GB895495A - Amino-acetamidoximes and their preparation - Google Patents
Amino-acetamidoximes and their preparationInfo
- Publication number
- GB895495A GB895495A GB210360A GB210360A GB895495A GB 895495 A GB895495 A GB 895495A GB 210360 A GB210360 A GB 210360A GB 210360 A GB210360 A GB 210360A GB 895495 A GB895495 A GB 895495A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- acid addition
- aryl
- compound
- benzyl
- 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
- 238000002360 preparation method Methods 0.000 title abstract 3
- TZWFTFOOLZXSGS-UHFFFAOYSA-N 2-amino-n'-hydroxyethanimidamide Chemical class NCC(N)=NO TZWFTFOOLZXSGS-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- -1 aralkyl radical Chemical class 0.000 abstract 3
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- YADQFVSGJBBHDV-UHFFFAOYSA-N N-benzyl-N'-phenylethanethiohydrazide Chemical compound C(C1=CC=CC=C1)N(C(C)=S)NC1=CC=CC=C1 YADQFVSGJBBHDV-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 229940125715 antihistaminic agent Drugs 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229940105847 calamine Drugs 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 abstract 1
- 229960004926 chlorobutanol Drugs 0.000 abstract 1
- 229960002242 chlorocresol Drugs 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229910052864 hemimorphite Inorganic materials 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 229940041616 menthol Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000007922 nasal spray Substances 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 abstract 1
- 229960001802 phenylephrine Drugs 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- 235000014692 zinc oxide Nutrition 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of general formula <FORM:0895495/IV (b)/1> wherein R1 represents an aralkyl radical and R2 represents an aryl or p-substituted aryl radical, and their acid addition and hydrated acid addition salts: also process for their preparation, either (1) reacting hydroxylamine or a salt thereof with a compound of general formula <FORM:0895495/IV (b)/2> wherein R1 R2 are as above and R3 represents <FORM:0895495/IV (b)/3> wherein R4 represents an alkyl radical of 1-4 carbon atoms and X represents oxygen or sulphur, optionally with an acid binding agent, or (2) reacting a compound R1Y wherein R1 is as above and Y represents chlorine, bromine or iodine, with an acid addition salt of a compound of general formula <FORM:0895495/IV (b)/4> wherein R2 is as above. N-benzyl-N-phenylamino-thioacetamide is prepared by the action of H2S on the corresponding acetonitrile. N-p-Methoxyphenyl- and N-p-tolyl-N-benzyl-aminoacetonitriles are prepared by the action of benzyl chloride on the corresponding N-mono-substituted compounds. Specification 699,644 is referred to.ALSO:Pharmaceutical compositions comprise, in association with a pharmaceutically acceptable diluent or carrier, amino-acetamidoximes of general formula <FORM:0895495/VI/1> (wherein R1 is aralkyl, and R2 is aryl or p-subst ituted aryl) or their acid addition salts, which compounds are antihistaminics. Oral (tablets, capsules, elixirs), parenteral (solutions, which may contain bacteriostats), and topical (creams, ointments, nasal sprays and lotions) administration is mentioned. Preparations with other active agents e.g. naphajoline, phenylephrine, pholsidine, chlorbutol, chlorocresol, calamine and menthol are described. Specification 699,644 is referred to.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB210360A GB895495A (en) | 1960-01-20 | 1960-01-20 | Amino-acetamidoximes and their preparation |
| BE599008A BE599008A (en) | 1960-01-20 | 1961-01-11 | New derivatives of hydroxylamine, their preparation and compositions containing them. |
| MY6300022A MY6300022A (en) | 1960-01-20 | 1963-12-31 | Amino-acetamidoximes and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB210360A GB895495A (en) | 1960-01-20 | 1960-01-20 | Amino-acetamidoximes and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB895495A true GB895495A (en) | 1962-05-02 |
Family
ID=9733669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB210360A Expired GB895495A (en) | 1960-01-20 | 1960-01-20 | Amino-acetamidoximes and their preparation |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE599008A (en) |
| GB (1) | GB895495A (en) |
| MY (1) | MY6300022A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10022339B2 (en) | 2006-04-21 | 2018-07-17 | The Procter & Gamble Company | Compositions and methods useful for treatment of respiratory illness |
| US10098873B2 (en) | 2006-04-21 | 2018-10-16 | The Procter & Gamble Company | Compositions and kits useful for treatment of respiratory illness |
-
1960
- 1960-01-20 GB GB210360A patent/GB895495A/en not_active Expired
-
1961
- 1961-01-11 BE BE599008A patent/BE599008A/en unknown
-
1963
- 1963-12-31 MY MY6300022A patent/MY6300022A/en unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10022339B2 (en) | 2006-04-21 | 2018-07-17 | The Procter & Gamble Company | Compositions and methods useful for treatment of respiratory illness |
| US10098873B2 (en) | 2006-04-21 | 2018-10-16 | The Procter & Gamble Company | Compositions and kits useful for treatment of respiratory illness |
| US10688089B2 (en) | 2006-04-21 | 2020-06-23 | The Procter & Gamble Company | Compositions and kits useful for treatment of respiratory illness |
| US10772848B2 (en) | 2006-04-21 | 2020-09-15 | The Procter & Gamble Company | Compositions and methods useful for treatment of respiratory illness |
| US11077074B2 (en) | 2006-04-21 | 2021-08-03 | The Procter & Gamble Company | Compositions and methods useful for treatment of respiratory illness |
| US11083697B2 (en) | 2006-04-21 | 2021-08-10 | The Procter & Gamble Company | Compositions and methods useful for treatment of respiratory illness |
| US11141415B2 (en) | 2006-04-21 | 2021-10-12 | The Procter & Gamble Company | Compositions and kits useful for treatment of respiratory illness |
| US11491151B2 (en) | 2006-04-21 | 2022-11-08 | The Procter & Gamble Company | Compositions and kits useful for treatment of respiratory illness |
| US12083117B2 (en) | 2006-04-21 | 2024-09-10 | The Procter & Gamble Company | Compositions and kits useful for treatment of respiratory illness |
| US12403103B2 (en) | 2006-04-21 | 2025-09-02 | The Procter & Gamble Company | Compositions and methods useful for treatment of respiratory illness |
Also Published As
| Publication number | Publication date |
|---|---|
| MY6300022A (en) | 1963-12-31 |
| BE599008A (en) | 1961-07-11 |
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