Intervet Inc.

Intervet International B.v.

Christophe Pierre Alain Chassaing

Jürgen Lutz

Thorsten Meyer

Anja Regina Heckeroth

Sandra Koch

Edward Cleator

Manfred Uphoff

Richard John Varsolona

Harald Schmitt

Jingjun Yin

Britta Von Oepen

Jörg Schröder

Wensong Xiao

Ulrich Sondern

Karl-Heinz Grimm

Xiaoling Jin

Adrian Goodyear

Jonathan Simmons

Tanja Schweisel

Thomas Dahmen

Thomas Simon Ilg

Claudia Scheipers

Daniel Salanta

Lichen Song

Lorenzo Codan

Rositza Iordanova Petrova

The application relates to processes for the preparation of 1-[(3R,4S)-4-cyanotetrahydropyran-3-yl]-3-[(2-fluoro-6-methoxy-4-pyridyl) amino]pyrazole-4-carboxamide (I) which include (i) a synthesis for bromo and iodo pyridine intermediates, (ii) a synthesis of a pyrazole ester intermediate which can be obtained in enantiopure form and (iii) the combination of these intermediates into compound (I).

Process for preparing 1-([3R,4S)-4-cyanotetrahydropyran-3-yl]-3-[(2-fluoro-6-methoxy-4-pyridyl)amino]pyrazole-4-carboxamide

A process for chiral separation of ethyl 3-amino-1-[(3R,4S)-4-cyanotetrahydropyran-3-yl]pyrazole-4-carboxylate (VI) from the racemic mixture of ethyl 3-amino-1-[(3R,4S)-4-cyanotetrahydropyran-3-yl]pyrazole-4-carboxylate and ethyl 3-amino-1-[(3S,4R)-4-cyanotetrahydropyran-3-yl]pyrazole-4-carboxylate (V).

Process for the production of ethyl 3-amino-1-[(3R,4S)-4-cyanotetrahydropyran-3-yl]pyrazole-4-carboxylate through chiral separation of a racemic mixture

The present application relates to crystalline forms of 1-[(3R,4S)-4-cyanotetrahydropyran-3-yl]-3-[(2-fluoro-6-methoxy-4-pyridyl) amino]pyrazole-4-carboxamide and processes for the preparation thereof. The compound is useful for the treatment of JAK-mediated diseases or conditions such as atopic dermatitis.

Crystalline forms of 1-[(3R,4S)-4-cyanotetrahydropyran-3-yl]-3-[(2-fluoro-6-methoxy-4-pyridyl)amino]pyrazole-4-carboxamide

This invention is directed to compounds and salts that are generally useful as agents to treat an infection with. This invention also is directed to treatments comprising the administration of the compounds and salts to animals in need of the treatments.

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This invention relates to spiroindoline compounds for the treatment of helminth infections and the treatment of parasitosis, such as caused by helminth infections. This invention also relates to uses of the compounds to make medicaments and treatments comprising the administration of the compounds to animals in need of the treatments. Moreover this invention relates to pharmaceutical compositions and kits comprising the compounds.

Spiroindoline compounds for use as anthelminthics

This invention is directed to compounds and salts that are generally useful as anthelmintic agents or as intermediates in processes for making anthelmintic agents. This invention also is directed to processes for making the compounds and salts, pharmaceutical compositions and kits comprising the compounds and salts, uses of the compounds and salts to make medicaments, and treatments comprising the administration of the compounds and salts to animals in need of the treatments. 

Anthelmintic agents and their use

This invention relates to novel spiroindoline compounds of formula (I) that are generally useful as medicaments, more specifically as medicaments for animals. The medicament can preferably be used for the treatment of helminth infections and the treatment of parasitosis, such as caused by helminth infections. This invention also relates to uses of the compounds to make medicaments and treatments comprising the administration of the compounds to animals in need of the treatments. This invention also relates to the preparation of said compounds. Moreover this invention relates to pharmaceutical compositions and kits comprising the compounds. 

Spiroindoline compounds

This invention is directed to compounds and salts that are generally useful as anthelmintic agents or as intermediates in processes for making anthelmintic agents. This invention also is directed to processes for making the compounds and salts, pharmaceutical compositions and kits comprising the compounds and salts, uses of the compounds and salts to make medicaments, and treatments comprising the administration of the compounds and salts to animals in need of the treatments.

This invention is directed to compounds of the formula (I) and salts therefore that are generally useful as anthelmintic agents or as intermediates in processes for making anthelmintic agents. This invention also is directed to processes for making the compounds of this invention, pharmaceutical compositions and kits comprising the compounds of this invention, uses of the compounds of this invention to make medicaments, and treatments comprising the administration of the compounds of this invention to animals in need of the treatments.

This invention relates to benzimidazole carbamates and (thio)carbamates corresponding to Formula I: Here, Xand Xare independently O or S, wherein at least one of Xand Xis O; Yand Yare independently O or S, wherein at least one of Yand Yis O; Ris alkyl having from 1-4 carbon atoms; R, R, and Rare independently hydrogen or a cation; Rand Rare independently hydrogen, halogen, alkyl (having from 1-8 carbon atoms), &#x2014;OR, &#x2014;SR, &#x2014;CO&#x2014;R, &#x2014;OSO&#x2014;Ar, or &#x2014;S(O)R; Ris alkyl having from 1-8 carbon atoms; Ris alkyl (having from 1-8 carbon atoms) or aryl; Ris alkyl (having from 1-8 carbon atoms), cycloalkyl (having from 3-6 carbon atoms), or aryl; Ar is aryl; and Ris alkyl (having from 1-8 carbon atoms) or aryl. The compounds generally are soluble and stable in water, and have antiparasitic (particularly anthelmintic) activity in vivo that is comparable to known water-insoluble benzimidazole carbamates (e.g., albendazole and fenbendazole).

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Schwabenheim, Germany

Christophe Pierre Alain Chassaing