NO135092B - - Google Patents
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- Publication number
- NO135092B NO135092B NO2498/73A NO249873A NO135092B NO 135092 B NO135092 B NO 135092B NO 2498/73 A NO2498/73 A NO 2498/73A NO 249873 A NO249873 A NO 249873A NO 135092 B NO135092 B NO 135092B
- Authority
- NO
- Norway
- Prior art keywords
- methoxy
- chlorobenzamide
- amino
- acetamino
- diethylaminoethyl
- Prior art date
Links
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- JSEDLCVFUWNXNN-UHFFFAOYSA-N 4-amino-5-chloro-N-(2-chloroethyl)-2-methoxybenzamide Chemical compound ClCCNC(C1=C(C=C(C(=C1)Cl)N)OC)=O JSEDLCVFUWNXNN-UHFFFAOYSA-N 0.000 claims description 5
- OLAZDFVYXPEWKE-UHFFFAOYSA-N 4-acetamido-5-chloro-N-(2-hydroxyethyl)-2-methoxybenzamide Chemical compound OCCNC(C1=C(C=C(C(=C1)Cl)NC(C)=O)OC)=O OLAZDFVYXPEWKE-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- GOXCIWMHHSVOKW-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(O)=O GOXCIWMHHSVOKW-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OUEXNQRVYGYGIK-UHFFFAOYSA-N methyl 4-acetamido-5-chloro-2-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(NC(C)=O)C=C1OC OUEXNQRVYGYGIK-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HKTFLJLBAIJMAP-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(N)=O HKTFLJLBAIJMAP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Otolaryngology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7222288A FR2277815A1 (fr) | 1972-06-20 | 1972-06-20 | Nouveau procede de preparation du n(diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135092B true NO135092B (xx) | 1976-11-01 |
| NO135092C NO135092C (xx) | 1977-02-09 |
Family
ID=9100526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2498/73A NO135092C (xx) | 1972-06-20 | 1973-06-15 |
Country Status (26)
| Country | Link |
|---|---|
| JP (3) | JPS5522468B2 (xx) |
| KR (1) | KR780000231B1 (xx) |
| AT (1) | AT350044B (xx) |
| AU (1) | AU468921B2 (xx) |
| BE (1) | BE801038A (xx) |
| BG (3) | BG20570A3 (xx) |
| CA (1) | CA1001170A (xx) |
| CH (1) | CH568277A5 (xx) |
| CS (1) | CS167389B2 (xx) |
| DD (1) | DD107441A5 (xx) |
| DE (1) | DE2330373A1 (xx) |
| DK (1) | DK131030B (xx) |
| ES (1) | ES415952A1 (xx) |
| FI (1) | FI56677C (xx) |
| FR (1) | FR2277815A1 (xx) |
| GB (1) | GB1395131A (xx) |
| HU (1) | HU166936B (xx) |
| IE (1) | IE37800B1 (xx) |
| IL (1) | IL42499A (xx) |
| LU (1) | LU67805A1 (xx) |
| MC (1) | MC1007A1 (xx) |
| NO (1) | NO135092C (xx) |
| RO (1) | RO64465A (xx) |
| SE (5) | SE402452B (xx) |
| YU (1) | YU36691B (xx) |
| ZA (1) | ZA734127B (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5881689U (ja) * | 1981-11-25 | 1983-06-02 | 富士電機冷機株式会社 | カツプ式自動販売機 |
| JPS59155682U (ja) * | 1983-04-05 | 1984-10-19 | 東芝機器株式会社 | 飲料液自動販売機 |
| US4808624A (en) * | 1984-06-28 | 1989-02-28 | Bristol-Myers Company | Pharmacologically active substituted benzamides |
| JPH02148390A (ja) * | 1988-11-30 | 1990-06-07 | Fuji Electric Co Ltd | ホット商品自動販売機 |
| US10539725B2 (en) | 2016-11-30 | 2020-01-21 | Samsung Electronics Co., Ltd. | Optical filter and camera module and electronic device |
| CN113698321B (zh) * | 2021-09-30 | 2023-04-18 | 内蒙古康普药业有限公司 | 一种甲氧氯普胺双胺新杂质和用途 |
-
1972
- 1972-06-20 FR FR7222288A patent/FR2277815A1/fr active Granted
-
1973
- 1973-06-13 GB GB2820373A patent/GB1395131A/en not_active Expired
- 1973-06-14 YU YU1607/73A patent/YU36691B/xx unknown
- 1973-06-14 IL IL42499A patent/IL42499A/en unknown
- 1973-06-14 DE DE2330373A patent/DE2330373A1/de active Pending
- 1973-06-15 AU AU56994/73A patent/AU468921B2/en not_active Expired
- 1973-06-15 IE IE986/73A patent/IE37800B1/xx unknown
- 1973-06-15 NO NO2498/73A patent/NO135092C/no unknown
- 1973-06-15 ES ES415952A patent/ES415952A1/es not_active Expired
- 1973-06-16 BG BG25555A patent/BG20570A3/xx unknown
- 1973-06-16 BG BG25556A patent/BG22074A3/xx unknown
- 1973-06-16 BG BG23895A patent/BG22073A3/xx unknown
- 1973-06-18 LU LU67805A patent/LU67805A1/xx unknown
- 1973-06-18 DD DD171627A patent/DD107441A5/xx unknown
- 1973-06-18 BE BE1005166A patent/BE801038A/xx not_active IP Right Cessation
- 1973-06-18 SE SE7308532A patent/SE402452B/xx unknown
- 1973-06-18 AT AT531673A patent/AT350044B/de not_active IP Right Cessation
- 1973-06-18 FI FI1953/73A patent/FI56677C/fi active
- 1973-06-19 HU HUSO1088A patent/HU166936B/hu unknown
- 1973-06-19 DK DK337673AA patent/DK131030B/da not_active IP Right Cessation
- 1973-06-19 JP JP6967773A patent/JPS5522468B2/ja not_active Expired
- 1973-06-19 CA CA174,384A patent/CA1001170A/fr not_active Expired
- 1973-06-19 CS CS4410A patent/CS167389B2/cs unknown
- 1973-06-19 ZA ZA734127A patent/ZA734127B/xx unknown
- 1973-06-20 RO RO7375188A patent/RO64465A/ro unknown
- 1973-06-20 KR KR7300971A patent/KR780000231B1/ko active
- 1973-06-20 CH CH898873A patent/CH568277A5/xx not_active IP Right Cessation
- 1973-09-20 JP JP10686173A patent/JPS553341B2/ja not_active Expired
- 1973-09-20 JP JP10686073A patent/JPS553340B2/ja not_active Expired
-
1974
- 1974-06-08 MC MC1048A patent/MC1007A1/xx unknown
-
1976
- 1976-02-27 SE SE7602735A patent/SE421069B/xx not_active IP Right Cessation
- 1976-02-27 SE SE7602736A patent/SE421070B/xx not_active IP Right Cessation
- 1976-06-28 SE SE7607356A patent/SE7607356L/xx unknown
- 1976-06-28 SE SE7607357A patent/SE7607357L/xx unknown
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