GB1593851A - N-(4-piperidyl)-benzamides and pharmaceutical compositions containing them - Google Patents
N-(4-piperidyl)-benzamides and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- GB1593851A GB1593851A GB4464976A GB4464976A GB1593851A GB 1593851 A GB1593851 A GB 1593851A GB 4464976 A GB4464976 A GB 4464976A GB 4464976 A GB4464976 A GB 4464976A GB 1593851 A GB1593851 A GB 1593851A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- acid addition
- pharmaceutically acceptable
- acceptable acid
- addition salts
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
An aromatic amide N-substituted by heterocyclic groups of general formula <IMAGE> is obtained by reaction of the substituted benzoic acid of formula <IMAGE> with a compound of formula <IMAGE> in which the radicals R1, R2, R3 and the letters x, y and z correspond to the definition given in Claim 1. The N-substituted aromatic amide thus obtained has the property of antagonising the effects of dopamine.
Description
(54) N-(4-PIPERIDYL)-BENZAMIDES AND
PHARMACEUTICAL COMPOSITIONS CONTAINING
THEM
(71) We, ANTONIO GALLARDO S.A., a Spanish Body Corporate of
Cardoner 68-74, Barcelona 12, Spain, do hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to N-(4-piperidyl)-benzamides and to pharmaceutical compositions containing them. It is an improvement in or modification of the invention described and claimed in the Specification of our British Patent
Applications Nos. 12572/74 and 35402/74 (granted as Patent No. 1,507,462).
In the Specification of British Patent No. 1,507,462 we have described and claimed compounds of the general formula:
(wherein R is a C1-C6 alkoxy or C2-C6 alkenoxy group; Rl and R2, which may be the same or different, are chosen from hydrogen (provided that Rl and R2 are not both hydrogen), halogen, sulphonamido, amino, (C1-C6)-alkyl- or di-(C,--C,)- alkyl-amino, alkylsulphonyl, mono- or di-alkyl-sulphonamido or acylamino groups, the radical R, being positioned at the 3 or 4-position of the aromatic ring; R3 is hydrogen, a C1-C6 alkyl or optionally substituted aryl group, provided that, where z is greater than 1, K3 is hydrogen or two groups R3 on adjacent C-atoms form a bond between the said C-atoms with any remaining groups R3 being hydrogen; Ar is an optionally substituted aryl, aroyl or single ring aromatic heterocyclic group, xis 0 or 1; y is 2 or 3; and z is an integer from 1 to 6, with the exclusion of those compounds of the general formula:
wherein X is chlorine or bromine, R4 is a straight- or branched-chain alkyl group containing up to six carbon atoms, R2 and R, are hydrogen atoms, or one of those symbols is chlorine in the 3- or 4-position of a methyl or methoxy group in the 4 position and the other symbol is a hydrogen atom, or R2 and R3 together represent a methylenedioxy group attached to the 3- and 4-positions) or a pharmaceutically acceptable salt or N-oxide derivative thereof. The compounds are stated to have useful pharmacological properties and, more particularly, the ability to antagonise the effects of dopamine or dopaminergic agents of endogenous or exogenous origin.
The compounds of general formula II are described and claimed in the
Specification of our British Patent No. 1,507,463.
It has now been found that certain compounds falling within the scope of general formula I but which are not specifically disclosed in the specification ot Applications Nos. 12572/74 and 35402/74 (Patent No. 1,507,462) possess the aforesaid pharmacological properties and also properties not hitherto disclosed in respect of compounds of general formula I.
