CA2301599A1 - Substituted 4-oxo-napthyridine-3-carboxamides as gaba brain receptor ligands - Google Patents
Substituted 4-oxo-napthyridine-3-carboxamides as gaba brain receptor ligands Download PDFInfo
- Publication number
- CA2301599A1 CA2301599A1 CA002301599A CA2301599A CA2301599A1 CA 2301599 A1 CA2301599 A1 CA 2301599A1 CA 002301599 A CA002301599 A CA 002301599A CA 2301599 A CA2301599 A CA 2301599A CA 2301599 A1 CA2301599 A1 CA 2301599A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- napthyridine
- carboxamides
- oxo
- agonists
- 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.)
- Granted
Links
- 210000004556 brain Anatomy 0.000 title abstract 3
- 239000003446 ligand Substances 0.000 title 1
- 239000000556 agonist Substances 0.000 abstract 4
- 239000005557 antagonist Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 abstract 1
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 201000010374 Down Syndrome Diseases 0.000 abstract 1
- 230000036626 alertness Effects 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229940049706 benzodiazepine Drugs 0.000 abstract 1
- 208000010877 cognitive disease Diseases 0.000 abstract 1
- 230000001149 cognitive effect Effects 0.000 abstract 1
- 238000003745 diagnosis Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 206010015037 epilepsy Diseases 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 208000019116 sleep disease Diseases 0.000 abstract 1
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/08—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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention encompasses structures of Formula (I) or the pharmaceutically acceptable non-toxic salts thereof wherein: X is hydrogen, halogen, (un)substituted alkyl, (un)substituted alkoxy or amino; and Y is (un)substituted alkyl, aryl, or heteroaryl, which compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compounds are useful in the diagnosis and treatment of anxiety, Down Syndrome, sleep, cognitive and seizure disorders, and overdose with benzodiazepine drugs and for enhancement of alertness.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91818097A | 1997-08-25 | 1997-08-25 | |
| US08/918,180 | 1997-08-25 | ||
| PCT/US1998/017513 WO1999010347A1 (en) | 1997-08-25 | 1998-08-24 | Substituted 4-oxo-napthyridine-3-carboxamides as gaba brain receptor ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2301599A1 true CA2301599A1 (en) | 1999-03-04 |
| CA2301599C CA2301599C (en) | 2003-03-25 |
Family
ID=25439933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002301599A Expired - Fee Related CA2301599C (en) | 1997-08-25 | 1998-08-24 | Substituted 4-oxo-napthyridine-3-carboxamides as gaba brain receptor ligands |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1007526A1 (en) |
| JP (1) | JP2001514181A (en) |
| KR (1) | KR20010023313A (en) |
| CN (1) | CN1268136A (en) |
| AP (1) | AP2000001742A0 (en) |
| AU (1) | AU753800B2 (en) |
| BG (1) | BG104192A (en) |
| BR (1) | BR9811362A (en) |
| CA (1) | CA2301599C (en) |
| EG (1) | EG21717A (en) |
| HU (1) | HUP0003258A3 (en) |
| IL (1) | IL134291A0 (en) |
| IS (1) | IS5382A (en) |
| LV (1) | LV12539B (en) |
| NO (1) | NO20000822L (en) |
| NZ (1) | NZ502548A (en) |
