GB797476A - Amides of trialkoxybenzoic acids - Google Patents
Amides of trialkoxybenzoic acidsInfo
- Publication number
- GB797476A GB797476A GB23780/56A GB2378056A GB797476A GB 797476 A GB797476 A GB 797476A GB 23780/56 A GB23780/56 A GB 23780/56A GB 2378056 A GB2378056 A GB 2378056A GB 797476 A GB797476 A GB 797476A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- phenyl
- ethyl
- dimethylamino
- 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
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 3
- 150000001408 amides Chemical class 0.000 title abstract 3
- -1 alkylene radical Chemical class 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 2
- 239000005711 Benzoic acid Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- QNMOTJZJRDYUPF-UHFFFAOYSA-N 4-(4-nitrosophenyl)morpholine Chemical compound C1=CC(N=O)=CC=C1N1CCOCC1 QNMOTJZJRDYUPF-UHFFFAOYSA-N 0.000 abstract 1
- PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 abstract 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 229960005070 ascorbic acid Drugs 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229940074391 gallic acid Drugs 0.000 abstract 1
- 235000004515 gallic acid Nutrition 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 abstract 1
- 238000006263 metalation reaction Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0797476/IV (b)/1> (wherein R is alkyl of 1 to 4 carbon atoms, R1 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or phenethyl, A is an alkylene radical of 2 to 6 carbon atoms or a phenylene radical which may be substituted by halogen atoms or nitro groups and B is dialkylamino, dicycloalkylamino, diaralkylamino, alkylaralkylamino or a saturated, heterocyclic nitrogen containing ring system which may be alkyl substituted and which is connected to A through a heterocyclic nitrogen atom) and acid-addition salts thereof; and their preparation by reacting a halide, ester or azide of the appropriate trialkoxy-benzoic acid with a compound R1-NH-A-B. They may also be prepared by metallation, e.g. with sodium or lithium amide, of the amide of a trialkoxy-benzoic acid and reaction of the metallated amide with the appropriate tertiary aminoalkyl halide or amino phenyl halide. In examples, the following compounds are prepared by reaction of 3 : 4 : 5-trimethoxy-benzoyl chloride with the appropriate primary or secondary amine: N-(b -morpholinoethyl)-, N-methyl - N - (b - morpholinoethyl)-, N - (5 - di - ethylamino - 2 - pentyl)-, N - benzyl - N - (b -morpholinoethyl)-, N - (g - morpholinopropyl)-, N - (b - piperidimoethyl)-, N - (5 - di - n - propylamino - 1 - pentyl)-, N - ethyl - N - (6 - di - n - hexylamino - 1 - hexyl)-, N - [b - (2 - methylpiperidino) - ethyl]-, N - (b - 1 - pyrrolidinyl)-, N - (n - butyl) - N - (b - 1 - pyrrolidinyl)-, N-[4-(N1 - methyl - 1 - piperazinyl) - butyl]-, N-[b -(2 : 6 - dimethylmorpholino) - ethyl]-, N - (b -di-n - hexylaminoethyl)-, N - (b - benzylmethylaminoethyl)-, N - (p - dimethylaminophenyl)-, N - methyl - N - (p - morpholinophenyl)-, N-benzyl - N - (p - piperidinophenyl)-, N - phen - ethyl - N - [p - (a - pipecolinophenyl)]- N-(3 : 5-dichloro - 4 - dimethylamino - phenyl)-, N-(3 : 5-dinitro - 4 - dimethylamino - phenyl)-, N-(3-chloro - 4 - dimethylamino - phenyl)-, N-(3-nitro - 4 - dimethylamino - phenyl)-, N - (p-morpholinophenyl)- and N-benzyl-N-(p-dimethylaminophenyl) - 3 : 4 : 5 - trimethoxybenzamides, and the corresponding triethoxy- and tri-n-hexyloxy compounds corresponding to the first 15 compounds in the above list. Acid-addition salts of some of the products are described and a list of further salt-forming acids including inorganic acids, organic carboxylic acids, ascorbic acid and 8-chlorotheophylline is given. Starting materials. 3 : 4 : 5-Triethoxy- and -tri-n-hexyloxy benzoyl chlorides are prepared from thionyl chloride and the parent acids which in turn are prepared by alkylation of gallic acid, e.g. with ethyl bromide in sodium hydroxide, followed, if necessary, by saponification of any ester formed. N-(p-aminophenyl)-morpholine is prepared by catalytic hydrogenation of N-(p-nitrosophenyl)-morpholine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US797476XA | 1955-09-09 | 1955-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB797476A true GB797476A (en) | 1958-07-02 |
Family
ID=22152548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23780/56A Expired GB797476A (en) | 1955-09-09 | 1956-08-01 | Amides of trialkoxybenzoic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB797476A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177252A (en) * | 1961-07-25 | 1965-04-06 | Ile De France | Ortho alkoxy and alkylthio-polysubstituted-n-tertiaryamino-alkyl benzamides |
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| JP2017014267A (en) * | 2008-08-29 | 2017-01-19 | 日本たばこ産業株式会社 | Novel potassium channel blocker |
| EP2786986B1 (en) * | 2011-11-29 | 2018-02-28 | Vivozon, Inc. | Novel benzamide derivative and use thereof |
-
1956
- 1956-08-01 GB GB23780/56A patent/GB797476A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177252A (en) * | 1961-07-25 | 1965-04-06 | Ile De France | Ortho alkoxy and alkylthio-polysubstituted-n-tertiaryamino-alkyl benzamides |
| US3312739A (en) * | 1961-07-25 | 1967-04-04 | Ile De France | N-(substituted amino alkyl)-2-alkoxysulfamoyl benzamides |
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| JP2017014267A (en) * | 2008-08-29 | 2017-01-19 | 日本たばこ産業株式会社 | Novel potassium channel blocker |
| EP2786986B1 (en) * | 2011-11-29 | 2018-02-28 | Vivozon, Inc. | Novel benzamide derivative and use thereof |
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