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Patent · US6235912B1 · B1 · US

Sphingosine analogues

(11) Publication number
US6235912B1
(21) Application number
09/380,647
(22) Filing date
1998-03-12
(30) Priority date
1997-03-12
(43) Publication date
2001-05-22
(45) Date of grant
2001-05-22
(51) IPC
C07C 215/10; C07C 215/24; C07C 229/22; C07C 229/30; C07C 237/08; C07C 237/22; C07C 251/08; C07C 271/22; C07D 263/06; C07D 307/33
(52) CPC
  • C07D Heterocyclic compounds: 307/33, 263/06
  • C07C Acyclic or carbocyclic compounds: 215/10, 215/24, 229/22, 229/30, 237/08, 237/22, 251/08, 271/22
  • Y02P Climate change mitigation technologies in the production or processing of goods: 20/55
(73) Assignee
Takara Shuzo Co Ltd
(72) Inventors
Kazutoh Takesako; Toru Kurome; Naoyuki Awazu; Ikunoshin Kato
(54) Title
Sphingosine analogues
(57) Abstract

The present invention aims to provide a novel sphingosine analogue, which is useful as an intermediate for syntheses of novel lipid derivatives such as sphingolipid derivatives and the like that can regulate the effects of sphingolipid. The present invention relates to a sphingosine analogue represented by the general formula (I) described below. In the formula, as for Q 1, Q 2 and Q 3, Q 1 and Q 2, which are the same or different each other, are hydrogen, alkyl groups having 1-4 of carbon atoms, acyl groups having 2-5 of carbon atoms, or protecting groups of the amino group, and Q 3 is a hydrogen or a protecting group of the hydroxyl group; or Q 2 and Q 3 make up an isopropylidene group and Q 1 is a hydrogen or a protecting group of the amino group. Q 4 and Q 5, which are the same or different each other, are hydroxyl groups, acyl groups having 2-5 of carbon atoms, - O - Q 6, or hydrogen; or Q 4 and Q 5 make up a covalent bond. Q 6 is a protecting group of the hydroxyl group. X 1 is - COOH, - CONH 2, - CO - Q 7, - CH 2 OH, or - CH 2 O - Q 8. Q 7 is a protecting group of the carboxyl group, and Q 8 is a protecting group of the hydroxyl group.

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Claims (1)

  1. A sphingosine analogue represented by the following general formula (I): In the formula, as for Q 1, Q 2 and Q 3, Q 1 and Q 2, which are the same or different each other, are hydrogen, alkyl groups having 1-4 of carbon atoms, acyl groups having 2-5 of carbon atoms, or protecting groups of the amino group, and Q 3 is a hydrogen or a protecting group of the hydroxyl group; or Q 2 and Q 3 make up an isopropylidene group and Q 1 is a hydrogen or a protecting group of the amino group, Q 4 and Q 5, which are the same or different each other, are hydroxyl groups, acyl groups having 2-5 of carbon atoms, - O - Q 6, or hydrogen; or Q 4 and Q 5 make up a covalent bond, Q 6 is a protecting group of the hydroxyl group, X 1 is - COOH, - CONH 2, - CO - Q 7, - CH 2 OH, or - CH 2 O - Q 8, Q 7 is a protecting group of the carboxyl group, and Q 8 is a protecting group of the hydroxyl group.

Description

This application is a continuation of PCT/JP98/01038 Mar. 12, 1998.

The present invention relates to a novel sphingosine analogue, which is useful as an intermediate for syntheses of TKR1785's and their derivatives useful as drugs for the treatment of fungal infections, allergic diseases, etc., and also as an intermediate for syntheses of novel sphingolipid derivatives. The present invention also relates to a process for production of a novel sphingolipid.

Sphingosine is a compound having the chemical formula shown in the general formula described below, in which Y 1 is hydrogen. It is known that various sphingolipids having sphingosine as a constituent are widely distributed in the living body including on the surface of cell membranes of cells in the nervous system. Also we know glycosphingolipids binding one or several kinds of sugars as Y 1 via a glycoside bond to a ceramide having a fatty acid bound to the amino group of sphingosine via a peptide bond, and sphingophospholipids, including sphingomyelin, binding a phosphoric acid and a base such as choline or ethanolamine as Y 1 to the above-mentioned ceramide.

A sphingolipid is one of the lipids having important roles in the living body. We know a disease called lipidosis which is caused by accumulation of a specified sphingolipid in the body concomitant with the abnormalities in the metabolic pathways due to respiration deficiency and others.

