,
b) halo,
c) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
d) CN,
e) N3,
f) CO2H,
g) CO2—C1-4 alkyl,
h) C(Y)(Z) —OH,
i) C(Y)(Z) —O—C1-4 alkyl,
j) C1-6 alkyl-CO2—Y, or
k)═O or ═S,
wherein Y and Z are each independently H or C1-6 alkyl;
Q is:
a) O or S, or
b) N—W, wherein W is:
i) hydrogen,
ii) C1-6 alkoxyalkyl, C1-6 alkyl, or C1-6 haloalkyl,
iii) OC1-6 alkyl, or OC1-6 haloalkyl,
iv) CN,
v) C1-6 alkyl,
vi) C(Y)(Z)C1-4 alkyl, or
vii) C1-6 alkyl-CO2-Z,
wherein Y and Z are each independently H or C1-6 alkyl.

50 more elements

A cannabinol derivative having the following formula:

wherein,
R1 is:
a) H,
b) a C1-4 alkyl group or ester thereof,
c) COOH,
d) OH,
e) a O—C1-5 alkyl (preferably OCH3) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups,
f) a O—CO—C3-10 alkyl group containing a carboxyl or amino group,
g)
wherein n=1 to 8
h) a p-aminobenzyl group or a C1-7 aminoalkyl group or an organic or mineral acid addition salt thereof, an isocyanate or isothiocyanate derivative of the p-aminobenzyl or aminoalkyl group, a carboxyl terminated derivative of the aminoalkyl group having from 1 to 7 additional carbon atoms or a salt thereof, and an activated derivative of the carboxyl terminated derivative;
i) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
j) an alpha ketoaldehyde (e.g., COCOH);
or
k) CH(CH3)CO2H or —OCOCH3
R2 is:
a) H, OH, COOH, or a halogen,
b) C1-6 carboxy or alkoxy group, or
c) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen,
R3 is a dihaloalkyl, dihaloalkenyl, or dihaloalkynyl,
R6 and R6′ together form ═O or ═S, or each is independently selected from the group consisting of:
a) hydrogen,
b) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
c) CN,
d) CO2H,
e) CO2—C1-4 alkyl,
f) C(Y)(Z) —OH,
g) C(Y)(Z) —O—C1-4 alkyl, and
h) C1-6 alkyl-CO2—Y, wherein Y and Z are each independently H or C1-6 alkyl,
R7 is:
a) hydroxy,
b) halo,
c) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
d) CN,
e) N3,
f) CO2H,
h) C(Y)(Z) —OH,
i) C(Y)(Z) —O—C1-4 alkyl,
j) C1-6 alkyl-CO2—Y, or
k) ═O or ═S,
wherein Y and Z are each independently H or C1-6 alkyl;
Q is:
a) O or S, or
b) N—W, wherein W is:
i) hydrogen,
ii) C1-6 alkoxyalkyl, C1-6 alkyl, or C1-6 haloalkyl,
iii) OC1-6 alkyl, or OC1-6 haloalkyl,
iv) CN,
v) C1-6 alkyl,
vi) C(Y)(Z)C1-4 alkyl, or
vii) C1-6 alkyl-CO2-Z,
wherein Y and Z are each independently H or C1-6 alkyl.

49 more elements

A cannabinol derivative having the following formula:

wherein,
R1 is:
a) H,
b) a C1-4 alkyl group or ester thereof,
c) COOH,
d) OH,
e) a O—C1-5 alkyl (preferably OCH3) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups,
f) a O—CO—C3-10 alkyl group containing a carboxyl or amino group,
g)
h) a p-aminobenzyl group or a C1-7 aminoalkyl group or an organic or mineral acid addition salt thereof, an isocyanate or isothiocyanate derivative of the p-aminobenzyl or aminoalkyl group, a carboxyl terminated derivative of the aminoalkyl group having from 1 to 7 additional carbon atoms or a salt thereof, and an activated derivative of the carboxyl terminated derivative;
i) R1 and R2 comprise a substituent of the formula —O(CH2)3-5 wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
j) an alpha ketoaldehyde (e.g., COCOH);
or
k) CH(CH3)CO2H or —OCOCH3
R2 is:
a) H, OH, COOH, or a halogen,
b) C1-6 carboxy or alkoxy group, or
c) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen,
R3 comprises at least one triple bond;
R6 and R6′ together form ═O or ═S, or each is independently selected from the group consisting of:
a) hydrogen,
b) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
c) CN,
d) CO2H,
e) CO2—C1-4 alkyl,
f) C(Y)(Z) —OH,
g) C(Y)(Z) —O—C1-4 alkyl, and
h) C1-6 alkyl-CO2-Y, wherein Y and Z are each independently H or C1-6 alkyl,
R7is:
a) hydroxy,
b) halo,
c) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
d) CN,
e) N3,
f) CO2H,
g) CO2—C1-4 alkyl,
h) C(Y)(Z) —OH,
i) C(Y)(Z) —O—C1-4 alkyl,
j) C1-6 alkyl-CO2—Y, or
k) ═O or ═S,
wherein Y and Z are each independently H or C1-6 alkyl;
Q is:
a) O or S, or
b) N—W, wherein W is:
(i) hydrogen,
(ii) C1-6 alkoxyalkyl, C1-6 alkyl, or C1-6 haloalkyl,
(iii) OC1-6 alkyl, or OC1-6 haloalkyl,
(iv) CN,
(v) C1-6 alkyl,
(vi) C(Y)(Z)C1-4 alkyl, or
(vii) C1-6 alkyl-CO2-Z,
wherein Y and Z are each independently H or C1-6 alkyl.

