EA040923B1 - SUBSTITUTED N-(1,3,4-OXADIAZOL-2-YL)ARYLCARBOXAMIDES AND THEIR USE AS HERBICIDES - Google Patents

Description

The invention relates to the field of technology related to herbicides, in particular to the field associated with heterocyclically substituted arylcarboxamides for the selective control of broadleaf weeds and weeds in crops of useful plants.

The herbicidal action of heterocyclically substituted aryl carboxamides is well known.

According to the heterocyclic fragments of these compounds, herbicides according to the prior art can be divided into tetrazol- and triazol-substituted arylcarboxamides and oxadiazole-substituted arylcarboxamides.

WO 2012/028579 A1 discloses N-(tetrazol-4-yl)benzamides and N-(triazol-3yl)benzamides which are substituted at the 2-, 3- and 4-position of the phenyl ring and have herbicidal activity. WO 2014/184015 A1 also discloses N-(tetrazol-4-yl)benzamides and N-(triazol-3yl)benzamides with herbicidal activity and the compounds disclosed in WO 2014/184015 are substituted on the phenyl ring at position 2, 3, 4, as well as in positions 5 and 6.

Document WO 2011/035874 A1 discloses oxadiazole-substituted benzamide compounds, namely N-(1,2,5-oxadiazol-3-yl)phenylbenzamides, which are substituted at the 2-, 3- and 4-position of the phenyl ring and have herbicidal action. Other N-(1,2,5-oxadiazol-3yl)phenylbenzamides are known from EP 0173657 A1.

Document WO 2012/126932 A1 also discloses N-(1,3,4-oxadiazol-2-yl)benzamides, where the benzyl (aryl moiety) is also in each case only in the 2, 3 and 4 position, i.e. compounds with herbicidal activity known from WO 2012/126932 A1 are not substituted in positions 5 and 6 of the phenyl moiety.

Also document WO 2017/102275 A1, which is the relevant document in relation to the present application in accordance with Art. 54 (3) EPC, discloses additional N-(1,3,4-oxadiazol-2yl)benzamides with the alternative Q ⁴ =1,3,4-oxadiazol-2-yl. The compounds claimed in WO 2017/102275 A1 are distinguished by a phenyl substituent, referred to as R ² , which has a diamide structure. The two compounds listed in WO 2017/102275 A1 in the list (Table IV, page 113) were excluded from the scope of the present invention.

In addition, the starting material used in WO 2017/102275 A1, namely 3-amino-4-bromo-6fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide , has been excluded from the scope of the present invention. This compound, disclosed in connection with example 3 in WO 2017/102275 A1, has an amino group at the position of the radical Y of the present invention instead of a radical with a diamide structure.

In addition to the three compounds mentioned above, six other commercially available compounds are excluded from the scope of the present invention. For these six compounds, the compounds have not been found to be used as herbicides in the prior art.

However, known N-(1,3,4-oxadiazol-2-yl)benzamides often lack herbicidal activity.

Accordingly, it is an object of the present invention to provide further N-(1,3,4oxadiazol-2-yl)benzamides having improved herbicidal activity.

The task is achieved using K-(1,3,4-oxadiazol-2-yl)arylcarboxamides according to claim 1, i.e. with N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of formula (I) or their salts

ν where the substituents have the following meanings:

A is N or C-Y,

R is hydrogen or (C ₁ -C ₆ )alkyl,

X is halogen or (C1-C ₆ )alkyl,

Y is halogen, (C1-C ₆ )alkyl, S(O)nR ² or 2-oxoazetidin-1-yl or C(O)N(R1) ₂ ,

Z is halogen, (C1-C ₆ )alkyl, S(O)nR ² or halo(C1-C ₆ )alkyl,

V represents hydrogen, halogen or (C1-C ₆ )alkyl,

W is hydrogen, halogen or (C1-C ₆ )haloalkyl, provided that in each case at least one of V and W is not hydrogen, i.e. that in the positions of the radicals V and W of the compound (I) only V or only W can represent hydrogen,

R ¹ is hydrogen, (C1-C ₆ )alkyl, (C1-C ₆ )haloalkyl or (C ₃ -C ₆ )cycloalkyl(C1C ₆ )alkyl,

R ² is (C1-C ₆ )alkyl, n is 0, 1 or 2, provided that the compounds

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4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxαduαzol-2-yl)benzαmide,

4-Bromo-2,6-difluoro-2-Ni(5-cyclopropyl-1,3,4-oxadiazol-2-yl)benzamide are excluded.

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the invention differ from the known N-(1,3,4oxadiazol-2-yl)arylcarboxamides, in particular, by additional substituents at positions 5 and 6 of the phenyl moiety.

The core of the invention relates to the unexpected discovery that, in the case of N-(1,3,4-oxadiazol-2yl)arylcarboxamides, phenyl substituents at the 5 and 6 positions of the phenyl, in combination with other substituents, have an unexpectedly high value for herbicidal activity.

In formula (I) and all subsequent formulas, alkyl radicals having more than two carbon atoms may be linear or branched. Alkyl radicals are, for example, methyl, ethyl, n-propyl or isopropyl, n-, iso-, tert- or 2-butyl, pentyls, hexyls such as nhexyl, isohexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, partially saturated or fully unsaturated cyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 represent an oxygen, nitrogen and sulfur group, and which may be further fused with a benzo ring.

For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl, and oxetanyl.

Heteroaryl is an aromatic cyclic radical which contains 3-6 ring atoms, of which 1 to 4 represent an oxygen, nitrogen and sulfur group, and which can be further fused with a benzo ring. For example, heteroaryl is benzimidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1,2,3-oxadiazolyl, 1,2,4oxadiazolyl , 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1 ,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H -1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl .

If a group is polysubstituted by radicals, it is to be understood that this group is substituted by one or more of the same or different radicals selected from the said radicals.

Depending on the nature of the substituents and the manner in which they are attached, the compounds of general formula (I) may be present as stereoisomers. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers also occur when n is 1 (sulfoxides). Stereoisomers can be obtained from mixtures obtained by conventional separation methods, for example, using chromatographic separation methods. It is also possible to selectively obtain stereoisomers using stereoselective reactions using optically active starting materials and/or auxiliary substances. The invention also relates to all stereoisomers and mixtures thereof which are covered by the general formula (I) but are not specifically defined.

Still particularly preferred are the N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of formula (I) in which A is CY, where V is hydrogen, W is fluorine and the radicals R, X, Y and Z, as well as the radicals R1-R ² and also n, each independently of one another, have the meanings indicated above.

With regard to the general definition of the substituent Y=S(O) _n R, where n=0, n=1 or n=2, the most preferred radicals are methylsulfanyl (SMe), methylsulfinyl (methylsulfoxide (SOMe)), methylsulfonyl (SO ₂ Me) , ethylsulfanyl (SEt), ethylsulfinyl (ethylsulfoxide (SOEt)) and ethylsulfonyl (SO ₂ Et), where R ² =methyl (Me) or R ² =ethyl (Et).

Most preferred are the three methyl-substituted Y alternatives, i.e. Y=SMe, Y=SOMe, Y=SO2Me.

Accordingly, N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of formula (I), in which the substituents have the following meanings:

A represents C-Y,

R is methyl,

X is chlorine or methyl,

Y is SMe, SOMe or SO ₂ Me,

Z is trifluoromethyl or chlorine,

V is hydrogen,

W is fluorine are particularly preferred in the context of the particular aspect mentioned above.

The following tabular compilation specifically discloses six compounds of general formula (I) which are most preferred according to the aspect mentioned above, in which, as shown in the formula below, A is CY, X is chlorine or methyl, Y is methylsulfanyl, methylsulfinyl or methylsulfonyl, Z is trifluoromethyl, V is hydrogen, W is fluorine, and R is methyl:

No. X Y Compound 2-143 C1 SMe 2-χπορ-6-φτορ-Ν-(5-methyl-1,3,4-oxadiazol-2-yl)-3(methylsulfanyl)-4-(trifluoromethyl)benzamide 2-144 C1 S(O)Me 2-χπορ-6-φτορ-Ν-(5-methyl-1,3,4-oxadiazol-2-yl)-3(methylsulfinyl)-4-(trifluoromethyl)benzamide 2-145 C1 SO ₂ Me 2-χπορ-6-φτορ-Ν-(5-methyl-1,3,4-oxadiazol-2-yl)-3(methylsulfonyl)-4-(trifluoromethyl)benzamide 2-359 m e SMe 6-fluoro-2-methyl-X-(5-methyl-1,3,4-oxadiazol-2-yl)-3 (methylsulfanyl)-4-(trifluoromethyl)benzamide 2-360 m e S(O)Me 6-fluoro-2-methyl-X-(5-methyl-1,3,4-oxadiazol-2-yl)-3 (methylsulfinyl)-4-(trifluoromethyl)benzamide 2-361 M e SO ₂ Me 6-fluoro-2-methyl-X-(5-methyl-1,3,4-oxadiazol-2-yl)-3(methylsulfonyl)-4-(trifluoromethyl)benzamide

Alternatively, N-(1,3,4-oxadiazol-2yl)arylcarboxamides of formula (I) are preferred, wherein A is N (instead of C-Y), where

V is hydrogen,

W is fluorine,

Z represents CF ₃ and the radicals R, X and Y, as well as the radicals R1-R ² and also n, each independently of the other, have the meanings indicated above.

In all formulas below, substituents and symbols have the same meaning as described in formula (I), unless otherwise defined.

Compounds according to the invention can be obtained, for example, by the method shown in Scheme 1, by the basic catalyzed reaction of benzoyl or nicotinoyl chloride (II) with 2-amino1,3,4-oxadiazole (III).

Scheme 1

Benzoyl chlorides of formula (II) or their starting benzoic acids are known in principle and can be prepared, for example, by the methods described in US 6376429 B1, EP 1585742 A1, WO 2014/184015, WO 2014/184016, WO 2013/083859 and EP 1202978 A1 .

Compounds according to the invention can also be prepared in the manner described in Scheme 2 by reacting benzoic or nicotinic acid of formula (IV) with 2-amino-1,3,4-oxadiazole (III).

Scheme 2

Dehydrating reagents that are commonly used for amidation reactions can be used for activation, e.g. -trioxatrifosfinan, 2,4,6-trioxide (T3P), etc.

Compounds according to the invention can also be prepared in the manner described in Scheme 3 by cyclization of a compound of formula V.

Scheme 3

Cyclization can be done in the ways described in Synth. commun. 31 (12), 1907-1912 (2001) or in Indian J. Chem., Section B: Organic Chemistry Including Medicinal Chemistry; Vol. 43 (10),

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2170-2174 (2004).

Scheme 4

(VI) (VII) (V)

The compound of formula V used in Scheme 3 can be prepared by reacting an acyl isocyanate of formula VII with a hydrazide of formula VI in the manner described in Synth. commun. 25 (12), 1885-1892 (1995).

It may be advantageous to change the sequence of reaction steps. For example, benzoic acids that carry a sulfoxide cannot be directly converted to their acid chlorides. One option here is to first prepare the amide in the thioether step and then oxidize the thioester to the sulfoxide.

Sets of compounds of formula (I) and/or their salts, which can be synthesized by the above reactions, can also be obtained in a parallel way, in which case this can be done manually, partially automatic or fully automatic. For example, it is possible to automate the reaction, processing or purification of products and/or intermediates. In general, this refers to the procedure described, for example, by D. Tiebes in Combinatorial Chemistry-Synthesis, Analysis, Screening (publisher: Gunther Jung), Wiley, 1999, pages 1-34.

A number of commercially available instruments can be used for parallel reaction and processing, such as Calypso Reaction Blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or Reaction Stations from Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, England, or MultiPROBE automated workstations from Perkin Elmer, Waltham, Massachusetts 02451, USA. For the parallel purification of compounds of general formula (I) and their salts or intermediates, which occurs during preparation, available devices include chromatographic devices, for example, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

The devices described in detail lead to a modular procedure in which the individual work steps are automated, but manual operations must be carried out between the work steps. This can be circumvented by using partially or fully integrated automation systems, in which the respective automation modules are controlled, for example, by robots. Automation systems of this type are available from, for example, Caliper, Hopkinton, MA 01748, USA.

The implementation of one or more stages of the synthesis can be supported by the use of polymer-based reagents/absorbent resin. A number of experimental protocols are described in the literature, for example, in ChemFiles, Vol. 4, no. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

In addition to the methods described in this application, the compounds of General formula (I) and their salts can be obtained in whole or in part by methods based on the solid phase. To this end, individual intermediates or all intermediates in a synthesis or a synthesis adapted to the appropriate technique are associated with a synthetic resin. Solid phase methods are described in detail in the technical literature, for example, Barry A. Bunin in The Combinatorial Index, Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher: Gunther Jung), Wiley, 1999. solid phase allows the use of a number of protocols known from the literature, which, for their part, can be performed manually or automatically. Reactions can be performed, for example, using IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.

In both solid and liquid phases, the implementation of individual or multiple synthesis steps can be supported by using microwave technology. A number of experimental protocols are described in the literature, for example, Microwaves in Organic and Medicinal Chemistry (publishers: C. O. Kappe and A. Stadler), Wiley, 2005.

Preparation by the methods described here gives the compounds of formula (I) and their salts in the form of sets of substances, which are called libraries. The present invention also provides libraries containing at least two compounds of formula (I) and their salts.

The compounds of formula (I) according to the invention (and/or their salts), hereinafter collectively referred to as the compounds according to the invention, have excellent herbicidal efficacy against a wide range of economically important monocot and dicot annual pests. The active ingredients also work well against perennial harmful plants that are difficult to control and shoot from rhizomes, root stalks or other perennial organs.

Thus, the present invention also provides a method for controlling or regulating plant growth, preferably in crop plants, wherein one

- 4 040923 or more compounds according to the invention are applied to plants (for example, harmful plants, such as monocotyledonous or dicotyledonous weeds or undesirable agricultural plants), inoculum (for example, grains, seeds or vegetative shoots, such as tubers or shoots with buds) or the area on which plants grow (for example, crop area). The compounds of the invention can be applied, for example, before sowing (if necessary also by incorporation into the soil), before or after emergence. Specific examples of some of the monocot and dicot weeds that can be controlled with the compounds of the invention are as follows, although the listing is not intended to be limiting to certain species.

Monocotyledonous harmful plant genera:

Aegilops, Agropyron, Agrostis,

Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds genera:

Abutilon, Amaranthus, Ambrosia, Anoda,

Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia,

Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds according to the invention are applied to the soil surface prior to germination, either emergence of weeds is prevented or the weeds grow until they reach the cotyledon stage but then stop growing and eventually die completely after three to four weeks.

If the active compounds are applied after emergence to the green parts of the plants, the growth stops after the treatment, and the harmful plants remain in the growth stage during the application or die completely after a certain time, so that thus the struggle for existence from the weeds, which is harmful to agricultural plants , is eliminated very early and persistently.

Although the compounds according to the invention have outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, agricultural plants of economically important crops, for example, dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Lactuca, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia or monocots of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, will be damaged only slightly, if at all, depending on the structure of the particular compound of the invention and the dose of its application. For these reasons, the present compounds are very suitable for the selective control of unwanted plant growth in crop plants such as agricultural useful plants or ornamental plants.

In addition, the compounds according to the invention (depending on their specific structure and applied application rate) have outstanding growth regulating properties in crop plants. They interfere with the metabolism of the plants themselves with a regulating effect and thus can be used to control plant components and to facilitate harvesting, for example by causing desiccation and stunting. In addition, they are also suitable for general control and suppression of unwanted vegetative growth without killing plants in the process. Inhibition of vegetative growth plays a major role in many monocots and dicots because, for example, it can reduce or completely prevent lodging.

By virtue of their herbicidal and plant growth regulating properties, the active compounds can also be used to control harmful plants in cultures of genetically modified plants or plants modified by conventional mutagenesis. In general, transgenic plants are characterized by particular advantageous properties, for example resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or plant disease pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific properties relate, for example, to the collected material in terms of quantity, quality, storability, composition and specific components. For example, there are known transgenic plants with increased starch content or altered starch quality.

- 5 040923 la, or plants with a different composition of fatty acids in the collected material.

With regard to transgenic crop plants, it is preferable to use the compounds according to the invention in economically important transgenic crops of useful plants and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet/sorghum, rice and maize or other crops such as such as sugar beets, cotton, soybeans, oilseed rape, potatoes, tomatoes, peas and other types of vegetables. Preferably, the compounds according to the invention can be used as herbicides in crops of useful plants that are or have been genetically engineered to be resistant to the phytotoxic effects of herbicides.

It is preferred to use the compounds according to the invention or their salts in economically important transgenic crops of useful plants and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet/sorghum, rice, cassava and corn, or other crops such as such as sugar beets, cotton, soybeans, oilseed rape, potatoes, tomatoes, peas and other types of vegetables. Preferably, the compounds according to the invention can be used as herbicides in crops of useful plants that are or have been genetically engineered to be resistant to the phytotoxic effects of herbicides.

Conventional methods for obtaining new plants that have modified properties compared to existing plants are, for example, traditional methods of cultivation and generation of mutants.

Alternatively, new plants with modified properties can be obtained using recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, have been described in several cases:

genetic modification of cultivated plants to modify starch synthesized in plants (eg WO 92/11376, WO 92/14827, WO 91/19806);

transgenic crop plants which are resistant to certain herbicides of the glufosinate type (see, for example, EP-A-0242236, EP-A-242246) or the glyphosate type (WO 92/00377) or the sulfonylurea type (EP-A-0257993, US- A-5013659);

transgenic crop plants, for example cotton, capable of producing Bacillus thuringiensis toxins (Bt toxins) which render plants resistant to certain pests (EP-A0142924, EP-A-0193259);

transgenic crop plants having a modified fatty acid composition (WO 91/13972);

genetically modified crop plants with new components or secondary metabolites, for example, new phytoalexins, which cause increased resistance to diseases (EPA 309862, EPA0464461);

genetically modified plants with reduced photorespiration, which have a higher yield and higher stress resistance (EPA 0305398);

transgenic crop plants that produce pharmaceutically or diagnostically important proteins (molecular farming);

transgenic crop plants that have a higher yield or better quality;

transgenic crop plants that have a combination of, for example, the above novel properties (gene packaging).

In principle, numerous molecular biology techniques are known that can be used to produce new transgenic plants with modified properties; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, Trends in Plant Science 1 (1996) 423-431.

For such genetic manipulations, nucleic acid molecules that allow mutagenesis or sequence change by recombination of DNA sequences can be introduced into plasmids. Using standard methods, it is possible, for example, to carry out basic exchanges, to remove portions of sequences, or to add natural or synthetic sequences. To connect DNA fragments to each other, adapters or linkers can be placed on the fragments, see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY , or Winnacker Gene und Klone [Genes and clones], VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with reduced gene product activity can be achieved by expressing at least one appropriate antisense RNA, sense RNA to achieve a co-suppression effect, or by expressing at least one suitably designed ribozyme that specifically cleaves transcripts of the above gene product. . To this end, one can firstly use DNA molecules that span the entire coding sequence of the gene product, including any flanking sequences that may be present, as well as DNA molecules that span only portions of the coding sequence, in which case it is necessary that these parts were long enough to have an antisense effect in the cells. You can also use DNA sequences that have a high degree of homology with the coding sequences of the gene product, but are not completely identical to them.

When the nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any desired compartment of the plant cell. However, in order to achieve localization in a particular compartment, one can, for example, attach a coding region to DNA sequences that provide localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 32193227, Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846- 850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in plant cell organelles.

Transgenic plant cells can be regenerated by known techniques to promote the emergence of whole plants. In principle, the transgenic plants can be plants of any desired plant species, ie. not only monocotyledons, but also dicotyledonous plants.

Thus, transgenic plants can be obtained whose properties are changed by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences, or by the expression of heterologous (=foreign) genes or gene sequences.

The compounds according to the invention can preferably be used in transgenic crops which are resistant to growth regulators, for example dicamba or herbicides which inhibit essential plant enzymes, for example acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and similar active compounds.

When the active compounds according to the invention are used in transgenic crops, not only the effects on harmful plants observed in other crops occur, but often also effects specific to the application in individual transgenic crops, for example, an altered or specifically broadened spectrum of weeds, which can be susceptible to control, modified application rates that can be used for application, preferably good compatibility with herbicides to which transgenic crops are resistant, and effects on growth and yield of transgenic crop plants.

Thus, the present invention also provides for the use of the compounds according to the invention as herbicides for the control of harmful plants in transgenic plants.

The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, spray solutions, dusting products or granules in conventional formulations. Thus, the invention also provides herbicidal and plant growth regulating compositions which contain compounds according to the invention.

The compounds according to the invention can be formulated in various ways, according to the required biological and/or physico-chemical parameters. Possible formulations include, for example: wettable powders (WP), water soluble powders (SP), water soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions , spray solutions, suspension concentrates (SC), oil-based or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for spreading and soil application, granules (GR) in the form of microgranules, sprayable granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual types of formulations are known in principle and are described, for example, in

Winnacker-Kiichler, Chemische Technologie [Chemical Technology], Volume 7, C.

Hanser Verlag Munich, 4th Ed. 1986, Wade van Valkenburg, Pesticide

Formulations, Marcel Dekker, N.Y., 1973, K. Martens, Spray Drying Handbook,

3rd Ed. 1979, G. Goodwin Ltd. London.

Required formulation auxiliaries such as inerts, surfactants, solvents and other additives are also known and described, for example, in

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Watkins, Handbook of Insecticide Dust

Diluents and Carriers, 2nd Ed., Darland Books, Caldwell N.J.; H.v. Olphen, Introduction to Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons, N.Y.; C.

Marsden, Solvents Guide, 2nd Ed., Interscience, N.Y. 1963; McCutcheon's

Detergents and Emulsifiers Annual, M.C. Publ. Corp., Ridgewood N.J.; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964;

Schonfeldt, Grenzflachenaktive Athylenoxidaddukte [Interface-active Ethylene

Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Kiichler, Chemische Technologie [Chemical Engineering], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to obtain combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, as well as safeners, fertilizers and/or growth regulators, for example, in the form of a ready-made composition or as a tank mix. Suitable antidotes are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexil and dichlormide.

Wettable powders are preparations uniformly dispersible in water which, in addition to the active ingredient, in addition to the diluent or inert substance, also contain surfactants of the ionic and/or non-ionic type (wetting agent, dispersant), e.g. polyethoxylated alkylphenols, polyethoxylated fatty alcohols , polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkane sulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphtylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyl taurate. To obtain wettable powders, the herbicidally active compounds are finely ground, for example, in conventional devices such as hammer mills, blower mills and air jet mills, and simultaneously or sequentially mixed with formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or relatively high boiling aromatics or hydrocarbons, or mixtures of organic solvents, with the addition of one or more ionic and/or nonionic surfactants (emulsifiers). ). Examples of emulsifiers that can be used are calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide and ethylene oxide condensates, alkylpolyethers, esters. sorbitan, for example, esters of sorbitan and fatty acids, or esters of polyoxyethylene and sorbitan, for example, esters of polyoxyethylene sorbitan and fatty acids.

Dusting products are prepared by triturating the active compound with finely divided solids such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates may be water or oil based. They can be obtained, for example, by wet grinding with commercially available ball mills and the optional addition of surfactants, which, for example, have already been listed above for other types of compositions. Emulsions, such as oil-in-water (EW) emulsions, can be prepared, for example, using agitators, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants, as already mentioned above, for example , for other types of compositions. Granules can be prepared either by spraying the active compound onto an adsorptive granular inert material or by applying concentrates of the active compound to the surface of carriers such as sand, kaolinites or granular inert material using adhesives such as polyvinyl alcohol, sodium polyacrylate or other mineral oils. . Suitable active compounds can also be granulated in the usual way to obtain fertilizer granules, if desired as a mixture with fertilizers. Water-dispersible granules are generally produced by conventional methods such as spray drying, fluid bed granulation, cup granulation, mixing with high speed mixers, and extrusion without solid inert material. For the production of granules for the cup granulator, fluidized bed, extruder and spray, see for example the methods described in

- 8 040923

Spray-Drying Handbook 3rd Ed. 1979, G. Goodwin Ltd.,

London, J.E. Browning, Agglomeration, Chemical and Engineering 1967, pages 147 ff.; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details regarding the preparation of crop protection compositions, see, for example, G.C. Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, Weed Control Handbook, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

Agrochemical preparations usually contain from 0.1 to 99 wt.%, in particular from 0.1 to 95 wt.% of the compounds according to the invention.

In wettable powders, the concentration of the active compound is, for example, from about 10 to 90 wt.%, and the rest, consisting of the usual components of the composition, up to 100 wt.%. In emulsifiable concentrates, the concentration of the active compound may be from 1 to 90% by weight, preferably from 5 to 80% by weight. Dusting-type compositions contain from 1 to 30% by weight of the active ingredient, preferably usually from 5 to 20% by weight of the active ingredient; spray solutions contain from about 0.05 to 80 wt.%, preferably from 2 to 50 wt.% of the active ingredient. In the case of water-dispersible granules, the content of the active compound depends in part on whether the active compound is in liquid or solid form and on which granulating aids, excipients, etc. are used. In water-dispersible granules, the active compound content is, for example, from 1 to 95% by weight, preferably from 10 to 80% by weight.

In addition, said active compound formulations optionally contain appropriate conventional adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors, and agents that affect pH and viscosity.

Based on these compositions, it is also possible to obtain combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, as well as safeners, fertilizers and/or growth regulators, for example in the form of a ready-made composition or as a tank mix.

