WO1999032428A3 - Synthesis of diamines - Google Patents

Synthesis of diamines Download PDF

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Publication number
WO1999032428A3
WO1999032428A3 PCT/EP1998/008415 EP9808415W WO9932428A3 WO 1999032428 A3 WO1999032428 A3 WO 1999032428A3 EP 9808415 W EP9808415 W EP 9808415W WO 9932428 A3 WO9932428 A3 WO 9932428A3
Authority
WO
WIPO (PCT)
Prior art keywords
resin
diamine
bound
produce
solid phase
Prior art date
Application number
PCT/EP1998/008415
Other languages
French (fr)
Other versions
WO1999032428A8 (en
WO1999032428A2 (en
Inventor
Sandor Pongor
Sotir Zahariev
Corrado Guarnaccia
Original Assignee
Int Centre Genetic Eng & Bio
Sandor Pongor
Sotir Zahariev
Corrado Guarnaccia
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Int Centre Genetic Eng & Bio, Sandor Pongor, Sotir Zahariev, Corrado Guarnaccia filed Critical Int Centre Genetic Eng & Bio
Publication of WO1999032428A2 publication Critical patent/WO1999032428A2/en
Publication of WO1999032428A3 publication Critical patent/WO1999032428A3/en
Publication of WO1999032428A8 publication Critical patent/WO1999032428A8/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B43/00—Formation or introduction of functional groups containing nitrogen
    • C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/57527—Calcitonin gene related peptide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • C07K14/70—Enkephalins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Endocrinology (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)

Abstract

A solid phase method for producing a compound comprising an unsubstituted or substituted diamine moiety, which method comprises: (i) reacting an N-protected amino aldehyde with an amino group attached to a solid resin to produce a resin-bound enamine product; and (ii) reducing the enamine product to produce a resin-bound N-protected diamine. The resin bound diamine may be further modified for example by further protection, reaction with an amino acid or by carrying out solid phase peptide synthesis to provide a peptide bonded at its C-terminus to a diamine moiety.
PCT/EP1998/008415 1997-12-22 1998-12-22 Synthesis of diamines WO1999032428A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9727123.3 1997-12-22
GBGB9727123.3A GB9727123D0 (en) 1997-12-22 1997-12-22 Synthesis of diamines

Publications (3)

Publication Number Publication Date
WO1999032428A2 WO1999032428A2 (en) 1999-07-01
WO1999032428A3 true WO1999032428A3 (en) 1999-09-10
WO1999032428A8 WO1999032428A8 (en) 1999-10-21

Family

ID=10824077

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/008415 WO1999032428A2 (en) 1997-12-22 1998-12-22 Synthesis of diamines

Country Status (2)

Country Link
GB (1) GB9727123D0 (en)
WO (1) WO1999032428A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1581400A (en) 1999-12-22 2001-07-03 Om Pharma Acyl pseudopeptides bearing a functionalised auxiliary spacer
WO2002088298A1 (en) 2001-04-27 2002-11-07 The Procter & Gamble Company Compounds, compositions, and methods for controlling biofilms
CN110343146B (en) * 2019-07-12 2022-09-30 上海应用技术大学 Hypsizygus marmoreus flavor-developing peptide and preparation method and application thereof

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2058077A (en) * 1979-06-08 1981-04-08 Szelke M Enkephalin analogues
EP0144290A2 (en) * 1983-12-01 1985-06-12 Ciba-Geigy Ag Substituted ethylenediamine derivatives
EP0209379A2 (en) * 1985-07-18 1987-01-21 The Queen's University of Belfast Solid phase peptide synthesis
EP0257742A2 (en) * 1986-06-27 1988-03-02 The Administrators of The Tulane Educational Fund Method of synthesizing a peptide containing a non-peptide bond
EP0264802A2 (en) * 1986-10-21 1988-04-27 Hoechst Aktiengesellschaft Synthesis of peptide-aminoalkyl amides and peptide hydrazides by the solid phase method
EP0347802A2 (en) * 1988-06-20 1989-12-27 Merrell Dow Pharmaceuticals Inc. Neurokinin A antagonists
EP0475184A1 (en) * 1990-08-30 1992-03-18 Hoechst Aktiengesellschaft Process for the production of peptides by solid phase synthesis
WO1995029189A1 (en) * 1994-04-26 1995-11-02 Selectide Corporation FACTOR Xa INHIBITORS

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2058077A (en) * 1979-06-08 1981-04-08 Szelke M Enkephalin analogues
EP0144290A2 (en) * 1983-12-01 1985-06-12 Ciba-Geigy Ag Substituted ethylenediamine derivatives
EP0209379A2 (en) * 1985-07-18 1987-01-21 The Queen's University of Belfast Solid phase peptide synthesis
EP0257742A2 (en) * 1986-06-27 1988-03-02 The Administrators of The Tulane Educational Fund Method of synthesizing a peptide containing a non-peptide bond
EP0264802A2 (en) * 1986-10-21 1988-04-27 Hoechst Aktiengesellschaft Synthesis of peptide-aminoalkyl amides and peptide hydrazides by the solid phase method
EP0347802A2 (en) * 1988-06-20 1989-12-27 Merrell Dow Pharmaceuticals Inc. Neurokinin A antagonists
EP0475184A1 (en) * 1990-08-30 1992-03-18 Hoechst Aktiengesellschaft Process for the production of peptides by solid phase synthesis
WO1995029189A1 (en) * 1994-04-26 1995-11-02 Selectide Corporation FACTOR Xa INHIBITORS

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WENG C. CHAN ET AL.: "Reductive alkylation of 9-Amino-xanthen-3-yloxymethyloly(styrene)", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS., 1995, LETCHWORTH GB, pages 1475 - 1477, XP002099378 *

Also Published As

Publication number Publication date
GB9727123D0 (en) 1998-02-25
WO1999032428A8 (en) 1999-10-21
WO1999032428A2 (en) 1999-07-01

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