| OA (1) | OA11293A (en) |
| PE (1) | PE130999A1 (en) |
| PL (1) | PL338783A1 (en) |
| SI (1) | SI20270A (en) |
| SK (1) | SK2162000A3 (en) |
| TW (1) | TW574221B (en) |
| WO (1) | WO1999010347A1 (en) |
| YU (1) | YU10500A (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4818000A (en) * | 1999-05-06 | 2000-11-21 | Neurogen Corporation | Substituted 4-oxo-quinoline-3-carboxamides: gaba brain receptor ligands |
| WO2000071528A1 (en) * | 1999-05-25 | 2000-11-30 | Neurogen Corporation | 4h-1,4-benzothiazine-2-carboxamides and their use as gaba brain receptor ligands |
| US6730682B2 (en) | 2000-07-12 | 2004-05-04 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| US6559145B2 (en) | 2000-07-12 | 2003-05-06 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| US6562822B2 (en) | 2000-07-12 | 2003-05-13 | Pharmacia & Upjohn Company | Heterocyle carboxamides as antiviral agents |
| ES2287170T3 (en) | 2000-10-12 | 2007-12-16 | MERCK & CO., INC. | AZA- AND POLIAZA-NAFTALENIL-CARBOXAMIDAS UTILIES AS INHIBITORS OF INTEGRATED HIV. |
| CA2425625A1 (en) | 2000-10-12 | 2002-07-18 | Merck & Co., Inc. | Aza-and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| WO2002030930A2 (en) | 2000-10-12 | 2002-04-18 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| US20020151591A1 (en) * | 2000-10-17 | 2002-10-17 | Anabella Villalobos | Combination use of acetylcholinesterase inhibitors and GABAa inverse agonists for the treatment of cognitive disorders |
| SK10752003A3 (en) * | 2001-03-01 | 2004-08-03 | Pfizer Products Inc. | Use of GABAA inverse agonists in combination with nicotine receptor partial agonists, estrogen, selective estrogen modulators, or vitamin E for the treatment of cognitive disorders |
| AR036256A1 (en) | 2001-08-17 | 2004-08-25 | Merck & Co Inc | SODIUM SALT OF AN HIV INTEGRAS INHIBITOR, PROCESSES FOR PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING IT AND ITS USE FOR THE MANUFACTURE OF A MEDICINAL PRODUCT |
| ATE370948T1 (en) | 2002-01-17 | 2007-09-15 | Merck & Co Inc | HYDROXYNAPHTHYRIDINONCARBONIC ACID AMIDES, WHICH ARE SUITABLE AS INHIBITORS OF HIV INTEGRASE |
| WO2003077850A2 (en) | 2002-03-15 | 2003-09-25 | Merck & Co., Inc. | N-(substituted benzyl)-8-hydroxy-1,6-naphthyridine-7- carboxamides useful as hiv integrase inhibitors |
| WO2004106336A1 (en) * | 2003-05-27 | 2004-12-09 | Pfizer Products Inc. | Process for the preparation and purification of 1,5-naphthyridine-3-carboxyamides |
| WO2004106334A2 (en) * | 2003-05-28 | 2004-12-09 | Pfizer Products Inc. | Process for the preparation of 1,5-naphthyridine-3-carboxy amides by direct ester amidation |
| PL2074123T3 (en) * | 2006-10-16 | 2013-04-30 | Bionomics Ltd | Novel anxiolytic compounds |
| ES2610508T3 (en) * | 2006-11-22 | 2017-04-27 | Clinical Research Associates, Llc | Methods to treat Down syndrome, fragile X syndrome and autism |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204813A1 (en) * | 1972-05-08 | 1976-03-05 | Yamanouchi Pharma Co Ltd | PROCESS FOR THE PREPARATION OF AMPYLICIN DERIVATIVES |
| GB1433774A (en) * | 1973-02-26 | 1976-04-28 | Allen & Hanburys Ltd | Heterocyclic compounds apparatus for conveying articles |
| US4374138A (en) * | 1981-11-13 | 1983-02-15 | Warner-Lambert Company | Antibacterial amide compounds, compositions, and methods of use |