Active compounds which can be used in combination with compounds according to the invention in mixed formulations or tank mix are, for example, known active compounds which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3- phosphate synthase, glutamine synthetase, phydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or The Pesticide Manual, ^15th edition, British Crop Protection Council and Royal Soc. of Chemistry, 2009, and the literature cited there. Examples of known herbicides or plant growth regulators that can be combined with the compounds of the invention include the following active ingredients (compounds are referred to by the common name according to the International Organization for Standardization (ISO) or chemical name or code number) and always cover all forms used, such as acids, salts, esters and isomers such as stereoisomers and optical isomers. These include, by way of example, one form of use, and in some cases also many forms of use: acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametrin Amicarbazon, amidzhlor, amidosulopuron, aminocyclopyrylor, aminopiralid, amitrol, sulfamate ammonium, Antsimonyel, anilophos, asulas, atrazin, azaphenidine, azimisulfuron, aziprine, beenazolin, Benazolin, benchonalin, benfluralin, Benfluralin. methyl, bentazon, benzfendizone, benzobicyclone, benzofenap, benzofluor, benzoylprop, bicyclopyrone, bifenox, bilanafos, bilanafos sodium, bispyribac, bispyribac sodium, bromocil, bromobutide, bromophenoxime, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butamifenacil, butenachlor, butralin, butroxydim, butylate, cafenstrol, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxifene, chloramben, chlorazifop, chlorazifop-bu til, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorphthalim, chlorthal-dimethyl, chlortoluron, chlorsulfuron, cynidone, cynidone-ethyl, cinmethylin, cinosulfuron, cletodym, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumiluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cyclooxydim, cycluron, cyhalofop-butyl, cyperquat, ciprazine, ciprazole, 2,4-D, 2,4-DB, daimuron/dimron, dalapon, daminoside, dazomet, n-decanol, desmedipham, desmetrin, detosyl pyrazolate (DTP), diallate, dicamba, dichlobenil, dichlorprop , Dichlorprop-R, Diclofop, Diclofop-methyl, Diclofop-R-methyl, Diclosulam, Dietatyl, Dietatyl-ethyl, Difenoxuron, Difenzocquat, Diflufenican, Diflufenzopyr, Diflufenzopyr Sodium, Dimefuron, Dikegulac Sodium, Dimepiperate, Dimethachlor, Dimethamethrin, Dimethenamide , dimethenamid-R, d imetipine, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamide, dipropetrin, diquat, diquat-dibromide, dithiopyr, diuron,

- 9 040923

DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, etametsulfuron, etametsulfuronmethyl, ethephon, etidimuron, etiosin, etofumesate, ethoxyphene, ethoxyphen-ethyl, ethoxysulfuron, etobenzanide, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1yl]phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoprop, fenoxaprop, fenoxaprop-R, fenoxaprop-ethyl, fenoxaprop-R-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop, flamprop-Misopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-R, fluazifopbutyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetraline, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, flumipropine, fluometuron, fluorodifen, fluoroglycofen, flulupoxacyl-ethyl, , flupropanate, flupyrsulfuron, flupyrsulfuron-methyl sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, flutiacet, flutiacet-methyl, flutiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, glufosinate, ammonium glufosinate, glufosinate-R, glufosin at-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl isopropylphosphoramidothioate, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-R, haloxyfop-ethoxyethyl, haloxifop-Rethoxyethyl, haloxifop-methyl, haloxyfop-R-methyl , hexazinon, HW-02, i.e. 1(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, imazametabenz-methyl, imazamox, imazamox-ammonium, imazapik, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapir, imazethapyr-ammonium, imazosesulfuron, inabenfid, indanophane, indaziflam, indoleacetic acid (IAA), 4-indole 3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone, isocarbamide, isopropaline, isoproturon, isouron, isoxaben, isoxachlorotol, isoxaflutol, isoxapirifop, KUH -043 i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1Hpyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, carbutylate, 1H, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCRV, MCRV-methyl, -ethyl and -sodium, mecoprop, mecopropate-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium , mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, metabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazasulfuron, metazol, methiopyrsulfuron, methiozolin, methoxyphenone , methyldymron, 1methylcyclopropene, methylisothiocyanate, methobenzuron, metobromuron, metolachlor, S-metolachlor, methosulam, methoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide, dihydrosulfate, monolinuron, monosulfuron, monosulfuron esters, MT, monosulfuron -128, i.e. 6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazin-3-amine, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, sodium nitrophenolate (mixture of isomers), nitrofluorfen, nonanoic acid, norflurazone, orbencarb, orthosulfamuron, oryzalin, oxadiargyl , oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paclobutrazol, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, petoxamide, fenizofam, phenmedifam, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pyrifenop, pyrifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazole, procyazine, prodiamine, prifluralin, proxidim, prohexadione, prohexadione-calcium, prohydrojasmone, promethone, promethrin, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propizamide, prosulfalin, prosulfocarb, prosulfuron, prinachlor, pyraclonil, pyrafluf ene, pyraflufen-ethyl, pyrafulfotol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyrifthalide, pyriminobac, pyriminobac-methyl, pyrite, pyrimibsulfan , pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamin, quizalofop, quizalofop-ethyl, quizalofop-R, quizalofop-R-ethyl, quizalofop-R-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetrin , SN-106279, i.e. methyl (2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2naphthyl}oxy)propanoate, sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium ), sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin- 4,5dione, tebutam, tebuthiuron, teknazen, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbutylazine, terbutrin, tenylchlor, thiafluamide, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone, thiencarbazone-tifensulfuron-methyl, thifensulfuron-methyl, thidiazuron methyl, thiobencarb, thiocarbazil, topramesone, tralkoxydim, triafamon, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridifan, tritazine, trifloxysulfuron, trifloxysulfuron sodium, trifluralin, triflusulfuron, triflu- 10 040923 sulfuron-methyl, trimeturon, trinexapak, trinexapak-ethyl, tritosulfuron, cytodef, uniconazole, uniconazole-R, vernolat, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2yl)oxy]benzyl}aniline, and the following compounds

ome ome

For use, formulations in commercial form are, if necessary, diluted in the conventional manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, with water. Dusting preparations, soil or spreading granules and spray solutions are generally not further diluted with other inert substances prior to use.

The required dose of application of the compounds of formula (I) depends on the external conditions, including, among other things, temperature, humidity and the type of herbicide used. It can vary within wide limits, for example from 0.001 to 1.0 kg/ha or more of active substance, but preferably from 0.005 to 750 g/ha.

The following examples illustrate the invention.

A. Chemical examples.

Preparation of 2,4-dichloro-6-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfanyl)benzamide (Ex. No. 2-242).

1. Obtaining 1,3-dichloro-5-fluoro-2-(methylsulfanyl)benzene.

Under a nitrogen atmosphere and at 0° C., 9.5 g (67 mmol) of methyl iodide are added to a mixture of 11.0 g (55.8 mmol) of 2,6-dichloro-4-fluorobenzenethiol and 11.6 g (84 mmol) of K ₂ CO ₃ in 50 ml DMF. After 12 hours of stirring at room temperature, the reaction mixture is poured onto ice and then extracted with t-butyl methyl ether. The organic phase is washed twice with water and once with sat. NaCl solution, dried over sodium sulfate and concentrated. Yield: 10.55 g (90%); slightly yellowish oil.

2. Obtaining 2,4-dichloro-6-fluoro-3-(methylsulfanyl)benzoic acid.

At -78° C., 20 ml (50 mmol) of a 2.5 M nBuLi solution are added dropwise to a solution of 10.55 g (50 mmol) of 1,3-dichloro-5-fluoro-2-(methylsulfanyl)benzoline in 100 ml of THF (abs). After stirring for 1 hour at -78° C., the mixture is passed through an excess of CO ₂ . Then the reaction mixture is allowed to warm to room temperature and poured into 500 ml of 1 M aqueous sodium hydroxide solution. The mixture is then washed with tert-butyl methyl ether. The aqueous phase is acidified to pH 4 using 2 M HCl solution and then extracted with tert-butyl methyl ether. The organic phase is dried over sodium sulfate, filtered and concentrated. Yield: 10 g (39 mmol; 78%).

1 H-NMR (40 MHz; DMSO-d6): 7.63 ppm. (d, 1H); 2.42 (s, 3H).

3. 2,4-Dichloro-6-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfanyl)benzamide (Note No. 2242).

At 0°C, 448 mg (0.309 ml, 3.53 mmol) of oxalyl chloride are added dropwise to a solution of 600 mg (2.35 mmol) of 2,4-dichloro-6-fluoro-3-(methylsulfanyl)benzoic acid and 326 mg ( 3.29 mmol) of 2-amino-5methyl-1,3,4-oxadiazole in 20 ml of pyridine. After 1 hour at 0° C., the reaction mixture is warmed to room temperature and stirred at room temperature for 14 hours. The mixture is then concentrated and 20 ml each of dichloromethane and water are added to the residue. After phase separation, the organic phase is dried over sodium sulfate, filtered and concentrated.

The residue is purified by column chromatography (silica gel, heptane/ethyl acetate).

Yield: 165 mg (purity 90%; 19%).

1H-NMR (40 MHz; DMSO-d ₆ ): 12.59 ppm. (bs, 1H), 7.86 ppm (d, 1H); 2.41 ppm (s, 3H).

Preparation of 2,4-dichloro-6-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfinyl)benzamide (note no. 2-243).

- 11 040923

At 0°C, 107 mg (0.465 mmol) of meta-chloroperbenzoic acid are added to a solution of 115 mg (0.274 mmol) of 2,4-dichloro-6-fluoro-X-(5-methyl-1,3,4-oxadiazol-2- yl)-3-(methylsulfanyl)benzamide (note no. 2242) in 20 ml of dichloromethane. After 2 days of stirring at room temperature, an aqueous solution of bisulfite is added. After extraction, the organic phase is concentrated and purified by column chromatography (HPLC; acetonitrile/water).

Yield: 32 mg (purity 95%; 31%).

¹ H-NMR (40 MHz; DMSO-d ₆ ): 11.60 ppm. (bs, 1H), 7.24 ppm (d, 1H), 3.07 ppm (s, 3H).

The abbreviations used mean:

Et = ethyl Me = methyl p-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl Ph = phenyl Ac = acetyl Bz = benzoyl

Table 1

Compounds of general formula (I) in which A is CY, W is fluorine and V and R are hydrogen

No. X Y z Physical data ('n-nmr, dmso-a ₆ , 400 MHz) 1-1 F H Cl 1-2 F H SO ₂ Me 1-3 F H SO ₂ Et 1-4 F H _CF3 1-5 F H no ₂ 1-6 C1 H Br 1-7 C1 H SMe 1-8 C1 H SOM 1-9 C1 H SO ₂ Me 1-10 C1 H SO ₂ CH ₂ C1 1-11 C1 H SEt 1-12 C1 H SO ₂ Et 1-13 C1 H _CF3 1-14 C1 H no ₂ 1-15 C1 H pyrazole-1- IL 1-16 C1 H 1H-1,2,4triazole-1- IL 1-17 Tue H Cl 1-18 Tue H Br 1-19 Tue H SO ₂ Me 1-20 Tue H SO ₂ Et 1-21 Tue H _CF3 1-22 SO ₂ Me H Cl 1-23 SO ₂ Me H Br 1-24 SO ₂ Me H SMe 1-25 SO ₂ Me H SOM 1-26 SO ₂ Me H SO ₂ Me 1-27 SO ₂ Me H SO ₂ Et 1-28 SO ₂ Me H _CF3 1-29 SO ₂ Et H Cl 1-30 SO ₂ Et H Br 1-31 SO ₂ Et H SMe 1-32 SO ₂ Et H SOM 1-33 SO ₂ Et H SO ₂ Me 1-34 SO ₂ Et H _CF3 1-35 NO ₂ H F 1-36 no ₂ H Cl 1-37 no ₂ H Br 1-38 no ₂ H I 1-39 no ₂ H CN 1-40 no ₂ H SO ₂ Me 1-41 no ₂ H SO ₂ Et

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1-42 no ₂ H _CF3 1-43 Me H Cl 1-44 Me H Br 1-45 Me H SMe 1-46 Me H SO ₂ Me 1-47 Me H SO ₂ CH ₂ C1 1-48 Me H SEt 1-49 Me H SO ₂ Et 1-50 Me H _CF3 1-51 CH ₂ SO ₂ Me H _CF3 1-52 Et H Cl 1-53 Et H Br 1-54 Et H SMe 1-55 Et H SO ₂ Me 1-56 Et H SO ₂ CH ₂ C1 1-57 Et H SEt 1-58 Et H SO ₂ Et 1-59 Et H _CF3 1-60 _CF3 H Cl 1-61 _CF3 H Br 1-62 _CF3 H SO ₂ Me 1-63 _CF3 H SO ₂ Et 1-64 _CF3 H _CF3 1-65 no ₂ hh ₂ F 1-66 no ₂ NHMe F 1-67 no ₂ NMe ₂ F 1-68 no ₂ Me Cl 1-69 no ₂ hh ₂ Cl 1-70 no ₂ NHMe Cl 1-71 no ₂ NMe ₂ Cl 1-72 no ₂ hh ₂ Br 1-73 no ₂ NHMe Br 1-74 no ₂ NMe ₂ Br 1-75 no _{2 NH2 CF3} 1-76 no ₂ NMe _{2 CF3} 1-77 no ₂ hh ₂ SO ₂ Me 1-78 no ₂ hh ₂ SO ₂ Et 1-79 no ₂ NHMe SO ₂ Me 1-80 no ₂ NMe ₂ SO ₂ Me 1-81 no ₂ NMe ₂ SO ₂ Et 1-82 no ₂ hh ₂ 1H-1,2,4triazole-1- IL 1-83 no ₂ NHMe Sh-1,2,4- triazole- 1- IL 1-84 no ₂ NMe ₂ 1H-1,2,4- triazole- 1- IL 1-85 Me SMe H 1-86 Me SOM H 1-87 Me SO ₂ Me H 1-88 Me SEt H

- 13 040923

1-89 Me SOEt H 1-90 Me SO ₂ Et H 1-91 Me S(CH ₂ ) ₂ OMe H 1-92 Me SO(CH ₂ ) ₂ OMe H 1-93 Me SO ₂ (CH ₂ ) ₂ OMe H 1-94 Me F F 1-95 Me F Cl 1-96 Me SEt F 1-97 Me SOEt F 1-98 Me SO ₂ Et F 1-99 Me Me Cl 1-100 Me F Cl 1-101 Me Cl Cl 1-102 Me hh ₂ Cl 1-103 Me NHMe Cl 1-104 Me NMe ₂ Cl 1-105 Me O(CH ₂ ) ₂ OMe Cl 1-106 Me O(CH ₂ ) ₃ OMe Cl 1-107 Me O( _CH2 ) _4OMe Cl 1-108 Me OCH ₂ CONMe ₂ Cl 1-109 Me O(CH ₂ ) ₂ -CO-NMe ₂ Cl 1-110 Me O(CH ₂ ) ₂ - NH(C0)NMe ₂ Cl 1-111 Me O(CH ₂ ) ₂ - NH(CO)NHCO ₂ Et Cl 1-112 Me O(CH ₂ ) ₂ -NHCO ₂ Me Cl 1-113 Me OCH ₂ -NHSO ₂ cPr Cl 1-114 Me O(CH ₂ )-5-2,4dimethyl-2,4dihydro-3H-1,2,4triazol-3-one Cl 1-115 Me O(CH ₂ )-3,5dimethyl-1,2oxazol-4-yl Cl 1-116 Me SMe Cl 1-117 Me SOM Cl 1-118 Me SO ₂ Me Cl 1-119 Me SEt Cl 1-120 Me SOEt Cl 1-121 Me SO ₂ Et Cl 1-122 Me S(CH ₂ ) ₂ OMe Cl 1-123 Me SO(CH ₂ ) ₂ OMe Cl 1-124 Me SO ₂ (CH ₂ ) ₂ OMe Cl 1-125 Me hh ₂ Br 1-126 Me NHMe Br 1-127 Me NMe ₂ Br

- 14 040923

1-128 Me OCH ₂ (CO)NMe ₂ Br 1-129 Me O(CH ₂ )-5pyrrolidin-2-one Br 1-130 Me SMe Br 1-131 Me SOM Br 1-132 Me SO ₂ Me Br 1-133 Me SEt Br 1-134 Me SOEt Br 1-135 Me SO ₂ Et Br 1-136 Me SMe I 1-137 Me SOM I 1-138 Me SO ₂ Me I 1-139 Me SEt I 1-140 Me SOEt I 1-141 Me SO ₂ Et I 1-142 Me Cl _CF3 1-143 Me SMe _CF3 1-144 Me SOM _CF3 1-145 Me SO ₂ Me _CF3 1-146 Me SEt _CF3 1-147 Me SOEt _CF3 1-148 Me SO ₂ Et _CF3 1-149 Me S(CH ₂ ) ₂ OMe _CF3 1-150 Me SO(CH ₂ ) ₂ OMe _CF3 1-151 Me SO ₂ (CH ₂ ) ₂ OMe _CF3 1-152 Me Me SO ₂ Me 1-153 Me 4,5-dihydro-1,2oxazol-3-yl SO ₂ Me 1-154 Me 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 1-155 Me 5-cyanomethyl-4,5dihydro-1,2oxazol-3-yl SO ₂ Me 1-156 Me 5-cyanomethyl-4,5- dihydro-1,2- oxazol-3-yl SO ₂ Et 1-157 Me hh ₂ SO ₂ Me 1-158 Me NHMe SO ₂ Me 1-159 Me NMe ₂ SO ₂ Me 1-160 Me NH(CH ₂ ) ₂ OMe SO ₂ Me 1-161 Me pyrazol-1-yl SO ₂ Me 1-162 Me HE SO ₂ Me 1-163 Me OME SO ₂ Me 1-164 Me OME SO ₂ Et 1-165 Me OEt SO ₂ Me 1-166 Me OEt SO ₂ Et

- 15 040923

1-167 Me Oipr SO ₂ Me 1-168 Me Oipr SO ₂ Et 1-169 Me O(CH ₂ ) ₂ OMe SO ₂ Me 1-170 Me O(CH ₂ ) ₂ OMe SO ₂ Et 1-171 Me O(CH ₂ ) ₃ OMe SO ₂ Me 1-172 Me O(CH ₂ ) ₃ OMe SO ₂ Et 1-173 Me O( _CH2 ) _4OMe SO ₂ Me 1-174 Me O( _CH2 ) _4OMe SO ₂ Et 1-175 Me O(CH ₂ ) ₂ NHSO2Me SO ₂ Me 1-176 Me O(CH ₂ ) ₂ NHSO2Me SO ₂ Et 1-177 Me OCH ₂ (CO)NMe ₂ SO ₂ Me 1-178 Me OCH ₂ (CO)NMe ₂ SO ₂ Et 1-179 Me [1,4]dioxan-2ylmethoxy SO ₂ Me 1-180 Me [1,4]dioxan-2ylmethoxy SO ₂ Et 1-181 Me O (CH ₂ ) ₂ -O- (3,5 dimethoxypyrimidin-2-yl) SO ₂ Me 1-182 Me C1 SO ₂ Me 1-183 Me SMe SO ₂ Me 1-184 Me SOM SO ₂ Me 1-185 Me SO ₂ Me SO ₂ Me 1-186 Me SO ₂ Me SO ₂ Et 1-187 Me SEt SO ₂ Me 1-188 Me SOEt SO ₂ Me 1-189 Me SO ₂ Et SO ₂ Me 1-190 Me S(CH ₂ ) ₂ OMe SO ₂ Me 1-191 Me SO(CH ₂ ) ₂ OMe SO ₂ Me 1-192 Me SO ₂ (CH ₂ ) ₂ OMe SO2Me 1-193 CH ₂ SMe ome SO ₂ Me 1-194 _CH2OMe ome SO ₂ Me 1-195 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OEt SO ₂ Me 1-196 CH ₂ O(CH ₂ ) ₂ OMe NH( _CH2 ) _3OEt SO ₂ Me 1-197 CH ₂ O (CH ₂ ) ₃ OMe ome SO ₂ Me 1-198 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OMe SO ₂ Me 1-199 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) _3OMe SO ₂ Me 1-200 Et SMe Cl 1-201 Et SO ₂ Me Cl 1-202 Et SMe _CF3 1-203 Et SO ₂ Me _CF3

- 16 040923

1-204 Et F SO ₂ Me 1-205 Et NH(CH ₂ ) ₂ OMe SO ₂ Me 1-206 IPr SO ₂ Me _CF3 1-207 cPr SO ₂ Me _CF3 1-208 _CF3 O(CH ₂ ) ₂ OMe F 1-209 _CF3 O(CH ₂ ) ₃ OMe F 1-210 _CF3 OCH ₂ CONMe ₂ F 1-211 _CF3 [1,4]dioxan-2ylmethoxy F 1-212 _CF3 O(CH ₂ ) ₂ OMe Cl 1-213 _CF3 O(CH ₂ ) ₃ OMe Cl 1-214 _CF3 OCH ₂ CONMe ₂ Cl 1-215 _CF3 [1,4]dioxan-2ylmethoxy Cl 1-216 _CF3 O (CH ₂ ) ₂ OMe Br 1-217 _CF3 O (CH ₂ ) ₃ OMe Br 1-218 _CF3 OCH ₂ CONMe ₂ Br 1-219 _CF3 [1,4]dioxan-2ylmethoxy Br 1-220 _CF3 O (CH ₂ ) ₂ OMe I 1-221 _CF3 O (CH ₂ ) ₃ OMe I 1-222 _CF3 OCH ₂ CONMe ₂ I 1-223 _CF3 [1,4]dioxan-2ylmethoxy I 1-224 _CF3 F SO ₂ Me 1-225 _CF3 F SO ₂ Et 1-226 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Me 1-227 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Et 1-228 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Me 1-229 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Et 1-230 _CF3 OCH ₂ CONMe ₂ SO ₂ Me 1-231 _CF3 OCH ₂ CONMe ₂ SO ₂ Et 1-232 _CF3 [1,4]dioxane-2- ylmethoxy SO ₂ Me 1-233 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Et 1-234 F SMe _CF3 1-235 F SOM _CF3 1-236 Cl Me Cl 1-237 Cl DOS ₂ SNSN ₂ Cl 1-238 Cl OCH ₂ CHF ₂ Cl 1-239 Cl O (CH ₂ ) ₂ OMe Cl 1-240 Cl OCH ₂ CONMe ₂ Cl 1-241 Cl O (CH ₂ ) -5pyrrolidin-2-one Cl 1-242 Cl SMe Cl

- 17 040923

1-243 Cl SOM C1 1-244 Cl SO ₂ Me C1 1-245 Cl F SMe 1-246 Cl Cl SO ₂ Me 1-247 Cl COOMe SO ₂ Me 1-248 Cl CONMe ₂ SO ₂ Me 1-249 Cl CONMe(OMe) SO ₂ Me 1-250 Cl _CH2OMe SO ₂ Me 1-251 Cl _CH2OMe SO ₂ Et 1-252 Cl _CH2OEt SO ₂ Me 1-253 Cl _CH2OEt SO ₂ Et 1-254 Cl CH ₂ OCH ₂ CHF ₂ SO ₂ Me 1-255 Cl ch ₂ och ₂ cf ₃ SO ₂ Me 1-256 Cl ch ₂ och ₂ cf ₃ SO ₂ Et 1-257 Cl ch ₂ och ₂ cf ₂ chf ₂ SO ₂ Me 1-258 Cl CH ₂ O-s-pentyl SO ₂ Me 1-259 Cl _CH2PO (OMe) ₂ SO ₂ Me 1-260 Cl 4,5-dihydro-1,2- oxazol-3-yl SMe 1-261 Cl 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Me 1-262 Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 1-263 Cl 5-cyanomethyl- 4,5- dihydro-1,2- oxazol-3-yl SO ₂ Me 1-264 Cl 5-cyanomethyl- 4,5- dihydro-1,2- oxazol-3-yl SO ₂ Et 1-265 Cl 5-(methoxymethyl)- 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et 1-266 Cl 5-(methoxymethyl)-5methyl-4,5-dihydro1,2-oxazol-3-yl SO ₂ Et 1-267 Cl CH ₂ Otetrahydrofuran-3 yl SO ₂ Me 1-268 Cl CH ₂ Otetrahydrofuran-3 yl SO ₂ Et 1-269 Cl CH ₂ OCH ₂ tetrahydrofuran-2yl SO ₂ Me

- 18 040923

1-270 Cl CH ₂ OCH ₂ tetrahydrofuran-2- IL SO ₂ Et 1-271 Cl CH ₂ OCH ₂ tetrahydrofuran-3 yl SO ₂ Me 1-272 Cl CH ₂ OCH ₂ tetrahydrofuran-3 yl SO ₂ Et 1-273 Cl OME SO ₂ Me 1-274 Cl OME SO ₂ Et 1-275 Cl OEt SO ₂ Me 1-276 Cl OEt SO ₂ Et 1-277 Cl Oipr SO ₂ Me 1-278 Cl Oipr SO ₂ Et 1-279 Cl O(CH ₂ ) ₂ OMe SO ₂ Me 1-280 Cl O( _CH2 ) _4OMe SO ₂ Me 1-281 Cl O (CH ₂ ) ₄ OMe SO ₂ Et 1-282 Cl O (CH ₂ ) ₃ OMe SO ₂ Me 1-283 Cl O (CH ₂ ) ₃ OMe SO ₂ Et 1-284 Cl O (CH ₂ ) ₂ OMe SO ₂ Me 1-285 Cl O (CH ₂ ) ₂ OMe SO ₂ Et 1-286 Cl [1,4]dioxan-2ylmethoxy SO ₂ Me 1-287 Cl [1,4]dioxan-2ylmethoxy SO ₂ Et 1-288 Cl OCH ₂ (CO)NMe ₂ SO ₂ Me 1-289 Cl OCH ₂ (CO)NMe ₂ SO ₂ Et 1-290 Cl SMe SO ₂ Me 1-291 Cl SOM SO ₂ Me 1-292 Br OME Br 1-293 Br O(CH ₂ ) ₂ OMe Br 1-294 Br O (CH ₂ ) ₂ OMe SO ₂ Me 1-295 Br O (CH ₂ ) ₂ OMe SO ₂ Et 1-296 Br O (CH ₂ ) ₃ OMe SO ₂ Me 1-297 Br O (CH ₂ ) ₃ OMe SO ₂ Et 1-298 Br O (CH ₂ ) ₄ OMe SO ₂ Me 1-299 Br O (CH ₂ ) ₄ OMe SO ₂ Et 1-300 Br [1,4]dioxan-2ylmethoxy SO ₂ Me 1-301 Br [1,4]dioxan-2ylmethoxy SO ₂ Et 1-302 I O (CH ₂ ) ₂ OMe SO ₂ Me 1-303 I O (CH ₂ ) ₂ OMe SO ₂ Et 1-304 I O (CH ₂ ) ₃ OMe SO ₂ Me 1-305 I O (CH ₂ ) ₃ OMe SO ₂ Et

