GB874206A - Basic derivatives of salicylamide - Google Patents
Basic derivatives of salicylamideInfo
- Publication number
- GB874206A GB874206A GB27670/57A GB2767057A GB874206A GB 874206 A GB874206 A GB 874206A GB 27670/57 A GB27670/57 A GB 27670/57A GB 2767057 A GB2767057 A GB 2767057A GB 874206 A GB874206 A GB 874206A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- group
- salicylamide
- acid
- nr2r3
- 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
Links
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 title abstract 3
- -1 alkyl radical Chemical group 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 229960000581 salicylamide Drugs 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 208000025747 Rheumatic disease Diseases 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 238000005574 benzylation reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 150000003891 oxalate salts Chemical class 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 230000000552 rheumatic effect Effects 0.000 abstract 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0874206/IV (b)/1> (wherein R1 is hydrogen or an alkyl radical of at most 4 carbon atoms, R2 and R3 are each alkyl radicals of at most 4 carbon atoms or form, together with the nitrogen, a saturated heterocyclic residue, such as a piperidino, pyrrolidino, morpholino or N-methyl-piperazino group, and X is an alkylene chain of 2 or 3 carbon atoms) and acid-addition salts thereof; and their preparation either by condencing salicyclic acid, or a functional derivative thereof, such as an ester or the acid chloride, with a diamine R1NH.X.NR2R3, with or without protection and subsequent release of the OH group, or by condensing salicylamide, or an N-R1-salicylamide, wherein the OH group is protected, with a halogenamine Hal.X.NR2R3 and subsequently releasing the OH group. Protection may be effected, for example, by acylation, the protecting group being removed by hydrolysis, or by benzylation or carbobenzoxylation, the group then being removed by hydrogenolysis. Examples are given, an intermediate being 2-benzyloxy-N - (b -diethylamino-ethyl) - benzamide hydrochloride.ALSO:Injection solutions, stated to be useful in the treatment of rheumatics, comprise water and an acid-addition salt of a substituted salicylamide of the formula <FORM:0874206/VI/1> wherein R1 is hydrogen or an alkyl radical of at most 4 carbon atoms, R2 and R3 are each alkyl radicals of at most 4 carbon atoms or form, together with the nitrogen, a saturated heterocyclic residue, and X is an alkylene chain of 2 or 3 carbon atoms). They may also contain substances such as 1-phenyl-2,3-dimethyl-4-dimethylamino-pyrazolone which act in a similar manner. Salts referred to are hydrochlorides and oxalates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE874206X | 1956-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB874206A true GB874206A (en) | 1961-08-02 |
Family
ID=6816809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27670/57A Expired GB874206A (en) | 1956-09-05 | 1957-09-02 | Basic derivatives of salicylamide |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB874206A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3261866A (en) * | 1962-09-20 | 1966-07-19 | Sahyun Melville | N-aminoalkyl-phenylsalicylamides |
| US3272861A (en) * | 1961-10-11 | 1966-09-13 | Continental Oil Co | Polyalkylene polyamine derivatives of hydroxybenzoic acid |
| WO1999050247A1 (en) * | 1998-03-31 | 1999-10-07 | Acadia Pharmaceuticals, Inc. | Compounds with activity on muscarinic receptors |
| US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
| EP1372615A1 (en) * | 2001-03-01 | 2004-01-02 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| WO2005035514A2 (en) * | 2003-10-08 | 2005-04-21 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters containing cycloalkyl or pyranyl groups |
| CN105439877A (en) * | 2006-07-26 | 2016-03-30 | 于崇曦 | Positively charged water-soluble prodrug of diflunisal and related compound |
-
1957
- 1957-09-02 GB GB27670/57A patent/GB874206A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272861A (en) * | 1961-10-11 | 1966-09-13 | Continental Oil Co | Polyalkylene polyamine derivatives of hydroxybenzoic acid |
| US3261866A (en) * | 1962-09-20 | 1966-07-19 | Sahyun Melville | N-aminoalkyl-phenylsalicylamides |
| WO1999050247A1 (en) * | 1998-03-31 | 1999-10-07 | Acadia Pharmaceuticals, Inc. | Compounds with activity on muscarinic receptors |
| US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
| US7485651B2 (en) | 1998-03-31 | 2009-02-03 | Acadia Pharmaceuticals, Inc. | Compounds with activity on muscarinic receptors |
| US7700775B2 (en) | 2001-03-01 | 2010-04-20 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| EP1372615A1 (en) * | 2001-03-01 | 2004-01-02 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| EP2308479A3 (en) * | 2001-03-01 | 2012-10-24 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| EP1372615A4 (en) * | 2001-03-01 | 2007-09-12 | Emisphere Tech Inc | COMPOUNDS AND COMPOSITIONS FOR THE DISPOSAL OF ACTIVE SUBSTANCES |
| WO2005035514A3 (en) * | 2003-10-08 | 2005-07-14 | Vertex Pharma | Modulators of atp-binding cassette transporters containing cycloalkyl or pyranyl groups |
| US7598412B2 (en) | 2003-10-08 | 2009-10-06 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| WO2005035514A2 (en) * | 2003-10-08 | 2005-04-21 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters containing cycloalkyl or pyranyl groups |
| CN105439877A (en) * | 2006-07-26 | 2016-03-30 | 于崇曦 | Positively charged water-soluble prodrug of diflunisal and related compound |
| CN105439877B (en) * | 2006-07-26 | 2019-07-23 | 于崇曦 | The prodrug of positively charged water-soluble Diflunisal and related compound |
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