MA45155B1 - Procédés de préparation d'oligomères morpholino de phosphorodiamidate - Google Patents

Procédés de préparation d'oligomères morpholino de phosphorodiamidate

Info

Publication number
MA45155B1
MA45155B1 MA45155A MA45155A MA45155B1 MA 45155 B1 MA45155 B1 MA 45155B1 MA 45155 A MA45155 A MA 45155A MA 45155 A MA45155 A MA 45155A MA 45155 B1 MA45155 B1 MA 45155B1
Authority
MA
Morocco
Prior art keywords
phosphorodiamidate
processes
preparation
oligomer
morpholino oligomers
Prior art date
Application number
MA45155A
Other languages
English (en)
Other versions
MA45155A (fr
Inventor
Bao Cai
Mitchell MARTINI
Katie THOMAS
Ross SHIMABUKU
Original Assignee
Sarepta Therapeutics, Inc.
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 Sarepta Therapeutics, Inc. filed Critical Sarepta Therapeutics, Inc.
Publication of MA45155A publication Critical patent/MA45155A/fr
Publication of MA45155B1 publication Critical patent/MA45155B1/fr

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/062Organo-phosphoranes without P-C bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C07F9/65616Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/66Phosphorus compounds
    • A61K31/675Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des procédés de préparation d'un oligomère (par exemple, un oligomère morpholino). Les procédés de synthèse décrits ici peuvent être avantageux pour la mise à l'échelle de la synthèse d'oligomères tout en maintenant le rendement global et la pureté d'un oligomère synthétisé.
MA45155A 2016-05-24 2017-05-24 Procédés de préparation d'oligomères morpholino de phosphorodiamidate MA45155B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201662340953P 2016-05-24 2016-05-24
US201662357134P 2016-06-30 2016-06-30
EP17731337.6A EP3464306B1 (fr) 2016-05-24 2017-05-24 Procédés de préparation d'oligomères morpholino de phosphorodiamidate
PCT/US2017/034284 WO2017205513A1 (fr) 2016-05-24 2017-05-24 Procédés de préparation d'oligomères morpholino de phosphorodiamidate

Publications (2)

Publication Number Publication Date
MA45155A MA45155A (fr) 2019-04-10
MA45155B1 true MA45155B1 (fr) 2024-06-28

Family

ID=59078166

Family Applications (2)

Application Number Title Priority Date Filing Date
MA45155A MA45155B1 (fr) 2016-05-24 2017-05-24 Procédés de préparation d'oligomères morpholino de phosphorodiamidate
MA71469A MA71469A (fr) 2016-05-24 2017-05-24 Procédé de préparation d'oligomères morpholino de phosphorodiamidate

Family Applications After (1)

Application Number Title Priority Date Filing Date
MA71469A MA71469A (fr) 2016-05-24 2017-05-24 Procédé de préparation d'oligomères morpholino de phosphorodiamidate

Country Status (28)