- 19 040923

1-306 I O( _CH2 ) _4OMe SO ₂ Me 1-307 I O( _CH2 ) _4OMe SO ₂ Et 1-308 I [1,4]dioxan-2ylmethoxy SO ₂ Me 1-309 I [1,4]dioxan-2ylmethoxy SO ₂ Et 1-310 ome SMe _CF3 1-311 ome SOM _CF3 1-312 ome SO ₂ Me _CF3 1-313 ome SOEt _CF3 1-314 ome SO ₂ Et _CF3 1-315 ome S(CH ₂ ) ₂ OMe _CF3 1-316 ome SO(CH ₂ ) ₂ OMe _CF3 1-317 ome SO ₂ (CH ₂ ) ₂ OMe _CF3 1-318 ome SMe Cl 1-319 ome SOM Cl 1-320 ome SO ₂ Me Cl 1-321 ome SEt Cl 1-322 ome SOEt Cl 1-323 ome S02Et Cl 1-324 ome S(CH ₂ ) ₂ OMe Cl 1-325 ome SO(CH ₂ ) ₂ OMe Cl 1-326 ome SO ₂ (CH ₂ ) ₂ OMe Cl 1-327 OCH ₂ c-Pr SMe _CF3 1-328 OCH ₂ c-Pr SOM _CF3 1-329 OCH ₂ c-Pr SO ₂ Me _CF3 1-330 OCH ₂ c-Pr SEt _CF3 1-331 OCH ₂ c-Pr SOEt _CF3 1-332 OCH ₂ c-Pr SO ₂ Et _CF3 1-333 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe _CF3 1-334 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe _CF3 1-335 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe _CF3 1-336 OCH ₂ c-Pr SMe Cl 1-337 OCH ₂ c-Pr SOM Cl 1-338 OCH ₂ c-Pr SO ₂ Me Cl 1-339 OCH ₂ c-Pr SEt Cl 1-340 OCH ₂ c-Pr SOEt Cl 1-341 OCH ₂ c-Pr SO ₂ Et Cl 1-342 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe Cl 1-343 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe Cl 1-344 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe Cl 1-345 OCH ₂ c-Pr SMe SO ₂ Me 1-346 OCH ₂ c-Pr SOM SO ₂ Me 1-347 OCH ₂ c-Pr SO ₂ Me SO ₂ Me 1-348 OCH ₂ c-Pr SEt SO ₂ Me 1-349 OCH ₂ c-Pr SOEt SO ₂ Me 1-350 OCH ₂ c-Pr SO ₂ Et SO ₂ Me 1-351 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe SO ₂ Me 1-352 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe SO ₂ Me 1-353 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe SO ₂ Me 1-354 SO ₂ Me F _CF3 1-355 SO ₂ Me hh _{2 CF3} 1-356 SO ₂ Me NHEt Cl 1-357 SMe SEt F 1-358 SMe SMe F 1-359 Cl SMe _CF3 1-360 Cl S(O)Me _CF3 1-361 Cl SO ₂ Me _CF3 1-362 Cl SO ₂ Me SO ₂ Me

- 20 040923

table 2

Compounds of general formula (I) in which A is CY, V is hydrogen, W is fluorine and R is methyl

No. X Y z Physical Data CH-nmr, DMSOde, 400 MHz) 2-1 F H Cl 2-2 F H SO ₂ Me 2-3 F H SO ₂ Et 2-4 F H _CF3 2-5 F H no ₂ 2-6 C1 H Br 2-7 C1 H SMe 2-8 C1 H SOM 2-9 C1 H SO ₂ Me 2-10 C1 H SO ₂ CH ₂ C1 2-11 C1 H SEt 2-12 C1 H SO ₂ Et 2-13 C1 H _CF3 2-14 C1 H no ₂ 2-15 C1 H pyrazol-1-yl 2-16 C1 H 1H-1,2,4triazol-1-yl 2-17 Vg H Cl 2-18 Vg H Br 2-19 Vg H SO ₂ Me 2-20 Vg H SO ₂ Et 2-21 Vg H _CF3 2-22 SO ₂ Me H Cl 2-23 SO ₂ Me H Br 2-24 SO ₂ Me H SMe 2-25 SO ₂ Me H SOM 2-26 SO ₂ Me H SO ₂ Me 2-27 SO ₂ Me H SO ₂ Et 2-28 SO ₂ Me H _CF3 2-29 SO ₂ Et H Cl 2-30 SO ₂ Et H Br 2-31 SO ₂ Et H SMe 2-32 SO ₂ Et H SOM 2-33 SO ₂ Et H SO ₂ Me 2-34 SO ₂ Et H _CF3 2-35 no ₂ H F 2-36 no ₂ H Cl 2-37 no ₂ H Br 2-38 no ₂ H I 2-39 no ₂ H CN 2-40 no ₂ H SO ₂ Me 2-41 no ₂ H SO ₂ Et 2-42 no ₂ H _CF3 2-43 Me H Cl 2-44 Me H Br 2-45 Me H SMe 2-46 Me H SO ₂ Me 2-47 Me H SO ₂ CH ₂ C1 2-48 Me H SEt 2-49 Me H SO ₂ Et 2-50 Me H _CF3 2-51 CH ₂ SO ₂ Me H _CF3 2-52 Et H Cl 2-53 Et H Br 2-54 Et H SMe 2-55 Et H SO ₂ Me 2-56 Et H SO ₂ CH ₂ C1 2-57 Et H SEt 2-58 Et H SO ₂ Et

- 21 040923

2-59 Et H _CF3 2-60 _CF3 H Cl 2-61 _CF3 H Br 2-62 _CF3 H SO ₂ Me 2-63 _CF3 H SO ₂ Et 2-64 _CF3 H _CF3 2-65 no ₂ hh ₂ F 2-66 no ₂ NHMe F 2-67 no ₂ NMe ₂ F 2-68 no ₂ Me Cl 2-69 no ₂ hh ₂ Cl 2-70 no ₂ NHMe Cl 2-71 no ₂ NMe ₂ Cl 2-72 no ₂ hh ₂ Br 2-73 no ₂ NHMe Br 2-74 no ₂ NMe ₂ Br 2-75 no ₂ hh _{2 CF3} 2-76 no ₂ NMe _{2 CF3} 2-77 no ₂ hh ₂ SO ₂ Me 2-78 no ₂ hh ₂ SO ₂ Et 2-79 no ₂ NHMe SO ₂ Me 2-80 no ₂ NMe ₂ SO ₂ Me 2-81 no ₂ NMe ₂ SO ₂ Et 2-82 no ₂ hh ₂ 1H-1,2,4triazole-1-IL 2-83 no ₂ NHMe 1H-1,2,4triazol-1-yl 2-84 no ₂ NMe ₂ 1H-1,2,4triazol-1-yl 2-85 Me SMe Η 2-86 Me SOM Η 2-87 Me SO ₂ Me Η 2-88 Me SEt Η 2-89 Me SOEt Η 2-90 Me SO ₂ Et Η 2-91 Me S(CH ₂ ) ₂ OMe Η 2-92 Me SO(CH ₂ ) ₂ OMe Η 2-93 Me SO ₂ (CH ₂ ) ₂ OMe Η 2-94 Me F F 2-95 Me F C1 2-96 Me SEt F 2-97 Me SOEt F 2-98 Me SO ₂ Et F 2-99 Me Me C1 2-100 Me F C1

- 22 040923

2-101 Me Cl Cl 2-102 Me hh ₂ Cl 2-103 Me NHMe Cl 2-104 Me NMe ₂ Cl 2-105 Me O(CH ₂ ) ₂ OMe Cl 2-106 Me O(CH ₂ ) ₃ OMe Cl 2-107 Me O( _CH2 ) _4OMe Cl 2-108 Me OCH ₂ CONMe ₂ Cl 2-109 Me O(CH ₂ ) ₂ -CO- NMe ₂ Cl 2-110 Me O(CH ₂ ) ₂ NH(CO)NMe ₂ Cl 2-111 Me O(CH ₂ ) ₂ NH(CO)NHCO ₂ Et Cl 2-112 Me O(CH ₂ ) ₂ - NHCO ₂ Me Cl 2-113 Me O-CH ₂ - NHSO ₂ cPr Cl 2-114 Me O(CH ₂ ) -5-2,4dimethyl-2,4dihydro-3H1,2,4-triazole-zone Cl 2-115 Me O (CH ₂ ) -3,5dimethyl-1,2oxazol-4-yl Cl 2-116 Me SMe Cl 2-117 Me SOM Cl 2-118 Me SO ₂ Me Cl 2-119 Me SEt Cl 2-120 Me SOEt Cl 2-121 Me SO ₂ Et Cl 2-122 Me S(CH ₂ ) ₂ OMe Cl 2-123 Me SO(CH ₂ ) ₂ OMe Cl 2-124 Me SO ₂ (CH ₂ ) ₂ OMe Cl 2-125 2-126 Me NHMe Br 2-127 Me NMe ₂ Br 2-128 Me O(CH ₂ )CONEt ₂ Br 2-129 Me O(CH ₂ )-5pyrrolidin-2-one Br 2-130 Me SMe Br 2-131 Me SOM Br 2-132 Me SO ₂ Me Br 2-133 Me SEt Br

- 23 040923

2-134 Me SOEt Vg 2-135 Me SO ₂ Et Vg 2-136 Me SMe I 2-137 Me SOM I 2-138 Me SO ₂ Me I 2-139 Me SEt I 2-140 Me SOEt I 2-141 Me SO ₂ Et I 2-142 Me Cl _CF3 2-143 Me SMe _CF3 2-144 Me SOM _CF3 2-145 Me SO ₂ Me _CF3 2-146 Me SEt _CF3 2-147 Me SOEt _CF3 2-148 Me SO ₂ Et _CF3 2-149 Me S(CH ₂ ) ₂ OMe _CF3 2-150 Me SO(CH ₂ ) ₂ OMe _CF3 2-151 Me SO ₂ (CH ₂ ) ₂ OMe _CF3 2-152 Me Me SO ₂ Me 2-153 Me 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Me 2-154 Me 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 2-155 Me 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Me 2-156 Me 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 2-157 Me hh ₂ SO ₂ Me 2-158 Me NHMe SO ₂ Me 2-159 Me NMe ₂ SO ₂ Me 2-160 Me NH(CH ₂ ) ₂ OMe SO ₂ Me 2-161 Me pyrazol-1-yl SO ₂ Me 2-162 Me HE SO ₂ Me 2-163 Me OME SO ₂ Me 2-164 Me OME SO ₂ Et 2-165 Me OEt SO ₂ Me 2-166 Me OEt SO ₂ Et 2-167 Me Oipr SO ₂ Me 2-168 Me Oipr SO ₂ Et 2-169 Me O(CH ₂ ) ₂ OMe SO ₂ Me 2-170 Me O(CH ₂ ) ₂ OMe SO ₂ Et 2-171 Me O (CH ₂ ) ₃ OMe SO ₂ Me 2-172 Me O (CH ₂ ) ₃ OMe SO ₂ Et

- 24 040923

2-173 Me O( _CH2 ) _4OMe SO ₂ Me 2-174 Me O( _CH2 ) _4OMe SO ₂ Et 2-175 Me O(CH ₂ ) ₂ NHSO2 Me SO ₂ Me 2-176 Me O(CH ₂ ) ₂ NHSO2 Me SO ₂ Et 2-177 Me OCH ₂ (CO)NMe ₂ SO ₂ Me 2-178 Me OCH ₂ (CO)NMe ₂ SO ₂ Et 2-179 Me [1,4]dioxan-2ylmethoxy SO ₂ Me 2-180 Me [1,4]dioxan-2ylmethoxy SO ₂ Et 2-181 Me O (CH ₂ ) ₂ -O- (3,5 dimethoxypyrimidin-2yl) SO ₂ Me 2-182 Me C1 SO ₂ Me 2-183 Me SMe SO ₂ Me 2-184 Me SOM SO ₂ Me 2-185 Me SO ₂ Me SO ₂ Me 2-186 Me SO ₂ Me SO ₂ Et 2-187 Me SEt SO ₂ Me 2-188 Me SOEt SO ₂ Me 2-189 Me SO ₂ Et SO ₂ Me 2-190 Me S(CH ₂ ) ₂ OMe SO ₂ Me 2-191 Me SO(CH ₂ ) ₂ OMe SO ₂ Me 2-192 Me SO ₂ (CH ₂ ) ₂ OMe SO2Me 2-193 CH ₂ SMe ome SO ₂ Me 2-194 _CH2OMe ome SO ₂ Me 2-195 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OEt SO ₂ Me 2-196 CH ₂ O(CH ₂ ) ₂ OMe NH( _CH2 ) _3OEt SO ₂ Me 2-197 CH ₂ O (CH ₂ ) ₃ OMe ome SO ₂ Me 2-198 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OMe SO ₂ Me 2-199 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) _3OMe SO ₂ Me 2-200 Et SMe Cl 2-201 Et SO ₂ Me Cl 2-202 Et SMe _CF3 2-203 Et SO ₂ Me _CF3 2-204 Et F SO ₂ Me 2-205 Et NH(CH ₂ ) ₂ OMe SO ₂ Me

- 25 040923

2-206 IPr SO ₂ Me _CF3 2-207 cPr SO ₂ Me _CF3 2-208 _CF3 O(CH ₂ ) ₂ OMe F 2-209 _CF3 O(CH ₂ ) ₃ OMe F 2-210 _CF3 OCH ₂ CONMe ₂ F 2-211 _CF3 [1,4]dioxan-2ylmethoxy F 2-212 _CF3 O(CH ₂ ) ₂ OMe Cl 2-213 _CF3 O(CH ₂ ) ₃ OMe Cl 2-214 _CF3 OCH ₂ CONMe ₂ Cl 2-215 _CF3 [1,4]dioxan-2ylmethoxy Cl 2-216 _CF3 O (CH ₂ ) ₂ OMe Br 2-217 _CF3 O (CH ₂ ) ₃ OMe Br 2-218 _CF3 OCH ₂ CONMe ₂ Br 2-219 _CF3 [1,4]dioxan-2ylmethoxy Br 2-220 _CF3 O (CH ₂ ) ₂ OMe I 2-221 _CF3 O (CH ₂ ) ₃ OMe I 2-222 _CF3 OCH ₂ CONMe ₂ I 2-223 _CF3 [1,4]dioxan-2ylmethoxy I 2-224 _CF3 F SO ₂ Me 2-225 _CF3 F SO ₂ Et 2-226 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Me 2-227 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Et 2-228 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Me 2-229 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Et 2-230 _CF3 OCH ₂ CONMe ₂ SO ₂ Me 2-231 _CF3 OCH ₂ CONMe ₂ SO ₂ Et 2-232 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Me 2-233 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Et 2-234 F SMe _CF3 2-235 F SOM _CF3 2-236 Cl Me Cl 2-237 Cl DOS ₂ SNSN ₂ Cl 2-238 Cl OCH ₂ CHF ₂ Cl 2-239 Cl O (CH ₂ ) ₂ OMe Cl 2-240 Cl OCH ₂ (CO)NMe ₂ Cl 2-241 Cl O (CH ₂ ) -5pyrrolidin-2-one Cl 2-242 Cl SMe Cl 12.59 ppm (bs, 1H), 7.86 ppm (d, 1H);

- 26 040923

2.41 ppm (s, 3H). 2-243 Cl SOM C1 11.60 p.m. (bs, 1H), 7.24 ppm (d, 1H); 3.07 ppm (s, 3H). 2-244 Cl SO ₂ Me C1 2-245 Cl F SMe 2-246 Cl Cl SO ₂ Me 2-247 Cl COOMe SO ₂ Me 2-248 Cl CONMe ₂ SO ₂ Me 2-249 Cl CONMe(OMe) SO ₂ Me 2-250 Cl _CH2OMe SO ₂ Me 2-251 Cl _CH2OMe SO ₂ Et 2-252 Cl _CH2OEt SO ₂ Me 2-253 Cl _CH2OEt SO ₂ Et 2-254 Cl CH ₂ OCH ₂ CHF ₂ SO ₂ Me 2-255 Cl ch ₂ och ₂ cf ₃ SO ₂ Me 2-256 Cl ch ₂ och ₂ cf ₃ SO ₂ Et 2-257 Cl ch ₂ och ₂ cf ₂ ch f ₂ SO ₂ Me 2-258 Cl CH ₂ O-s-pentyl SO ₂ Me 2-259 Cl _CH2PO (OMe) ₂ SO ₂ Me 2-260 Cl 4,5-dihydro-1,2oxazol-3-yl SMe 2-261 Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Me 2-262 Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 2-263 Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Me 2-264 Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 2-265 Cl 5- (methoxymethyl)4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 2-266 Cl 5- (methoxymethyl)5-methyl-4,5dihydro-1,2oxazol-3-yl SO ₂ Et 2-267 Cl CH ₂ Otetrahydrofuran-3-yl SO ₂ Me

-27040923

2-268 Cl CH ₂ Tetrahydrofuran-3-yl SO ₂ Et 2-269 Cl CH ₂ OCH ₂ tetrahydrofuran-2-yl SO ₂ Me 2-270 Cl CH ₂ OCH ₂ tetrahydrofran-2-yl SO ₂ Et 2-271 Cl CH ₂ OCH ₂ tetrahydrofuran-3-yl SO ₂ Me 2-272 Cl CH ₂ OCH ₂ tetrahydrofuran-3-yl SO ₂ Et 2-273 Cl ome SO ₂ Me 2-274 Cl ome SO ₂ Et 2-275 Cl OEt SO ₂ Me 2-276 Cl OEt SO ₂ Et 2-277 Cl Oipr SO ₂ Me 2-278 Cl Oipr SO ₂ Et 2-279 Cl O(CH ₂ ) ₂ OMe SO ₂ Me 2-280 Cl O( _CH2 ) _4OMe SO ₂ Me 2-281 Cl O( _CH2 ) _4OMe SO ₂ Et 2-282 Cl O(CH ₂ ) ₃ OMe SO ₂ Me 2-283 Cl O(CH ₂ ) ₃ OMe SO ₂ Et 2-284 Cl O(CH ₂ ) ₂ OMe SO ₂ Me 2-285 Cl O(CH ₂ ) ₂ OMe SO ₂ Et 2-286 Cl [1,4]dioxan-2ylmethoxy SO ₂ Me 2-287 Cl [1,4]dioxan-2ylmethoxy SO ₂ Et 2-288 Cl OCH ₂ (CO)NMe ₂ SO ₂ Me 2-289 Cl OCH ₂ (CO)NMe ₂ SO ₂ Et 2-290 Cl SMe SO ₂ Me 2-291 Cl SOM SO ₂ Me 2-292 Br ome Br 2-293 Br O(CH ₂ ) ₂ OMe Br 2-294 Br O(CH ₂ ) ₂ OMe SO ₂ Me 2-295 Br O(CH ₂ ) ₂ OMe SO ₂ Et 2-296 Br O(CH ₂ ) ₃ OMe SO ₂ Me 2-297 Br O(CH ₂ ) ₃ OMe SO ₂ Et 2-298 Br O( _CH2 ) _4OMe SO ₂ Me 2-299 Br O( _CH2 ) _4OMe SO ₂ Et 2-300 Br [1,4]dioxane-2- SO ₂ Me

- 28 040923

ylmethoxy 2-301 Br [1,4]dioxan-2ylmethoxy SO ₂ Et 2-302 I O(CH ₂ ) ₂ OMe SO ₂ Me 2-303 I O (CH ₂ ) ₂ OMe SO ₂ Et 2-304 I O (CH ₂ ) ₃ OMe SO ₂ Me 2-305 I O (CH ₂ ) ₃ OMe SO ₂ Et 2-306 I O (CH ₂ ) ₄ OMe SO ₂ Me 2-307 I O (CH ₂ ) ₄ OMe SO ₂ Et 2-308 I [1,4]dioxan-2ylmethoxy SO ₂ Me 2-309 I [1,4]dioxan-2ylmethoxy SO ₂ Et 2-310 ome SMe _CF3 2-311 ome SOM _CF3 2-312 ome SO ₂ Me _CF3 2-313 ome SOEt _CF3 2-314 ome SO ₂ Et _CF3 2-315 ome S(CH ₂ ) ₂ OMe _CF3 2-316 ome SO(CH ₂ ) ₂ OMe _CF3 2-317 ome SO ₂ (CH ₂ ) ₂ OMe _CF3 2-318 ome SMe Cl 2-319 ome SOM Cl 2-320 ome SO ₂ Me Cl 2-321 ome SEt Cl 2-322 ome SOEt Cl 2-323 ome S02Et Cl 2-324 ome S(CH ₂ ) ₂ OMe Cl 2-325 ome SO(CH ₂ ) ₂ OMe Cl 2-326 ome SO ₂ (CH ₂ ) ₂ OMe Cl 2-327 OCH ₂ c-Pr SMe _CF3 2-328 OCH ₂ c-Pr SOM _CF3 2-329 OCH ₂ c-Pr SO ₂ Me _CF3 2-330 OCH ₂ c-Pr SEt _CF3 2-331 OCH ₂ c-Pr SOEt _CF3 2-332 OCH ₂ c-Pr SO ₂ Et _CF3 2-333 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe _CF3 2-334 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe _CF3 2-335 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe _CF3 2-336 OCH ₂ c-Pr SMe Cl 2-337 OCH ₂ c-Pr SOM Cl 2-338 OCH ₂ c-Pr SO ₂ Me Cl 2-339 OCH ₂ c-Pr SEt Cl 2-340 OCH ₂ c-Pr SOEt Cl 2-341 OCH ₂ c-Pr SO ₂ Et Cl 2-342 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe Cl 2-343 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe Cl 2-344 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe Cl 2-345 OCH ₂ c-Pr SMe SO ₂ Me 2-346 OCH ₂ c-Pr SOM SO ₂ Me 2-347 OCH ₂ c-Pr SO ₂ Me SO ₂ Me 2-348 OCH ₂ c-Pr SEt SO ₂ Me 2-349 OCH ₂ c-Pr SOEt SO ₂ Me 2-350 OCH ₂ c-Pr SO ₂ Et SO ₂ Me 2-351 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe SO ₂ Me 2-352 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe SO ₂ Me 2-353 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe SO ₂ Me 2-354 SO ₂ Me F _CF3 2-355 SO ₂ Me hh _{2 CF3} 2-356 SO ₂ Me NHEt Cl 2-357 SMe SEt F 2-358 SMe SMe F 2-359 Cl SMe _CF3 2-360 Cl S(O)Me _CF3 2-361 Cl SO ₂ Me _CF3 2-362 Cl SO ₂ Me SO ₂ Me

- 29 040923

Table 3

Compounds of general formula (I) in which A is CY,

V is hydrogen, W is fluorine and R is ethyl

No. X Y z Physical data Cn-nmr, dmso-a ₆ , 400 MHz) 3-1 F H Cl 3-2 F H SO ₂ Me 3-3 F H SO ₂ Et 3-4 F H _CF3 3-5 F H no ₂ 3-6 C1 H Br 3-7 C1 H SMe 3-8 C1 H SOM 3-9 C1 H SO ₂ Me 3-10 C1 H SO ₂ CH ₂ C1 3-11 C1 H SEt 3-12 C1 H SO ₂ Et 3-13 C1 H _CF3 3-14 C1 H no ₂ 3-15 C1 H pyrazol-1-yl 3-16 C1 H 1Н-1,2,4-triazol1-yl 3-17 Vg H Cl 3-18 Vg H Vg 3-19 Vg H SO ₂ Me 3-20 Vg H SO ₂ Et 3-21 Vg H _CF3 3-22 SO ₂ Me H Cl 3-23 SO ₂ Me H Br 3-24 SO ₂ Me H SMe 3-25 SO ₂ Me H SOM 3-26 SO ₂ Me H SO ₂ Me 3-27 SO ₂ Me H SO ₂ Et 3-28 SO ₂ Me H _CF3 3-29 SO ₂ Et H Cl 3-30 SO ₂ Et H Br 3-31 SO ₂ Et H SMe 3-32 SO ₂ Et H SOM 3-33 SO ₂ Et H SO ₂ Me 3-34 SO ₂ Et H _CF3 3-35 no ₂ H F 3-36 no ₂ H Cl 3-37 no ₂ H Br 3-38 no ₂ H I 3-39 no ₂ H CN 3-40 no ₂ H SO ₂ Me 3-41 no ₂ H SO ₂ Et 3-42 no ₂ H _CF3 3-43 Me H Cl 3-44 Me H Br 3-45 Me H SMe 3-46 Me H SO ₂ Me 3-47 Me H SO ₂ CH ₂ C1 3-48 Me H SEt 3-49 Me H SO ₂ Et 3-50 Me H _CF3

- 30 040923

3-51 CH ₂ SO ₂ Me H _CF3 3-52 Et H Cl 3-53 Et H Br 3-54 Et H SMe 3-55 Et H SO ₂ Me 3-56 Et H SO ₂ CH ₂ C1 3-57 Et H SEt 3-58 Et H SO ₂ Et 3-59 Et H _CF3 3-60 _CF3 H Cl 3-61 _CF3 H Br 3-62 _CF3 H SO ₂ Me 3-63 _CF3 H SO ₂ Et 3-64 _CF3 H _CF3 3-65 no ₂ hh ₂ F 3-66 no ₂ NHMe F 3-67 no ₂ NMe ₂ F 3-68 no ₂ Me Cl 3-69 no ₂ hh ₂ Cl 3-70 no ₂ NHMe Cl 3-71 no ₂ NMe ₂ Cl 3-72 no ₂ hh ₂ Br 3-73 no ₂ NHMe Br 3-74 no ₂ NMe ₂ Br 3-75 no ₂ hh _{2 CF3} 3-76 no ₂ NMe _{2 CF3} 3-77 no ₂ hh ₂ SO ₂ Me 3-78 no ₂ hh ₂ SO ₂ Et 3-79 no ₂ NHMe SO ₂ Me 3-80 no ₂ NMe ₂ SO ₂ Me 3-81 no ₂ NMe ₂ SO ₂ Et 3-82 no ₂ hh ₂ 1Н-1,2,4-triazol1-yl 3-83 no ₂ NHMe 1Н-1,2,4-triazol1-yl 3-84 no ₂ NMe ₂ 1Н-1,2,4-triazol1-yl 3-85 Me SMe H 3-86 Me SOM n 3-87 Me SO ₂ Me n 3-88 Me SEt n 3-89 Me SOEt n 3-90 Me SO ₂ Et n 3-91 Me S(CH ₂ ) ₂ OMe n 3-92 Me SO(CH ₂ ) ₂ OMe n 3-93 Me SO ₂ (CH ₂ ) ₂ OMe n

