GB1165300A - Substituted Anthranilic Acid Amides - Google Patents
Substituted Anthranilic Acid AmidesInfo
- Publication number
- GB1165300A GB1165300A GB3033568A GB3033568A GB1165300A GB 1165300 A GB1165300 A GB 1165300A GB 3033568 A GB3033568 A GB 3033568A GB 3033568 A GB3033568 A GB 3033568A GB 1165300 A GB1165300 A GB 1165300A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- substituted
- reacting
- anthronilic
- methyl
- 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
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 7
- -1 N-substituted anthranilic acid amides Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 abstract 2
- OPDUMRSBESYOCQ-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-3,1-benzoxazine-2,4-dione Chemical compound CC1=CC=CC(N2C(OC(=O)C3=CC=CC=C32)=O)=C1C OPDUMRSBESYOCQ-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical class NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
1,165,300. N-substituted anthranilic acid amides. GEA A.S. 25 June, 1968 [3 July, 1967], No. 30335/68. Heading C2C. Novel N-substituted anthranilic acid amides of the formula wherein R<SP>1</SP> is H or C 1-5 alkyl, R<SP>2</SP> is a straight or branched C 2-5 alkylene, R<SP>3</SP> and R<SP>4</SP>, which may be the same or different, are each methyl or ethyl, and R<SP>5</SP> and R<SP>6</SP> are H, C 1-5 alkyl, halogen or trihalomethyl, with the proviso that at least one of R<SP>5</SP> and R<SP>6</SP> is other than hydrogen and the 4-position of this benzene ring is unsubstituted, and acid addition salts thereof, are prepared by reacting the appropriately N- substituted benzamide, which is also substituted in the 2-position by an halogen atom or reactive ester group with the corresponding substituted aminobenzene in an organic solvent and the presence of an acid binding agent, or by reacting a mixed acid anhydride of the appropriately N- substituted anthronilic acid with a monoalkyl ester of carbonic acid with an amine of the formula R<SP>3</SP>(R<SP>4</SP>)NR<SP>2</SP>NHR<SP>1</SP>, or by reacting an N-substituted isatoicanhydride of the formula with a diamine of the formula R<SP>3</SP>(R<SP>4</SP>)NR<SP>2</SP>NHR<SP>1</SP>. N-(2,3- xylyl)-isatoicanhydride and N-(3- methylphenyl) - isotoicanhydride are prepared by reacting phosgene with N-C 2,3 -xylyl)- anthranilic acid and N-(3-methyl-phenyl)- anthronilic acid respectively. The mixed anhydride of N-(2-methyl-3-chlorophenyl)-anthronilic acid and monoethyl carbonate is obtained by reacting N-(2-methyl-3-chlorophenyl)-anthronilic acid with ethyl chloroformate. N - (4 - chlorophenyl) - anthronilicz acid - (2-dimethylamino-propyl)-amide is prepared by one of the above methods outlined for the novel compounds. Pharmaceutical compositions, suitable for oral or parenteral administration, and having analgesic activity contain the above novel anthronilic acid amide derivatives as the active ingredient and a suitable carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK342267A DK121236B (en) | 1967-07-03 | 1967-07-03 | Analogous process for the preparation of therapeutically active, basic substituted amides of N-substituted anthranilic acids, or acid addition salts thereof. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1165300A true GB1165300A (en) | 1969-09-24 |
Family
ID=8122684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3033568A Expired GB1165300A (en) | 1967-07-03 | 1968-06-25 | Substituted Anthranilic Acid Amides |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE717543A (en) |
| BR (1) | BR6800332D0 (en) |
| CA (1) | CA921051A (en) |
| CH (1) | CH512436A (en) |
| DK (1) | DK121236B (en) |
| ES (1) | ES355674A1 (en) |
| FI (1) | FI49024C (en) |
| FR (1) | FR1584334A (en) |
| GB (1) | GB1165300A (en) |
| IE (1) | IE32158B1 (en) |
| NL (1) | NL163503C (en) |
| NO (1) | NO121213B (en) |
| SE (1) | SE363504B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008029199A1 (en) * | 2006-09-03 | 2008-03-13 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of n-arylanthranilic acids with very fast skin penetration rate |
| WO2008149181A1 (en) * | 2007-06-04 | 2008-12-11 | Techfields Inc | Pro-drugs of nsaias with very high skin and membranes penetration rates and their new medicinal uses |
| JP2015120703A (en) * | 2015-01-05 | 2015-07-02 | テックフィールズ インコーポレイテッド | NSAIA prodrug with very fast skin and membrane permeation rate and novel pharmaceutical use thereof |
| US9872846B2 (en) | 2006-07-09 | 2018-01-23 | Techfields Pharma Co., Ltd. | High penetration compositions and uses thereof |
| US11135153B2 (en) | 2006-07-09 | 2021-10-05 | Techfields Pharma Co., Ltd. | High penetration composition and uses thereof |
| US11541029B2 (en) | 2008-12-04 | 2023-01-03 | Techfields Pharma Co., Ltd. | High penetration compositions and their applications |
| US11813256B2 (en) | 2012-01-18 | 2023-11-14 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions and pharmaceutical compositon thereof for treatment of pulmonary conditions |
-
1967
- 1967-07-03 DK DK342267A patent/DK121236B/en not_active IP Right Cessation
-
1968
- 1968-06-24 IE IE74768A patent/IE32158B1/en unknown
- 1968-06-25 GB GB3033568A patent/GB1165300A/en not_active Expired
- 1968-07-02 NO NO265268A patent/NO121213B/no unknown
- 1968-07-02 CH CH989768A patent/CH512436A/en not_active IP Right Cessation
- 1968-07-02 BR BR20033268A patent/BR6800332D0/en unknown
- 1968-07-02 NL NL6809321A patent/NL163503C/en active
- 1968-07-02 FR FR1584334D patent/FR1584334A/fr not_active Expired
- 1968-07-02 ES ES355674A patent/ES355674A1/en not_active Expired
- 1968-07-03 FI FI191768A patent/FI49024C/en active
- 1968-07-03 SE SE918268A patent/SE363504B/xx unknown
- 1968-07-03 BE BE717543D patent/BE717543A/xx unknown
- 1968-07-03 CA CA024135A patent/CA921051A/en not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11135153B2 (en) | 2006-07-09 | 2021-10-05 | Techfields Pharma Co., Ltd. | High penetration composition and uses thereof |
| US9872846B2 (en) | 2006-07-09 | 2018-01-23 | Techfields Pharma Co., Ltd. | High penetration compositions and uses thereof |
| WO2008029199A1 (en) * | 2006-09-03 | 2008-03-13 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of n-arylanthranilic acids with very fast skin penetration rate |
| EP2623495A1 (en) * | 2006-09-03 | 2013-08-07 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of n-arylanthranilic acids with very fast skin penetration rate |
| US9371284B2 (en) | 2007-06-04 | 2016-06-21 | Techfields Pharma Co., Ltd. | Pro-drugs of NSAIAS with very high skin and membranes penetration rates and their new medicinal uses |
| AU2007354632B2 (en) * | 2007-06-04 | 2014-06-26 | Techfields Inc | Pro-drugs of NSAIAs with very high skin and membranes penetration rates and their new medicinal uses |
| RU2509076C2 (en) * | 2007-06-04 | 2014-03-10 | Текфилдз Инк | Prodrugs of nonsteroid anti-inflammatory agents (nsaia) with very high speed of penetration through skin and membranes, and new medical applications of above said prodrugs |
| AU2016228230B2 (en) * | 2007-06-04 | 2018-04-05 | Techfields Inc | Pro-drugs of NSAIAS with very high skin and membranes penetration rates and their new medicinal uses |
| AU2016228230C1 (en) * | 2007-06-04 | 2018-08-30 | Techfields Inc | Pro-drugs of NSAIAS with very high skin and membranes penetration rates and their new medicinal uses |
| US10233198B2 (en) | 2007-06-04 | 2019-03-19 | Techfields Pharma Co., Ltd. | Pro-drugs of NSAIAs with very high skin and membranes penetration rates and their new medicinal uses |
| WO2008149181A1 (en) * | 2007-06-04 | 2008-12-11 | Techfields Inc | Pro-drugs of nsaias with very high skin and membranes penetration rates and their new medicinal uses |
| US11541029B2 (en) | 2008-12-04 | 2023-01-03 | Techfields Pharma Co., Ltd. | High penetration compositions and their applications |
| US11813256B2 (en) | 2012-01-18 | 2023-11-14 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions and pharmaceutical compositon thereof for treatment of pulmonary conditions |
| US11857545B2 (en) | 2012-01-18 | 2024-01-02 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions and pharmaceutical composition thereof for treatment of pulmonary conditions |
| JP2015120703A (en) * | 2015-01-05 | 2015-07-02 | テックフィールズ インコーポレイテッド | NSAIA prodrug with very fast skin and membrane permeation rate and novel pharmaceutical use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| SE363504B (en) | 1974-01-21 |
| FI49024C (en) | 1975-03-10 |
| NL163503C (en) | 1980-09-15 |
| CA921051A (en) | 1973-02-13 |
| BR6800332D0 (en) | 1973-02-13 |
| FI49024B (en) | 1974-12-02 |
| CH512436A (en) | 1971-09-15 |
| DK121236B (en) | 1971-09-27 |
| DE1768818A1 (en) | 1971-12-30 |
| IE32158L (en) | 1969-01-03 |
| NO121213B (en) | 1971-02-01 |
| IE32158B1 (en) | 1973-05-02 |
| ES355674A1 (en) | 1970-01-01 |
| FR1584334A (en) | 1969-12-19 |
| BE717543A (en) | 1968-12-16 |
| NL6809321A (en) | 1969-01-07 |
| DE1768818B2 (en) | 1977-05-05 |
| NL163503B (en) | 1980-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |