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公开(公告)号：US20210198224A1
公开(公告)日：2021-07-01
申请号：US17269722
申请日：2019-08-20
申请人： Bessor Pharma, LLC
IPC分类号： C07D311/78 , C07C37/56
摘要： A process for the preparation of substantially pure diverse known and novel cannabinoids 1 and 2, which include Δ9-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), cannabidiol (11), cannabidivarin (12) and other naturally occurring tetracyclic and tricyclic cannabinoids and other synthetic tetracyclic and tricyclic analogues, via intermediates 3, 6, 4 and 5, using a cascade sequence of allylic rearrangement, aromatization and, for the tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2, including Δ9-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The known and novel analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis or cannabis oil.
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公开(公告)号：US11407724B2
公开(公告)日：2022-08-09
申请号：US17269722
申请日：2019-08-20
申请人： Bessor Pharma, LLC
IPC分类号： C07D311/78 , C07C37/50 , C07C39/23 , C07D319/08 , C07D493/04 , A61K31/05 , A61K31/352
摘要： A process for the preparation of substantially pure diverse known and novel cannabinoids 1 and 2, which include Δ9-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), cannabidiol (11), cannabidivarin (12) and other naturally occurring tetracyclic and tricyclic cannabinoids and other synthetic tetracyclic and tricyclic analogues, via intermediates 3, 6, 4 and 5, using a cascade sequence of allylic rearrangement, aromatization and, for the tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2, including Δ9-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The known and novel analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis or cannabis oil.
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公开(公告)号：US20210238157A1
公开(公告)日：2021-08-05
申请号：US17269732
申请日：2019-08-20
申请人： Bessor Pharma, LLC
IPC分类号： C07D311/78 , C07C39/23 , C07D493/04 , C07D319/08
摘要： The present invention relates to novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.
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4.发明申请公开(公告)号：US20220340537A1
公开(公告)日：2022-10-27
申请号：US17738055
申请日：2022-05-06
申请人： Bessor Pharma, LLC
IPC分类号： C07D311/78 , C07C39/23 , C07D319/08 , C07D493/04 , A61K31/05 , A61K31/352 , C07C37/50 , C07C37/56
摘要： The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed.
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公开(公告)号：US11370768B2
公开(公告)日：2022-06-28
申请号：US17269732
申请日：2019-08-20
申请人： Bessor Pharma, LLC
IPC分类号： C07D311/78 , C07C37/56 , C07C39/23 , C07D319/08 , C07D493/04 , A61K31/05 , A61K31/352
摘要： The present invention relates to novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.
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公开(公告)号：US20240101503A1
公开(公告)日：2024-03-28
申请号：US17767760
申请日：2020-10-07
申请人： Bessor Pharma, LLC
IPC分类号： C07C51/09 , C07C37/50 , C07D319/08
CPC分类号： C07C51/09 , C07C37/50 , C07D319/08
摘要： The present invention relates to a process for the preparation of diverse known and novel cannabinoids 5, which include cannabigerol (CBG, 1), cannabigerolic acid (CBGA, 2), cannabigerovarin (CBGV, 3), cannabigerovarinic acid (CBGVA, 4) and other naturally occurring monocyclic cannabinoids and other analogues from simple inexpensive starting materials using a cascade sequence of allylic rearrangement and aromatization. Novel cannabinoids of series 5 are also claimed as part of the invention. These synthesized cannabinoids, unlike the minor cannabinoids isolated from Cannabis saliva or synthesized from the condensation reactions such as the reactions of substituted resorcinols with monoterpenes, are much easier to obtain at high purity levels. In particular, these cannabinoids, including but not limited to cannabigerol (CBG, 1), cannabigerolic acid (CBGA, 2), cannabigerovarin (CBGV, 3) and cannabigerovarinic acid (CBGVA, 4) are obtained without contamination with impurities with variation in RA and RB (e.g. contamination of CBG with CBGV).
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7.发明授权公开(公告)号：US11685724B2
公开(公告)日：2023-06-27
申请号：US17738055
申请日：2022-05-06
申请人： Bessor Pharma, LLC
IPC分类号： C07D319/06 , C07D311/78 , C07C39/23 , C07D319/08 , C07D493/04 , A61K31/05 , A61K31/352 , C07C37/50 , C07C37/56
CPC分类号： C07D311/78 , A61K31/05 , A61K31/352 , C07C37/50 , C07C37/56 , C07C39/23 , C07D319/08 , C07D493/04 , C07C2601/16 , C07C37/50 , C07C39/23 , A61K31/352 , A61K2300/00 , A61K31/05 , A61K2300/00
摘要： The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil.
Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed.-
公开(公告)号：US20210236460A1
公开(公告)日：2021-08-05
申请号：US17269751
申请日：2019-08-20
申请人： Bessor Pharma, LLC
IPC分类号： A61K31/352 , A61K31/05
摘要： The use of a medicament as a single agent, binary agent, or other combination comprising of substantially pure novel cannabinoids 1 and 2, optionally admixed with one or more known and novel cannabinoids and other known naturally occurring and synthetic tetracyclic 2A and tricyclic 1A cannabinoids for the prevention, treatment or cure of inflammatory mediated diseases or inflammatory mediated pathological conditions, anorexia, arthritis, cancer, pain, glaucoma, migraine, persistent muscle spasms, seizures (epileptic seizures), severe nausea, PTSD, autism spectrum disorder, drug abuse, insomnia, or any other chronic or persistent medical symptom.
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