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US4331591A Expired / Lapsed US ⏱️ 0.0 years remaining

Chemical process for the production of α-aminophosphonic acids and peptide derivatives

Assignee: Novartis Corp
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Filing: 1979-10-01
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Granted: 1982-05-25
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Expires: 1999-10-01
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Abstract

Abstract The present invention provides a process for the production of physiologically-useful α-aminophosphonic acids and peptide derivatives of the formula: ##STR1## wherein R and R 1 may be the same or different and each can be hydrogen, deuterium or an optionally substituted lower alkyl group, lower alkenyl, lower alkynyl, cycloalkyl, aryl or heterocyclic radical containing one or more oxygen, nitrogen or sulphur atoms and which may be fused to an aromatic ring, a lower alkyl group substituted by a cycloalkyl radical, a lower alkyl group substituted by an aryl radical, a lower alkyl group substituted by a heterocyclic radical as defined above or R and R 1 together form a polymethylene chain optionally interrupted by an oxygen, nitrogen or sulphur atom, or R 1 represents, together with the C(R)--N< residue to which it is attached, the atoms required to complete a heterocyclic radical; and R 2 can be hydrogen, optionally substituted lower alkyl, cycloalkyl, aryl or lower alkyl substituted by a cycloalkyl radical, lower alkyl substituted by a heterocyclic radical containing one or more nitrogen atoms; by a heterocyclic radical containing one or more nitrogen atoms, or R 2 together with the C(H)--N residue to which it is attached, may represent the atoms required to complete a heterocyclic radical; and n is 0, 1, 2, 3 or 4; comprising oxidizing, using an oxidizing agent, a compound having the formula: ##STR2## wherein R, R 1 , R 2 and n have their previous significance, and Z is H or a protecting group usually used for an amino group; and then removing any protecting group.

Inventors

  • 👤 Eric K. Baylis

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 13:31
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3808; A; A61; A61P; A61P31/00; A61P31/04; C07K; C07K5/00; C07K5/04; C07K5/08; C07K5/0827; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 252 words
A process for the production of an α-aminophosphonic acid or a peptide derivative thereof of formula: ##STR6## wherein R and R 1 may be the same or different and each can be hydrogen, deuterium or an optionally substituted lower alkyl group, lower alkenyl, lower alkynyl, cycloalkyl, aryl or heterocyclic radical containing one or more oxygen, nitrogen or sulphur atoms and which may be fused to an aromatic ring, a lower alkyl group substituted by a cycloalkyl radical, a lower alkyl group substituted by an aryl radical, a lower alkyl group substituted by a heterocyclic radical as defined above or R and R 1 together form a polymethylene chain optionally interrupted by an oxygen, nitrogen or sulphur atom, or R 1 represents, together with the C(R)--N<residue to which it is attached, the atoms required to complete a heterocyclic radical; and R 2 can be hydrogen, optionally substituted lower alkyl, cycloalkyl, aryl or lower alkyl substituted by a cycloalkyl radical, lower alkyl substituted by a heterocyclic radical containing one or more nitrogen atoms; by a heterocyclic radical containing one or more nitrogen atoms, or R 2 together with the C(H)--N residue to which it is attached, may represent the atoms required to complete a heterocyclic radical; and n is 0, 1, 2, 3 or 4; comprising oxidising, using an oxidising agent, a compound having the formula: ##STR7## wherein R, R 1 , R 2 and n have their previous significance, and Z is H or a protecting group usually used for an amino group.
Claim 2
Dependent Claim 252 words
A process for the production of an α-aminophosphonic acid or a peptide derivative thereof of formula: ##STR6## wherein R and R 1 may be the same or different and each can be hydrogen, deuterium or an optionally substituted lower alkyl group, lower alkenyl, lower alkynyl, cycloalkyl, aryl or heterocyclic radical containing one or more oxygen, nitrogen or sulphur atoms and which may be fused to an aromatic ring, a lower alkyl group substituted by a cycloalkyl radical, a lower alkyl group substituted by an aryl radical, a lower alkyl group substituted by a heterocyclic radical as defined above or R and R 1 together form a polymethylene chain optionally interrupted by an oxygen, nitrogen or sulphur atom, or R 1 represents, together with the C(R)--N<residue to which it is attached, the atoms required to complete a heterocyclic radical; and R 2 can be hydrogen, optionally substituted lower alkyl, cycloalkyl, aryl or lower alkyl substituted by a cycloalkyl radical, lower alkyl substituted by a heterocyclic radical containing one or more nitrogen atoms; by a heterocyclic radical containing one or more nitrogen atoms, or R 2 together with the C(H)--N residue to which it is attached, may represent the atoms required to complete a heterocyclic radical; and n is 0, 1, 2, 3 or 4; comprising oxidising, using an oxidising agent, a compound having the formula: ##STR7## wherein R, R 1 , R 2 and n have their previous significance, and Z is H or a protecting group usually used for an amino group.
Claim 3
Dependent Claim 89 words
A process as claimed in claim 1 wherein the oxidising agent is a salt of a metal (capable of existing in higher and lower valency states) in its higher valency state in the presence of a hydroxylic solvent; an oxide of a metal or non-metal capable of releasing oxygen; an oxyacid (or a salt thereof) of a metal or non-metal, capable of releasing oxygen; an organic compound capable of releasing oxygen; a halogen or halo-organic compound in the presence of water; a direct source of oxygen; or a peroxide.
Claim 4
Dependent Claim 17 words
A process as claimed in claim 2 wherein the oxidising agent is cupric chloride or mercuric chloride.
Claim 5
Dependent Claim 14 words
A process as claimed in claim 2 wherein the oxidising agent is sulphur dioxide.
Claim 6
Dependent Claim 14 words
A process as claimed in claim 2 wherein the oxidising agent is bromine water.
Claim 7
Dependent Claim 14 words
A process as claimed in claim 2 wherein the oxidising agent is hydrogen peroxide.
Claim 8
Dependent Claim 18 words
A process as claimed in claim 1 wherein, in compounds of formula I and II, n is zero.
Claim 9
Dependent Claim 19 words
A process as claimed in claim 1 wherein, in the compounds of formula I and II, n is 1.
Claim 10
Dependent Claim 22 words
A process as claimed in claim 1 wherein, in the compounds of formula I and II, n is 2, 3 or 4.
Claim 11
Dependent Claim 19 words
A process as claimed in claim 1 wherein the compounds of formula I are α-aminophosphonic acids and dipeptide derivatives.
Claim 12
Dependent Claim 23 words
A process as claimed in claim 10 wherein the compound of formula I is 1-aminoethanephosphonic acid and peptide derivatives based on this acid.
Claim 13
Dependent Claim 10 words
A process according to claim 1, wherein Z is H.

References Cited (Backward Citations)

US2899455A Cited
US2952699A Cited
US3187035A Cited
US3277217A Cited
US3333030A Cited
US4016148A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-05-24 1985-11-23 1986-05-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-05-24 1989-11-23 1990-05-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-05-24 1993-11-23 1994-05-25 $7700.00 Window Closed / Lapsed

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