CS211364B2 - Method of making the oxymorfone - Google Patents

Method of making the oxymorfone Download PDF

Info

Publication number: CS211364B2
Authority: CS; Czechoslovakia
Prior art keywords: mixture; boron compound; reaction; oxycodone; hours
Prior art date: 1978-10-19

Application number

CS797115A

Other languages

Czech (cs)

English (en)

Inventor

Michael L Wilson

Original Assignee

Mallinckrodt 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.)

1978-10-19

Filing date

1979-10-19

Publication date

1982-02-26

1979-10-19 Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc

1982-02-26 Publication of CS211364B2 publication Critical patent/CS211364B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 4
229960002085 oxycodone Drugs 0.000 claims abstract description 30
BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims abstract description 29
UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims abstract description 23
229960005118 oxymorphone Drugs 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims abstract description 20
239000003795 chemical substances by application Substances 0.000 claims abstract description 13
239000002879 Lewis base Substances 0.000 claims abstract description 4
150000007527 lewis bases Chemical class 0.000 claims abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 27
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 22
239000011541 reaction mixture Substances 0.000 claims description 21
150000001639 boron compounds Chemical class 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 19
239000012649 demethylating agent Substances 0.000 claims description 16
238000010520 demethylation reaction Methods 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
230000017858 demethylation Effects 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
239000012429 reaction media Substances 0.000 claims description 10
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
-1 alcohol halides Chemical class 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
230000001335 demethylating effect Effects 0.000 claims description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
239000000908 ammonium hydroxide Substances 0.000 claims description 4
239000008367 deionised water Substances 0.000 claims description 4
229910021641 deionized water Inorganic materials 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
239000000047 product Substances 0.000 claims description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
239000000706 filtrate Substances 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 2
239000007787 solid Substances 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
230000003313 weakening effect Effects 0.000 claims 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 2
229910052796 boron Inorganic materials 0.000 abstract description 2
239000003153 chemical reaction reagent Substances 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 15
239000010410 layer Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
230000007062 hydrolysis Effects 0.000 description 9
238000006460 hydrolysis reaction Methods 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
239000006227 byproduct Substances 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001638 boron Chemical class 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000002037 dichloromethane fraction Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000004064 recycling Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 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:
- C07D489/06—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 a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polarising Elements (AREA)

CS797115A 1978-10-19 1979-10-19 Method of making the oxymorfone CS211364B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US95305678A	1978-10-19	1978-10-19

Publications (1)

Publication Number	Publication Date
CS211364B2 true CS211364B2 (en)	1982-02-26

Family

ID=25493512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS797115A CS211364B2 (en)	1978-10-19	1979-10-19	Method of making the oxymorfone

Country Status (16)