- 31 040923

3-94 Me F F 3-95 Me F Cl 3-96 Me SEt F 3-97 Me SOEt F 3-98 Me SO ₂ Et F 3-99 Me Me Cl 3-100 Me F Cl 3-101 Me Cl Cl 3-102 Me hh ₂ Cl 3-103 Me NHMe Cl 3-104 Me NMe ₂ Cl 3-105 Me O(CH ₂ ) ₂ OMe Cl 3-106 Me O(CH ₂ ) ₃ OMe Cl 3-107 Me O( _CH2 ) _4OMe Cl 3-108 Me OCH ₂ CONMe ₂ Cl 3-109 Me O(CH ₂ ) ₂ - C0NMe ₂ Cl 3-110 Me O(CH ₂ ) ₂ - NH(C0)NMe ₂ Cl 3-111 Me O(CH ₂ ) ₂ NH(C0)NHC0 ₂ Et Cl 3-112 Me O(CH ₂ ) ₂ NHCO ₂ Me Cl 3-113 Me OCH ₂ NHSO ₂ cPr Cl 3-114 Me O(CH ₂ )-5-2,4di-methyl-2,4dihydro-3H1,2,4-triazol3-one Cl 3-115 Me O (CH ₂ ) -3,5dimethyl-1,2oxazol-4-yl Cl 3-116 Me SMe Cl 3-117 Me SOM Cl 3-118 Me SO ₂ Me Cl 3-119 Me SEt Cl 3-120 Me SOEt Cl 3-121 Me SO ₂ Et Cl 3-122 Me S(CH ₂ ) ₂ OMe Cl 3-123 Me SO(CH ₂ ) ₂ OMe Cl 3-124 Me SO ₂ (CH ₂ ) ₂ OMe Cl 3-125 Me hh ₂ Br 3-126 Me NHMe Br 3-127 Me NMe ₂ Br 3-128 Me OCH ₂ CONMe ₂ Br

- 32 040923

3-129 Me O(CH ₂ )-5pyrrolidine-2OH Br 3-130 Me SMe Br 3-131 Me SOM Br 3-132 Me SO ₂ Me Br 3-133 Me SEt Br 3-134 Me SOEt Br 3-135 Me SO ₂ Et Br 3-136 Me SMe I 3-137 Me SOM I 3-138 Me SO ₂ Me I 3-139 Me SEt I 3-140 Me SOEt I 3-141 Me SO ₂ Et I 3-142 Me Cl _CF3 3-143 Me SMe _CF3 3-144 Me SOM _CF3 3-145 Me SO ₂ Me _CF3 3-146 Me SEt _CF3 3-147 Me SOEt _CF3 3-148 Me SO ₂ Et _CF3 3-149 Me S(CH ₂ ) ₂ OMe _CF3 3-150 Me SO(CH ₂ ) ₂ OMe _CF3 3-151 Me SO ₂ (CH ₂ ) ₂ OMe _CF3 3-152 Me Me SO ₂ Me 3-153 Me 4,5-dihydro- 1,2-oxazol-Zyl SO ₂ Me 3-154 Me 4,5-dihydro- 1,2-oxazole-3- silt SO ₂ Et 3-155 Me 5-cyanomethyl- 4,5-dihydro- 1,2-oxazole-3- silt SO ₂ Me 3-156 Me 5-cyanomethyl4,5-dihydro- 1,2-oxazole-3- silt SO ₂ Et 3-157 Me hh ₂ SO ₂ Me 3-158 Me NHMe SO ₂ Me 3-159 Me NMe ₂ SO ₂ Me 3-160 Me NH(CH ₂ ) ₂ OMe SO ₂ Me 3-161 Me pyrazol-1-yl SO ₂ Me 3-162 Me HE SO ₂ Me

-33 040923

3-163 Me ome SO ₂ Me 3-164 Me ome SO ₂ Et 3-165 Me OEt SO ₂ Me 3-166 Me OEt SO ₂ Et 3-167 Me Oipr SO ₂ Me 3-168 Me Oipr SO ₂ Et 3-169 Me O(CH ₂ ) ₂ OMe SO ₂ Me 3-170 Me O(CH ₂ ) ₂ OMe SO ₂ Et 3-171 Me O(CH ₂ ) ₃ OMe SO ₂ Me 3-172 Me O(CH ₂ ) ₃ OMe SO ₂ Et 3-173 Me O( _CH2 ) _4OMe SO ₂ Me 3-174 Me O( _CH2 ) _4OMe SO ₂ Et 3-175 Me O(CH ₂ ) ₂ NHSO2 Me SO ₂ Me 3-176 Me O(CH ₂ ) ₂ NHSO2 Me SO ₂ Et 3-177 Me OCH ₂ (CO)NMe ₂ SO ₂ Me 3-178 Me OCH ₂ (CO)NMe ₂ SO ₂ Et 3-179 Me [1,4]dioxan-2ylmethoxy SO ₂ Me 3-180 Me [1,4]dioxan-2ylmethoxy SO ₂ Et 3-181 Me O (CH ₂ ) ₂ -O- (3,5 dimethoxypyrimidin-2-yl) SO ₂ Me 3-182 Me C1 SO ₂ Me 3-183 Me SMe SO ₂ Me 3-184 Me SOM SO ₂ Me 3-185 Me SO ₂ Me SO ₂ Me 3-186 Me SO ₂ Me SO ₂ Et 3-187 Me SEt SO ₂ Me 3-188 Me SOEt SO ₂ Me 3-189 Me SO ₂ Et SO ₂ Me 3-190 Me S(CH ₂ ) ₂ OMe SO ₂ Me 3-191 Me SO(CH ₂ ) ₂ OMe SO ₂ Me 3-192 Me SO ₂ (CH ₂ ) ₂ OMe SO2Me 3-193 CH ₂ SMe ome SO ₂ Me 3-194 _CH2OMe ome SO ₂ Me 3-195 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OEt SO ₂ Me 3-196 CH ₂ O(CH ₂ ) ₂ OMe NH( _CH2 ) _3OEt SO ₂ Me 3-197 CH ₂ O (CH ₂ ) ₃ OMe ome SO ₂ Me 3-198 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OMe SO ₂ Me

- 34 040923

3-199 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) _3OMe SO ₂ Me 3-200 Et SMe Cl 3-201 Et SO ₂ Me Cl 3-202 Et SMe _CF3 3-203 Et SO ₂ Me _CF3 3-204 Et F SO ₂ Me 3-205 Et NH(CH ₂ ) ₂ OMe SO ₂ Me 3-206 IPr SO ₂ Me _CF3 3-207 cPr SO ₂ Me _CF3 3-208 _CF3 O(CH ₂ ) ₂ OMe F 3-209 _CF3 O(CH ₂ ) ₃ OMe F 3-210 _CF3 OCH ₂ CONMe ₂ F 3-211 _CF3 [1,4]dioxan-2ylmethoxy F 3-212 _CF3 O(CH ₂ ) ₂ OMe Cl 3-213 _CF3 O(CH ₂ ) ₃ OMe Cl 3-214 _CF3 OCH ₂ CONMe ₂ Cl 3-215 _CF3 [1,4]dioxan-2ylmethoxy Cl 3-216 _CF3 O (CH ₂ ) ₂ OMe Br 3-217 _CF3 O (CH ₂ ) ₃ OMe Br 3-218 _CF3 OCH ₂ CONMe ₂ Br 3-219 _CF3 [1,4]dioxan-2ylmethoxy Br 3-220 _CF3 O (CH ₂ ) ₂ OMe I 3-221 _CF3 O (CH ₂ ) ₃ OMe I 3-222 _CF3 OCH ₂ CONMe ₂ I 3-223 _CF3 [1,4]dioxan-2ylmethoxy I 3-224 _CF3 F SO ₂ Me 3-225 _CF3 F SO ₂ Et 3-226 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Me 3-227 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Et 3-228 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Me 3-229 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Et 3-230 _CF3 OCH ₂ CONMe ₂ SO ₂ Me 3-231 _CF3 OCH ₂ CONMe ₂ SO ₂ Et 3-232 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Me 3-233 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Et 3-234 F SMe _CF3 3-235 F SOM _CF3 3-236 Cl Me Cl 3-237 Cl DOS ₂ SNSN ₂ Cl

- 35 040923

3-238 Cl OCH ₂ CHF ₂ C1 3-239 Cl O(CH ₂ ) ₂ OMe C1 3-240 Cl OCH ₂ (CO)NMe ₂ C1 3-241 Cl O(CH ₂ )-5pyrrolidine-2OH C1 3-242 Cl SMe C1 3-243 Cl SOM C1 3-244 Cl SO ₂ Me C1 3-245 Cl F SMe 3-246 Cl Cl SO ₂ Me 3-247 Cl COOMe SO ₂ Me 3-248 Cl CONMe ₂ SO ₂ Me 3-249 Cl CONMe(OMe) SO ₂ Me 3-250 Cl _CH2OMe SO ₂ Me 3-251 Cl _CH2OMe SO ₂ Et 3-252 Cl _CH2OEt SO ₂ Me 3-253 Cl _CH2OEt SO ₂ Et 3-254 Cl CH ₂ OCH ₂ CHF ₂ SO ₂ Me 3-255 Cl ch ₂ och ₂ cf ₃ SO ₂ Me 3-256 Cl ch ₂ och ₂ cf ₃ SO ₂ Et 3-257 Cl ch ₂ och ₂ cf ₂ c hf ₂ SO ₂ Me 3-258 Cl CH ₂ O-s-pentyl SO ₂ Me 3-259 Cl _CH2PO (OMe) ₂ SO ₂ Me 3-260 Cl 4,5-dihydro- 1,2-oxazole-3- silt SMe 3-261 Cl 4,5-dihydro- 1,2-oxazole-3- silt SO ₂ Me 3-262 Cl 4,5-dihydro- 1,2-oxazole-3- silt SO ₂ Et 3-263 Cl 5-cyanomethyl4,5-dihydro- 1,2-oxazole-3- silt SO ₂ Me 3-264 Cl 5-cyanomethyl4,5-dihydro- 1,2-oxazole-3- silt SO ₂ Et 3-265 Cl 5-(methoxymethyl)-4,5dihydro-1,2oxazol-3-yl SO ₂ Et

-36040923

3-266 Cl 5-(methoxymethyl)-5-methyl4,5-dihydro1,2-oxazol-Zyl SO ₂ Et 3-267 Cl CH ₂ O- tetrahydrofuran-3-yl SO ₂ Me 3-268 Cl CH ₂ Otetrahydrofuran-3-yl SO ₂ Et 3-269 Cl CH ₂ OCH ₂ tetrahydrofuran-2-yl SO ₂ Me 3-270 Cl CH ₂ OCH ₂ tetrahydrofuran-2-yl SO ₂ Et 3-271 Cl CH ₂ OCH ₂ tetrahydrofuran-3-yl SO ₂ Me 3-272 Cl CH ₂ OCH ₂ tetrahydrofuran-3-yl SO ₂ Et 3-273 Cl OME SO ₂ Me 3-274 Cl OME SO ₂ Et 3-275 Cl OEt SO ₂ Me 3-276 Cl OEt SO ₂ Et 3-277 Cl Oipr SO ₂ Me 3-278 Cl Oipr SO ₂ Et 3-279 Cl O(CH ₂ ) ₂ OMe SO ₂ Me 3-280 Cl O( _CH2 ) _4OMe SO ₂ Me 3-281 Cl O (CH ₂ ) ₄ OMe SO ₂ Et 3-282 Cl O (CH ₂ ) ₃ OMe SO ₂ Me 3-283 Cl O (CH ₂ ) ₃ OMe SO ₂ Et 3-284 Cl O (CH ₂ ) ₂ OMe SO ₂ Me 3-285 Cl O (CH ₂ ) ₂ OMe SO ₂ Et 3-286 Cl [1,4]dioxan-2ylmethoxy SO ₂ Me 3-287 Cl [1,4]dioxan-2ylmethoxy SO ₂ Et 3-288 Cl OCH ₂ (CO)NMe ₂ SO ₂ Me 3-289 Cl OCH ₂ (CO)NMe ₂ SO ₂ Et 3-290 Cl SMe SO ₂ Me 3-291 Cl SOM SO ₂ Me 3-292 Br OME Br 3-293 Br O(CH ₂ ) ₂ OMe Br

- 37 040923

3-294 Br O(CH ₂ ) ₂ OMe SO ₂ Me 3-295 Br O(CH ₂ ) ₂ OMe SO ₂ Et 3-296 Br O(CH ₂ ) ₃ OMe SO ₂ Me 3-297 Br O(CH ₂ ) ₃ OMe SO ₂ Et 3-298 Br O( _CH2 ) _4OMe SO ₂ Me 3-299 Br O( _CH2 ) _4OMe SO ₂ Et 3-300 Br [1,4]dioxan-2ylmethoxy SO ₂ Me 3-301 Br [1,4]dioxan-2ylmethoxy SO ₂ Et 3-302 I O (CH ₂ ) ₂ OMe SO ₂ Me 3-303 I O (CH ₂ ) ₂ OMe SO ₂ Et 3-304 I O (CH ₂ ) ₃ OMe SO ₂ Me 3-305 I O (CH ₂ ) ₃ OMe SO ₂ Et 3-306 I O (CH ₂ ) ₄ OMe SO ₂ Me 3-307 I O (CH ₂ ) ₄ OMe SO ₂ Et 3-308 I [1,4]dioxan-2ylmethoxy SO ₂ Me 3-309 I [1,4]dioxan-2ylmethoxy SO ₂ Et 3-310 ome SMe _CF3 3-311 ome SOM _CF3 3-312 ome SO ₂ Me _CF3 3-313 ome SOEt _CF3 3-314 ome SO ₂ Et _CF3 3-315 ome S(CH ₂ ) ₂ OMe _CF3 3-316 ome SO(CH ₂ ) ₂ OMe _CF3 3-317 ome SO ₂ (CH ₂ ) ₂ OMe _CF3 3-318 ome SMe Cl 3-319 ome SOM Cl 3-320 ome SO ₂ Me Cl 3-321 ome SEt Cl 3-322 ome SOEt Cl 3-323 ome S02Et Cl 3-324 ome S(CH ₂ ) ₂ OMe Cl 3-325 ome SO(CH ₂ ) ₂ OMe Cl 3-326 ome SO ₂ (CH ₂ ) ₂ OMe Cl 3-327 OCH ₂ c-Pr SMe _CF3 3-328 OCH ₂ c-Pr SOM _CF3 3-329 OCH ₂ c-Pr SO ₂ Me _CF3 3-330 OCH ₂ c-Pr SEt _CF3 3-331 OCH ₂ c-Pr SOEt _CF3 3-332 OCH ₂ c-Pr SO ₂ Et _CF3 3-333 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe _CF3 3-334 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe _CF3 3-335 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe _CF3 3-336 OCH ₂ c-Pr SMe Cl 3-337 OCH ₂ c-Pr SOM Cl 3-338 OCH ₂ c-Pr SO ₂ Me Cl 3-339 OCH ₂ c-Pr SEt Cl 3-340 OCH ₂ c-Pr SOEt Cl 3-341 OCH ₂ c-Pr SO ₂ Et Cl 3-342 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe Cl 3-343 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe Cl 3-344 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe Cl 3-345 OCH ₂ c-Pr SMe SO ₂ Me 3-346 OCH ₂ c-Pr SOM SO ₂ Me 3-347 OCH ₂ c-Pr SO ₂ Me SO ₂ Me 3-348 OCH ₂ c-Pr SEt SO ₂ Me 3-349 OCH ₂ c-Pr SOEt SO ₂ Me 3-350 OCH ₂ c-Pr SO ₂ Et SO ₂ Me 3-351 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe SO ₂ Me 3-352 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe SO ₂ Me 3-353 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe SO ₂ Me 3-354 SO ₂ Me F _CF3 3-355 SO ₂ Me hh _{2 CF3} 3-356 SO ₂ Me NHEt Cl 3-357 SMe SEt F 3-358 SMe SMe F 3-359 Cl SMe _CF3 3-360 Cl S(O)Me _CF3 3-361 Cl SO ₂ Me _CF3 3-362 Cl SO ₂ Me SO ₂ Me

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Table 4

Compounds of general formula (I) wherein A is CY, V is hydrogen, W is fluorine and R is trifluoromethyl

No. X Y z Physical data CH-nmr, DMSOd ₆ , 400 MHz) 4-1 F H Cl 4-2 F H SO ₂ Me 4-3 F H SO ₂ Et 4-4 F H _CF3 4-5 F H no ₂ 4-6 C1 H Br 4-7 C1 H SMe 4-8 C1 H SOM 4-9 C1 H SO ₂ Me 4-10 C1 H SO ₂ CH ₂ C1 4-11 C1 H SEt 4-12 C1 H SO ₂ Et 4-13 C1 H _CF3 4-14 C1 H no ₂ 4-15 C1 H pyrazol-1-yl 4-16 C1 H 1H-1,2,4triazol-1-yl 4-17 Vg H Cl 4-18 Vg H Br 4-19 Vg H SO ₂ Me 4-20 Vg H SO ₂ Et 4-21 Vg H _CF3 4-22 SO ₂ Me H Cl 4-23 SO ₂ Me H Br 4-24 SO ₂ Me H SMe 4-25 SO ₂ Me H SOM 4-26 SO ₂ Me H SO ₂ Me 4-27 SO ₂ Me H SO ₂ Et 4-28 SO ₂ Me H _CF3 4-29 SO ₂ Et H Cl 4-30 SO ₂ Et H Br 4-31 SO ₂ Et H SMe 4-32 SO ₂ Et H SOM 4-33 SO ₂ Et H SO ₂ Me 4-34 SO ₂ Et H _CF3 4-35 no ₂ H F 4-36 no ₂ H Cl 4-37 no ₂ H Br 4-38 no ₂ H I 4-39 no ₂ H CN 4-40 no ₂ H SO ₂ Me 4-41 no ₂ H SO ₂ Et 4-42 no ₂ H _CF3 4-43 Me H Cl 4-44 Me H Br

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4-45 Me H SMe 4-46 Me H SO ₂ Me 4-47 Me H SO ₂ CH ₂ C1 4-48 Me H SEt 4-49 Me H SO ₂ Et 4-50 Me H _CF3 4-51 CH ₂ SO ₂ Me H _CF3 4-52 Et H Cl 4-53 Et H Br 4-54 Et H SMe 4-55 Et H SO ₂ Me 4-56 Et H SO ₂ CH ₂ C1 4-57 Et H SEt 4-58 Et H SO ₂ Et 4-59 Et H _CF3 4-60 _CF3 H Cl 4-61 _CF3 H Br 4-62 _CF3 H SO ₂ Me 4-63 _CF3 H SO ₂ Et 4-64 _CF3 H _CF3 4-65 no ₂ hh ₂ F 4-66 no ₂ NHMe F 4-67 no ₂ NMe ₂ F 4-68 no ₂ Me Cl 4-69 no ₂ hh ₂ Cl 4-70 no ₂ NHMe Cl 4-71 no ₂ NMe ₂ Cl 4-72 no ₂ hh ₂ Br 4-73 no ₂ NHMe Br 4-74 no ₂ NMe ₂ Br 4-75 no ₂ hh _{2 CF3} 4-76 no ₂ NMe _{2 CF3} 4-77 no ₂ hh ₂ SO ₂ Me 4-78 no ₂ hh ₂ SO ₂ Et 4-79 no ₂ NHMe SO ₂ Me 4-80 no ₂ NMe ₂ SO ₂ Me 4-81 no ₂ NMe ₂ SO ₂ Et 4-82 no ₂ hh ₂ 1H-1,2,4triazol-1-yl 4-83 no ₂ NHMe 1H-1,2,4triazol-1-yl 4-84 no ₂ NMe ₂ SH-1,2,4triazol-1-yl 4-85 Me SMe Η 4-86 Me SOM Η

- 40 040923

4-87 Me SO ₂ Me H 4-88 Me SEt H 4-89 Me SOEt H 4-90 Me SO ₂ Et H 4-91 Me S(CH ₂ ) ₂ OMe H 4-92 Me SO(CH ₂ ) ₂ OMe H 4-93 Me SO ₂ (CH ₂ ) ₂ OMe H 4-94 Me F F 4-95 Me F Cl 4-96 Me SEt F 4-97 Me SOEt F 4-98 Me SO ₂ Et F 4-99 Me Me Cl 4-100 Me F Cl 4-101 Me Cl Cl 4-102 Me hh ₂ Cl 4-103 Me NHMe Cl 4-104 Me NMe ₂ Cl 4-105 Me O(CH ₂ ) ₂ OMe Cl 4-106 Me O(CH ₂ ) ₃ OMe Cl 4-107 Me O( _CH2 ) _4OMe Cl 4-108 Me OCH ₂ CONMe ₂ Cl 4-109 Me O(CH ₂ ) ₂ -CO-NMe ₂ Cl 4-110 Me O(CH ₂ ) ₂ - NH(C0)NMe ₂ Cl 4-111 Me O(CH ₂ ) ₂ - NH(CO)NHCO ₂ Et Cl 4-112 Me O(CH ₂ ) ₂ -NHCO ₂ Me Cl 4-113 Me OCH ₂ -NHSO ₂ cPr Cl 4-114 Me O(CH ₂ )-5-2,4dimethyl-2,4dihydro-3H-1,2,4triazol-3-one Cl 4-115 Me O(CH ₂ )-3,5dimethyl-1,2oxazol-4-yl Cl 4-116 Me SMe Cl 4-117 Me SOM Cl 4-118 Me SO ₂ Me Cl 4-119 Me SEt Cl 4-120 Me SOEt Cl 4-121 Me SO ₂ Et Cl 4-122 Me S(CH ₂ ) ₂ OMe Cl 4-123 Me SO(CH ₂ ) ₂ OMe Cl 4-124 Me SO ₂ (CH ₂ ) ₂ OMe Cl

- 41 040923

4-125 Me hh ₂ Br 4-126 Me NHMe Br 4-127 Me NMe ₂ Br 4-128 Me OCH ₂ (CO)NMe ₂ Br 4-129 Me O(CH ₂ )-5pyrrolidin-2-one Br 4-130 Me SMe Br 4-131 Me SOM Br 4-132 Me SO ₂ Me Br 4-133 Me SEt Br 4-134 Me SOEt Br 4-135 Me SO ₂ Et Br 4-136 Me SMe I 4-137 Me SOM I 4-138 Me SO ₂ Me I 4-139 Me SEt I 4-140 Me SOEt I 4-141 Me SO ₂ Et I 4-142 Me Cl _CF3 4-143 Me SMe _CF3 4-144 Me SOM _CF3 4-145 Me SO ₂ Me _CF3 4-146 Me SEt _CF3 4-147 Me SOEt _CF3 4-148 Me SO ₂ Et _CF3 4-149 Me S(CH ₂ ) ₂ OMe _CF3 4-150 Me SO(CH ₂ ) ₂ OMe _CF3 4-151 Me SO ₂ (CH ₂ ) ₂ OMe _CF3 4-152 Me Me SO ₂ Me 4-153 Me 4,5-dihydro-1,2oxazol-3-yl SO ₂ Me 4-154 Me 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 4-155 Me 5-cyanomethyl-4,5dihydro-1,2oxazol-3-yl SO ₂ Me 4-156 Me 5-cyanomethyl-4,5dihydro-1,2oxazol-3-yl SO ₂ Et 4-157 Me hh ₂ SO ₂ Me 4-158 Me NHMe SO ₂ Me 4-159 Me NMe ₂ SO ₂ Me 4-160 Me NH(CH ₂ ) ₂ OMe SO ₂ Me 4-161 Me pyrazol-1-yl SO ₂ Me 4-162 Me HE SO ₂ Me

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4-163 Me ome SO ₂ Me 4-164 Me ome SO ₂ Et 4-165 Me OEt SO ₂ Me 4-166 Me OEt SO ₂ Et 4-167 Me Oipr SO ₂ Me 4-168 Me Oipr SO ₂ Et 4-169 Me O(CH ₂ ) ₂ OMe SO ₂ Me 4-170 Me O(CH ₂ ) ₂ OMe SO ₂ Et 4-171 Me O(CH ₂ ) ₃ OMe SO ₂ Me 4-172 Me O(CH ₂ ) ₃ OMe SO ₂ Et 4-173 Me O( _CH2 ) _4OMe SO ₂ Me 4-174 Me O( _CH2 ) _4OMe SO ₂ Et 4-175 Me O(CH ₂ ) ₂ NHSO2Me SO ₂ Me 4-176 Me O(CH ₂ ) ₂ NHSO2Me SO ₂ Et 4-177 Me OCH ₂ (CO)NMe ₂ SO ₂ Me 4-178 Me OCH ₂ (CO)NMe ₂ SO ₂ Et 4-179 Me [1,4]dioxan-2ylmethoxy SO ₂ Me 4-180 Me [1,4]dioxan-2ylmethoxy SO ₂ Et 4-181 Me O (CH ₂ ) ₂ -O- (3,5-dimethoxypyrimidin -2-yl) SO ₂ Me 4-182 Me C1 SO ₂ Me 4-183 Me SMe SO ₂ Me 4-184 Me SOM SO ₂ Me 4-185 Me SO ₂ Me SO ₂ Me 4-186 Me SO ₂ Me SO ₂ Et 4-187 Me SEt SO ₂ Me 4-188 Me SOEt SO ₂ Me 4-189 Me SO ₂ Et SO ₂ Me 4-190 Me S(CH ₂ ) ₂ OMe SO ₂ Me 4-191 Me SO(CH ₂ ) ₂ OMe SO ₂ Me 4-192 Me SO ₂ (CH ₂ ) ₂ OMe SO2Me 4-193 CH ₂ SMe ome SO ₂ Me 4-194 _CH2OMe ome SO ₂ Me 4-195 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OEt SO ₂ Me 4-196 CH ₂ O(CH ₂ ) ₂ OMe NH( _CH2 ) _3OEt SO ₂ Me 4-197 CH ₂ O (CH ₂ ) ₃ OMe ome SO ₂ Me 4-198 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OMe SO ₂ Me

- 43 040923

4-199 CH ₂ O (CH ₂ ) ₂ OMe NH(CH ₂ ) _3OMe SO ₂ Me 4-200 Et SMe Cl 4-201 Et SO ₂ Me Cl 4-202 Et SMe _CF3 4-203 Et SO ₂ Me _CF3 4-204 Et F SO ₂ Me 4-205 Et NH(CH ₂ ) ₂ OMe SO ₂ Me 4-206 IPr SO ₂ Me _CF3 4-207 cPr SO ₂ Me _CF3 4-208 _CF3 O(CH ₂ ) ₂ OMe F 4-209 _CF3 O(CH ₂ ) ₃ OMe F 4-210 _CF3 OCH ₂ CONMe ₂ F 4-211 _CF3 [1,4]dioxan-2ylmethoxy F 4-212 _CF3 O(CH ₂ ) ₂ OMe Cl 4-213 _CF3 O(CH ₂ ) ₃ OMe Cl 4-214 _CF3 OCH ₂ CONMe ₂ Cl 4-215 _CF3 [1,4]dioxan-2ylmethoxy Cl 4-216 _CF3 O (CH ₂ ) ₂ OMe Br 4-217 _CF3 O (CH ₂ ) ₃ OMe Br 4-218 _CF3 OCH ₂ CONMe ₂ Br 4-219 _CF3 [1,4]dioxan-2ylmethoxy Br 4-220 _CF3 O (CH ₂ ) ₂ OMe I 4-221 _CF3 O (CH ₂ ) ₃ OMe I 4-222 _CF3 OCH ₂ CONMe ₂ I 4-223 _CF3 [1,4]dioxan-2ylmethoxy I 4-224 _CF3 F SO ₂ Me 4-225 _CF3 F SO ₂ Et 4-226 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Me 4-227 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Et 4-228 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Me 4-229 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Et 4-230 _CF3 OCH ₂ CONMe ₂ SO ₂ Me 4-231 _CF3 OCH ₂ CONMe ₂ SO ₂ Et 4-232 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Me 4-233 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Et 4-234 F SMe _CF3 4-235 F SOM _CF3 4-236 Cl Me Cl

- 44 040923

4-237 Cl OCH2CHCH2 C1 4-238 Cl OCH2CHF2 C1 4-239 Cl O(CH ₂ ) ₂ OMe C1 4-240 Cl OCH ₂ CONMe ₂ C1 4-241 Cl O(CH ₂ )-5pyrrolidin-2-one C1 4-242 Cl SMe C1 4-243 Cl SOM C1 4-244 Cl SO ₂ Me C1 4-245 Cl F SMe 4-246 Cl Cl SO ₂ Me 4-247 Cl COOMe SO ₂ Me 4-248 Cl CONMe ₂ SO ₂ Me 4-249 Cl CONMe(OMe) SO ₂ Me 4-250 Cl _CH2OMe SO ₂ Me 4-251 Cl _CH2OMe SO ₂ Et 4-252 Cl _CH2OEt SO ₂ Me 4-253 Cl _CH2OEt SO ₂ Et 4-254 Cl CH2OCH2CHF2 SO ₂ Me 4-255 Cl CH2OCH2CF3 SO ₂ Me 4-256 Cl CH2OCH2CF3 SMe 4-257 Cl CH2OCH2CF3 SO ₂ Et 4-258 Cl CH2OCH2CF2CHF2 SO ₂ Me 4-259 Cl CH ₂ O-s-pentyl SO ₂ Me 4-260 Cl _CH2PO (OMe) ₂ SO ₂ Me 4-261 Cl 4,5-dihydro-1,2oxazol-3-yl SMe 4-262 Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Me 4-263 Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 4-264 Cl 5-cyanomethyl- 4,5dihydro-1,2oxazol-3-yl SO ₂ Me 4-265 Cl 5-cyanomethyl- 4,5dihydro-1,2oxazol-3-yl SO ₂ Et 4-266 Cl 5-(methoxymethyl)4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 4-267 Cl 5-(methoxymethyl)5-methyl-4,5dihydro-1,2oxazol-3-yl SO ₂ Et

- 45 040923

4-268 Cl CH ₂ Tetrahydrofuran3-yl SO ₂ Me 4-269 Cl CH ₂ Tetrahydrofuran3-yl SO ₂ Et 4-270 Cl CH ₂ OCH ₂ tetrahydrofuran2-yl SO ₂ Me 4-271 Cl CH ₂ OCH ₂ tetrahydrofuran2-yl SO ₂ Et 4-272 Cl CH ₂ OCH ₂ tetrahydrofuran3-yl SO ₂ Me 4-273 Cl CH ₂ OCH ₂ tetrahydrofuran3-yl SO ₂ Et 4-274 Cl OME SO ₂ Me 4-275 Cl OME SO ₂ Et 4-276 Cl OEt SO ₂ Me 4-277 Cl OEt SO ₂ Et 4-278 Cl Oipr SO ₂ Me 4-279 Cl Oipr SO ₂ Et 4-280 Cl O(CH ₂ ) ₂ OMe SO ₂ Me 4-281 Cl O( _CH2 ) _4OMe SO ₂ Me 4-282 Cl O (CH ₂ ) ₄ OMe SO ₂ Et 4-283 Cl O (CH ₂ ) ₃ OMe SO ₂ Me 4-284 Cl O (CH ₂ ) ₃ OMe SO ₂ Et 4-285 Cl O (CH ₂ ) ₂ OMe SO ₂ Me 4-286 Cl O (CH ₂ ) ₂ OMe SO ₂ Et 4-287 Cl [1,4]dioxane-2- ylmethoxy SO ₂ Me 4-288 Cl [1,4]dioxan-2ylmethoxy SO ₂ Et 4-289 Cl OCH ₂ (CO)NMe ₂ SO ₂ Me 4-290 Cl OCH ₂ (CO)NMe ₂ SO ₂ Et 4-291 Cl SMe SO ₂ Me 4-292 Cl SOM SO ₂ Me 4-293 Br OME Br 4-294 Br O(CH ₂ ) ₂ OMe Br 4-295 Br O (CH ₂ ) ₂ OMe SO ₂ Me 4-296 Br O (CH ₂ ) ₂ OMe SO ₂ Et 4-297 Br O (CH ₂ ) ₃ OMe SO ₂ Me 4-298 Br O (CH ₂ ) ₃ OMe SO ₂ Et

- 46 040923

4-299 Br O( _CH2 ) _4OMe SO ₂ Me 4-300 Br O( _CH2 ) _4OMe SO ₂ Et 4-301 Br [1,4]dioxan-2ylmethoxy SO ₂ Me 4-302 Br [1,4]dioxan-2ylmethoxy SO ₂ Et 4-303 I O (CH ₂ ) ₂ OMe SO ₂ Me 4-304 I O (CH ₂ ) ₂ OMe SO ₂ Et 4-305 I O (CH ₂ ) ₃ OMe SO ₂ Me 4-306 I O (CH ₂ ) ₃ OMe SO ₂ Et 4-307 I O (CH ₂ ) ₄ OMe SO ₂ Me 4-308 I O (CH ₂ ) ₄ OMe SO ₂ Et 4-309 I [1,4]dioxan-2ylmethoxy SO ₂ Me 4-310 I [1,4]dioxan-2ylmethoxy SO ₂ Et 4-311 ome SMe _CF3 4-312 ome SOM _CF3 4-313 ome SO ₂ Me _CF3 4-314 ome SOEt _CF3 4-315 ome SO ₂ Et _CF3 4-316 ome S(CH ₂ ) ₂ OMe _CF3 4-317 ome SO(CH ₂ ) ₂ OMe _CF3 4-318 ome SO ₂ (CH ₂ ) ₂ OMe _CF3 4-319 ome SMe Cl 4-320 ome SOM Cl 4-321 ome SO ₂ Me Cl 4-322 ome SEt Cl 4-323 ome SOEt Cl 4-324 ome S02Et Cl 4-325 ome S(CH ₂ ) ₂ OMe Cl 4-326 ome SO(CH ₂ ) ₂ OMe Cl 4-327 ome SO ₂ (CH ₂ ) ₂ OMe Cl 4-328 OCH ₂ c-Pr SMe _CF3 4-329 OCH ₂ c-Pr SOM _CF3 4-330 OCH ₂ c-Pr SO ₂ Me _CF3 4-331 OCH ₂ c-Pr SEt _CF3 4-332 OCH ₂ c-Pr SOEt _CF3 4-333 OCH ₂ c-Pr SO ₂ Et _CF3 4-334 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe _CF3 4-335 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe _CF3 4-336 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe _CF3 4-337 OCH ₂ c-Pr SMe Cl 4-338 OCH ₂ c-Pr SOM Cl 4-339 OCH ₂ c-Pr SO ₂ Me Cl 4-340 OCH ₂ c-Pr SEt Cl 4-341 OCH ₂ c-Pr SOEt Cl 4-342 OCH ₂ c-Pr SO ₂ Et Cl 4-343 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe Cl 4-344 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe Cl 4-345 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe Cl 4-346 OCH ₂ c-Pr SMe SO ₂ Me 4-347 OCH ₂ c-Pr SOM SO ₂ Me 4-348 OCH ₂ c-Pr SO ₂ Me SO ₂ Me 4-349 OCH ₂ c-Pr SEt SO ₂ Me 4-350 OCH ₂ c-Pr SOEt SO ₂ Me 4-351 OCH ₂ c-Pr SO ₂ Et SO ₂ Me 4-352 OCH ₂ c-Pr S(CH ₂ ) ₂ OMe SO ₂ Me 4-353 OCH ₂ c-Pr SO(CH ₂ ) ₂ OMe SO ₂ Me 4-354 OCH ₂ c-Pr SO ₂ (CH ₂ ) ₂ OMe SO ₂ Me 4-355 SO ₂ Me F _CF3 4-356 SO ₂ Me hh _{2 CF3} 4-357 SO ₂ Me NHEt Cl 4-358 SMe SEt F 4-359 SMe SMe F 4-360 Cl SMe _CF3 4-361 Cl S(O)Me _CF3 4-362 Cl SO ₂ Me _CF3 4-363 Cl SO ₂ Me SO ₂ Me

- 47 040923

Table 5

Compounds of general formula (I) in which A is CY,

V is hydrogen, W is fluorine and R is CH ₂ OMe _L x n

n

5-1 F H Cl 5-2 F H SO ₂ Me 5-3 F H SO ₂ Et 5-4 F H _CF3 5-5 F H no ₂ 5-6 C1 H Br 5-7 C1 H SMe 5-8 C1 H SOM 5-9 C1 H SO ₂ Me 5-10 C1 H SO ₂ CH ₂ C1 5-11 C1 H SEt 5-12 C1 H SO ₂ Et 5-13 C1 H _CF3 5-14 C1 H no ₂ 5-15 C1 H pyrazol-1-yl 5-16 C1 H 1H-1,2,4-triazole-1- IL 5-17 Vg H Cl 5-18 Vg H Br 5-19 Vg H SO ₂ Me 5-20 Vg H SO ₂ Et 5-21 Vg H _CF3 5-22 SO ₂ Me H Cl 5-23 SO ₂ Me H Br 5-24 SO ₂ Me H SMe 5-25 SO ₂ Me H SOM 5-26 SO ₂ Me H SO ₂ Me 5-27 SO ₂ Me H SO ₂ Et 5-28 SO ₂ Me H _CF3 5-29 SO ₂ Et H Cl 5-30 SO ₂ Et H Br 5-31 SO ₂ Et H SMe 5-32 SO ₂ Et H SOM 5-33 SO ₂ Et H SO ₂ Me 5-34 SO ₂ Et H _CF3 5-35 no ₂ H F 5-36 no ₂ H Cl 5-37 no ₂ H Br 5-38 no ₂ H I 5-39 no ₂ H CN 5-40 no ₂ H SO ₂ Me 5-41 no ₂ H SO ₂ Et 5-42 no ₂ H _CF3 5-43 Me H Cl

- 48 040923

5-44 Me H Br 5-45 Me H SMe 5-46 Me H SO ₂ Me 5-47 Me H SO ₂ CH ₂ C1 5-48 Me H SEt 5-49 Me H SO ₂ Et 5-50 Me H _CF3 5-51 CH ₂ SO ₂ Me H _CF3 5-52 Et H Cl 5-53 Et H Br 5-54 Et H SMe 5-55 Et H SO ₂ Me 5-56 Et H SO ₂ CH ₂ C1 5-57 Et H SEt 5-58 Et H SO ₂ Et 5-59 Et H _CF3 5-60 _CF3 H Cl 5-61 _CF3 H Br 5-62 _CF3 H SO ₂ Me 5-63 _CF3 H SO ₂ Et 5-64 _CF3 H _CF3 5-65 no ₂ hh ₂ F 5-66 no ₂ NHMe F 5-67 no ₂ NMe ₂ F 5-68 no ₂ Me Cl 5-69 no ₂ hh ₂ Cl 5-70 no ₂ NHMe Cl 5-71 no ₂ NMe ₂ Cl 5-72 no ₂ hh ₂ Br 5-73 no ₂ NHMe Br 5-74 no ₂ NMe ₂ Br 5-75 no ₂ hh _{2 CF3} 5-76 no ₂ NMe _{2 CF3} 5-77 no ₂ hh ₂ SO ₂ Me 5-78 no ₂ hh ₂ SO ₂ Et 5-79 no ₂ NHMe SO ₂ Me 5-80 no ₂ NMe ₂ SO ₂ Me 5-81 no ₂ NMe ₂ SO ₂ Et 5-82 no ₂ hh ₂ 1Н-1,2,4-triazole-1- IL 5-83 no ₂ NHMe 1H-1,2,4-triazole-1- IL 5-84 no ₂ NMe ₂ 1H-1,2,4-triazole-1- IL

- 49 040923

5-85 Me SMe H 5-86 Me SOM H 5-87 Me SO ₂ Me H 5-88 Me SEt H 5-89 Me SOEt H 5-90 Me SO ₂ Et H 5-91 Me S(CH ₂ ) ₂ OMe H 5-92 Me SO(CH ₂ ) ₂ OMe H 5-93 Me SO ₂ (CH ₂ ) ₂ OMe H 5-94 Me F F 5-95 Me F Cl 5-96 Me SEt F 5-97 Me SOEt F 5-98 Me SO ₂ Et F 5-99 Me Me Cl 5-100 Me F Cl 5-101 Me Cl Cl 5-102 Me hh ₂ Cl 5-103 Me NHMe Cl 5-104 Me NMe ₂ Cl 5-105 Me O(CH ₂ ) ₂ OMe Cl 5-106 Me O(CH ₂ ) ₃ OMe Cl 5-107 Me O( _CH2 ) _4OMe Cl 5-108 Me OCH ₂ CONMe ₂ Cl 5-109 Me O(CH ₂ ) ₂ -CO-NMe ₂ Cl 5-110 Me O(CH ₂ ) ₂ NH(C0)NMe ₂ Cl 5-111 Me O(CH ₂ ) ₂ - NH(CO)NHCO ₂ Et Cl 5-112 Me O(CH ₂ ) ₂ -NHCO ₂ Me Cl 5-113 Me OCH ₂ -NHSO ₂ cPr Cl 5-114 Me O(CH ₂ )-5-2,4dimethyl-2,4dihydro-3H-1,2,4triazol-3-one Cl 5-115 Me O(CH ₂ )-3,5dimethyl-1,2oxazol-4-yl Cl 5-116 Me SMe Cl 5-117 Me SOM Cl 5-118 Me SO ₂ Me Cl 5-119 Me SEt Cl 5-120 Me SOEt Cl 5-121 Me SO ₂ Et Cl

- 50 040923

5-122 Me S(CH ₂ ) ₂ OMe Cl 5-123 Me SO(CH ₂ ) ₂ OMe Cl 5-124 Me SO ₂ (CH ₂ ) ₂ OMe Cl 5-125 Me hh ₂ Br 5-126 Me NHMe Br 5-127 Me NMe ₂ Br 5-128 Me OCH ₂ (CO)NMe ₂ Br 5-129 Me O(CH ₂ )-5pyrrolidin-2-one Br 5-130 Me SMe Br 5-131 Me SOM Br 5-132 Me SO ₂ Me Br 5-133 Me SEt Br 5-134 Me SOEt Br 5-135 Me SO ₂ Et Br 5-136 Me SMe I 5-137 Me SOM I 5-138 Me SO ₂ Me I 5-139 Me SEt I 5-140 Me SOEt I 5-141 Me SO ₂ Et I 5-142 Me Cl _CF3 5-143 Me SMe _CF3 5-144 Me SOM _CF3 5-145 Me SO ₂ Me _CF3 5-146 Me SEt _CF3 5-147 Me SOEt _CF3 5-148 Me SO ₂ Et _CF3 5-149 Me S(CH ₂ ) ₂ OMe _CF3 5-150 Me SO(CH ₂ ) ₂ OMe _CF3 5-151 Me SO ₂ (CH ₂ ) ₂ OMe _CF3 5-152 Me Me SO ₂ Me 5-153 Me 4,5-dihydro-1,2oxazol-3-yl SO ₂ Me 5-154 Me 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et 5-155 Me 5-cyanomethyl-4,5dihydro-1,2oxazol-3-yl SO ₂ Me 5-156 Me 5-cyanomethyl-4,5dihydro-1,2oxazol-3-yl SO ₂ Et 5-157 Me hh ₂ SO ₂ Me 5-158 Me NHMe SO ₂ Me

- 51 040923

5-159 Me NMe ₂ SO ₂ Me 5-160 Me NH(CH ₂ ) ₂ OMe SO ₂ Me 5-161 Me pyrazol-1-yl SO ₂ Me 5-162 Me Oh SO ₂ Me 5-163 Me ome SO ₂ Me 5-164 Me ome SO ₂ Et 5-165 Me OEt SO ₂ Me 5-166 Me OEt SO ₂ Et 5-167 Me Oipr SO ₂ Me 5-168 Me Oipr SO ₂ Et 5-169 Me O(CH ₂ ) ₂ OMe SO ₂ Me 5-170 Me O(CH ₂ ) ₂ OMe SO ₂ Et 5-171 Me O(CH ₂ ) ₃ OMe SO ₂ Me 5-172 Me O(CH ₂ ) ₃ OMe SO ₂ Et 5-173 Me O( _CH2 ) _4OMe SO ₂ Me 5-174 Me O( _CH2 ) _4OMe SO ₂ Et 5-175 Me O(CH ₂ ) ₂ NHSO2Me SO ₂ Me 5-176 Me O(CH ₂ ) ₂ NHSO2Me SO ₂ Et 5-177 Me OCH ₂ (CO)NMe ₂ SO ₂ Me 5-178 Me OCH ₂ (CO)NMe ₂ SO ₂ Et 5-179 Me [1,4]dioxan-2ylmethoxy SO ₂ Me 5-180 Me [1,4]dioxan-2ylmethoxy SO ₂ Et 5-181 Me O (CH ₂ ) ₂ -O- (3,5-dimethoxypyrimidin-2-yl) SO ₂ Me 5-182 Me C1 SO ₂ Me 5-183 Me SMe SO ₂ Me 5-184 Me SOM SO ₂ Me 5-185 Me SO ₂ Me SO ₂ Me 5-186 Me SO ₂ Me SO ₂ Et 5-187 Me SEt SO ₂ Me 5-188 Me SOEt SO ₂ Me 5-189 Me SO ₂ Et SO ₂ Me 5-190 Me S(CH ₂ ) ₂ OMe SO ₂ Me 5-191 Me SO(CH ₂ ) ₂ OMe SO ₂ Me 5-192 Me SO ₂ (CH ₂ ) ₂ OMe SO2Me 5-193 CH ₂ SMe ome SO ₂ Me 5-194 _CH2OMe ome SO ₂ Me 5-195 CH ₂ O(CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OEt SO ₂ Me 5-196 CH ₂ O(CH ₂ ) ₂ OMe NH( _CH2 ) _3OEt SO ₂ Me

- 52 040923

5-197 CH ₂ O (CH ₂ ) ₃ OMe ome SO ₂ Me 5-198 CH ₂ O (CH ₂ ) ₂ OMe NH(CH ₂ ) ₂ OMe SO ₂ Me 5-199 CH ₂ O (CH ₂ ) ₂ OMe NH(CH ₂ ) _3OMe SO ₂ Me 5-200 Et SMe Cl 5-201 Et SO ₂ Me Cl 5-202 Et SMe _CF3 5-203 Et SO ₂ Me _CF3 5-204 Et F SO ₂ Me 5-205 Et NH(CH ₂ ) ₂ OMe SO ₂ Me 5-206 IPr SO ₂ Me _CF3 5-207 cPr SO ₂ Me _CF3 5-208 _CF3 O(CH ₂ ) ₂ OMe F 5-209 _CF3 O(CH ₂ ) ₃ OMe F 5-210 _CF3 OCH ₂ CONMe ₂ F 5-211 _CF3 [1,4]dioxan-2ylmethoxy F 5-212 _CF3 O(CH ₂ ) ₂ OMe Cl 5-213 _CF3 O(CH ₂ ) ₃ OMe Cl 5-214 _CF3 OCH ₂ CONMe ₂ Cl 5-215 _CF3 [1,4]dioxan-2ylmethoxy Cl 5-216 _CF3 O (CH ₂ ) ₂ OMe Br 5-217 _CF3 O (CH ₂ ) ₃ OMe Br 5-218 _CF3 OCH ₂ CONMe ₂ Br 5-219 _CF3 [1,4]dioxan-2ylmethoxy Br 5-220 _CF3 O (CH ₂ ) ₂ OMe I 5-221 _CF3 O (CH ₂ ) ₃ OMe I 5-222 _CF3 OCH ₂ CONMe ₂ I 5-223 _CF3 [1,4]dioxan-2ylmethoxy I 5-224 _CF3 F SO ₂ Me 5-225 _CF3 F SO ₂ Et 5-226 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Me 5-227 _CF3 O (CH ₂ ) ₂ OMe SO ₂ Et 5-228 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Me 5-229 _CF3 O (CH ₂ ) ₃ OMe SO ₂ Et 5-230 _CF3 OCH ₂ CONMe ₂ SO ₂ Me 5-231 _CF3 OCH ₂ CONMe ₂ SO ₂ Et 5-232 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Me

- 53 040923

5-233 _CF3 [1,4]dioxan-2ylmethoxy SO ₂ Et 5-234 F SMe _CF3 5-235 F SOM _CF3 5-236 Cl Me Cl 5-237 Cl OCH ₂ CHCH ₂ Cl 5-238 Cl OCH2CHF2 Cl 5-239 Cl O(CH ₂ ) ₂ OMe Cl 5-240 Cl OCH ₂ CONMe ₂ Cl 5-241 Cl O(CH ₂ )-5pyrrolidin-2-one Cl 5-242 Cl SMe Cl 5-243 Cl SOM Cl 5-244 Cl SO ₂ Me Cl 5-245 Cl F SMe 5-246 Cl Cl SO ₂ Me 5-247 Cl COOMe SO ₂ Me 5-248 Cl CONMe ₂ SO ₂ Me 5-249 Cl CONMe(OMe) SO ₂ Me 5-250 Cl _CH2OMe SO ₂ Me 5-251 Cl _CH2OMe SO ₂ Et 5-252 Cl _CH2OEt SO ₂ Me 5-253 Cl _CH2OEt SO ₂ Et 5-254 Cl CH2OCH2CHF2 SO ₂ Me 5-255 Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 5-256 Cl ch ₂ och ₂ cf ₃ SO ₂ Et 5-257 Cl CH2OCH2CF2CHF2 SO ₂ Me 5-258 Cl CHNO-s-pentyl SO ₂ Me 5-259 Cl _CH2PO (OMe) ₂ SO ₂ Me 5-260 Cl 4,5-dihydro-1,2oxazol-3-yl SMe 5-261 Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Me 5-262 Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 5-263 Cl 5-cyanomethyl- 4,5dihydro-1,2oxazol-3-yl SO ₂ Me 5-264 Cl 5-cyanomethyl- 4,5- dihydro-1,2- oxazol-3-yl SO ₂ Et 5-265 Cl 5-(methoxymethyl)- 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et

- 54 040923

5-266 Cl 5-(methoxymethyl)5-methyl-4,5dihydro-1,2oxazol-3-yl SO ₂ Et 5-267 Cl CH ₂ Otetrahydrofuran3-yl SO ₂ Me 5-268 Cl CH ₂ Otetrahydrofuran3-yl SO ₂ Et 5-269 Cl CH ₂ OCH ₂ tetrahydrofuran2-yl SO ₂ Me 5-270 Cl CH ₂ OCH ₂ tetrahydrofuran2-yl SO ₂ Et 5-271 Cl CH ₂ OCH ₂ tetrahydrofuran3-yl SO ₂ Me 5-272 Cl CH ₂ OCH ₂ tetrahydrofuran3-yl SO ₂ Et 5-273 Cl OME SO ₂ Me 5-274 Cl OME SO ₂ Et 5-275 Cl OEt SO ₂ Me 5-276 Cl OEt SO ₂ Et 5-277 Cl Oipr SO ₂ Me 5-278 Cl Oipr SO ₂ Et 5-279 Cl O(CH ₂ ) ₂ OMe SO ₂ Me 5-280 Cl O( _CH2 ) _4OMe SO ₂ Me 5-281 Cl O (CH ₂ ) ₄ OMe SO ₂ Et 5-282 Cl O (CH ₂ ) ₃ OMe SO ₂ Me 5-283 Cl O (CH ₂ ) ₃ OMe SO ₂ Et 5-284 Cl O (CH ₂ ) ₂ OMe SO ₂ Me 5-285 Cl O (CH ₂ ) ₂ OMe SO ₂ Et 5-286 Cl [1,4]dioxan-2ylmethoxy SO ₂ Me 5-287 Cl [1,4]dioxan-2ylmethoxy SO ₂ Et 5-288 Cl OCH ₂ (CO)NMe ₂ SO ₂ Me 5-289 Cl OCH ₂ (CO)NMe ₂ SO ₂ Et 5-290 Cl SMe SO ₂ Me 5-291 Cl SOM SO ₂ Me 5-292 Br ome Br

- 55 040923

5-293 Br O(CH ₂ ) ₂ OMe Br 5-294 Br O(CH ₂ ) ₂ OMe SO ₂ Me 5-295 Br O(CH ₂ ) ₂ OMe SO ₂ Et 5-296 Br O(CH ₂ ) ₃ OMe SO ₂ Me 5-297 Br O(CH ₂ ) ₃ OMe SO ₂ Et 5-298 Br O( _CH2 ) _4OMe SO ₂ Me 5-299 Br O( _CH2 ) _4OMe SO ₂ Et 5-300 Br [1,4]dioxan-2ylmethoxy SO ₂ Me 5-301 Br [1,4]dioxan-2ylmethoxy SO ₂ Et 5-302 I O (CH ₂ ) ₂ OMe SO ₂ Me 5-303 I O (CH ₂ ) ₂ OMe SO ₂ Et 5-304 I O (CH ₂ ) ₃ OMe SO ₂ Me 5-305 I O (CH ₂ ) ₃ OMe SO ₂ Et 5-306 I O (CH ₂ ) ₄ OMe SO ₂ Me 5-307 I O (CH ₂ ) ₄ OMe SO ₂ Et 5-308 I [1,4]dioxan-2ylmethoxy SO ₂ Me 5-309 I [1,4]dioxan-2ylmethoxy SO ₂ Et 5-310 ome SMe _CF3 5-311 ome SOM _CF3 5-312 ome SO ₂ Me _CF3 5-313 ome SOEt _CF3 5-314 ome SO ₂ Et _CF3 5-315 ome S(CH ₂ ) ₂ OMe _CF3 5-316 ome SO(CH ₂ ) ₂ OMe _CF3 5-317 ome SO ₂ (CH ₂ ) ₂ OMe _CF3 5-318 ome SMe Cl 5-319 ome SOM Cl 5-320 ome SO ₂ Me Cl 5-321 ome SEt Cl 5-322 ome SOEt Cl 5-323 ome S02Et Cl 5-324 ome S(CH ₂ ) ₂ OMe Cl 5-325 ome SO(CH ₂ ) ₂ OMe Cl 5-326 ome SO ₂ (CH ₂ ) ₂ OMe Cl 5-327 ome H SO ₂ Me 5-328 OCH ₂ -c-Pr SMe _CF3 5-329 OCH ₂ -c-Pr SOM _CF3 5-330 OCH ₂ -c-Pr SO ₂ Me _CF3 5-331 OCH ₂ -c-Pr SEt _CF3 5-332 OCH ₂ -c-Pr SOEt _CF3 5-333 OCH ₂ -c-Pr SO ₂ Et _CF3 5-334 OCH ₂ -c-Pr S(CH ₂ ) ₂ OMe _CF3 5-335 OCH ₂ -c-Pr SO(CH ₂ ) ₂ OMe _CF3 5-336 OCH ₂ -c-Pr SO ₂ (CH ₂ ) ₂ OMe _CF3 5-337 OCH ₂ -c-Pr SMe Cl 5-338 OCH ₂ -c-Pr SOM Cl 5-339 OCH ₂ -c-Pr SO ₂ Me Cl 5-340 OCH ₂ -c-Pr SEt Cl 5-341 OCH ₂ -c-Pr SOEt Cl 5-342 OCH ₂ -c-Pr SO ₂ Et Cl 5-343 OCH ₂ -c-Pr S(CH ₂ ) ₂ OMe Cl 5-344 OCH ₂ -c-Pr SO(CH ₂ ) ₂ OMe Cl 5-345 OCH ₂ -c-Pr SO ₂ (CH ₂ ) ₂ OMe Cl 5-346 OCH ₂ -c-Pr SMe SO ₂ Me 5-347 OCH ₂ -c-Pr SOM SO ₂ Me 5-348 OCH ₂ -c-Pr SO ₂ Me SO ₂ Me 5-349 OCH ₂ -c-Pr SEt SO ₂ Me 5-350 OCH ₂ -c-Pr SOEt SO ₂ Me 5-351 OCH ₂ -c-Pr SO ₂ Et SO ₂ Me 5-352 OCH ₂ -c-Pr S(CH ₂ ) ₂ OMe SO ₂ Me 5-353 OCH ₂ -c-Pr SO(CH ₂ ) ₂ OMe SO ₂ Me 5-354 OCH ₂ -c-Pr SO ₂ (CH ₂ ) ₂ OMe SO ₂ Me 5-355 SO ₂ Me F _CF3 5-356 SO ₂ Me hh _{2 CF3} 5-357 SO ₂ Me NHEt Cl 5-358 SMe SEt F 5-359 SMe SMe F 5-360 F SO ₂ Me _CF3 5-361 Cl SMe _CF3 5-362 Cl S(O)Me _CF3 5-363 Cl SO ₂ Me _CF3 5-364 Cl SO ₂ Me SO ₂ Me

-56040923

Table 6 Compounds of general formula (I) in which A is CY, V is hydrogen, W is fluorine

n

No. R X Y Z Physical Data 6-1 s-Pg no ₂ H SO ₂ Me 6-2 s-Pg Cl H SO ₂ Me 6-3 s-Pg SO ₂ Me H _CF3 6-4 s-Pg no ₂ H ome 6-5 s-Pg no ₂ H Br 6-6 s-Pg no ₂ H Cl 6-7 s-Pg no ₂ H _CF3 6-8 s-Pg no ₂ H no ₂ 6-9 s-Pg no ₂ H Me 6-10 s-Pg no ₂ H F 6-11 s-Pg ome H SO ₂ Me 6-12 s-Pg _CF3 H no ₂ 6-13 s-Pg _CF3 H Cl 6-14 s-Pg CH ₂ SO ₂ Me H Br 6-15 s-Pg Cl ch ₂ och ₂ cf ₃ SO ₂ Me 6-16 s-Pg Cl ch ₂ och ₂ cf ₃ SMe 6-17 s-Pg Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-18 s-Pg Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-19 s-Pg Cl CH ₂ OCH ₂ tetrahydrofuran-2-yl SO ₂ Me 6-20 s-Pg Cl SMe Cl 6-21 s-Pg Cl SMe SO ₂ Me 6-22 s-Pg Cl Me SO ₂ Et 6-23 s-Pg Cl O (CH ₂ ) ₂ OMe Cl 6-24 s-Pg Cl OCH ₂ cyclopropyl Cl 6-25 s-Pg Cl OME Cl 6-26 s-Pg Cl NHAc Cl 6-27 s-Pg Cl OCH ₂ C(O)NMe ₂ Cl

- 57 040923

6-28 c-Pr Cl Cl SO ₂ Me 6-29 c-Pr Cl pyrazol-1-yl SO ₂ Me 6-30 c-Pr Cl 4- methoxypyrazol1-yl SO ₂ Me 6-31 c-Pr Cl 1,2,3-triazol-1yl SO ₂ Me 6-32 c-Pr Cl 1,2,3-triazole-2- silt SO ₂ Me 6-33 c-Pr Cl F SO ₂ Me 6-34 c-Pr Me SO ₂ Me SO ₂ Me 6-35 c-Pr Me SO ₂ Me _CF3 6-36 c-Pr Me NMe ₂ SO ₂ Me 6-37 c-Pr Me S(O)Me _CF3 6-38 c-Pr Me SMe _CF3 6-39 c-Pr Me _{SO2CH2CH2OMe _ _ CF3} 6-40 c-Pr Me pyrazol-1-yl SO ₂ Me 6-41 c-Pr Me 4-methoxypyrazol-1-yl SO ₂ Me 6-42 c-Pr Me 1,2,3-triazole-1- silt SO ₂ Me 6-43 c-Pr Me 1,2,3-triazole-2- silt SO ₂ Me 6-44 c-Pr Me C1 SO ₂ Me 6-45 c-Pr Me Me SO ₂ Me 6-46 c-Pr Me F Cl 6-47 c-Pr Me SO ₂ Me Cl 6-48 c-Pr Me NMe ₂ SO ₂ Me 6-49 c-Pr Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-50 c-Pr _CF3 F _{SO2CH3 _} 6-51 c-Pr _CF3 SMe _{SO2CH3 _} 6-52 c-Pr _CF3 SEt _{SO2CH3 _} 6-53 c-Pr _CF3 S(O)Et _{SO2CH3 _} 6-54 c-Pr _{CF3 SO2CH3 _ SO2CH3 _} 6-55 c-Pr _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-56 c-Pr _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-57 c-Pr _CF3 CH ₂ Tetrahydrofuran-2-yl SO ₂ Et 6-58 c-Pr SMe SMe F 6-59 c-Pr SMe SEt F 6-60 c-Pr _{SO2CH3 _} F Cl 6-61 c-Pr F S(O)Me _CF3 6-62 c-Pr F SMe _CF3 6-63 _CO2et no ₂ H SO ₂ Me 6-64 _CO2et Cl H SO ₂ Me 6-65 _CO2et SO ₂ Me H _CF3

- 58 040923

6-66 _CO2et no ₂ H ome 6-67 _CO2et no ₂ H Br 6-68 _CO2et no ₂ H _CF3 6-69 _CO2et no ₂ H no ₂ 6-70 _CO2et no ₂ H Cl 6-71 _CO2et no ₂ H Me 6-72 _CO2et no ₂ H F 6-73 _CO2et ome H SO ₂ Me 6-74 _{CO2et CF3} H no ₂ 6-75 _CO2et CH ₂ SO ₂ Me H Br 6-76 _CO2et Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-77 _CO2et Cl ch ₂ och ₂ cf ₃ SMe 6-78 _CO2et Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-79 _CO2et Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-80 _CO2et Cl CH ₂ OCH ₂ tetrahydrofuran-2-yl SO ₂ Me 6-81 _CO2et Cl SMe Cl 6-82 _CO2et Cl SMe SO ₂ Me 6-83 _CO2et Cl Me SO ₂ Et 6-84 _CO2et Cl O (CH ₂ ) ₂ OMe Cl 6-85 _CO2et Cl OCH ₂ cyclopropyl Cl 6-86 _CO2et Cl OME Cl 6-87 _CO2et Cl NHAc Cl 6-88 _CO2et Cl OCH ₂ C(O)NMe ₂ Cl 6-89 _CO2et Cl Cl SO ₂ Me 6-90 _CO2et Cl pyrazol-1-yl SO ₂ Me 6-91 _CO2et Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-92 _CO2et Cl 1,2,3-triazol-1yl SO ₂ Me 6-93 _CO2et Cl 1,2,3-triazole-2- silt SO ₂ Me 6-94 _CO2et Cl F SO ₂ Me 6-95 _CO2et Me SO ₂ Me SO ₂ Me 6-96 _CO2et Me SO ₂ Me _CF3 6-97 _CO2et Me NMe ₂ SO ₂ Me 6-98 _CO2et Me S(O)Me _CF3 6-99 _CO2et Me SMe _CF3 6-100 _CO2et Me _{SO2CH2CH2OMe _ _ CF3} 6-101 _CO2et Me pyrazol-1-yl SO ₂ Me

- 59 040923

6-102 _CO2et Me 4- methoxypyrazol1-yl SO ₂ Me 6-103 _CO2et Me 1,2,3-triazol-1yl SO ₂ Me 6-104 _CO2et Me 1,2,3-triazole-2- silt SO ₂ Me 6-105 _CO2et Me Cl SO ₂ Me 6-106 _CO2et Me Me SO ₂ Me 6-107 _CO2et Me Me SMe 6-108 _CO2et Me SO ₂ Me Cl 6-109 _CO2et Me NMe ₂ SO ₂ Me 6-110 _CO2et Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-111 _{CO2et CF3} F _{SO2CH3 _} 6-112 _{CO2et CF3} SMe _{SO2CH3 _} 6-113 _{CO2et CF3} SEt _{SO2CH3 _} 6-114 _{CO2et CF3} S(O)Et _{SO2CH3 _} 6-115 _{CO2et CF3 SO2CH3 _ SO2CH3 _} 6-116 _{CO2et CF3 OCH2CH2OMe _ SO2CH3 _} 6-117 _{CO2et CF3} OCH ₂ (CO)NMe ₂ SO2Me 6-118 _{CO2et CF3} CH ₂ Tetrahydrofuran-2-yl SO ₂ Et 6-119 _CO2et SMe SMe F 6-120 _CO2et SMe SEt F 6-121 _{CO2et SO2CH3 _} F Cl 6-122 _CO2et F S(O)Me _CF3 6-123 _CO2et F SMe _CF3 6-124 CO ₂ Me no ₂ H SO ₂ Me 6-125 CO ₂ Me Cl H SO ₂ Me 6-126 CO ₂ Me SO ₂ Me H _CF3 6-127 CO ₂ Me no ₂ H ome 6-128 CO ₂ Me no ₂ H Br 6-129 CO ₂ Me no ₂ H _CF3 6-130 CO ₂ Me no ₂ H no ₂ 6-131 CO ₂ Me no ₂ H Cl 6-132 CO ₂ Me no ₂ H Me 6-133 CO ₂ Me no ₂ H F 6-134 CO ₂ Me ome H SO ₂ Me 6-135 CO ₂ Me _CF3 H no ₂ 6-136 CO ₂ Me CH ₂ SO ₂ Me H Br 6-137 CO ₂ Me Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-138 CO ₂ Me Cl ch ₂ och ₂ cf ₃ SMe 6-139 CO ₂ Me Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et

- 60 040923

6-140 CO ₂ Me C1 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-141 CO ₂ Me C1 CH ₂ OCH ₂ tetrahydrofuran-2-yl SO ₂ Me 6-142 CO ₂ Me C1 SMe Cl 6-143 CO ₂ Me C1 SMe SO ₂ Me 6-144 CO ₂ Me C1 Me SO ₂ Et 6-145 CO ₂ Me C1 O(CH ₂ ) ₂ OMe Cl 6-146 CO ₂ Me C1 OCH ₂ cyclopropyl Cl 6-147 CO ₂ Me C1 ome Cl 6-148 CO ₂ Me C1 NHAc Cl 6-149 CO ₂ Me C1 OCH ₂ C(O)NMe ₂ Cl 6-150 CO ₂ Me C1 Cl SO ₂ Me 6-151 CO ₂ Me C1 pyrazol-1-yl SO ₂ Me 6-152 CO ₂ Me C1 4- methoxypyrazol1-yl SO ₂ Me 6-153 CO ₂ Me C1 1,2,3-triazole-1- silt SO ₂ Me 6-154 CO ₂ Me C1 1,2,3-triazole-2- silt SO ₂ Me 6-155 CO ₂ Me C1 F SO ₂ Me 6-156 CO ₂ Me Me SO ₂ Me SO ₂ Me 6-157 CO ₂ Me Me SO ₂ Me _CF3 6-158 CO ₂ Me Me NMe ₂ SO ₂ Me 6-159 CO ₂ Me Me S(O)Me _CF3 6-160 CO ₂ Me Me SMe _CF3 6-161 CO ₂ Me Me _{SO2CH2CH2OMe _ _ CF3} 6-162 CO ₂ Me Me pyrazol-1-yl SO ₂ Me 6-163 CO ₂ Me Me 4- methoxypyrazol1-yl SO ₂ Me 6-164 CO ₂ Me Me 1,2,3-triazol-1yl SO ₂ Me 6-165 CO ₂ Me Me 1,2,3-triazole-2- silt SO ₂ Me 6-166 CO ₂ Me Me C1 SO ₂ Me 6-167 CO ₂ Me Me Me SO ₂ Me 6-168 CO ₂ Me Me Me SMe 6-169 CO ₂ Me Me SO ₂ Me Cl 6-170 CO ₂ Me Me NMe ₂ SO ₂ Me 6-171 CO ₂ Me Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-172 CO ₂ Me _CF3 F _{SO2CH3 _} 6-173 CO ₂ Me _CF3 SMe _{SO2CH3 _} 6-174 CO ₂ Me _CF3 SEt _{SO2CH3 _}

- 61 040923

6-175 CO ₂ Me _CF3 S(O)Et _{SO2CH3 _} 6-176 CO ₂ Me _{CF3 SO2CH3 _ SO2CH3 _} 6-177 CO ₂ Me _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-178 CO ₂ Me _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-179 CO ₂ Me _CF3 CH ₂ Tetrahydrofuran-2-yl SO ₂ Et 6-180 CO ₂ Me SMe SMe F 6-181 CO ₂ Me SMe SEt F 6-182 CO ₂ Me _{SO2CH3 _} F Cl 6-183 CO ₂ Me F S(O)Me _CF3 6-184 CO ₂ Me F SMe _CF3 6-185 benzyl no ₂ H SO ₂ Me 6-186 benzyl Cl H SO ₂ Me 6-187 benzyl SO ₂ Me H _CF3 6-188 benzyl no ₂ H ome 6-189 benzyl no ₂ H Br 6-190 benzyl no ₂ H _CF3 6-191 benzyl no ₂ H no ₂ 6-192 benzyl no ₂ H Cl 6-193 benzyl no ₂ H Me 6-194 benzyl no ₂ H F 6-195 benzyl ome H SO ₂ Me 6-196 benzyl _CF3 H no ₂ 6-197 benzyl CH ₂ SO ₂ Me H Br 6-198 benzyl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-199 benzyl Cl ch ₂ och ₂ cf ₃ SMe 6-200 benzyl Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-201 benzyl Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-202 benzyl Cl CH ₂ OCH ₂ tetrahydrofuran-2-yl SO ₂ Me 6-203 benzyl Cl SMe Cl 6-204 benzyl Cl SMe SO ₂ Me 6-205 benzyl Cl Me SO ₂ Et 6-206 benzyl Cl O (CH ₂ ) ₂ OMe Cl 6-207 benzyl Cl OCH ₂ cyclopropyl Cl 6-208 benzyl Cl OME Cl 6-209 benzyl Cl NHAc Cl 6-210 benzyl Cl OCH ₂ C(O)NMe ₂ Cl 6-211 benzyl Cl Cl SO ₂ Me 6-212 benzyl Cl pyrazol-1-yl SO ₂ Me

- 62 040923

6-213 benzyl C1 4- methoxypyrazol1-yl SO ₂ Me 6-214 benzyl C1 1,2,3-triazol-1yl SO ₂ Me 6-215 benzyl C1 1,2,3-triazole-2- silt SO ₂ Me 6-216 benzyl C1 F SO ₂ Me 6-217 benzyl Me SO ₂ Me SO ₂ Me 6-218 benzyl Me SO ₂ Me _CF3 6-219 benzyl Me NMe ₂ SO ₂ Me 6-220 benzyl Me S(O)Me _CF3 6-221 benzyl Me SMe _CF3 6-222 benzyl Me _{SO2CH2CH2OMe _ _ CF3} 6-223 benzyl Me pyrazol-1-yl SO ₂ Me 6-224 benzyl Me 4- methoxypyrazol1-yl SO ₂ Me 6-225 benzyl Me 1,2,3-triazol-1yl SO ₂ Me 6-226 benzyl Me 1,2,3-triazole-2- silt SO ₂ Me 6-227 benzyl Me C1 SO ₂ Me 6-228 benzyl Me Me SO ₂ Me 6-229 benzyl Me Me SMe 6-230 benzyl Me SO ₂ Me Cl 6-231 benzyl Me NMe ₂ SO ₂ Me 6-232 benzyl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-233 benzyl _CF3 F _{SO2CH3 _} 6-234 benzyl _CF3 SMe _{SO2CH3 _} 6-235 benzyl _CF3 SEt _{SO2CH3 _} 6-236 benzyl _CF3 S(O)Et _{SO2CH3 _} 6-237 benzyl _{CF3 SO2CH3 _ SO2CH3 _} 6-238 benzyl _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-239 benzyl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-240 benzyl _CF3 CH ₂ Tetrahydrofuran-2-yl SO ₂ Et 6-241 benzyl SMe SMe F 6-242 benzyl SMe SEt F 6-243 benzyl _{SO2CH3 _} F Cl 6-244 benzyl F S(O)Me _CF3 6-245 benzyl F SMe _CF3 6-246 phenyl no ₂ H SO ₂ Me 6-247 phenyl Cl H SO ₂ Me 6-248 phenyl SO ₂ Me H _CF3 6-249 phenyl no ₂ H ome

- 63 040923

6-250 phenyl no ₂ H Br 6-251 phenyl no ₂ H _CF3 6-252 phenyl no ₂ H no ₂ 6-253 phenyl no ₂ H Cl 6-254 phenyl no ₂ H Me 6-255 phenyl no ₂ H F 6-256 phenyl ome H SO ₂ Me 6-257 phenyl _CF3 H no ₂ 6-258 phenyl CH ₂ SO ₂ Me H Br 6-259 phenyl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-260 phenyl Cl ch ₂ och ₂ cf ₃ SMe 6-261 phenyl Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-262 phenyl Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-263 phenyl Cl CH ₂ OCH ₂ tetrahydrofuran-2-yl SO ₂ Me 6-264 phenyl Cl SMe Cl 6-265 phenyl Cl SMe SO ₂ Me 6-266 phenyl Cl Me SO ₂ Et 6-267 phenyl Cl O (CH ₂ ) ₂ OMe Cl 6-268 phenyl Cl OCH ₂ cyclopropyl Cl 6-269 phenyl Cl OME Cl 6-270 phenyl Cl NHAc Cl 6-271 phenyl Cl OCH ₂ C(O)NMe ₂ Cl 6-272 phenyl Cl Cl SO ₂ Me 6-273 phenyl Cl pyrazol-1-yl SO ₂ Me 6-274 phenyl Cl 4- methoxypyrazol1-yl SO ₂ Me 6-275 phenyl Cl 1,2,3-triazol-1yl SO ₂ Me 6-276 phenyl Cl 1,2,3-triazol-2yl SO ₂ Me 6-277 phenyl Cl F SO ₂ Me 6-278 phenyl Me SO ₂ Me SO ₂ Me 6-279 phenyl Me SO ₂ Me _CF3 6-280 phenyl Me NMe ₂ SO ₂ Me 6-281 phenyl Me S(O)Me _CF3 6-282 phenyl Me SMe _CF3 6-283 phenyl Me _{SO2CH2CH2OMe _ _ CF3} 6-284 phenyl Me pyrazol-1-yl SO ₂ Me

- 64 040923

6-285 phenyl Me 4- methoxypyrazol1-yl SO ₂ Me 6-286 phenyl Me 1,2,3-triazole-1- silt SO ₂ Me 6-287 phenyl Me 1,2,3-triazole-2- silt SO ₂ Me 6-288 phenyl Me Cl SO ₂ Me 6-289 phenyl Me Me SO ₂ Me 6-290 phenyl Me Me SMe 6-291 phenyl Me SO ₂ Me Cl 6-292 phenyl Me NMe ₂ SO ₂ Me 6-293 phenyl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-294 phenyl _CF3 F _{SO2CH3 _} 6-295 phenyl _CF3 SMe _{SO2CH3 _} 6-296 phenyl _CF3 SEt _{SO2CH3 _} 6-297 phenyl _CF3 S(O)Et _{SO2CH3 _} 6-298 phenyl _{CF3 SO2CH3 _ SO2CH3 _} 6-299 phenyl _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-300 phenyl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-301 phenyl _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-302 phenyl SMe SMe F 6-303 phenyl SMe SEt F 6-304 phenyl _{SO2CH3 _} F Cl 6-305 phenyl F S(O)Me _CF3 6-306 phenyl F SMe _CF3 6-307 pyrazin-2-yl no ₂ H SO ₂ Me 6-308 pyrazin-2-yl Cl H SO ₂ Me 6-309 pyrazin-2-yl SO ₂ Me H _CF3 6-310 pyrazin-2-yl no ₂ H ome 6-311 pyrazin-2-yl no ₂ H Br 6-312 pyrazin-2-yl no ₂ H _CF3 6-313 pyrazin-2-yl no ₂ H no ₂ 6-314 pyrazin-2-yl no ₂ H Cl 6-315 pyrazin-2-yl no ₂ H Me 6-316 pyrazin-2-yl no ₂ H F 6-317 pyrazin-2-yl ome H SO ₂ Me 6-318 pyrazin-2-yl _CF3 H no ₂ 6-319 pyrazin-2-yl CH ₂ SO ₂ Me H Br 6-320 pyrazin-2-yl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-321 pyrazin-2-yl Cl ch ₂ och ₂ cf ₃ SMe 6-322 pyrazin-2-yl Cl 5-cyanomethyl4,5-dihydro-1,2oxazol-3-yl SO ₂ Et

- 65 040923

6-323 pyrazin-2-yl Cl 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et 6-324 pyrazin-2-yl Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-325 pyrazin-2-yl Cl SMe Cl 6-326 pyrazin-2-yl Cl SMe SO ₂ Me 6-327 pyrazin-2-yl Cl Me SO ₂ Et 6-328 pyrazin-2-yl Cl O(CH ₂ ) ₂ OMe Cl 6-329 pyrazin-2-yl Cl OCH ₂ cyclopropyl Cl 6-330 pyrazin-2-yl Cl OME Cl 6-331 pyrazin-2-yl Cl NHAc Cl 6-332 pyrazin-2-yl Cl OCH ₂ C(O)NMe ₂ Cl 6-333 pyrazin-2-yl Cl Cl SO ₂ Me 6-334 pyrazin-2-yl Cl pyrazol-1-yl SO ₂ Me 6-335 pyrazin-2-yl Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-336 pyrazin-2-yl Cl 1,2,3-triazol-1yl SO ₂ Me 6-337 pyrazin-2-yl Cl 1,2,3-triazole-2- silt SO ₂ Me 6-338 pyrazin-2-yl Cl F SO ₂ Me 6-339 pyrazin-2-yl Me SO ₂ Me SO ₂ Me 6-340 pyrazin-2-yl Me SO ₂ Me _CF3 6-341 pyrazin-2-yl Me NMe ₂ SO ₂ Me 6-342 pyrazin-2-yl Me S(O)Me _CF3 6-343 pyrazin-2-yl Me SMe _CF3 6-344 pyrazin-2-yl Me _{SO2CH2CH2OMe _ _ CF3} 6-345 pyrazin-2-yl Me pyrazol-1-yl SO ₂ Me 6-346 pyrazin-2-yl Me 4-methoxypyrazol-1-yl SO ₂ Me 6-347 pyrazin-2-yl Me 1,2,3-triazol-1yl SO ₂ Me 6-348 pyrazin-2-yl Me 1,2,3-triazole-2- silt SO ₂ Me 6-349 pyrazin-2-yl Me C1 SO ₂ Me 6-350 pyrazin-2-yl Me Me SO ₂ Me 6-351 pyrazin-2-yl Me Me SMe 6-352 pyrazin-2-yl Me SO ₂ Me Cl 6-353 pyrazin-2-yl Me NMe ₂ SO ₂ Me 6-354 pyrazin-2-yl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-355 pyrazin-2-yl _CF3 F _{SO2CH3 _} 6-356 pyrazin-2-yl _CF3 SMe _{SO2CH3 _} 6-357 pyrazin-2-yl _CF3 SEt _{SO2CH3 _} 6-358 pyrazin-2-yl _CF3 S(O)Et _{SO2CH3 _} 6-359 pyrazin-2-yl _{CF3 SO2CH3 _ SO2CH3 _} 6-360 pyrazin-2-yl _{CF3 OCH2CH2OMe _ SO2CH3 _}

