DK2900634T3 - Fremgangsmåde til fremstilling af eventuelt substituerede phenyl- og pyridylpyrrolidiner - Google Patents

Fremgangsmåde til fremstilling af eventuelt substituerede phenyl- og pyridylpyrrolidiner Download PDF

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Publication number
DK2900634T3
DK2900634T3 DK13766333.2T DK13766333T DK2900634T3 DK 2900634 T3 DK2900634 T3 DK 2900634T3 DK 13766333 T DK13766333 T DK 13766333T DK 2900634 T3 DK2900634 T3 DK 2900634T3
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formula
compounds
iii
alkyl
above meanings
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DK13766333.2T
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Friedrich August Mühlthau
Mark James Ford
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Bayer Cropscience Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
    • C07C317/10—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
    • C07C323/02—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/07—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (7)

1. Fremgangsmåde til fremstilling af forbindelser med formel (X)
hvor Z er C-X3 eller et nitrogenatom, X1, X2, X3, X4 og X5 uafhængigt af hinanden er udvalgt fra gruppen, der består af hydrogen, halogen, cyano, Ci-Ci2_alkyl, Ci-Ci2-halogenalkyl, Ci-Ci2-alkoxy og Ci-Ci2-halogenalkoxy; der omfatter trin (i): reaktion af forbindelser med formel (II)
hvori X1, X2, X4, X5 og Z har ovennævnte betydninger, med forbindelser med formel (III) T -CH2-S (0)mR (III) hvori T er ( (Ci-4)-alkylO) 2P(0) eller A-(C6H5)3P+; A~ er chlorid, bromid eller iodid; R er Ci-12-alkyl, Ci-6-halogenalkyl, phenyl eller phenyl-Ci-6-alkyl; m er 0, 1 eller 2; eventuelt i nærvær af et opløsningsmiddel, i nærvær af en base, og hvis T er A~(C6H5)3P+ eventuelt i nærvær af en faseoverføringskatalysator eller et opløsningsmiddel, og hvis T er ( (C1-4)-alkylO) 2P (0) eventuelt i nærvær af en Lewis-syre til opnåelse af forbindelser med formel (IV)
hvori X1, X2, X4, X5, R, m og Z har ovennævnte betydninger, trin (ii): reaktion af forbindelser med formel (IV) (ii-a) med forbindelser med formel (V)
hvori R1 er udvalgt fra gruppen, der består af C:-:2-alkyl, Ci-6-halogenalkyl, phenyl, og phenyl-Ci-6-alkyl; R2, R3 og R4 uafhængigt af hinanden er udvalgt fra gruppen, der består af Ci-12-alkyl, Ci-6-halogenalkyl, phenyl og phenyl-Ci-6-alkyl; Q er udvalgt fra gruppen, der består af aryl-Ci-C6-alkyl, C1-C6-alkoxy-(Ci-Cs)-alkyl, Ci-C6-alkyl- (O-CH2) n og C2-C6-alkenyl; n er 1 til 10; i nærvær af en syre eller eat fluoridsalt; eller (ii-b) med forbindelser med formel (Va)
hvori Q har ovennævnte betydninger, i nærvær af formaldehyd eller en formaldehydækvivalent udvalgt fra gruppen, der består af trioxan og paraformaldehyd, og i nærvær af en opløsningsmiddel, i hvilken fremgangsmåde vandet, der dannes under reaktionen, fjernes fra reaktionsblandingen, til opnåelse af forbindelser med formel (VI)
hvori X1, X2, X4, X5, R, m, Q og Z har ovennævnte betydninger, der omdannes til forbindelser med formel (I)
