KR850002469A - 피세나돌 전구체 및 그의 중간체의 제조방법 - Google Patents

피세나돌 전구체 및 그의 중간체의 제조방법 Download PDF

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Publication number
KR850002469A
KR850002469A KR1019840005800A KR840005800A KR850002469A KR 850002469 A KR850002469 A KR 850002469A KR 1019840005800 A KR1019840005800 A KR 1019840005800A KR 840005800 A KR840005800 A KR 840005800A KR 850002469 A KR850002469 A KR 850002469A
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South Korea
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methyl
dialkyl
formula
propyl
alkyl
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KR1019840005800A
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KR870000270B1 (ko
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잭슨 바네트 챨스
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아더 알. 웨일
일라이 릴리 앤드 캄파니
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    • 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
    • C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen 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
    • C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—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 no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

내용 없음

Description

피세나돌 전구체 및 그의 중간체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. 일반식(Ⅲ)의 1,4-디알킬-4-(3-치환된 페닐)-3-테트라하이드로피리딘메탄아민을 염기성 반응매질중, 팔라듐 촉매상에서 수소화시킴을 특징으로 하여 일반식(Ⅰ)의 1,4-디알킬-3-메틸-4-(3-치환된 페닐) 피페리딘을 제조하는 방법.
    상기식에서, R1및 R2는 독립적으로 C1-C4알킬이고, R3는 C1-C3알콕시이고, R4및 R5중의 하나는 메틸이고 다른 하나는 수소이다.
  2. 제1항에 있어서, R1이 메틸이고, R2가 n-프로필이고, R3가 메톡시이고, R6및 R7이 모두 메틸인 방법.
  3. 제1항에 있어서, 사용된 촉매가 탄소상의 팔라듐촉매인 방법.
  4. 일반식(Ⅱ)의 1,4-디알킬-4-(3-치환된 페닐)테트라하이드로피리딘을 비친핵성 음이온을 제공하는 산의 존재하,pH약 1.0내지 약 5.0에서 포름알데하이드 및 NHR6R7와 반응시킴을 특징으로 하여 일반식(Ⅲ)의 1,4-디알킬-4-(3-치환된 페닐)-3-테트라하이드로피리딘메탄아민을 제조하는 방법.
    상기식에서, R1및 R2는 독립적으로 C1-C4알킬이고, R3는 C1-C3알콕시이고, R6및 R7은 독립적으로 C1-C3알킬이거나, 그들이 부착된 질소원자와 함께 피페리딘, 피페라진, N-메틸피페라진, 모르폴린 또는 피롤리딘을 형성한다.
  5. 제4항에 있어서, R1이 메틸이고 R2가 n-프로필인 방법.
  6. 제4항에 있어서, 1,4,5,6-테트라하이드로-4-(3-메톡시페닐)-N,N, 1-트리메틸-4-프로필-3-피리딘메탄아민을 제조하는 방법.
  7. a) n이 1인 경우에는, 디아스테레오머성 혼합물을 약 50°C내지 100°C에서 염산 수용액중에 용해시키고 그 용액을 냉각시켜 침전된 3a-메틸 디하이드레이트 염을 여과시켜 수집하거나,
    b) n이 0인 경우에는, 디아스테레오머성 혼합물을 아세토니트릴:에틸 아세테이트(5:1)로 재결정시키고 보다 덜 용해되는 3a-메틸 유동체를 여과시켜 수집함을 특징으로 하여 일반식(Ⅴ)의 디아스테레오머성 혼합물로 부터 일반식(Ⅳ)의 (±)-3-(1,4α-디알킬-3α-메틸-4β-피페리디닐)페놀을 분리시키는 방법.
    상기식에서, R1및 R2는 독립적으로 C1-C4알킬이고, R4및 R5중의 하나는 메틸이고 다른 하나는 수소이고, n은 0또는 1이다.
  8. 제7항에 있어서, R1이 메틸이고 R2가 n-프로필인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840005800A 1983-09-21 1984-09-21 1,4-디알킬-3-메틸-4-(3-치환된 페닐) 피페리딘의 제조방법 KR870000270B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US534468 1983-09-21
US06/534,468 US4581456A (en) 1983-09-21 1983-09-21 Processes for preparing picenadol precursors and novel intermediates thereof
US534,468 1983-09-21

Publications (2)

Publication Number Publication Date
KR850002469A true KR850002469A (ko) 1985-05-13
KR870000270B1 KR870000270B1 (ko) 1987-02-23

Family

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Family Applications (1)

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KR1019840005800A KR870000270B1 (ko) 1983-09-21 1984-09-21 1,4-디알킬-3-메틸-4-(3-치환된 페닐) 피페리딘의 제조방법

Country Status (11)

Country Link
US (1) US4581456A (ko)
EP (2) EP0136863B1 (ko)
JP (1) JPS6094961A (ko)
KR (1) KR870000270B1 (ko)
CA (1) CA1223258A (ko)
DE (1) DE3471301D1 (ko)
DK (1) DK445884A (ko)
GB (1) GB2146641B (ko)
GR (1) GR80426B (ko)
HU (1) HUT35247A (ko)
IL (1) IL72998A (ko)

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US5250542A (en) * 1991-03-29 1993-10-05 Eli Lilly And Company Peripherally selective piperidine carboxylate opioid antagonists
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GB9912417D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912413D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912411D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912416D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912410D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
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US6469030B2 (en) 1999-11-29 2002-10-22 Adolor Corporation Methods for the treatment and prevention of ileus
US20050148630A1 (en) * 2003-12-02 2005-07-07 Carpenter Randall L. Methods of preventing and treating non-opioid induced gastrointestinal dysfunction
US8946262B2 (en) * 2003-12-04 2015-02-03 Adolor Corporation Methods of preventing and treating gastrointestinal dysfunction
US20050240177A1 (en) * 2004-04-26 2005-10-27 Packaging Service Corporation Of Kentucky Electrosurgical forceps
US7700626B2 (en) * 2004-06-04 2010-04-20 Adolor Corporation Compositions containing opioid antagonists
US20060211733A1 (en) * 2005-03-04 2006-09-21 Adolor Corporation Methods of preventing and treating opioid bowel dysfunction
US8524731B2 (en) * 2005-03-07 2013-09-03 The University Of Chicago Use of opioid antagonists to attenuate endothelial cell proliferation and migration
US9662325B2 (en) 2005-03-07 2017-05-30 The University Of Chicago Use of opioid antagonists to attenuate endothelial cell proliferation and migration
US9662390B2 (en) * 2005-03-07 2017-05-30 The University Of Chicago Use of opioid antagonists to attenuate endothelial cell proliferation and migration
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Also Published As

Publication number Publication date
GB2146641A (en) 1985-04-24
CA1223258A (en) 1987-06-23
GB8423601D0 (en) 1984-10-24
JPS6094961A (ja) 1985-05-28
GB2146641B (en) 1987-05-28
EP0247639A2 (en) 1987-12-02
HUT35247A (en) 1985-06-28
KR870000270B1 (ko) 1987-02-23
DK445884D0 (da) 1984-09-19
IL72998A (en) 1988-03-31
US4581456A (en) 1986-04-08
GR80426B (en) 1985-01-22
EP0247639A3 (en) 1988-07-06
EP0136863A2 (en) 1985-04-10
DE3471301D1 (en) 1988-06-23
DK445884A (da) 1985-03-22
EP0136863A3 (en) 1985-07-31
EP0136863B1 (en) 1988-05-18

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