CA1315689C - Derives quaternaires de la noroxymorphone soulageant la nausee et le vomissement - Google Patents

Derives quaternaires de la noroxymorphone soulageant la nausee et le vomissement

Info

Publication number: CA1315689C
Authority: CA; Canada
Prior art keywords: administration; noroxymorphone; narcotic analgesic; morphine; emesis
Prior art date: 1987-09-03
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 - Lifetime

Application number

CA000548964A

Other languages

English (en)

Inventor

Leon I. Goldberg

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.)

University of Chicago

Original Assignee

University of Chicago

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.)

1987-09-03

Filing date

1987-10-09

Publication date

1993-04-06

1987-09-03 Priority claimed from US07/092,470 external-priority patent/US4861781A/en

1987-10-09 Application filed by University of Chicago filed Critical University of Chicago

1993-04-06 Application granted granted Critical

1993-04-06 Publication of CA1315689C publication Critical patent/CA1315689C/fr

2010-04-06 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

206010047700 Vomiting Diseases 0.000 title claims abstract description 29
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 claims abstract description 13
206010028813 Nausea Diseases 0.000 title claims abstract description 10
230000008693 nausea Effects 0.000 title claims abstract description 10
JVLBPIPGETUEET-WIXLDOGYSA-O (3r,4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7-one Chemical compound C([N@+]1(C)[C@@H]2CC=3C4=C(C(=CC=3)O)O[C@@H]3[C@]4([C@@]2(O)CCC3=O)CC1)C1CC1 JVLBPIPGETUEET-WIXLDOGYSA-O 0.000 claims abstract description 21
229960002921 methylnaltrexone Drugs 0.000 claims abstract description 21
150000001875 compounds Chemical class 0.000 claims abstract description 13
239000004084 narcotic analgesic agent Substances 0.000 claims abstract description 12
229940035676 analgesics Drugs 0.000 claims abstract description 3
239000000730 antalgic agent Substances 0.000 claims abstract description 3
230000003533 narcotic effect Effects 0.000 claims abstract description 3
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 66
229960005181 morphine Drugs 0.000 claims description 33
241001465754 Metazoa Species 0.000 claims description 10
230000037396 body weight Effects 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 4
239000000203 mixture Substances 0.000 claims 4
239000008194 pharmaceutical composition Substances 0.000 claims 2
150000001805 chlorine compounds Chemical group 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 3
229940079593 drug Drugs 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
230000002452 interceptive effect Effects 0.000 abstract 1
241000282472 Canis lupus familiaris Species 0.000 description 22
230000008673 vomiting Effects 0.000 description 5
230000000694 effects Effects 0.000 description 4
230000000968 intestinal effect Effects 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229960001797 methadone Drugs 0.000 description 2
229940127240 opiate Drugs 0.000 description 2
229960000482 pethidine Drugs 0.000 description 2
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
208000005298 acute pain Diseases 0.000 description 1
210000003818 area postrema Anatomy 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000000095 emetic effect Effects 0.000 description 1
210000005095 gastrointestinal system Anatomy 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000000034 method Methods 0.000 description 1
DQCKKXVULJGBQN-XFWGSAIBSA-N naltrexone Chemical group N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CC1 DQCKKXVULJGBQN-XFWGSAIBSA-N 0.000 description 1
229960003086 naltrexone Drugs 0.000 description 1
239000004081 narcotic agent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine

Landscapes

Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000548964A 1987-09-03 1987-10-09 Derives quaternaires de la noroxymorphone soulageant la nausee et le vomissement Expired - Lifetime CA1315689C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US092,470		1987-09-03
US07/092,470 US4861781A (en)	1986-03-07	1987-09-03	Quaternary derivatives of noroxymorphone which relieve nausea and emesis

Publications (1)

Publication Number	Publication Date
CA1315689C true CA1315689C (fr)	1993-04-06

Family

ID=22233375

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000548964A Expired - Lifetime CA1315689C (fr)	1987-09-03	1987-10-09	Derives quaternaires de la noroxymorphone soulageant la nausee et le vomissement

Country Status (6)

Country	Link
JP (1)	JP2625457B2 (fr)
KR (1)	KR890004704A (fr)
CA (1)	CA1315689C (fr)
DK (1)	DK167340B1 (fr)
NZ (1)	NZ222911A (fr)
PH (1)	PH22582A (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7563899B2 (en)	2005-05-25	2009-07-21	Progenics Pharmaceuticals, Inc.	(S)-N-methylnaltrexone
US7674904B2 (en)	2005-05-25	2010-03-09	Progenics Pharmaceuticals, Inc.	Synthesis of R-N-methylnaltrexone
US8247425B2 (en)	2008-09-30	2012-08-21	Wyeth	Peripheral opioid receptor antagonists and uses thereof
US8338446B2 (en)	2007-03-29	2012-12-25	Wyeth Llc	Peripheral opioid receptor antagonists and uses thereof
US8471022B2 (en)	2008-02-06	2013-06-25	Progenics Pharmaceuticals, Inc.	Preparation and use of (R),(R)-2,2′-bis-methylnaltrexone
US8518962B2 (en)	2005-03-07	2013-08-27	The University Of Chicago	Use of opioid antagonists
US8524731B2 (en)	2005-03-07	2013-09-03	The University Of Chicago	Use of opioid antagonists to attenuate endothelial cell proliferation and migration
US8546418B2 (en)	2007-03-29	2013-10-01	Progenics Pharmaceuticals, Inc.	Peripheral opioid receptor antagonists and uses thereof
US8552025B2 (en)	2003-04-08	2013-10-08	Progenics Pharmaceuticals, Inc.	Stable methylnaltrexone preparation
US8685995B2 (en)	2008-03-21	2014-04-01	The University Of Chicago	Treatment with opioid antagonists and mTOR inhibitors
US9102680B2 (en)	2007-03-29	2015-08-11	Wyeth Llc	Crystal forms of (R)-N-methylnaltrexone bromide and uses thereof
US12303592B2 (en)	2006-08-04	2025-05-20	Wyeth, Llc	Formulations for parenteral delivery of compounds and uses thereof

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6274591B1 (en)	1997-11-03	2001-08-14	Joseph F. Foss	Use of methylnaltrexone and related compounds
US6451806B2 (en)	1999-09-29	2002-09-17	Adolor Corporation	Methods and compositions involving opioids and antagonists thereof
US6469030B2 (en)	1999-11-29	2002-10-22	Adolor Corporation	Methods for the treatment and prevention of ileus
US9662325B2 (en)	2005-03-07	2017-05-30	The University Of Chicago	Use of opioid antagonists to attenuate endothelial cell proliferation and migration
ES2714198T3 (es)	2005-03-07	2019-05-27	Univ Chicago	Uso de antagonistas opioideos para atenuar la proliferación y la migración de células endoteliales
EP1946759A4 (fr) *	2005-10-11	2009-12-23	Toray Industries	Agent thérapeutique contre la nausée et/ou le vomissement
EA020658B1 (ru) *	2007-08-09	2014-12-30	Ренссилэйер Политекник Инститьют	Четвертичные опиоидные карбоксамиды

1987
- 1987-10-09 CA CA000548964A patent/CA1315689C/fr not_active Expired - Lifetime
- 1987-12-07 PH PH36178A patent/PH22582A/en unknown
- 1987-12-14 NZ NZ222911A patent/NZ222911A/en unknown
- 1987-12-28 JP JP62330356A patent/JP2625457B2/ja not_active Expired - Lifetime
- 1987-12-29 KR KR1019870015208A patent/KR890004704A/ko not_active Ceased
- 1987-12-30 DK DK693387A patent/DK167340B1/da not_active IP Right Cessation

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8552025B2 (en)	2003-04-08	2013-10-08	Progenics Pharmaceuticals, Inc.	Stable methylnaltrexone preparation
US9669096B2 (en)	2003-04-08	2017-06-06	Progenics Pharmaceuticals, Inc.	Stable pharmaceutical formulations of methylnaltrexone
US10376584B2 (en)	2003-04-08	2019-08-13	Progenics Pharmaceuticals, Inc.	Stable pharmaceutical formulations of methylnaltrexone
US8524731B2 (en)	2005-03-07	2013-09-03	The University Of Chicago	Use of opioid antagonists to attenuate endothelial cell proliferation and migration
US8518962B2 (en)	2005-03-07	2013-08-27	The University Of Chicago	Use of opioid antagonists
US8343992B2 (en)	2005-05-25	2013-01-01	Progenics Pharmaceuticals, Inc.	Synthesis of R-N-methylnaltrexone
US7674904B2 (en)	2005-05-25	2010-03-09	Progenics Pharmaceuticals, Inc.	Synthesis of R-N-methylnaltrexone
US7563899B2 (en)	2005-05-25	2009-07-21	Progenics Pharmaceuticals, Inc.	(S)-N-methylnaltrexone
US8916581B2 (en)	2005-05-25	2014-12-23	Progenics Pharmaceuticals, Inc.	(S)-N-methylnaltrexone
US9597327B2 (en)	2005-05-25	2017-03-21	Progenics Pharmaceuticals, Inc.	Synthesis of (R)-N-methylnaltrexone
US8003794B2 (en)	2005-05-25	2011-08-23	Progenics Pharmaceuticals, Inc.	(S)-N-methylnaltrexone
US12303592B2 (en)	2006-08-04	2025-05-20	Wyeth, Llc	Formulations for parenteral delivery of compounds and uses thereof
US8853232B2 (en)	2007-03-29	2014-10-07	Wyeth Llc	Peripheral opioid receptor antagonists and uses thereof
US8772310B2 (en)	2007-03-29	2014-07-08	Wyeth Llc	Peripheral opioid receptor antagonists and uses thereof
US8546418B2 (en)	2007-03-29	2013-10-01	Progenics Pharmaceuticals, Inc.	Peripheral opioid receptor antagonists and uses thereof
US8338446B2 (en)	2007-03-29	2012-12-25	Wyeth Llc	Peripheral opioid receptor antagonists and uses thereof
US9102680B2 (en)	2007-03-29	2015-08-11	Wyeth Llc	Crystal forms of (R)-N-methylnaltrexone bromide and uses thereof
US9879024B2 (en)	2007-03-29	2018-01-30	Progenics Pharmaceuticals., Inc.	Crystal forms of (R)-N-methylnaltrexone bromide and uses thereof
US8916706B2 (en)	2008-02-06	2014-12-23	Progenics Pharmaceuticals, Inc.	Preparation and use of (R),(R)-2,2′-bis-methylnaltrexone
US8471022B2 (en)	2008-02-06	2013-06-25	Progenics Pharmaceuticals, Inc.	Preparation and use of (R),(R)-2,2′-bis-methylnaltrexone
US8685995B2 (en)	2008-03-21	2014-04-01	The University Of Chicago	Treatment with opioid antagonists and mTOR inhibitors
US10383869B2 (en)	2008-03-21	2019-08-20	The University Of Chicago	Treatment with opioid antagonists and mTOR inhibitors
US9526723B2 (en)	2008-03-21	2016-12-27	The University Of Chicago	Treatment with opioid antagonists and mTOR inhibitors
US8455644B2 (en)	2008-09-30	2013-06-04	Wyeth	Peripheral opioid receptor antagonists and uses thereof
US9492445B2 (en)	2008-09-30	2016-11-15	Wyeth, Llc	Peripheral opioid receptor antagonists and uses thereof
US9724343B2 (en)	2008-09-30	2017-08-08	Wyeth, Llc	Peripheral opioid receptor antagonists and uses thereof
US9180125B2 (en)	2008-09-30	2015-11-10	Wyeth, Llc	Peripheral opioid receptor antagonists and uses thereof
US8822490B2 (en)	2008-09-30	2014-09-02	Wyeth Llc	Peripheral opioid receptor antagonists and uses thereof
US8420663B2 (en)	2008-09-30	2013-04-16	Wyeth	Peripheral opioid receptor antagonists and uses thereof
US8247425B2 (en)	2008-09-30	2012-08-21	Wyeth	Peripheral opioid receptor antagonists and uses thereof

Also Published As

Publication number	Publication date
DK693387D0 (da)	1987-12-30
JP2625457B2 (ja)	1997-07-02
JPS6468376A (en)	1989-03-14
DK167340B1 (da)	1993-10-18
NZ222911A (en)	1990-11-27
PH22582A (en)	1988-10-17
KR890004704A (ko)	1989-05-09
DK693387A (da)	1989-03-04

Publication	Publication Date	Title
US4861781A (en)	1989-08-29	Quaternary derivatives of noroxymorphone which relieve nausea and emesis
US4719215A (en)	1988-01-12	Quaternary derivatives of noroxymorphone which relieve nausea and emesis
CA1315689C (fr)	1993-04-06	Derives quaternaires de la noroxymorphone soulageant la nausee et le vomissement
EP0306575B1 (fr)	1992-07-29	Dérivés quaternaires de noroxymorphone pour le traitement de nausée et d'émèse
DE69233169T2 (de)	2004-05-27	Cisplatin und Topotecan enthaltende Zusammensetzung als antitumor.
DE69634609T2 (de)	2006-02-02	Analgesische synergie durch gleichzeitige verabreichung von subanalgesischen dosen eines mu-opioid agonisten und eines kappa - 2- opioi agonisten
CA1200501A (fr)	1986-02-11	Nalbuphene - analgesique stupefiant et methode de production de l'analgesie
PT1096936E (pt)	2007-05-31	Tratamento da discinesia
US5935944A (en)	1999-08-10	Formulation for I.V. administration of the boron delivery drug, boronophenylalanine (BPA)
US5629336A (en)	1997-05-13	Use of glycine/NMDA receptor ligands for the treatment of drug dependence and withdrawal
CA2165446C (fr)	2005-07-05	Utilisation de ropivacaine dans la preparation d'un produit pharmaceutique avec effet analgesique a blocage moteur minimal
CA2154455A1 (fr)	1994-08-04	Composition analgesique
AU684711B2 (en)	1998-01-08	Use of 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine for the treatment of pain and oedema
Dubois et al.	1988	Prevention and treatment of the gastric symptoms of radiation sickness
US4829068A (en)	1989-05-09	Treatment of disorders of the gastro-intestinal tract
KR930702985A (ko)	1993-11-29	식도암의 치료
GB2189703A (en)	1987-11-04	Vinpocetine
US20150258073A1 (en)	2015-09-17	INDICATION OF ANTHRA[2,1,c][1,2,5]THIADIAZOLE-6,11-DIONE COMPOUND IN ALLEVIATING PAIN
DE69816790T2 (de)	2004-04-22	Verbesserung der opioid-toleranz durch hemmung der induzierbaren stickstoffoxid-synthase zur behandlung von schmerzen
US20090270401A1 (en)	2009-10-29	Use of a dihydroimidazopyrazoine derivative for treating or preventing pain
JPH1129476A (ja)	1999-02-02	麻薬依存抑制剤
CA2295429A1 (fr)	2001-07-06	Traitement ou prevention de la diarrhee
Acri et al.	1995	Characterization of the Discriminative Stimulus Effects of Benztropine, A Potential Cocaine Therapeutic Agent
Lippmann et al.	1980	Analgesic onset time of iv butorphanol in postsurgical patients
JPH02264719A (ja)	1990-10-29	抗けいれん剤

Legal Events

Date	Code	Title	Description
2010-04-06	MKEX	Expiry