JP2001514181A5 - - Google Patents
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- Publication number
- JP2001514181A5 JP2001514181A5 JP2000507675A JP2000507675A JP2001514181A5 JP 2001514181 A5 JP2001514181 A5 JP 2001514181A5 JP 2000507675 A JP2000507675 A JP 2000507675A JP 2000507675 A JP2000507675 A JP 2000507675A JP 2001514181 A5 JP2001514181 A5 JP 2001514181A5
- Authority
- JP
- Japan
- Prior art keywords
- naphthyridine
- oxo
- carboxamide
- tetrahydro
- ethoxy
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 description 51
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- 125000000753 cycloalkyl group Chemical group 0.000 description 25
- 229910052736 halogen Inorganic materials 0.000 description 24
- 150000002367 halogens Chemical group 0.000 description 24
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 125000003282 alkyl amino group Chemical group 0.000 description 16
- 150000002431 hydrogen Chemical group 0.000 description 15
- -1 hydroxy, amino Chemical group 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
- 0 C*c1c(*)c(O*)c(*)cc1 Chemical compound C*c1c(*)c(O*)c(*)cc1 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229960005235 piperonyl butoxide Drugs 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000000477 aza group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- MOUWZRIFUKBWQU-UHFFFAOYSA-N 6-(2-methoxyethoxy)-n-[[4-(methylaminomethyl)phenyl]methyl]-4-oxo-1h-1,5-naphthyridine-3-carboxamide Chemical compound C1=CC(CNC)=CC=C1CNC(=O)C1=CNC2=CC=C(OCCOC)N=C2C1=O MOUWZRIFUKBWQU-UHFFFAOYSA-N 0.000 description 1
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical group OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- UWMFDTSXDMUDSP-UHFFFAOYSA-N n-(2-ethylsulfanylethyl)-6-methoxy-4-oxo-1h-1,5-naphthyridine-3-carboxamide Chemical compound C1=C(OC)N=C2C(=O)C(C(=O)NCCSCC)=CNC2=C1 UWMFDTSXDMUDSP-UHFFFAOYSA-N 0.000 description 1
- ZKBBEESTQSXEPO-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-4-oxo-6-pyrrolidin-1-yl-1h-1,5-naphthyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CNC2=CC=C(N3CCCC3)N=C2C1=O ZKBBEESTQSXEPO-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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 |
|---|---|
| JP2001514181A JP2001514181A (ja) | 2001-09-11 |
| JP2001514181A5 true JP2001514181A5 (https=) | 2006-01-05 |
Family
ID=25439933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000507675A Pending JP2001514181A (ja) | 1997-08-25 | 1998-08-24 | Ｇａｂａ脳レセプタリガンドとしての置換４−オキソ−ナフチリジン−３−カルボキサミド |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1007526A1 (https=) |
| JP (1) | JP2001514181A (https=) |
| KR (1) | KR20010023313A (https=) |
| CN (1) | CN1268136A (https=) |
| AP (1) | AP2000001742A0 (https=) |
| AU (1) | AU753800B2 (https=) |
| BG (1) | BG104192A (https=) |
| BR (1) | BR9811362A (https=) |
| CA (1) | CA2301599C (https=) |
| EG (1) | EG21717A (https=) |
| HU (1) | HUP0003258A3 (https=) |
| IL (1) | IL134291A0 (https=) |
| IS (1) | IS5382A (https=) |
| LV (1) | LV12539B (https=) |
| NO (1) | NO20000822L (https=) |
| NZ (1) | NZ502548A (https=) |
| OA (1) | OA11293A (https=) |
| PE (1) | PE130999A1 (https=) |
| PL (1) | PL338783A1 (https=) |
| SI (1) | SI20270A (https=) |
| SK (1) | SK2162000A3 (https=) |
| TW (1) | TW574221B (https=) |
| WO (1) | WO1999010347A1 (https=) |
| YU (1) | YU10500A (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60018274T2 (de) * | 1999-05-06 | 2005-08-04 | Neurogen Corp., Branford | Substituierte 4-oxo-chinolin-3-carboxamide als gaba gehirnrezeptorliganden |
| WO2000071528A1 (en) * | 1999-05-25 | 2000-11-30 | Neurogen Corporation | 4h-1,4-benzothiazine-2-carboxamides and their use as gaba brain receptor ligands |
| 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 |
| US6730682B2 (en) | 2000-07-12 | 2004-05-04 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| EP1326611B1 (en) | 2000-10-12 | 2007-06-13 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl-carboxamides useful as hiv integrase inhibitors |
