Title:
INHIBITORS OF COPPER-CONTAINING AMINE OXIDASES
Document Type and Number:
WIPO Patent Application WO2002002541
Kind Code:
A3
Abstract:
The present invention is directed to 1,3,4-oxadiazine compounds that function as inhibitors of copper-containg amine oxidases commonly known as semicarbazide-sensitive amine oxidases (SSAO), including the human SSAO known as Vascular Adhesion Protein-1 (VAP-1). These SSAO inhibitors have therapeutic utility as drugs to treat conditions and diseases including, but not limited to, a number of inflammatory conditions and diseases (in particular chronic inflammatory conditions such as chronic arthritis, inflammatory bowel diseases, and chronic skin dermatoses), diseases related to carbohydrate metabolism and to abberations in adipocyte differentiation or function and smooth muscle cell function, and vascular diseases. The compounds have the general formula (I): or a tautomer, isomer, hydrazino alcohol degradation product, or a pharmaceutically acceptable solvate, hydrate, or salt thereof, wherein R<1>, R<2>, R<3>, R<4>, R<5>,R<6>, R<7>, and R<8> are as defined her ein.
Inventors:
SMITH DAVID JOHN (FI)
JALKANEN MARKKU (FI)
FUELOEP FERENC (HU)
LAZAR LASZLO (HU)
SZAKONYI ZSOLT (HU)
BERNATH GABOR (HU)
JALKANEN MARKKU (FI)
FUELOEP FERENC (HU)
LAZAR LASZLO (HU)
SZAKONYI ZSOLT (HU)
BERNATH GABOR (HU)
Application Number:
PCT/FI2001/000637
Publication Date:
April 18, 2002
Filing Date:
July 04, 2001
Export Citation:
Assignee:
BIOTIE THERAPIES CORP (FI)
SMITH DAVID JOHN (FI)
JALKANEN MARKKU (FI)
FUELOEP FERENC (HU)
LAZAR LASZLO (HU)
SZAKONYI ZSOLT (HU)
BERNATH GABOR (HU)
SMITH DAVID JOHN (FI)
JALKANEN MARKKU (FI)
FUELOEP FERENC (HU)
LAZAR LASZLO (HU)
SZAKONYI ZSOLT (HU)
BERNATH GABOR (HU)
International Classes:
A61K31/00; A61K31/131; A61K31/14; A61K31/15; A61K31/40; A61K31/445; A61K31/472; A61K31/5395; C07D217/16; A61P1/04; A61P1/16; A61P3/00; A61P3/10; A61P9/00; A61P9/10; A61P11/06; A61P17/00; A61P19/02; A61P25/00; A61P29/00; A61P37/00; A61P43/00; C07B61/00; C07D273/04; C07D498/04; C07D498/10; (IPC1-7): C07D273/04; C07D498/10; C07D498/04; A61K31/5395; A61P43/00; A61P29/00; A61P1/04; A61P17/00
Domestic Patent References:
| WO1993023023A1 | 1993-11-25 |
Foreign References:
| US3377345A | 1968-04-09 |
Other References:
DATABASE STN INTERNATIONAL, CAPLUS [online] GRIFANTINI M ET AL: "Derivatives of N-amino-1-ephedrine and N-amino-d-pseudoephedrine having antidepressive activity.", XP002902241, retrieved from CAPLUS Database accession no. 1968:426896
DATABASE STN INTERNATIONAL, CAPLUS [online] TAKAHASHI H ET AL: "Synthesis of N-alkylaminoephedrines and their effect on bronchinal musculature.", XP002902242, retrieved from CAPLUS Database accession no. 1982:142348
TREPANIER D L ET AL: "Synthesis and pharmacological evaluation of some tetrahydrooxadiazinones and some dihydroaminooxadiazines.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 11, no. 2, 1968, pages 357 - 360, XP002902243
LIZCANO J M ET AL: "Inhibition of bovine lung semicarbazide-sensitive amine oxidase (SSAO) by some hydrazine derivatives.", BIOCHEMICAL PHARMACOLOGY, vol. 52, no. 2, 1996, pages 187 - 195, XP002902244
IOFFE B V ET AL: "Über eine neue Art von Ring-Ketten-Tautomerie und die einfachsten Tetrahydro-1,3,4-Oxadiazinderivate.", TETRAHEDRON LETTERS, vol. 8, no. 36, 1967, pages 3505 - 3508, XP002902245
POTEKHIN A A ET AL: "Ring-chain tautomerism of substituted hydrazones VII. * Substituted 4-tert-butylperhydro-1,3,4-oxadiazines.*", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, no. 11, 1973, pages 1321 - 1326, XP002902246
POTEKHIN A A ET AL: "Ring-chain tautomerism of substituted hydrazones II. * Derivatives of 1-hydrazino- and 1-(N-alkylhydrazino)-2-propanols.*", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 7, no. 3, 1971, pages 277 - 283, XP002902247
SCHMITZ E ET AL: "Versuche zur N-Aminierung von Alkaloiden.", LIEBIGS ANN. CHEM., 1983, pages 1043 - 1046, XP002902248
DATABASE STN INTERNATIONAL, CAPLUS [online] TAKAHASHI H ET AL: "Synthesis of N-alkylaminoephedrines and their effect on bronchinal musculature.", XP002902242, retrieved from CAPLUS Database accession no. 1982:142348
TREPANIER D L ET AL: "Synthesis and pharmacological evaluation of some tetrahydrooxadiazinones and some dihydroaminooxadiazines.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 11, no. 2, 1968, pages 357 - 360, XP002902243
LIZCANO J M ET AL: "Inhibition of bovine lung semicarbazide-sensitive amine oxidase (SSAO) by some hydrazine derivatives.", BIOCHEMICAL PHARMACOLOGY, vol. 52, no. 2, 1996, pages 187 - 195, XP002902244
IOFFE B V ET AL: "Über eine neue Art von Ring-Ketten-Tautomerie und die einfachsten Tetrahydro-1,3,4-Oxadiazinderivate.", TETRAHEDRON LETTERS, vol. 8, no. 36, 1967, pages 3505 - 3508, XP002902245
POTEKHIN A A ET AL: "Ring-chain tautomerism of substituted hydrazones VII. * Substituted 4-tert-butylperhydro-1,3,4-oxadiazines.*", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, no. 11, 1973, pages 1321 - 1326, XP002902246
POTEKHIN A A ET AL: "Ring-chain tautomerism of substituted hydrazones II. * Derivatives of 1-hydrazino- and 1-(N-alkylhydrazino)-2-propanols.*", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 7, no. 3, 1971, pages 277 - 283, XP002902247
SCHMITZ E ET AL: "Versuche zur N-Aminierung von Alkaloiden.", LIEBIGS ANN. CHEM., 1983, pages 1043 - 1046, XP002902248
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