The new compounds of the present invention are N - [1 - (m trifluoromethylbenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino - 5 chlorobenzamide, N - [1 - (I - phenylethyl)piperid - 4 - yll - 2 - ethoxy - 4 amino - 5 - chlorobenzamide, N - [1 - (2 - methoxy - 5 - chlorobenzyl)piperid 4 - yl] - 2 - methoxy - 4 - amino - 5 - chlorobenzamide, N - Il - (A - naphthylmethyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino - 5 chlorobenzamide, N - [1 - (p - bromobenzyl)piperid - 4 - yll - 2 - methoxy - 4 amino - 5 - chlorobenzamide, N - [1 - (p - fluorobenzyl)piperid - 4 - yll - 2 methoxy - 4 - amino - 5 - chlorobenzamide, N - [I - (o - methylbenzyl)piperid 4 - yl] - 2 - methoxy - 4 - amino - 5 - chlorobenzamide, N - (1 benzylpiperid - 4 - yl) - 2 - methoxy - 4,5 - diaminobenzamide, N - [1 - (p nitrobenzyl)piperid - 4 - yll - 2 - methoxy - 4 - amino - 5 - chlorobenzamide N - [1 - (1 - phenylethyl)piperid - 4 - yll - 2 - methoxy - 4 - amino - 5 bromobenzamide, N - [1 - (m - methylbenzyl)piperid - 4 - yli - 2 - methoxy 4 - amino - 5 - chlorobenzamide, N - (1 - benzylpiperid - 4 - yl) - 2 - ethoxy 4 - amino - 5 - chlorobenzamide, N - [1 - (I - phenylethyl)piperid - 4 - yl] - 2 methoxy - 4,5 - diaminobenzamide, N - (1 - benzylpiperid - 4 - yl) - 2 methoxy - 4 - dimethylamino - 5 - chlorobenzamide, N - [1 - (1 phenylethyl)piperid - 4 - yl] - 2 - methoxy - 4 - acetamido - 5 aminobenzamide, N - (1 - benzylpiperid) - 2 - methoxy - 4 - methylamino - 5 - chlorobenzamide, N - (1 - benzylpiperid - 4 - yl) - 2 - allyloxy - 4 - amino - 5 chlorobenzamide, N - (1 -p - methylbenzylpiperid - 4 - yl) - 2 - methoxy - 4 acetamido - 5 - aminobenzamide, N - (I - benzylpiperid - 4 - yl) - 2methoxy - 4 - acetamido - 5 - aminobenzamide, N - Il - (2 - methoxy - 5 - chlorobenzyl)piperid - 4 - yll - 2 - methoxy - 4 - acetamido - 5 aminobenzamide and N - (1 - benzylpiperid - 4- yl)- 2- ethoxy - 4 methylamino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof. These compounds have been found to possess-in addition to the pharmacological properties mentioned in our earlier patent-new activities, the most interesting of which are anorexia (mouse spaghetti test) without amphetamine-like stimulation of the central nervous system, vasodilatation (mouse ear test) and inhibition of gastric acid secretion (pyloric ligature model of Shay) and ulcer formation (phenylbutazone or stress models) in the rat.
The new compounds may be prepared by application of the methods
described in the specification of Applications Nos. 12572/74 and 35402/74 (Patent
No. 1,507,462) for the preparation of compounds of general formula I. Their acid
addition salts may be prepared by reacting the bases in a solvent such as methanol, ethanol, acetone or water, or a suitable mixture of such solvents, at a temperature
between 10"C and the boiling point of the reaction mixture.
The present invention also includes within its scope pharmaceutical
compositions comprising one or more of the afore-named compounds, or a
pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutical carrier. The pharmaceutical carrier may be a solid, a liquid or a
mixture of a solid and a liquid, and the compositions of this invention may be
adapted for oral, rectal or parenteral use, the preferred method of administriation being per os. In this case, the compositions may take the form of tablets, capsules, lozenges, effervescent granules, syrups or suspensions. Such compositions may be made by methods well known in the art.
The following Example illustrates the preparation in detail of one of the compounds of the invention. Other compounds of the invention may be prepared in a similar manner.
EXAMPLE
N - [I - (m - Trifluoromethylbenzyl)piperid - 4 - yli - 2 - methoxy - 4 - amino
5 - chlorobenzamide
To a suspension of 6.0 g of 2 - methoxy - 4 - amino - 5 - chlorobenzoic acid in 400 ml of anhydrous tetrahydrofuran, a solution of 4.2 ml of triethylamine in 28 ml of tetrahydrofuran was added. The resulting solution was cooled to --100C and then a solution of 2.98 ml of ethyl chloroformate in 25 ml of tetrahydrofuran was slowly added. The mixture was stirred at the same temperature for half an hour and a solution of 8.58 g of I - (m - trifluoromethylbenzyl) - 4 - aminopiperidine in 25 ml of tetrahydrofuran was added. After stirring for 1 hour at -10 to -50C, the temperature was allowed to rise to room temperature and the reaction mixture was left to stand overnight. The mixture was evaporated to dryness and the residue dissolved in a mixture of chloroform and water. The mixture was made strongly basic with sodium hydroxide solution, the chloroform phase was separated and washed with water, dried (sodium sulphate) and evaporated to dryness to yield 9.5 g of the title compound, m.p. 138-140 C (after crystallization from acetone/n-hexane). Its hydrochloride melted at 219-221 C.
By a similar procedure and using appropriate starting materials and appropriate quantities thereof, the following compounds were prepared: N - [I - (I - phenylethyl)piperid - 4 - yl] - 2 - ethoxy - 4 - amino - 5 - chlorobenzamide, the hydrochloride of which melts at 282-284 C;
N - [I - - (2 - methoxy - 5 - chlorobenzyl)piperid - 4 - yli - 2 - methoxy 4 - amino - 5 - chlorobenzamide, the hydrochloride of which melts at
200-203 C; N - [I - ( - naphthylmethyl)piperid - 4 - yl) - 2 - methoxy - 4 - amino
5 - chlorobenzamide, the hydrochloride of which melts at 22-2210C; N - [1 - (p - bromobenzyl)piperid - 4 - yll - 2 - methoxy - 4 - amino - 5 - chlorobenzamide, the hydrochloride of which melts at 242-2430C; N - [1 - (p - fluorobenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino - 5 - chlorobenzamide, the hydrochloride monohydrate of which melts at 256-2580C (dec.); N - [1 - (o - methylbenzyl)piperid - 4 - ylj - 2 - methoxy - 4 - amino - 5 - chlorobenzamide the hydrochloride of which melts at 186-188 C; N - (1 - benzylpiperid - 4 - yl) - 2 - methoxy - 4,5 - diaminobenzamide, the
hydrochloride monohydrate of which melts at 24-2460C; N - [1 - (p - nitrobenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino - 5 - chlorobenzamide, the hydrochloride of which melts at 223--2250C; N - [1 - (1 - phenylethyl)piperid -4-y.l] - 2 - methoxy .4 - amino - 5 - bromobenzamide, the hydrochloride of which melts at 239-241 0C; N - [1 - (m - methylbenzyl)piperid - 4 - yli - 2 - methoxy - 4 - amino - 5 - chlorobenzamide, the hydrochloride of which melts at 217-219 C; N - (1 - benzylpiperid - 4 - yl) - 2 - ethoxy - 4 - amino - 5
chlorobenzamide, the hydrochoride of which melts at 271--2730C; N - [1 - (1 - phenylethyl)piperid - 4 - yli - 2 - methoxy - 4,5
diaminobenzamide, the dihydrochloride monohydrate of which melts at
246-248 C;
N - (I - benzylpiperid - 4 - yl) - 2 - methoxy - 4
dimethylamino - 5 - chlorobenzamide, the fumarate of which melts at
185-187 C; Bison - [I - (1 - phenylethyl)piperid - 4 - yl] - 2
methoxy - 4 - acetamido - 5 - aminobenzamidelfumarate, m.p.