Country Link
US (3) US10961262B2 (fr)
EP (2) EP4406600A3 (fr)
JP (1) JP6987081B2 (fr)
KR (1) KR102504759B1 (fr)
CN (1) CN109311920B (fr)
AU (1) AU2017271524B2 (fr)
BR (1) BR112018074270B1 (fr)
CA (1) CA3024182A1 (fr)
CO (1) CO2018013827A2 (fr)
DK (1) DK3464306T3 (fr)
ES (1) ES2987586T3 (fr)
FI (1) FI3464306T3 (fr)
HR (1) HRP20240583T1 (fr)
HU (1) HUE066393T2 (fr)
IL (1) IL263033B2 (fr)
LT (1) LT3464306T (fr)
MA (2) MA45155B1 (fr)
MD (1) MD3464306T2 (fr)
MX (1) MX383656B (fr)
PL (1) PL3464306T3 (fr)
PT (1) PT3464306T (fr)
RS (1) RS65504B1 (fr)
SA (1) SA518400462B1 (fr)
SG (1) SG11201809499UA (fr)
SI (1) SI3464306T1 (fr)
SM (1) SMT202400183T1 (fr)
TW (1) TWI737736B (fr)
WO (1) WO2017205513A1 (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI541024B (zh) 2010-09-01 2016-07-11 日本新藥股份有限公司 反義核酸
BR112018074346B1 (pt) * 2016-05-24 2023-01-03 Sarepta Therapeutics, Inc. Composto oligomérico e processo para preparar um composto oligomérico
US11472824B2 (en) 2016-05-24 2022-10-18 Sarepta Therapeutics, Inc. Processes for preparing phosphorodiamidate morpholino oligomers
CA3024456A1 (fr) 2016-05-24 2017-11-30 Sarepta Therapeutics, Inc. Procedes de preparation d'oligomeres morpholino de phosphorodiamidate
US10947533B2 (en) 2016-05-24 2021-03-16 Sarepta Therapeutics, Inc. Processes for preparing phosphorodiamidate morpholino oligomers
MD3464306T2 (ro) * 2016-05-24 2024-08-31 Sarepta Therapeutics Inc Procedee de preparare a oligomerilor morfolino fosforodiamidați
KR102523522B1 (ko) * 2016-06-30 2023-04-20 사렙타 쎄러퓨틱스 인코퍼레이티드 포스포로디아미데이트 모르폴리노 올리고머의 제조 방법
KR102523527B1 (ko) * 2016-06-30 2023-04-20 사렙타 쎄러퓨틱스 인코퍼레이티드 포스포로디아미데이트 모르폴리노 올리고머의 제조 방법
WO2019060862A1 (fr) * 2017-09-25 2019-03-28 Sarepta Therapeutics, Inc. Procédés de préparation d'oligomères morpholino phosphorodiamidate par l'intermédiaire d'une synthèse à flux rapide
US11168141B2 (en) 2018-08-02 2021-11-09 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating dystrophinopathies
CA3108282A1 (fr) 2018-08-02 2020-02-06 Dyne Therapeutics, Inc. Complexes de ciblage musculaire et leurs utilisations pour le traitement de dystrophinopathies
CN109704980B (zh) * 2019-02-16 2022-05-13 安徽大学 一种(z)-3-氨基-2-(2-氟-3-甲氧基苯基)-2-丁烯酸乙酯的制备方法
EP4123023A4 (fr) * 2020-03-16 2024-07-17 National University Corporation Tokyo Medical and Dental University Acide hétéro-nucléique contenant un acide nucléique morpholino
JP2024525608A (ja) 2021-07-09 2024-07-12 ダイン セラピューティクス,インコーポレーテッド ジストロフィン異常症を処置するための筋標的化複合体および製剤
US11969475B2 (en) 2021-07-09 2024-04-30 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating facioscapulohumeral muscular dystrophy
US11771776B2 (en) 2021-07-09 2023-10-03 Dyne Therapeutics, Inc. Muscle targeting complexes and uses thereof for treating dystrophinopathies
AU2022377070A1 (en) * 2021-11-01 2024-04-11 Dyne Therapeutics, Inc. Muscle targeting complexes for treating dystrophinopathies

