EP0268281A2
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EP
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Pyrrolidineamide derivative having anti-prolyl endopeptidase activity, compositions comprising the same, processes for the preparation of the same, and the use of the same for the preparation of a medicament of therapeutic value
Assignee: Suntory Ltd
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Filing: 1987-11-17
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Granted: —
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Expires: 2007-11-17
Abstract
Abstract A novel pyrrolidineamide derivative that exhibits inhibitory activity toward prolyl endopeptidase and its use as an inhibitor against said enzyme are provided. The pyrrolidineamide of the invention has the following general formula: wherein R¹ is benzyloxycarbonyl or a group of the formula: (wherein m is an integer of from 1 to 5) and R² is hydroxy, acyloxy or a group of the formula: (wherein R³ and R⁴ independently are a hydrogen atom, a halogen atom, a lower alkyl or a lower alkoxy). Pharmaceutical compositions comprising such derivatives are also provided together with processes for the production of the derivatives. The use of the derivatives for the manufacture of medicaments of therapeutic value is also provided.
Inventors
- 👤 Masayuki Saitoh
- 👤 Takaharu Tanaka
- 👤 Naoki Higuchi
- 👤 Masaki Hashimoto
- 👤 Harukazu Fukami
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-01 08:31
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/16; A; A61; A61P; A61P25/00; A61P25/28; A61P43/00
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
58 words
A pyrrolidineamide derivative of the general formula (I): wherein R¹ is benzyloxycarbonyl or a group of the formula: (wherein m is an integer of from 1 to 5) and R² is hydroxy, acyloxy or a group of the formula: (wherein R³ and R⁴ independently are a hydrogen atom, a halogen atom, a lower alkyl or a lower alkoxy).
Claim 2
Dependent Claim
58 words
A pyrrolidineamide derivative of the general formula (I): wherein R¹ is benzyloxycarbonyl or a group of the formula: (wherein m is an integer of from 1 to 5) and R² is hydroxy, acyloxy or a group of the formula: (wherein R³ and R⁴ independently are a hydrogen atom, a halogen atom, a lower alkyl or a lower alkoxy).
Claim 3
Dependent Claim
34 words
A compound according to Claim 1 having the formula (II): wherein R¹ is as defined in Claim 1 and R³ is a hydrogen atom, a halogen atom, a lower alkyl or a lower alkoxy.
Claim 4
Dependent Claim
45 words
A compound according to Claim 1 having the formula (III): wherein R¹ is as defined in Claim 1 and R⁵ is lower alkyl or a group of the formula: (wherein R⁴ is a hydrogen atom, a halogen atom, a lower alkyl or a lower alkoxy).
Claim 5
Dependent Claim
28 words
A pharmaceutical composition comprising as the active ingredient a pharmaceutically effective amount of a pyrrolidineamide derivative according to any preceding claim, and a pharmaceutically acceptable diluent or carrier.
Claim 6
Dependent Claim
13 words
A composition according to Claim 4 for use in the alleviation of amnesia.
Claim 7
Dependent Claim
25 words
The use of a pyrrolidineamide derivative according to any of claims 1-3 for the manufacture of a medicament for use in the alleviation of amnesia.
Claim 8
Dependent Claim
54 words
A process for the production of a pyrrolidineamide derivative of formula (V) wherein R¹ is a benzyloxycarbonyl or a group of the formula: wherein m is an integer of from 1 to 5 comprising the step of reacting a compound of formula (IV): wherein R¹ has the same meaning as given above, and pyrrolidine.
Claim 9
Dependent Claim
54 words
A process for the production of a pyrrolidineamide derivative of formula (V) wherein R¹ is a benzyloxycarbonyl or a group of the formula: wherein m is an integer of from 1 to 5 comprising the step of reacting a compound of formula (IV): wherein R¹ has the same meaning as given above, and pyrrolidine.
Claim 10
Dependent Claim
87 words
A process for the production of a pyrrolidineamide derivative of formula (II): wherein R¹ is a benzyloxycarbonyl or a group of the formula: wherein m is an integer of from 1 to 5 and R³ is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, comprising the step of reacting a compound of formula (V): wherein R¹ has the same meaning as given above, and a phenol derivative of general formula (VI): wherein R³ has the same meaning as given above.
Claim 11
Dependent Claim
87 words
A process for the production of a pyrrolidineamide derivative of formula (II): wherein R¹ is a benzyloxycarbonyl or a group of the formula: wherein m is an integer of from 1 to 5 and R³ is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, comprising the step of reacting a compound of formula (V): wherein R¹ has the same meaning as given above, and a phenol derivative of general formula (VI): wherein R³ has the same meaning as given above.
Claim 12
Dependent Claim
114 words
A process for the production of a pyrrolidineamide derivative of formula (III): wherein R¹ is a benzyloxycarbonyl or a group of the formula: wherein m is an integer of from 1 to 5 and R⁵ is a lower alkyl or a group of the formula: wherein R⁴ is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group comprising the step of reacting a compound of formula (V): wherein R¹ has the same meaning as given above and an acid anhydride or carboxylic acid halide of formula R⁵-CO-A, wherein A is a halogen atom or a group of formula R⁵-CO-O-, wherein R⁵ has the same meaning as given above.
Claim 13
Dependent Claim
114 words
A process for the production of a pyrrolidineamide derivative of formula (III): wherein R¹ is a benzyloxycarbonyl or a group of the formula: wherein m is an integer of from 1 to 5 and R⁵ is a lower alkyl or a group of the formula: wherein R⁴ is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group comprising the step of reacting a compound of formula (V): wherein R¹ has the same meaning as given above and an acid anhydride or carboxylic acid halide of formula R⁵-CO-A, wherein A is a halogen atom or a group of formula R⁵-CO-O-, wherein R⁵ has the same meaning as given above.
Claim 14
Dependent Claim
98 words
A process for the production of a pyrrolidineamide derivative of formula (III): wherein R¹ is a benzyloxycarbonyl or a group of the formula: wherein m is an integer of from 1 to 5 and R⁵ is a lower alkyl or a group of the formula: wherein R⁴ is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group comprising the step of reacting a compound of formula wherein R¹ has the same meaning as given above and a carboxylic acid of formula R⁵-CO OH wherein R⁵ has the same meaning as given above.
Claim 15
Dependent Claim
98 words
A process for the production of a pyrrolidineamide derivative of formula (III): wherein R¹ is a benzyloxycarbonyl or a group of the formula: wherein m is an integer of from 1 to 5 and R⁵ is a lower alkyl or a group of the formula: wherein R⁴ is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group comprising the step of reacting a compound of formula wherein R¹ has the same meaning as given above and a carboxylic acid of formula R⁵-CO OH wherein R⁵ has the same meaning as given above.
References Cited (Backward Citations)
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