IL30976A - Transformed benzamides and the process for their production - Google Patents
Transformed benzamides and the process for their productionInfo
- Publication number
- IL30976A IL30976A IL30976A IL3097665A IL30976A IL 30976 A IL30976 A IL 30976A IL 30976 A IL30976 A IL 30976A IL 3097665 A IL3097665 A IL 3097665A IL 30976 A IL30976 A IL 30976A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- added
- chloride
- stirred
- manufacture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 3
- 150000003936 benzamides Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 benzoyl halide Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
- 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 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BJMZHGBTBCQLNN-UHFFFAOYSA-N 2-propoxybenzoyl chloride Chemical compound CCCOC1=CC=CC=C1C(Cl)=O BJMZHGBTBCQLNN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
-
- 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
- C07C233/16—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 singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36583864A | 1964-05-07 | 1964-05-07 | |
| US389516A US3362993A (en) | 1964-05-07 | 1964-08-10 | Substituted benzamides and methods for their preparation |
| US682661A US3407234A (en) | 1964-05-07 | 1967-11-13 | 4-(2-benzylalkylaminoalkoxy)-benzylamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL30976A true IL30976A (en) | 1969-01-29 |
Family
ID=27408721
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL30976A IL30976A (en) | 1964-05-07 | 1965-04-19 | Transformed benzamides and the process for their production |
| IL23384A IL23384A (en) | 1964-05-07 | 1965-04-19 | Substituted benzamides and process for the manufacture thereof |
| IL30977A IL30977A (en) | 1964-05-07 | 1965-04-19 | Substituted aminoalkoxybenzenes and process for the manufacture thereof |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL23384A IL23384A (en) | 1964-05-07 | 1965-04-19 | Substituted benzamides and process for the manufacture thereof |
| IL30977A IL30977A (en) | 1964-05-07 | 1965-04-19 | Substituted aminoalkoxybenzenes and process for the manufacture thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US3362993A (da) |
| BE (1) | BE663456A (da) |
| BR (1) | BR6569369D0 (da) |
| CH (1) | CH461530A (da) |
| CY (1) | CY442A (da) |
| DE (1) | DE1493828A1 (da) |
| DK (2) | DK115395B (da) |
| FR (2) | FR1437793A (da) |
| GB (1) | GB1032880A (da) |
| IL (3) | IL30976A (da) |
| MY (1) | MY6900036A (da) |
| NL (2) | NL6505819A (da) |
| SE (1) | SE330688B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130752C (da) * | 1964-05-07 | |||
| YU46706B (sh) * | 1987-09-05 | 1994-04-05 | Hokuriku Pharmaceutical Co. Ltd. | Postupak za dobijanje amidnih jedinjenja |
| US20090177008A1 (en) * | 2005-12-28 | 2009-07-09 | Cadila Pharmaceuticals Ltd. | Novel process for synthesis of itopride and its novel intermediate n-(4-hydroxybenzyl)- 3,4-dimethoxybenzamide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1894375A (en) * | 1933-01-17 | Basic product and process of making it | ||
| US2906777A (en) * | 1955-07-08 | 1959-09-29 | Geigy Chem Corp | N-acylated hydroxybenzylamino phenols |
| DE1079622B (de) * | 1956-12-07 | 1960-04-14 | Thomae Gmbh Dr K | Verfahren zur Herstellung von antipyretisch und antiphlogistisch wirksamen, ungesaettigten 2-Acyl-4-amino-phenolaethern |
| US2879293A (en) * | 1957-02-19 | 1959-03-24 | Hoffmann La Roche | Benzylamine derivatives |
| US3139456A (en) * | 1960-07-27 | 1964-06-30 | Searle & Co | Nu-(substituted phenoxyalkyl)-aralkylamines |
| NL130752C (da) * | 1964-05-07 |
-
0
- NL NL130752D patent/NL130752C/xx active
-
1964
- 1964-08-10 US US389516A patent/US3362993A/en not_active Expired - Lifetime
-
1965
- 1965-04-14 CH CH89368A patent/CH461530A/de unknown
- 1965-04-19 IL IL30976A patent/IL30976A/en unknown
- 1965-04-19 IL IL23384A patent/IL23384A/en unknown
- 1965-04-19 IL IL30977A patent/IL30977A/xx unknown
- 1965-04-22 DE DE19651493828 patent/DE1493828A1/de active Pending
- 1965-05-04 BR BR169369/65A patent/BR6569369D0/pt unknown
- 1965-05-05 GB GB18917/65A patent/GB1032880A/en not_active Expired
- 1965-05-05 FR FR15799A patent/FR1437793A/fr not_active Expired
- 1965-05-05 FR FR15800A patent/FR4507M/fr not_active Expired
- 1965-05-05 BE BE663456D patent/BE663456A/xx unknown
- 1965-05-07 DK DK234065AA patent/DK115395B/da unknown
- 1965-05-07 NL NL6505819A patent/NL6505819A/xx unknown
- 1965-05-07 SE SE05999/65A patent/SE330688B/xx unknown
-
1966
- 1966-03-11 DK DK127966AA patent/DK112952B/da unknown
-
1967
- 1967-11-13 US US682661A patent/US3407234A/en not_active Expired - Lifetime
-
1968
- 1968-06-18 CY CY44268A patent/CY442A/xx unknown
-
1969
- 1969-12-31 MY MY196936A patent/MY6900036A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1437793A (fr) | 1966-05-06 |
| DK112952B (da) | 1969-02-03 |
| US3362993A (en) | 1968-01-09 |
| IL30977A (en) | 1969-01-29 |
| NL6505819A (da) | 1965-11-08 |
| DK115395B (da) | 1969-10-06 |
| GB1032880A (en) | 1966-06-15 |
| IL23384A (en) | 1969-01-29 |
| BE663456A (da) | 1965-11-05 |
| DE1493828A1 (de) | 1969-02-27 |
| CY442A (en) | 1968-06-18 |
| BR6569369D0 (pt) | 1973-08-02 |
| MY6900036A (en) | 1969-12-31 |
| CH461530A (de) | 1968-08-31 |
| FR4507M (da) | 1966-10-17 |
| US3407234A (en) | 1968-10-22 |
| NL130752C (da) | |
| SE330688B (da) | 1970-11-30 |
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