FI60860B - NAM (DIETHYLAMINOETHYL) -2-METOXY-4-AMINO-5-CHLORBENZAMIDE - Google Patents
NAM (DIETHYLAMINOETHYL) -2-METOXY-4-AMINO-5-CHLORBENZAMIDE Download PDFInfo
- Publication number
- FI60860B FI60860B FI267374A FI267374A FI60860B FI 60860 B FI60860 B FI 60860B FI 267374 A FI267374 A FI 267374A FI 267374 A FI267374 A FI 267374A FI 60860 B FI60860 B FI 60860B
- Authority
- FI
- Finland
- Prior art keywords
- amino
- diethylaminoethyl
- methoxy
- chlorbenzamide
- metoxy
- Prior art date
Links
Classifications
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
[--^"71 rRl KU ULUTUSJULKAISU /Λ0/;λ[- ^ "71 rRl KU RELEASE PUBLICATION / Λ0 /; λ
^ (11) UTLÄGGN I NGSSKRIFT » U O O U^ (11) UTLÄGGN I NGSSKRIFT »U O O U
• C (45) Patentti tayinne !.ty 13 04 1932 »SpV]2/ Patent aeddelat ^ ^ (51) Kv.lk?/lnt.CI.3 C 07 G 103/82 SUO M I—FI N LAN D (M) Pttanttlhckemus — Pmntanteknlng 2 6 73/T^4 (22) H*k»mlsp«y> — Anseknlngsdag 12.09· 7*+ (23) Alkupftlvt—&lltigh*tsdag 12.09.7¼ (41) Tullut julkisti il — Bllvlt offtntlig l8.03.75• C (45) Patent Tayinne! .Ty 13 04 1932 »SpV] 2 / Patent aeddelat ^ ^ (51) Kv.lk?/lnt.CI.3 C 07 G 103/82 SUO MI — FI N LAN D (M ) Pttanttlhckemus - Pmntanteknlng 2 6 73 / T ^ 4 (22) H * k »mlsp« y> - Anseknlngsdag 12.09 · 7 * + (23) Alkupftlvt— & lltigh * tsdag 12.09.7¼ (41) .03.75
Patentti- ja rekisterihallitus .... ......... , . ,. „ , _ ' , , (44) Nihtivikilpan m ja kuuL|ulkaliun pvm. —Patent and Registration Office .... ......... , . ,. „, _ ',, (44) Date of mite shield m and moonbone | -
Patent- och registerstyrelsen Ansökin utlag I och utl.skriftan publkarad 31 .12.81 (32)(33)(31) Pyydi tty etuoikeus—Begird prloritet ΐγ.09.73 Ranska-Franl rike(FR) 73/33513 (71) Societe d'Studes Scientifiques et Induslrielles de 1'Ile-de-France, 1+6,boulevard de Latour-Maubourg, 75 Paris 7°» Ranska-Frankrike(FR) (72) Gerard Bulteau, Paris, Jacques Acher, Itteville, Jean-Claude Monier,Patent and registration authorities Ansökin utlag I och utl.skriftan publkarad 31 .12.81 (32) (33) (31) Pyydi tty privilege — Begird prloritet ΐγ.09.73 Scientifiques et Induslrielles de 1'Ile-de-France, 1 + 6, boulevard de Latour-Maubourg, 75 Paris 7 ° »France-France (FR) (72) Gerard Bulteau, Paris, Jacques Acher, Itteville, Jean-Claude Monier ,
Lardy, Ranska-Frankrike(FR) (7I+) Oy Kolster Ab (51+) Uusi tapa valmistaa N-(dietyyliaminoetyjli)-2-metoksi-l+-amino-5-kloori -bentsamidia - Nytt sätt att framställa t-(dietylaminoetyl)-2-metoxy-l+--amino-5-klorbenzamid Tämä keksintö kohdistuu uuteen tajaan valmistaa N-(dietyyliaminoetyyli)-2-metoksi-4-amino-5-klooribentsamidia (i), sen additiosuoloja farmaseuttisesti hyväksyttävien mineraali- tai orgaanisien happojen kanssa ja kvartäärisiä ammoniumsuoloja, joita valmistetaan saatlamalla bentsamidi (i) reagoimaan ali-faattisen tai aromaattisen alkyloivan aineen kanssa.Lardy, France-France (FR) (7I +) Oy Kolster Ab (51+) A new way to prepare N- (diethylaminoethyl) -2-methoxy-1 + -amino-5-chloro-benzamide - Nytt sätt att framställa t- (diethylaminoethyl) This invention relates to a novel process for the preparation of N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide (i), its addition salts with pharmaceutically acceptable mineral or organic acids. and quaternary ammonium salts prepared by reacting benzamide (i) with an aliphatic or aromatic alkylating agent.
Bentsamidilla, jonka valmistukseen keksintö kohdistuu, on seuraava kaava: C2H5 CO-UH-CHg-CHg-N^ .. Xc2a5 _ OCHjThe benzamide of which the invention is directed has the following formula: C2H5 CO-UH-CH2-CH2-N2.
Ci -Ci -
m2 Im2 I
« 5 i t i 2 60860«5 i t i 2 60860
Bentsamidilla (i) on miellyttäviä farmakologisia ominaisuuksia kuten samat hakijat kuvaavat ranskalaisessa patentissa nso I525M, jätetty 25·7·196ΐ.Benzamide (i) has pleasant pharmacological properties as described by the same applicants in the French patent nso I525M, filed 25 · 7 · 196ΐ.
Keksinnön mukainen menetelmä voidaan esittää kaavlomaisesti seuraavasti:The method according to the invention can be schematically represented as follows:
COOHCOOH
-OZK- /C2K5 \[ + R2t:"CR2"CH2"N\-OZK- / C2K5 \ [+ R2t: "CR2" CH2 "N \
C1“V /AC1 “V / A
NH- CO-NH-CH.-CH^n.NH-CO-NH-CH.-CH2.
^ H-CCH^ P-Or ^ JLL_j ci— iJH2^ H-CCH ^ P-Or ^ JLL_j ci - iJH2
Sen mukaan käsitellään 2-metoksi-4-aniiiio-5-klooribentsoehappoa, jonka valmistusta samat hakijat ovat kuvanneet englantilaisessa patenttijulkaisussa n:o 7146333« dietyyliaminoetyyliamiinilla fosforihappoanhydridin läsnäollessa. Seuraava esimerkki kuvaa» mutta ei rajoita tätä keksintöä. N-(dietyyliaminoetyyli)-2-metoksi-4-aminö-5-klooribentsamidi 6,1 g (0,03 moolia) 2-metoksi-4-amino-5-klooribentsoehappoa ja 7 g (0,06 moolia) dietyyliaminoetyyliamiinia asetetaan sekoittajalla, ja lämpömittarilla varustettuun 250 ml:n pallomaiseen pulloon.It relates to 2-methoxy-4-anilio-5-chlorobenzoic acid, the preparation of which is described by the same applicants in British Patent Publication No. 7146333 to diethylaminoethylamine in the presence of phosphoric anhydride. The following example illustrates »but does not limit the present invention. N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide 6.1 g (0.03 mol) of 2-methoxy-4-amino-5-chlorobenzoic acid and 7 g (0.06 mol) of diethylaminoethylamine are placed on a stirrer , and a 250 ml spherical flask with a thermometer.
Kuumentamalla seos lämpötilaan 100°C, aikaansaadaan homogeeninen öljy. Tähän viedään 6,5 g (0,045 moolia) fosforihappoanhydridiä. Jatketaan hellävaraista kuumentamista ja kun lämpötila saavuttaa arvon noin 110°C, kohoaa lämpötila muutamissa sekunneissa arvoon 150-l60°C.By heating the mixture to 100 ° C, a homogeneous oil is obtained. 6.5 g (0.045 mol) of phosphoric anhydride are introduced here. Gentle heating is continued and when the temperature reaches about 110 ° C, the temperature rises to 150-160 ° C in a few seconds.
Tämä lämpötila pidetään 20 minuutin ajan, jota seuraa jäähdyttäminen lämpötilaan noin 100° C. Sitten lisätään 100 ml vettä. Täydellisen liukenemi- 3 60860 sen jälkeen lisätään natriumhydroksidia. Sitten liuos Jätetään jäähtymään jota seuraa suodatus. Saostuma pestään vedellä ja kuivataan kuivausuunissa lämpötilassa 50°C.This temperature is maintained for 20 minutes, followed by cooling to about 100 ° C. Then 100 ml of water are added. After complete dissolution, sodium hydroxide is then added. The solution is then allowed to cool followed by filtration. The precipitate is washed with water and dried in a drying oven at 50 ° C.
Saadaan 8,4 e (saanto: 95»5 $) N-( dietyyliaminoetyyli)-2-metoksi-4-amino-5-klooribentsamidia (sulamispiste: 146°c).8.4 e (yield: 95> 5) of N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide (melting point: 146 ° c) are obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7333513 | 1973-09-17 | ||
| FR7333513A FR2243933B1 (en) | 1973-09-17 | 1973-09-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI267374A FI267374A (en) | 1975-03-18 |
| FI60860B true FI60860B (en) | 1981-12-31 |
| FI60860C FI60860C (en) | 1982-04-13 |
Family
ID=9125223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI267374A FI60860C (en) | 1973-09-17 | 1974-09-12 | NAM (DIETHYLAMINOETHYL) -2-METOXY-4-AMINO-5-CHLORBENZAMIDE |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5053344A (en) |
| AR (1) | AR200468A1 (en) |
| AT (1) | AT338766B (en) |
| CA (1) | CA1028719A (en) |
| CY (1) | CY973A (en) |
| DE (1) | DE2442930A1 (en) |
| ES (1) | ES430021A1 (en) |
| FI (1) | FI60860C (en) |
| FR (1) | FR2243933B1 (en) |
| GB (1) | GB1441352A (en) |
| IE (1) | IE39848B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808624A (en) * | 1984-06-28 | 1989-02-28 | Bristol-Myers Company | Pharmacologically active substituted benzamides |
-
1973
- 1973-09-17 FR FR7333513A patent/FR2243933B1/fr not_active Expired
-
1974
- 1974-09-04 CY CY97374A patent/CY973A/en unknown
- 1974-09-05 GB GB3890574A patent/GB1441352A/en not_active Expired
- 1974-09-07 DE DE19742442930 patent/DE2442930A1/en not_active Withdrawn
- 1974-09-12 JP JP10590574A patent/JPS5053344A/ja active Pending
- 1974-09-12 CA CA209,119A patent/CA1028719A/en not_active Expired
- 1974-09-12 AT AT736274A patent/AT338766B/en not_active IP Right Cessation
- 1974-09-12 FI FI267374A patent/FI60860C/en active
- 1974-09-13 AR AR25559374A patent/AR200468A1/en active
- 1974-09-13 IE IE190574A patent/IE39848B1/en unknown
- 1974-09-13 ES ES430021A patent/ES430021A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2243933B1 (en) | 1978-06-30 |
| IE39848L (en) | 1975-03-17 |
| DE2442930A1 (en) | 1975-03-20 |
| GB1441352A (en) | 1976-06-30 |
| CA1028719A (en) | 1978-03-28 |
| FI60860C (en) | 1982-04-13 |
| ATA736274A (en) | 1977-01-15 |
| AR200468A1 (en) | 1974-11-08 |
| FI267374A (en) | 1975-03-18 |
| FR2243933A1 (en) | 1975-04-11 |
| AT338766B (en) | 1977-09-12 |
| ES430021A1 (en) | 1976-09-16 |
| JPS5053344A (en) | 1975-05-12 |
| IE39848B1 (en) | 1979-01-17 |
| CY973A (en) | 1978-12-22 |
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