hvori X1, X2, X4, X5, Q og Z har ovennævnte betydninger, ved hjælp af (trin (iii-a)) opvarmning af forbindelser med formel (VI), hvori m er 1, eventuelt i nærvær af en base, hvis passende i nærvær af et opløsningsmiddel (trin (iii-a-1)), til opnåelse af forbindelser med formel (VII)
hvori X1, X2, X4, X5, Q og Z har ovennævnte betydninger, der udsættes for en katalytisk hydrogenering eller for en reduktionsreaktion ved anvendelse af en hydridkilde i et passende opløsningsmiddel (trin (iii-a-2)), eller ved hjælp af (trin (iii-b)) fjernelse af S (0) mR-gruppen ved reaktion af forbindelser med formel (VI), hvori m er 2, med et frit metal i nærvær af et opløsningsmiddel og fortrinsvis i nærvær af metalsalte; eller ved hjælp af (trin (iii-c)) fjernelse af S (0)mR-gruppen fra forbindelser med formel (VI), hvori m er 0 eller 1, ved hjælp af katalytisk hydrogenering i nærvær af et opløsningsmiddel og eventuelt en base eller en syre og trin (iv) erstatning af gruppe Q med hydrogen til opnåelse af forbindelser med formel (X) eller reaktion af forbindelser med formel (IV) (trin (ii-aa)) med forbindelser med formel (V-l) hvori
R1, R2, R3 og R4 har ovennævnte betydninger, og Q1 er udvalgt fra gruppen, der består af Ci-C6-alkyl-(O-CH2) n, eller R1 og Q1 sammen med atomerne, hvortil de er bundet, danner en ring udvalgt blandt
hvor den stiplede linje er bindingen til carbonatomet, der støder op til Si-atomet i formel (V-l); i nærvær af en syre eller et fluoridsalt til opnåelse af forbindelser med formel (Via)
hvori X1, X2, X4, X5, R, m og Z har ovennævnte betydninger, der omdannes til forbindelser med formel (X) ved hjælp af (trin (iii-aa) ) opvarmning af forbindelser med formel (Via), hvori m er 1, eventuelt i nærvær af en base, hvis passende i nærvær af et opløsningsmiddel (trin (iii-aa-1)), til opnåelse af forbindelser med formel (Vila)
hvori X1, X2, X4, X5 og Z har ovennævnte betydninger, der udsættes for en katalytisk hydrogenering eller for en reduktionsreaktion ved anvendelse af en hydridkilde i et passende opløsningsmiddel (trin (iii-aa-2)).
2. Forbindelser med formel (IV)
hvori X1, X2, Z, X4, X5, R og m har ovennævnte betydninger, forudsat at én af X1, X2, X4 og X5 ikke er hydrogen.
3. Forbindelser med formel E-(IV)
hvori X1, X2, Z, X4, X5, R og m har ovennævnte betydninger, forudsat at én af X1, X2, X4 og X5 ikke er hydrogen.
4. Forbindelser med formel Z-(IV)
hvori X1, X2, Z, X4, X5, R og m har ovennævnte betydninger, forudsat at én af X1, X2, X4 og X5 ikke er hydrogen.
5. Forbindelser med formel (V-l)
hvori R1, R2, R3, R4 og Q1 har ovennævnte betydninger.
6. Forbindelser med formel
hvori R2, R3 og R4 har ovennævnte betydninger.
7. Forbindelser med formel
hvori R2, R3 og R4 har ovennævnte betydninger.
DK13766333.2T 2012-09-27 2013-09-25 Fremgangsmåde til fremstilling af eventuelt substituerede phenyl- og pyridylpyrrolidiner DK2900634T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12186243 2012-09-27
PCT/EP2013/069919 WO2014048958A1 (en) 2012-09-27 2013-09-25 Process for the preparation of optionally substituted phenyl and pyridyl pyrrolidines