49 more elements

The cannabinol derivative having the following formula:

wherein,
R1 is:
a) H,
b) a C1-4 alkyl group or ester thereof,
c) COOH,
d) OH,
e) a O—C1-5 alkyl (preferably OCH3) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups,
f) a O—CO—C3-10 alkyl group containing a carboxyl or amino group,
g)
wherein n=1 to 8
h) a p-aminobenzyl group or a C1-7 aminoalkyl group or an organic or mineral acid addition salt thereof, an isocyanate or isothiocyanate derivative of the p-aminobenzyl or aminoalkyl group, a carboxyl terminated derivative of the aminoalkyl group having from 1 to 7 additional carbon atoms or a salt thereof, and an activated derivative of the carboxyl terminated derivative;
i) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
j) an alpha ketoaldehyde (e.g., COCOH);
or
k) CH(CH3)CO2H or —OCOCH3
R1 is:
a) H, OH, COOH, or a halogen,
b) C1-6 carboxy or alkoxy group, or
c) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen,
R3 is 2′-ynyl, 3′-ynyl or 4′-ynyl,
R6 and R6′ together form ═O or ═S, or each is independently selected from the group consisting of:
a) hydrogen,
b) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
c) CN,
d) CO2H,
e) CO2—C1-4 alkyl,
f) C(Y)(Z) —OH,
g) C(Y)(Z) —O—C1-4 alkyl, and
h) C1-6 alkyl-CO2-Y, wherein Y and Z are each independently H or C1-6 alkyl,
R7 is:
a) hydroxy,
b) halo,
c) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
d) CN,
e) N3,
f) CO2H,
g) CO2—C1-4 alkyl,
h) C(Y)(Z) —OH,
j) C1-6 alkyl-CO2—Y, or
k) ═O or ═S,
wherein Y and Z are each independently H or C1-6 alkyl;
Q is:
a) O or S, or
b) N—W, wherein W is:
(i) hydrogen,
(ii) C1-6 alkoxyalkyl, C1-6 alkyl, or C1-6 haloalkyl,
(iii) OC1-6 alkyl, or OC1-6 haloalkyl,
(iv) CN,
(v) C1-6 alkyl,
(vi) C(Y)(Z)C1-4 alkyl, or
(vii) C1-6 alkyl-CO2-Z,
wherein Y and Z are each independently H or C1-6 alkyl.

49 more elements

The cannabinol derivative having the following formula:

wherein,
R1 is:
a) H,
b) a C1-4 alkyl group or ester thereof,
c) COOH,
d) OH,
e) a O—C1-5 alkyl (preferably OCH3) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups,
f) a O—CO—C3-10 alkyl group containing a carboxyl or amino group,
g)
wherein n=1 to 8
h) a p-aminobenzyl group or a C1-7 aminoalkyl group or an organic or mineral acid addition salt thereof, an isocyanate or isothiocyanate derivative of the p-aminobenzyl or aminoalkyl group, a carboxyl terminated derivative of the aminoalkyl group having from 1 to 7 additional carbon atoms or a salt thereof, and an activated derivative of the carboxyl terminated derivative;
i) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
j) an alpha ketoaldehyde (e.g., COCOH);
or
k) CH(CH3)CO2H or —OCOCH3
R2 is:
a) H, OH, COOH, or a halogen,
b) C1-6 carboxy or alkoxy group, or
c) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen,
R3 is 5,5-dimethyl hex(1-ene)(3-yne)yl;
R6 and R6′ together form ═O or ═S, or each is independently selected from the group consisting of:
a) hydrogen,
b) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C 1-6 haloalkyl,
c) CN,
d) CO2H,
e) CO2—C1-4 alkyl,
f) C(Y)(Z) —OH,
g) C(Y)(Z) —O—C1-4 alkyl, and
h) C1-6 alkyl-CO2-Y, wherein Y and Z are each independently H or C1-6 alkyl,
R7 is:
a) hydroxy,
b) halo,
c) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
d) CN,
e) N3,
f) CO2H,
g) CO2—C1-4 alkyl,
h) C(Y)(Z) —OH,
i) C(Y)(Z) —O—C1-4 alkyl,
j) C1-6 alkyl-CO2—Y, or
k) ═O or ═S,
wherein Y and Z are each independently H or C1-6 alkyl;
Q is:
a) O or S, or
b) N—W, wherein W is:
(i) hydrogen,
(ii) C1-6 alkoxyalkyl, C1-6 alkyl, or C1-6 haloalkyl,
(iii) OC1-6 alkyl, or OC1-6 haloalkyl,
(iv) CN,
(v) C1-6 alkyl,
(vi) C(Y)(Z)C1-4 alkyl, or
(vii) C1-6 alkyl-CO2-Z,
wherein Y and Z are each independently H or C1-6 alkyl.

50 more elements

A cannabinol derivative having the following formula:

wherein,
R1 is:
a) H,
b) a C1-4 alkyl group or ester thereof,
c) COOH,
d) OH,
e) a O—C1-5 alkyl (preferably OCH3) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups,
f) a O—CO—C3-10 alkyl group containing a carboxyl or amino group,
g)
wherein n=1 to 8
h) a p-aminobenzyl group or a C1-7 aminoalkyl group or an organic or mineral acid addition salt thereof, an isocyanate or isothiocyanate derivative of the p-aminobenzyl or aminoalkyl group, a carboxyl terminated derivative of the aminoalkyl group having from 1 to 7 additional carbon atoms or a salt thereof, and an activated derivative of the carboxyl terminated derivative;
i) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
j) an alpha ketoaldehyde (e.g., COCOH);
or
k) CH(CH3)CO2H or —OCOCH3
R2 is:
a) H, OH, COOH, or a halogen,
b) C1-6 carboxy or alkoxy group, or
c) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
R3 is 1,1,5-trimethylhexyl, 1,1,5,5-tetramethylhexyl, or 1,1,5-tri-methyl-hept-4-enyl;
R6 and R6′ together form ═O or ═S, or each is independently selected from the group consisting of:
a) hydrogen,
b) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
c) CN,
d) CO2H,
e) CO2—C1-4 alkyl,
f) C(Y)(Z) —OH,
g) C(Y)(Z) —O—C1-4 alkyl, and
h) C1-6 alkyl-CO2—Y, wherein Y and Z are each independently H or C1-6 alkyl,
R7 is:
a) hydroxy,
b) halo,
c) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
d) CN,
e) N3,
f) CO2H,
g) CO2—C1-4 alkyl,
h) C(Y)(Z) —OH,
i) C(Y)(Z) —O—C1-4 alkyl,
j) C1-6 alkyl-CO2—Y, or
k) ═O or ═S,
wherein Y and Z are each independently H or C1-6 alkyl;
Q is:
a) O or S, or
b) N—W, wherein W is:
i) hydrogen,
ii) C1-6 alkoxyalkyl, C1-6 alkyl, or C1-6 haloalkyl,
iii) OC1-6 alkyl, or OC1-4 haloalkyl,
iv) CN,
v) C1-6 alkyl,
vi) C(Y)(Z)C1-4 alkyl, or
vii) C1-6 alkyl-CO2-Z,
wherein Y and Z are each independently H or C1-6 alkyl.

50 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/328,242Filed 22 Dec 2002 · continuation
Priority: 22 Mar 1999
Published: US 2003/0158191 A121 Aug 2003
Granted: 12 Sep 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

A61K 31/05
Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates: phenols
A61K 31/09
Having an ether linkage to aromatic ring nuclear carbon: having two or more such linkages
A61K 31/353
Condensed with carbocyclic rings, e.g. methantheline: 3,4-Dihydrobenzopyrans, e.g. chroman, catechin
A61P 31/14
Antivirals: for RNA viruses

Family

Application60/125,674Us provisional application · filed 22 Mar 1999
Application60/151,595Us provisional application · filed 30 Aug 1999
Application09/533,386Parent of this continuation-in-part · filed 22 Mar 2000
Application09/928,683Parent of this continuation · filed 13 Aug 2001
US 2003/0158191 A1Pre-grant publication · published 21 Aug 2003
US 6,566,560 B2Parent of this continuation
US 6,274,635 B1Parent of this continuation-in-part
Application09/928,683Parent of this continuation-in-part
US 2002/0037923 A1Published application
US 7,105,685 B2This patent

From the US filing history. Foreign family members aren’t listed.

