EP0625144A1 - Pyridonderivate, ihre herstellung und Verwendung als Arzneimittel. - Google Patents
Pyridonderivate, ihre herstellung und Verwendung als Arzneimittel.Info
- Publication number
- EP0625144A1 EP0625144A1 EP93902251A EP93902251A EP0625144A1 EP 0625144 A1 EP0625144 A1 EP 0625144A1 EP 93902251 A EP93902251 A EP 93902251A EP 93902251 A EP93902251 A EP 93902251A EP 0625144 A1 EP0625144 A1 EP 0625144A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- pyridone
- hydrochloride
- benzylamidino
- benzyl
- amidino
- 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.)
- Withdrawn
Links
Classifications
-
- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Definitions
- Ar 1 is an optionally substituted phenyl ring
- Ar 2 i.s an optionally substituted phenyl ring
- R 1 is hydrogen or C 1-4 alkyl
- R 2 i.s hydrogen or C 1-4 alkyl
- R 3 i.s hydrogen or C 1-4 alkyl
- X is CH 2 or NR 6 in which R 6 is hydrogen or C 1-4 alkyl
- Ar is an optionally substituted phenyl ring.
- Suitable substituents for the phenyl ring Ar include, for example, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, halogen, cyano, amino, C 1-4 alkylamino, diC 1-4 alkylanri.no, hydroxy, carbamoyl, carboxy, C 1-6 alkanoyl trifluoromethyl, and
- Ar is unsubstituted phenyl, or phenyl substituted by a single substituent selected from C 1-6 alkyl, C 1-6 alkoxy or halogen.
- X is CH 2 or NR 6 ; preferably X is CH 2 or NR 6 in which R 6 is C 1-4 alkyl, in particular methyl.
- reaction between compounds of structure (II) and compounds of structure (III) can be carried out in a
- pharmaceutically acceptable salts exert an anti-secretory effect by inhibition of the gastrointestinal H K ATPase enzyme (Fellenius, E., Berglindh, T., Sachs, G., Olke, L., Elander, B., Sjostrand, S.E., and Wallmark, B., 1981, Nature, 290, 159-61 ) .
- the present invention provides compounds of structure (I) and pharmaceutically acceptable salts thereof for use in therapy.
- the compounds of structure (I) and their pharmaceutically acceptable salts inhibit exogenously and endogenously stimulated gastric acid secretion and are useful in the treatment of
- the compounds of the present invention are usually administered in a standard
- a typical suppository formulation comprises a compound of formula (I) or a pharmaceutically acceptable salt thereof which is active when administered in this way, with a binding and/or lubricating agent such as polymeric glycols, gelatins or cocoa butter or other low melting vegetable or synthetic waxes or fats.
- a binding and/or lubricating agent such as polymeric glycols, gelatins or cocoa butter or other low melting vegetable or synthetic waxes or fats.
- the present invention also provides a method of
- intramuscular dose of between 0.1 mg and 100 mg, preferably between 0.1 mg and 25 mg, of the compound of the formula (I) or a pharmaceutically acceptable salt thereof calculated as the free base, the compound being administered 1 to 4 times per day.
- the compounds will be administered for a period of continuous therapy, for example for a week or more.
- Helicobacter pylori organisms for example antibiotics such as amoxicillin.
- the compounds of examples 1 to 23 had IC 50 values of less than 20 ⁇ M.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929201694A GB9201694D0 (en) | 1992-01-27 | 1992-01-27 | Compounds |
| GB9201694 | 1992-01-27 | ||
| PCT/EP1993/000175 WO1993015056A1 (en) | 1992-01-27 | 1993-01-26 | Pyridone derivatives, their preparation and use as medicines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0625144A1 true EP0625144A1 (de) | 1994-11-23 |
Family
ID=10709307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP93902251A Withdrawn EP0625144A1 (de) | 1992-01-27 | 1993-01-26 | Pyridonderivate, ihre herstellung und Verwendung als Arzneimittel. |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0625144A1 (de) |
| JP (1) | JPH07503022A (de) |
| AU (1) | AU3352693A (de) |
| GB (1) | GB9201694D0 (de) |
| WO (1) | WO1993015056A1 (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| CN101801951B (zh) | 2007-09-14 | 2013-11-13 | 杨森制药有限公司 | 1’,3’-二取代的-4-苯基-3,4,5,6-四氢-2h,1’h-[1,4’]二吡啶-2’-酮 |
| RU2510396C2 (ru) | 2008-09-02 | 2014-03-27 | Янссен Фармасьютикалз, Инк. | 3-азабицикло[3.1.0]гексильные производные в качестве модуляторов метаботропных глутаматных рецепторов |
| AU2009319387B2 (en) | 2008-11-28 | 2012-05-10 | Addex Pharma S.A. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| RS53075B (en) | 2009-05-12 | 2014-04-30 | Janssen Pharmaceuticals Inc. | 1,2,4-TRIAZOLO [4,3-A] PYRIDINE DERIVATIVES AND THEIR USE IN THE TREATMENT OR PREVENTION OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS |
| JP5707390B2 (ja) | 2009-05-12 | 2015-04-30 | ジャンセン ファーマシューティカルズ， インコーポレイテッド | １，２，４−トリアゾロ［４，３−ａ］ピリジン誘導体およびｍＧｌｕＲ２受容体の正のアロステリック調節因子としてのその使用 |
| EP2643320B1 (de) | 2010-11-08 | 2015-03-04 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridinderivate und ihre verwendung als positiv allosterische modulatoren des mglur2 receptors |
| EP2649069B1 (de) | 2010-11-08 | 2015-08-26 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazol[4,3-a]pyridinderivate und ihre verwendung als positive allosterische mglur2-rezeptormodulatoren |
| EP2661435B1 (de) | 2010-11-08 | 2015-08-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazol[4,3-a]pyridinderivate und ihre verwendung als positive allosterische mglur2-rezeptormodulatoren |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| DK3431106T3 (da) | 2014-01-21 | 2021-03-15 | Janssen Pharmaceutica Nv | Kombinationer omfattende positive allosteriske modulatorer eller orthosteriske agonister af metabotrop glutamaterg subtype 2-receptor og anvendelse af disse |
| ES2860298T3 (es) | 2014-01-21 | 2021-10-04 | Janssen Pharmaceutica Nv | Combinaciones que comprenden moduladores alostéricos positivos del receptor glutamatérgico metabotrópico de subtipo 2 y su uso |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299081A (en) * | 1963-09-13 | 1967-01-17 | Merck & Co Inc | Chemical processes for preparing nu-substituted amidines |
| US4028084A (en) * | 1974-10-11 | 1977-06-07 | Rohm And Haas Company | Derivatives of 3-carboxy pyrid-2-ones |
| US4284768A (en) * | 1980-07-02 | 1981-08-18 | American Home Products Corporation | 1,2-Dihydro-4-amino-2-oxo-3-quinoline-carboxylic acid derivatives |
| GB8804445D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| IL100917A0 (en) * | 1991-02-16 | 1992-11-15 | Fisons Plc | Pyridinone and pyrimidinone derivatives,their preparation and pharmaceutical compositions containing them |
-
1992
- 1992-01-27 GB GB929201694A patent/GB9201694D0/en active Pending
-
1993
- 1993-01-26 WO PCT/EP1993/000175 patent/WO1993015056A1/en not_active Application Discontinuation
- 1993-01-26 AU AU33526/93A patent/AU3352693A/en not_active Abandoned
- 1993-01-26 JP JP5512930A patent/JPH07503022A/ja active Pending
- 1993-01-26 EP EP93902251A patent/EP0625144A1/de not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9315056A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3352693A (en) | 1993-09-01 |
| GB9201694D0 (en) | 1992-03-11 |
| JPH07503022A (ja) | 1995-03-30 |
| WO1993015056A1 (en) | 1993-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19940624 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): BE CH DE FR GB IT LI NL |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 19960801 |
|
| RBV | Designated contracting states (corrected) |
Designated state(s): BE CH DE FR GB IT LI NL |