ES2282467T3 - Isoxazolpiridinonas. - Google Patents
Isoxazolpiridinonas. Download PDFInfo
- Publication number
- ES2282467T3 ES2282467T3 ES02772157T ES02772157T ES2282467T3 ES 2282467 T3 ES2282467 T3 ES 2282467T3 ES 02772157 T ES02772157 T ES 02772157T ES 02772157 T ES02772157 T ES 02772157T ES 2282467 T3 ES2282467 T3 ES 2282467T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- isoxazol
- pyridin
- methyl
- ylmethyl
- 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.)
- Expired - Lifetime
Links
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims abstract description 132
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- -1 6-biphenyl-4-yl-5-methyl-3-phenyl-5H-isoxazol Chemical compound 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- CBCQAYXVDWEMOH-UHFFFAOYSA-N CC1C=C(NO1)C1=CC=CC=C1C1=CC=C(C=C1)CN1CCN(CC1)C Chemical compound CC1C=C(NO1)C1=CC=CC=C1C1=CC=C(C=C1)CN1CCN(CC1)C CBCQAYXVDWEMOH-UHFFFAOYSA-N 0.000 claims abstract description 10
- IYFGPOBLVZTUKX-UHFFFAOYSA-N CN(C)CC1=CC=C(C=C1)C2=CC=CC=C2C3=CCON3 Chemical compound CN(C)CC1=CC=C(C=C1)C2=CC=CC=C2C3=CCON3 IYFGPOBLVZTUKX-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012458 free base Substances 0.000 claims abstract description 7
- OFINVCCMFOYTMR-UHFFFAOYSA-N CC1C=C(NO1)C2=CC=CC=C2C3=CC=C(C=C3)COCCOC Chemical compound CC1C=C(NO1)C2=CC=CC=C2C3=CC=C(C=C3)COCCOC OFINVCCMFOYTMR-UHFFFAOYSA-N 0.000 claims abstract description 6
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- CCYINEJZJLESKX-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazol-4-one Chemical compound CC1C(C(=NO1)C1=CC=CC=C1)=O CCYINEJZJLESKX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims abstract description 4
- HOINOAVAHHSVEV-UHFFFAOYSA-N C(C1=CC=CC=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1C=1NOC(C1)C Chemical compound C(C1=CC=CC=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1C=1NOC(C1)C HOINOAVAHHSVEV-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 229940052764 dopaminergic anti-parkinson drug mao b inhibitors Drugs 0.000 description 1
- 210000004002 dopaminergic cell Anatomy 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 description 1
- 229960003337 entacapone Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 238000005734 heterodimerization reaction Methods 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 230000009427 motor defect Effects 0.000 description 1
- MFDUBANTKQQBFU-UHFFFAOYSA-N n-methoxy-4-(2-methoxyethoxymethyl)-n-methylbenzamide Chemical compound COCCOCC1=CC=C(C(=O)N(C)OC)C=C1 MFDUBANTKQQBFU-UHFFFAOYSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 102000006255 nuclear receptors Human genes 0.000 description 1
- 108091008686 nuclear receptors type II Proteins 0.000 description 1
- 102000027507 nuclear receptors type II Human genes 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QVYRGXJJSLMXQH-UHFFFAOYSA-N orphenadrine Chemical compound C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 QVYRGXJJSLMXQH-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960003089 pramipexole Drugs 0.000 description 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229960003946 selegiline Drugs 0.000 description 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229960004603 tolcapone Drugs 0.000 description 1
- MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 239000003981 vehicle Substances 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0119911.6A GB0119911D0 (en) | 2001-08-15 | 2001-08-15 | Organic Compounds |
| GB0119911 | 2001-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2282467T3 true ES2282467T3 (es) | 2007-10-16 |
Family
ID=9920454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02772157T Expired - Lifetime ES2282467T3 (es) | 2001-08-15 | 2002-08-14 | Isoxazolpiridinonas. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US7087756B2 (enExample) |
| EP (1) | EP1418912B1 (enExample) |
| JP (1) | JP2005501847A (enExample) |
| KR (1) | KR20040029429A (enExample) |
| CN (1) | CN100384418C (enExample) |
| AR (1) | AR036351A1 (enExample) |
| AT (1) | ATE355059T1 (enExample) |
| BR (1) | BR0211903A (enExample) |
| CA (1) | CA2454762A1 (enExample) |
| CO (1) | CO5560566A2 (enExample) |
| DE (1) | DE60218484T2 (enExample) |
| EC (1) | ECSP044971A (enExample) |
| ES (1) | ES2282467T3 (enExample) |
| GB (1) | GB0119911D0 (enExample) |
| HU (1) | HUP0401325A3 (enExample) |
| IL (1) | IL160018A0 (enExample) |
| MX (1) | MXPA04001419A (enExample) |
| NO (1) | NO20040659D0 (enExample) |
| PE (1) | PE20030356A1 (enExample) |
| PL (1) | PL366848A1 (enExample) |
| PT (1) | PT1418912E (enExample) |
| RU (1) | RU2004107847A (enExample) |
| WO (1) | WO2003015780A2 (enExample) |
| ZA (1) | ZA200400525B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2451057A1 (en) * | 2001-06-14 | 2002-12-27 | Banyu Pharmaceutical Co., Ltd. | Novel isoxazolopyridone derivatives and use thereof |
| US7820705B2 (en) * | 2004-05-14 | 2010-10-26 | Irm Llc | Compounds and compositions as PPAR modulators |
| CA2642672A1 (en) * | 2006-02-16 | 2007-08-30 | The Mclean Hospital Corporation | Methods and compositions for the treatment of parkinson's disease |
| AU2007275301A1 (en) | 2006-07-20 | 2008-01-24 | Amgen Inc. | Substituted azole aromatic heterocycles as inhibitors of 11-beta-HSD-1 |
| FR2906250B1 (fr) * | 2006-09-22 | 2008-10-31 | Sanofi Aventis Sa | Derives de 2-aryl-6phenyl-imidazo(1,2-a) pyridines, leur preparation et leur application en therapeutique |
| FR2933609B1 (fr) | 2008-07-10 | 2010-08-27 | Fournier Lab Sa | Utilisation de derives d'indole comme activateurs de nurr-1, pour le traitement de la maladie de parkinson. |
| EP2376079B1 (en) * | 2009-01-13 | 2016-08-10 | Van Andel Research Institute | Methods of using substituted isoxazolo pyridinones as dissociated glucocorticoids |
| FR2950053B1 (fr) | 2009-09-11 | 2014-08-01 | Fournier Lab Sa | Utilisation de derives d'indole benzoique comme activateurs de nurr-1, pour le traitement de la maladie de parkinson |
| FR2955110A1 (fr) | 2010-01-08 | 2011-07-15 | Fournier Lab Sa | Nouveaux derives de type pyrrolopyridine benzoique |
| DE102011085038A1 (de) | 2011-10-21 | 2013-04-25 | Tesa Se | Verfahren zur Kapselung einer elektronischen Anordnung |
| WO2015048316A1 (en) | 2013-09-25 | 2015-04-02 | Van Andel Research Institute | Highly potent glucocorticoids |
| KR20170033630A (ko) | 2015-09-17 | 2017-03-27 | (주)다올 | 도로용 경계블럭 |
| JP7146750B2 (ja) | 2016-10-14 | 2022-10-04 | ヴァン アンデル リサーチ インスティテュート | 非常に強力な糖質コルチコイドの構造およびデザインのための機構 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7602542L (sv) | 1975-03-14 | 1976-09-15 | Sandoz Ag | 3-(alfa-iminobensyl)-4-hydroxi-2(lh)-pyridoner |
| US4064251A (en) * | 1976-06-25 | 1977-12-20 | Sandoz, Inc. | Substituted hydroxy pyridones |
| US4049813A (en) * | 1976-07-15 | 1977-09-20 | Sandoz, Inc. | Substituted isoxazolo pyridinones |
| DE2801190A1 (de) * | 1977-01-19 | 1978-07-20 | Sandoz Ag | 3-(alpha-iminobenzyl)-4-hydroxy-2(1h)- pyridon-derivat |
| US4238616A (en) * | 1977-01-19 | 1980-12-09 | Sandoz, Inc. | 3-(Substituted)phenyl-5-(β-hydroxyphenethyl)-N-(alkyl)-isoxazole-4-carboxamides |
| US4113727A (en) * | 1977-04-26 | 1978-09-12 | Sandoz, Inc. | Process for the preparation of substituted isoxazolo[4,5-c]pyridin-4-(5H)-ones |
| CA2451057A1 (en) * | 2001-06-14 | 2002-12-27 | Banyu Pharmaceutical Co., Ltd. | Novel isoxazolopyridone derivatives and use thereof |
-
2001
- 2001-08-15 GB GBGB0119911.6A patent/GB0119911D0/en not_active Ceased
-
2002
- 2002-08-13 AR ARP020103046A patent/AR036351A1/es unknown
- 2002-08-14 HU HU0401325A patent/HUP0401325A3/hu unknown
- 2002-08-14 US US10/486,569 patent/US7087756B2/en not_active Expired - Fee Related
- 2002-08-14 PL PL02366848A patent/PL366848A1/xx not_active Application Discontinuation
- 2002-08-14 PT PT02772157T patent/PT1418912E/pt unknown
- 2002-08-14 JP JP2003520739A patent/JP2005501847A/ja not_active Withdrawn
- 2002-08-14 WO PCT/EP2002/009134 patent/WO2003015780A2/en not_active Ceased
- 2002-08-14 BR BR0211903-0A patent/BR0211903A/pt not_active IP Right Cessation
- 2002-08-14 DE DE60218484T patent/DE60218484T2/de not_active Expired - Lifetime
- 2002-08-14 CN CNB028159268A patent/CN100384418C/zh not_active Expired - Fee Related
- 2002-08-14 MX MXPA04001419A patent/MXPA04001419A/es unknown
- 2002-08-14 CA CA002454762A patent/CA2454762A1/en not_active Abandoned
- 2002-08-14 AT AT02772157T patent/ATE355059T1/de not_active IP Right Cessation
- 2002-08-14 IL IL16001802A patent/IL160018A0/xx unknown
- 2002-08-14 EP EP02772157A patent/EP1418912B1/en not_active Expired - Lifetime
- 2002-08-14 PE PE2002000734A patent/PE20030356A1/es not_active Application Discontinuation
- 2002-08-14 KR KR10-2004-7002124A patent/KR20040029429A/ko not_active Ceased
- 2002-08-14 RU RU2004107847/15A patent/RU2004107847A/ru not_active Application Discontinuation
- 2002-08-14 ES ES02772157T patent/ES2282467T3/es not_active Expired - Lifetime
-
2004
- 2004-01-23 ZA ZA200400525A patent/ZA200400525B/en unknown
- 2004-02-03 EC EC2004004971A patent/ECSP044971A/es unknown
- 2004-02-13 NO NO20040659A patent/NO20040659D0/no not_active Application Discontinuation
- 2004-03-12 CO CO04023011A patent/CO5560566A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005501847A (ja) | 2005-01-20 |
| CO5560566A2 (es) | 2005-09-30 |
| DE60218484D1 (de) | 2007-04-12 |
| WO2003015780A3 (en) | 2003-11-13 |
| HUP0401325A2 (hu) | 2004-10-28 |
| WO2003015780A2 (en) | 2003-02-27 |
| MXPA04001419A (es) | 2004-05-27 |
| PL366848A1 (en) | 2005-02-07 |
| ZA200400525B (en) | 2005-04-01 |
| CN1635889A (zh) | 2005-07-06 |
| ATE355059T1 (de) | 2006-03-15 |
| DE60218484T2 (de) | 2007-11-15 |
| US7087756B2 (en) | 2006-08-08 |
| ECSP044971A (es) | 2004-03-23 |
| GB0119911D0 (en) | 2001-10-10 |
| NO20040659L (no) | 2004-02-13 |
| RU2004107847A (ru) | 2005-05-10 |
| CN100384418C (zh) | 2008-04-30 |
| BR0211903A (pt) | 2004-09-21 |
| CA2454762A1 (en) | 2003-02-27 |
| AR036351A1 (es) | 2004-09-01 |
| IL160018A0 (en) | 2004-06-20 |
| US20040248893A1 (en) | 2004-12-09 |
| PE20030356A1 (es) | 2003-05-14 |
| PT1418912E (pt) | 2007-05-31 |
| EP1418912A2 (en) | 2004-05-19 |
| EP1418912B1 (en) | 2007-02-28 |
| NO20040659D0 (no) | 2004-02-13 |
| HUP0401325A3 (en) | 2005-09-28 |
| KR20040029429A (ko) | 2004-04-06 |
| WO2003015780A8 (en) | 2004-05-21 |
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