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A cannabinol derivative having the following formula:

wherein,
R1 is:
a) H,
b) a C1-4 alkyl group or ester thereof,
c) COOH,
d) OH,
e) a O—C1-5 alkyl (preferably OCH3) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups,
f) a O—CO—C3-10 alkyl group containing a carboxyl or amino group,
g)
wherein n=1 to 8
h) a p-aminobenzyl group or a C1-7 aminoalkyl group or an organic or mineral acid addition salt thereof, an isocyanate or isothiocyanate derivative of the p-aminobenzyl or aminoalkyl group, a carboxyl terminated derivative of the aminoalkyl group having from 1 to 7 additional carbon atoms or a salt thereof, and an activated derivative of the carboxyl terminated derivative;
i) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen;
j) an alpha ketoaldehyde (e.g., COCOH);
or
k) CH(CH3)CO2H or —OCOCH3,
R2 is:
a) H, OH, COOH, or a halogen,
b) C1-6 carboxy or alkoxy group, or
c) R1 and R2 comprise a substituent of the formula —O(CH2)3-5, wherein R1 and R2, together with the carbon atoms to which they are bonded, comprises a ring where at least one hydrogen atom thereof is optionally substituted with a halogen,
R3 is a dimethyl -pentyl, -hexyl, -heptyl, -octyl, or -nonyl that has a terminal halogen substituent;
R6 and R6′ together form ═O or ═S, or each is independently selected from the group consisting of:
a) hydrogen,
b) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
c) CN,
d) CO2H,
e) CO2—C1-4 alkyl,
f) C(Y)(Z) —OH,
g) C(Y)(Z) —O—C1-4 alkyl, and
h) C1-6 alkyl-CO2—Y, wherein Y and Z are each independently H or C1-6 alkyl,
R7 is:
a) hydroxy,
b) halo,
c) C1-6 alkoxy, C1-6 alkylthio, C1-6 alkyl, or C1-6 haloalkyl,
d) CN,
e) N3,
f) CO2H,
g) CO2—C1-4 alkyl,
h) C(Y)(Z) —OH,
i) C(Y)(Z) —O—C1-4 alkyl,
j) C1-6 alkyl-CO2—Y, or
k)═O or ═S,
wherein Y and Z are each independently H or C1-6 alkyl;
Q is:
a) O or S, or
b) N—W, wherein W is:
i) hydrogen,
ii) C1-6 alkoxyalkyl, C1-6 alkyl, or C1-6 haloalkyl,
iii) OC1-6 alkyl, or OC1-6 haloalkyl,
iv) CN,
v) C1-6 alkyl,
vi) C(Y)(Z)C1-4 alkyl, or
vii) C1-6 alkyl-CO2-Z,
wherein Y and Z are each independently H or C1-6 alkyl.

50 more elements

Facts

Application

10/328,242Filed 22 Dec 2002 · continuation

Priority

22 Mar 1999

Published

US 2003/0158191 A121 Aug 2003

Granted

12 Sep 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification15 codes

A61K 31/05
Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates: phenols
A61K 31/09
Having an ether linkage to aromatic ring nuclear carbon: having two or more such linkages
A61K 31/353
Condensed with carbocyclic rings, e.g. methantheline: 3,4-Dihydrobenzopyrans, e.g. chroman, catechin
A61P 31/14
Antivirals: for RNA viruses

Family

Application60/125,674Us provisional application · filed 22 Mar 1999

Application60/151,595Us provisional application · filed 30 Aug 1999

Application09/533,386Parent of this continuation-in-part · filed 22 Mar 2000

Application09/928,683Parent of this continuation · filed 13 Aug 2001

US 2003/0158191 A1Pre-grant publication · published 21 Aug 2003

US 6,566,560 B2Parent of this continuation

US 6,274,635 B1Parent of this continuation-in-part

Application09/928,683Parent of this continuation-in-part

US 2002/0037923 A1Published application

US 7,105,685 B2This patent

From the US filing history. Foreign family members aren’t listed.