165--1660C; N - (1 - benzylpiperid - 4 - yl) - 2 - methoxy - 4 - methylamino 5 - chlorobenzamide, the fumarate of which melts at 221-2220C (dec.); N - ( I - benzylpiperid - 4 - yl) - 2 - allyloxy - 4 - amino - 5
chlorobenzamide, the hydrochloride of which melts at 2230--2250C; N - (1 - p - methylbenzylpiperid - 4 - yl) - 2 - methoxy - 4 - acetamido 5 - aminobenzamide, the fumarate of which melts at 172-174 C (dec.); N - (1 - benzylpiperid - 4 - yl) - 2 - methoxy - 4 - acetamido - 5
aminobenzamide, the fumarate of which melts at 177-179 C; N - [1 - - (2 - methoxy - 5 - chlorobenzyl)piperid - 4 - yli - 2 - methoxy 4 - acetamido - 5 - aminobenzamide, the fumarate of which melts at
182-184 C (dec.); and N - (1 - benzylpiperid - 4 - yl) - 2 - ethoxy - 4 - methylamino - 5 - chlorobenzamide, the fumarate of which melts at 229-,23l0C (dec.).
WHAT WE CLAIM IS:
1. N - [1 - (m-Trifluoromethylbenzyl)piperid - 4 - yl] - 2 - methoxy - 4 amino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
2. N - [1 - (I - Phenylethyl)piperid - 4 - yl] - 2 - ethoxy - 4 - amino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
3. N - [I - (2 - Methoxy - 5 - chlorobenzyl)piperid - 4 - yl] - 2 - methoxy 4 - amino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
4. N - [I - ( - Naphthylmethyl)piperid - 4 - yll - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
5. N - [1 - (p - Bromobenzyl)piperid - 4 - yll - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
6. N - [1 - (p - Fluorobenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceuticlly acceptable acid addition salts thereof.
7. N - [I - (o - Methylbenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
8. N - (1 - Benzylpiperid - 4 - yl) - 2 - methoxy - 4,5 - diaminobenzamide and pharmaceutically acceptable acid addition salts thereof.
9. N - [I - (p - Nitrobenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino - 5 chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
10. N - [1 - (I - Phenylethyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino 5 - bromobenzamide and pharmaceutically acceptable acid addition salts thereof.
11. N - [I - (m - Methylbenzyl)piperid - 4 - yll - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
12. N - (1 - Benzylpiperid - 4 - yl) - 2 - ethoxy - 4 - amino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
13. N - [1 - (1 - Phenylethyl)piperid - 4 - yl] - 2 - methoxy - 4,5 diaminobenzamide and pharmaceutically acceptable acid addition salts thereof.
14. N - (1 - Benzylpiperid - 4 - yl) - 2 - methoxy - 4 - dimethylamino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
15. N - tl - ( I - Phenylethyl)piperid - 4 - yl] - 2 - methoxy - 4 - acetamido - 5 - aminobenzamide and pharmaceutically acceptable acid addition salts thereof.
16. M - (1 - Benzylpiperid - 4 - yl) - 2 - methoxy - 4 - methylamino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
17. N - (1 - Benzylpiperid - 4 - yl) - 2 - allyloxy - 4 - amino - 5chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
18. N - (I - p - Methylbenzylpiperid - 4 - yl) - 2 - methoxy - 4 - acetamido 5 - aminobenzamide and pharmaceutically acceptable acid addition salts thereof.
19. N - (1 - Benzylpiperid - 4 - yl) - 2 - methoxy - 4 - acetamido - 5 - aminobenzamide and pharmaceutically acceptable acid addition salts thereof.
20. N - [1 - (2 - Methoxy - 5 - chlorobenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - acetamido - 5 - aminobenzamide and pharmaceutically acceptable acid addition salts thereof.
21. N - (1 - Benzylpiperid - 4 - yl) - 2 - ethoxy - 4 - methylamino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
22. A pharmaceutical composition which comprises an N - (4 - piperidyl) benzamide claimed in any one of claims 1 to 12, or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutically carrier.
23. A pharmaceutical composition which comprises an N - (4 - piperidyl) benzamide claimed in any one of claims 13 to 21, or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutical carrier.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (23)
1. N - [1 - (m-Trifluoromethylbenzyl)piperid - 4 - yl] - 2 - methoxy - 4 amino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
2. N - [1 - (I - Phenylethyl)piperid - 4 - yl] - 2 - ethoxy - 4 - amino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
3. N - [I - (2 - Methoxy - 5 - chlorobenzyl)piperid - 4 - yl] - 2 - methoxy 4 - amino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
4. N - [I - ( - Naphthylmethyl)piperid - 4 - yll - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
5. N - [1 - (p - Bromobenzyl)piperid - 4 - yll - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
6. N - [1 - (p - Fluorobenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceuticlly acceptable acid addition salts thereof.
7. N - [I - (o - Methylbenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
8. N - (1 - Benzylpiperid - 4 - yl) - 2 - methoxy - 4,5 - diaminobenzamide and pharmaceutically acceptable acid addition salts thereof.
9. N - [I - (p - Nitrobenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino - 5 chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
10. N - [1 - (I - Phenylethyl)piperid - 4 - yl] - 2 - methoxy - 4 - amino 5 - bromobenzamide and pharmaceutically acceptable acid addition salts thereof.
11. N - [I - (m - Methylbenzyl)piperid - 4 - yll - 2 - methoxy - 4 - amino 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
12. N - (1 - Benzylpiperid - 4 - yl) - 2 - ethoxy - 4 - amino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
13. N - [1 - (1 - Phenylethyl)piperid - 4 - yl] - 2 - methoxy - 4,5 diaminobenzamide and pharmaceutically acceptable acid addition salts thereof.
14. N - (1 - Benzylpiperid - 4 - yl) - 2 - methoxy - 4 - dimethylamino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
15. N - tl - ( I - Phenylethyl)piperid - 4 - yl] - 2 - methoxy - 4 - acetamido - 5 - aminobenzamide and pharmaceutically acceptable acid addition salts thereof.
16. M - (1 - Benzylpiperid - 4 - yl) - 2 - methoxy - 4 - methylamino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
17. N - (1 - Benzylpiperid - 4 - yl) - 2 - allyloxy - 4 - amino - 5chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
18. N - (I - p - Methylbenzylpiperid - 4 - yl) - 2 - methoxy - 4 - acetamido 5 - aminobenzamide and pharmaceutically acceptable acid addition salts thereof.
19. N - (1 - Benzylpiperid - 4 - yl) - 2 - methoxy - 4 - acetamido - 5 - aminobenzamide and pharmaceutically acceptable acid addition salts thereof.
20. N - [1 - (2 - Methoxy - 5 - chlorobenzyl)piperid - 4 - yl] - 2 - methoxy - 4 - acetamido - 5 - aminobenzamide and pharmaceutically acceptable acid addition salts thereof.
21. N - (1 - Benzylpiperid - 4 - yl) - 2 - ethoxy - 4 - methylamino - 5 - chlorobenzamide and pharmaceutically acceptable acid addition salts thereof.
22. A pharmaceutical composition which comprises an N - (4 - piperidyl) benzamide claimed in any one of claims 1 to 12, or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutically carrier.
23. A pharmaceutical composition which comprises an N - (4 - piperidyl) benzamide claimed in any one of claims 13 to 21, or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutical carrier.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2513136A DE2513136C3 (en) | 1974-03-21 | 1975-03-21 | N- (1-Benzylpiperid-4-yl) -benzamides, process for their preparation and pharmaceutical preparations containing them |
| GB4464976A GB1593851A (en) | 1976-10-27 | 1976-10-27 | N-(4-piperidyl)-benzamides and pharmaceutical compositions containing them |
| NL7711690A NL7711690A (en) | 1976-10-27 | 1977-10-25 | PROCEDURE FOR PREPARING NITROGEN SUBSTITUTED BENZAMIDES. |
| CH1295177A CH625219A5 (en) | 1976-10-27 | 1977-10-25 | Process for the manufacture of an aromatic amide N-substituted by heterocyclic groups |
| BE182086A BE860139R (en) | 1976-10-27 | 1977-10-26 | AROMATIC AMIDS OF HETEROCYCLIC COMPOUNDS. AND THEIR PREPARATION |
| FR7733111A FR2378762A2 (en) | 1976-10-27 | 1977-10-26 | AROMATIC AMIDES OF HETEROCYCLIC COMPOUNDS AND THEIR APPLICATION AS A MEDICINAL PRODUCT |
