ZA200603177B - Benzazepine derivatives as MAO-B inhibitors - Google Patents
Benzazepine derivatives as MAO-B inhibitors Download PDFInfo
- Publication number
- ZA200603177B ZA200603177B ZA200603177A ZA200603177A ZA200603177B ZA 200603177 B ZA200603177 B ZA 200603177B ZA 200603177 A ZA200603177 A ZA 200603177A ZA 200603177 A ZA200603177 A ZA 200603177A ZA 200603177 B ZA200603177 B ZA 200603177B
- Authority
- ZA
- South Africa
- Prior art keywords
- benzo
- hydrogen
- benzyloxy
- tetrahydro
- compound
- Prior art date
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- RKJMHZBROOPSPU-UHFFFAOYSA-N methyl 1h-azepine-3-carboxylate Chemical compound COC(=O)C1=CNC=CC=C1 RKJMHZBROOPSPU-UHFFFAOYSA-N 0.000 description 1
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- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229960003975 potassium Drugs 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical class CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical group C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000009529 traumatic brain injury Effects 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Nutrition Science (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Physiology (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03024297 | 2003-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200603177B true ZA200603177B (en) | 2007-09-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200603177A ZA200603177B (en) | 2003-10-23 | 2006-04-20 | Benzazepine derivatives as MAO-B inhibitors |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7173023B2 (fr) |
| EP (1) | EP1680127B1 (fr) |
| JP (1) | JP2007509094A (fr) |
| KR (1) | KR100856141B1 (fr) |
| CN (1) | CN100441188C (fr) |
| AR (1) | AR046133A1 (fr) |
| AT (1) | ATE411027T1 (fr) |
| AU (1) | AU2004283452A1 (fr) |
| BR (1) | BRPI0415842A (fr) |
| CA (1) | CA2543287A1 (fr) |
| CO (1) | CO5680409A2 (fr) |
| DE (1) | DE602004017206D1 (fr) |
| IL (1) | IL174845A0 (fr) |
| MX (1) | MXPA06004307A (fr) |
| NO (1) | NO20061907L (fr) |
| RU (1) | RU2006117366A (fr) |
| TW (1) | TWI254707B (fr) |
| WO (1) | WO2005039591A1 (fr) |
| ZA (1) | ZA200603177B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ATE441417T1 (de) | 2002-12-20 | 2009-09-15 | Glaxo Group Ltd | Benzoädüazepinderivate für die behandlung von neurologischen krankheiten |
| GB0408083D0 (en) * | 2004-04-08 | 2004-05-12 | Glaxo Group Ltd | Novel compounds |
| WO2007149728A2 (fr) * | 2006-06-20 | 2007-12-27 | Alcon Research, Ltd. | Dérivés d'aryl et d'hétéroaryl tétrahydrobenzazépine et leur utilisation pour traiter le glaucome |
| FR2932800B1 (fr) * | 2008-06-20 | 2015-02-20 | Servier Lab | Nouveau procede de synthese de la 7,8-dimethoxy-1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| KR101220182B1 (ko) | 2009-02-25 | 2013-01-11 | 에스케이바이오팜 주식회사 | 치환된 아졸 유도체 화합물, 이를 포함하는 약제학적 조성물 및 이를 이용한 파킨슨씨 병 치료방법 |
| RU2661156C2 (ru) | 2013-03-14 | 2018-07-12 | Дарт Нейросайенс (Кайман) Лтд. | Замещенные нафтиридиновые и хинолиновые соединения как ингибиторы мао |
| CN114437068A (zh) * | 2022-02-21 | 2022-05-06 | 深圳市儿童医院 | 一种萘啶衍生物及其作为单胺氧化酶抑制剂的用途 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1003753B (de) | 1953-11-07 | 1957-03-07 | Dr Karl Kindler | Verfahren zur Herstellung von N-Dialkylaminoacylaminophenolaethern |
| US3719669A (en) * | 1972-03-27 | 1973-03-06 | Pennwalt Corp | Amino(or amido)-phenyl-alkyl-benzazepine analgesics and narcotic antagonists |
| US4210749A (en) * | 1974-11-12 | 1980-07-01 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H,3 benzazepines |
| US4348393A (en) | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
| FR2500831A1 (fr) | 1981-02-27 | 1982-09-03 | Delalande Sa | Nouvelles n-aryl-oxazolidinones et -pyrrolidinones |
| US4524206A (en) | 1983-09-12 | 1985-06-18 | Mead Johnson & Company | 1-Heteroaryl-4-(2,5-pyrrolidinedion-1-yl)alkyl)piperazine derivatives |
| CA1261335A (fr) | 1984-08-29 | 1989-09-26 | Hoffmann-La Roche Limited/Hoffmann-La Roche Limitee | Derives d'ethylenediamine-monoamides |
| HUT43322A (en) | 1985-09-24 | 1987-10-28 | Schering Ag | Compositions with herbicidal effect comprising imidazolinyl derivatives as active substance and process for preparing the active substances |
| JPS6259973U (fr) | 1985-10-04 | 1987-04-14 | ||
| CA1332151C (fr) | 1988-01-28 | 1994-09-27 | Roman Amrein | Utilisation d'un benzamide dans le traitement d'un trouble cognitif |
| DE3834861A1 (de) | 1988-10-13 | 1990-04-19 | Basf Ag | Arylalkoxycumarine, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| JPH02142774A (ja) | 1988-11-25 | 1990-05-31 | Mitsui Toatsu Chem Inc | ２−（４−置換フェニル）イミダゾリノン類、その製造法、およびそれらを有効成分として含有する除草剤 |
| FR2645019A1 (fr) | 1989-03-30 | 1990-10-05 | Fournier Innovation Synergie | |
| IL94466A (en) | 1989-05-25 | 1995-01-24 | Erba Carlo Spa | Pharmaceutical preparations containing the history of A-amino carboxamide N-phenylalkyl are converted into such new compounds and their preparation |
| WO1992005163A1 (fr) | 1990-09-17 | 1992-04-02 | Pfizer Inc. | Oxazoles de 5-trifluorocylamino-2-aryle |
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-
2004
- 2004-10-14 BR BRPI0415842-3A patent/BRPI0415842A/pt not_active IP Right Cessation
- 2004-10-14 DE DE602004017206T patent/DE602004017206D1/de not_active Expired - Fee Related
- 2004-10-14 AU AU2004283452A patent/AU2004283452A1/en not_active Abandoned
- 2004-10-14 JP JP2006536004A patent/JP2007509094A/ja active Pending
- 2004-10-14 RU RU2006117366/04A patent/RU2006117366A/ru not_active Application Discontinuation
- 2004-10-14 EP EP04790400A patent/EP1680127B1/fr active Active
- 2004-10-14 CN CNB2004800309236A patent/CN100441188C/zh not_active Expired - Fee Related
- 2004-10-14 WO PCT/EP2004/011541 patent/WO2005039591A1/fr active Application Filing
- 2004-10-14 MX MXPA06004307A patent/MXPA06004307A/es not_active Application Discontinuation
- 2004-10-14 CA CA002543287A patent/CA2543287A1/fr not_active Abandoned
- 2004-10-14 KR KR1020067007779A patent/KR100856141B1/ko not_active IP Right Cessation
- 2004-10-14 AT AT04790400T patent/ATE411027T1/de not_active IP Right Cessation
- 2004-10-18 US US10/967,567 patent/US7173023B2/en not_active Expired - Fee Related
- 2004-10-20 TW TW093131855A patent/TWI254707B/zh not_active IP Right Cessation
- 2004-10-21 AR ARP040103808A patent/AR046133A1/es unknown
-
2006
- 2006-04-06 IL IL174845A patent/IL174845A0/en unknown
- 2006-04-18 CO CO06036626A patent/CO5680409A2/es not_active Application Discontinuation
- 2006-04-20 ZA ZA200603177A patent/ZA200603177B/en unknown
- 2006-04-28 NO NO20061907A patent/NO20061907L/no not_active Application Discontinuation
-
2007
- 2007-01-12 US US11/652,970 patent/US20070117791A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CO5680409A2 (es) | 2006-09-29 |
| EP1680127A1 (fr) | 2006-07-19 |
| CA2543287A1 (fr) | 2005-05-06 |
| JP2007509094A (ja) | 2007-04-12 |
| AR046133A1 (es) | 2005-11-23 |
| ATE411027T1 (de) | 2008-10-15 |
| EP1680127B1 (fr) | 2008-10-15 |
| BRPI0415842A (pt) | 2007-01-02 |
| NO20061907L (no) | 2006-07-12 |
| RU2006117366A (ru) | 2007-12-10 |
| TWI254707B (en) | 2006-05-11 |
| AU2004283452A1 (en) | 2005-05-06 |
| WO2005039591A1 (fr) | 2005-05-06 |
| DE602004017206D1 (de) | 2008-11-27 |
| MXPA06004307A (es) | 2006-06-05 |
| US20050107360A1 (en) | 2005-05-19 |
| CN100441188C (zh) | 2008-12-10 |
| KR100856141B1 (ko) | 2008-09-03 |
| US20070117791A1 (en) | 2007-05-24 |
| TW200524875A (en) | 2005-08-01 |
| US7173023B2 (en) | 2007-02-06 |
| IL174845A0 (en) | 2006-08-20 |
| CN1871013A (zh) | 2006-11-29 |
| KR20060061390A (ko) | 2006-06-07 |
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