GB1047028A - Improvements in or relating to 5-acetamido-salicylamide derivatives - Google Patents
Improvements in or relating to 5-acetamido-salicylamide derivativesInfo
- Publication number
- GB1047028A GB1047028A GB45248/63A GB4524863A GB1047028A GB 1047028 A GB1047028 A GB 1047028A GB 45248/63 A GB45248/63 A GB 45248/63A GB 4524863 A GB4524863 A GB 4524863A GB 1047028 A GB1047028 A GB 1047028A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- acetamido
- acetoxy
- reaction
- alkyl
- 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
- YXRPUZIIKDKSNR-UHFFFAOYSA-N 5-acetamido-2-hydroxybenzamide Chemical class CC(=O)NC1=CC=C(O)C(C(N)=O)=C1 YXRPUZIIKDKSNR-UHFFFAOYSA-N 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- WBNCOMNWLPBONU-UHFFFAOYSA-N (4-acetamido-2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)NC1=CC=C(OC(C)=O)C(C(Cl)=O)=C1 WBNCOMNWLPBONU-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract 1
- LPEQUXVADBGZCC-UHFFFAOYSA-N 5-acetamido-2-acetyloxybenzoic acid Chemical compound CC(=O)NC1=CC=C(OC(C)=O)C(C(O)=O)=C1 LPEQUXVADBGZCC-UHFFFAOYSA-N 0.000 abstract 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000002927 anti-mitotic effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 230000003385 bacteriostatic effect Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- -1 furyl-alkyl Chemical group 0.000 abstract 1
- 230000002005 ganglioplegic effect Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000000147 hypnotic effect Effects 0.000 abstract 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 abstract 1
- 229960004963 mesalazine Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of formula <F\1> wherein R is a hydrogen atom or a -CH2CH = CH2, -CH2CH = CHCH3, -CH2CCH, -CH2-CH2NR1R2 or -CH2CONR1R2 group, R1 and R2 being alkyl groups or the group -NR1R2 forming a heterocycle which may contain an oxygen atom, and R3 and R4 are hydrogen atoms or alkyl, furyl-alkyl, hydroxyalkyl or cycloalkyl groups, provided that R3 and R4 are not both hydrogen atoms, or the group NR3R4 forms a heterocycle which may contain an oxygen atom, and acid addition salts thereof, and their preparation by reaction of 2-acetoxy-5acetamido-benzoyl chloride with an amine HNR3R4, followed, if desired, by etherification of the so-obtained 2-hydroxy group by reaction with the appropriate halide. 2-Acetoxy-5-acetamido-benzoyl chloride is prepared by reaction of 5-amino-salicylic acid with acetic anhydride to form 2-acetoxy-5-acetamido-benzoic acid, followed by treatment of this with thionyl chloride. The compounds of the invention have anti-pyretic, analgesic, anti-inflammatory, hypnotic, ganglioplegic, anti-mitotic and bacteriostatic activity and may be used in pharmaceutical compositions in combination with a carrier.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45248/63A GB1047028A (en) | 1963-11-15 | 1963-11-15 | Improvements in or relating to 5-acetamido-salicylamide derivatives |
| BR16424964A BR6464249D0 (en) | 1963-11-15 | 1964-11-12 | PROCESS FOR THE PREPARATION OF NEW 5-ACETAMINE-SALICYLAMIDE DERIVATIVES |
| FR1565309D FR1565309A (en) | 1963-11-15 | 1964-11-13 | |
| FR994967A FR3909M (en) | 1963-11-15 | 1964-11-13 | |
| BE655710D BE655710A (en) | 1963-11-15 | 1964-11-13 | |
| DE19641518287 DE1518287A1 (en) | 1963-11-15 | 1964-11-16 | New derivatives of 5-acetamidosalicylamide and their preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45248/63A GB1047028A (en) | 1963-11-15 | 1963-11-15 | Improvements in or relating to 5-acetamido-salicylamide derivatives |
| GB2195264 | 1964-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1047028A true GB1047028A (en) | 1966-11-02 |
Family
ID=26255620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB45248/63A Expired GB1047028A (en) | 1963-11-15 | 1963-11-15 | Improvements in or relating to 5-acetamido-salicylamide derivatives |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE655710A (en) |
| BR (1) | BR6464249D0 (en) |
| DE (1) | DE1518287A1 (en) |
| FR (2) | FR1565309A (en) |
| GB (1) | GB1047028A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795832A (en) * | 1986-10-02 | 1989-01-03 | Henkel Kommanditgesellschaft Auf Aktien | Salicylic acid amides, their use, and a process for their production |
| US5756548A (en) * | 1995-04-03 | 1998-05-26 | Centaur Pharmaceuticals, Inc. | Acetamidobenzamide compounds for neurodegenerative disorders |
| US5955506A (en) * | 1996-04-03 | 1999-09-21 | Centaur Pharmaceuticals, Inc. | Benzamides for neurodegenerative disorder treatment |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808624A (en) * | 1984-06-28 | 1989-02-28 | Bristol-Myers Company | Pharmacologically active substituted benzamides |
| US5011992A (en) * | 1984-06-28 | 1991-04-30 | Bristol-Myers Squibb Company | Pharmacologically active substituted benzamides |
-
1963
- 1963-11-15 GB GB45248/63A patent/GB1047028A/en not_active Expired
-
1964
- 1964-11-12 BR BR16424964A patent/BR6464249D0/en unknown
- 1964-11-13 FR FR1565309D patent/FR1565309A/fr not_active Expired
- 1964-11-13 FR FR994967A patent/FR3909M/fr not_active Expired
- 1964-11-13 BE BE655710D patent/BE655710A/xx unknown
- 1964-11-16 DE DE19641518287 patent/DE1518287A1/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795832A (en) * | 1986-10-02 | 1989-01-03 | Henkel Kommanditgesellschaft Auf Aktien | Salicylic acid amides, their use, and a process for their production |
| US5756548A (en) * | 1995-04-03 | 1998-05-26 | Centaur Pharmaceuticals, Inc. | Acetamidobenzamide compounds for neurodegenerative disorders |
| US5955506A (en) * | 1996-04-03 | 1999-09-21 | Centaur Pharmaceuticals, Inc. | Benzamides for neurodegenerative disorder treatment |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6464249D0 (en) | 1973-08-14 |
| BE655710A (en) | 1965-05-13 |
| DE1518287A1 (en) | 1969-05-22 |
| FR3909M (en) | 1966-02-07 |
| FR1565309A (en) | 1969-05-02 |
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