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    Process for production of delta-9- tetrahydrocannabinol
    1.
    发明申请
    Process for production of delta-9- tetrahydrocannabinol 失效
    制备δ-9-四氢大麻酚的方法

    公开(公告)号：US20070093665A1

    公开(公告)日：2007-04-26

    申请号：US11529147

    申请日：2006-09-28

    申请人： David Burdick ,  Steven Collier ,  Frederic Jos ,  Betina Biolatto ,  Bernhard Paul ,  Harold Meckler ,  Mark Helle ,  Alicia Habershaw

    发明人： David Burdick ,  Steven Collier ,  Frederic Jos ,  Betina Biolatto ,  Bernhard Paul ,  Harold Meckler ,  Mark Helle ,  Alicia Habershaw

    IPC分类号： C07D311/80

    CPC分类号： C07C29/00 ,  C07C37/16 ,  C07C67/343 ,  C07C2601/16 ,  C07C35/16 ,  C07C39/23 ,  C07C69/94

    摘要： The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R8, R9, and R10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R1, R2, and R3 defined herein.

    摘要翻译： 本发明涉及一种制备δ-9-四氢大麻酚化合物或其衍生物的方法，包括在有效制备δ-9-四氢大麻酚化合物或其衍生物的条件下，用有机铝基路易斯酸催化剂处理第一中间体化合物 。 本发明的另一方面涉及制备大麻二醇或大麻二酸化合物的方法，包括在金属三氟甲磺酸酯催化剂存在下，在有效形成大麻二醇或大麻二醇化合物的条件下使第一起始化合物与第二起始化合物反应。 本发明还涉及下式的化合物：其中R 8，R 9和R 10是相同或不同的且独立地 选自H，取代或未取代的烷基，取代或未取代的芳基，取代或未取代的杂芳基或卤素，R 1，R 2和R 2， 本文定义的SUB> 3 。

    Process for production of delta-9-tetrahydrocannabinol
    2.
    发明授权
    Process for production of delta-9-tetrahydrocannabinol 有权
    生产delta-9-四氢大麻酚的方法

    公开(公告)号：US08106244B2

    公开(公告)日：2012-01-31

    申请号：US13108651

    申请日：2011-05-16

    申请人： David C. Burdick ,  Steven J. Collier ,  Betina Biolatto ,  Harold Meckler

    发明人： David C. Burdick ,  Steven J. Collier ,  Betina Biolatto ,  Harold Meckler

    IPC分类号： C07C35/18

    CPC分类号： C07C29/00 ,  C07C37/16 ,  C07C67/343 ,  C07C2601/16 ,  C07C35/16 ,  C07C39/23 ,  C07C69/94

    摘要： The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R8, R9, and R10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R1, R2, and R3 defined herein.

    摘要翻译： 本发明涉及一种制备δ-9-四氢大麻酚化合物或其衍生物的方法，包括在有效制备δ-9-四氢大麻酚化合物或其衍生物的条件下，用有机铝基路易斯酸催化剂处理第一中间体化合物 。 本发明的另一方面涉及制备大麻二醇或大麻二酸化合物的方法，包括在金属三氟甲磺酸酯催化剂存在下，在有效形成大麻二醇或大麻二醇化合物的条件下使第一起始化合物与第二起始化合物反应。 本发明还涉及下式化合物：其中R 8，R 9和R 10相同或不同且独立地选自H，取代或未取代的烷基，取代或未取代的芳基，取代或未取代的杂芳基，或 卤素，其中R 1，R 2和R 3定义如下。

    PROCESS FOR PRODUCTION OF DELTA-9-TETRAHYDROCANNABINOL
    3.
    发明申请
    PROCESS FOR PRODUCTION OF DELTA-9-TETRAHYDROCANNABINOL 有权
    生产DELTA-9-四氢胞嘧啶的方法

    公开(公告)号：US20110263878A1

    公开(公告)日：2011-10-27

    申请号：US13108651

    申请日：2011-05-16

    申请人： David C. BURDICK ,  Steven J. Collier ,  Betina Biolatto ,  Harold Meckler

    发明人： David C. BURDICK ,  Steven J. Collier ,  Betina Biolatto ,  Harold Meckler

    IPC分类号： C07D311/80 ,  C07C315/00 ,  C07F9/02 ,  C07C381/00 ,  C07F7/02 ,  C07C43/18

    CPC分类号： C07C29/00 ,  C07C37/16 ,  C07C67/343 ,  C07C2601/16 ,  C07C35/16 ,  C07C39/23 ,  C07C69/94

    摘要： The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R8, R9, and R10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R1, R2, and R3 defined herein.

    摘要翻译： 本发明涉及一种制备δ-9-四氢大麻酚化合物或其衍生物的方法，包括在有效制备δ-9-四氢大麻酚化合物或其衍生物的条件下，用有机铝基路易斯酸催化剂处理第一中间体化合物 。 本发明的另一方面涉及制备大麻二醇或大麻二酸化合物的方法，包括在金属三氟甲磺酸酯催化剂存在下，在有效形成大麻二醇或大麻二醇化合物的条件下使第一起始化合物与第二起始化合物反应。 本发明还涉及下式化合物：其中R 8，R 9和R 10相同或不同且独立地选自H，取代或未取代的烷基，取代或未取代的芳基，取代或未取代的杂芳基，或 卤素，其中R 1，R 2和R 3定义如下。

    Process for production of delta-9-tetrahydrocannabinol
    4.
    发明授权
    Process for production of delta-9-tetrahydrocannabinol 失效
    生产delta-9-四氢大麻酚的方法

    公开(公告)号：US07674922B2

    公开(公告)日：2010-03-09

    申请号：US11529147

    申请日：2006-09-28

    申请人： David C. Burdick ,  Steven J. Collier ,  Frédéric Jos ,  Betina Biolatto ,  Bernhard J. Paul ,  Harold Meckler ,  Mark A. Helle ,  Alicia J. Habershaw

    发明人： David C. Burdick ,  Steven J. Collier ,  Frédéric Jos ,  Betina Biolatto ,  Bernhard J. Paul ,  Harold Meckler ,  Mark A. Helle ,  Alicia J. Habershaw

    IPC分类号： C07D311/80 ,  C07C39/18

    CPC分类号： C07C29/00 ,  C07C37/16 ,  C07C67/343 ,  C07C2601/16 ,  C07C35/16 ,  C07C39/23 ,  C07C69/94

    摘要： The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R8, R9, and R10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R1, R2, and R3 defined herein.

    摘要翻译： 本发明涉及一种制备δ-9-四氢大麻酚化合物或其衍生物的方法，包括在有效制备δ-9-四氢大麻酚化合物或其衍生物的条件下，用有机铝基路易斯酸催化剂处理第一中间体化合物 。 本发明的另一方面涉及制备大麻二醇或大麻二酸化合物的方法，包括在金属三氟甲磺酸酯催化剂存在下，在有效形成大麻二醇或大麻二醇化合物的条件下使第一起始化合物与第二起始化合物反应。 本发明还涉及下式化合物：其中R 8，R 9和R 10相同或不同且独立地选自H，取代或未取代的烷基，取代或未取代的芳基，取代或未取代的杂芳基，或 卤素，其中R 1，R 2和R 3定义如下。

    Pyrrolylphenyl-substituted hydroxamic acid derivatives
    7.
    发明授权
    Pyrrolylphenyl-substituted hydroxamic acid derivatives 失效
    吡咯基苯基取代的异羟肟酸衍生物

    公开(公告)号：US5096919A

    公开(公告)日：1992-03-17

    申请号：US439731

    申请日：1989-11-20

    申请人： Jan W. F. Wasley ,  Karl O. Gelotte ,  Harold Meckler

    发明人： Jan W. F. Wasley ,  Karl O. Gelotte ,  Harold Meckler

    IPC分类号： C07D207/32 ,  C07D207/325 ,  C07D207/327

    CPC分类号： C07D207/325 ,  C07D207/327

    摘要： Disclosed are the pyrrolylphenyl-substituted hydroxamic acid derivatives of the formula ##STR1## wherein R represents hydrogen, lower alkyl, halogen or lower alkoxy; R.sub.1 and R.sub.2 independently represent hydrogen, lower alkyl or aryl; Y represents a direct bond, lower alkylene, lower alkenylene, lower alkadienylene, (thio, sulfinyl or sulfonyl)-lower alkylene or oxy-lower alkylene; Z represents ##STR2## wherein R.sub.3 represents hydrogen or acyl; R.sub.4 represents lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl, aryl or aryl-lower alkyl; or Z represents ##STR3## wherein R.sub.3 represents hydrogen or acyl; R.sub.5 represents lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl, aryl, aryl-lower alkyl, amino or N-(mono- or di-lower alkyl)-amino; R.sub.6 and R.sub.7 represent hydrogen or lower alkyl; and pharmaceutically acceptable salts thereof provided that R.sub.3 represents hydrogen; which are useful as selective lipoxygenase inhibitors, methods for preparation thereof, pharmaceutical compositions comprising said compounds, and a method of inhibiting lipoxygenase and of treating diseases in mammals which are responsive to lipoxygenase inhibition using said compounds and pharmaceutical compositions comprising said compounds of the invention.

    摘要翻译： 公开了式（I）的吡咯基苯基取代的异羟肟酸衍生物，其中R表示氢，低级烷基，卤素或低级烷氧基; R1和R2独立地表示氢，低级烷基或芳基; Y表示直接键，低级亚烷基，低级亚烯基，低级亚烷基亚芳基，（硫代，亚磺酰基或磺酰基） - 低级亚烷基或氧 - 低级亚烷基; Z代表（a）其中R3代表氢或酰基; R 4表示低级烷基，C 3 -C 7 - 环烷基，芳基或芳基 - 低级烷基; 或Z表示（b）其中R3表示氢或酰基; R 5表示低级烷基，C 3 -C 7 - 环烷基，芳基，芳基 - 低级烷基，氨基或N-（单 - 或二 - 低级烷基） - 氨基; R6和R7代表氢或低级烷基; 其药学上可接受的盐，其中R3表示氢; 其可用作选择性脂氧合酶抑制剂，其制备方法，包含所述化合物的药物组合物，以及抑制脂氧合酶的方法，以及使用所述化合物和包含本发明化合物的药物组合物治疗对脂氧合酶抑制作用有抑制作用的哺乳动物疾病的方法。

    Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds
    10.
    发明授权
    Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds 失效
    用于制备氨基甾醇，维生素D类似物和其他化合物的24-羟化化合物的立体选择性合成

    公开(公告)号：US06262283B1

    公开(公告)日：2001-07-17

    申请号：US08985876

    申请日：1997-12-05

    申请人： William A. Kinney ,  Steven Jones ,  Xuehai Zhang ,  Meena N. Rao ,  Michel Bulliard ,  Harold Meckler ,  Nancy Lee

    发明人： William A. Kinney ,  Steven Jones ,  Xuehai Zhang ,  Meena N. Rao ,  Michel Bulliard ,  Harold Meckler ,  Nancy Lee

    IPC分类号： C07J4100

    CPC分类号： C07J31/006 ,  C07J9/00 ,  C07J41/0005

    摘要： A method is described for stereoselectively reducing an unsaturated alkyl ketone substituent attached to a fused ring base. In this method, the unsaturated alkyl ketone reacts with a chiral oxazaborolidine reagent. This reaction stereoselectively reduces the unsaturated alkyl ketone to an unsaturated alkyl alcohol. The unsaturated alkyl alcohol can be further reduced, if desired, to produce a saturated alkyl alcohol. The fused ring base can be, for example, a steroid ring base or a base of a vitamin D analog. The process in accordance with the invention can be used with an alkeneone substituent (e.g., a 22-ene-24-one substituent) or an alkyneone substituent (e.g., a 22-yne-24-one substituent) on a steroid ring base to make squalamine or other useful aminosterol compounds and intermediates for making aminosterol compounds.

    摘要翻译： 描述了立体选择性还原与稠环基团连接的不饱和烷基酮取代基的方法。 在该方法中，不饱和烷基酮与手性恶唑硼烷试剂反应。 该反应立体选择性地将不饱和烷基酮还原成不饱和烷基醇。 如果需要，可以进一步还原不饱和烷基醇以制备饱和烷基醇。 稠环基可以是例如类固醇环基或维生素D类似物的碱。 根据本发明的方法可以与类固醇环基上的烯酮取代基（例如，22-烯-24一取代基）或炔炔酮取代基（例如，22-炔-24-取代基）一起使用 制备角质胺或其他有用的氨基甾醇化合物和制备氨基甾醇化合物的中间体。