RU2662815C2 - Химический способ получения спироиндолонов и их промежуточных соединений - Google Patents

Химический способ получения спироиндолонов и их промежуточных соединений Download PDF

Info

Publication number
RU2662815C2
RU2662815C2 RU2014142621A RU2014142621A RU2662815C2 RU 2662815 C2 RU2662815 C2 RU 2662815C2 RU 2014142621 A RU2014142621 A RU 2014142621A RU 2014142621 A RU2014142621 A RU 2014142621A RU 2662815 C2 RU2662815 C2 RU 2662815C2
Authority
RU
Russia
Prior art keywords
compound
formula
polypeptide
seq
sequence
Prior art date
Application number
RU2014142621A
Other languages
English (en)
Russian (ru)
Other versions
RU2014142621A (ru
Inventor
Майкл КРОУ
Майкл ФОЛКС
Джанкарло ФРАНЧЕЗЕ
Доминик ГРИМЛЕ
Эрнст КЮСТЕРС
Курт ЛАУМЕН
Юньчжун ЛИ
Чансюэ ЛИНЬ
Йована НАЗОР
Томас РУХ
Дерек СМИТ
Шивэй СУН
Шанцзюнь ТЭН
Original Assignee
Новартис Аг
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Новартис Аг filed Critical Новартис Аг
Publication of RU2014142621A publication Critical patent/RU2014142621A/ru
Application granted granted Critical
Publication of RU2662815C2 publication Critical patent/RU2662815C2/ru

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/20—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1096—Transferases (2.) transferring nitrogenous groups (2.6)
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Enzymes And Modification Thereof (AREA)
RU2014142621A 2012-03-23 2013-03-22 Химический способ получения спироиндолонов и их промежуточных соединений RU2662815C2 (ru)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN2012000359 2012-03-23
CNPCT/CN2012/000359 2012-03-23
PCT/EP2013/056170 WO2013139987A1 (en) 2012-03-23 2013-03-22 Chemical process for preparing spiroindolones and intermediates thereof

Publications (2)

Publication Number Publication Date
RU2014142621A RU2014142621A (ru) 2016-05-20
RU2662815C2 true RU2662815C2 (ru) 2018-07-31

Family

ID=48048006

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2014142621A RU2662815C2 (ru) 2012-03-23 2013-03-22 Химический способ получения спироиндолонов и их промежуточных соединений

Country Status (21)

Country Link
US (1) US9598712B2 (enExample)
EP (2) EP3578557B1 (enExample)
JP (1) JP6117906B2 (enExample)
KR (1) KR102057590B1 (enExample)
CN (1) CN104185634B (enExample)
AP (1) AP2014007906A0 (enExample)
AU (1) AU2013237330C1 (enExample)
BR (1) BR112014022909B1 (enExample)
CA (1) CA2866222C (enExample)
CY (1) CY1122087T1 (enExample)
DK (1) DK2828256T5 (enExample)
ES (2) ES2962530T3 (enExample)
HR (1) HRP20191632T1 (enExample)
HU (1) HUE046421T2 (enExample)
LT (1) LT2828256T (enExample)
MX (1) MX354023B (enExample)
PL (1) PL2828256T3 (enExample)
PT (1) PT2828256T (enExample)
RU (1) RU2662815C2 (enExample)
SI (1) SI2828256T1 (enExample)
WO (1) WO2013139987A1 (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI784255B (zh) 2014-12-18 2022-11-21 瑞士商赫孚孟拉羅股份公司 四氫-吡啶并[3,4-b]吲哚雌激素受體調節劑及其用途
JP2017024992A (ja) * 2015-07-15 2017-02-02 公益財団法人微生物化学研究会 化合物の製造方法
LT3810283T (lt) 2018-06-21 2023-08-25 F. Hoffmann-La Roche Ag 3-((1r,3r)-1-(2,6-difluor-4-((1-(3-fluorpropil)azetidin-3- il)amino) fenil)-3-metil-1,3,4,9-tetrahidro-2h-pirido[3,4-b]indol-2-il)- 2,2- difluorpropan-1-olio tartrato druskos kietosios formos, jų paruošimo procesas ir jų naudojimo būdai vėžiui gydyti
CN111041015B (zh) * 2019-12-31 2022-03-18 浙江工业大学 一种高温下制备(r)-(+)-n-乙酰基-1-甲基-3-苯丙胺的方法
US11788071B2 (en) 2020-04-10 2023-10-17 Codexis, Inc. Engineered transaminase polypeptides
CN116209754A (zh) * 2020-09-28 2023-06-02 科德克希思公司 用于合成手性胺的工程化生物催化剂及方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB974895A (en) * 1961-04-06 1964-11-11 Parke Davis & Co Process for the production of amine compounds
US3282959A (en) * 1961-04-06 1966-11-01 Parke Davis & Co 7-chloro-alpha-methyltryptamine derivatives
US4073795A (en) * 1976-06-22 1978-02-14 Hoffmann-La Roche Inc. Synthesis of tryptophans
EP0120208A2 (de) * 1983-03-01 1984-10-03 Degussa Aktiengesellschaft Mikrobiologisch hergestellte L-Phenylalanin-Dehydrogenase, Verfahren zu ihrer Gewinnung und ihre Verwendung
EP0135846B1 (en) * 1983-09-01 1990-08-16 Genetics Institute, Inc. Production of l-amino acids by transamination
RU2007116971A (ru) * 2004-10-05 2008-11-27 Адзиномото Ко., Инк. (Jp) Способ получения производного аминокислоты из гидроксииминокислоты
WO2009132921A1 (en) * 2008-04-29 2009-11-05 Novartis Ag Spiro-indole derivatives for the treatment of parasitic diseases

