AU2009274147B2 - Large substituent, non-phenolic amine opioids - Google Patents
Large substituent, non-phenolic amine opioids Download PDFInfo
- Publication number
- AU2009274147B2 AU2009274147B2 AU2009274147A AU2009274147A AU2009274147B2 AU 2009274147 B2 AU2009274147 B2 AU 2009274147B2 AU 2009274147 A AU2009274147 A AU 2009274147A AU 2009274147 A AU2009274147 A AU 2009274147A AU 2009274147 B2 AU2009274147 B2 AU 2009274147B2
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- AU
- Australia
- Prior art keywords
- hydrogen
- compound according
- alkyl
- optionally substituted
- lower alkyl
- 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.)
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- -1 phenolic amine Chemical class 0.000 title claims abstract description 69
- 229940005483 opioid analgesics Drugs 0.000 title description 4
- 125000001424 substituent group Chemical group 0.000 title description 3
- 239000003814 drug Substances 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 106
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 108090000137 Opioid Receptors Proteins 0.000 claims description 24
- 102000003840 Opioid Receptors Human genes 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 206010013663 drug dependence Diseases 0.000 claims description 17
- 230000027455 binding Effects 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
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- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
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- 150000003839 salts Chemical class 0.000 claims description 9
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
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- 125000002252 acyl group Chemical group 0.000 claims description 7
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- 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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- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
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- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
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- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 4
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- 125000004122 cyclic group Chemical group 0.000 claims description 4
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- 238000011282 treatment Methods 0.000 claims description 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
- 206010010904 Convulsion Diseases 0.000 claims description 3
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- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
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- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 229960002715 nicotine Drugs 0.000 claims description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000000954 anitussive effect Effects 0.000 abstract description 5
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- 229940124584 antitussives Drugs 0.000 abstract 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 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 230000031143 xenobiotic glucuronidation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8225508P | 2008-07-21 | 2008-07-21 | |
| US61/082,255 | 2008-07-21 | ||
| PCT/US2009/051200 WO2010011619A1 (en) | 2008-07-21 | 2009-07-21 | Large substituent, non-phenolic amine opioids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2009274147A1 AU2009274147A1 (en) | 2010-01-28 |
| AU2009274147B2 true AU2009274147B2 (en) | 2014-09-04 |
Family
ID=41137538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009274147A Active AU2009274147B2 (en) | 2008-07-21 | 2009-07-21 | Large substituent, non-phenolic amine opioids |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100190817A1 (enExample) |
| EP (1) | EP2318372B9 (enExample) |
| JP (2) | JP5727374B2 (enExample) |
| AU (1) | AU2009274147B2 (enExample) |
| CA (1) | CA2731429C (enExample) |
| ES (1) | ES2534055T3 (enExample) |
| WO (1) | WO2010011619A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5727374B2 (ja) * | 2008-07-21 | 2015-06-03 | レンセラール ポリテクニック インスティチュート | 大型置換基を有する非フェノール性アミンオピオイド |
| HRP20191029T1 (hr) | 2009-12-04 | 2019-09-20 | Alkermes Pharma Ireland Limited | Derivati morfinana radi liječenja predoziranja lijekom |
| EP2550253B9 (en) | 2010-03-22 | 2016-09-21 | Rensselaer Polytechnic Institute | Morphinane derivatives containing a carboxamide group as opioid receptor ligands |
| HUE065427T2 (hu) | 2010-08-23 | 2024-05-28 | Alkermes Pharma Ireland Ltd | Eljárások antipszichotikum által indukált súlygyarapodás kezelésére |
| PL2725908T3 (pl) * | 2011-06-29 | 2017-10-31 | Alkermes Inc | Działające obwodowo związki opioidowe |
| US9211293B2 (en) | 2011-12-15 | 2015-12-15 | Alkermes Pharma Ireland Limited | Opioid agonist antagonist combinations |
| WO2014190271A2 (en) | 2013-05-24 | 2014-11-27 | Alkermes Pharma Ireland Limted | Methods for treating depressive symptoms |
| AU2014268361B2 (en) | 2013-05-24 | 2018-09-06 | Alkermes Pharma Ireland Limited | Morphan and morphinan analogues, and methods of use |
| WO2022101444A1 (en) | 2020-11-12 | 2022-05-19 | Alkermes Pharma Ireland Limited | Immediate release multilayer tablet |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007014137A2 (en) * | 2005-07-21 | 2007-02-01 | Rensselaer Polytechnic Institute | 8-carboxamido-substituted-2 , 6-methano-3-benzazocines and 3 - carboxamido- substituted morphanes as opioid receptor binding agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60133584T2 (de) * | 2000-10-31 | 2009-06-04 | Rensselaer Polytechnic Institute | 4-arylpiperidine als opioidrezeptorbindende agenzien |
| AU2003281060A1 (en) * | 2002-07-16 | 2004-02-02 | Rensselaer Polytechnic Institute | Process for conversion of phenols to carboxamides via the succinimide esters |
| JP5727374B2 (ja) * | 2008-07-21 | 2015-06-03 | レンセラール ポリテクニック インスティチュート | 大型置換基を有する非フェノール性アミンオピオイド |
-
2009
- 2009-07-21 JP JP2011520127A patent/JP5727374B2/ja active Active
- 2009-07-21 CA CA2731429A patent/CA2731429C/en active Active
- 2009-07-21 US US12/506,354 patent/US20100190817A1/en not_active Abandoned
- 2009-07-21 ES ES09790652.3T patent/ES2534055T3/es active Active
- 2009-07-21 EP EP20090790652 patent/EP2318372B9/en active Active
- 2009-07-21 WO PCT/US2009/051200 patent/WO2010011619A1/en not_active Ceased
- 2009-07-21 AU AU2009274147A patent/AU2009274147B2/en active Active
-
2014
- 2014-10-03 JP JP2014204620A patent/JP2015044819A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007014137A2 (en) * | 2005-07-21 | 2007-02-01 | Rensselaer Polytechnic Institute | 8-carboxamido-substituted-2 , 6-methano-3-benzazocines and 3 - carboxamido- substituted morphanes as opioid receptor binding agents |
Non-Patent Citations (1)
| Title |
|---|
| VanAlstine, M. A. et al., Bioorganic & Medicinal Chemistry Letters, 2007, 17, pages 6516-6520 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015044819A (ja) | 2015-03-12 |
| ES2534055T9 (es) | 2016-05-31 |
| JP2011528718A (ja) | 2011-11-24 |
| ES2534055T3 (es) | 2015-04-16 |
| CA2731429A1 (en) | 2010-01-28 |
| US20100190817A1 (en) | 2010-07-29 |
| AU2009274147A1 (en) | 2010-01-28 |
| WO2010011619A1 (en) | 2010-01-28 |
| EP2318372B9 (en) | 2015-05-06 |
| JP5727374B2 (ja) | 2015-06-03 |
| EP2318372A1 (en) | 2011-05-11 |
| EP2318372B1 (en) | 2015-01-14 |
| CA2731429C (en) | 2016-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |