Title:
ORGANIC COMPOUNDS
Document Type and Number:
WIPO Patent Application WO/2021/102896
Kind Code:
A1
Abstract:
Disclosed are TRPM8 modulators as defined by formula (I) for achieving a cooling effect on skin and mucousa.
Inventors:
COCITO ARMANINO NICOLAS (CH)
CHARPENTIER JULIE (CH)
CHEN CHUN (CN)
EMTER ROGER (CH)
GOEKE ANDREAS (CH)
HUANG FENG (CN)
NATSCH ANDREAS (CH)
ZHOU LIJUN (CN)
ZOU YUE (CN)
CHARPENTIER JULIE (CH)
CHEN CHUN (CN)
EMTER ROGER (CH)
GOEKE ANDREAS (CH)
HUANG FENG (CN)
NATSCH ANDREAS (CH)
ZHOU LIJUN (CN)
ZOU YUE (CN)
Application Number:
PCT/CN2019/121927
Publication Date:
June 03, 2021
Filing Date:
November 29, 2019
Export Citation:
Assignee:
GIVAUDAN SA (CH)
WANG CHAO (CN)
WANG CHAO (CN)
International Classes:
A23L33/10; C07D261/20; A61K31/423; C07D265/34
Foreign References:
| JPH0977752A | 1997-03-25 | |||
| JPH0977752A | 1997-03-25 |
Other References:
CHAKRABORTY， B.: "Synthesis of a new heterocyclic system from citronellal derived nitrone", INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 9, 30 September 1999 (1999-09-30), pages 77 - 78
CHAKRABORTY， B.: "Synthesis of a new heterocyclic system from citronellal derived nitrone", INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 9, 30 September 1999 (1999-09-30), pages 77 - 78
LIU, Y. MADEN, A. MURRAY, W.V.: "Amino acid derived intramolecular 1,3-dipolar cycloadditions that form bridged medium ring systems with diastereoselective control", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 58, no. 16, 15 April 2002 (2002-04-15), AMSTERDAM, NL, pages 3159 - 3170, XP004347815, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(02)00242-9
LIU, Y. MADEN, A. MURRAY, W.V.: "Amino acid derived intramolecular 1,3-dipolar cycloadditions that form bridged medium ring systems with diastereoselective control", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 58, no. 16, 15 April 2002 (2002-04-15), AMSTERDAM, NL, pages 3159 - 3170, XP004347815, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(02)00242-9
BRION ET AL: "Stereoselective Synthesis of a trans-Octahydroindole Derivative, Precursor of Trandolapril (RU 44 570), an Inhibitor of Angiotensin Converting Enzyme", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 33, 1 January 1992 (1992-01-01), Amsterdam , NL, pages 4889 - 4892, XP002320609, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)61225-X
BRION ET AL: "Stereoselective Synthesis of a trans-Octahydroindole Derivative, Precursor of Trandolapril (RU 44 570), an Inhibitor of Angiotensin Converting Enzyme", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 33, 1 January 1992 (1992-01-01), Amsterdam , NL, pages 4889 - 4892, XP002320609, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)61225-X
FERNANDEZ BERTA, RIOS MIGUEL A, CARBALLEIRA LUIS: "Conformational analysis of bicyclic systems including the N-C-O unit by molecular mechanics Part II. 4,5-and 5,6-Tetramethylene perhydro-l,3- oxazines", JOURNAL OF MOLECULAR STRUCTURE, vol. 246, 1 January 1991 (1991-01-01), pages 301 - 319, XP055815664
FERNANDEZ BERTA, RIOS MIGUEL A, CARBALLEIRA LUIS: "Conformational analysis of bicyclic systems including the N-C-O unit by molecular mechanics Part II. 4,5-and 5,6-Tetramethylene perhydro-l,3- oxazines", JOURNAL OF MOLECULAR STRUCTURE, vol. 246, 1 January 1991 (1991-01-01), pages 301 - 319, XP055815664
AURICH HANS GÜNTER, BOUTAHAR MOSTAFA, KÖSTER HEINER, MÖBUS KLAUS-DIETER, RUIZ LUIS: "Intramolekulare Cycloaddition von Nitronen", CHEMISCHE BERICHTE, VCH, DE, vol. 123, no. 10, 1 October 1990 (1990-10-01), DE, pages 1999 - 2014, XP055815665, ISSN: 0009-2940, DOI: 10.1002/cber.19901231011
AURICH HANS GÜNTER, BOUTAHAR MOSTAFA, KÖSTER HEINER, MÖBUS KLAUS-DIETER, RUIZ LUIS: "Intramolekulare Cycloaddition von Nitronen", CHEMISCHE BERICHTE, VCH, DE, vol. 123, no. 10, 1 October 1990 (1990-10-01), DE, pages 1999 - 2014, XP055815665, ISSN: 0009-2940, DOI: 10.1002/cber.19901231011
PIHLAJA KALEVI, VAINIOTALO PIRJO, FÜLÖP FERENCE, BERNÁTH GÁBOR: "Stereochemistry and the mass spectra of some 1,3- and 3,1-perhydrobenzoxazines", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, JOHN WILEY & SONS, GB, vol. 2, no. 11, 1 November 1988 (1988-11-01), GB, pages 229 - 232, XP055815667, ISSN: 0951-4198, DOI: 10.1002/rcm.1290021104
PIHLAJA KALEVI, VAINIOTALO PIRJO, FÜLÖP FERENCE, BERNÁTH GÁBOR: "Stereochemistry and the mass spectra of some 1,3- and 3,1-perhydrobenzoxazines", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, JOHN WILEY & SONS, GB, vol. 2, no. 11, 1 November 1988 (1988-11-01), GB, pages 229 - 232, XP055815667, ISSN: 0951-4198, DOI: 10.1002/rcm.1290021104
SCHWARTZ MARTIN A., GERALD C. SWANSON: "Syntheses of the Diastereomeric (i)-a-Bisabolols Chapter IV and references therein", J. ORG. CHEM., vol. 44, no. 6, 1 January 1979 (1979-01-01), XP055815668
SCHWARTZ MARTIN A., GERALD C. SWANSON: "Syntheses of the Diastereomeric (i)-a-Bisabolols Chapter IV and references therein", J. ORG. CHEM., vol. 44, no. 6, 1 January 1979 (1979-01-01), XP055815668
LEBEL NORMAN A., MARY ELLEN POST, DOROTHY HWANG: "Oxidation of Isoxazolidines with Peroxy Acids. Nitrones and N-Hydroxy-1,3-tetrahydrooxazines", J. ORG. CHEM., vol. 44, no. 11, 1 January 1979 (1979-01-01), XP055815670
LEBEL NORMAN A., MARY ELLEN POST, DOROTHY HWANG: "Oxidation of Isoxazolidines with Peroxy Acids. Nitrones and N-Hydroxy-1,3-tetrahydrooxazines", J. ORG. CHEM., vol. 44, no. 11, 1 January 1979 (1979-01-01), XP055815670
BANUCCI LEBEL, LEBEL NORMAN A, BANUCCI EUGENE G: "Intramolecular Nitrone-Olefin Cycloadditions. The Stereochemistry of Hexahydro-2,l-benzisoxazoline Formation1", J. ORG. CHEM, vol. 36, no. 17, 1 January 1971 (1971-01-01), pages 2440 - 2448, XP055764952
BANUCCI LEBEL, LEBEL NORMAN A, BANUCCI EUGENE G: "Intramolecular Nitrone-Olefin Cycloadditions. The Stereochemistry of Hexahydro-2,l-benzisoxazoline Formation1", J. ORG. CHEM, vol. 36, no. 17, 1 January 1971 (1971-01-01), pages 2440 - 2448, XP055764952
LEBEL NORMAN A., THOMAS A. LAJINESS, AND DAVID B. LEDLIE: "Photochemical and Base-Catalyzed Rearrangements of Isoxazolidines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 89, no. 12, 1 January 1967 (1967-01-01), XP055815672
LEBEL NORMAN A., THOMAS A. LAJINESS, AND DAVID B. LEDLIE: "Photochemical and Base-Catalyzed Rearrangements of Isoxazolidines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 89, no. 12, 1 January 1967 (1967-01-01), XP055815672
NORMAN A. LEBEL , MARY ELLEN POST , JONG JAI WHANG: "The Addition of Nitrones to Olefins. Fused Bicyclic Isoxazolidines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 18, 20 September 1964 (1964-09-20), pages 3759 - 3767, XP002726005, ISSN: 0002-7863, DOI: 10.1021/ja01072a031
NORMAN A. LEBEL , MARY ELLEN POST , JONG JAI WHANG: "The Addition of Nitrones to Olefins. Fused Bicyclic Isoxazolidines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 18, 20 September 1964 (1964-09-20), pages 3759 - 3767, XP002726005, ISSN: 0002-7863, DOI: 10.1021/ja01072a031
CHAKRABORTY， B.: "Synthesis of a new heterocyclic system from citronellal derived nitrone", INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 9, 30 September 1999 (1999-09-30), pages 77 - 78
LIU, Y. MADEN, A. MURRAY, W.V.: "Amino acid derived intramolecular 1,3-dipolar cycloadditions that form bridged medium ring systems with diastereoselective control", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 58, no. 16, 15 April 2002 (2002-04-15), AMSTERDAM, NL, pages 3159 - 3170, XP004347815, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(02)00242-9
LIU, Y. MADEN, A. MURRAY, W.V.: "Amino acid derived intramolecular 1,3-dipolar cycloadditions that form bridged medium ring systems with diastereoselective control", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 58, no. 16, 15 April 2002 (2002-04-15), AMSTERDAM, NL, pages 3159 - 3170, XP004347815, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(02)00242-9
BRION ET AL: "Stereoselective Synthesis of a trans-Octahydroindole Derivative, Precursor of Trandolapril (RU 44 570), an Inhibitor of Angiotensin Converting Enzyme", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 33, 1 January 1992 (1992-01-01), Amsterdam , NL, pages 4889 - 4892, XP002320609, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)61225-X
BRION ET AL: "Stereoselective Synthesis of a trans-Octahydroindole Derivative, Precursor of Trandolapril (RU 44 570), an Inhibitor of Angiotensin Converting Enzyme", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 33, 1 January 1992 (1992-01-01), Amsterdam , NL, pages 4889 - 4892, XP002320609, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)61225-X
FERNANDEZ BERTA, RIOS MIGUEL A, CARBALLEIRA LUIS: "Conformational analysis of bicyclic systems including the N-C-O unit by molecular mechanics Part II. 4,5-and 5,6-Tetramethylene perhydro-l,3- oxazines", JOURNAL OF MOLECULAR STRUCTURE, vol. 246, 1 January 1991 (1991-01-01), pages 301 - 319, XP055815664
FERNANDEZ BERTA, RIOS MIGUEL A, CARBALLEIRA LUIS: "Conformational analysis of bicyclic systems including the N-C-O unit by molecular mechanics Part II. 4,5-and 5,6-Tetramethylene perhydro-l,3- oxazines", JOURNAL OF MOLECULAR STRUCTURE, vol. 246, 1 January 1991 (1991-01-01), pages 301 - 319, XP055815664
AURICH HANS GÜNTER, BOUTAHAR MOSTAFA, KÖSTER HEINER, MÖBUS KLAUS-DIETER, RUIZ LUIS: "Intramolekulare Cycloaddition von Nitronen", CHEMISCHE BERICHTE, VCH, DE, vol. 123, no. 10, 1 October 1990 (1990-10-01), DE, pages 1999 - 2014, XP055815665, ISSN: 0009-2940, DOI: 10.1002/cber.19901231011
AURICH HANS GÜNTER, BOUTAHAR MOSTAFA, KÖSTER HEINER, MÖBUS KLAUS-DIETER, RUIZ LUIS: "Intramolekulare Cycloaddition von Nitronen", CHEMISCHE BERICHTE, VCH, DE, vol. 123, no. 10, 1 October 1990 (1990-10-01), DE, pages 1999 - 2014, XP055815665, ISSN: 0009-2940, DOI: 10.1002/cber.19901231011
PIHLAJA KALEVI, VAINIOTALO PIRJO, FÜLÖP FERENCE, BERNÁTH GÁBOR: "Stereochemistry and the mass spectra of some 1,3- and 3,1-perhydrobenzoxazines", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, JOHN WILEY & SONS, GB, vol. 2, no. 11, 1 November 1988 (1988-11-01), GB, pages 229 - 232, XP055815667, ISSN: 0951-4198, DOI: 10.1002/rcm.1290021104
PIHLAJA KALEVI, VAINIOTALO PIRJO, FÜLÖP FERENCE, BERNÁTH GÁBOR: "Stereochemistry and the mass spectra of some 1,3- and 3,1-perhydrobenzoxazines", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, JOHN WILEY & SONS, GB, vol. 2, no. 11, 1 November 1988 (1988-11-01), GB, pages 229 - 232, XP055815667, ISSN: 0951-4198, DOI: 10.1002/rcm.1290021104
SCHWARTZ MARTIN A., GERALD C. SWANSON: "Syntheses of the Diastereomeric (i)-a-Bisabolols Chapter IV and references therein", J. ORG. CHEM., vol. 44, no. 6, 1 January 1979 (1979-01-01), XP055815668
SCHWARTZ MARTIN A., GERALD C. SWANSON: "Syntheses of the Diastereomeric (i)-a-Bisabolols Chapter IV and references therein", J. ORG. CHEM., vol. 44, no. 6, 1 January 1979 (1979-01-01), XP055815668
LEBEL NORMAN A., MARY ELLEN POST, DOROTHY HWANG: "Oxidation of Isoxazolidines with Peroxy Acids. Nitrones and N-Hydroxy-1,3-tetrahydrooxazines", J. ORG. CHEM., vol. 44, no. 11, 1 January 1979 (1979-01-01), XP055815670
LEBEL NORMAN A., MARY ELLEN POST, DOROTHY HWANG: "Oxidation of Isoxazolidines with Peroxy Acids. Nitrones and N-Hydroxy-1,3-tetrahydrooxazines", J. ORG. CHEM., vol. 44, no. 11, 1 January 1979 (1979-01-01), XP055815670
BANUCCI LEBEL, LEBEL NORMAN A, BANUCCI EUGENE G: "Intramolecular Nitrone-Olefin Cycloadditions. The Stereochemistry of Hexahydro-2,l-benzisoxazoline Formation1", J. ORG. CHEM, vol. 36, no. 17, 1 January 1971 (1971-01-01), pages 2440 - 2448, XP055764952
BANUCCI LEBEL, LEBEL NORMAN A, BANUCCI EUGENE G: "Intramolecular Nitrone-Olefin Cycloadditions. The Stereochemistry of Hexahydro-2,l-benzisoxazoline Formation1", J. ORG. CHEM, vol. 36, no. 17, 1 January 1971 (1971-01-01), pages 2440 - 2448, XP055764952
LEBEL NORMAN A., THOMAS A. LAJINESS, AND DAVID B. LEDLIE: "Photochemical and Base-Catalyzed Rearrangements of Isoxazolidines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 89, no. 12, 1 January 1967 (1967-01-01), XP055815672
LEBEL NORMAN A., THOMAS A. LAJINESS, AND DAVID B. LEDLIE: "Photochemical and Base-Catalyzed Rearrangements of Isoxazolidines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 89, no. 12, 1 January 1967 (1967-01-01), XP055815672
NORMAN A. LEBEL , MARY ELLEN POST , JONG JAI WHANG: "The Addition of Nitrones to Olefins. Fused Bicyclic Isoxazolidines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 18, 20 September 1964 (1964-09-20), pages 3759 - 3767, XP002726005, ISSN: 0002-7863, DOI: 10.1021/ja01072a031
NORMAN A. LEBEL , MARY ELLEN POST , JONG JAI WHANG: "The Addition of Nitrones to Olefins. Fused Bicyclic Isoxazolidines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 18, 20 September 1964 (1964-09-20), pages 3759 - 3767, XP002726005, ISSN: 0002-7863, DOI: 10.1021/ja01072a031
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CCPIT PATENT AND TRADEMARK LAW OFFICE (CN)
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