GB1369259A - Acylxylidide local anaesthetics - Google Patents
Acylxylidide local anaestheticsInfo
- Publication number
- GB1369259A GB1369259A GB5937771A GB5937771A GB1369259A GB 1369259 A GB1369259 A GB 1369259A GB 5937771 A GB5937771 A GB 5937771A GB 5937771 A GB5937771 A GB 5937771A GB 1369259 A GB1369259 A GB 1369259A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- reacting
- pharmaceutically acceptable
- formula
- xylidine
- 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
- 229960005015 local anesthetics Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 abstract 1
- 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
- DROZQELYZZXYSX-UHFFFAOYSA-N 2-bromobutanoyl chloride Chemical compound CCC(Br)C(Cl)=O DROZQELYZZXYSX-UHFFFAOYSA-N 0.000 abstract 1
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229960001270 d- tartaric acid Drugs 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229940127557 pharmaceutical product Drugs 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
- C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1369259 Xylidine derivatives ASTRA PHARMACEUTICAL PRODUCTS Inc 21 Dec 1971 [22 Dec 1970 19 July 1971] 59377/71 Heading C2C Novel xylidine derivatives of the Formula I wherein R<SP>1</SP> is ethyl, propyl, or butyl; R<SP>2</SP> and R<SP>3</SP> each are methyl, ethyl, propyl or butyl or R<SP>2</SP> and R<SP>3</SP> together is tetramethylene; the total sum of carbon atoms in R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> being at least six; and pharmaceutically acceptable acid addition salts thereof are prepared by reacting the appropriate 2-alkyl-2-bromo-(or iodo)-2<SP>1</SP>,6<SP>1</SP>- acetoxylides with amines of the formula H-NR<SP>2</SP>R<SP>3</SP>, or with amines of the formula R<SP>2</SP>NH 2 , and reacting the thus obtained 2-alkyl- 2-alkylamino-2<SP>1</SP>,6<SP>1</SP>-acetozylidides, with alkylating agents. The racemic compounds thus obtained may be resolved by treatment with l- and d-tartaric acid. 2 - Alkyl - 2 - iodo - 2<SP>1</SP>,6<SP>1</SP>- acetoxylidides are obtained by reacting potassium iodide with the corresponding 2 - alkyl - 2 - bromo - 2<SP>1</SP>,6<SP>1</SP>- acetoxylidides, resulting from the reaction between the appropriate acid chloride and 2,6-xylidine. 2-Bromobutyryl chloride is obtained by reacting 2-bromobutyric acid with thionyl chloride. Pharmaceutical compositions, suitable for parenteral or topical administration, contain the above novel compounds or pharmaceutically acceptable acid addition salts thereof in association with pharmaceutically acceptable carriers. The compounds possess local anaesthetic activity.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10077770A | 1970-12-22 | 1970-12-22 | |
| US00164022A US3812147A (en) | 1970-12-22 | 1971-07-19 | Acylxylidide local anaesthetics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1369259A true GB1369259A (en) | 1974-10-23 |
Family
ID=26797539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5937771A Expired GB1369259A (en) | 1970-12-22 | 1971-12-21 | Acylxylidide local anaesthetics |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3812147A (en) |
| JP (1) | JPS5644063B1 (en) |
| AR (1) | AR193840A1 (en) |
| AT (1) | AT319205B (en) |
| AU (1) | AU468489B2 (en) |
| BE (1) | BE776656A (en) |
| BR (1) | BR7108466D0 (en) |
| CA (1) | CA943966A (en) |
| DD (1) | DD99779A5 (en) |
| DE (1) | DE2162744C3 (en) |
| DK (1) | DK139814B (en) |
| ES (2) | ES398210A1 (en) |
| FI (1) | FI55027C (en) |
| FR (1) | FR2118985B1 (en) |
| GB (1) | GB1369259A (en) |
| HU (1) | HU163373B (en) |
| IE (1) | IE35909B1 (en) |
| IT (1) | IT1066334B (en) |
| NL (2) | NL172149C (en) |
| NO (1) | NO135934C (en) |
| PL (1) | PL83097B1 (en) |
| SE (1) | SE393374B (en) |
| SU (1) | SU419023A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990009986A1 (en) * | 1989-02-28 | 1990-09-07 | Aktiebolaget Astra | New local anaesthetic compounds and a process for their preparation |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4237068A (en) * | 1971-07-28 | 1980-12-02 | Astra Pharmaceutical Products, Inc. | Primary aminoacylanilides |
| US3966934A (en) * | 1971-12-08 | 1976-06-29 | Astra Pharmaceutical Products, Inc. | Synergistic local anesthetic compositions |
| US3957996A (en) * | 1971-12-08 | 1976-05-18 | Astra Pharmaceutical Products, Inc. | Pharmaceutical local anesthetic compositions |
| US3975443A (en) * | 1972-06-06 | 1976-08-17 | Allen & Hanburys Limited | 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine |
| JPS598269B2 (en) * | 1975-08-22 | 1984-02-23 | 萬有製薬株式会社 | Omega - aminoalkanesane arylamide |
| JPS57176939A (en) * | 1981-04-03 | 1982-10-30 | Goodrich Co B F | Improved synthesis of hindered amine stabilizer for high polymer materials |
| US4891058A (en) * | 1988-07-18 | 1990-01-02 | Ici Americas Inc. | 1-alkyl-3-aryl imidazolidine-2,4-diones and herbicidal use |
| US5153226A (en) * | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
| AU2007322033B2 (en) | 2006-11-20 | 2013-07-11 | President And Fellows Of Harvard College | Methods, compositions, and kits for treating pain and pruritis |
| JP6205133B2 (en) | 2009-07-10 | 2017-09-27 | プレジデント アンド フェローズ オブ ハーバード カレッジ | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| AU2016301282B2 (en) | 2015-08-03 | 2022-03-17 | Children's Medical Center Corporation | Charged ion channel blockers and methods for use |
| US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| MA55307A (en) | 2019-03-11 | 2022-01-19 | Nocion Therapeutics Inc | CHARGED ION CHANNEL BLOCKERS AND METHODS OF USE |
| JP7692834B2 (en) | 2019-03-11 | 2025-06-16 | ノシオン セラピューティクス，インコーポレイテッド | Charged ion channel blockers and methods of use - Patents.com |
| KR102887727B1 (en) | 2019-03-11 | 2025-11-18 | 녹시온 테라퓨틱스 인코포레이티드 | Ester-substituted ion channel blockers and methods of use |
| US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| AU2020380118A1 (en) | 2019-11-06 | 2022-05-19 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| EP4118070A4 (en) | 2020-03-11 | 2024-04-10 | Nocion Therapeutics, Inc. | CHARGED ION CHANNEL BLOCKERS AND METHODS OF USE |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1124837A (en) * | 1966-06-03 | 1968-08-21 | Wyeth John & Brother Ltd | Substituted anilides |
-
1971
- 1971-07-19 US US00164022A patent/US3812147A/en not_active Expired - Lifetime
- 1971-12-07 SE SE7115656A patent/SE393374B/en unknown
- 1971-12-14 BE BE776656A patent/BE776656A/en not_active IP Right Cessation
- 1971-12-15 SU SU1726195A patent/SU419023A3/en active
- 1971-12-16 HU HUAA690A patent/HU163373B/hu unknown
- 1971-12-17 DK DK619771AA patent/DK139814B/en not_active IP Right Cessation
- 1971-12-17 NO NO4669/71A patent/NO135934C/no unknown
- 1971-12-17 DE DE2162744A patent/DE2162744C3/en not_active Expired
- 1971-12-18 IT IT54845/71A patent/IT1066334B/en active
- 1971-12-20 AT AT1089671A patent/AT319205B/en not_active IP Right Cessation
- 1971-12-20 AU AU37099/71A patent/AU468489B2/en not_active Expired
- 1971-12-20 IE IE1609/71A patent/IE35909B1/en unknown
- 1971-12-21 CA CA130,662A patent/CA943966A/en not_active Expired
- 1971-12-21 BR BR8466/71A patent/BR7108466D0/en unknown
- 1971-12-21 DD DD159785A patent/DD99779A5/xx unknown
- 1971-12-21 ES ES398210A patent/ES398210A1/en not_active Expired
- 1971-12-21 AR AR239721A patent/AR193840A1/en active
- 1971-12-21 GB GB5937771A patent/GB1369259A/en not_active Expired
- 1971-12-21 PL PL1971152331A patent/PL83097B1/pl unknown
- 1971-12-21 FR FR7145983A patent/FR2118985B1/fr not_active Expired
- 1971-12-22 FI FI3658/71A patent/FI55027C/en active
- 1971-12-22 NL NLAANVRAGE7117644,A patent/NL172149C/en not_active IP Right Cessation
- 1971-12-22 JP JP10453571A patent/JPS5644063B1/ja active Pending
-
1974
- 1974-04-24 ES ES425626A patent/ES425626A1/en not_active Expired
-
1982
- 1982-10-26 NL NL8204126A patent/NL8204126A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990009986A1 (en) * | 1989-02-28 | 1990-09-07 | Aktiebolaget Astra | New local anaesthetic compounds and a process for their preparation |
| GR900100108A (en) * | 1989-02-28 | 1991-06-28 | Astra Ab | New local anaesthetic compounds and a process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| SE393374B (en) | 1977-05-09 |
| DK139814C (en) | 1979-10-01 |
| IT1066334B (en) | 1985-03-04 |
| NL172149C (en) | 1983-07-18 |
| FR2118985B1 (en) | 1975-12-26 |
| SU419023A3 (en) | 1974-03-05 |
| AR193840A1 (en) | 1973-05-31 |
| NO135934C (en) | 1977-06-29 |
| ES425626A1 (en) | 1976-06-16 |
| FR2118985A1 (en) | 1972-08-04 |
| NL172149B (en) | 1983-02-16 |
| NL7117644A (en) | 1972-06-26 |
| DD99779A5 (en) | 1973-08-20 |
| IE35909L (en) | 1972-06-22 |
| AU3709971A (en) | 1973-06-28 |
| NL8204126A (en) | 1983-02-01 |
| DK139814B (en) | 1979-04-23 |
| AT319205B (en) | 1974-12-10 |
| IE35909B1 (en) | 1976-06-23 |
| HU163373B (en) | 1973-08-28 |
| DE2162744A1 (en) | 1972-07-06 |
| BE776656A (en) | 1972-06-14 |
| DE2162744B2 (en) | 1981-07-02 |
| BR7108466D0 (en) | 1973-06-14 |
| CA943966A (en) | 1974-03-19 |
| ES398210A1 (en) | 1975-03-16 |
| AU468489B2 (en) | 1976-01-15 |
| JPS5644063B1 (en) | 1981-10-16 |
| NO135934B (en) | 1977-03-21 |
| PL83097B1 (en) | 1975-12-31 |
| FI55027B (en) | 1979-01-31 |
| DE2162744C3 (en) | 1982-04-15 |
| FI55027C (en) | 1979-05-10 |
| US3812147A (en) | 1974-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |