EP0035375A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Carbamic acid esters, their production and use
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1981-02-26
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Granted: —
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Expires: 2001-02-26
Abstract
Abstract New carbamic acid esters, inclusive of salts thereof, which have the formula: wherein n is zero or 1; R 1 and R 2 independently represent -H, -OCH 3 or -OCONHR 6 in which R 6 is C 8 - 26 aliphatic hydrocarbon residue provided that at least one of R 1 and R 2 is -OCONHR 6 ; and R 3 , R 4 and R 5 independently represent hydrogen or lower alkyl, or represents cyclic ammonio, exhibit inhibitory activity to nultiplication of tumor cells and antimicrobial activity.
Inventors
- 👤 Motoo Hozumi
- 👤 Hiroaki Nomura
- 👤 Yoshio Yoshioka
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 22:16
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6536; C07F9/6539; A; A01; A01N; A01N57/00; A01N57/10; C07F9/06; C07F9/08; C07F9/09; C07F9/091; C07F9/10; C07F9/553; C07F9/576; C07F9/58
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
132 words
A compound of the formula: wherein n is zero or 1; R 1 and R 2 independently represent -H, -OCH 3 or - OC O NH R 6 in which R 6 is C 8-26 alkyl, C 8-26 alkenyl or C 8-26 alkynyl, each of said groups being unsubstituted or substituted by hydroxyl, mercapto, amino, oxo, carbamoyl, carboxyl, halogen, C 3-7 cycloalkyl, phenyl or 2,3-dimethoxy-6-methyl-1,4-benzoquinon-5-yl, provided that at least one of R 1 and R 2 is - OC ONHR 6 ; and R 3 . R 4 and R independently represent hvdroaen or C 1-3 alkyl, or represents oxazolio, pyridinio, thiazolio, N-C 1-4 alkylpiperazinio or N-C 1-4 alkylmorpholinio, each of said groups being unsubstituted or substituted by C 1-4 alkyl, hydroxylethyl, amino, carbamoyl or ureido, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
132 words
A compound of the formula: wherein n is zero or 1; R 1 and R 2 independently represent -H, -OCH 3 or - OC O NH R 6 in which R 6 is C 8-26 alkyl, C 8-26 alkenyl or C 8-26 alkynyl, each of said groups being unsubstituted or substituted by hydroxyl, mercapto, amino, oxo, carbamoyl, carboxyl, halogen, C 3-7 cycloalkyl, phenyl or 2,3-dimethoxy-6-methyl-1,4-benzoquinon-5-yl, provided that at least one of R 1 and R 2 is - OC ONHR 6 ; and R 3 . R 4 and R independently represent hvdroaen or C 1-3 alkyl, or represents oxazolio, pyridinio, thiazolio, N-C 1-4 alkylpiperazinio or N-C 1-4 alkylmorpholinio, each of said groups being unsubstituted or substituted by C 1-4 alkyl, hydroxylethyl, amino, carbamoyl or ureido, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
25 words
.2. A compound according to Claim 1, wherein n is 1, R 1 is -OCONHR 6 and R 2 is -H or -OCH 3 .
Claim 4
Dependent Claim
13 words
.3. A compound according to Claim 2, wherein R 2 is H .
Claim 5
Dependent Claim
18 words
.4. A compound according to Claim 2, wherein R 6 is C 10-18 alkyl or C 10-18 alkenyl.
Claim 6
Dependent Claim
25 words
A compound according to Claim 1 , wherein R 3 , R 4 and R 5 are hydrogen or methyl, or is pyridinio or thiazolio.
Claim 7
Dependent Claim
11 words
The compound according to Claim 1, which is 3-(N-tetradecylcarbamoyloxy)-2-methoxypropyl 2-trimethylammonioethyl phosphate.
Claim 8
Dependent Claim
11 words
The compound according to Claim 1, which is 3-(N-tridecylcarbamoyloxy)-2-methoxypropyl 2-trimethylammonioethyl phosphate.
Claim 9
Dependent Claim
11 words
The compound according to Claim 1, which is 3-(N-octadecylcarbamoyloxy)-2-methoxypropyl 2-pyridinioethyl phosphate
Claim 10
Dependent Claim
11 words
The compound according to Claim 1, which is 3-(N-pentadecylcarbamoyloxy)-2-methoxypropyl 2-trimethylammonioethyl phosphate.
Claim 11
Dependent Claim
11 words
The compound according to Claim 1, which is 3-(N-8,11,14-heptadeca-trienylcarbamoyloxypropyl 2-trimethylammonioethyl phosphate.
Claim 12
Dependent Claim
21 words
A compound as claimed in any one of Claims 1 to 10 for use in therapeutical treatment of a warm-blooded animal.
Claim 13
Dependent Claim
35 words
A pharmaceutical composition which comprises, as an active ingredient, an effective amount of a compound as claimed in any one of Claims 1 to 10 in association with a pharmaceutically acceptable carrier or excipient therefor.
Claim 14
Independent Claim
169 words
A method for producing a compound of the formula: wherein n is zero or 1; R 1 and R 2 independently represent -H, -OCH 3 or -OCO N HR 6 in which R 6 is C 8-26 alkyl, C 8-26 alkenyl or C 8-26 alkynyl, each of said groups being unsubstituted or substituted by hydroxyl, mercapto, amino, oxo, carbamoyl, carboxyl, halogen, C 3-7 cycloalkyl, phenyl or 2,3-dimethoxy-6-methyl-l,4-benzoquinon-5-yl, provided that at least one of R 1 and R 2 is -OCONHR 6 ; and R 3 , R 4 and R 5 independently represent hydrogen or C 1-3 alkyl, or represents oxazolio, pyridinio, t h i azol i o , N - Cl-4 alkylpiperazinio or N-C 1-4 alkylmorpholinio, each of said groups being unsubstituted or substituted by C 1-4 alkyl, hydroxylethyl, amino, carbamoyl or ureido, characterized by reacting a compound of the formula: wherein Y is Cl, Br or I, and other symbols are as defined above, with a compound of the formula: wherein all symbols are as defined above.
Claim 15
Independent Claim
169 words
A method for producing a compound of the formula: wherein n is zero or 1; R 1 and R 2 independently represent -H, -OCH 3 or -OCO N HR 6 in which R 6 is C 8-26 alkyl, C 8-26 alkenyl or C 8-26 alkynyl, each of said groups being unsubstituted or substituted by hydroxyl, mercapto, amino, oxo, carbamoyl, carboxyl, halogen, C 3-7 cycloalkyl, phenyl or 2,3-dimethoxy-6-methyl-l,4-benzoquinon-5-yl, provided that at least one of R 1 and R 2 is -OCONHR 6 ; and R 3 , R 4 and R 5 independently represent hydrogen or C 1-3 alkyl, or represents oxazolio, pyridinio, t h i azol i o , N - Cl-4 alkylpiperazinio or N-C 1-4 alkylmorpholinio, each of said groups being unsubstituted or substituted by C 1-4 alkyl, hydroxylethyl, amino, carbamoyl or ureido, characterized by reacting a compound of the formula: wherein Y is Cl, Br or I, and other symbols are as defined above, with a compound of the formula: wherein all symbols are as defined above.
Claim 16
Independent Claim
172 words
A method for producing a compound of the formula: wherein n is zero or 1; R 1 and R 2 independently represent -H, -OCH 3 or -OCONHR 6 in which R 6 is C 8-26 alkyl, C 8-26 alkenyl or C 8-26 alkynyl, each of said groups being unsubstituted or substituted by hydroxyl, mercapto, - amino, oxo, carbamoyl, carboxyl, halogen, C 3-7 cycloalkyl, phenyl or 2,3-dimethoxy-6-methyl-l,4-benzoquinon-5-yl, provided that at least one of R 1 and R 2 is -OCONHR6; and R 3 , R 4 and R 5 independently represent hydrogen or C 1-3 alkyl, or - represents oxazolio, pyridinio, thiazolio, N-C 1-4 alkylpiperazinio or N-C l-4 alkylmorpholinio, each of said groups being unsubstituted or substituted by C 1-4 alkyl, hydroxylethyl, amino, carbamoyl or ureido, characterized by reacting a compound of the formula: or wherein all symbols are as defined above, with a compound of the formula: wherein R 6 is as defined above, or with phosgene and, then, with a compound of the formula: wherein R 6 is as defined above.
Claim 17
Independent Claim
172 words
A method for producing a compound of the formula: wherein n is zero or 1; R 1 and R 2 independently represent -H, -OCH 3 or -OCONHR 6 in which R 6 is C 8-26 alkyl, C 8-26 alkenyl or C 8-26 alkynyl, each of said groups being unsubstituted or substituted by hydroxyl, mercapto, - amino, oxo, carbamoyl, carboxyl, halogen, C 3-7 cycloalkyl, phenyl or 2,3-dimethoxy-6-methyl-l,4-benzoquinon-5-yl, provided that at least one of R 1 and R 2 is -OCONHR6; and R 3 , R 4 and R 5 independently represent hydrogen or C 1-3 alkyl, or - represents oxazolio, pyridinio, thiazolio, N-C 1-4 alkylpiperazinio or N-C l-4 alkylmorpholinio, each of said groups being unsubstituted or substituted by C 1-4 alkyl, hydroxylethyl, amino, carbamoyl or ureido, characterized by reacting a compound of the formula: or wherein all symbols are as defined above, with a compound of the formula: wherein R 6 is as defined above, or with phosgene and, then, with a compound of the formula: wherein R 6 is as defined above.
Claim 18
Independent Claim
167 words
A method for producing a compound of the formula: wherein n is zero or l; R 1 and R 2 independently represent -H, -OCH 3 or - OCONHR 6 in which R 6 is C 8-26 alkyl, C 8-26 alkenyl or C 8-26 alkynyl, each of said groups being unsubstituted or substituted by hydroxyl, mercapto, amino, oxo, carbamoyl, carboxyl, halogen, C 3-7 cycloalkyl, phenyl or 2,3-dimethoxy-6-methyl-1,4-benzoquinon-5-yl, provided that at least one of R 1 and R 2 is -OCONHR 6 ; and R 3 , R 4 and R independently represent hydrogen or C 1-3 alkyl, or represents oxazolio, pyridinio, t hi azolio, N-C 1-4 alkylpiperazinio or N-C 1-4 alkylmorpholinio, each of said groups being unsubstituted or substituted by C 1-4 alkyl, hydroxylethyl, amino, carbamoyl or ureido, characterized by reacting a compound of the formula: Wherein X is Cl or Br, and other symbols are as defined above, with a compound of the formula: wherein X - is an anion, and other symbols are as defined above.
Claim 19
Independent Claim
167 words
A method for producing a compound of the formula: wherein n is zero or l; R 1 and R 2 independently represent -H, -OCH 3 or - OCONHR 6 in which R 6 is C 8-26 alkyl, C 8-26 alkenyl or C 8-26 alkynyl, each of said groups being unsubstituted or substituted by hydroxyl, mercapto, amino, oxo, carbamoyl, carboxyl, halogen, C 3-7 cycloalkyl, phenyl or 2,3-dimethoxy-6-methyl-1,4-benzoquinon-5-yl, provided that at least one of R 1 and R 2 is -OCONHR 6 ; and R 3 , R 4 and R independently represent hydrogen or C 1-3 alkyl, or represents oxazolio, pyridinio, t hi azolio, N-C 1-4 alkylpiperazinio or N-C 1-4 alkylmorpholinio, each of said groups being unsubstituted or substituted by C 1-4 alkyl, hydroxylethyl, amino, carbamoyl or ureido, characterized by reacting a compound of the formula: Wherein X is Cl or Br, and other symbols are as defined above, with a compound of the formula: wherein X - is an anion, and other symbols are as defined above.
References Cited (Backward Citations)
GB2020663A
Cited
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