Patent EP0318860A2 successfully refreshed from Google Patents.
EP0318860A2
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Substituted alkylamine derivatives
Assignee: MSD KK
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Filing: 1988-11-25
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Granted: —
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Expires: 2008-11-25
Abstract
Abstract A substituted alkylamine derivative represented by the general formula wherein A represents a methine group, a nitrogen atom, an oxygen atom or a sulfur atom; Q represents a group which may contain one or two hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms and forms a 5- or 6-membered aromatic ring together with the adjacent carbon atoms and A (the aromatic ring may contain one substituent, or two identical or different substituents, selected from the class consisting of halogen atoms, hydroxyl groups, lower alkyl groups and lower alkoxy groups); X and Y may be identical or different and each represents an oxygen atom, a sulfur atom, a carbonyl group, a group of the formula -CHR a- in which R a represents a hydrogen atom or a lower alkyl group, or a group of the formula -NR b- in which R b represents a hydrogen atom or a lower alkyl group, or when taken together, X and Y represent a vinylene or ethynylene group; R 1 represents a lower alkenyl group which may be substituted, a cycloalkenyl group which may be substituted, a lower alkynyl group which may be substituted, an aryl group which may be substituted, or a heterocyclic group which may be substituted; R 2 represents a hydrogen atom or a lower alkyl group; R 3 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group; R 4 and R 5 may be identical or different and each represents a hydrogen atom or a halogen atom; and R 6 represents an acyclic hydrocarbon group which may be substituted (which may contain 1 or 2 unsaturated bonds selected from double and triple bonds); a cycloalkyl group which may be substituted, or a phenyl group which may be substituted; provided that when either one of X and Y represents an oxygen or sulfur atom, or the group -NR b- in which R b is as defined above, the other represents a carbonyl group or the group -CHR a- in which R a is as defined above, and a nontoxic salt thereof. The said compound is useful as pharmaceuticals, particularly for the treatment and prevention of hypercholesterolemia, hyperlipemia and arteriosclerosis.
Inventors
- 👤 Hiroshi Takezawa
- 👤 Masahiro Hayashi
- 👤 Yoshikazu Iwasawa
- 👤 Masaaki Hosoi
- 👤 Yoshiaki Iida
- 👤 Yoshimi Tsuchiya
- 👤 Masahiro Horie
- 👤 Toshio Kamei
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-01 22:06
CPC Classifications
C; C07; C07D; C07D333/00; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C07C; C07C211/00; C07C211/01; C07C211/26; C07C211/27; C07C211/30; C07C211/43; C07C211/44; C07C211/45; C07C211/46; C07C211/49; C07C217/00; C07C217/02; C07C217/48; C07C217/54; C07C217/56; C07C217/58; C07C233/00; C07C233/01; C07C233/16; C07C233/17; C07C233/20; C07C237/00; C07C237/28; C07C237/40; C07C255/00; C07C255/49; C07C255/54; C07C323/00; C07C323/23; C07C323/31; C07C323/32; C07D213/36; C07D213/38; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D215/00; C07D215/02; C07D215/12; C07D215/14; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D261/00; C07D261/02; C07D261/06; C07D261/08; C07D263/00; C07D263/02; C07D263/30; C07D263/32; C07D277/00; C07D277/02; C07D277/20; C07D277/22; C07D277/24; C07D277/28; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07D307/56; C07D307/68; C07D307/77; C07D307/78; C07D307/79; C07D307/80; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/16; C07D417/00; C07D417/02; C07D417/12
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
513 words
A process for producing a substituted alkylamine derivative of the general formula wherein A represents a methine group, a nitrogen atom, an oxygen atom or a sulfur atom; Q represents a group which may contain one or two hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms and forms a 5- or 6-membered aromatic ring together with the adjacent carbon atoms and A (the aromatic ring may contain one substituent, or two identical or different substituents, selected from the class consisting of halogen atoms, hydroxyl groups, lower alkyl groups and lower alkoxy groups); X and Y may be identical or different and each represents an oxygen atom, a sulfur atom, a carbonyl group, a group of the formula -CHR a- in which R a represents a hydrogen atom or a lower alkyl group, or a group of the formula -NR b- in which R b represents a hydrogen atom or a lower alkyl group, or when taken together, X and Y represent a vinylene or ethynylene group; R 1 represents a lower alkenyl group which may be substituted, a cycloalkenyl group which may be substituted, a lower alkynyl group which may be substituted, an aryl group which may be substituted, or a heterocyclic group which may be substituted; R 2 represents a hydrogen atom or a lower alkyl group; R 3 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group; R 4 and R 5 may be identical or different and each represents a hydrogen atom or a halogen atom; and R 6 represents an acyclic hydrocarbon group which may be substituted (which may contain 1 or 2 unsaturated bonds selected from double and triple bonds); a cycloalkyl group which may be substituted, or a phenyl group which may be substituted; provided that when either one of X and Y represents an oxygen or sulfur atom, or the group -NR b- in which R b is as defined above, the other represents a carbonyl group or the group -CHR a- in which R a is as defined above, and a nontoxic salt thereof, which comprises (a) reacting a substituted amine derivative represented by the general formula wherein A, Q, X, Y, R 1 , R 2 and R 3 are as defined above, or its properly protected derivative with a compound represented by the general formula wherein Z represents a leaving group, and R 4 , R 5 and R 6 are as defined above, or its properly protected derivative, and thereafter, as required, removing the protective group, or (b) reacting a compound represented by the general formula wherein A, Q, X, Y, R 1 , R 2 and Z are as defined above, or its properly protected derivative with a substituted amine represented by the general formula wherein R 3 , R 4 , R 5 and R 6 are as defined above, o rits properly protected derivative, and thereafter, as required, removing the protective group, and, as required, converting the resulting compound into a nontoxic salt.
Claim 2
Dependent Claim
513 words
A process for producing a substituted alkylamine derivative of the general formula wherein A represents a methine group, a nitrogen atom, an oxygen atom or a sulfur atom; Q represents a group which may contain one or two hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms and forms a 5- or 6-membered aromatic ring together with the adjacent carbon atoms and A (the aromatic ring may contain one substituent, or two identical or different substituents, selected from the class consisting of halogen atoms, hydroxyl groups, lower alkyl groups and lower alkoxy groups); X and Y may be identical or different and each represents an oxygen atom, a sulfur atom, a carbonyl group, a group of the formula -CHR a- in which R a represents a hydrogen atom or a lower alkyl group, or a group of the formula -NR b- in which R b represents a hydrogen atom or a lower alkyl group, or when taken together, X and Y represent a vinylene or ethynylene group; R 1 represents a lower alkenyl group which may be substituted, a cycloalkenyl group which may be substituted, a lower alkynyl group which may be substituted, an aryl group which may be substituted, or a heterocyclic group which may be substituted; R 2 represents a hydrogen atom or a lower alkyl group; R 3 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group; R 4 and R 5 may be identical or different and each represents a hydrogen atom or a halogen atom; and R 6 represents an acyclic hydrocarbon group which may be substituted (which may contain 1 or 2 unsaturated bonds selected from double and triple bonds); a cycloalkyl group which may be substituted, or a phenyl group which may be substituted; provided that when either one of X and Y represents an oxygen or sulfur atom, or the group -NR b- in which R b is as defined above, the other represents a carbonyl group or the group -CHR a- in which R a is as defined above, and a nontoxic salt thereof, which comprises (a) reacting a substituted amine derivative represented by the general formula wherein A, Q, X, Y, R 1 , R 2 and R 3 are as defined above, or its properly protected derivative with a compound represented by the general formula wherein Z represents a leaving group, and R 4 , R 5 and R 6 are as defined above, or its properly protected derivative, and thereafter, as required, removing the protective group, or (b) reacting a compound represented by the general formula wherein A, Q, X, Y, R 1 , R 2 and Z are as defined above, or its properly protected derivative with a substituted amine represented by the general formula wherein R 3 , R 4 , R 5 and R 6 are as defined above, o rits properly protected derivative, and thereafter, as required, removing the protective group, and, as required, converting the resulting compound into a nontoxic salt.
Claim 3
Dependent Claim
142 words
A process for producing a substituted alkylamine derivative represented by the general formula wherein A, Q, X, Y, R 1 , R 2 , R 4 , R 5 and R 6 are as defined in claim 1, and R3 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group, and its nontoxic salt, which comprises reacting a substituted alkylamine derivative represented by the general formula wherein A, Q, X, Y, R 1 , R 2 , R 4 , R 5 and R 6 are as defined above, or its properly protected compound with a compound represented by the general formula Z-R3 [VI] wherein Z represents a leaving group and R 3 is as defined above, then, as required, removing the protective group, and as required, converting the resulting compound into a nontoxic salt.