Family Cites Families (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5185444A (en) 1985-03-15 1993-02-09 Anti-Gene Deveopment Group Uncharged morpolino-based polymers having phosphorous containing chiral intersubunit linkages
WO1986005519A1 (fr) 1985-03-15 1986-09-25 James Summerton Reactif et procede d'analyse de polynucleotides
US5217866A (en) 1985-03-15 1993-06-08 Anti-Gene Development Group Polynucleotide assay reagent and method
US5166315A (en) 1989-12-20 1992-11-24 Anti-Gene Development Group Sequence-specific binding polymers for duplex nucleic acids
US5034506A (en) 1985-03-15 1991-07-23 Anti-Gene Development Group Uncharged morpholino-based polymers having achiral intersubunit linkages
US5521063A (en) 1985-03-15 1996-05-28 Antivirals Inc. Polynucleotide reagent containing chiral subunits and methods of use
US5506337A (en) 1985-03-15 1996-04-09 Antivirals Inc. Morpholino-subunit combinatorial library and method
WO1990002749A1 (fr) 1988-09-01 1990-03-22 Forskningscenter Risø Procede de synthese de peptides et support solide de realisation dudit procede
CN1046724C (zh) * 1993-12-29 1999-11-24 藤泽药品工业株式会社 吡唑并吡啶化合物、含有它们的药物组合物、及其制法与用途
US6794499B2 (en) 1997-09-12 2004-09-21 Exiqon A/S Oligonucleotide analogues
US7572582B2 (en) 1997-09-12 2009-08-11 Exiqon A/S Oligonucleotide analogues
US7084125B2 (en) 1999-03-18 2006-08-01 Exiqon A/S Xylo-LNA analogues
US7053207B2 (en) 1999-05-04 2006-05-30 Exiqon A/S L-ribo-LNA analogues
US6784291B2 (en) 2000-05-04 2004-08-31 Avi Biopharma, Inc. Splice-region antisense composition and method
CA2459347C (fr) 2001-09-04 2012-10-09 Exiqon A/S Compositions d'acides nucleiques bloques et leurs utilisations
US7569575B2 (en) 2002-05-08 2009-08-04 Santaris Pharma A/S Synthesis of locked nucleic acid derivatives
AU2003287464A1 (en) 2002-11-05 2004-06-03 Isis Pharmaceuticals, Inc. 2'-fluoro substituted oligomeric compounds and compositions for use in gene modulations
US7759513B2 (en) 2003-02-21 2010-07-20 Nigu Chemie Gmbh Photolabile protective groups for improved processes to prepare oligonucleotide arrays
EP2933332A1 (fr) 2004-06-28 2015-10-21 The University Of Western Australia Oligonucléotides antisens permettant d'induire un saut d'exon et leurs procédés d'utilisation
US8067571B2 (en) 2005-07-13 2011-11-29 Avi Biopharma, Inc. Antibacterial antisense oligonucleotide and method
US9371348B2 (en) 2006-11-27 2016-06-21 The Trustees Of The University Of Pennsylvania Photocleavable oligonucleotide and uses thereof
US8299206B2 (en) 2007-11-15 2012-10-30 Avi Biopharma, Inc. Method of synthesis of morpholino oligomers
RU2606627C2 (ru) 2007-11-15 2017-01-10 Серепта Терапьютикс,Инк. Способ синтеза морфолиновых олигомеров
US8076476B2 (en) 2007-11-15 2011-12-13 Avi Biopharma, Inc. Synthesis of morpholino oligomers using doubly protected guanine morpholino subunits
CA2758189C (fr) 2009-04-10 2020-12-29 Association Institut De Myologie Oligonucleotides antisens tricyclo-adn, compositions, et methodes de traitement de maladies
TR201816523T4 (tr) 2009-11-12 2018-11-21 Univ Western Australia Patolojilerin tedavisine yönelik antisens moleküller ve yöntemler.
KR20200133284A (ko) * 2010-05-28 2020-11-26 사렙타 쎄러퓨틱스, 인코퍼레이티드 변형된 서브유니트간 결합 및/또는 말단 그룹을 갖는 올리고뉴클레오타이드 유사체
TWI463423B (zh) * 2010-05-28 2014-12-01 Poynt Corp 用以針對基於三維形狀之廣告系統使用位置資訊的方法
TWI541024B (zh) 2010-09-01 2016-07-11 日本新藥股份有限公司 反義核酸
ES2607603T3 (es) 2010-09-30 2017-04-03 Nippon Shinyaku Co., Ltd. Derivado de ácido morfolino nucleico
EP2672977A1 (fr) * 2011-02-08 2013-12-18 The Charlotte-Mecklenburg Hospital Authority d/b/a Carolina Healthcare System Oligonucléotides antisens
EP2748176B1 (fr) 2011-08-23 2019-04-17 The Royal Institution for the Advancement of Learning / McGill University Marqueurs ioniques pour la synthèse d'oligoribonucléotides
PL2581448T3 (pl) 2011-10-13 2015-08-31 Association Inst De Myologie Tricyklo-tiofosforanowy DNA
HK1201514A1 (en) 2011-11-18 2015-09-04 Sarepta Therapeutics, Inc. Functionally-modified oligonucleotides and subunits thereof
JP6496549B2 (ja) * 2011-11-30 2019-04-03 サレプタ セラピューティクス, インコーポレイテッド 脊髄性筋萎縮症における誘発されたエクソン包含
CA2861247C (fr) * 2011-12-28 2021-11-16 Nippon Shinyaku Co., Ltd. Acide nucleique antisens
WO2013128281A1 (fr) 2012-02-28 2013-09-06 Population Genetics Technologies Ltd Procédé de fixation d'une contre-séquence à un échantillon d'acides nucléiques
CN102702265A (zh) * 2012-05-14 2012-10-03 天津特安化学科技有限公司 一种固相合成磷酰二胺吗啉代寡核苷酸及方法
CN110218727A (zh) * 2013-03-14 2019-09-10 萨勒普塔医疗公司 用于治疗肌营养不良的外显子跳跃组合物
US20140315977A1 (en) * 2013-03-14 2014-10-23 Sarepta Therapeutics, Inc. Exon skipping compositions for treating muscular dystrophy
US8999152B2 (en) * 2013-03-15 2015-04-07 Uop Llc Process and apparatus for recovering and blending hydroprocessed hydrocarbons and composition
US20140329762A1 (en) 2013-03-15 2014-11-06 Sarepta Therapeutics, Inc. Compositions for treating muscular dystrophy
DK3015467T3 (da) 2013-05-24 2025-02-10 Ajinomoto Kk Morpholino-oligonukleotidfremstillingsfremgangsmåde
BR112018074346B1 (pt) * 2016-05-24 2023-01-03 Sarepta Therapeutics, Inc. Composto oligomérico e processo para preparar um composto oligomérico
MD3464306T2 (ro) 2016-05-24 2024-08-31 Sarepta Therapeutics Inc Procedee de preparare a oligomerilor morfolino fosforodiamidați
CA3024456A1 (fr) 2016-05-24 2017-11-30 Sarepta Therapeutics, Inc. Procedes de preparation d'oligomeres morpholino de phosphorodiamidate
US11472824B2 (en) 2016-05-24 2022-10-18 Sarepta Therapeutics, Inc. Processes for preparing phosphorodiamidate morpholino oligomers
US10947533B2 (en) * 2016-05-24 2021-03-16 Sarepta Therapeutics, Inc. Processes for preparing phosphorodiamidate morpholino oligomers
KR102810425B1 (ko) 2016-12-19 2025-05-21 사렙타 쎄러퓨틱스 인코퍼레이티드 근육 이상증에 대한 엑손 스킵핑 올리고머 결합체

Also Published As

Publication number Publication date
BR112018074270B1 (pt) 2021-02-02
CA3024182A1 (fr) 2017-11-30
TW201825506A (zh) 2018-07-16
PL3464306T3 (pl) 2024-07-22
IL263033A (en) 2018-12-31
KR102504759B1 (ko) 2023-02-28
KR20190013844A (ko) 2019-02-11
SI3464306T1 (sl) 2024-08-30
FI3464306T3 (fi) 2024-05-16
SMT202400183T1 (it) 2024-07-09
SG11201809499UA (en) 2018-12-28
MA71469A (fr) 2025-04-30
EP3464306A1 (fr) 2019-04-10
HUE066393T2 (hu) 2024-07-28
AU2017271524A1 (en) 2018-11-15
MD3464306T2 (ro) 2024-08-31
US10961262B2 (en) 2021-03-30
BR112018074270A2 (pt) 2019-03-12
US12258362B2 (en) 2025-03-25
MX383656B (es) 2025-03-14
TWI737736B (zh) 2021-09-01
US20190276480A1 (en) 2019-09-12
ES2987586T3 (es) 2024-11-15
EP4406600A2 (fr) 2024-07-31
SA518400462B1 (ar) 2022-06-12
JP2019523754A (ja) 2019-08-29
AU2017271524B2 (en) 2021-06-24
EP3464306B1 (fr) 2024-03-27
HRP20240583T1 (hr) 2024-07-19
US20250276988A1 (en) 2025-09-04
EP4406600A3 (fr) 2024-10-30
US20220340605A1 (en) 2022-10-27
WO2017205513A1 (fr) 2017-11-30
CN109311920A (zh) 2019-02-05
IL263033B (en) 2022-10-01
RS65504B1 (sr) 2024-06-28
JP6987081B2 (ja) 2021-12-22
MA45155A (fr) 2019-04-10
LT3464306T (lt) 2024-05-10
DK3464306T3 (da) 2024-05-21
MX2018014162A (es) 2019-04-01
PT3464306T (pt) 2024-05-17
CO2018013827A2 (es) 2018-12-28
IL263033B2 (en) 2023-02-01
CN109311920B (zh) 2021-11-09

Similar Documents

Publication Publication Date Title
MA45155B1 (fr) Procédés de préparation d'oligomères morpholino de phosphorodiamidate
MA45154B1 (fr) Procédés de préparation d'oligomères
MX390906B (es) Procesos para preparar oligómeros de morfolino fosforodiamidato.
ZA202403308B (en) An efficient new process for synthesis of 2-amino-5-chloro-n-,3-dimethylbenzamide
MA51204B1 (fr) Formes pharmaceutiques comprenant un inhibiteur de la kallicréine plasmatique
SA518400463B1 (ar) عمليات لتحضير أوليجومرات فوسفوروداي أميدات مورفولينو
WO2016141296A8 (fr) Inhibiteurs de kinases tricycliques de melk et procédés d'utilisation
TN2018000393A1 (en) Pegylated carfilzomib compounds
MA68842B1 (fr) Procédé de conjugaison de cys-mabs
WO2018039629A3 (fr) Acides nucléiques sphériques micellaires obtenus à partir de matrices thermosensibles sans trace
PH12021550639A1 (en) Synthesis of 2`-Fluoro-6`-Methylene-Carbocyclic Adenosine (FMCA) and 2`-Fluoro-6`-Methylene-Carbocyclic Guanosine (FMCG)
JOP20210157B1 (ar) تخليق 3-ميثيل-1، 2، 4-ثياديازول-5-كربوهيدرازيد أو ميثيل-d3 مُعَالَج بالديوتيريوم منه
CO2018013831A2 (es) Procesos para preparar oligómeros de morfolino fosforodiamidato
WO2017112809A8 (fr) Système et procédé de synthèse de peptides gap en phase solution
MY140739A (en) 2, 6-quinolinyl derivatives, processes for preparing them and their uses
MA49986A (fr) Procédés de préparation d'oligomères morpholino phosphorodiamidate par l'intermédiaire d'une synthèse à flux rapide
MX2022001549A (es) Nuevas sintesis telescopicas de 2-metoximetil-p-fenilendiamina.
MX2022006142A (es) Proceso para la sintesis de (3-cloro-2-piridil)hidrazina.
MX2020005168A (es) Formas de dosificacion que contienen un inhibidor calicreina de plasma.
CL2014001043A1 (es) Procedimiento para preparar un compuesto intermediario en la ruta de sintesis de tmc 435, inhibidor de proteasa, útil en el tratamiento de la hepatitis c.
WO2015159170A3 (fr) Procédé amélioré pour la synthèse de 1-(4-méthoxyphényl) éthylamine et ses isomères
DE60329721D1 (de) Regiospezifische synthese von nikotinderivaten
SA519410561B1 (ar) عوامل صيدلية، تركيبات، وطرق تتعلق بذلك
EA200802065A1 (ru) Синтез замещённых флуоренов
WO2019191363A3 (fr) Synthèse rapide d'oseltamivir et de composés apparentés par réaction de diazidation-diamidification directe d'oléfines