CA2592407A1 - Methods of treating pain - Google Patents
Methods of treating pain Download PDFInfo
- Publication number
- CA2592407A1 CA2592407A1 CA002592407A CA2592407A CA2592407A1 CA 2592407 A1 CA2592407 A1 CA 2592407A1 CA 002592407 A CA002592407 A CA 002592407A CA 2592407 A CA2592407 A CA 2592407A CA 2592407 A1 CA2592407 A1 CA 2592407A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- nitric oxide
- oxide donor
- aryl
- integer
- 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.)
- Abandoned
Links
- 208000002193 Pain Diseases 0.000 title claims abstract description 65
- 230000036407 pain Effects 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 56
- 239000002840 nitric oxide donor Substances 0.000 claims abstract description 132
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 86
- 239000000014 opioid analgesic Substances 0.000 claims abstract description 78
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 238000013268 sustained release Methods 0.000 claims abstract description 36
- 239000012730 sustained-release form Substances 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- -1 benzyloxy, benzylthio Chemical group 0.000 claims description 75
- 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 68
- 150000001875 compounds Chemical class 0.000 claims description 57
- 230000036592 analgesia Effects 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 238000009472 formulation Methods 0.000 claims description 36
- 229960005181 morphine Drugs 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 20
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 16
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 16
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- 229960002085 oxycodone Drugs 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- CMFNMSMUKZHDEY-UHFFFAOYSA-N peroxynitrous acid Chemical compound OON=O CMFNMSMUKZHDEY-UHFFFAOYSA-N 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 12
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 12
- 150000003573 thiols Chemical class 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 150000001356 alkyl thiols Chemical class 0.000 claims description 10
- 150000001504 aryl thiols Chemical class 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
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- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
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- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
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- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 5
- JJGYGPZNTOPXGV-UHFFFAOYSA-N 6-acetylmorphine Chemical compound C12C=CC(OC(C)=O)C3OC4=C5C32CCN(C)C1CC5=CC=C4O JJGYGPZNTOPXGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 5
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- 206010065390 Inflammatory pain Diseases 0.000 claims description 5
- OZYUPQUCAUTOBP-QXAKKESOSA-N Levallorphan Chemical compound C([C@H]12)CCC[C@@]11CCN(CC=C)[C@@H]2CC2=CC=C(O)C=C21 OZYUPQUCAUTOBP-QXAKKESOSA-N 0.000 claims description 5
- JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 claims description 5
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 5
- GNJCUHZOSOYIEC-GAROZEBRSA-N Morphine-6-glucuronide Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC=4C5=C(C(=CC=4)O)O[C@@H]1[C@]52CCN3C)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O GNJCUHZOSOYIEC-GAROZEBRSA-N 0.000 claims description 5
- IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 claims description 5
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- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 5
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- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims description 5
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical compound C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 claims description 5
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- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims description 5
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
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- 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
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
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- A—HUMAN NECESSITIES
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2004907352 | 2004-12-24 | ||
| AU2004907352A AU2004907352A0 (en) | 2004-12-24 | Methods of treating pain | |
| PCT/AU2005/001976 WO2006066362A1 (en) | 2004-12-24 | 2005-12-23 | Methods of treating pain |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2592407A1 true CA2592407A1 (en) | 2006-06-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002592407A Abandoned CA2592407A1 (en) | 2004-12-24 | 2005-12-23 | Methods of treating pain |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20090143417A1 (https=) |
| EP (1) | EP1838714A4 (https=) |
| JP (1) | JP2008525321A (https=) |
| CA (1) | CA2592407A1 (https=) |
| WO (1) | WO2006066362A1 (https=) |
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| US8409846B2 (en) | 1997-09-23 | 2013-04-02 | The United States Of America As Represented By The Department Of Veteran Affairs | Compositions, methods and devices for maintaining an organ |
| US12010987B2 (en) | 2004-10-07 | 2024-06-18 | Transmedics, Inc. | Systems and methods for ex-vivo organ care and for using lactate as an indication of donor organ status |
| IL273422B (en) | 2004-10-07 | 2022-07-01 | Transmedics Inc | Methods and systems for extracorporeal organ treatment |
| US9301519B2 (en) * | 2004-10-07 | 2016-04-05 | Transmedics, Inc. | Systems and methods for ex-vivo organ care |
| US8304181B2 (en) | 2004-10-07 | 2012-11-06 | Transmedics, Inc. | Method for ex-vivo organ care and for using lactate as an indication of donor organ status |
| ES2731298T3 (es) | 2005-05-27 | 2019-11-14 | Univ North Carolina Chapel Hill | Partículas de liberación de óxido nítrico para agentes terapéuticos de óxido nítrico y aplicaciones biomédicas |
| US9078428B2 (en) | 2005-06-28 | 2015-07-14 | Transmedics, Inc. | Systems, methods, compositions and solutions for perfusing an organ |
| CA2980782C (en) * | 2006-04-19 | 2020-10-27 | Transmedics, Inc. | Systems and methods for ex vivo organ care |
| WO2008080194A1 (en) * | 2006-12-29 | 2008-07-10 | The University Of Queensland | Pain-relieving compositions and uses therefor |
| US8822509B2 (en) | 2006-12-29 | 2014-09-02 | The University Of Queensland | Pain-relieving compositions and uses therefor |
| US9457179B2 (en) | 2007-03-20 | 2016-10-04 | Transmedics, Inc. | Systems for monitoring and applying electrical currents in an organ perfusion system |
| US9814230B2 (en) * | 2008-01-31 | 2017-11-14 | Transmedics, Inc. | Systems and methods for ex vivo lung care |
| WO2009152483A2 (en) * | 2008-06-12 | 2009-12-17 | University Of Alabama Huntsville | Nitric oxide induced adaptive resistance as a therapy for central nervous system diseases and trauma |
| WO2011022652A1 (en) | 2009-08-21 | 2011-02-24 | Novan, Inc. | Topical gels |
| CA2771389C (en) | 2009-08-21 | 2019-04-09 | Novan, Inc. | Wound dressings, methods of using the same and methods of forming the same |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| WO2012118829A2 (en) | 2011-02-28 | 2012-09-07 | Novan, Inc. | Tertiary s-nitrosothiol-modified nitricoxide-releasing xerogels and methods of using the same |
| WO2012142487A1 (en) * | 2011-04-14 | 2012-10-18 | Transmedics, Inc. | Organ care solution for ex-vivo machine perfusion of donor lungs |
| CA3185937A1 (en) | 2014-06-02 | 2015-12-10 | Transmedics, Inc. | Ex vivo organ care system |
| AU2015361996B2 (en) | 2014-12-12 | 2019-09-26 | Transmedics, Inc. | Apparatus and method for organ perfusion |
| EP3265118B1 (en) * | 2015-03-06 | 2019-08-28 | Centre National De La Recherche Scientifique | Use of creatine kinase and derived peptides thereof to relief pain |
| DK3824731T3 (da) | 2015-09-09 | 2025-05-26 | Transmedics Inc | Aortakanyle til ex vivo-organplejesystem |
| EP4238417A3 (en) | 2016-05-30 | 2023-12-06 | Tevosol, Inc. | Apparatus and method for ex vivo lung ventilation with a varying exterior pressure |
Family Cites Families (6)
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| US5405919A (en) * | 1992-08-24 | 1995-04-11 | The United States Of America As Represented By The Secretary Of Health And Human Services | Polymer-bound nitric oxide/nucleophile adduct compositions, pharmaceutical compositions and methods of treating biological disorders |
| EP0984012A3 (en) | 1998-08-31 | 2001-01-10 | Pfizer Products Inc. | Nitric oxide releasing oxindole prodrugs with analgesic and anti-inflammatory properties |
| CA2400708A1 (en) | 2000-02-22 | 2001-08-30 | Cellegy Canada Inc. | Methods and compositions for improving sleep |
| EP1336602A1 (en) * | 2002-02-13 | 2003-08-20 | Giovanni Scaramuzzino | Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases |
| US20030219494A1 (en) | 2002-03-20 | 2003-11-27 | Smith Maree Therese | Compositions and methods of using them |
| JP2005537223A (ja) * | 2002-04-05 | 2005-12-08 | ニトロメッド，インク． | 酸化窒素供与体、組成物および使用法 |
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2005
- 2005-12-23 US US11/794,137 patent/US20090143417A1/en not_active Abandoned
- 2005-12-23 WO PCT/AU2005/001976 patent/WO2006066362A1/en not_active Ceased
- 2005-12-23 CA CA002592407A patent/CA2592407A1/en not_active Abandoned
- 2005-12-23 EP EP05821596A patent/EP1838714A4/en not_active Withdrawn
- 2005-12-23 JP JP2007547107A patent/JP2008525321A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006066362A1 (en) | 2006-06-29 |
| EP1838714A1 (en) | 2007-10-03 |
| EP1838714A4 (en) | 2009-09-02 |
| US20090143417A1 (en) | 2009-06-04 |
| JP2008525321A (ja) | 2008-07-17 |
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