CA2368479C - Method of producing 3,4-dehydroprolines and 3,4-dehydropiperidines - Google Patents

Method of producing 3,4-dehydroprolines and 3,4-dehydropiperidines Download PDF

Info

Publication number
CA2368479C
CA2368479C CA002368479A CA2368479A CA2368479C CA 2368479 C CA2368479 C CA 2368479C CA 002368479 A CA002368479 A CA 002368479A CA 2368479 A CA2368479 A CA 2368479A CA 2368479 C CA2368479 C CA 2368479C
Authority
CA
Canada
Prior art keywords
alkyl
hydrogen
formula
compound
iii
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.)
Expired - Fee Related
Application number
CA002368479A
Other languages
English (en)
French (fr)
Other versions
CA2368479A1 (en
Inventor
Bernd Schafer
Gunter Helmchen
Uli Kazmaier
Simone Schleich
Helmut Stahr
Volker Wolfart
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Abbott GmbH and Co KG
Original Assignee
Abbott GmbH and Co KG
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 Abbott GmbH and Co KG filed Critical Abbott GmbH and Co KG
Publication of CA2368479A1 publication Critical patent/CA2368479A1/en
Application granted granted Critical
Publication of CA2368479C publication Critical patent/CA2368479C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA002368479A 1999-03-26 2000-03-17 Method of producing 3,4-dehydroprolines and 3,4-dehydropiperidines Expired - Fee Related CA2368479C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19913699A DE19913699A1 (de) 1999-03-26 1999-03-26 Verfahren zur Herstellung von 3,4-Dihydroprolinen und 3,4-Dehydropiperidinen
DE19913699.8 1999-03-26
PCT/EP2000/002377 WO2000058284A1 (de) 1999-03-26 2000-03-17 Verfahren zur herstellung von n-acyl-3,4 - dehydroprolin und n-acyl-3,4 - dehydropiperidin-2-carbonsäure derivaten

Publications (2)

Publication Number Publication Date
CA2368479A1 CA2368479A1 (en) 2000-10-05
CA2368479C true CA2368479C (en) 2005-03-01

Family

ID=7902464

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002368479A Expired - Fee Related CA2368479C (en) 1999-03-26 2000-03-17 Method of producing 3,4-dehydroprolines and 3,4-dehydropiperidines

Country Status (22)

Country Link
US (1) US6579971B1 (enExample)
EP (1) EP1165509B1 (enExample)
JP (1) JP3868210B2 (enExample)
KR (1) KR20010104730A (enExample)
CN (1) CN1345310A (enExample)
AT (1) ATE278665T1 (enExample)
AU (1) AU3962500A (enExample)
BR (1) BR0009330A (enExample)
CA (1) CA2368479C (enExample)
CZ (1) CZ20013456A3 (enExample)
DE (2) DE19913699A1 (enExample)
ES (1) ES2230088T3 (enExample)
HK (1) HK1045156A1 (enExample)
HU (1) HUP0200420A2 (enExample)
IL (1) IL145525A0 (enExample)
MX (1) MXPA01009679A (enExample)
NO (1) NO20014645L (enExample)
RU (1) RU2001129097A (enExample)
TR (1) TR200102747T2 (enExample)
TW (1) TWI276626B (enExample)
WO (1) WO2000058284A1 (enExample)
ZA (1) ZA200107629B (enExample)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100396666C (zh) * 2005-12-14 2008-06-25 郑州大学 （4s）-1-叔丁氧羰基-4-氨基-l-脯氨酸乙酯及其合成工艺

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4291040A (en) * 1979-10-22 1981-09-22 E. R. Squibb & Sons, Inc. Mercaptoacyl derivatives of 4-disubstituted prolines and 4-substituted dehydroprolines
US5580575A (en) 1989-12-22 1996-12-03 Imarx Pharmaceutical Corp. Therapeutic drug delivery systems
JPH09502191A (ja) 1993-09-09 1997-03-04 シエーリング アクチエンゲゼルシヤフト 作用物質およびガスを含有する微粒子
DE19630082A1 (de) * 1996-07-26 1998-01-29 Basf Ag Verfahren zur Herstellung von 3-Pyrrolin-2-carbonsäure-Derivaten
US6090800A (en) 1997-05-06 2000-07-18 Imarx Pharmaceutical Corp. Lipid soluble steroid prodrugs
DE19723473A1 (de) * 1997-06-04 1998-12-10 Basf Ag Verfahren zur Herstellung von chiralen 3,4-Didehydroprolinen
CA2319433C (en) 1998-02-09 2008-04-22 Bracco Research S.A. Targeted delivery of biologically active media

