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21. 发明授权

US4297485A Production of a selectively protected N-acylated derivative of an aminoglycosidic antibiotic 失效
标题翻译：制备氨基糖苷类抗生素的选择性保护的N-酰化衍生物
公开(公告)号：US4297485A
公开(公告)日：1981-10-27
申请号：US90591
申请日：1979-11-02
申请人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Yasushi Takagi , Tomo Jikihara
发明人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Yasushi Takagi , Tomo Jikihara
IPC分类号： C07H15/234 , C07H23/00 , C07H15/22
CPC分类号： C07H23/00 , C07H15/234
摘要： Aminoglycosidic antibiotic comprising a 6-0-(3"-aminoglycosyl)-2-deoxystreptamine optionally having a 4-0-(aminogycosyl) group, such as kanamycins, gentamicins, sisomicin, forms reversible complex with zinc cations by association of the zinc cations with some pairs of aminohydroxyl groups in the aminoglycoside, and the zinc-complexed amino groups are blocked from acylation. Reaction of this zinc complex with an acylation reagent having an amino-blocking acyl group brings about acylation of the non-complexed amino groups to give an N-acylated zinc complex, namely a complex of zinc cation with an N-acylated aminoglycosidic antibiotic derivative. Removal of zinc cations from N-acylated zinc complex yields a partially N-acylated aminoglycosidic antibiotic where 1- and 3"-amino groups are unprotected but all other amino groups protected with acyl group. Further reaction of this partially N-acylated product with a certain alkanoic acid or N-formyl-imidazole results in preferential acylation of 3"-amino group without 1-amino group being acylated, affording a 1-N-unprotected and other N-fully-protected derivative of the aminoglycosidic antibiotic which is valuable to be 1-N-acylated with .alpha.-hydroxy-.omega.-aminoalkanoic acid for high-yield production of known semi-synthetic 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl)-aminoglycosidic antibiotic.
摘要翻译：包含任选具有4-0-（氨基糖基）基团的6-0-（3“ - 氨基糖基）-2-脱氧神经胺的氨基糖苷类抗生素，如卡那霉素，庆大霉素，西索米星，与锌阳离子形成与锌阳离子的可逆复合物，在氨基糖苷中具有一对氨基羟基的阳离子和锌络合的氨基被封闭以进行酰化。该锌络合物与具有氨基封闭酰基的酰化试剂的反应导致非络合氨基的酰化，得到N-酰化锌络合物，即锌阳离子与N-酰化氨基糖苷类抗生素衍生物的络合物。从N-酰化锌络合物中除去锌阳离子产生部分N-酰化的氨基糖苷类抗生素，其中1-和3“ - 氨基未被保护，但是用酰基保护的所有其它氨基。该部分N-酰化产物与某种链烷酸或N-甲酰基 - 咪唑的进一步反应导致3'-氨基的优先酰化而没有1-氨基被酰化，得到1-N-未保护的和其它N- 氨基糖苷类抗生素的完全保护的衍生物，其有价值的是用α-羟基-ω-氨基链烷酸1-N-酰化，用于高产量生产已知的半合成的1-N-（α-羟基 - ω-氨基烷酰基）氨基糖苷类抗生素。

22. 发明授权

US4845082A 3'4'-dideoxy-3'-fluorokanamycin B and production thereof 失效
标题翻译： 3'4'-二脱氧-3'-氟霉素B及其制备
公开(公告)号：US4845082A
公开(公告)日：1989-07-04
申请号：US899100
申请日：1986-08-22
申请人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Yoshihiko Kobayashi
发明人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Yoshihiko Kobayashi
IPC分类号： C07H15/234 , A61K31/70 , A61K31/7028 , A61K31/7034 , A61K31/7036 , A61P31/04 , C07H15/236
CPC分类号： C07H15/234 , Y02P20/55
摘要： New compound, 3',4'-dideoxy-3'-fluorokanamycin B is now provided, which is useful as antibacterial agent.3',4'-Dideoxy-3'-fluorokanamycin B is prepared by a process comprising halogenating an N,O-protected derivative of 3'-deoxy-3'-fluoro-4'-O-sulfonylkanamycin B with a metal halide, reducing the resulting 4'- halogenated 3'-deoxy-3'-fluorokanamycin B derivative to convert its 4'-halo group into a hydrogen atom, and thereby to produce an N,O-protected derivative of 3',4'-dideoxy-3'-fluorokanamycin B, and removing the remaining amino-protecting groups and the remaining hydroxyl-protecting groups from the reduction product by conventional deprotecting methods.
摘要翻译：现在提供新的化合物3'，4'-二脱氧-3'-氟卡那霉素B，其可用作抗菌剂。 3'，4'-二脱氧-3'-氟卡那霉素B通过包括用金属卤化物卤化3'-脱氧-3'-氟-4'-O-磺酰基卡那霉素B的N，O-保护的衍生物的方法制备，减少所得的4'-卤代3'-脱氧-3'-氟卡那霉素B衍生物以将其4'-卤基转化成氢原子，从而产生3'，4'-二脱氧的N，O-保护的衍生物 -3'-氟卡那霉素B，并通过常规去保护方法从还原产物中除去剩余的氨基保护基团和剩余的羟基保护基团。

23. 发明授权

US4661474A 2',3'-dideoxy-2'-fluorokanamycin A and 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl) derivatives thereof 失效
标题翻译： 2'，3'-二脱氧-2'-氟卡那霉素A及其1-N-（α-羟基-ω-氨基烷酰基）衍生物
公开(公告)号：US4661474A
公开(公告)日：1987-04-28
申请号：US807485
申请日：1985-12-10
申请人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Yoshiaki Takahashi
发明人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Yoshiaki Takahashi
IPC分类号： C07H15/236 , A61K31/71 , C07H15/234
CPC分类号： C07H15/234 , Y02P20/55
摘要： New compounds, 2',3'-dideoxy-2'-fluorokanamycin A and 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl) derivatives thereof, particularly 1-N-(DL- or L-3-amino-2-hydroxypropionyl)- and 1-N-(L-4-amino-2-hydroxybutyryl)-2',3'-dideoxy-2'-fluorokanamycins A are now provided, which are each useful as antibacterial agent. 2',3'-Dideoxy-2'-fluorokanamycin A is prepared by a process comprising condensing a 6-azido-4-O-protected-2,3,6-trideoxy-2-fluoro-.alpha.-D-ribo-hexopyranosyl bromide with the 4-hydroxyl group of a 6-O-(2',4',6'-tri-O-protected-3'-N-protected-3'-amino-3'-deoxy-.alpha.-D-glucopyranosyl)-1,3-bis-N-protected-2-deoxystreptamine, reducing the resulting condensation product to convert its azido group into an amino group, and removing the remaining amino-protecting and hydroxyl-protecting groups from the reduction product.
摘要翻译：新化合物2'，3'-二脱氧-2'-氟卡那霉素A及其1-N-（α-羟基-ω-氨基烷酰基）衍生物，特别是1-N-（DL-或L-3-氨基-2- 羟基丙酰基） - 和1-N-（L-4-氨基-2-羟基丁酰基）-2'，3'-二脱氧-2'-氟吗啉霉素A，其各自可用作抗菌剂。 2'，3'-二脱氧-2'-氟卡那霉素A通过以下方法制备，该方法包括将6-叠氮基-4-O-保护的2,3,6-三脱氧-2-氟-α-D-吡喃六氟肉豆蔻基溴化物与6-O-（2'，4'，6'-三-O-保护的3'-N-保护的-3'-氨基-3'-脱氧-α-D- D-吡喃葡萄糖基）-1,3-双-N-保护的2-脱氧链霉胺，将所得缩合产物还原，将其叠氮基转化为氨基，并从还原产物中除去剩余的氨基保护基和羟基保护基团。

24. 发明授权

US4634688A 3'-fluoro-3'-deoxykanamycin A 失效
标题翻译： 3'-氟-3'-脱氧卡那霉素A
公开(公告)号：US4634688A
公开(公告)日：1987-01-06
申请号：US758819
申请日：1985-07-25
申请人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Yoshiaki Takahashi
发明人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Yoshiaki Takahashi
IPC分类号： C07H15/234 , A61K31/70 , A61K31/7028 , A61K31/7034 , A61K31/7036 , A61P31/04 , C07H9/04 , C07H15/236 , A61K31/71 , C07H15/22
CPC分类号： C07H15/234 , C07H9/04 , Y02P20/55
摘要： A new compound, 3'-fluoro-3'-deoxykanamycin A is now provided, which is active against gram-negative and gram-positive bacteria, including kanamycin-resistant strains of bacteria and is useful as antibacterial agent for therapeutic treatment of bacterial infections. This new compound is produced by a process comprising reacting a 6-azido-2,4-di-O-protected-3,6-dideoxy-3-fluoro-.alpha.-D-glucopyranosyl bromide with the 4-hydroxyl group of a 6-O-(2'-O-protected-3'-N-protected-3'-amino-4',6'-di-O-protected-3'-deoxy-.alpha.-D-glucopyranosyl)-1,3-bis-N-protected-2-deoxystreptamine, reducing the azido group of the resulting reaction product into an amino group, and removing the remaining protective groups from the reduction product.
摘要翻译：现在提供了一种新的化合物3'-氟-3'-脱氧卡那霉素A，其对革兰氏阴性和革兰氏阳性细菌具有活性，包括卡那霉素抗性细菌菌株，并且可用作细菌感染的治疗性治疗用抗菌剂。该新化合物通过包括使6-叠氮基-2,4-二-O-保护的3,6-二脱氧-3-氟-α-D-吡喃葡萄糖基溴与6位的4-羟基反应的方法制备 -O-（2'-O-保护的3'-N-保护的3'-氨基-4'，6'-二-O-保护的-3'-脱氧-α-D-吡喃葡萄糖基） 3-双-N-保护的2-脱氧链霉胺，将所得反应产物的叠氮基还原成氨基，并从还原产物中除去剩余的保护基团。

25. 发明授权

US4473557A 3"-Deoxystreptomycin production thereof and pharmaceutical compositions containing same 失效
标题翻译： 3“ - 其中含有霉菌霉素及含有它们的药物组合物
公开(公告)号：US4473557A
公开(公告)日：1984-09-25
申请号：US475269
申请日：1983-03-09
申请人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Takayuki Usui
发明人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Takayuki Usui
IPC分类号： A61K31/70 , A61K31/7028 , A61K31/7034 , A61K31/7036 , A61P31/04 , C07H15/238 , A61K31/71 , C07H15/22
CPC分类号： C07H15/238 , Y02P20/55
摘要： A new semi-synthetic antibiotic, 3"-deoxystreptomycin is now provided, which is useful as an antibacterial agent and is produced from 3"-deoxydihydrostreptomycin by a process comprising oxidizing the 3'-hydroxymethyl group of 2,5,6,4",6"-penta-O-acetyl-2"-N-benzyloxycarbonyl-3"-deoxydihydrostreptomycin as prepared by skilled introduction of amino-protecting group and hydroxyl-protecting group of appropriately selected natures into 3"-deoxydihydrostreptomycin, and then removing the protective groups from the oxidation product, 2,5,6,4",6"-penta-O-acetyl-2"-N-benzyloxycarbonyl-3"-deoxystreptomycin.
摘要翻译：现在提供一种新的半合成抗生素3'-脱氧链霉素，其可用作抗菌剂并且由3'-脱氧双氢链霉素通过包括氧化2,5,6的3'-羟甲基的方法制备， 4“，6” - 五-O-乙酰基-2“ - N-苄氧羰基-3” - 脱氧二氢嘧啶霉素，由熟练引入氨基保护基和适当选择的性质的羟基保护基制成3' 脱氧链霉素，然后从氧化产物2,5,6,4'，6“ - 五-O-乙酰基-2”-N-苄氧羰基-3“ - 脱氧链霉素中除去保护基团。

26. 发明授权

US4008362A 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin and the production thereof 失效
标题翻译： 1-N - （（S） - {60-取代的 - {107-氨基酰基） - 纳米颗粒或 - 瑞波霉素及其制备
公开(公告)号：US4008362A
公开(公告)日：1977-02-15
申请号：US390217
申请日：1973-08-21
申请人： Eiichi Akita , Tsutomu Tsuchiya , Shinichi Kondo , Shuntaro Yasuda , Sumio Umezawa , Hamao Umezawa
发明人： Eiichi Akita , Tsutomu Tsuchiya , Shinichi Kondo , Shuntaro Yasuda , Sumio Umezawa , Hamao Umezawa
IPC分类号： A61K31/70 , A61K31/7028 , A61K31/7034 , A61K31/7036 , A61K31/704 , A61P31/04 , C07H15/224 , C07H15/23 , C07H15/244
CPC分类号： C07H15/224 , C07H15/23
摘要： An 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR1## wherein R is a hydrogen atom or .beta.-D-ribofuranosyl group of the formula ##STR2## and R.sub.3 is hydroxyl, amino-NH.sub.2 or acylamino group --NHR.sub.4 in which R.sub.4 is an acyl group, and n is a whole number of 1 to 4, may be produced by subjecting the corresponding O-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR3## or its hydroxyl-masked and maino-masked form, to the action of a basic medium to produce an acyl-migration product of the formula: ##STR4## and, optionally converting the amino-masking groups into hydrogen atoms and also the hydroxyl-masking group into hydroge atom in a known manner if said amino-masking groups and said hydroxyl-masking groups are present in the acyl-migration product. The 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin produced is characterized by its useful activity inhibitory to the growth of bacteria resistant to the parent substance neamine or ribostamycin.
摘要翻译：式（1）的1-N - （（S）-α-取代的ω-氨基酰基） - 单胺或-ribostamycin，其中R为氢原子或式为“IMAGE”的β-D-呋喃核糖基，R3为是其中R 4为酰基，n为整数1至4的羟基，氨基-NH 2或酰基氨基-NHR 4，其可以通过使相应的O - （（S）-α-取代的ω- 氨基酰基） - 奈米霉素或结晶霉素或其羟基掩蔽和主掩蔽形式，与碱性介质的作用产生下式的酰基迁移产物：和/或将如果所述氨基掩蔽基团和所述羟基掩蔽基团存在于酰基迁移产物中，则以已知方式将氨基掩蔽基团转化成氢原子，并将羟基掩蔽基团转变成水解原子。产生的1-N - （（S）-α-取代的ω-氨基酰基） - 单胺或 - 生物素 - 特异霉素的特征在于其对母体neamine或核糖霉素具有抗性的细菌的生长有抑制作用。

27. 发明授权

US4008218A 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin and the production thereof 失效
标题翻译： 1-N - （（S） - {60-取代的 - {107-氨基酰基） - 纳米颗粒或 - 瑞波霉素及其制备
公开(公告)号：US4008218A
公开(公告)日：1977-02-15
申请号：US559771
申请日：1975-03-19
申请人： Eiichi Akita , Tsutomu Tsuchiya , Shinichi Kondo , Shuntaro Yasuda , Sumio Umezawa , Hamao Umezawa
发明人： Eiichi Akita , Tsutomu Tsuchiya , Shinichi Kondo , Shuntaro Yasuda , Sumio Umezawa , Hamao Umezawa
IPC分类号： C07H15/224 , C07H15/23 , C07G11/00
CPC分类号： C07H15/224 , C07H15/23
摘要： An 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula: ##STR1## wherein R is a hydrogen atom or .beta.-D-ribofuranosyl group of the formula ##STR2## and R.sub.3 is hydroxyl, amino-NH.sub.2 or acylamino group --NHR.sub.4 in which R.sub.4 is an acyl group, and n is a whole number of 1 to 4, may be produced by subjecting the corresponding O-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR3## or its hydroxyl-masked and amino-masked form, to the action of a basic medium to produce an acyl-migration product of the formula: ##STR4## and, optionally converting the amino-masking groups into hydrogen atoms and also the hydroxyl-masking group into hydrogen atom in a known manner if said amino-masking groups and said hydroxyl-masking groups are present in the acyl-migration product. The 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin produced is characterized by its useful activity inhibitory to the growth of bacteria resistant to the parent substance neamine or ribostamycin.
摘要翻译：具有下式的1-N - （（S）-α-取代的ω-氨基酰基） - 微量胺或 - 瑞波霉素：其中R是式“IMAGE”的氢原子或β-D-呋喃核糖基， R 3是羟基，氨基-NH 2或酰基氨基-NHR 4，其中R 4是酰基，n是整数1至4，可以通过使相应的O - （（S）-α-取代的-ω- - 氨基酰基） - 或者其羟基掩蔽和氨基掩蔽形式的微生物胺或β-内啡霉素或碱性培养基，以产生下式的酰基迁移产物：如果所述氨基掩蔽基团和所述羟基掩蔽基团存在于酰基迁移产物中，则以已知的方式将氨基掩蔽基团转化成氢原子，并将羟基掩蔽基团转变为氢原子。产生的1-N - （（S）-α-取代的ω-氨基酰基） - 单胺或 - 生物霉素的特征在于其对母体neamine或核糖霉素具有抗性的细菌的生长有抑制作用。

28. 发明授权

US4438107A Aminoglycosides and use thereof 失效
标题翻译：氨基糖苷类及其用途
公开(公告)号：US4438107A
公开(公告)日：1984-03-20
申请号：US402812
申请日：1982-07-28
申请人： Isamu Watanabe , Takashi Yamaguchi , Kazuhiro Kamiya , Toshihito Mori , Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya
发明人： Isamu Watanabe , Takashi Yamaguchi , Kazuhiro Kamiya , Toshihito Mori , Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya
IPC分类号： A61K31/70 , A61K31/7028 , A61K31/7034 , A61K31/7036 , A61P31/04 , C07D303/16 , C07H15/224 , C07H15/226 , C08B37/00
CPC分类号： C07H15/224 , C07D303/16 , C07H15/226
摘要： An aminoglycoside compound of the following formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a hydrogen atom and the other, a methyl group, R.sub.3 represents a hydrogen atom or an amino acyl group having 2 to 5 carbon atoms, R.sub.4 represents a lower alkyl group substituted by one or two substituents selected from the class consisting of hydroxy and amino groups, or a hexopyranosyl group whose hydroxy groups may be substituted by amino groups,and a pharmaceutically acceptable acid addition salt thereof; and an antibiotic composition comprising said compound and its pharmaceutically acceptable acid addition salt.
摘要翻译：下式的氨基糖苷类化合物其中R 1和R 2中的一个表示氢原子，另一个是甲基，R 3表示氢原子或具有2至5个碳原子的氨基酰基，R 4表示被一个或两个选自羟基和氨基的取代基取代的低级烷基或其羟基可被氨基取代的六吡喃糖基及其药学上可接受的酸加成盐; 以及包含所述化合物及其药学上可接受的酸加成盐的抗生素组合物。

29. 发明授权

US4349666A Process for the production of kanomycin B derivatives and products obtained therefrom 失效
标题翻译：生产卡那霉素B衍生物的方法及由此获得的产品
公开(公告)号：US4349666A
公开(公告)日：1982-09-14
申请号：US196586
申请日：1980-10-14
申请人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Toshiaki Miyake
发明人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Toshiaki Miyake
IPC分类号： C07H15/234 , C07H15/236 , C07H15/22
CPC分类号： C07H15/234 , Y02P20/55
摘要： 3'-Deoxykanamycin B, namely tobramycin is produced in an improved yield with a reduced reaction time under moderate reaction conditions, starting from a penta-N-protected 3'-mono-O-alkyl-, aralkyl- or arylsulfonylated derivative of kanamycin B in which all the 1, 3, 2' and 3"-amino groups and possibly the 6'-amino group have been protected by an arylsulfonyl group, especially tosyl group; the 3'-hydroxyl group of kanamycin B has been alkyl-, aralkyl- or arylsulfonylated; the 4"- and 6"-hydroxyl groups have been blocked with a di-valent hydroxyl-protecting group; and possibly the 4'-hydroxyl group and 6'-amino group have been blocked by being converted into the form of a 4', 6'-cyclic carbamate formed between the 4'-hydroxyl group and the 6'-amino group, by subjecting to a process essentially comprising reaction of said protected kanamycin B derivative with a metal halide for a reaction time of 30 min. to 2 hours at a reaction temperature of 0.degree. C..about.150.degree. C. to produce the corresponding 3'-halo compound, reductive replacement of the 3'-halo group by hydrogen and deprotection.
摘要翻译： 3-脱氧卡那霉素B，即在中等反应条件下，以5-N保护的3'-单-O-烷基 - 芳烷基 - 或芳基磺酰化衍生物开始，在中等反应条件下，产率提高，产量提高，反应时间缩短。其中所有1,3,2'和3“ - 氨基和可能的6'-氨基都被芳基磺酰基，尤其是甲苯磺酰基保护; 卡那霉素B的3'-羟基已经是烷基 - ，芳烷基 - 或芳基磺酰化; 4“和6” - 羟基已被二价羟基保护基封闭; 并且可能的4'-羟基和6'-氨基已经通过在4'-羟基和6'-氨基之间形成的4'，6'-环状氨基甲酸酯的形式被阻断，通过进行基本上包含所述受保护的卡那霉素B衍生物与金属卤化物的反应的方法，反应时间为30分钟。在0℃的反应温度下反应2小时。在150℃降解产生相应的3'-卤代化合物，通过氢还原取代3'-卤代基团并脱保护。

30. 发明授权

US4125706A Novel process for the preparation of 1-N-(alpha-substituted-omega-aminoacyl)-3'-deoxyribostamycin 失效
标题翻译：制备1-N-（α-取代-ω-氨基酰基）-3 {40-去氧孕酮霉素的新方法
公开(公告)号：US4125706A
公开(公告)日：1978-11-14
申请号：US676792
申请日：1976-04-14
申请人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya
发明人： Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya
IPC分类号： C07H15/23 , C07H15/20
CPC分类号： C07H15/23
摘要： A 1-N-(.alpha.-substituted-.omega.-aminoacyl)-3'-deoxyribostamycin, which is a useful antibiotic active against various drug-resistant bacteria, can be prepared advantageously by a process starting from a protected derivative of ribostamycin in the form of 1,6-carbamate and comprising the 3'-deoxygenation, the splitting of the carbamate linkage and the 1-acylation.
摘要翻译：作为抗各种药物抗性细菌的有用的抗生素的1-N-（α-取代的ω-氨基酰基）-3'-脱氧肉豆蔻霉素可以有利地通过以下形式开始制备：以保护的核糖霉素衍生物形式的1,6-氨基甲酸酯并且包含3'-脱氧，氨基甲酸酯键的分解和1-酰化。

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