| ES463557A ES463557A2 (en) | 1976-10-27 | 1977-10-26 | N-(4-piperidyl)-benzamides and pharmaceutical compositions containing them |
| CA289,550A CA1085855A (en) | 1976-10-27 | 1977-10-26 | N-piperid-4-yl benzamide compounds |
| DE19772747961 DE2747961A1 (en) | 1974-03-21 | 1977-10-26 | AROMATIC AMIDES OF HETEROCYCLIC COMPOUNDS |
| JP12915777A JPS5392783A (en) | 1976-10-27 | 1977-10-27 | Nnsubstituted benzamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4464976A GB1593851A (en) | 1976-10-27 | 1976-10-27 | N-(4-piperidyl)-benzamides and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1593851A true GB1593851A (en) | 1981-07-22 |
Family
ID=10434204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4464976A Expired GB1593851A (en) | 1974-03-21 | 1976-10-27 | N-(4-piperidyl)-benzamides and pharmaceutical compositions containing them |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5392783A (en) |
| BE (1) | BE860139R (en) |
| CA (1) | CA1085855A (en) |
| CH (1) | CH625219A5 (en) |
| ES (1) | ES463557A2 (en) |
| FR (1) | FR2378762A2 (en) |
| GB (1) | GB1593851A (en) |
| NL (1) | NL7711690A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001036385A1 (en) * | 1999-11-17 | 2001-05-25 | Kissei Pharmaceutical Co., Ltd. | Hydroxyethoxybenzamide derivatives and drugs containing the same |
| US7285564B2 (en) | 2002-10-30 | 2007-10-23 | Theravance, Inc. | Substituted 4-amino-1-(pyridylmethyl)piperidine and related compounds |
| US7368463B2 (en) | 2003-07-11 | 2008-05-06 | Theravance, Inc. | Substituted 4-amino-1-benzylpiperidine compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5916M (en) * | 1966-01-21 | 1968-05-06 | ||
| GB1345872A (en) * | 1970-09-03 | 1974-02-06 | Wyeth John & Brother Ltd | Amino-and acylamino-pyridine and hydropyridine derivatives |
-
1976
- 1976-10-27 GB GB4464976A patent/GB1593851A/en not_active Expired
-
1977
- 1977-10-25 CH CH1295177A patent/CH625219A5/en not_active IP Right Cessation
- 1977-10-25 NL NL7711690A patent/NL7711690A/en not_active Application Discontinuation
- 1977-10-26 BE BE182086A patent/BE860139R/en not_active IP Right Cessation
- 1977-10-26 CA CA289,550A patent/CA1085855A/en not_active Expired
- 1977-10-26 FR FR7733111A patent/FR2378762A2/en active Granted
- 1977-10-26 ES ES463557A patent/ES463557A2/en not_active Expired
- 1977-10-27 JP JP12915777A patent/JPS5392783A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001036385A1 (en) * | 1999-11-17 | 2001-05-25 | Kissei Pharmaceutical Co., Ltd. | Hydroxyethoxybenzamide derivatives and drugs containing the same |
| US7285564B2 (en) | 2002-10-30 | 2007-10-23 | Theravance, Inc. | Substituted 4-amino-1-(pyridylmethyl)piperidine and related compounds |
| US7368463B2 (en) | 2003-07-11 | 2008-05-06 | Theravance, Inc. | Substituted 4-amino-1-benzylpiperidine compounds |
| US8080565B2 (en) | 2003-07-11 | 2011-12-20 | Theravance, Inc. | Substituted 4-amino-benzylpiperidine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7711690A (en) | 1978-05-02 |
| JPS5392783A (en) | 1978-08-15 |
| CA1085855A (en) | 1980-09-16 |
| ES463557A2 (en) | 1978-11-16 |
| CH625219A5 (en) | 1981-09-15 |
| FR2378762A2 (en) | 1978-08-25 |
| FR2378762B2 (en) | 1980-09-12 |
| BE860139R (en) | 1978-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19950309 |