Country	Link
JP (1)	JPS55501025A (da)
AU (1)	AU5189779A (da)
BE (1)	BE879494A (da)
CA (1)	CA1108132A (da)
CS (1)	CS211364B2 (da)
DK (1)	DK258280A (da)
ES (1)	ES485154A1 (da)
FI (1)	FI793235A7 (da)
FR (1)	FR2439201A1 (da)
GB (1)	GB2049680A (da)
IL (1)	IL58489A0 (da)
IT (1)	IT7969032A0 (da)
NL (1)	NL7920126A (da)
NO (1)	NO793297L (da)
SE (1)	SE8004454L (da)
WO (1)	WO1980000841A1 (da)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4795813A (en) *	1981-08-17	1989-01-03	The Florida Board Of Regents On Behalf Of The Florida State University	Synthesis of derivatives of codeine and other 3-O-alkylmorphines
US5668285A (en) *	1986-10-31	1997-09-16	The United States Of America As Represented By The Department Of Health And Human Services	Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates
FR2636330B1 (fr) *	1988-09-13	1990-11-30	Sanofi Sa	Procede de preparation de derives de morphinane
CA2067200C (en) *	1989-10-16	1998-06-30	Kenner C. Rice	Total synthesis of northebaine, normorphine, noroxymorphone enantiomers and derivatives via n-nor intermediates
DE60223254T2 (de)	2001-07-06	2008-08-14	Penwest Pharmaceuticals Co.	Verzögert freisetzende formulierungen von oxymorphon
JP2005515966A (ja)	2001-07-06	2005-06-02	エンドーファーマシューティカルズ，インコーポレイティド	鎮痛薬としての使用のための６−ヒドロキシ−オキシモルホンの経口投与
US8329216B2 (en)	2001-07-06	2012-12-11	Endo Pharmaceuticals Inc.	Oxymorphone controlled release formulations
US7776314B2 (en)	2002-06-17	2010-08-17	Grunenthal Gmbh	Abuse-proofed dosage system
DE102005005446A1 (de)	2005-02-04	2006-08-10	Grünenthal GmbH	Bruchfeste Darreichungsformen mit retardierter Freisetzung
US20070048228A1 (en)	2003-08-06	2007-03-01	Elisabeth Arkenau-Maric	Abuse-proofed dosage form
DE10336400A1 (de)	2003-08-06	2005-03-24	Grünenthal GmbH	Gegen Missbrauch gesicherte Darreichungsform
DE10361596A1 (de)	2003-12-24	2005-09-29	Grünenthal GmbH	Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform
DE102004032049A1 (de)	2004-07-01	2006-01-19	Grünenthal GmbH	Gegen Missbrauch gesicherte, orale Darreichungsform
DE102005005449A1 (de)	2005-02-04	2006-08-10	Grünenthal GmbH	Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform
CN101395159A (zh)	2006-03-02	2009-03-25	马林克罗特公司	制备含有低含量α,β-不饱和酮化合物的吗啡烷-6-酮产物的方法
CA2713128C (en)	2008-01-25	2016-04-05	Gruenenthal Gmbh	Pharmaceutical dosage form
AU2009243681B2 (en)	2008-05-09	2013-12-19	Grunenthal Gmbh	Process for the preparation of an intermediate powder formulation and a final solid dosage form under usage of a spray congealing step
CN102639118B (zh)	2009-07-22	2015-07-29	格吕伦塔尔有限公司	氧化稳定的抗干扰剂型
KR101738369B1 (ko)	2009-07-22	2017-05-22	그뤼넨탈 게엠베하	핫 멜트 압출된 제어 방출 투여형
TWI516286B (zh)	2010-09-02	2016-01-11	歌林達股份有限公司	含陰離子聚合物之抗破碎劑型
BR112013005194A2 (pt)	2010-09-02	2016-05-03	Gruenenthal Gmbh	forma de dosagem resistente à violação compreendendo sal inorgânico
BR112014001091A2 (pt)	2011-07-29	2017-02-14	Gruenenthal Gmbh	comprimido resistente à adulteração que fornece liberação imediata do fármaco
EA201400172A1 (ru)	2011-07-29	2014-06-30	Грюненталь Гмбх	Устойчивая к разрушению таблетка, которая обеспечивает немедленное высвобождение лекарственного средства
MX356421B (es)	2012-02-28	2018-05-29	Gruenenthal Gmbh	Forma de dosificacion resistente a la manipulacion indebida que comprende un compuesto farmacologicamente activo y un polimero anionico.
EP2838512B1 (en)	2012-04-18	2018-08-22	Grünenthal GmbH	Tamper resistant and dose-dumping resistant pharmaceutical dosage form
US10064945B2 (en)	2012-05-11	2018-09-04	Gruenenthal Gmbh	Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc
US9737490B2 (en)	2013-05-29	2017-08-22	Grünenthal GmbH	Tamper resistant dosage form with bimodal release profile
EP3003279A1 (en)	2013-05-29	2016-04-13	Grünenthal GmbH	Tamper-resistant dosage form containing one or more particles
BR112016000194A8 (pt)	2013-07-12	2019-12-31	Gruenenthal Gmbh	forma de dosagem resistente à violação contendo o polímero de acetato de etileno-vinila
EP3073994A1 (en)	2013-11-26	2016-10-05	Grünenthal GmbH	Preparation of a powdery pharmaceutical composition by means of cryo-milling
WO2015173195A1 (en)	2014-05-12	2015-11-19	Grünenthal GmbH	Tamper resistant immediate release capsule formulation comprising tapentadol
EA201692388A1 (ru)	2014-05-26	2017-05-31	Грюненталь Гмбх	Лекарственная форма в виде множества частиц, защищенная от вызываемого этанолом сброса дозы
WO2016170097A1 (en)	2015-04-24	2016-10-27	Grünenthal GmbH	Tamper-resistant dosage form with immediate release and resistance against solvent extraction
JP2018526414A (ja)	2015-09-10	2018-09-13	グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング	乱用抑止性の即放性製剤を用いた経口過剰摂取に対する保護
EP3252055B1 (en)	2016-05-31	2018-09-19	Alcaliber Investigacion Desarrollo e Innovacion SLU	Process for obtaining 3,14-diacetyloxymorphone from oripavine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3249616A (en) *		1966-05-03		Ix-dfflydroxy-g-oxo-n-phenethylmor- phinan (cis) and production thereof
US2806033A (en) *	1955-08-03	1957-09-10	Lewenstein	Morphine derivative
US3775414A (en) *	1972-05-10	1973-11-27	Bristol Myers Co	Process for the preparation of 14-hydroxymorphinan derivatives

1979
- 1979-10-12 NO NO793297A patent/NO793297L/no unknown
- 1979-10-18 FI FI793235A patent/FI793235A7/fi not_active Application Discontinuation
- 1979-10-18 IT IT7969032A patent/IT7969032A0/it unknown
- 1979-10-18 GB GB8014422A patent/GB2049680A/en not_active Withdrawn
- 1979-10-18 WO PCT/US1979/000862 patent/WO1980000841A1/en not_active Ceased
- 1979-10-18 AU AU51897/79A patent/AU5189779A/en not_active Abandoned
- 1979-10-18 IL IL58489A patent/IL58489A0/xx unknown
- 1979-10-18 FR FR7925895A patent/FR2439201A1/fr not_active Withdrawn
- 1979-10-18 NL NL7920126A patent/NL7920126A/nl unknown
- 1979-10-18 BE BE0/197710A patent/BE879494A/fr unknown
- 1979-10-18 ES ES485154A patent/ES485154A1/es not_active Expired
- 1979-10-18 JP JP50190279A patent/JPS55501025A/ja active Pending
- 1979-10-18 CA CA337,908A patent/CA1108132A/en not_active Expired
- 1979-10-19 CS CS797115A patent/CS211364B2/cs unknown
1980
- 1980-06-16 SE SE8004454A patent/SE8004454L/xx not_active Application Discontinuation
- 1980-06-17 DK DK258280A patent/DK258280A/da unknown

Also Published As

Publication number	Publication date
ES485154A1 (es)	1980-06-16
GB2049680A (en)	1980-12-31
NL7920126A (nl)	1980-08-29
NO793297L (no)	1980-04-22
BE879494A (fr)	1980-02-15
IL58489A0 (en)	1980-01-31
JPS55501025A (da)	1980-11-27
FI793235A7 (fi)	1981-01-01
WO1980000841A1 (en)	1980-05-01
CA1108132A (en)	1981-09-01
AU5189779A (en)	1980-04-24
IT7969032A0 (it)	1979-10-18
FR2439201A1 (fr)	1980-05-16
SE8004454L (sv)	1980-06-16
DK258280A (da)	1980-06-17

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