| ATE345129T1 (de) | 2000-10-12 | 2006-12-15 | Merck & Co Inc | Aza- und polyaza-naphthalenylcarbonsäureamide als hiv-integrase-hemmer |
| PL360944A1 (en) | 2000-10-12 | 2004-09-20 | 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 |
| CZ20032338A3 (cs) * | 2001-03-01 | 2004-08-18 | Pfizeráproductsáinc | Použití inversních agonistů GABA A v kombinaci s parciálními agonisty receptoru nikotinuŹ estrogenemŹ selektivními modulátory estrogenu nebo vitaminem E při léčení kognitivních poruch |
| AR036256A1 (es) | 2001-08-17 | 2004-08-25 | Merck & Co Inc | Sal sodica de un inhibidor de integrasa del vih, procesos para su preparacion, composiciones farmaceuticas que lo contienen y su uso para la manufactura de un medicamento |
| EP1467970B1 (en) | 2002-01-17 | 2007-08-22 | Merck & Co., Inc. | Hydroxynaphthyridinone carboxamides useful as hiv integrase inhibitors |
| ATE409187T1 (de) | 2002-03-15 | 2008-10-15 | Merck & Co Inc | N-(substituierte benzyl)-8-hydroxy-1,6- naphthyridin-7- carbonsäureamide als hiv- integrase-hemmer |
| 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 |
| NZ576036A (en) * | 2006-10-16 | 2010-10-29 | Bionomics Ltd | Naphthyridine containing compounds for treating anxiety disorders |
| PL2083811T3 (pl) * | 2006-11-22 | 2017-05-31 | Clinical Research Associates, Llc | Sposoby leczenia zespołu downa, zespołu łamliwego chromosomu x oraz autyzmu |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204813A1 (es) * | 1972-05-08 | 1976-03-05 | Yamanouchi Pharma Co Ltd | Proceso para la preparacion de derivados de ampilicina |
| 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 |
| DD279875A1 (de) * | 1987-07-03 | 1990-06-20 | Inst Pharmakologische Forschun | Verfahren zur herstellung von aktivierten carbonsaeureestern |
| DD279887A1 (de) * | 1987-07-03 | 1990-06-20 | Inst Pharmakologische Forschun | Verfahren zur herstellung von d-alpha-(4(1h)-1,5-naphthyridon-3-carboxamido)-benzylpenicillin und anderen beta-lactamantibiotika |
| DD295360A5 (de) * | 1987-07-03 | 1991-10-31 | Akad Wissenschaften | Verfahren zur Herstellung von aktivierten Carbonsäureestern |
| JPS6461461A (en) * | 1987-09-01 | 1989-03-08 | Otsuka Pharma Co Ltd | Benzohetero ring derivative |
-
1998
- 1998-08-24 KR KR1020007001948A patent/KR20010023313A/ko not_active Withdrawn
- 1998-08-24 CA CA002301599A patent/CA2301599C/en not_active Expired - Fee Related
- 1998-08-24 EP EP98943352A patent/EP1007526A1/en not_active Withdrawn
- 1998-08-24 WO PCT/US1998/017513 patent/WO1999010347A1/en not_active Ceased
- 1998-08-24 HU HU0003258A patent/HUP0003258A3/hu unknown
- 1998-08-24 CN CN98808578A patent/CN1268136A/zh active Pending
- 1998-08-24 PL PL98338783A patent/PL338783A1/xx unknown
- 1998-08-24 SK SK216-2000A patent/SK2162000A3/sk unknown
- 1998-08-24 SI SI9820055A patent/SI20270A/sl unknown
- 1998-08-24 BR BR9811362-3A patent/BR9811362A/pt not_active Application Discontinuation
- 1998-08-24 JP JP2000507675A patent/JP2001514181A/ja active Pending
- 1998-08-24 IL IL13429198A patent/IL134291A0/xx unknown
- 1998-08-24 NZ NZ502548A patent/NZ502548A/en unknown
- 1998-08-24 AU AU91173/98A patent/AU753800B2/en not_active Ceased
- 1998-08-24 YU YU10500A patent/YU10500A/sh unknown
- 1998-09-29 EG EG118098A patent/EG21717A/xx active
- 1998-10-23 TW TW87117597A patent/TW574221B/zh active
- 1998-11-13 PE PE1998001100A patent/PE130999A1/es not_active Application Discontinuation
-
2000
- 2000-02-01 AP APAP/P/2000/001742A patent/AP2000001742A0/en unknown
- 2000-02-18 NO NO20000822A patent/NO20000822L/no not_active Application Discontinuation
- 2000-02-18 OA OA1200000044A patent/OA11293A/en unknown
- 2000-02-22 IS IS5382A patent/IS5382A/is unknown
- 2000-02-25 BG BG104192A patent/BG104192A/xx unknown
- 2000-03-16 LV LVP-00-29A patent/LV12539B/en unknown
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