| DD295360A5 (en) * | 1987-07-03 | 1991-10-31 | Akad Wissenschaften | Process for the preparation of activated carboxylic acid esters |
| DD279887A1 (en) * | 1987-07-03 | 1990-06-20 | Inst Pharmakologische Forschun | METHOD OF PREPARING D-ALPHA- (4 (1H) -1,5-NAPHTHYRIDONE-3-CARBOXAMIDO) -BENZYLPENICILLIN AND OTHER BETA LACTAMANTIBIOTICS |
| DD279875A1 (en) * | 1987-07-03 | 1990-06-20 | Inst Pharmakologische Forschun | PROCESS FOR PREPARING ACTIVATED CARBONIC ACID ESTERS |
| JPS6461461A (en) * | 1987-09-01 | 1989-03-08 | Otsuka Pharma Co Ltd | Benzohetero ring derivative |
-
1998
- 1998-08-24 WO PCT/US1998/017513 patent/WO1999010347A1/en not_active Application Discontinuation
- 1998-08-24 SI SI9820055A patent/SI20270A/en unknown
- 1998-08-24 CA CA002301599A patent/CA2301599C/en not_active Expired - Fee Related
- 1998-08-24 HU HU0003258A patent/HUP0003258A3/en unknown
- 1998-08-24 EP EP98943352A patent/EP1007526A1/en not_active Withdrawn
- 1998-08-24 PL PL98338783A patent/PL338783A1/en unknown
- 1998-08-24 YU YU10500A patent/YU10500A/en unknown
- 1998-08-24 CN CN98808578A patent/CN1268136A/en active Pending
- 1998-08-24 AU AU91173/98A patent/AU753800B2/en not_active Ceased
- 1998-08-24 KR KR1020007001948A patent/KR20010023313A/en not_active Application Discontinuation
- 1998-08-24 SK SK216-2000A patent/SK2162000A3/en unknown
- 1998-08-24 BR BR9811362-3A patent/BR9811362A/en not_active Application Discontinuation
- 1998-08-24 JP JP2000507675A patent/JP2001514181A/en active Pending
- 1998-08-24 IL IL13429198A patent/IL134291A0/en unknown
- 1998-08-24 NZ NZ502548A patent/NZ502548A/en unknown
- 1998-09-29 EG EG118098A patent/EG21717A/en active
- 1998-10-23 TW TW87117597A patent/TW574221B/en active
- 1998-11-13 PE PE1998001100A patent/PE130999A1/en not_active Application Discontinuation
-
2000
- 2000-02-01 AP APAP/P/2000/001742A patent/AP2000001742A0/en unknown
- 2000-02-18 OA OA1200000044A patent/OA11293A/en unknown
- 2000-02-18 NO NO20000822A patent/NO20000822L/en not_active Application Discontinuation
- 2000-02-22 IS IS5382A patent/IS5382A/en unknown
- 2000-02-25 BG BG104192A patent/BG104192A/en unknown
- 2000-03-16 LV LVP-00-29A patent/LV12539B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU753800B2 (en) | 2002-10-31 |
| BG104192A (en) | 2001-05-31 |
| NO20000822L (en) | 2000-04-13 |
| TW574221B (en) | 2004-02-01 |
| SI20270A (en) | 2000-12-31 |
| PL338783A1 (en) | 2000-11-20 |
| LV12539B (en) | 2001-01-20 |
| CA2301599C (en) | 2003-03-25 |
| JP2001514181A (en) | 2001-09-11 |
| PE130999A1 (en) | 1999-12-16 |
| BR9811362A (en) | 2000-08-22 |
| NZ502548A (en) | 2002-06-28 |
| LV12539A (en) | 2000-10-20 |
| NO20000822D0 (en) | 2000-02-18 |
| IS5382A (en) | 2000-02-22 |
| OA11293A (en) | 2002-11-19 |
| HUP0003258A2 (en) | 2001-03-28 |
| YU10500A (en) | 2002-10-18 |
| AP2000001742A0 (en) | 2000-02-24 |
| SK2162000A3 (en) | 2001-03-12 |
| IL134291A0 (en) | 2001-04-30 |
| WO1999010347A1 (en) | 1999-03-04 |
| KR20010023313A (en) | 2001-03-26 |
| EP1007526A1 (en) | 2000-06-14 |
| EG21717A (en) | 2002-02-27 |
| HUP0003258A3 (en) | 2001-05-28 |
| AU9117398A (en) | 1999-03-16 |
| CN1268136A (en) | 2000-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |