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1. 发明授权

US06610866B2 Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds 有权
公开(公告)号：US06610866B2
公开(公告)日：2003-08-26
申请号：US09833055
申请日：2001-04-12
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： C07J5300
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.

2. 发明授权

US06849741B2 Method for preparing compounds derived from thiazolidinedione, oxazolidinedione or hydantoin 失效
标题翻译：制备衍生自噻唑烷二酮，恶唑烷二酮或乙内酰脲的化合物的方法
公开(公告)号：US06849741B2
公开(公告)日：2005-02-01
申请号：US10636155
申请日：2003-08-07
申请人： Michel Bulliard , Yvon Derrien , Tony Pintus
发明人： Michel Bulliard , Yvon Derrien , Tony Pintus
IPC分类号： C07B61/00 , C07D233/54 , C07D233/78 , C07D233/84 , C07D233/96 , C07D263/44 , C07D277/20 , C07D277/34 , C07D417/12 , C07D213/30
CPC分类号： C07D263/44 , C07D233/78 , C07D233/96 , C07D277/20 , C07D277/34 , C07D417/12
摘要： A method for preparing a thiazolidinedione, oxazolidinedione or hydantoin compound of formula (I) from a compound of formula (II): wherein Q represents an oxygen atom or a sulfur atom; Q1 represents an oxygen atom or a sulfur atom; R1 and R2, which can be identical or different, represent a hydrogen atom, a C1-10 alkyl chain, a cycloalkyl, an alkylaryl, an arylalkyl; the alkyl, cycloalkyl, alkylaryl or arylalkyl groups being optionally substituted by an alkyl, an alkoxy or aryloxy, a halogen, a hydroxy, a sulfino, a sulfonyl, an amino such as NH2, NHR3, N(R3)2, wherein R3 represents an alkyl, an alkoxy or an alkylcarbonyl, reacting a compound of formula (II) with formic acid, either as a hydrogen donor in a hydrogen-transfer reaction or as a solvent in a hydrogenation reaction, in the presence of a catalyst containing a transition metal to obtain a corresponding compound of formula (I).
摘要翻译：从式（II）化合物制备式（I）的噻唑烷二酮，恶唑烷二酮或乙内酰脲化合物的方法：其中Q表示氧原子或硫原子; Q1表示氧原子或硫原子; R1和R2可以相同或不同，表示氢原子，C1-10烷基链，环烷基，烷基芳基，芳基烷基; 烷基，环烷基，烷基芳基或芳烷基任选被烷基，烷氧基或芳氧基，卤素，羟基，亚磺酰基，磺酰基，氨基如NH 2，NHR 3，N（R 3）2取代，其中R 3表示烷基，烷氧基或烷基羰基，在氢转移反应中作为氢供体或在加氢反应中作为溶剂使式（II）化合物与甲酸反应，在含有过渡金属的催化剂存在下，得到相应的式（I）化合物。

3. 发明授权

US06794525B2 Optically active chiral diphosphine ligands 失效
标题翻译：光学活性的手性二膦配体
公开(公告)号：US06794525B2
公开(公告)日：2004-09-21
申请号：US10356233
申请日：2003-01-31
申请人： Michel Bulliard , Blandine Laboue , Sonia Roussiasse
发明人： Michel Bulliard , Blandine Laboue , Sonia Roussiasse
IPC分类号： C07F1500
CPC分类号： C07F15/0053 , B01J31/2409 , B01J31/2414 , B01J2231/52 , B01J2231/643 , B01J2231/645 , B01J2531/0208 , B01J2531/0266 , B01J2531/26 , B01J2531/31 , B01J2531/42 , B01J2531/46 , B01J2531/821 , B01J2531/822 , B01J2531/827 , C07B53/00 , C07B2200/07 , C07C67/31 , C07F9/5027 , C07C69/732
摘要： An (R) or (S) chiral diphosphine of formula (I): wherein R and R1, which can be identical or different, represent an optionally saturated C1-10 alkyl group, an optionally saturated C3-9 cycloalkyl group, a C5-10 aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R4 representing an alkyl, an alkoxy or an alkylcarbonyl, the alkyl, cycloalkyl, aryl groups optionally including one or more heteroatoms, or R and R1 together represent an optionally saturated C2-6 substituted alkyl group, an optionally saturated C3-9 cycloalkyl group, a C5-10 aryl group, the cycloalkyl or aryl groups being optionally substituted by a C1-5 alkyl, a halogen, a hydroxy, a C1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R4 representing an alkyl, an alkoxy or an alkylcarbonyl, the alkyl, cycloalkyl, aryl groups optionally including one or more heteroatoms, R2 and R3, which can be identical or different, represent an optionally saturated C3-8 cycloalkyl group, a C6-10 aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R4 representing an alkyl, an alkoxy or an alkylcarbonyl, the cycloalkyl, aryl groups optionally including one or more heteroatoms, or R2 and R3 together form an optionally saturated C4-8 cyclic group, a C6-10 aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R4 representing an alkyl, an alkoxy or an alkylcarbonyl, the cyclic and aryl groups optionally including one or more heteroatoms.
摘要翻译：式（I）的（R）或（S）手性二膦：其中R和R 1可以相同或不同，表示任选饱和的C 1-10烷基，任选饱和的C 3-9环烷基， 10芳基，该基团任选被卤素，羟基，C 1-5烷氧基，氨基，亚磺酰基，磺酰基取代，R 4表示烷基，烷氧基或烷基羰基，烷基，环烷基，芳基任选地包括一个或多个杂原子，或R和R 1一起表示任选饱和的C 2-6取代烷基，任选饱和的C 3-9环烷基，C 5-10芳基，环烷基或芳基任选被C 1 -5-烷基，卤素，羟基，C 1-5烷氧基，氨基，亚磺酰基，磺酰基，其中R 4表示烷基，烷氧基或烷基羰基，烷基，环烷基，芳基，任选地包括一个或多个杂原子可以相同或不同的R 2和R 3表示任选饱和的 C 3〜C 8环烷基，C 6-10芳基，所述基团任选被卤素，羟基，C 1-5烷氧基，氨基，亚磺酰基，磺酰基取代，R 4表示烷基，烷氧基或烷基羰基，环烷基，任选地包括一个或多个杂原子的芳基，或者R 2和R 3一起形成任选饱和的C 4-8环基，C 6-10芳基，该基团任选被卤素取代，羟基， C 1-5烷氧基，氨基，亚磺酰基，磺酰基，其中R 4表示烷基，烷氧基或烷基羰基，环和芳基任选地包括一个或多个杂原子。

4. 发明授权

US06262283B1 Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds 失效
标题翻译：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。

5. 发明授权

US06861535B2 Cyclization method for the synthesis of pyrrolidine derivative compounds 有权
标题翻译：用于合成吡咯烷衍生物化合物的环化方法
公开(公告)号：US06861535B2
公开(公告)日：2005-03-01
申请号：US10449377
申请日：2003-05-30
申请人： Michel Bulliard , Blandine Laboue , Jean-Francois Pluvie , Sonia Roussiasse , Tony Pintus
发明人： Michel Bulliard , Blandine Laboue , Jean-Francois Pluvie , Sonia Roussiasse , Tony Pintus
IPC分类号： C07B61/00 , C07D207/08 , C07D207/12 , C07D207/00
CPC分类号： C07D207/12
摘要： A method for preparing pyrrolidine derivatives comprising cyclizing a compound of formula (I): in the presence of: a) a catalyst, b) a primary amine and c) a base, in a solvent to obtain pyrrolidine derivative of formula (II) below:
摘要翻译：一种制备吡咯烷衍生物的方法，其包括使式（I）化合物环化：在a）催化剂，b）伯胺和c）碱的存在下，在溶剂中得到下述式（II）的吡咯烷衍生物：

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