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2947758A (en) * 1959-04-28 1960-08-02 Searle & Co 3-(omega-hydrazino) alkylindoles
US3183170A (en) * 1961-10-03 1965-05-11 Sanraku Ocean Kabushiki Kaisha Method of l-amino acid manufacture
BE795457A (fr) * 1972-02-16 1973-08-16 Clin Midy Amines indoliques, leur preparation et leur application en therapeutiques
US4331818A (en) * 1980-03-19 1982-05-25 The Procter & Gamble Company Chiral phospine ligand
US4518692A (en) * 1983-09-01 1985-05-21 Genetics Institute, Inc. Production of L-amino acids by transamination
US4859591A (en) * 1984-07-05 1989-08-22 W. R. Grace & Co.-Conn. Transamination process for producing amino acids
US4826766A (en) * 1985-09-23 1989-05-02 Genetics Institute, Inc. Production of amino acids using coupled aminotransferases
US7629157B2 (en) 2003-08-11 2009-12-08 Codexis, Inc. Ketoreductase polypeptides and related polynucleotides
US7541091B2 (en) 2004-05-18 2009-06-02 M & G Usa Corporation Compartmentalized resin pellets for oxygen scavenging
WO2008050207A1 (en) * 2006-10-25 2008-05-02 Pfizer Limited Heterocyclic compounds useful as anabolic agents for livestock animals
EP2132322A4 (en) 2007-03-02 2013-02-20 Richmond Chemical Corp METHOD FOR INCREASING YIELD AND IMPROVING PURIFICATION OF PRODUCTS FROM REACTIONS WITH TRANSAMINASE
AT507050B1 (de) * 2008-06-17 2010-06-15 Angewandte Biokatalyse Kompete Verfahren zur herstellung von aminen unter verwendung von omega-transaminasen
HUE036104T2 (hu) 2009-01-08 2018-06-28 Codexis Inc Transzamináz polipeptidek
JP5999565B2 (ja) * 2010-07-14 2016-09-28 ディーピーエックス ホールディングス ビー．ブイ． （ｒ）−選択的アミノ化
WO2013142770A1 (en) * 2012-03-23 2013-09-26 Codexis, Inc. Biocatalysts and methods for synthesizing derivatives of tryptamine and tryptamine analogs

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB974895A (en) * 1961-04-06 1964-11-11 Parke Davis & Co Process for the production of amine compounds
US3282959A (en) * 1961-04-06 1966-11-01 Parke Davis & Co 7-chloro-alpha-methyltryptamine derivatives
US4073795A (en) * 1976-06-22 1978-02-14 Hoffmann-La Roche Inc. Synthesis of tryptophans
EP0120208A2 (de) * 1983-03-01 1984-10-03 Degussa Aktiengesellschaft Mikrobiologisch hergestellte L-Phenylalanin-Dehydrogenase, Verfahren zu ihrer Gewinnung und ihre Verwendung
EP0135846B1 (en) * 1983-09-01 1990-08-16 Genetics Institute, Inc. Production of l-amino acids by transamination
RU2007116971A (ru) * 2004-10-05 2008-11-27 Адзиномото Ко., Инк. (Jp) Способ получения производного аминокислоты из гидроксииминокислоты
WO2009132921A1 (en) * 2008-04-29 2009-11-05 Novartis Ag Spiro-indole derivatives for the treatment of parasitic diseases

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ASANO Y ET AL, "HIGH YIELD SYNTHESIS OF L-AMINO ACIDS BY PHENYLALANINE DEHYDROGENASE FROM SPOROSARCINA UREAE", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1987, vol. 51, no. 7, 2035-2036. *
BALDWIN J E ET AL, "APPLICATION OF ESCHERICHIA-COLI ASPARTATE TRANSAMINASE TO AMINO ACID SYNTHESIS", TETRAHEDRON LETTERS, 1987, vol. 28, no. 32, pages 3745 - 3746 *
IWAO TABUSHI ET AL, "A-(modified B6)-B-[omega-amino(ethylamino)]-beta-cyclodextrin as an artificial B6 enzyme for chiral aminotransfer reaction", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, vol. 107, no. 19, pages 5545 - 5546. *
NICHOLS D E ET AL, "SYNTHESIS AND SEROTONIN RECEPTOR AFFINITIES OF A SERIES OF ENANTIOMERS OF ALPHA-METHYLTRYPTAMINES: EVIDENCE FOR THE BINDING CONFORMATION OF TRYPTAMINES AT SEROTONIN 5-HT1B RECEPTORS", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, 1988, vol. 31, no. 7, pages 1406 - 1412. *
NICHOLS D E ET AL, "SYNTHESIS AND SEROTONIN RECEPTOR AFFINITIES OF A SERIES OF ENANTIOMERS OF ALPHA-METHYLTRYPTAMINES: EVIDENCE FOR THE BINDING CONFORMATION OF TRYPTAMINES AT SEROTONIN 5-HT1B RECEPTORS", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, 1988, vol. 31, no. 7, pages 1406 - 1412. IWAO TABUSHI ET AL, "A-(modified B6)-B-[omega-amino(ethylamino)]-beta-cyclodextrin as an artificial B6 enzyme for chiral aminotransfer reaction", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, vol. 107, no. 19, pages 5545 - 5546. BALDWIN J E ET AL, "APPLICATION OF ESCHERICHIA-COLI ASPARTATE TRANSAMINASE TO AMINO ACID SYNTHESIS", TETRAHEDRON LETTERS, 1987, vol. 28, no. 32, pages 3745 - 3746ASANO Y ET AL, "HIGH YIELD SYNTHESIS OF L-AMINO ACIDS BY PHENYLALANINE DEHYDROGENASE FROM SPOROSARCINA UREAE", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1987, vol. 51, no. 7, 2035-2036. ASANO Y ET AL, "HIGH YIELD SYNTHESIS OF L-AMINO ACIDS BY PHENYLALANINE DEHYDROGENASE FROM SPOROSARCINA UREAE", AGRICULTU *

Also Published As

Publication number Publication date
CN104185634A (zh) 2014-12-03
ES2748460T3 (es) 2020-03-16
EP3578557A1 (en) 2019-12-11
SI2828256T1 (sl) 2019-11-29
PL2828256T3 (pl) 2019-12-31
AU2013237330C1 (en) 2016-08-25
AP2014007906A0 (en) 2014-08-31
DK2828256T5 (da) 2019-12-09
LT2828256T (lt) 2019-09-25
EP3578557B1 (en) 2023-09-20
KR20140137374A (ko) 2014-12-02
PT2828256T (pt) 2019-10-18
HUE046421T2 (hu) 2020-02-28
JP2015512381A (ja) 2015-04-27
EP2828256A1 (en) 2015-01-28
WO2013139987A1 (en) 2013-09-26
BR112014022909B1 (pt) 2021-11-03
DK2828256T3 (da) 2019-10-07
HK1202289A1 (en) 2015-09-25
BR112014022909A2 (pt) 2017-07-18
CN104185634B (zh) 2017-05-03
HRP20191632T1 (hr) 2019-12-13
CY1122087T1 (el) 2020-11-25
ES2962530T3 (es) 2024-03-19
AU2013237330A1 (en) 2014-09-25
MX354023B (es) 2018-02-08
US9598712B2 (en) 2017-03-21
EP2828256B1 (en) 2019-07-03
MX2014011489A (es) 2015-05-11
AU2013237330B2 (en) 2015-12-03
US20150045562A1 (en) 2015-02-12
JP6117906B2 (ja) 2017-04-19
CA2866222C (en) 2022-01-11
KR102057590B1 (ko) 2019-12-19
RU2014142621A (ru) 2016-05-20
CA2866222A1 (en) 2013-09-26

Similar Documents

Publication Publication Date Title
JP5999565B2 (ja) （ｒ）−選択的アミノ化
DK2828385T3 (en) BIOCATALIZATORS AND METHODS FOR SYNTHETIZING DERIVATIVES AND TRYPTAMIN AND TRYPTAMINE ANALOGS
CA2895752C (en) Engineered biocatalysts and methods for synthesizing chiral amines
EP3578557B1 (en) Chemical process for preparing spiroindolones and intermediates thereof
JP7402157B2 (ja) 操作されたポリペプチドおよびβ－ヒドロキシ－α－アミノ酸合成におけるそれらの用途
JP7726528B2 (ja) 操作された酢酸キナーゼバリアント酵素
EP3630795B1 (en) Engineered aldolase polypeptides and uses thereof
EP4217502A1 (en) Engineered biocatalysts and methods for synthesizing chiral amines
JP2022518212A (ja) 操作されたトランスアミナーゼポリペプチド
HK40013831B (en) Chemical process for preparing spiroindolones and intermediates thereof
HK40013831A (en) Chemical process for preparing spiroindolones and intermediates thereof
HK1202289B (en) Chemical process for preparing spiroindolones and intermediates thereof
HK1185919A (en) (r)-selective amination