FI56677C - Nytt foerfarande foer framstaellning av n-(dietylaminoetyl)-2-metoxi-4-amino-5-klorbensamid och dess farmaceutiskt godtagbara syraadditionssalter samt kvaternaera ammoniumsalter - Google Patents
Nytt foerfarande foer framstaellning av n-(dietylaminoetyl)-2-metoxi-4-amino-5-klorbensamid och dess farmaceutiskt godtagbara syraadditionssalter samt kvaternaera ammoniumsalter Download PDFInfo
- Publication number
- FI56677C FI56677C FI1953/73A FI195373A FI56677C FI 56677 C FI56677 C FI 56677C FI 1953/73 A FI1953/73 A FI 1953/73A FI 195373 A FI195373 A FI 195373A FI 56677 C FI56677 C FI 56677C
- Authority
- FI
- Finland
- Prior art keywords
- methoxy
- amino
- chlorobenzamide
- syraad
- ditionssalter
- Prior art date
Links
- 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 title 1
- 229910052708 sodium Inorganic materials 0.000 title 1
- 239000011734 sodium Substances 0.000 title 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 10
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- -1 2-methoxy-4-acetylimino-5-chlorobenzoic acid ester Chemical class 0.000 claims description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- MJTGQALMWUUPQM-UHFFFAOYSA-N m-Chlorobenzamide Chemical compound NC(=O)C1=CC=CC(Cl)=C1 MJTGQALMWUUPQM-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 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 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 229940031098 ethanolamine Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 description 3
- 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
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 2
- ZKSYUNLBFSOENV-UHFFFAOYSA-N n-(2-hydroxyethyl)benzamide Chemical compound OCCNC(=O)C1=CC=CC=C1 ZKSYUNLBFSOENV-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000003054 catalyst Substances 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
- 239000000543 intermediate Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- FYQJUYCGPLFWQR-UHFFFAOYSA-N n-(2-chloroethyl)benzamide Chemical compound ClCCNC(=O)C1=CC=CC=C1 FYQJUYCGPLFWQR-UHFFFAOYSA-N 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Otolaryngology (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7222288 | 1972-06-20 | ||
| 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 |
|---|---|
| FI56677B FI56677B (fi) | 1979-11-30 |
| FI56677C true FI56677C (fi) | 1980-03-10 |
Family
ID=9100526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1953/73A FI56677C (fi) | 1972-06-20 | 1973-06-18 | Nytt foerfarande foer framstaellning av n-(dietylaminoetyl)-2-metoxi-4-amino-5-klorbensamid och dess farmaceutiskt godtagbara syraadditionssalter samt kvaternaera ammoniumsalter |
Country Status (26)
| Country | Link |
|---|---|
| JP (3) | JPS5522468B2 (en, 2012) |
| KR (1) | KR780000231B1 (en, 2012) |
| AT (1) | AT350044B (en, 2012) |
| AU (1) | AU468921B2 (en, 2012) |
| BE (1) | BE801038A (en, 2012) |
| BG (3) | BG20570A3 (en, 2012) |
| CA (1) | CA1001170A (en, 2012) |
| CH (1) | CH568277A5 (en, 2012) |
| CS (1) | CS167389B2 (en, 2012) |
| DD (1) | DD107441A5 (en, 2012) |
| DE (1) | DE2330373A1 (en, 2012) |
| DK (1) | DK131030B (en, 2012) |
| ES (1) | ES415952A1 (en, 2012) |
| FI (1) | FI56677C (en, 2012) |
| FR (1) | FR2277815A1 (en, 2012) |
| GB (1) | GB1395131A (en, 2012) |
| HU (1) | HU166936B (en, 2012) |
| IE (1) | IE37800B1 (en, 2012) |
| IL (1) | IL42499A (en, 2012) |
| LU (1) | LU67805A1 (en, 2012) |
| MC (1) | MC1007A1 (en, 2012) |
| NO (1) | NO135092C (en, 2012) |
| RO (1) | RO64465A (en, 2012) |
| SE (5) | SE402452B (en, 2012) |
| YU (1) | YU36691B (en, 2012) |
| ZA (1) | ZA734127B (en, 2012) |
Families Citing this family (5)
| 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 |
| 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 DE DE2330373A patent/DE2330373A1/de active Pending
- 1973-06-14 YU YU1607/73A patent/YU36691B/xx unknown
- 1973-06-14 IL IL42499A patent/IL42499A/en unknown
- 1973-06-15 ES ES415952A patent/ES415952A1/es not_active Expired
- 1973-06-15 NO NO2498/73A patent/NO135092C/no unknown
- 1973-06-15 AU AU56994/73A patent/AU468921B2/en not_active Expired
- 1973-06-15 IE IE986/73A patent/IE37800B1/xx unknown
- 1973-06-16 BG BG025555A 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 BE BE1005166A patent/BE801038A/xx not_active IP Right Cessation
- 1973-06-18 FI FI1953/73A patent/FI56677C/fi active
- 1973-06-18 LU LU67805A patent/LU67805A1/xx unknown
- 1973-06-18 DD DD171627A patent/DD107441A5/xx unknown
- 1973-06-18 AT AT531673A patent/AT350044B/de not_active IP Right Cessation
- 1973-06-18 SE SE7308532A patent/SE402452B/xx unknown
- 1973-06-19 JP JP6967773A patent/JPS5522468B2/ja not_active Expired
- 1973-06-19 CS CS4410A patent/CS167389B2/cs unknown
- 1973-06-19 DK DK337673AA patent/DK131030B/da not_active IP Right Cessation
- 1973-06-19 ZA ZA734127A patent/ZA734127B/xx unknown
- 1973-06-19 HU HUSO1088A patent/HU166936B/hu unknown
- 1973-06-19 CA CA174,384A patent/CA1001170A/fr not_active Expired
- 1973-06-20 CH CH898873A patent/CH568277A5/xx not_active IP Right Cessation
- 1973-06-20 RO RO7375188A patent/RO64465A/ro unknown
- 1973-06-20 KR KR7300971A patent/KR780000231B1/ko not_active Expired
- 1973-09-20 JP JP10686073A patent/JPS553340B2/ja not_active Expired
- 1973-09-20 JP JP10686173A patent/JPS553341B2/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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