ATE178329T1 - Totale synthese von northebain-, normorphin-, noroxymorphon-enantiomeren und -derivaten via n- nor-zwischenverbindungen - Google Patents

Totale synthese von northebain-, normorphin-, noroxymorphon-enantiomeren und -derivaten via n- nor-zwischenverbindungen

Info

Publication number: ATE178329T1
Authority: AT; Austria
Prior art keywords: ether; northebain; noroxymorphone; normorphine; enantiomers
Prior art date: 1989-10-16

Application number

AT90917159T

Other languages

English (en)

Inventor

Kenner Cralle Rice

Amy Hauck Newman

Original Assignee

Us Health

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.)

1989-10-16

Filing date

1990-10-16

Publication date

1999-04-15

1990-10-16 Application filed by Us Health filed Critical Us Health

1999-04-15 Application granted granted Critical

1999-04-15 Publication of ATE178329T1 publication Critical patent/ATE178329T1/de

Links

ONBWJWYUHXVEJS-ZTYRTETDSA-N Normorphine Chemical compound C([C@@H](NCC1)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ONBWJWYUHXVEJS-ZTYRTETDSA-N 0.000 title 1
HLMSIZPQBSYUNL-IPOQPSJVSA-N Noroxymorphone Chemical class O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4 HLMSIZPQBSYUNL-IPOQPSJVSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 title 1
229950006134 normorphine Drugs 0.000 title 1
QKQQEIVDLRUZRP-UHFFFAOYSA-N northebaine Natural products COC1=CC=C2C(NCC3)CC4=CC=C(OC)C5=C4C23C1O5 QKQQEIVDLRUZRP-UHFFFAOYSA-N 0.000 title 1
238000006257 total synthesis reaction Methods 0.000 title 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
239000000543 intermediate Substances 0.000 abstract 2
238000000034 method Methods 0.000 abstract 2
239000007858 starting material Substances 0.000 abstract 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
239000000556 agonist Substances 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
238000009795 derivation Methods 0.000 abstract 1
229940098779 methanesulfonic acid Drugs 0.000 abstract 1
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 abstract 1
239000004081 narcotic agent Substances 0.000 abstract 1
229940127240 opiate Drugs 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
- C07D489/04—Salts; Organic complexes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

AT90917159T 1989-10-16 1990-10-16 Totale synthese von northebain-, normorphin-, noroxymorphon-enantiomeren und -derivaten via n- nor-zwischenverbindungen ATE178329T1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US42190089A	1989-10-16	1989-10-16

Publications (1)

Publication Number	Publication Date
ATE178329T1 true ATE178329T1 (de)	1999-04-15

Family

ID=23672545

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT90917159T ATE178329T1 (de)	1989-10-16	1990-10-16	Totale synthese von northebain-, normorphin-, noroxymorphon-enantiomeren und -derivaten via n- nor-zwischenverbindungen

Country Status (10)

Country	Link
EP (1)	EP0496830B1 (de)
JP (1)	JP2694156B2 (de)
AT (1)	ATE178329T1 (de)
AU (1)	AU642447B2 (de)
CA (1)	CA2067200C (de)
DE (1)	DE69033035T2 (de)
DK (1)	DK0496830T3 (de)
ES (1)	ES2129395T3 (de)
GR (1)	GR3030101T3 (de)
WO (1)	WO1991005768A1 (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2006084389A1 (de) *	2005-02-11	2006-08-17	Cilag Ltd.	Verfahren zur reinigung von noroxymorphon-verbindungen
ATE493417T1 (de) *	2005-06-16	2011-01-15	Mallinckrodt Inc	Synthetische route zu 14-hydroxylopiaten über 1- halogenthebain oder analoga
WO2008131567A1 (de) *	2007-04-27	2008-11-06	Cilag Ag	Lösungsmittelfreie kristalline form von naltrexon
WO2009067275A1 (en) *	2007-11-21	2009-05-28	Progenics Pharmaceuticals, Inc	N-oxides of 4,5-epoxy-morphinanium analogs
NZ611651A (en) *	2007-12-17	2014-11-28	Mallinckrodt Llc	Sinomenine derivatives and processes for their synthesis
EP2222642B1 (de) *	2007-12-17	2014-02-12	Mallinckrodt LLC	Verfahren und verbindungen zur herstellung von (+) opiaten
RS55777B1 (sr) *	2010-11-05	2017-07-31	H Lundbeck As	Postupak za proizvodnju naltreksona
US8580963B2 (en)	2010-11-05	2013-11-12	H. Lundbeck A/S	Method for the manufacturing of naltrexone
JO3209B1 (ar) *	2010-11-05	2018-03-08	H Lundbeck As	طريقة لتصنيع نالتريكسون
CN103619847A (zh) *	2011-05-06	2014-03-05	布鲁克大学	通过金属催化n-脱甲基化/官能化以及分子内基团转移制备吗啡类似物的方法
US20140155608A1 (en)	2012-05-03	2014-06-05	H. Lundbeck A/S	Method for the manufacturing of naltrexone
ES2631197T3 (es)	2012-12-14	2017-08-29	Purdue Pharma Lp	Análogos de piridonamorfinano y actividad biológica sobre los receptores opiodes
US9340542B2 (en)	2013-12-26	2016-05-17	Purdue Pharma L.P.	Propellane-based compounds and the use thereof
MA40170A (fr) *	2014-06-13	2017-04-19	Purdue Pharma Lp	Dérivés hétérocycliques de morphinan et leur utilisation
EP4225312A1 (de)	2020-10-06	2023-08-16	Scilex Holding Company	Orale verzögerte burst-formulierung von niedrigdosiertem naltrexon oder naloxon zur behandlung von fibromyalgie und langer covid
CN120703275B (zh) *	2025-08-27	2025-11-25	上海万巷制药有限公司	一种罂粟油中可待因、吗啡、罂粟碱、那可丁和蒂巴因含量的测定方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA913077A (en) *		1972-10-24	J. Pachter Irwin	Process of preparing n-substituted 14-hydroxydihydronormorphines
BE638369A (de) *	1962-10-10
FR2208902A1 (en) *	1972-06-15	1974-06-28	Merck & Co Inc	14-Hydroxy dihydronormorphinone prepn. - from 1-halo-nor codeinone, by oxidn., catalytic redn. and hydrolysis
US4141897A (en) *	1976-12-20	1979-02-27	Research Corporation	N-dealkylation of N-alkyl-14-hydroxymorphinans and derivatives thereof
NO793297L (no) *	1978-10-19	1980-04-22	Mallinckrodt Inc	Fremgangsmaate til fremstilling av oksymorfon
NO802139L (no) *	1979-08-09	1981-02-10	Mallinckrodt Inc	Utgangsforbindelser for fremstilling av morfinderivater, samt fremgangsmaate til fremstilling av utgangsforbindelsene
US4368326A (en) *	1980-07-03	1983-01-11	Rice Kenner C	Short total synthesis of dihydrothebainone, dihydrocodeinone, and nordihydroccodeinone
US4521601A (en) *	1981-05-20	1985-06-04	The United States Of America As Represented By The Department Of Health & Human Services	Practical total synthesis unnatural enantiomers of opium-derived morphinans
US4472253A (en)	1981-08-17	1984-09-18	The Florida Board Of Regents On Behalf Of The Florida State University	Process for the preparation of an N-substituted 3-O-alkyl-14-hydroxynormorphinone derivative
US4613668A (en) *	1983-12-22	1986-09-23	The United States Of America As Represented By The Department Of Health And Human Services	Short total synthesis or morphinan compounds which uses cyclization of a cycloalkylcarbonyl compound selected from cyclopropylcarbonyl and cyclobutylcarbonyl
US4639520A (en) *	1984-03-27	1987-01-27	Mallinckrodt, Inc.	Preparation of 14-hydroxy-N-ethoxy-carbonyl-norcodeinone
JPS62123444A (ja) *	1985-08-07	1987-06-04	Japan Synthetic Rubber Co Ltd	ポジ型感放射線性樹脂組成物
JPH0721626B2 (ja) *	1985-08-10	1995-03-08	日本合成ゴム株式会社	半導体微細加工用レジスト組成物

1990
- 1990-10-16 CA CA002067200A patent/CA2067200C/en not_active Expired - Lifetime
- 1990-10-16 WO PCT/US1990/005911 patent/WO1991005768A1/en not_active Ceased
- 1990-10-16 EP EP90917159A patent/EP0496830B1/de not_active Expired - Lifetime
- 1990-10-16 AT AT90917159T patent/ATE178329T1/de not_active IP Right Cessation
- 1990-10-16 JP JP3500396A patent/JP2694156B2/ja not_active Expired - Fee Related
- 1990-10-16 DE DE69033035T patent/DE69033035T2/de not_active Expired - Fee Related
- 1990-10-16 ES ES90917159T patent/ES2129395T3/es not_active Expired - Lifetime
- 1990-10-16 DK DK90917159T patent/DK0496830T3/da active
- 1990-10-16 AU AU67426/90A patent/AU642447B2/en not_active Ceased
1999
- 1999-04-30 GR GR990401183T patent/GR3030101T3/el unknown

Also Published As

Publication number	Publication date
DE69033035T2 (de)	1999-08-05
WO1991005768A1 (en)	1991-05-02
EP0496830B1 (de)	1999-03-31
CA2067200C (en)	1998-06-30
GR3030101T3 (en)	1999-07-30
EP0496830A4 (en)	1992-09-30
JP2694156B2 (ja)	1997-12-24
DK0496830T3 (da)	1999-10-11
AU642447B2 (en)	1993-10-21
ES2129395T3 (es)	1999-06-16
DE69033035D1 (de)	1999-05-06
EP0496830A1 (de)	1992-08-05
CA2067200A1 (en)	1991-04-17
JPH04504861A (ja)	1992-08-27
AU6742690A (en)	1991-05-16

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Legal Events

Date	Code	Title	Description
1999-12-15	UEP	Publication of translation of european patent specification
2010-07-15	REN	Ceased due to non-payment of the annual fee