Claim 4
Dependent Claim
195 words
A process for producing a substituted alkylamine derivative represented by the general formula wherein A, Q, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in claim 1, X a represents a carbonyl group or a group of the formula -CHR a - in which R a represents a hydrogen atom or a lower alkyl group, and Y a represents an oxygen or sulfur atom or a group of the formula -NR b- in which R b represents a hydrogen atom or a lower alkyl group, or its nontoxic salt, which comprises reacting a compound represented by the general formua R 1 -X a -Z [VII] wherein Z represents a leaving group and R 1 and X a are as defined above, or its properly proteced derivative with a substituted amine derivative represented by the general formula wherein A, Q, R 2 , R 3 , R 4 , R 5 , R 6 and Y a are as defined, or its properly protected compound, then, as required, removing the protective group, and then, as required, converting the resulting compound into a nontoxic salt.
Claim 5
Dependent Claim
195 words
A process for producing a substituted alkylamine derivative represented by the general formula in which A, Q, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in claim 1, X b represents an oxygen or sulfur atom, or a group of the formula -NR b- in which R b represents a hydrogen atom or a lower alkyl group, and Y b represents a carbonyl group or a group of the formula -CHR a - in which R a represents a hydrogen atom or a lower alkyl group, and its nontoxic salt, which comprises reacting a compound represented by the general formula R1-X b -H [IX] wherein R 1 and X b are as defined above, or its properly protected derivative with a substituted amine derivative represented by the general formula wherein A, Q, R 2 , R 3 , R 4 , R S , R 6 and Y b are as defined above, and Z represents a leaving group, or its properly protected compound, and, as required, removing the protecting group, and then, as required, converting the resulting compound into a nontoxic salt.
Claim 6
Dependent Claim
228 words
The process of claims 1 to 4 for the production of compounds in which R' represents an aryl or heterocyclic group which may be substituted; X represents a methylene group and Y represents an oxygen atom or an imino group, or X and Y, taken together, represent an ethylene group or an (E)-vinylene group; the aromatic ring of the formula is a benzene, furan, thiophene, oxazole, isoxazole, thiazole, pyridine or pyrimidine ring; R 2 represents a hydrogen atom; R 3 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, or a cycloalkyl group having 3 to 5 carbon atoms; R" and R 5 each represent a hydrogen atom, and the double bond formed by the two carbon atoms to which they are bonded is of a trans-form (E-form); and R 6 is a group of the formula -CH=CH-R 6 in which R° represents an alkyl or alkenyl group having 3 to 6 carbon atoms which may be substituted by one alkoxy group having 1 to 4 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms which may be substituted by 1 or 2 alkyl groups having 1 to 4 carbon atoms, or a group of the formula -C≡C-R c in which R° is as defined above.
Claim 7
Dependent Claim
75 words
The process of claim 5 for the production of compounds in which R 1 is an aryl group or an aromatic heterocyclic group, which may have one substituent, or two identical or different substituents, selected from the group consisting of halogen atoms and cyano, formyl, hydroxymethyl, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower alkenyloxy, phenyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrrolyl, imidazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl, 1,3,4-oxadiazolyl and 1,3,4-thiadiazolyl groups.
Claim 8
Dependent Claim
41 words
The process of claim 6 for the production of compounds in which the aromatic heterocyclic group is a 5- to 12-membered aromatic heterocyclic group containing 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms.
Claim 9
Dependent Claim
95 words
The process of claim 5 for the production of compounds in which R 1 is a phenyl, naphthyl, furyl, thienyl, pyridyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl or benzofurazanyl group which may contain one substituent, or identical or different two substituents, selected from the class consisting of halogen atoms and hydroxyl, cyano, formyl, hydroxymethyl, C 1 -C 3 alkyl, C 3 -C 5 alkenyl, C 3 -C 5 alkynyl, C 1 -C 3 alkoxy, C 3 -C 5 alkenyloxy, phenyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, pyrrolyl and imidazolyl groups.
Claim 10
Dependent Claim
27 words
The process of claim 5 for the production of compounds in which R 1 is a 2-methylphenyl, 2-fluorophenyl, 3-cyanophenyl, 3-(2-furyl)phenyl, 3-(2-thienyl)phenyl, 3-(5-oxazolyl)phenyl, 3-(1-pyrrolyl)-phenyl, 3-(1-imidazolyl)phenyl or 3-(5-thiazolyl)phenyl group.
Claim 11
Dependent Claim
100 words
The process of claims 1 to 4 for the production of compounds in which R 3 represents an alkyl group having 1 to 3 carbon atoms, an allyl group, a propargyl group or a cyclopropyl group; and R 6 represents a group of the formula in which R d represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and R e and R f may be identical or different and each represents a methyl or ethyl group, or taken together, they may represents a cyclopropyl group.
Claim 12
Dependent Claim
21 words
The process of claim 10 for the production of compounds in which R 3 represents a methyl, ethyl or propyl group.
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JPS5632440A
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JPS62201850A
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JPH0451986A
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