Patent US2435805A successfully refreshed from Google Patents.
EP0046572A2
Expired / Lapsed
EP
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6-Quinazolinesulfonyl derivatives and process for preparation thereof
Assignee: Asahi Kasei Corp
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Filing: 1981-08-19
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Granted: —
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Expires: 2001-08-19
Abstract
Abstract A 6-quinazolinesulfonyl derivative of Formula (I): wherein R 1 is a hydrogen atom or a C 1-12 alkyl group: R 2 is a hydrogen atom, a C 1-12 alkyl group, a C 4-10 cycloalkyl group, an aryl group or an aralkyl group; and R 1 and R 2 may be linked directly or through an oxygen atom to form a 5- to 7-membered heterocyclic ring together with the adjacent nitrogen atom; and R 3 is a group wherein R is a C 1-8 alkyl group; a -NH(CH 2 ) n NH 2 group wherein n is an integer of 2 to 10; or a group; and the pharmaceutically acceptable salts thereof; and a process for the preparation thereof. The compounds of this invention have a relaxatory action for vascular smooth muscle and are useful as a vasodilator and a hypotensor.
Inventors
- 👤 Hiroyoshi Hidaka
- 👤 Takanori Sone
- 👤 Yasuharu Sasaki
- 👤 Taisuke Sugihara
- 👤 Seiji Takagi
- 👤 Kiyohide Sako
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 04:17
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/70; C07D239/72; C07D239/86; C07D239/94; C07D239/88
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
116 words
A compound of formula (I): wherein R 1 is a hydrogen atom or a C 1-12 alkyl group; R2 is a hydrogen atom, a C 1-12 alkyl group, a C 4-10 cycloalkyl group, an aryl group or an aralkyl group; and R 1 and R 2 may be C 1-6 alkylene groups and linked directly or through an oxygen atom to form a 5- to 7-membered heterocyclic ring together with the adjacent nitrogen atom; and R 3 is a group wherein R 4 is a C 1-8 alkyl group; a -NH(CH 2 ) n NH 2 group wherein n is an integer of 2 to 10; or a group;- and pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
116 words
A compound of formula (I): wherein R 1 is a hydrogen atom or a C 1-12 alkyl group; R2 is a hydrogen atom, a C 1-12 alkyl group, a C 4-10 cycloalkyl group, an aryl group or an aralkyl group; and R 1 and R 2 may be C 1-6 alkylene groups and linked directly or through an oxygen atom to form a 5- to 7-membered heterocyclic ring together with the adjacent nitrogen atom; and R 3 is a group wherein R 4 is a C 1-8 alkyl group; a -NH(CH 2 ) n NH 2 group wherein n is an integer of 2 to 10; or a group;- and pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
145 words
2 . A compound of claim 1 of formula (I) wherein R 1 is a hydrogen atom or a C 1-6 alkyl group, R 2 is a hydrogen atom, a C 1-6 alkyl, C 5-7 cycloalkyl, aryl (which can be substituted with at least one hydrogen atom, preferably chloro or bromo atom, or methyl group) or aralkyl group (which can be substituted with at least one halogen atom, preferably fluoro or chloro atom); or R 1 and R 2 are C 1-6 alkylene groups and linked directly or through an oxygen atom to form a 5- to 6- or 7-membered heterocyclic ring together with the adjacent nitrogen atom; R 3 is a 4-(2-alkoxy-2-phenylethyl)piperazinyl group (where the alkoxy group is a C 1-4 alkoxy group), a -NH(CH 2 ) n NH 2 group (wherein n is an integer of 2 to 10) or a 4-cinnamylpiperazinyl group.
Claim 4
Dependent Claim
135 words
A compound of claim 2 of formula (I) wherein R 1 is a hydrogen atom or a methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl or n-dodecyl group, R 2 has the same meaning as R 1 or is a cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group; a phenyl, naphthyl, o-, m- or p-chlorophenyl, p-bromophenyl, p-fluorophenyl, o-, m- or p-tolyl or 2,3-dimethylphenyl group; a benzyl, alpha-phenethyl, B-phenethyl, o-, m- or p-chlorobenzyl or p-fluorobenzyl group; or R 1 and R 2 form together with the adjacent N-atom a 1-pyrrolidinyl, piperidino, morpholino or 4-cinnamylpiperazinyl group; R 3 is a 4-(2-alkoxy-2-phenylethyl)piperazinyl group where the alkoxy group is a methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, n-pentoxy, n-hexoxy, n-heptoxy or n-octoxy group; or a 2-aminoethylamino, 3-aminopropylamino, 4-aminobutylamino, 5-aminopentylamino, 6-aminohexylamino, 8-amino- octylamino or 10-aminodecylamino group.
Claim 5
Dependent Claim
146 words
A process of preparing the compound of formula (I) of claim 1, 2 or 3 which comprises reacting a compound of formula (II): wherein R 1 is a hydrogen atom or a C 1-12 alkyl group; R 2 is a hydrogen atom, a C 1-12 alkyl group, a C 4-10 cycloalkyl group, an aryl group or an aralkyl group; and R1 and R 2 may be C 1-6 alkylene groups and linked directly or through an oxygen atom to form a 5- to 7- membered heterocyclic ring together with the adjacent' nitrogen atom; and X is a halogen atom with'a compound of formula (III): wherein R 3 is a group wherein R 4 is a C 1-8 alkyl group; a -NH(CH 2 ) n NH 2 group wherein n is an integer of 2 to 10; or a group or pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim
27 words
The process of claim 4, wherein the amount of the compound of formula (III) is at least 1 mol per mol of the compound of formula (II).
Claim 7
Dependent Claim
35 words
The process of claim 5, wherein the amount of the compound of formula (III) is about 1 to about 10 mols and preferably 1.0 to 5 mols per mol of the compound of formula (II).
Claim 8
Dependent Claim
32 words
7 . The process of claim 4, wherein the reaction between the compound of formula (II) and the compound of formula (III) is carried out in the presence of an acid acceptor.
Claim 9
Dependent Claim
19 words
The process of claim 7, wherein the acid acceptor is an alkali metal compound or an organic tertiary amine.
Claim 10
Dependent Claim
26 words
The process of claim 8, wherein the alkali metal compound is a hydroxide, a bicarbonate, a carbonate, a hydride or an alkoxide of an alkali metal.
Claim 11
Dependent Claim
28 words
The process of claim 7, wherein the amount of the acid acceptor is about 1 to about 10 equivalents for each mol of the compound of formula (III).
Claim 12
Dependent Claim
26 words
The process of claim 10, wherein the amount of the acid acceptor is 1 to 6 equivalents for each mol of the compound of formula (III).
Claim 13
Dependent Claim
30 words
The process of claim 4, wherein the reaction between the compound of formula (II) and the amine of formula (III) is carried out in the presence of a reaction medium.
Claim 14
Dependent Claim
26 words
The process of claim 12, wherein the reaction medium is a halogenated hydrocarbon, an alkanol, an ether, N,N-dimethylformamide, dimethyl sulfoxide, acetonitrile, water or a mixture thereof.
Claim 15
Dependent Claim
17 words
The process of claim 4, wherein the reaction temperature is about -30 °C to ahout 150 °C.
Claim 16
Dependent Claim
19 words
15 . The process of claim 14, wherein the reaction temperature is about 0 °C to about 30 °C.
Claim 17
Dependent Claim
146 words
A process of preparing the compound of formula (I) of claim 1, 2 or 3, which comprises reacting a compound of formula (IV): wherein R 3 is a group wherein R 4 is a C 1-8 alkyl group; a -NH(CH 2 ) n NH 2 group wherein n is an integer of 2 to 10; or a group; and X is a halogen atom, with an amine of formula (V): wherein R 1 is a hydrogen atom or a C 1-12 alkyl group; R2 is a hydrogen atom, a C 1-12 alkyl group, a C 4-10 cycloalkyl group, an aryl group or an aralkyl group; and R 1 and R2 may be C 1-6 alkylene groups and linked directly or through an oxygen atom to form a 5- to 7- membered heterocyclic ring together with the adjacent nitrogen ntom, or pharmaceutically acceptable acid addition salt thereof.
Claim 18
Dependent Claim
35 words
The process of claim 16, wherein the amount of the amine of formula (V) is at least 1 mol and preferably about 1 to about 20 mols per mol of the compound of formula (IV).
Claim 19
Dependent Claim
27 words
The process of claim 17, wherein the amount of the amine of formula (V) is 1.2 to 10 mols per mol of the compound of formula (IV).
Claim 20
Dependent Claim
30 words
The process of claim 16, wherein the reaction between the compound of formula (IV) and the amine of formula (V) is carried out in the presence of an acid acceptor.
Claim 21
Dependent Claim
19 words
The process of claim 19, wherein the acid acceptor is an alkali metal compound or an organic tertiary amine.
Claim 22
Dependent Claim
26 words
The process of claim 20, wherein the alkali metal compound is a hydroxide, a bicarbonate, a carbonate, a hydride or an alkoxide of an alkali metal.
Claim 23
Dependent Claim
28 words
The process of claim 19, wherein the amount of the acid acceptor is about 1 to about 10 equivalents for each mol of the amine of formula (V).
Claim 24
Dependent Claim
28 words
2 3. The process of claim 22, wherein the amount of the acid acceptor is 1 to 4 equivalents for each mol of the amine of formula (V).
Claim 25
Dependent Claim
30 words
The process of claim 16, wherein the reaction between the compound of formula (IV) and the amine of formula (V) is carried out in the presence of a reaction medium.
Claim 26
Dependent Claim
27 words
The process of claim 24, wherein the reaction medium is a halogenated hydrocarbon, an alkanol, an ether, N,N-dimethylformamide, dimethyl sulfoxide, . acetonitrile, water or a mixture thereof.
Claim 27
Dependent Claim
17 words
The process of claim 16, wherein the reaction temperature is about -30 °C to about 150 °C.
Claim 28
Dependent Claim
17 words
The process of claim 26, wherein the reaction temperature is about 0 °C to about 60 °C.
Claim 29
Dependent Claim
27 words
A compound of formula (II): wherein R 1 and R 2 have a meaning according to claim 1, 2 or 3 and X is a halogen atom.
Claim 30
Dependent Claim
16 words
A compound of claim 28 of formula (II) wherein X is a chlorine or bromine atom.
Claim 31
Dependent Claim
29 words
A compound of formula (IV): wherein X is a halogen atom and R 3 , R 4 and n have a meaning according to claim 1, 2 or 3.
Claim 32
Dependent Claim
16 words
A compound of claim 30 of formula (IV) wherein X is a chlorine or bromine atom.
Claim 33
Dependent Claim
22 words
A compound of formula (VI): wherein R 3 , R4 and n have a meaning according to claim 1, 2 or 3.
Claim 34
Dependent Claim
43 words
A process for preparing the compound of formula (II) of claim 28 or 29 which comprises reacting a compound of the following formula wherein R 1 and R 2 have a meaning according to claim 1, 2 or 3 with a halogenating agent.
Claim 35
Dependent Claim
57 words
A process of preparing the compound (VI) of claim 32 which comprises reacting 3,4-dihydro-4-oxo-6-quinazolinesulfonyl chloride or bromide with a compound of formula (III): wherein R 3 is a group wherein R 4 is a C 1-8 alkyl group; a -HN(CH 2 ) n NH 2 wherein n is an integer of 2 to 10 or a group.
Claim 36
Dependent Claim
23 words
The process of claim 34, wherein R 3 in formula (III) is a group wherein R 4 is a C 1-4 alkyl group.
Claim 37
Dependent Claim
17 words
The process of claim 34, wherein the reaction is carried out in the presence of a-reaction medium.
Claim 38
Dependent Claim
11 words
The process of claim 36, wherein the reaction medium is chloroform.
Claim 39
Dependent Claim
33 words
The process of claim 34, wherein the reaction is carried out in the presence of about 1 to about 5 mols of anhydrous potassium carbonate per mol of the 3,4-dihydro-4-oxo-quinazolinesulfonyl chloride or bromide.
Claim 40
Dependent Claim
18 words
The process of claim 34, wherein the reaction temperature ranges from about 10 °C to about 30 °C.
Claim 41
Dependent Claim
25 words
A process of preparing the compound IV of claim 30 which comprises reacting a compound of formula (VI) of claim 32 with a halogenating agent.
Claim 42
Dependent Claim
28 words
The process of claim 40, wherein the amount of the halogenating agent ranges from about 3 to about 30 mols per mol of the compound of formula (VI).
Claim 43
Dependent Claim
21 words
42 . The process of claim 40, wherein the reaction is carried out in the presence of an inert reaction medium.
Claim 44
Dependent Claim
18 words
The process of claim 40, wherein the reaction temperature ranges from about 20 °C to about 200 °C.
Claim 45
Dependent Claim
18 words
The process of claim 43, wherein the reaction temperature ranges from about 60 °C to about 150 °C.
Claim 46
Dependent Claim
18 words
The process of claim 44, wherein the reaction temperature ranges from about 70 °C to about 120 °C.
Claim 47
Dependent Claim
21 words
The process of claim 40, wherein the halogenating agent is thionyl chloride, phosphorus oxychloride, phosphorus trichloride, phosphorus tribromide and phosphorus pentachloride.
Claim 48
Dependent Claim
16 words
The process of claim 42, wherein the inert reaction medium is N,N-dimethylformamide, chloroform, benzene and toluene.
Claim 49
Dependent Claim
24 words
A therapeutical agent, characterized by a 6-quinazolinesulfonyl derivative of formula (I) according to claim 1, 2 or 3 as active ingredient and usual excipients.
Claim 50
Dependent Claim
9 words
Vasodilator and hypotensor as agent according to claim. 48.
References Cited (Backward Citations)
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