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US (1) US9447036B2 (da)
EP (1) EP2900634B1 (da)
JP (1) JP6251749B2 (da)
KR (1) KR20150059778A (da)
CN (1) CN104619683B (da)
BR (1) BR112015006825A2 (da)
DK (1) DK2900634T3 (da)
ES (1) ES2625547T3 (da)
IL (1) IL237749A (da)
IN (1) IN2015DN02542A (da)
MX (1) MX350575B (da)
TW (1) TWI601713B (da)
WO (1) WO2014048958A1 (da)

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EP3649101B1 (en) * 2017-08-09 2021-03-24 Lonza Solutions AG Method for the preparation of 4-(heptafluoro-2-propyl) anilines

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4092349A (en) 1976-11-10 1978-05-30 Pfizer Inc. 11-Desoxy-15-thiaprostaglandins
US4173463A (en) 1978-10-31 1979-11-06 Shell Oil Company Phosphonium salts as herbicides
EP0393424B1 (de) 1989-04-17 1995-09-27 Bayer Ag Verfahren zur Herstellung von 2,7-Diazabicyclo(3.3.0)octanen
IT1274021B (it) 1994-02-28 1997-07-14 Italfarmaco Spa Diesteri dell'acido carbonico ad attivita' antivirale ed antinfiammatoria
WO1997019038A1 (fr) 1995-11-23 1997-05-29 Rhodia Chimie Procede utile pour la perfluoroalcoylation et reactif pour mettre en oeuvre ce procede
JP2000516234A (ja) * 1996-08-16 2000-12-05 デュポン ファーマシューティカルズ カンパニー アミジノフェニル―ピロリジン類、アミジノフェニル―ピロリン類、およびアミジノフェニル―イソオキサゾリジン類およびそれらの誘導体
US7138530B2 (en) 2002-05-28 2006-11-21 3-Dimensional Pharmaceuticals, Inc. Thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions
US7230119B2 (en) 2004-08-25 2007-06-12 Biocryst Pharmaceuticals, Inc. Process for the preparation of substituted pyrrolidine derivatives and intermediates
US7521427B2 (en) 2004-11-09 2009-04-21 Georgia Tech Research Corporation Peptidyl allyl sulfones
AR057032A1 (es) 2005-05-27 2007-11-14 Wyeth Corp Tigeciclina y metodos de preparacion
WO2007015157A2 (en) 2005-08-01 2007-02-08 Pfizer Limited Mc4r-ag0nists for the treatment of urinary tract dysfunction
US7750167B2 (en) 2006-07-05 2010-07-06 N.V. Organon Process for the preparation of asenapine and intermediate products used in said process
JP5164510B2 (ja) * 2006-10-06 2013-03-21 日本曹達株式会社 含窒素複素環化合物および有害生物防除剤
GB0623209D0 (en) 2006-11-21 2007-01-03 F2G Ltd Antifungal agents
WO2008129811A1 (ja) 2007-03-23 2008-10-30 Panasonic Corporation 無線送信装置及び無線受信装置
JP2008266230A (ja) 2007-04-23 2008-11-06 Bayer Cropscience Ag 殺虫性アリールピロリジン類
JP2010116389A (ja) 2008-10-17 2010-05-27 Bayer Cropscience Ag 殺虫性アリールピロリジン類
WO2009087058A1 (en) 2008-01-04 2009-07-16 N.V. Organon Process for the preparation of asenapine and intermediate products used in said process
CZ305085B6 (cs) 2008-03-14 2015-04-29 Zentiva, K.S. Způsob přípravy dabigatranu
WO2010086820A1 (en) 2009-02-02 2010-08-05 Pfizer Inc. 4-amino-5-oxo-7, 8-dihydropyrimido [5,4-f] [1,4] oxazepin-6 (5h) -yl) phenyl derivatives, pharmaceutical compositions and uses thereof
PT2401267E (pt) 2009-02-27 2014-04-10 Ambit Biosciences Corp Derivados de quinazolina moduladores de quinase jak e sua utilização em métodos
CN102414175A (zh) 2009-04-30 2012-04-11 拜耳作物科学公司 杀虫的芳基吡咯烷
SG176100A1 (en) * 2009-05-22 2011-12-29 Abbott Lab Modulators of 5-ht receptors and methods of use thereof
KR20120037993A (ko) 2009-07-16 2012-04-20 바이엘 크롭사이언스 아게 키랄 3-트리아졸릴 설폭사이드 유도체의 제조방법
JP2011136928A (ja) 2009-12-28 2011-07-14 Bayer Cropscience Ag 殺虫性アリールピロリジン類
JP2012082186A (ja) 2010-09-15 2012-04-26 Bayer Cropscience Ag 殺虫性アリールピロリジン類
AU2013312896A1 (en) * 2012-09-07 2015-02-26 Zoetis Services Llc Spirocyclic derivatives as antiparasitic agents

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TW201418215A (zh) 2014-05-16
EP2900634A1 (en) 2015-08-05
US9447036B2 (en) 2016-09-20
US20150246880A1 (en) 2015-09-03
JP2015535835A (ja) 2015-12-17
TWI601713B (zh) 2017-10-11
JP6251749B2 (ja) 2017-12-20
MX350575B (es) 2017-09-11
IL237749A (en) 2017-09-28
KR20150059778A (ko) 2015-06-02
EP2900634B1 (en) 2017-02-22
MX2015003902A (es) 2015-07-17
WO2014048958A1 (en) 2014-04-03
BR112015006825A2 (pt) 2017-08-08
IN2015DN02542A (da) 2015-09-11
CN104619683A (zh) 2015-05-13
ES2625547T3 (es) 2017-07-19
CN104619683B (zh) 2017-05-10

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