Citations (2)

  • JPS62138497A
  • EP0897988A1
Record as JSON
{
  "publication_number": "US6235912B1",
  "country": "US",
  "kind": "B1",
  "title": "Sphingosine analogues",
  "abstract": "The present invention aims to provide a novel sphingosine analogue, which is useful as an intermediate for syntheses of novel lipid derivatives such as sphingolipid derivatives and the like that can regulate the effects of sphingolipid. The present invention relates to a sphingosine analogue represented by the general formula (I) described below. In the formula, as for Q 1, Q 2 and Q 3, Q 1 and Q 2, which are the same or different each other, are hydrogen, alkyl groups having 1-4 of carbon atoms, acyl groups having 2-5 of carbon atoms, or protecting groups of the amino group, and Q 3 is a hydrogen or a protecting group of the hydroxyl group; or Q 2 and Q 3 make up an isopropylidene group and Q 1 is a hydrogen or a protecting group of the amino group. Q 4 and Q 5, which are the same or different each other, are hydroxyl groups, acyl groups having 2-5 of carbon atoms, - O - Q 6, or hydrogen; or Q 4 and Q 5 make up a covalent bond. Q 6 is a protecting group of the hydroxyl group. X 1 is - COOH, - CONH 2, - CO - Q 7, - CH 2 OH, or - CH 2 O - Q 8. Q 7 is a protecting group of the carboxyl group, and Q 8 is a protecting group of the hydroxyl group.",
  "claims": [
    "1. A sphingosine analogue represented by the following general formula (I): In the formula, as for Q 1, Q 2 and Q 3, Q 1 and Q 2, which are the same or different each other, are hydrogen, alkyl groups having 1-4 of carbon atoms, acyl groups having 2-5 of carbon atoms, or protecting groups of the amino group, and Q 3 is a hydrogen or a protecting group of the hydroxyl group; or Q 2 and Q 3 make up an isopropylidene group and Q 1 is a hydrogen or a protecting group of the amino group, Q 4 and Q 5, which are the same or different each other, are hydroxyl groups, acyl groups having 2-5 of carbon atoms, - O - Q 6, or hydrogen; or Q 4 and Q 5 make up a covalent bond, Q 6 is a protecting group of the hydroxyl group, X 1 is - COOH, - CONH 2, - CO - Q 7, - CH 2 OH, or - CH 2 O - Q 8, Q 7 is a protecting group of the carboxyl group, and Q 8 is a protecting group of the hydroxyl group."
  ],
  "description_excerpt": "This application is a continuation of PCT/JP98/01038 Mar. 12, 1998.\n\nThe present invention relates to a novel sphingosine analogue, which is useful as an intermediate for syntheses of TKR1785's and their derivatives useful as drugs for the treatment of fungal infections, allergic diseases, etc., and also as an intermediate for syntheses of novel sphingolipid derivatives. The present invention also relates to a process for production of a novel sphingolipid.\n\nSphingosine is a compound having the chemical formula shown in the general formula described below, in which Y 1 is hydrogen. It is known that various sphingolipids having sphingosine as a constituent are widely distributed in the living body including on the surface of cell membranes of cells in the nervous system. Also we know glycosphingolipids binding one or several kinds of sugars as Y 1 via a glycoside bond to a ceramide having a fatty acid bound to the amino group of sphingosine via a peptide bond, and sphingophospholipids, including sphingomyelin, binding a phosphoric acid and a base such as choline or ethanolamine as Y 1 to the above-mentioned ceramide.\n\nA sphingolipid is one of the lipids having important roles in the living body. We know a disease called lipidosis which is caused by accumulation of a specified sphingolipid in the body concomitant with the abnormalities in the metabolic pathways due to respiration deficiency and others.",
  "cpc": [
    "C07D 307/33",
    "C07C 215/10",
    "C07C 215/24",
    "C07C 229/22",
    "C07C 229/30",
    "C07C 237/08",
    "C07C 237/22",
    "C07C 251/08",
    "C07C 271/22",
    "C07D 263/06",
    "Y02P 20/55"
  ],
  "ipc": [
    "C07C 215/10",
    "C07C 215/24",
    "C07C 229/22",
    "C07C 229/30",
    "C07C 237/08",
    "C07C 237/22",
    "C07C 251/08",
    "C07C 271/22",
    "C07D 263/06",
    "C07D 307/33"
  ],
  "assignees": [
    "Takara Shuzo Co Ltd"
  ],
  "inventors": [
    "Kazutoh Takesako",
    "Toru Kurome",
    "Naoyuki Awazu",
    "Ikunoshin Kato"
  ],
  "filing_date": "1998-03-12",
  "publication_date": "2001-05-22",
  "grant_date": "2001-05-22",
  "priority_date": "1997-03-12",
  "application_number": "US-38064799-A",
  "family_id": "26420164",
  "cited_by_count": 31,
  "citations": [
    "JPS62138497A",
    "EP0897988A1"
  ]
}

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