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IFI Claims Patent Services
Full Record
| Title: |
BIS(AMINOMETHYL)PHOSPHINIC ACID DERIVATIVES AND PROCESS FOR
THE PREPARATION OF BIS(AMINOMETHYL)PHOSPHINIC ACID
DERIVATIVES |
| Inventor(s): |
Budt Karl-Heinz,
DE
Peyman Anuschirwan, DE
Spanig Jorg, DE |
| Patent
Assignee(s): |
Hoechst AG
DE |
| Patent
Number: |
US
5608098 |
| Patent
Date: |
19970304 |
| Application
Number: |
US
525787 |
| Application
Date: |
19950928 |
| Exemplary
Claim(s) |
1. A process for the
preparation of compounds of the formula
VI
R4-NH-CH(-R2)-P(=O)(-O-R5)-CH(-R3)-NH-R4 (IV)
in which R2
and R3, independently of one another, are
hydrogen,
(C1-C18)-alkyl, (C2-C18)-alkenyl, (C2-C18)-alkynyl,
where alkyl, alkenyl and alkynyl are unsubstituted or substituted
one or more times by fluorine, chlorine, bromine, COOH, oxo, NO2,
NH2, NHC(O)-(C1-C6)-alkyl, NHC(O)-(C6-C12)-aryl, CN, OH, CHO,
CH-((C1C6)-alkoxy)2, SO3H, C(O)-O-(C1-C6)-alkyl,
C(O)-O-(C6-C12)-aryl, C(O)-(C1-C6)-alkyl, C(O)-(C6-C12)-aryl,
O-C(O)-(C1-C6)-alkyl, OC(O)-(C6-C12)-aryl, (C1-C6)-alkoxy; are
(C6-C12)-aryl, (C7-C22)arylalkyl, where aryl is unsubstituted or
substituted one or more times by fluorine, chlorine, bromine, NO2,
NH2, NHC(O)-(C1-C6)alkyl, NHC(O)-(C6-C12)-aryl, CN, OH, COOH,
(C1-C6)-alkyl, (C1C6)-alkoxy, C(O)-O-(C1-C6)-alkyl,
C(O)-O-(C6-C12)-aryl, C(O)-(C1C6)-alkyl, C(O)-(C6-C12)-aryl,
O-C(O)-(C1-C6)-alkyl, O-C(O)-(C6C12)-aryl; or are P(O)(OH)2,
P(O)(OR23)2, where R23 independently of one another is
(C1-C6)-alkyl, (C6-C12)-aryl or (C7-C13)arylalkyl and where aryl is
unsubstituted or substituted one or more times by fluorine,
chlorine, bromine, NO2, CN, OH, COOH, (C1-C6)-alkyl, (C1-C6)-alkoxy,
C(O)-O-(C1-C6)-alkyl, C(O)-O-(C6C12)-aryl, C(O)-(C1-C6)-alkyl,
C(O)-(C6-C12)-aryl, O-C(O)-(C1C6)-alkyl or O-C(O)-(C6-C12)-aryl,
where R2 and R3 are not simultaneously hydrogen; R4 is a protective
group for the amino function and R5 is (C1-C18)-alkyl,
(C2-C18)-alkenyl, (C2-C18)-alkynyl, (C6C12)-aryl,
(C7-C20)-arylalkyl, where alkyl, alkenyl, alkynyl and aryl are
unsubstituted or substituted one or more times by fluorine,
chlorine, bromine, oxo, NO2, NH2 or protected form, CN, OH, COOH,
(C1-C6)-alkyl, (C1-C6)-alkoxy, C(O)-O-(C1-C6)alkyl,
C(O)-O-(C6-C12)-aryl, C(O)-(C1-C6)-alkyl, C(O)-(C6-C12)aryl,
O-C(O)-(C1-C6)-alkyl, O-C(O)-(C6-C12)-aryl, which comprises
converting a compound of the formula IV
R4-NH-CH(-R6)-P(=O)(-O-R5)-CH(-R7)-NH-R4 (IV)
in which R4 and R5
have the abovementioned meaning and R6 and R7
independently of
one another are H, Cl or Br, where not both radicals are
simultaneously hydrogen a) by reaction with a base to a compound of
the formula Va or Vb R4-N=CH-P(=O)(-O-R5)-CH=N-R4
(Va)
R4-N=CH-P(=O)(-O-R5)-CH2-NH-R4 (Vb)
where R4 and R5 have
the abovementioned meanings and for the
preparation of the
compound VI, a compound of the formula Va or Vb is reacted with
carbon nucleophiles; or b) the compound of the formula VI is
prepared by direct reaction of a compound of the formula IV with
R22Cu(CN)Li2, R2Li, R2MgX, R2ZnX, R22Zn, R24-nTiR22n (n<4),
P(O-R23)3, where R2 has the abovementioned meaning; R22 is
N-((C1-C6)-alkyl)2, O-(C1-C6)alkyl, O-(C6-C12)-aryl, where aryl is
unsubstituted or substituted by fluorine, chlorine, bromine, NO2,
NH2 or protected form, CN, OH, COOH, C(O)-O-(C1-C6)-alkyl,
(C1-C6)alkyl, (C1-C6)-alkoxy, or is a tartaric acid derivative; and,
R23 is (C1-C6)-alkyl (C6-C12)-aryl, (C7-C13)-arylalkyl, where aryl
is unsubstituted or substituted one or more times by fluorine,
chlorine, bromine, NO2, CN, OH, COOH, (C1-C6)-alkyl, (C1-C6)-alkoxy,
C(O)-O-(C1-C6)-alkyl, C(O)-(C1-C6)-alkyl, OC(O)-(C1-C6)-alkyl, and X
is a leaving group. |
| Main US
Classification |
558145000 |
| Secondary US
Classification |
558155000
558158000
558159000 |
| Main
International Classification |
C07F-009/30 |
| Secondary
International Classification |
C07F-009/32
C07F-009/38
C07F-009/40 |
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25.12.2021