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1. 发明申请

US20060194986A1 Production methods of optically active hydrazine compound and optically active amine compound 失效
标题翻译：光学活性肼化合物和光学活性胺化合物的制备方法
公开(公告)号：US20060194986A1
公开(公告)日：2006-08-31
申请号：US11341852
申请日：2006-01-30
申请人： Yoshiji Takemoto , Kazuo Murakami
发明人： Yoshiji Takemoto , Kazuo Murakami
IPC分类号： C07C241/02
CPC分类号： C07C281/02 , Y02P20/55
摘要： The present invention relates to a production method of optically active hydrazine compound (IV), which includes reacting azo compound (II) with compound (III) in the presence of optically active compound (I). The present invention also relates to a production method of optically active amine compound (V), which includes producing optically active hydrazine compound (IV) by the above-mentioned method, reacting the optically active hydrazine compound (IV) with a base or an acid to eliminate a protecting group represented by PG, and then subjecting the resulting compound to catalytic reduction or reacting the resulting compound with a zinc powder to reduce a nitrogen-nitrogen bond. wherein X is S or O; C*, C** and C*** are asymmetric carbons, R1 and R2 are lower alkyl groups etc., R4 and R5 may in combination form cyclohexane etc., R3 is aryl group optionally having substituent(s) etc., R6 and R7 are hydrogen atoms etc., R8 is aryl group optionally having substituent(s) etc., R9 and R10 are electron withdrawing groups, and PG is a protecting group.
摘要翻译：本发明涉及光学活性肼化合物（Ⅳ）的制备方法，其包括在光学活性化合物（I）的存在下使偶氮化合物（Ⅱ）与化合物（Ⅲ）反应。本发明还涉及光学活性胺化合物（V）的制造方法，其包括通过上述方法制备旋光性肼化合物（Ⅳ），使光学活性肼化合物（Ⅳ）与碱或酸除去由PG表示的保护基，然后将所得化合物进行催化还原或使所得化合物与锌粉反应以降低氮 - 氮键。其中X是S或O; C *，C **和C ***是不对称碳，R 1和R 2都是低级烷基等，R 4， R 5和R 5可以组合形成环己烷等，R 3是任选具有取代基等的芳基，R 6和R R 9是氢原子等，R 8是任选具有取代基等的芳基，R 9和R 10 吸电子基团，PG是保护基。

2. 发明授权

US08580804B2 Compound having hetero ring skeleton, and process for producing optically active compound using the aforementioned compound as asymmetric catalyst 有权
标题翻译：具有杂环骨架的化合物和使用上述化合物作为不对称催化剂制备光学活性化合物的方法
公开(公告)号：US08580804B2
公开(公告)日：2013-11-12
申请号：US13259887
申请日：2010-04-09
申请人： Yoshiji Takemoto , Kazuo Murakami
发明人： Yoshiji Takemoto , Kazuo Murakami
IPC分类号： A01N43/54 , A61K31/517 , C07D239/72 , C07D401/00
CPC分类号： C07C253/30 , C07B53/00 , C07B2200/07 , C07C67/343 , C07C201/12 , C07C205/53 , C07C231/08 , C07C231/14 , C07C241/02 , C07C281/02 , C07C2602/10 , C07D233/88 , C07D235/30 , C07D239/95 , C07C69/757 , C07C233/92 , C07C255/41
摘要： The invention provides a compound having a heterocyclic skeleton of formula (I): wherein the indicated moieties are as described in the specification, as well as a tautomer thereof or a salt thereof. The compound is useful as a catalyst for an asymmetric synthesis.
摘要翻译：本发明提供具有式（I）的杂环骨架的化合物：其中所述部分如说明书中所述，以及其互变异构体或其盐。该化合物可用作不对称合成的催化剂。

3. 发明授权

US07655817B2 Production methods of optically active hydrazine compound and optically active amine compound 失效
标题翻译：光学活性肼化合物和光学活性胺化合物的制备方法
公开(公告)号：US07655817B2
公开(公告)日：2010-02-02
申请号：US11341852
申请日：2006-01-30
申请人： Yoshiji Takemoto , Kazuo Murakami
发明人： Yoshiji Takemoto , Kazuo Murakami
IPC分类号： C07C241/02
CPC分类号： C07C281/02 , Y02P20/55
摘要： The present invention relates to a production method of optically active hydrazine compound (IV), which includes reacting azo compound (II) with compound (III) in the presence of optically active compound (I). The present invention also relates to a production method of optically active amine compound (V), which includes producing optically active hydrazine compound (IV) by the above-mentioned method, reacting the optically active hydrazine compound (IV) with a base or an acid to eliminate a protecting group represented by PG, and then subjecting the resulting compound to catalytic reduction or reacting the resulting compound with a zinc powder to reduce a nitrogen-nitrogen bond. wherein X is S or O; C*, C** and C*** are asymmetric carbons, R1 and R2 are lower alkyl groups etc., R4 and R5 may in combination form cyclohexane etc., R3 is aryl group optionally having substituent(s) etc., R6 and R7 are hydrogen atoms etc., R8 is aryl group optionally having substituent(s) etc., R9 and R10 are electron withdrawing groups, and PG is a protecting group.
摘要翻译：本发明涉及光学活性肼化合物（Ⅳ）的制备方法，其包括在光学活性化合物（I）的存在下使偶氮化合物（Ⅱ）与化合物（Ⅲ）反应。本发明还涉及光学活性胺化合物（V）的制造方法，其包括通过上述方法制备旋光性肼化合物（Ⅳ），使光学活性肼化合物（Ⅳ）与碱或酸除去由PG表示的保护基，然后将所得化合物进行催化还原或使所得化合物与锌粉反应以降低氮 - 氮键。其中X是S或O; C *，C **和C ***是不对称碳，R1和R2是低级烷基等，R4和R5可以组合形成环己烷等，R3是任选具有取代基的芳基等，R6 R7为氢原子等，R8为任选具有取代基的芳基等，R9和R10为吸电子基团，PG为保护基。

4. 发明授权

US09073823B2 Compound having hetero ring skeleton, and process for producing optically active compound using the aforementioned compound as asymmetric catalyst 有权
标题翻译：具有杂环骨架的化合物和使用上述化合物作为不对称催化剂制备光学活性化合物的方法
公开(公告)号：US09073823B2
公开(公告)日：2015-07-07
申请号：US13828411
申请日：2013-03-14
申请人： Yoshiji Takemoto , Kazuo Murakami
发明人： Yoshiji Takemoto , Kazuo Murakami
IPC分类号： C07C253/30 , C07B53/00 , C07C67/343 , C07C205/53 , C07C231/08 , C07C281/02 , C07D235/30 , C07D239/95 , C07C201/12 , C07C231/14 , C07C241/02 , C07D233/88
CPC分类号： C07C253/30 , C07B53/00 , C07B2200/07 , C07C67/343 , C07C201/12 , C07C205/53 , C07C231/08 , C07C231/14 , C07C241/02 , C07C281/02 , C07C2602/10 , C07D233/88 , C07D235/30 , C07D239/95 , C07C69/757 , C07C233/92 , C07C255/41
摘要： The invention provides a compound having a heterocyclic skeleton of formula (I): wherein the substituents are as defined in the specification, as well as a tautomer thereof or a salt thereof. The invention also provides asymmetric synthesis methods involving the use of such a compound, tautomer thereof, or salt thereof, as a catalyst.
摘要翻译：本发明提供具有式（I）的杂环骨架的化合物：其中取代基如说明书中所定义，以及其互变异构体或其盐。本发明还提供涉及使用这种化合物，其互变异构体或其盐作为催化剂的不对称合成方法。

5. 发明申请

US20120095227A1 COMPOUND HAVING HETERO RING SKELETON, AND PROCESS FOR PRODUCING OPTICALLY ACTIVE COMPOUND USING THE AFOREMENTIONED COMPOUND AS ASYMMETRIC CATALYST 有权
标题翻译：具有环状骨架的化合物和使用化合物作为不对称催化剂生产光学活性化合物的方法
公开(公告)号：US20120095227A1
公开(公告)日：2012-04-19
申请号：US13259887
申请日：2010-04-09
申请人： Yoshiji Takemoto , Kazuo Murakami
发明人： Yoshiji Takemoto , Kazuo Murakami
IPC分类号： C07D239/95 , C07D235/30
CPC分类号： C07C253/30 , C07B53/00 , C07B2200/07 , C07C67/343 , C07C201/12 , C07C205/53 , C07C231/08 , C07C231/14 , C07C241/02 , C07C281/02 , C07C2602/10 , C07D233/88 , C07D235/30 , C07D239/95 , C07C69/757 , C07C233/92 , C07C255/41
摘要： The present invention provides a compound having a heterocyclic skeleton, which is represented by of the formula (I): wherein R1 and R2 are the same or different and each is a lower alkyl group optionally having substituent(s), an aralkyl group optionally having substituent(s) or an aryl group optionally having substituent(s), or R1 and R2 in combination form, together with the nitrogen atom they are bonded to, a heterocycle optionally having substituent(s) (the heterocycle is optionally condensed with an aromatic hydrocarbon ring); ring A is an imidazole ring condensed with an aromatic ring optionally having substituent(s), or a pyrimidin-4-one ring condensed with an aromatic ring optionally having substituent(s); R3 and R4 are the same or different and each is a lower alkyl group optionally having substituent(s), a lower alkenyl group optionally having substituent(s), a lower alkynyl group optionally having substituent(s), an aralkyl group optionally having substituent(s) or an aryl group optionally having substituent(s), or R3 and R4 in combination form, together with the carbon atoms they are respectively bonded to, a homocycle optionally having substituent(s), or a heterocycle optionally having substituent(s) (the homocycle and heterocycle are optionally condensed with an aromatic hydrocarbon ring); and R5 and R6 are the same or different and each is a hydrogen atom or a lower alkyl group optionally having substituent(s), a tautomer thereof or a salt thereof, and which is useful as a catalyst for an asymmetric synthesis.
摘要翻译：本发明提供具有式（I）表示的具有杂环骨架的化合物：其中R 1和R 2相同或不同，各自为任选具有取代基的低级烷基，任选具有取代基的芳烷基取代基或任选具有取代基的芳基，或组合形式的R 1和R 2与它们所连接的任选具有取代基的杂环的氮原子连接（该杂环任选地与芳香族稠合烃环）; 环A是与任选具有取代基的芳香环稠合的咪唑环或与任选具有取代基的芳环稠合的嘧啶-4-酮环; R 3和R 4相同或不同，各自为任选具有取代基的低级烷基，任选具有取代基的低级烯基，任选具有取代基的低级炔基，任选具有取代基的芳烷基，或任选具有取代基的芳基或组合形式的R 3和R 4以及它们分别连接的任选具有取代基的杂环或任选具有取代基的杂环的碳原子，）（同环和杂环任选与芳烃环稠合）; R 5和R 6相同或不同，各自为氢原子或任选具有取代基的低级烷基，其互变异构体或其盐，可用作不对称合成的催化剂。

6. 发明授权

US08809567B2 Method for producing silylenol ethers 有权
标题翻译：甲硅烷醇醚的制备方法
公开(公告)号：US08809567B2
公开(公告)日：2014-08-19
申请号：US13582577
申请日：2011-03-03
申请人： Kiyosei Takasu , Yoshiji Takemoto , Kei Kurahashi
发明人： Kiyosei Takasu , Yoshiji Takemoto , Kei Kurahashi
IPC分类号： C07F7/04
CPC分类号： C07F7/188 , C07J1/0059 , C07J7/002 , C07J51/00
摘要： The invention relates to a method for producing silyl enol ether compound (3) by reacting ketone or aldehyde compound (1) with allylsilane compound (2) in the presence of a base and 0.00001 to 0.5 equivalents of an acid catalyst relative to ketone or aldehyde compound (1).
摘要翻译：本发明涉及一种在碱存在下使酮或醛化合物（1）与烯丙基硅烷化合物（2）反应生成甲硅烷基烯醇醚化合物（3）的方法，相对于酮或醛为0.00001至0.5当量酸催化剂化合物（1）。

7. 发明申请

US20060161006A1 Asymmetric urea compound and process for producing asymmetric compound by asymmetric conjugate addition reaction with the same as catalyst 有权
标题翻译：不对称脲化合物和通过与催化剂相同的不对称共轭加成反应制备不对称化合物的方法
公开(公告)号：US20060161006A1
公开(公告)日：2006-07-20
申请号：US10562579
申请日：2004-06-25
申请人： Yoshiji Takemoto
发明人： Yoshiji Takemoto
IPC分类号： C07D211/26 , C07D207/30
CPC分类号： C07C335/16 , C07B2200/07 , C07C205/51 , C07C205/53 , C07C205/55 , C07C269/06 , C07C275/30 , C07C335/18 , C07C2601/14 , C07C2602/10 , C07D209/08 , C07C271/22
摘要： The present invention relates to a production method of asymmetric compound (IV) which includes conjugately adding nucleophilic reagent (III) to compound (II) in the presence of asymmetric urea compound (I). The present invention provides a non-metallic asymmetric catalyst capable of realizing a highly stereoselective asymmetric conjugate addition reaction in a high yield, and an advantageous production method of an asymmetric compound by an asymmetric conjugate addition reaction using the asymmetric catalyst. wherein X is an oxygen atom or a sulfur atom; C*, C** and C*** are asymmetric carbons; R1, R2, R4, R5, R8, R9 and R10 are each a lower alkyl group optionally having substituent(s) and the like, or R4 and R5 and the like in combination optionally form a homocyclic ring optionally having substituent(s) and the like; R3 is an aryl group optionally having substituent(s) and the like; R6 and R7 are each a hydrogen atom and the like; Nu is —CR16 (COR17)(COR18) wherein R16, R17 and R18 are each a lower alkyl group optionally having substituent(s) and the like, and the like; and EWG is an electron withdrawing group.
摘要翻译：本发明涉及不对称化合物（Ⅳ）的制备方法，其包括在不对称脲化合物（I）存在下，将化合物（II）共轭加入亲核试剂（Ⅲ）。本发明提供能够高收率地实现高立体选择性不对称共轭加成反应的非金属不对称催化剂，以及使用不对称催化剂的不对称共轭加成反应的不对称化合物的有利制造方法。其中X是氧原子或硫原子; C *，C **和C ***是不对称碳; R 1，R 2，R 4，R 5，R 8， R 9和R 10各自为任选具有取代基等的低级烷基，或R 4和R 4， 5等组合任选形成任选具有取代基等的任意的环状环; R 3是任选具有取代基的芳基等; R 6和R 7各自为氢原子等; 其中R 16是R 16，其中R 16，R 17，R 16，R 16，＆lt;＆gt;和＆lt; 18＆gt;各自为任选具有取代基等的低级烷基等。 EWG是吸电子组。

8. 发明授权

US07632970B2 Asymmetric urea compound and process for producing asymmetric compound by asymmetric conjugate addition reaction with the same as catalyst 有权
标题翻译：不对称脲化合物和通过与催化剂相同的不对称共轭加成反应制备不对称化合物的方法
公开(公告)号：US07632970B2
公开(公告)日：2009-12-15
申请号：US10562579
申请日：2004-06-25
申请人： Yoshiji Takemoto
发明人： Yoshiji Takemoto
IPC分类号： C07C275/00
CPC分类号： C07C335/16 , C07B2200/07 , C07C205/51 , C07C205/53 , C07C205/55 , C07C269/06 , C07C275/30 , C07C335/18 , C07C2601/14 , C07C2602/10 , C07D209/08 , C07C271/22
摘要： The present invention relates to a production method of asymmetric compound (IV) which includes conjugately adding nucleophilic reagent (III) to compound (II) in the presence of asymmetric urea compound (I). The present invention provides a non-metallic asymmetric catalyst capable of realizing a highly stereoselective asymmetric conjugate addition reaction in a high yield, and an advantageous production method of an asymmetric compound by an asymmetric conjugate addition reaction using the asymmetric catalyst. wherein X is an oxygen atom or a sulfur atom; C*, C** and C*** are asymmetric carbons; R1, R2, R4, R5, R8, R9 and R10 are each a lower alkyl group optionally having substituent(s) and the like, or R4 and R5 and the like in combination optionally form a homocyclic ring optionally having substituent(s) and the like; R3 is an aryl group optionally having substituent(s) and the like; R6 and R7 are each a hydrogen atom and the like; Nu is —CR16(COR17)(COR18) wherein R16, R17 and R18 are each a lower alkyl group optionally having substituent(s) and the like, and the like; and EWG is an electron withdrawing group.
摘要翻译：本发明涉及不对称化合物（Ⅳ）的制备方法，其包括在不对称脲化合物（I）存在下，将化合物（II）共轭加入亲核试剂（Ⅲ）。本发明提供能够高收率地实现高立体选择性不对称共轭加成反应的非金属不对称催化剂，以及使用不对称催化剂的不对称共轭加成反应的不对称化合物的有利制造方法。其中X是氧原子或硫原子; C *，C **和C ***是不对称碳; R 1，R 2，R 4，R 5，R 8，R 9和R 10各自为任选具有取代基等的低级烷基，或者R 4和R 5等组合任选地形成任选具有取代基的稠环和类似; R3是任选具有取代基等的芳基; R6和R7各自为氢原子等; Nu为-CR16（COR17）（COR18）其中R16，R17和R18各自为任选具有取代基的低级烷基等;等等; EWG是吸电子组。

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