CA2558741A1 - Benzoxazocines et utilisation therapeutique de celles-ci comme inhibiteurs du recaptage de la monoamine - Google Patents

Benzoxazocines et utilisation therapeutique de celles-ci comme inhibiteurs du recaptage de la monoamine Download PDF

Info

Publication number: CA2558741A1
Authority: CA; Canada
Prior art keywords: methyl; phenyl; tetrahydro; oxazocine; benz
Prior art date: 2004-04-21
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

Application number

CA002558741A

Other languages

English (en)

Inventor

Andrew Douglas Baxter

Andrea Walmsley

Elena Lasterra

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.)

Sosei R&D Ltd

Original Assignee

Individual

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.)

2004-04-21

Filing date

2005-04-21

Publication date

2005-11-03

2004-04-21 Priority claimed from GB0408862A external-priority patent/GB0408862D0/en

2004-04-21 Priority claimed from GB0408863A external-priority patent/GB0408863D0/en

2005-04-21 Application filed by Individual filed Critical Individual

2005-11-03 Publication of CA2558741A1 publication Critical patent/CA2558741A1/fr

Status Abandoned legal-status Critical Current

Links

230000000407 monoamine reuptake Effects 0.000 title claims description 9
230000001225 therapeutic effect Effects 0.000 title abstract description 7
SFVYUAJWNYVQDB-UHFFFAOYSA-N 2h-1,2-benzoxazocine Chemical class O1NC=CC=CC2=CC=CC=C21 SFVYUAJWNYVQDB-UHFFFAOYSA-N 0.000 title description 2
239000003112 inhibitor Substances 0.000 title description 2
125000003118 aryl group Chemical group 0.000 claims abstract description 74
150000001875 compounds Chemical class 0.000 claims abstract description 59
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 29
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
125000005842 heteroatom Chemical group 0.000 claims abstract description 15
229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
229910020008 S(O) Inorganic materials 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 3
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CBBJVHOKVPTECQ-UHFFFAOYSA-N 9-bromo-1-(7-methyl-1,3-benzodioxol-5-yl)-2,3,5,6-tetrahydro-4,1-benzoxazocine Chemical compound C1COCCC2=CC=C(Br)C=C2N1C(C=C1C)=CC2=C1OCO2 CBBJVHOKVPTECQ-UHFFFAOYSA-N 0.000 claims description 3
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FMOQQJXGQNJWSL-UHFFFAOYSA-N 1-phenyl-5-propyl-2,3,5,6-tetrahydro-4,1-benzoxazocine Chemical compound C1COC(CCC)CC2=CC=CC=C2N1C1=CC=CC=C1 FMOQQJXGQNJWSL-UHFFFAOYSA-N 0.000 claims description 2
NYKARRSFRBYNSU-UHFFFAOYSA-N 10-fluoro-5-methyl-1-phenyl-2,3,5,6-tetrahydro-4,1-benzoxazocine Chemical compound C1COC(C)CC2=CC=CC(F)=C2N1C1=CC=CC=C1 NYKARRSFRBYNSU-UHFFFAOYSA-N 0.000 claims description 2
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FSXRPWGCYSQLOX-UHFFFAOYSA-N 1-(7-methyl-1,3-benzodioxol-5-yl)-2,3,5,6-tetrahydro-4,1-benzoxazocine-8-carbonitrile Chemical compound C1COCCC2=CC(C#N)=CC=C2N1C(C=C1C)=CC2=C1OCO2 FSXRPWGCYSQLOX-UHFFFAOYSA-N 0.000 claims 1
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PYTUJXZRSGSVFW-UHFFFAOYSA-N 5-benzyl-1-phenyl-2,3,5,6-tetrahydro-4,1-benzoxazocine Chemical compound C=1C=CC=CC=1CC(OCC1)CC2=CC=CC=C2N1C1=CC=CC=C1 PYTUJXZRSGSVFW-UHFFFAOYSA-N 0.000 claims 1
WHJXTIWMKGKPJW-UHFFFAOYSA-N 8-bromo-5-methyl-1-pyridin-3-yl-2,3,5,6-tetrahydro-4,1-benzoxazocine Chemical compound C1COC(C)CC2=CC(Br)=CC=C2N1C1=CC=CN=C1 WHJXTIWMKGKPJW-UHFFFAOYSA-N 0.000 claims 1
YAPRYVWCKXMDIQ-UHFFFAOYSA-N 8-cyclopropyl-1-(7-methyl-1,3-benzodioxol-5-yl)-2,3,5,6-tetrahydro-4,1-benzoxazocine Chemical compound C=1C=2OCOC=2C(C)=CC=1N(C1=CC=2)CCOCCC1=CC=2C1CC1 YAPRYVWCKXMDIQ-UHFFFAOYSA-N 0.000 claims 1
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HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims 1
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230000003111 delayed effect Effects 0.000 claims 1
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229910052739 hydrogen Inorganic materials 0.000 abstract description 221
229910052799 carbon Inorganic materials 0.000 abstract description 11
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
230000000697 serotonin reuptake Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
235000019798 tripotassium phosphate Nutrition 0.000 description 1
NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000007514 turning Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- 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
- A61P25/04—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
- A61P25/06—Antimigraine 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
- A61P25/24—Antidepressants
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00

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)
Biomedical Technology (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Endocrinology (AREA)
Psychiatry (AREA)
Addiction (AREA)
Reproductive Health (AREA)
Gynecology & Obstetrics (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Plant Substances (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA002558741A 2004-04-21 2005-04-21 Benzoxazocines et utilisation therapeutique de celles-ci comme inhibiteurs du recaptage de la monoamine Abandoned CA2558741A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB0408862A GB0408862D0 (en)	2004-04-21	2004-04-21	Novel benzoxazocines
GB0408862.1		2004-04-21
GB0408863.9		2004-04-21
GB0408863A GB0408863D0 (en)	2004-04-21	2004-04-21	Novel benzoxazocines
PCT/GB2005/001519 WO2005103019A1 (fr)	2004-04-21	2005-04-21	Benzoxazocines et utilisation therapeutique de celles-ci comme inhibiteurs du recaptage de la monoamine

Publications (1)

Publication Number	Publication Date
CA2558741A1 true CA2558741A1 (fr)	2005-11-03

Family

ID=34965745

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002558741A Abandoned CA2558741A1 (fr)	2004-04-21	2005-04-21	Benzoxazocines et utilisation therapeutique de celles-ci comme inhibiteurs du recaptage de la monoamine

Country Status (8)

Country	Link
EP (1)	EP1740558A1 (fr)
JP (1)	JP2007533718A (fr)
AU (1)	AU2005235786A1 (fr)
BR (1)	BRPI0510075A (fr)
CA (1)	CA2558741A1 (fr)
IL (1)	IL177750A0 (fr)
NO (1)	NO20065057L (fr)
WO (1)	WO2005103019A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0504960D0 (en) *	2005-03-10	2005-04-20	Arakis Ltd	Benzoxazocines
GB0506835D0 (en) *	2005-04-04	2005-05-11	Arakis Ltd	Therapeutic use of nefopam
US8957107B2 (en)	2009-12-15	2015-02-17	The Hospital For Sick Children	Method of treating scars and β-catenin-mediated disorders using Nefopam compounds
WO2012007500A2 (fr)	2010-07-15	2012-01-19	Bayer Cropscience Ag	Nouveaux composés hétérocycliques servant d'agents de lutte contre les nuisibles

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3830803A (en) *	1965-05-10	1974-08-20	Riker Laboratories Inc	5-loweralkyl-1-phenyl-1,3,4,6-tetrahydro-5h-benz(f)-2,5-oxazocines and 4-ones
US3978085A (en) *	1975-03-07	1976-08-31	Riker Laboratories, Inc.	Process for benz[f]-2,5-oxazocines
JPS5913770A (ja) *	1982-07-13	1984-01-24	Sanwa Kagaku Kenkyusho:Kk	新規の１−フエニル−２，５−ベンゾチアゾシン誘導体及びその製法
JPS5913760A (ja) *	1982-07-13	1984-01-24	Sanwa Kagaku Kenkyusho:Kk	新規の２−ベンズアゾシン誘導体及びその製法
MXPA02004330A (es) *	1999-11-03	2004-07-30	Albany Molecular Res Inc	Tetrahidroisoquinolinas aril-y heteroaril-sustituidas y uso de las mismas para bloquear la recaptacion de norepinefrina, dopamina y serotonina..
AU2003295171B2 (en) *	2002-12-20	2007-09-06	Arakis Ltd.	Benzoxazocines and their use as monoamine-reuptake inhibitors

2005
- 2005-04-21 BR BRPI0510075-5A patent/BRPI0510075A/pt not_active IP Right Cessation
- 2005-04-21 EP EP05736028A patent/EP1740558A1/fr not_active Withdrawn
- 2005-04-21 WO PCT/GB2005/001519 patent/WO2005103019A1/fr not_active Ceased
- 2005-04-21 AU AU2005235786A patent/AU2005235786A1/en not_active Abandoned
- 2005-04-21 CA CA002558741A patent/CA2558741A1/fr not_active Abandoned
- 2005-04-21 JP JP2007508968A patent/JP2007533718A/ja not_active Withdrawn
2006
- 2006-08-29 IL IL177750A patent/IL177750A0/en unknown
- 2006-11-02 NO NO20065057A patent/NO20065057L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
IL177750A0 (en)	2006-12-31
JP2007533718A (ja)	2007-11-22
WO2005103019A1 (fr)	2005-11-03
AU2005235786A1 (en)	2005-11-03
BRPI0510075A (pt)	2007-10-16
EP1740558A1 (fr)	2007-01-10
NO20065057L (no)	2006-11-21

Legal Events

Date	Code	Title	Description
2010-04-21	FZDE	Discontinued

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CA2558741A1 (fr)	2005-11-03	Benzoxazocines et utilisation therapeutique de celles-ci comme inhibiteurs du recaptage de la monoamine
US20060019940A1 (en)	2006-01-26	Novel benzoxazocines and their therapeutic use
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HK1075896B (en)	2009-04-30	Benzoxazocines and their use as monoamine-reuptake inhibitors
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