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US4134918A
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Alpha-halomethyl derivatives of amines
Assignee: Merrell Toraude et Cie
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Filing: 1977-09-06
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Granted: 1979-01-16
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Expires: 1997-09-06
Abstract
Abstract Novel halomethyl derivatives of amines of the following general structure: ##STR1## WHEREIN Y is FCH 2 --, F 2 CH-- or F 3 C--; Z is β-methylthioethyl, β-benzylthioethyl, S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, γ-guanidinopropyl, or ##STR2## WHEREIN N IS 2 OR 3 AND R 1 is hydrogen or lower alkyl of from 1 to 4 carbon atoms with the proviso that when R 1 is other than hydrogen, n is 2; and each of R a and R b is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR3## wherein R 2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; with the provisos that when Z is β-benzylthioethyl or S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, R b is hydrogen, when Z is β-methylthioethyl, Y is other than F 3 C--, and when Z is ##STR4## EACH OF R a and R b can be the same or different; and pharmaceutically acceptable salts and individual optical isomers thereof.
Inventors
- 👤 Philippe Bey
- 👤 Michel Jung
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 08:33
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A61; A61P; A61P43/00; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/16
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
187 words
A compound of the formula ##STR66## wherein Y is FCH 2-- , F 2 CH--, or F 3 C--, Z is β-methylthioethyl, β-benzylthioethyl, S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, γ-guanidinopropyl or ##STR67## wherein n is the integer 2 or 3 and R 1 is hydrogen or a lower alkyl group of from 1 to 4 carbon atoms with the proviso that when R 1 is other than hydrogen, n is 2; each of R a and R b is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or the group ##STR68## wherein R 2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; with the provisos that when Z is β-benzylthioethyl or S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, R b is hydrogen, when Z is β-methylthioethyl, Y is other than F 3 C--, and when Z is ##STR69## each of R a and R b can be the same or different; and pharmaceutically acceptable salts and individual optical isomers thereof.
Claim 2
Dependent Claim
187 words
A compound of the formula ##STR66## wherein Y is FCH 2-- , F 2 CH--, or F 3 C--, Z is β-methylthioethyl, β-benzylthioethyl, S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, γ-guanidinopropyl or ##STR67## wherein n is the integer 2 or 3 and R 1 is hydrogen or a lower alkyl group of from 1 to 4 carbon atoms with the proviso that when R 1 is other than hydrogen, n is 2; each of R a and R b is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or the group ##STR68## wherein R 2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; with the provisos that when Z is β-benzylthioethyl or S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, R b is hydrogen, when Z is β-methylthioethyl, Y is other than F 3 C--, and when Z is ##STR69## each of R a and R b can be the same or different; and pharmaceutically acceptable salts and individual optical isomers thereof.
Claim 3
Dependent Claim
13 words
A compound of claim 1 wherein Z is β-methylthioethyl, S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, γ-guanidinopropyl or ##STR70##
Claim 4
Dependent Claim
15 words
A compound of claim 1 wherein each of R a and R b is hydrogen.
Claim 5
Dependent Claim
9 words
A compound of claim 1 wherein Z is ##STR71##
Claim 6
Dependent Claim
15 words
A compound of claim 4 wherein each of R a and R b is hydrogen.
Claim 7
Dependent Claim
12 words
A compound of claim 5 wherein R 1 is hydrogen or methyl.
Claim 8
Dependent Claim
15 words
A compound of claim 1 wherein Y is FCH 2 -- or F 2 CH--.
Claim 9
Dependent Claim
8 words
A compound of claim 5 which is 1-difluoromethyl-1,4-butanediamine.
Claim 10
Dependent Claim
8 words
A compound of claim 5 which is 1-difluoromethyl-1,4-pentanediamine.
Claim 11
Dependent Claim
157 words
A process for preparing a compound of claim 1 wherein Z is β-methylthioethyl, β-benzylthioethyl or ##STR72## and each of R a and R b is hydrogen which comprises reducing a ketone of the formula ##STR73## β-methylthioethyl or β-benzylthioethyl wherein m is the integer 2 or 3, the alkanoyl moiety has from 2 to 5 carbon atoms and is straight or branched, the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched and Y and R 1 have the meanings defined in claim 1 with the proviso that when Y is F 3 C--, Z' is other than β-methylthioethyl ##STR74## to the corresponding alcohol which is treated with one equivalent of an appropriate imide, 1.1 equivalents of an appropriate phosphine and 1.1 equivalents of diethyl azodicarboxylate in a suitable solvent at about 0° to 100° C for about 1/2 hour to 24 hours under an inert atmosphere followed by hydrolysis to the amine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-01-15 | 1982-07-17 | 1983-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-15 | 1986-07-17 | 1987-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-15 | 1990-07-17 | 1991-01-16 | $7700.00 | Window Closed / Lapsed |