Also Published As

Publication number Publication date
RU2001129097A (ru) 2004-03-20
CZ20013456A3 (cs) 2002-05-15
AU3962500A (en) 2000-10-16
NO20014645D0 (no) 2001-09-25
MXPA01009679A (es) 2002-03-14
EP1165509B1 (de) 2004-10-06
KR20010104730A (ko) 2001-11-26
WO2000058284A1 (de) 2000-10-05
TWI276626B (en) 2007-03-21
CN1345310A (zh) 2002-04-17
NO20014645L (no) 2001-09-25
HUP0200420A2 (hu) 2002-05-29
CA2368479A1 (en) 2000-10-05
ATE278665T1 (de) 2004-10-15
TR200102747T2 (tr) 2002-02-21
ES2230088T3 (es) 2005-05-01
BR0009330A (pt) 2002-01-08
IL145525A0 (en) 2002-06-30
ZA200107629B (en) 2002-09-17
DE50008117D1 (de) 2004-11-11
EP1165509A1 (de) 2002-01-02
JP2002540190A (ja) 2002-11-26
US6579971B1 (en) 2003-06-17
HK1045156A1 (zh) 2002-11-15
JP3868210B2 (ja) 2007-01-17
DE19913699A1 (de) 2000-09-28

Similar Documents

Publication Publication Date Title
CA1124725A (en) Alkanoyl-thio-acyl derivatives of dehydrocyclicimino acids
CA1244041A (en) Process for the preparation of cis, endo- octahydrocyclopenta¬b|pyrrole-2-carboxylate
DE69616446T2 (de) Verfahren zur herstellung von alpha-haloketonen, alpha-halohydrinen und epoxiden
JPWO1996023756A1 (ja) α−ハロケトン、α−ハロヒドリン及びエポキシドの製造法
RU2730006C1 (ru) Способ получения 5r-[(бензилокси)амино]пиперидин-2s-карбоновой кислоты или её производного
Pyne et al. Exo-Diastereoselective 1, 3-dipolar cycloadditions of azomethine ylides to (2R)-3-Benzoyl-4-methylene-2-phenyloxazolidin-5-one
Yuste et al. Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides
CA2368479C (en) Method of producing 3,4-dehydroprolines and 3,4-dehydropiperidines
CA2589042A1 (en) Novel process for the manufacture of 3-pyrrolidin-2-yl-propionic acid derivatives
CA2261628C (en) Process for preparing 3-pyrroline-2-carboxylic acid derivatives
Bongini et al. Asymmetric 1, 4 addition of grignard reagents to chiral α, β-unsaturated imides in the presence of lewis acids
Kulesza et al. Diastereoselective allylation of chiral imines and a stereocontrolled route to 4-hydroxy-N-tosylpipecolic acid derivatives
Poupardin et al. Rapid asymmetric synthesis of highly functionalized C5 chiral synthons. Practical preparation of trans-3-hydroxy-D-proline
JPH11349567A (ja) ３―アミノ―２―オキソ―ピロリジンの製造方法、新規中間体およびその使用
US5514814A (en) Pyrrolinone-based compounds
Bland Synthesis of (R)-(+)-boc-iturinic acid (n-C14) from aspartic acid
DE19505933C2 (de) Verfahren zur Herstellung von L-Aspartyl-D-alanin-N-(thietan-3-yl)-amiden
NO147273B (no) Analogifremgangsmaate til fremstilling av terapeutisk aktive cykloheksadien-derivater
US6166222A (en) Method for producing chiral 3,4-dehydroprolines
KR20020006703A (ko) 광학활성 아미노산 유도체의 제조법
Sivaprakasam et al. A straightforward synthesis of 3-substituted azetidinic amino acids
Sewald et al. Asymmetric synthesis of β‐amino acids and α‐deuterated β‐amino acids via conjugate addition of homochiral amidocuprates
AU748779B2 (en) The preparation of 3-pyroline-2-carboxylic acid amine derivatives
JPH08259519A (ja) α−アミノグリコールの製造法及びその中間体
MXPA99010984A (en) Method for producing chiral 3,4-dehydroprolines

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed