Title:
PYRROLIDINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF NEURAMINIDASES
Document Type and Number:
WIPO Patent Application WO2001028996
Kind Code:
A3
Abstract:
Disclosed are compounds of the formula:which are useful for inhibiting neuraminidases from disease-causing microorganisms, especially, influenza neuraminidase. Also disclosed are compositions and methods for preventing and treating diseases caused by microorganisms having a neuraminidase, processes for preparing the compounds and synthetic intermediates used in these processes.
Inventors:
MARING CLARENCE J (US)
GIRANDA VINCENT L (US)
KEMPF DALE J (US)
STOLL VINCENT S (US)
SUN MINGHUA (US)
ZHAO CHEN (US)
GU YU GUI (US)
HANESSIAN STEPHEN (CA)
WANG GARY T (US)
KRUEGER ALLAN C (US)
CHEN HUI-JU (US)
CHEN YUANWEI (US)
DEGOEY DAVID A (US)
FLOSI WILLIAM J (US)
GRAMPOVNIK DAVID J (US)
KATI WARREN M (US)
KENNEDY APRIL L (US)
KLEIN LARRY L (US)
LIN ZHEN (US)
MADIGAN DAROLD L (US)
GIRANDA VINCENT L (US)
KEMPF DALE J (US)
STOLL VINCENT S (US)
SUN MINGHUA (US)
ZHAO CHEN (US)
GU YU GUI (US)
HANESSIAN STEPHEN (CA)
WANG GARY T (US)
KRUEGER ALLAN C (US)
CHEN HUI-JU (US)
CHEN YUANWEI (US)
DEGOEY DAVID A (US)
FLOSI WILLIAM J (US)
GRAMPOVNIK DAVID J (US)
KATI WARREN M (US)
KENNEDY APRIL L (US)
KLEIN LARRY L (US)
LIN ZHEN (US)
MADIGAN DAROLD L (US)
Application Number:
PCT/US2000/027910
Publication Date:
November 29, 2001
Filing Date:
October 10, 2000
Export Citation:
Assignee:
ABBOTT LAB (US)
MARING CLARENCE J (US)
GIRANDA VINCENT L (US)
KEMPF DALE J (US)
STOLL VINCENT S (US)
SUN MINGHUA (US)
ZHAO CHEN (US)
GU YU GUI (US)
HANESSIAN STEPHEN (CA)
WANG GARY T (US)
KRUEGER ALLAN C (US)
CHEN HUI-JU (US)
CHEN YUANWEI (US)
DEGOEY DAVID A (US)
FLOSI WILLIAM J (US)
GRAMPOVNIK DAVID J (US)
KATI WARREN M (US)
KENNEDY APRIL L (US)
KLEIN LARRY L (US)
LIN ZHEN (US)
MADIGAN DAROLD L (US)
MARING CLARENCE J (US)
GIRANDA VINCENT L (US)
KEMPF DALE J (US)
STOLL VINCENT S (US)
SUN MINGHUA (US)
ZHAO CHEN (US)
GU YU GUI (US)
HANESSIAN STEPHEN (CA)
WANG GARY T (US)
KRUEGER ALLAN C (US)
CHEN HUI-JU (US)
CHEN YUANWEI (US)
DEGOEY DAVID A (US)
FLOSI WILLIAM J (US)
GRAMPOVNIK DAVID J (US)
KATI WARREN M (US)
KENNEDY APRIL L (US)
KLEIN LARRY L (US)
LIN ZHEN (US)
MADIGAN DAROLD L (US)
International Classes:
C07D401/12; A61K31/357; A61K31/40; A61K31/401; A61K31/4025; A61K31/405; A61K31/415; A61K31/4155; A61K31/4178; A61K31/42; A61K31/422; A61K31/425; A61K31/427; A61K31/4439; A61K31/5377; A61K31/66; A61K31/662; A61P31/00; A61P31/12; A61P31/16; A61P43/00; C07D207/00; C07D207/12; C07D207/16; C07D207/26; C07D207/327; C07D207/38; C07D207/46; C07D303/16; C07D403/04; C07D403/06; C07D405/04; C07D405/06; C07D407/06; C07D407/12; C07D409/06; C07D413/04; C07D413/06; C07D417/04; C07D417/06; C07D521/00; C07F9/40; C07F9/572; C07D207/32; C07D
Domestic Patent References:
| WO1997047194A1 | 1997-12-18 | |||
| WO1999014191A1 | 1999-03-25 | |||
| WO1999033781A1 | 1999-07-08 | |||
| WO1999054290A1 | 1999-10-28 | |||
| WO1999054299A1 | 1999-10-28 |
Other References:
BROUILLETTE W.J. ET AL.: "Design of benzoic acid inhibitors of influenza neuraminidase containing a cyclic substitution for the N-acetyl grouping", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, GB, OXFORD, vol. 9, no. 14, 19 July 1999 (1999-07-19), pages 1901 - 1906, XP004171606, ISSN: 0960-894X
BONNER W.A.: "The stereochemical configurations of the 1-C-phenyl-D-pentitols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 73, no. 7, July 1951 (1951-07-01), pages 3126 - 3131, XP000994866
DYONG I. & BERTRAM H.P.: "Modelluntersuchungen zum Mechanismus der Osazonreaktion, II", CHEMISCHE BERICHTE, VERLAG CHEMIE GMBH. WEINHEIM, DE, vol. 106, 1973, pages 2654 - 2662, XP000994954
FEHRENTZ J-A. & CASTRO B.: "An efficient synthesis of optically active .alpha.-(t-butoxycarbonylamino)-aldehydes from .alpha.-amino acids", SYNTHESIS, GEORG THIEME VERLAG. STUTTGART, DE, no. 8, 1 August 1983 (1983-08-01), pages 676 - 678, XP000573896, ISSN: 0039-7881
COATES R.M. & CUMMINS C.H.: "Preparation of vicinal N-alkylamino alcohols via acylation-rearrangement of nitrones followed by hydride reduction", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 51, no. 9, 2 May 1986 (1986-05-02), pages 1383 - 1389, XP000994893
LARCHEVĂQUE M. ET AL.: "Diastereoselective synthesis of enantiomerically pure syn- or anti-.beta.-alkyl-.gamma.-alkoxyesters by addition of organometallic compounds to .alpha.-alkoxy isopropylidene alkylidenemalonates", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, CHEMICAL SOCIETY. LETCHWORTH, GB, no. 1, January 1989 (1989-01-01), pages 31 - 33, XP000994922
ITAYA T. ET AL.: "Studies towards the synthesis of the fluorescent bases of phenylalanine transfer ribonucleic acids: Synthesis of 7-(2-hydroxy-3-methylbutyl)wye, a model for the minor base isolated from rat liver", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN. TOKYO, JP, vol. 37, no. 5, May 1989 (1989-05-01), pages 1221 - 1225, XP000986003
BERNARDI A. ET AL.: "Asymmetric synthesis of malic acid-type synthons via chiral norephedrine-derived oxazolidines", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 46, no. 6, June 1990 (1990-06-01), pages 1987 - 1998, XP000994912
KECK G.E. ET AL.: "A useful new enantiomerically pure synthon from malic acid: Chelation-controlled activation as a route to regioselectivity", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 56, no. 1, 4 January 1991 (1991-01-04), pages 417 - 420, XP000994865
AOYAMA Y. ET AL.: "A new preparative rout to chiral 2,3-epoxy-1,4-butanediols", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 32, no. 46, November 1991 (1991-11-01), pages 6731 - 6734, XP000994852
MERINO P. ET AL.: "Asymmetric addition reactions of lithium (trimethylsilyl)acetylide with chiral .alpha.-amino nitrones. Synthesis of diastereomerically pure N-hydroxy-.alpha.-amino acids", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 63, no. 16, August 1998 (1998-08-01), pages 5627 - 5630, XP000994940
BONNER W.A.: "The stereochemical configurations of the 1-C-phenyl-D-pentitols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 73, no. 7, July 1951 (1951-07-01), pages 3126 - 3131, XP000994866
DYONG I. & BERTRAM H.P.: "Modelluntersuchungen zum Mechanismus der Osazonreaktion, II", CHEMISCHE BERICHTE, VERLAG CHEMIE GMBH. WEINHEIM, DE, vol. 106, 1973, pages 2654 - 2662, XP000994954
FEHRENTZ J-A. & CASTRO B.: "An efficient synthesis of optically active .alpha.-(t-butoxycarbonylamino)-aldehydes from .alpha.-amino acids", SYNTHESIS, GEORG THIEME VERLAG. STUTTGART, DE, no. 8, 1 August 1983 (1983-08-01), pages 676 - 678, XP000573896, ISSN: 0039-7881
COATES R.M. & CUMMINS C.H.: "Preparation of vicinal N-alkylamino alcohols via acylation-rearrangement of nitrones followed by hydride reduction", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 51, no. 9, 2 May 1986 (1986-05-02), pages 1383 - 1389, XP000994893
LARCHEVĂQUE M. ET AL.: "Diastereoselective synthesis of enantiomerically pure syn- or anti-.beta.-alkyl-.gamma.-alkoxyesters by addition of organometallic compounds to .alpha.-alkoxy isopropylidene alkylidenemalonates", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, CHEMICAL SOCIETY. LETCHWORTH, GB, no. 1, January 1989 (1989-01-01), pages 31 - 33, XP000994922
ITAYA T. ET AL.: "Studies towards the synthesis of the fluorescent bases of phenylalanine transfer ribonucleic acids: Synthesis of 7-(2-hydroxy-3-methylbutyl)wye, a model for the minor base isolated from rat liver", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN. TOKYO, JP, vol. 37, no. 5, May 1989 (1989-05-01), pages 1221 - 1225, XP000986003
BERNARDI A. ET AL.: "Asymmetric synthesis of malic acid-type synthons via chiral norephedrine-derived oxazolidines", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 46, no. 6, June 1990 (1990-06-01), pages 1987 - 1998, XP000994912
KECK G.E. ET AL.: "A useful new enantiomerically pure synthon from malic acid: Chelation-controlled activation as a route to regioselectivity", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 56, no. 1, 4 January 1991 (1991-01-04), pages 417 - 420, XP000994865
AOYAMA Y. ET AL.: "A new preparative rout to chiral 2,3-epoxy-1,4-butanediols", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 32, no. 46, November 1991 (1991-11-01), pages 6731 - 6734, XP000994852
MERINO P. ET AL.: "Asymmetric addition reactions of lithium (trimethylsilyl)acetylide with chiral .alpha.-amino nitrones. Synthesis of diastereomerically pure N-hydroxy-.alpha.-amino acids", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 63, no. 16, August 1998 (1998-08-01), pages 5627 - 5630, XP000994940
Download PDF: