KR102496552B1 - Pde10 억제제의 제조를 위한 방법 및 중간체 - Google Patents

Pde10 억제제의 제조를 위한 방법 및 중간체 Download PDF

Info

Publication number
KR102496552B1
KR102496552B1 KR1020167032983A KR20167032983A KR102496552B1 KR 102496552 B1 KR102496552 B1 KR 102496552B1 KR 1020167032983 A KR1020167032983 A KR 1020167032983A KR 20167032983 A KR20167032983 A KR 20167032983A KR 102496552 B1 KR102496552 B1 KR 102496552B1
Authority
KR
South Korea
Prior art keywords
metal
compound
formula
group
scheme
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
KR1020167032983A
Other languages
English (en)
Korean (ko)
Other versions
KR20160147275A (ko
Inventor
닐 에스. 컷샬
제니퍼 린 게이지
토마스 엘. 리틀
웨인 더글러스 루크
엘리자베스 씨.에이. 브로트
마르코 조나스
마이클 제임스 맥더모트
칼 이. 라이네케
Original Assignee
오메로스 코포레이션
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 오메로스 코포레이션 filed Critical 오메로스 코포레이션
Publication of KR20160147275A publication Critical patent/KR20160147275A/ko
Application granted granted Critical
Publication of KR102496552B1 publication Critical patent/KR102496552B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4245—Oxadiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/433—Thidiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/02—Lithium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/02—Magnesium compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
KR1020167032983A 2014-04-28 2015-04-24 Pde10 억제제의 제조를 위한 방법 및 중간체 Active KR102496552B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201461985400P 2014-04-28 2014-04-28
US61/985,400 2014-04-28
PCT/US2015/027647 WO2015167969A1 (en) 2014-04-28 2015-04-24 Processes and intermediates for the preparation of a pde10 inhibitor

Publications (2)

Publication Number Publication Date
KR20160147275A KR20160147275A (ko) 2016-12-22
KR102496552B1 true KR102496552B1 (ko) 2023-02-06

Family

ID=54359190

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020167032983A Active KR102496552B1 (ko) 2014-04-28 2015-04-24 Pde10 억제제의 제조를 위한 방법 및 중간체

Country Status (13)

Country Link
US (2) US9650368B2 (enExample)
EP (1) EP3137462B1 (enExample)
JP (1) JP6474430B2 (enExample)
KR (1) KR102496552B1 (enExample)
CN (1) CN106459026B (enExample)
AU (1) AU2015253464B2 (enExample)
BR (1) BR112016025287B1 (enExample)
CA (1) CA2946756C (enExample)
ES (1) ES2723437T3 (enExample)
IL (1) IL248585B (enExample)
NZ (2) NZ716494A (enExample)
RU (1) RU2718863C2 (enExample)
WO (1) WO2015167969A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2011224287B2 (en) * 2010-03-12 2015-03-26 Omeros Corporation PDE10 inhibitors and related compositions and methods
NZ630803A (en) * 2014-04-28 2016-03-31 Omeros Corp Optically active pde10 inhibitor
WO2017079678A1 (en) 2015-11-04 2017-05-11 Omeros Corporation Solid state forms of a pde10 inhibitor

Family Cites Families (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK178590D0 (da) 1990-07-26 1990-07-26 Novo Nordisk As 1,4-disubstituerede piperaziner
PT100905A (pt) 1991-09-30 1994-02-28 Eisai Co Ltd Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem
WO1994012461A1 (en) 1992-12-02 1994-06-09 Pfizer Inc. Catechol diethers as selective pdeiv inhibitors
DE4323192A1 (de) 1993-07-10 1995-01-12 Basf Ag Verfahren zur Herstellung von Homo- und Copolymerisaten von Alk-1-enen
DE4325846C1 (de) 1993-07-31 1995-01-19 Herberts Gmbh Verwendung von Furan-modifizierten aromatischen Pinakolderivaten als Initiatoren und Furan-modifizierte aromatische Pinakolderivate als solche
DE4343286A1 (de) 1993-12-17 1995-06-22 Hoechst Ag Heteroaromatische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen
DE4409501A1 (de) 1994-03-19 1995-09-21 Didier Werke Ag Verschleißfutter eines Schachtofens und Stein hierfür
DE69526790T2 (de) 1994-06-24 2003-03-06 Euroceltique S.A., Luxemburg/Luxembourg Verbindungen zur hemmung von phosphodiesrerase iv
US5789434A (en) 1994-11-15 1998-08-04 Bayer Corporation Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors
TW424087B (en) 1995-04-06 2001-03-01 Janssen Pharmaceutica Nv 1,3-dihydro-1-(phenylalkenyl)-2H-imidazol-2-one derivatives
TW332201B (en) 1995-04-06 1998-05-21 Janssen Pharmaceutica Nv 1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives
US6037370A (en) 1995-06-08 2000-03-14 Vertex Pharmaceuticals Incorporated Methods and compositions for stimulating neurite growth
KR19990076788A (ko) 1996-01-22 1999-10-15 후지야마 아키라 티아졸릴벤조푸란 유도체 및 그를 함유하는 약제학적 조성물
AU4015497A (en) 1996-08-26 1998-03-19 Byk Gulden Lomberg Chemische Fabrik Gmbh Thiazole derivatives useful as selective inhibitors of pde-iv
JPH1087543A (ja) 1996-09-17 1998-04-07 Chisso Corp アルコキシベンゼン誘導体、液晶組成物および液晶表示素子
US6548490B1 (en) 1997-10-28 2003-04-15 Vivus, Inc. Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction
WO1999045914A1 (en) 1998-03-13 1999-09-16 Maruho Kabushikikaisha Alkyl amine derivative and local anesthetic agent using the same
GB9807354D0 (en) 1998-04-07 1998-06-03 Glaxo Group Ltd Antiviral compound
SE9804212D0 (sv) 1998-12-04 1998-12-04 Astra Pharma Prod Compounds
PL350357A1 (en) 1999-03-12 2002-12-02 Boehringer Ingelheim Pharma Heterocyclic urea and related compounds useful as anti−inflammatory agents
US7141593B1 (en) 1999-06-04 2006-11-28 Abbott Laboratories Pharmaceutical formulations
GB9929552D0 (en) 1999-12-14 2000-02-09 Proteus Molecular Design Compounds
US7119098B2 (en) 2000-06-15 2006-10-10 Pharmacia Corporation Heteroarylakanoic acids as intergrin receptor antagonists
US20030032579A1 (en) 2001-04-20 2003-02-13 Pfizer Inc. Therapeutic use of selective PDE10 inhibitors
ES2310886T3 (es) 2001-05-22 2009-01-16 Pfizer Products Inc. Nueva forma cristalina de azitromicina.
EP1499662A1 (en) * 2002-04-18 2005-01-26 Avecia Limited Prepation of a conjugated molecule and materials for use therein
US6821502B2 (en) 2002-06-12 2004-11-23 Chevron U.S.A. Inc. Method of making aluminum-containing zeolite with IFR structure
KR20050025189A (ko) 2002-07-27 2005-03-11 아스트라제네카 아베 화학 화합물
ATE431342T1 (de) 2002-10-08 2009-05-15 Scripps Research Inst Inhibitoren von fettsäureamidhydrolase
US20060128695A1 (en) 2002-10-30 2006-06-15 Neuro3D Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses
TW200410921A (en) 2002-11-25 2004-07-01 Hoffmann La Roche Mandelic acid derivatives
JP4464280B2 (ja) 2002-12-06 2010-05-19 興和株式会社 エリスロポエチン産生促進剤
BR0317600A (pt) 2002-12-20 2005-11-29 Pharmacia Corp ácidos heteroarilalcanóicos como derivados de antagonistas de receptor de integrina
WO2004071509A1 (ja) 2003-02-12 2004-08-26 Nippon Chemiphar Co., Ltd. オリゴデンドロサイト分化促進剤
BRPI0409888A (pt) 2003-04-18 2006-05-23 Memory Pharm Corp derivados de pirazol como inibidores de fosfodiesterase 4, composto, composição farmacêutica, método para efetuar a inibição da enzima pde4, incrementar a cognição e/ou tratar a psicose em um paciente, método para o tratamento de um paciente que tem uma doença que envolve nìveis de camp diminuìdos, método para o tratamento de um paciente que sofre de uma doença alérgica ou inflamatória e método para o tratamento de um paciente que sofre de neurodegeneração resultante de uma doença ou de um ferimento
AR047541A1 (es) 2004-02-13 2006-01-25 Sandoz Ag Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas
WO2005103022A1 (en) 2004-04-20 2005-11-03 Transtech Pharma, Inc. Substituted thiazole and pyrimidine derivatives as melanocortin receptor modulators
WO2005110410A2 (en) * 2004-05-14 2005-11-24 Abbott Laboratories Kinase inhibitors as therapeutic agents
US7351833B2 (en) 2004-07-23 2008-04-01 Abbott Laboratories (1S,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate
US7449486B2 (en) * 2004-10-19 2008-11-11 Array Biopharma Inc. Mitotic kinesin inhibitors and methods of use thereof
US8436176B2 (en) 2004-12-30 2013-05-07 Medicis Pharmaceutical Corporation Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine
ATE472543T1 (de) 2005-01-07 2010-07-15 Pfizer Prod Inc Heteroaromatische chinolinverbindungen und deren verwendung als pde10-inhibitoren
KR101340859B1 (ko) 2005-02-04 2013-12-13 세노믹스, 인코포레이티드 연결형 헤테로 아릴 잔기를 포함한 화합물, 및 식용조성물을 위한 신규의 우마미 향미 개선제, 맛 촉진물질 및맛 향상제로서의 그의 용도
CA2605603A1 (en) 2005-04-22 2006-11-02 Kalypsys, Inc. Ortho-terphenyl inhibitors of p38 kinase and methods of treating inflammatory disorders
UA91546C2 (uk) 2005-05-03 2010-08-10 Бьорінгер Інгельхайм Інтернаціональ Гмбх КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ
MY152185A (en) 2005-06-10 2014-08-29 Novartis Ag Modified release 1-[(3-hydroxy-adamant-1-ylamino)-acetyl]-pyrrolidine-2(s)-carbonitrile formulation
AU2006278592A1 (en) 2005-08-04 2007-02-15 Apogee Biotechnology Corporation Sphingosine kinase inhibitors and methods of their use
RS52318B (sr) 2005-08-29 2012-12-31 Sanofi-Aventis U.S. Llc Novi kristalni oblik derivata piridazino [4,5-b] indola
EP2107066A3 (en) 2005-09-13 2009-10-21 Sicor, Inc. Processes for the synthesis of rocuronium bromide
US8637559B2 (en) 2005-11-15 2014-01-28 Otsuka Pharmaceutical Co., Ltd. Oxazole compound and pharmaceutical composition
EP1968946A4 (en) 2005-12-23 2010-05-05 Astrazeneca Ab IMIDAZOLE AS MODULATORS OF THE GABA B RECEPTOR
CA2650976A1 (en) 2006-05-02 2007-11-15 Pfizer Products Inc. Bicyclic heteroaryl compounds as pde10 inhibitors
US20080090834A1 (en) 2006-07-06 2008-04-17 Pfizer Inc Selective azole pde10a inhibitor compounds
WO2008031014A1 (en) 2006-09-08 2008-03-13 Ore Pharmaceuticals Inc. Method for reducing or alleviating inflammation in the digestive tract
CL2007002743A1 (es) 2006-09-25 2008-07-11 Pct Therapeutics Inc Soc Organ Forma cristalina del acido 3-[5-(2-fluorofenil)-[1,2,4]oxadiazol-3-il]-benzoico; composicion farmaceutica que comprende a dicha forma cristalina; y su uso para modular la terminacion prematura de traslado o decaimiento de marn, tales como carcicoma.
EP2079462A4 (en) 2006-09-28 2009-12-02 Merck & Co Inc PHARMACEUTICAL COMPOSITIONS OF HDAC INHIBITORS AND CHELABLE METAL COMPOUNDS AND METALO HDAC HEMMER CHELATE COMPLEXES
WO2008040669A2 (en) 2006-10-02 2008-04-10 Janssen Pharmaceutica N.V. Novel intermediates for the preparation of a glyt1 inhibitor
US7837978B2 (en) 2006-10-13 2010-11-23 Chevron U.S.A. Inc. Process for preparing aluminum-containing molecular sieve SSZ-26
US7786139B2 (en) 2006-11-21 2010-08-31 Omeros Corporation PDE10 inhibitors and related compositions and methods
EP2083819B1 (en) * 2006-11-21 2017-02-22 Omeros Corporation Pde10 inhibitors and related compositions and methods
PE20081506A1 (es) 2006-12-12 2008-12-09 Infinity Discovery Inc Formulaciones de ansamicina
WO2009008906A2 (en) 2007-02-06 2009-01-15 The Trustees Of The University Of Pennsylvania Therapeutic compounds for blocking dna synthesis of pox viruses
AU2008253803A1 (en) 2007-05-22 2008-11-27 Ultimorphix Technolgies B.V. Tenofovir disoproxil hemi-fumaric acid Co-crystal
EP2017264A1 (de) 2007-07-16 2009-01-21 Bayer Cropscience Ag Substituierte Phenylpropargylverbindungen, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
US20090186014A1 (en) 2007-10-10 2009-07-23 Ore Pharmaceuticals Inc. Method for treatment of pancreatitis
TW200944520A (en) 2008-01-29 2009-11-01 Glaxo Group Ltd Spiro compounds as NPY Y5 receptor antagonists
WO2009143178A2 (en) 2008-05-20 2009-11-26 Omeros Corporation Pde10 inhibitors and related compositions and methods
TWI501965B (zh) 2008-06-20 2015-10-01 Lundbeck & Co As H 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物
CN102143752B (zh) * 2008-08-05 2014-12-10 奥默罗斯公司 Pde10抑制剂以及相关组合物和方法
AU2011224287B2 (en) * 2010-03-12 2015-03-26 Omeros Corporation PDE10 inhibitors and related compositions and methods
NZ630803A (en) * 2014-04-28 2016-03-31 Omeros Corp Optically active pde10 inhibitor

Also Published As

Publication number Publication date
ES2723437T3 (es) 2019-08-27
NZ630810A (en) 2016-03-31
RU2016146118A3 (enExample) 2018-12-24
JP6474430B2 (ja) 2019-02-27
RU2718863C2 (ru) 2020-04-15
IL248585B (en) 2020-03-31
US20180057484A1 (en) 2018-03-01
AU2015253464A1 (en) 2016-10-27
EP3137462A4 (en) 2017-12-27
US9650368B2 (en) 2017-05-16
EP3137462B1 (en) 2019-01-30
US20160024069A1 (en) 2016-01-28
RU2016146118A (ru) 2018-05-30
WO2015167969A1 (en) 2015-11-05
BR112016025287A2 (pt) 2017-08-15
CN106459026B (zh) 2019-07-05
EP3137462A1 (en) 2017-03-08
KR20160147275A (ko) 2016-12-22
IL248585A0 (en) 2016-12-29
CA2946756A1 (en) 2015-11-05
CA2946756C (en) 2022-03-29
CN106459026A (zh) 2017-02-22
NZ716494A (en) 2017-07-28
BR112016025287B1 (pt) 2022-10-11
AU2015253464B2 (en) 2018-11-22
JP2017513885A (ja) 2017-06-01

Similar Documents

Publication Publication Date Title
Wang et al. GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions
US20080064876A1 (en) Process for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
TW201825491A (zh) 製備細胞凋亡誘導劑的方法
KR102496552B1 (ko) Pde10 억제제의 제조를 위한 방법 및 중간체
KR20170016894A (ko) 1,3-벤조디옥솔 헤테로사이클릭 화합물의 제조 방법
KR102558505B1 (ko) 광학 활성 pde10 저해제
JP2025016562A (ja) 含窒素ヘテロアリールカルボキサミド酢酸誘導体の製造方法
Branowska et al. Synthesis and antiprotozoal activity of 2, 5-bis [amidinoaryl] thiazoles
KR20210047320A (ko) 피롤로-아미노-피리다지논 화합물 및 이의 중간체의 제조 방법
KR20200144546A (ko) 피롤로아미노피리다지논 화합물 및 이의 중간체의 제조 방법
JP6090514B1 (ja) 重合性化合物の製造方法
Reddy et al. Ionic Liquid [EMIM] OAc under Ultrasonic Irradiation towards Synthesis of 1, 4‐DHP's
KR101674557B1 (ko) 우수한 안정성을 가지는 아조메틴 일라이드 제조방법 및 다성분 [5+2] 고리화 첨가반응을 통한 1,4-다이아제핀 유도체 제조방법
An et al. Efficient formation of C–S bond using heterocyclic thiones and arynes
Zali-Boeini et al. One-step synthesis of imidazo [1, 2-a] pyridines in water
WO2008155745A2 (en) New process for the manufacture of 1h-imidazo[4,5-c]-quinoline ring systems
KR20170080190A (ko) 1,5-쌍극자의 [5+3] 고리화 첨가 반응을 이용한 8원 헤테로 고리 화합물의 제조 방법 및 이에 의해 제조된 8원 헤테로 고리 화합물
WO2001030771A1 (en) Thiazolidinedione derivatives
CN110759846B (zh) 一种利用烯烃一锅合成多取代氮杂茂化合物的方法
JP2020158500A (ja) １，３，４−オキサ（チア）ジアゾール−２−アミン誘導体の製造法
JP2005504004A (ja) 四置換イミダゾール誘導体の製造方法およびそれの新規な結晶構造
JP2018070607A (ja) アミノ基で置換されたオキサジアゾール誘導体の製造方法
JPWO2007117009A1 (ja) ２，２−ジアルコキシエチルアミン化合物およびその製造方法
NZ538325A (en) Process for the preparation of tetrasubstituted imidazole derivatives and novel crystalline structures thereof
JP2016023158A (ja) 高純度オルメサルタンメドキソミルの製造方法

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-OTH-PR1001 (AS PROVIDED BY THE NATIONAL OFFICE)

Year of fee payment: 4