- 66 040923

6-361 pyrazin-2-yl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-362 pyrazin-2-yl _CF3 CH ₂ O-tetrahydro-furan-2-yl SO ₂ Et 6-363 pyrazin-2-yl SMe SMe F 6-364 pyrazin-2-yl SMe SEt F 6-365 pyrazin-2-yl _{SO2CH3 _} F Cl 6-366 pyrazin-2-yl F S(O)Me _CF3 6-367 pyrazin-2-yl F SMe _CF3 6-368 4-OMe-Ph no ₂ H SO ₂ Me 6-369 4-OMe-Ph Cl H SO ₂ Me 6-370 4-OMe-Ph SO ₂ Me H _CF3 6-371 4-OMe-Ph no ₂ H ome 6-372 4-OMe-Ph no ₂ H Br 6-373 4-OMe-Ph no ₂ H _CF3 6-374 4-OMe-Ph no ₂ H no ₂ 6-375 4-OMe-Ph no ₂ H Cl 6-376 4-OMe-Ph no ₂ H Me 6-377 4-OMe-Ph no ₂ H F 6-378 4-OMe-Ph ome H SO ₂ Me 6-379 4-OMe-Ph _CF3 H no ₂ 6-380 4-OMe-Ph CH ₂ SO ₂ Me H Br 6-381 4-OMe-Ph Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-382 4-OMe-Ph Cl ch ₂ och ₂ cf ₃ SMe 6-383 4-OMe-Ph Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-384 4-OMe-Ph Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-385 4-OMe-Ph Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-386 4-OMe-Ph Cl SMe Cl 6-387 4-OMe-Ph Cl SMe SO ₂ Me 6-388 4-OMe-Ph Cl Me SO ₂ Et 6-389 4-OMe-Ph Cl O (CH ₂ ) ₂ OMe Cl 6-390 4-OMe-Ph Cl OCH ₂ cyclopropyl Cl 6-391 4-OMe-Ph Cl OME Cl 6-392 4-OMe-Ph Cl NHAc Cl 6-393 4-OMe-Ph Cl OCH ₂ C(O)NMe ₂ Cl 6-394 4-OMe-Ph Cl Cl SO ₂ Me 6-395 4-OMe-Ph Cl pyrazol-1-yl SO ₂ Me 6-396 4-OMe-Ph Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-397 4-OMe-Ph Cl 1,2,3-triazole-1- silt SO ₂ Me

- 67 040923

6-398 4-OMe-Ph Cl 1,2,3-triazole-2- IL SO ₂ Me 6-399 4-OMe-Ph Cl F SO ₂ Me 6-400 4-OMe-Ph Me SO ₂ Me SO ₂ Me 6-401 4-OMe-Ph Me SO ₂ Me _CF3 6-402 4-OMe-Ph Me NMe ₂ SO ₂ Me 6-403 4-OMe-Ph Me S(O)Me _CF3 6-404 4-OMe-Ph Me SMe _CF3 6-405 4-OMe-Ph Me _{SO2CH2CH2OMe _ _ CF3} 6-406 4-OMe-Ph Me pyrazol-1-yl SO ₂ Me 6-407 4-OMe-Ph Me 4-methoxypyrazol-1-yl SO ₂ Me 6-408 4-OMe-Ph Me 1,2,3-triazol-1yl SO ₂ Me 6-409 4-OMe-Ph Me 1,2,3-triazol-2yl SO ₂ Me 6-410 4-OMe-Ph Me C1 SO ₂ Me 6-411 4-OMe-Ph Me Me SO ₂ Me 6-412 4-OMe-Ph Me Me SMe 6-413 4-OMe-Ph Me SO ₂ Me Cl 6-414 4-OMe-Ph Me NMe ₂ SO ₂ Me 6-415 4-OMe-Ph Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-416 4-OMe-Ph _CF3 F _{SO2CH3 _} 6-417 4-OMe-Ph _CF3 SMe _{SO2CH3 _} 6-418 4-OMe-Ph _CF3 SEt _{SO2CH3 _} 6-419 4-OMe-Ph _CF3 S(O)Et _{SO2CH3 _} 6-420 4-OMe-Ph _{CF3 SO2CH3 _ SO2CH3 _} 6-421 4-OMe-Ph _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-422 4-OMe-Ph _CF3 OCH ₂ (CO)NMe ₂ SO ₂ Me 6-423 4-OMe-Ph _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-424 4-OMe-Ph SMe SMe F 6-425 4-OMe-Ph SMe SEt F 6-426 4-OMe-Ph _{SO2CH3 _} F Cl 6-427 4-OMe-Ph F S(O)Me _CF3 6-428 4-OMe-Ph F SMe _CF3 6-429 4-Cl-Ph no ₂ H SO ₂ Me 6-430 4-Cl-Ph Cl H SO ₂ Me 6-431 4-Cl-Ph SO ₂ Me H _CF3 6-432 4-Cl-Ph no ₂ H ome 6-433 4-Cl-Ph no ₂ H Br 6-434 4-Cl-Ph no ₂ H _CF3 6-435 4-Cl-Ph no ₂ H no ₂ 6-436 4-Cl-Ph no ₂ H Cl 6-437 4-Cl-Ph no ₂ H Me 6-438 4-Cl-Ph no ₂ H F 6-439 4-Cl-Ph ome H SO ₂ Me

- 68 040923

6-440 4-Cl-Ph _CF3 H no ₂ 6-441 4-Cl-Ph CH ₂ SO ₂ Me H Br 6-442 4-Cl-Ph Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-443 4-Cl-Ph Cl ch ₂ och ₂ cf ₃ SMe 6-444 4-Cl-Ph Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-445 4-Cl-Ph Cl 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et 6-446 4-Cl-Ph Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-447 4-Cl-Ph Cl SMe Cl 6-448 4-Cl-Ph Cl SMe SO ₂ Me 6-449 4-Cl-Ph Cl Me SO ₂ Et 6-450 4-Cl-Ph Cl O (CH ₂ ) ₂ OMe Cl 6-451 4-Cl-Ph Cl OCH ₂ cyclopropyl Cl 6-452 4-Cl-Ph Cl OME Cl 6-453 4-Cl-Ph Cl NHAc Cl 6-454 4-Cl-Ph Cl OCH ₂ C(O)NMe ₂ Cl 6-455 4-Cl-Ph Cl Cl SO ₂ Me 6-456 4-Cl-Ph Cl pyrazole-Peel SO ₂ Me 6-457 4-Cl-Ph Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-458 4-Cl-Ph Cl 1,2,3-triazol-1yl SO ₂ Me 6-459 4-Cl-Ph Cl 1,2,3-triazole-2- silt SO ₂ Me 6-460 4-Cl-Ph Cl F SO ₂ Me 6-461 4-Cl-Ph Me SO ₂ Me SO ₂ Me 6-462 4-Cl-Ph Me SO ₂ Me _CF3 6-463 4-Cl-Ph Me NMe ₂ SO ₂ Me 6-464 4-Cl-Ph Me S(O)Me _CF3 6-465 4-Cl-Ph Me SMe _CF3 6-466 4-Cl-Ph Me _{SO2CH2CH2OMe _ _ CF3} 6-467 4-Cl-Ph Me pyrazol-1-yl SO ₂ Me 6-468 4-Cl-Ph Me 4-methoxypyrazol-1-yl SO ₂ Me 6-469 4-Cl-Ph Me 1,2,3-triazole-1- silt SO ₂ Me 6-470 4-Cl-Ph Me 1,2,3-triazole-2- silt SO ₂ Me 6-471 4-Cl-Ph Me C1 SO ₂ Me 6-472 4-Cl-Ph Me Me SO ₂ Me 6-473 4-Cl-Ph Me Me SMe 6-474 4-Cl-Ph Me SO ₂ Me Cl

- 69 040923

6-475 4-Cl-Ph Me NMe ₂ SO ₂ Me 6-476 4-Cl-Ph Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-477 4-Cl-Ph _CF3 F _{SO2CH3 _} 6-478 4-Cl-Ph _CF3 SMe _{SO2CH3 _} 6-479 4-Cl-Ph _CF3 SEt _{SO2CH3 _} 6-480 4-Cl-Ph _CF3 S(O)Et _{SO2CH3 _} 6-481 4-Cl-Ph _{CF3 SO2CH3 _ SO2CH3 _} 6-482 4-Cl-Ph _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-483 4-Cl-Ph _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-484 4-Cl-Ph _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-485 4-Cl-Ph SMe SMe F 6-486 4-Cl-Ph SMe SEt F 6-487 4-Cl-Ph _{SO2CH3 _} F Cl 6-488 4-Cl-Ph F S(O)Me _CF3 6-489 4-Cl-Ph F SMe _CF3 6-490 tert-butyl no ₂ H SO ₂ Me 6-491 tert-butyl Cl H SO ₂ Me 6-492 tert-butyl SO ₂ Me H _CF3 6-493 tert-butyl no ₂ H ome 6-494 tert-butyl no ₂ H Br 6-495 tert-butyl no ₂ H _CF3 6-496 tert-butyl no ₂ H no ₂ 6-497 tert-butyl no ₂ H Cl 6-498 tert-butyl no ₂ H Me 6-499 tert-butyl no ₂ H F 6-500 tert-butyl ome H SO ₂ Me 6-501 tert-butyl _CF3 H no ₂ 6-502 tert-butyl CH ₂ SO ₂ Me H Br 6-503 tert-butyl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-504 tert-butyl Cl ch ₂ och ₂ cf ₃ SMe 6-505 tert-butyl Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-506 tert-butyl Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-507 tert-butyl Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-508 tert-butyl Cl SMe Cl 6-509 tert-butyl Cl SMe SO ₂ Me 6-510 tert-butyl Cl Me SO ₂ Et 6-511 tert-butyl Cl O (CH ₂ ) ₂ OMe Cl 6-512 tert-butyl Cl OCH ₂ cyclopropyl Cl 6-513 tert-butyl Cl OME Cl 6-514 tert-butyl Cl NHAc Cl

- 70 040923

6-515 tert-butyl C1 OCH ₂ C(O)NMe ₂ Cl 6-516 tert-butyl C1 Cl SO ₂ Me 6-517 tert-butyl C1 pyrazol-1-yl SO ₂ Me 6-518 tert-butyl C1 4-methoxypyrazol-1-yl SO ₂ Me 6-519 tert-butyl C1 1,2,3-triazol-1yl SO ₂ Me 6-520 tert-butyl C1 1,2,3-triazole-2- silt SO ₂ Me 6-521 tert-butyl C1 F SO ₂ Me 6-522 tert-butyl Me SO ₂ Me SO ₂ Me 6-523 tert-butyl Me SO ₂ Me _CF3 6-524 tert-butyl Me NMe ₂ SO ₂ Me 6-525 tert-butyl Me S(O)Me _CF3 6-526 tert-butyl Me SMe _CF3 6-527 tert-butyl Me _{SO2CH2CH2OMe _ _ CF3} 6-528 tert-butyl Me pyrazol-1-yl SO ₂ Me 6-529 tert-butyl Me 4-methoxypyrazol-1-yl SO ₂ Me 6-530 tert-butyl Me 1,2,3-triazole-1- silt SO ₂ Me 6-531 tert-butyl Me 1,2,3-triazole-2- silt SO ₂ Me 6-532 tert-butyl Me C1 SO ₂ Me 6-533 tert-butyl Me Me SO ₂ Me 6-534 tert-butyl Me Me SMe 6-535 tert-butyl Me SO ₂ Me Cl 6-536 tert-butyl Me NMe ₂ SO ₂ Me 6-537 tert-butyl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-538 tert-butyl _CF3 F _{SO2CH3 _} 6-539 tert-butyl _CF3 SMe _{SO2CH3 _} 6-540 tert-butyl _CF3 SEt _{SO2CH3 _} 6-541 tert-butyl _CF3 S(O)Et _{SO2CH3 _} 6-542 tert-butyl _{CF3 SO2CH3 _ SO2CH3 _} 6-543 tert-butyl _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-544 tert-butyl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-545 tert-butyl _CF3 CH ₂ Tetrahydrofuran-2-yl SO ₂ Et 6-546 tert-butyl SMe SMe F 6-547 tert-butyl SMe SEt F 6-548 tert-butyl _{SO2CH3 _} F Cl 6-549 tert-butyl F S(O)Me _CF3 6-550 tert-butyl F SMe _CF3 6-551 furan-2-yl no ₂ H SO ₂ Me 6-552 furan-2-yl Cl H SO ₂ Me 6-553 furan-2-yl SO ₂ Me H _CF3

- 71 040923

6-554 furan-2-yl no ₂ H ome 6-555 furan-2-yl no ₂ H Br 6-556 furan-2-yl no ₂ H _CF3 6-557 furan-2-yl no ₂ H no ₂ 6-558 furan-2-yl no ₂ H Cl 6-559 furan-2-yl no ₂ H Me 6-560 furan-2-yl no ₂ H F 6-561 furan-2-yl ome H SO ₂ Me 6-562 furan-2-yl _CF3 H no ₂ 6-563 furan-2-yl CH ₂ SO ₂ Me H Br 6-564 furan-2-yl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-565 furan-2-yl Cl ch ₂ och ₂ cf ₃ SMe 6-566 furan-2-yl Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-567 furan-2-yl Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-568 furan-2-yl Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-569 furan-2-yl Cl SMe Cl 6-570 furan-2-yl Cl SMe SO ₂ Me 6-571 furan-2-yl Cl Me SO ₂ Et 6-572 furan-2-yl Cl O (CH ₂ ) ₂ OMe Cl 6-573 furan-2-yl Cl OCH ₂ cyclopropyl Cl 6-574 furan-2-yl Cl OME Cl 6-575 furan-2-yl Cl NHAc Cl 6-576 furan-2-yl Cl OCH ₂ C(O)NMe ₂ Cl 6-577 furan-2-yl Cl Cl SO ₂ Me 6-578 furan-2-yl Cl pyrazol-1-yl SO ₂ Me 6-579 furan-2-yl Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-580 furan-2-yl Cl 1,2,3-triazole-1- silt SO ₂ Me 6-581 furan-2-yl Cl 1,2,3-triazole-2- silt SO ₂ Me 6-582 furan-2-yl Cl F SO ₂ Me 6-583 furan-2-yl Me SO ₂ Me SO ₂ Me 6-584 furan-2-yl Me SO ₂ Me _CF3 6-585 furan-2-yl Me NMe ₂ SO ₂ Me 6-586 furan-2-yl Me S(O)Me _CF3 6-587 furan-2-yl Me SMe _CF3 6-588 furan-2-yl Me _{SO2CH2CH2OMe _ _ CF3} 6-589 furan-2-yl Me pyrazol-1-yl SO ₂ Me 6-590 furan-2-yl Me 4-methoxypyrazol-1-yl SO ₂ Me

- 72 040923

6-591 furan-2-yl Me 1,2,3-triazole-1- IL SO ₂ Me 6-592 furan-2-yl Me 1,2,3-triazol-2yl SO ₂ Me 6-593 furan-2-yl Me Cl SO ₂ Me 6-594 furan-2-yl Me Me SO ₂ Me 6-595 furan-2-yl Me Me SMe 6-596 furan-2-yl Me SO ₂ Me Cl 6-597 furan-2-yl Me NMe ₂ SO ₂ Me 6-598 furan-2-yl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-599 furan-2-yl _CF3 F _{SO2CH3 _} 6-600 furan-2-yl _CF3 SMe _{SO2CH3 _} 6-601 furan-2-yl _CF3 SEt _{SO2CH3 _} 6-602 furan-2-yl _CF3 S(O)Et _{SO2CH3 _} 6-603 furan-2-yl _{CF3 SO2CH3 _ SO2CH3 _} 6-604 furan-2-yl _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-605 furan-2-yl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-606 furan-2-yl _CF3 CH ₂ O-tetrahydrofuran- 2-yl SO ₂ Et 6-607 furan-2-yl SMe SMe F 6-608 furan-2-yl SMe SEt F 6-609 furan-2-yl _{SO2CH3 _} F Cl 6-610 furan-2-yl F S(O)Me _CF3 6-611 furan-2-yl F SMe _CF3 6-612 isopropyl no ₂ H SO ₂ Me 6-613 isopropyl Cl H SO ₂ Me 6-614 isopropyl SO ₂ Me H _CF3 6-615 isopropyl no ₂ H ome 6-616 isopropyl no ₂ H Br 6-617 isopropyl no ₂ H _CF3 6-618 isopropyl no ₂ H no ₂ 6-619 isopropyl no ₂ H Cl 6-620 isopropyl no ₂ H Me 6-621 isopropyl no ₂ H F 6-622 isopropyl ome H SO ₂ Me 6-623 isopropyl _CF3 H no ₂ 6-624 isopropyl CH ₂ SO ₂ Me H Br 6-625 isopropyl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-626 isopropyl Cl ch ₂ och ₂ cf ₃ SMe 6-627 isopropyl Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-628 isopropyl Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-629 isopropyl Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me

- 73 040923

6-630 isopropyl C1 SMe Cl 6-631 isopropyl C1 SMe SO ₂ Me 6-632 isopropyl C1 Me SO ₂ Et 6-633 isopropyl C1 O(CH ₂ ) ₂ OMe Cl 6-634 isopropyl C1 OCH ₂ cyclopropyl Cl 6-635 isopropyl C1 ome Cl 6-636 isopropyl C1 NHAc Cl 6-637 isopropyl C1 OCH ₂ C(O)NMe ₂ Cl 6-638 isopropyl C1 Cl SO ₂ Me 6-639 isopropyl C1 pyrazol-1-yl SO ₂ Me 6-640 isopropyl C1 4-methoxypyrazol-1-yl SO ₂ Me 6-641 isopropyl C1 1,2,3-triazol-1yl SO ₂ Me 6-642 isopropyl C1 1,2,3-triazole-2- silt SO ₂ Me 6-643 isopropyl C1 F SO ₂ Me 6-644 isopropyl Me SO ₂ Me SO ₂ Me 6-645 isopropyl Me SO ₂ Me _CF3 6-646 isopropyl Me NMe ₂ SO ₂ Me 6-647 isopropyl Me S(O)Me _CF3 6-648 isopropyl Me SMe _CF3 6-649 isopropyl Me _{SO2CH2CH2OMe _ _ CF3} 6-650 isopropyl Me pyrazol-1-yl SO ₂ Me 6-651 isopropyl Me 4-methoxypyrazol-1-yl SO ₂ Me 6-652 isopropyl Me 1,2,3-triazol-1yl SO ₂ Me 6-653 isopropyl Me 1,2,3-triazole-2- silt SO ₂ Me 6-654 isopropyl Me C1 SO ₂ Me 6-655 isopropyl Me Me SO ₂ Me 6-656 isopropyl Me F Cl 6-657 isopropyl Me SO ₂ Me Cl 6-658 isopropyl Me NMe ₂ SO ₂ Me 6-659 isopropyl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-660 isopropyl _CF3 F _{SO2CH3 _} 6-661 isopropyl _CF3 SMe _{SO2CH3 _} 6-662 isopropyl _CF3 SEt _{SO2CH3 _} 6-663 isopropyl _CF3 S(O)Et _{SO2CH3 _} 6-664 isopropyl _{CF3 SO2CH3 _ SO2CH3 _} 6-665 isopropyl _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-666 isopropyl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-667 isopropyl _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-668 isopropyl SMe SMe F

- 74 040923

6-669 isopropyl SMe SEt F 6-670 isopropyl _{SO2CH3 _} F Cl 6-671 isopropyl F S(O)Me _CF3 6-672 isopropyl F SMe _CF3 6-673 CH ₂ CH ₂ OMe no ₂ H SO ₂ Me 6-674 CH ₂ CH ₂ OMe Cl H SO ₂ Me 6-675 CH ₂ CH ₂ OMe SO ₂ Me H _CF3 6-676 CH ₂ CH ₂ OMe NO ₂ H ome 6-677 CH ₂ CH ₂ OMe no ₂ H Br 6-678 CH ₂ CH ₂ OMe no ₂ H _CF3 6-679 CH ₂ CH ₂ OMe no ₂ H no ₂ 6-680 CH ₂ CH ₂ OMe no ₂ H Cl 6-681 CH ₂ CH ₂ OMe no ₂ H Me 6-682 CH ₂ CH ₂ OMe no ₂ H F 6-683 CH ₂ CH ₂ OMe ome H SO ₂ Me 6-684 CH ₂ CH ₂ OMe _CF3 H no ₂ 6-685 CH ₂ CH ₂ OMe CH ₂ SO ₂ Me H Br 6-686 CH ₂ CH ₂ OMe Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-687 CH ₂ CH ₂ OMe Cl ch ₂ och ₂ cf ₃ SMe 6-688 CH ₂ CH ₂ OMe Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-689 CH ₂ CH ₂ OMe Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-690 CH ₂ CH ₂ OMe Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-691 CH ₂ CH ₂ OMe Cl SMe Cl 6-692 CH ₂ CH ₂ OMe Cl SMe SO ₂ Me 6-693 CH ₂ CH ₂ OMe Cl Me SO ₂ Et 6-694 CH ₂ CH ₂ OMe Cl O (CH ₂ ) ₂ OMe Cl 6-695 CH ₂ CH ₂ OMe Cl OCH ₂ cyclopropyl Cl 6-696 CH ₂ CH ₂ OMe Cl OME Cl 6-697 CH ₂ CH ₂ OMe Cl NHAc Cl 6-698 CH ₂ CH ₂ OMe Cl OCH ₂ C(O)NMe ₂ Cl 6-699 CH ₂ CH ₂ OMe Cl Cl SO ₂ Me 6-700 CH ₂ CH ₂ OMe Cl pyrazol-1-yl SO ₂ Me 6-701 CH ₂ CH ₂ OMe Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-702 CH ₂ CH ₂ OMe Cl 1,2,3-triazole-1- silt SO ₂ Me 6-703 CH ₂ CH ₂ OMe Cl 1,2,3-triazole-2- silt SO ₂ Me 6-704 CH ₂ CH ₂ OMe Cl F SO ₂ Me 6-705 CH ₂ CH ₂ OMe Me SO ₂ Me SO ₂ Me 6-706 CH ₂ CH ₂ OMe Me SO ₂ Me _CF3

- 75 040923

6-707 CH ₂ CH ₂ OMe Me NMe ₂ SO ₂ Me 6-708 CH ₂ CH ₂ OMe Me S(O)Me _CF3 6-709 CH ₂ CH ₂ OMe Me SMe _CF3 6-710 CH ₂ CH ₂ OMe Me _{SO2CH2CH2OMe _ _ CF3} 6-711 CH ₂ CH ₂ OMe Me pyrazol-1-yl SO ₂ Me 6-712 CH ₂ CH ₂ OMe Me 4-methoxypyrazol-1-yl SO ₂ Me 6-713 CH ₂ CH ₂ OMe Me 1,2,3-triazol-1yl SO ₂ Me 6-714 CH ₂ CH ₂ OMe Me 1,2,3-triazole-2- silt SO ₂ Me 6-715 CH ₂ CH ₂ OMe Me C1 SO ₂ Me 6-716 CH ₂ CH ₂ OMe Me Me SO ₂ Me 6-717 CH ₂ CH ₂ OMe Me Me SMe 6-718 CH ₂ CH ₂ OMe Me SO ₂ Me Cl 6-719 CH ₂ CH ₂ OMe Me NMe ₂ SO ₂ Me 6-720 CH ₂ CH ₂ OMe Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-721 CH ₂ CH ₂ OMe _CF3 F _{SO2CH3 _} 6-722 CH ₂ CH ₂ OMe _CF3 SMe _{SO2CH3 _} 6-723 CH ₂ CH ₂ OMe _CF3 SEt _{SO2CH3 _} 6-724 CH ₂ CH ₂ OMe _CF3 S(O)Et _{SO2CH3 _} 6-725 CH ₂ CH ₂ OMe _{CF3 SO2CH3 _ SO2CH3 _} 6-726 CH ₂ CH ₂ OMe _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-727 CH ₂ CH ₂ OMe _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-728 CH ₂ CH ₂ OMe _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-729 CH ₂ CH ₂ OMe SMe SMe F 6-730 CH ₂ CH ₂ OMe SMe SEt F 6-731 CH ₂ CH ₂ OMe _{SO2CH3 _} F Cl 6-732 CH ₂ CH ₂ OMe F S(O)Me _CF3 6-733 CH ₂ CH ₂ OMe F SMe _CF3 6-734 CH ₂ CF ₃ no ₂ H SO ₂ Me 6-735 ch ₂ cf ₃ Cl H SO ₂ Me 6-736 ch ₂ cf ₃ SO ₂ Me H _CF3 6-737 ch ₂ cf ₃ no ₂ H ome 6-738 ch ₂ cf ₃ no ₂ H Br 6-739 ch ₂ cf ₃ no ₂ H _CF3 6-740 ch ₂ cf ₃ no ₂ H no ₂ 6-741 ch ₂ cf ₃ no ₂ H Cl 6-742 ch ₂ cf ₃ no ₂ H Me 6-743 ch ₂ cf ₃ no ₂ H F 6-744 ch ₂ cf ₃ ome H SO ₂ Me 6-745 ch ₂ cf _{3 CF3} H no ₂ 6-746 ch ₂ cf ₃ CH ₂ SO ₂ Me H Br 6-747 ch ₂ cf ₃ Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-748 ch ₂ cf ₃ Cl ch ₂ och ₂ cf ₃ SMe

- 76 040923

6-749 ch ₂ cf ₃ Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-750 ch ₂ cf ₃ Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-751 ch ₂ cf ₃ Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-752 ch ₂ cf ₃ Cl SMe Cl 6-753 ch ₂ cf ₃ Cl SMe SO ₂ Me 6-754 ch ₂ cf ₃ Cl Me SO ₂ Et 6-755 ch ₂ cf ₃ Cl O (CH ₂ ) ₂ OMe Cl 6-756 ch ₂ cf ₃ Cl OCH ₂ cyclopropyl Cl 6-757 ch ₂ cf ₃ Cl OME Cl 6-758 ch ₂ cf ₃ Cl NHAc Cl 6-759 ch ₂ cf ₃ Cl OCH ₂ C(O)NMe ₂ Cl 6-760 ch ₂ cf ₃ Cl Cl SO ₂ Me 6-761 ch ₂ cf ₃ Cl pyrazol-1-yl SO ₂ Me 6-762 ch ₂ cf ₃ Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-763 ch ₂ cf ₃ Cl 1,2,3-triazol-1yl SO ₂ Me 6-764 ch ₂ cf ₃ Cl 1,2,3-triazol-2yl SO ₂ Me 6-765 ch ₂ cf ₃ Cl F SO ₂ Me 6-766 ch ₂ cf ₃ Me SO ₂ Me SO ₂ Me 6-767 ch ₂ cf ₃ Me SO ₂ Me _CF3 6-768 ch ₂ cf ₃ Me NMe ₂ SO ₂ Me 6-769 ch ₂ cf ₃ Me S(O)Me _CF3 6-770 ch ₂ cf ₃ Me SMe _CF3 6-771 ch ₂ cf ₃ Me _{SO2CH2CH2OMe _ _ CF3} 6-772 ch ₂ cf ₃ Me pyrazol-1-yl SO ₂ Me 6-773 ch ₂ cf ₃ Me 4-methoxypyrazol-1-yl SO ₂ Me 6-774 ch ₂ cf ₃ Me 1,2,3-triazol-1yl SO ₂ Me 6-775 ch ₂ cf ₃ Me 1,2,3-triazole-2- silt SO ₂ Me 6-776 ch ₂ cf ₃ Me C1 SO ₂ Me 6-777 ch ₂ cf ₃ Me Me SO ₂ Me 6-778 ch ₂ cf ₃ Me Me SMe 6-779 ch ₂ cf ₃ Me SO ₂ Me Cl 6-780 ch ₂ cf ₃ Me NMe ₂ SO ₂ Me 6-781 ch ₂ cf ₃ Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-782 ch ₂ cf _{3 CF3} F _{SO2CH3 _} 6-783 ch ₂ cf _{3 CF3} SMe _{SO2CH3 _} 6-784 ch ₂ cf _{3 CF3} SEt _{SO2CH3 _}

- 77 040923

6-785 ch ₂ cf _{3 CF3} S(O)Et _{SO2CH3 _} 6-786 ch ₂ cf _{3 CF3 SO2CH3 _ SO2CH3 _} 6-787 ch ₂ cf _{3 CF3 OCH2CH2OMe _ SO2CH3 _} 6-788 ch ₂ cf _{3 CF3} OCH ₂ (CO)NMe ₂ SO2Me 6-789 ch ₂ cf _{3 CF3} CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-790 ch ₂ cf ₃ SMe SMe F 6-791 ch ₂ cf ₃ SMe SEt F 6-792 ch ₂ cf _{3 SO2CH3 _} F Cl 6-793 ch ₂ cf ₃ F S(O)Me _CF3 6-794 ch ₂ cf ₃ F SMe _CF3 6-795 tetrahydrofuran2-yl no ₂ H SO ₂ Me 6-796 tetrahydrofuran2-yl Cl H SO ₂ Me 6-797 tetrahydrofuran2-yl SO ₂ Me H _CF3 6-798 tetrahydrofuran2-yl no ₂ H ome 6-799 tetrahydrofuran2-yl no ₂ H Br 6-800 tetrahydrofuran2-yl no ₂ H _CF3 6-801 tetrahydrofuran2-yl no ₂ H no ₂ 6-802 tetrahydrofuran2-yl no ₂ H Cl 6-803 tetrahydrofuran2-yl no ₂ H Me 6-804 tetrahydrofuran2-yl no ₂ H F 6-805 tetrahydrofuran2-yl ome H SO ₂ Me 6-806 tetrahydrofuran2-yl _CF3 H no ₂

- 78 040923

6-807 tetrahydrofuran2-yl CH ₂ SO ₂ Me H Br 6-808 tetrahydrofuran2-yl Cl CH2OCH2CF3 SO ₂ Me 6-809 tetrahydrofuran2-yl Cl CH2OCH2CF3 SMe 6-810 tetrahydrofuran2-yl Cl 5-cyanomethyl4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-811 tetrahydrofuran2-yl Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-812 tetrahydrofuran2-yl Cl CH ₂ OCH ₂ tetrahydrofuran -2-yl SO ₂ Me 6-813 tetrahydrofuran2-yl Cl SMe Cl 6-814 tetrahydrofuran2-yl Cl SMe SO ₂ Me 6-815 tetrahydrofuran2-yl Cl Me SO ₂ Et 6-816 tetrahydrofuran2-yl Cl O (CH ₂ ) ₂ OMe Cl 6-817 tetrahydrofuran2-yl Cl OCH ₂ cyclopropyl Cl 6-818 tetrahydrofuran2-yl Cl OME Cl 6-819 tetrahydrofuran2-yl Cl NHAc Cl 6-820 tetrahydrofuran2-yl Cl OCH ₂ C(O)NMe ₂ Cl 6-821 tetrahydrofuran2-yl Cl Cl SO ₂ Me 6-822 tetrahydrofuran2-yl Cl pyrazol-1-yl SO ₂ Me

- 79 040923

6-823 tetrahydrofuran2-yl C1 4-methoxypyrazol-1-yl SO ₂ Me 6-824 tetrahydrofuran2-yl C1 1,2,3-triazol-1yl SO ₂ Me 6-825 tetrahydrofuran2-yl C1 1,2,3-triazole-2- silt SO ₂ Me 6-826 tetrahydrofuran2-yl C1 F SO ₂ Me 6-827 tetrahydrofuran2-yl Me SO ₂ Me SO ₂ Me 6-828 tetrahydrofuran2-yl Me SO ₂ Me _CF3 6-829 tetrahydrofuran2-yl Me NMe ₂ SO ₂ Me 6-830 tetrahydrofuran2-yl Me S(O)Me _CF3 6-831 tetrahydrofuran2-yl Me SMe _CF3 6-832 tetrahydrofuran2-yl Me _{SO2CH2CH2OMe _ _ CF3} 6-833 tetrahydrofuran2-yl Me pyrazol-1-yl SO ₂ Me 6-834 tetrahydrofuran2-yl Me 4-methoxypyrazol-1-yl SO ₂ Me 6-835 tetrahydrofuran2-yl Me 1,2,3-triazol-1yl SO ₂ Me 6-836 tetrahydrofuran2-yl Me 1,2,3-triazole-2- silt SO ₂ Me 6-837 tetrahydrofuran2-yl Me C1 SO ₂ Me 6-838 tetrahydrofuran2-yl Me Me SO ₂ Me

- 80 040923

6-839 tetrahydrofuran2-yl Me Me SMe 6-840 tetrahydrofuran2-yl Me SO ₂ Me Cl 6-841 tetrahydrofuran2-yl Me NMe ₂ SO ₂ Me 6-842 tetrahydrofuran2-yl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-843 tetrahydrofuran2-yl _CF3 F _{SO2CH3 _} 6-844 tetrahydrofuran2-yl _CF3 SMe _{SO2CH3 _} 6-845 tetrahydrofuran2-yl _CF3 SEt _{SO2CH3 _} 6-846 tetrahydrofuran2-yl _CF3 S(O)Et _{SO2CH3 _} 6-847 tetrahydrofuran2-yl _{CF3 SO2CH3 _ SO2CH3 _} 6-848 tetrahydrofuran2-yl _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-849 tetrahydrofuran2-yl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-850 tetrahydrofuran2-yl _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-851 tetrahydrofuran2-yl SMe SMe F 6-852 tetrahydrofuran2-yl SMe SEt F 6-853 tetrahydrofuran2-yl _{SO2CH3 _} F Cl 6-854 tetrahydrofuran2-yl F S(O)Me _CF3

- 81 040923

6-855 tetrahydrofuran2-yl F SMe _CF3 6-856 p-Rg no ₂ H SO ₂ Me 6-857 p-Rg Cl H SO ₂ Me 6-858 p-Rg SO ₂ Me H _CF3 6-859 p-Rg no ₂ H ome 6-860 p-Rg no ₂ H Br 6-861 p-Rg no ₂ H Cl 6-862 p-Rg no ₂ H _CF3 6-863 p-Rg no ₂ H no ₂ 6-864 p-Rg no ₂ H Me 6-865 p-Rg no ₂ H F 6-866 p-Rg ome H SO ₂ Me 6-867 p-Rg _CF3 H no ₂ 6-868 p-Rg CH ₂ SO ₂ Me H Br 6-869 p-Rg Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-870 p-Rg Cl ch ₂ och ₂ cf ₃ SMe 6-871 p-Rg Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-872 p-Rg Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-873 p-Rg Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-874 p-Rg Cl SMe Cl 6-875 p-Rg Cl SMe SO ₂ Me 6-876 p-Rg Cl Me SO ₂ Et 6-877 p-Rg Cl O (CH ₂ ) ₂ OMe Cl 6-878 p-Rg Cl OCH ₂ cyclopropyl Cl 6-879 p-Rg Cl OME Cl 6-880 p-Rg Cl NHAc Cl 6-881 p-Rg Cl OCH ₂ C(O)NMe ₂ Cl 6-882 p-Rg Cl Cl SO ₂ Me 6-883 p-Rg Cl pyrazol-1-yl SO ₂ Me 6-884 p-Rg Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-885 p-Rg Cl 1,2,3-triazol-1yl SO ₂ Me 6-886 p-Rg Cl 1,2,3-triazol-2yl SO ₂ Me 6-887 p-Rg Cl F SO ₂ Me 6-888 p-Rg Me SO ₂ Me SO ₂ Me 6-889 p-Rg Me SO ₂ Me _CF3 6-890 p-Rg Me NMe ₂ SO ₂ Me

- 82 040923

6-891 n-Pr Me S(O)Me _CF3 6-892 n-Pr Me SMe _CF3 6-893 n-Pr Me _{SO2CH2CH2OMe _ _ CF3} 6-894 n-Pr Me pyrazol-1-yl SO ₂ Me 6-895 n-Pr Me 4-methoxypyrazol-1-yl SO ₂ Me 6-896 n-Pr Me 1,2,3-triazol-1yl SO ₂ Me 6-897 n-Pr Me 1,2,3-triazol-2yl SO ₂ Me 6-898 n-Pr Me C1 SO ₂ Me 6-899 n-Pr Me Me SO ₂ Me 6-900 n-Pr Me Me SMe 6-901 n-Pr Me SO ₂ Me Cl 6-902 n-Pr Me NMe ₂ SO ₂ Me 6-903 n-Pr Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-904 n-Pr _CF3 F _{SO2CH3 _} 6-905 n-Pr _CF3 SMe _{SO2CH3 _} 6-906 n-Pr _CF3 SEt _{SO2CH3 _} 6-907 n-Pr _CF3 S(O)Et _{SO2CH3 _} 6-908 n-Pr _{CF3 SO2CH3 _ SO2CH3 _} 6-909 n-Pr _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-910 n-Pr _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-911 n-Pr _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-912 n-Pr SMe SMe F 6-913 n-Pr SMe SEt F 6-914 n-Pr _{SO2CH3 _} F Cl 6-915 n-Pr F S(O)Me _CF3 6-916 n-Pr F SMe _CF3 6-917 _CH2OEt NO ₂ H SO ₂ Me 6-918 _CH2OEt Cl H SO ₂ Me 6-919 _CH2OEt SO ₂ Me H _CF3 6-920 _CH2OEt no ₂ H ome 6-921 _CH2OEt no ₂ H Br 6-922 _CH2OEt no ₂ H _CF3 6-923 _CH2OEt no ₂ H no ₂ 6-924 _CH2OEt no ₂ H Cl 6-925 _CH2OEt no ₂ H Me 6-926 _CH2OEt no ₂ H F 6-927 _CH2OEt ome H SO ₂ Me 6-928 _{CH2OEt CF3} H no ₂ 6-929 _CH2OEt CH ₂ SO ₂ Me H Br 6-930 _CH2OEt Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-931 _CH2OEt Cl ch ₂ och ₂ cf ₃ SMe

- 83 040923

6-932 _CH2OEt Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-933 _CH2OEt Cl 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et 6-934 _CH2OEt Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-935 _CH2OEt Cl SMe Cl 6-936 _CH2OEt Cl SMe SO ₂ Me 6-937 _CH2OEt Cl Me SO ₂ Et 6-938 _CH2OEt Cl O (CH ₂ ) ₂ OMe Cl 6-939 _CH2OEt Cl OCH ₂ cyclopropyl Cl 6-940 _CH2OEt Cl OME Cl 6-941 _CH2OEt Cl NHAc Cl 6-942 _CH2OEt Cl OCH ₂ C(O)NMe ₂ Cl 6-943 _CH2OEt Cl Cl SO ₂ Me 6-944 _CH2OEt Cl pyrazol-1-yl SO ₂ Me 6-945 _CH2OEt Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-946 _CH2OEt Cl 1,2,3-triazol-1yl SO ₂ Me 6-947 _CH2OEt Cl 1,2,3-triazol-2yl SO ₂ Me 6-948 _CH2OEt Cl F SO ₂ Me 6-949 _CH2OEt Me SO ₂ Me SO ₂ Me 6-950 _CH2OEt Me SO ₂ Me _CF3 6-951 _CH2OEt Me NMe ₂ SO ₂ Me 6-952 _CH2OEt Me S(O)Me _CF3 6-953 _CH2OEt Me SMe _CF3 6-954 _CH2OEt Me _{SO2CH2CH2OMe _ _ CF3} 6-955 _CH2OEt Me pyrazol-1-yl SO ₂ Me 6-956 _CH2OEt Me 4-methoxypyrazol-1-yl SO ₂ Me 6-957 _CH2OEt Me 1,2,3-triazol-1yl SO ₂ Me 6-958 _CH2OEt Me 1,2,3-triazole-2- silt SO ₂ Me 6-959 _CH2OEt Me C1 SO ₂ Me 6-960 _CH2OEt Me Me SO ₂ Me 6-961 _CH2OEt Me Me SMe 6-962 _CH2OEt Me SO ₂ Me Cl 6-963 _CH2OEt Me NMe ₂ SO ₂ Me 6-964 _CH2OEt Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-965 _{CH2OEt CF3} F _{SO2CH3 _} 6-966 _{CH2OEt CF3} SMe _{SO2CH3 _} 6-967 _{CH2OEt CF3} SEt _{SO2CH3 _}

- 84 040923

6-968 _{CH2OEt CF3} S(O)Et _{SO2CH3 _} 6-969 _{CH2OEt CF3 SO2CH3 _ SO2CH3 _} 6-970 _{CH2OEt CF3 OCH2CH2OMe _ SO2CH3 _} 6-971 _{CH2OEt CF3} OCH ₂ (CO)NMe ₂ SO2Me 6-972 _{CH2OEt CF3} CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-973 _CH2OEt SMe SMe F 6-974 _CH2OEt SMe SEt F 6-975 _{CH2OEt SO2CH3 _} F Cl 6-976 _CH2OEt F S(O)Me _CF3 6-977 _CH2OEt F SMe _CF3 6-978 cyclobutyl no ₂ H SO ₂ Me 6-979 cyclobutyl Cl H SO ₂ Me 6-980 cyclobutyl SO ₂ Me H _CF3 6-981 cyclobutyl no ₂ H ome 6-982 cyclobutyl no ₂ H Br 6-983 cyclobutyl SMe H _CF3 6-984 cyclobutyl no ₂ H no ₂ 6-985 cyclobutyl no ₂ H Cl 6-986 cyclobutyl no ₂ H Me 6-987 cyclobutyl no ₂ H F 6-988 cyclobutyl ome H SO ₂ Me 6-989 cyclobutyl _CF3 H no ₂ 6-990 cyclobutyl CH ₂ SO ₂ Me H Br 6-991 cyclobutyl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-992 cyclobutyl Cl ch ₂ och ₂ cf ₃ SMe 6-993 cyclobutyl Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-994 cyclobutyl Cl 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et 6-995 cyclobutyl Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-996 cyclobutyl Cl SMe Cl 6-997 cyclobutyl Cl SMe SO ₂ Me 6-998 cyclobutyl Cl Me SO ₂ Et 6-999 cyclobutyl Cl O (CH ₂ ) ₂ OMe Cl 6-1000 cyclobutyl Cl OCH ₂ cyclopropyl Cl 6-1001 cyclobutyl Cl OME Cl 6-1002 cyclobutyl Cl NHAc Cl 6-1003 cyclobutyl Cl OCH ₂ C(O)NMe ₂ Cl 6-1004 cyclobutyl Cl Cl SO ₂ Me 6-1005 cyclobutyl Cl pyrazol-1-yl SO ₂ Me 6-1006 cyclobutyl Cl 4-methoxypyrazol-1-yl SO ₂ Me

- 85 040923

6-1007 cyclobutyl C1 1,2,3-triazole-1- IL SO ₂ Me 6-1008 cyclobutyl C1 1,2,3-triazol-2yl SO ₂ Me 6-1009 cyclobutyl C1 F SO ₂ Me 6-1010 cyclobutyl Me SO ₂ Me SO ₂ Me 6-1011 cyclobutyl Me SO ₂ Me _CF3 6-1012 cyclobutyl Me NMe ₂ SO ₂ Me 6-1013 cyclobutyl Me S(O)Me _CF3 6-1014 cyclobutyl Me SMe _CF3 6-1015 cyclobutyl Me _{SO2CH2CH2OMe _ _ CF3} 6-1016 cyclobutyl Me pyrazol-1-yl SO ₂ Me 6-1017 cyclobutyl Me 4-methoxypyrazol-1-yl SO ₂ Me 6-1018 cyclobutyl Me 1,2,3-triazol-1yl SO ₂ Me 6-1019 cyclobutyl Me 1,2,3-triazol-2yl SO ₂ Me 6-1020 cyclobutyl Me C1 SO ₂ Me 6-1021 cyclobutyl Me Me SO ₂ Me 6-1022 cyclobutyl Me Me SMe 6-1023 cyclobutyl Me SO ₂ Me Cl 6-1024 cyclobutyl Me NMe ₂ SO ₂ Me 6-1025 cyclobutyl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-1026 cyclobutyl _CF3 F _{SO2CH3 _} 6-1027 cyclobutyl _CF3 SMe _{SO2CH3 _} 6-1028 cyclobutyl _CF3 SEt _{SO2CH3 _} 6-1029 cyclobutyl _CF3 S(O)Et _{SO2CH3 _} 6-1030 cyclobutyl _{CF3 SO2CH3 _ SO2CH3 _} 6-1031 cyclobutyl _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-1032 cyclobutyl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-1033 cyclobutyl _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-1034 cyclobutyl SMe SMe F 6-1035 cyclobutyl SMe SEt F 6-1036 cyclobutyl _{SO2CH3 _} F Cl 6-1037 cyclobutyl F S(O)Me _CF3 6-1038 cyclobutyl F SMe _CF3 6-1039 cyclopentyl no ₂ H SO ₂ Me 6-1040 cyclopentyl Cl H SO ₂ Me 6-1041 cyclopentyl SO ₂ Me H _CF3 6-1042 cyclopentyl no ₂ H ome 6-1043 cyclopentyl no ₂ H Br 6-1044 cyclopentyl SMe H _CF3 6-1045 cyclopentyl no ₂ H no ₂ 6-1046 cyclopentyl no ₂ H Cl 6-1047 cyclopentyl no ₂ H Me

- 86 040923

6-1048 cyclopentyl no ₂ H F 6-1049 cyclopentyl OME H SO ₂ Me 6-1050 cyclopentyl _CF3 H no ₂ 6-1051 cyclopentyl CH ₂ SO ₂ Me H Br 6-1052 cyclopentyl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-1053 cyclopentyl Cl ch ₂ och ₂ cf ₃ SMe 6-1054 cyclopentyl Cl 5-cyanomethyl4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-1055 cyclopentyl Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-1056 cyclopentyl Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-1057 cyclopentyl Cl SMe Cl 6-1058 cyclopentyl Cl SMe SO ₂ Me 6-1059 cyclopentyl Cl Me SO ₂ Et 6-1060 cyclopentyl Cl O (CH ₂ ) ₂ OMe Cl 6-1061 cyclopentyl Cl OCH ₂ cyclopropyl Cl 6-1062 cyclopentyl Cl OME Cl 6-1063 cyclopentyl Cl NHAc Cl 6-1064 cyclopentyl Cl OCH ₂ C(O)NMe ₂ Cl 6-1065 cyclopentyl Cl Cl SO ₂ Me 6-1066 cyclopentyl Cl pyrazol-1-yl SO ₂ Me 6-1067 cyclopentyl Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-1068 cyclopentyl Cl 1,2,3-triazol-1yl SO ₂ Me 6-1069 cyclopentyl Cl 1,2,3-triazole-2- silt SO ₂ Me 6-1070 cyclopentyl Cl F SO ₂ Me 6-1071 cyclopentyl Me SO ₂ Me SO ₂ Me 6-1072 cyclopentyl Me SO ₂ Me _CF3 6-1073 cyclopentyl Me NMe ₂ SO ₂ Me 6-1074 cyclopentyl Me S(O)Me _CF3 6-1075 cyclopentyl Me SMe _CF3 6-1076 cyclopentyl Me _{SO2CH2CH2OMe _ _ CF3} 6-1077 cyclopentyl Me pyrazol-1-yl SO ₂ Me 6-1078 cyclopentyl Me 4-methoxypyrazol-1-yl SO ₂ Me 6-1079 cyclopentyl Me 1,2,3-triazol-1yl SO ₂ Me 6-1080 cyclopentyl Me 1,2,3-triazol-2yl SO ₂ Me 6-1081 cyclopentyl Me C1 SO ₂ Me 6-1082 cyclopentyl Me Me SO ₂ Me

- 87 040923

6-1083 cyclopentyl Me Me SMe 6-1084 cyclopentyl Me SO ₂ Me Cl 6-1085 cyclopentyl Me NMe ₂ SO ₂ Me 6-1086 cyclopentyl Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-1087 cyclopentyl _CF3 F _{SO2CH3 _} 6-1088 cyclopentyl _CF3 SMe _{SO2CH3 _} 6-1089 cyclopentyl _CF3 SEt _{SO2CH3 _} 6-1090 cyclopentyl _CF3 S(O)Et _{SO2CH3 _} 6-1091 cyclopentyl _{CF3 SO2CH3 _ SO2CH3 _} 6-1092 cyclopentyl _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-1093 cyclopentyl _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-1094 cyclopentyl _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-1095 cyclopentyl SMe SMe F 6-1096 cyclopentyl SMe SEt F 6-1097 cyclopentyl _{SO2CH3 _} F Cl 6-1098 cyclopentyl F S(O)Me _CF3 6-1099 cyclopentyl F SMe _CF3 6-1100 Me ₂ N no ₂ H SO ₂ Me 6-1101 Me ₂ N Cl H SO ₂ Me 6-1102 Me ₂ N SO ₂ Me H _CF3 6-1103 Me ₂ N no ₂ H ome 6-1104 Me ₂ N no ₂ H Br 6-1105 Me ₂ N no ₂ H _CF3 6-1106 Me ₂ N no ₂ H no ₂ 6-1107 Me ₂ N no ₂ H Cl 6-1108 Me ₂ N no ₂ H Me 6-1109 Me ₂ N no ₂ H F 6-1110 Me ₂ N ome H SO ₂ Me 6-1111 Me ₂ N _CF3 H no ₂ 6-1112 Me ₂ N CH ₂ SO ₂ Me H Br 6-1113 Me ₂ N Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-1114 Me ₂ N Cl ch ₂ och ₂ cf ₃ SMe 6-1115 Me ₂ N Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-1116 Me ₂ N Cl 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et 6-1117 Me ₂ N Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-1118 Me ₂ N Cl SMe Cl 6-1119 Me ₂ N Cl SMe SO ₂ Me 6-1120 Me ₂ N Cl Me SO ₂ Et 6-1121 Me ₂ N Cl O (CH ₂ ) ₂ OMe Cl 6-1122 Me ₂ N Cl OCH ₂ cyclopropyl Cl

- 88 040923

6-1123 Me ₂ N Cl ome Cl 6-1124 Me ₂ N Cl NHAc Cl 6-1125 Me ₂ N Cl OCH ₂ C(O)NMe ₂ Cl 6-1126 Me ₂ N Cl Cl SO ₂ Me 6-1127 Me ₂ N Cl pyrazol-1-yl SO ₂ Me 6-1128 Me ₂ N Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-1129 Me ₂ N Cl 1,2,3-triazol-1yl SO ₂ Me 6-1130 Me ₂ N Cl 1,2,3-triazole-2- silt SO ₂ Me 6-1131 Me ₂ N Cl F SO ₂ Me 6-1132 Me ₂ N Me SO ₂ Me SO ₂ Me 6-1133 Me ₂ N Me SO ₂ Me _CF3 6-1134 Me ₂ N Me NMe ₂ SO ₂ Me 6-1135 Me ₂ N Me S(O)Me _CF3 6-1136 Me ₂ N Me SMe _CF3 6-1137 Me ₂ N Me _{SO2CH2CH2OMe _ _ CF3} 6-1138 Me ₂ N Me pyrazol-1-yl SO ₂ Me 6-1139 Me ₂ N Me 4-methoxypyrazol-1-yl SO ₂ Me 6-1140 Me ₂ N Me 1,2,3-triazol-1yl SO ₂ Me 6-1141 Me ₂ N Me 1,2,3-triazole-2- silt SO ₂ Me 6-1142 Me ₂ N Me C1 SO ₂ Me 6-1143 Me ₂ N Me Me SO ₂ Me 6-1144 Me ₂ N Me Me SMe 6-1145 Me ₂ N Me SO ₂ Me Cl 6-1146 Me ₂ N Me NMe ₂ SO ₂ Me 6-1147 Me ₂ N Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-1148 Me ₂ N _CF3 F _{SO2CH3 _} 6-1149 Me ₂ N _CF3 SMe _{SO2CH3 _} 6-1150 Me ₂ N _CF3 SEt _{SO2CH3 _} 6-1151 Me ₂ N _CF3 S(O)Et _{SO2CH3 _} 6-1152 Me ₂ N _{CF3 SO2CH3 _ SO2CH3 _} 6-1153 Me ₂ N _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-1154 Me ₂ N _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-1155 Me ₂ N _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-1156 Me ₂ N SMe SMe F 6-1157 Me ₂ N SMe SEt F 6-1158 Me ₂ N _{SO2CH3 _} F Cl 6-1159 Me ₂ N F S(O)Me _CF3 6-1160 Me ₂ N F SMe _CF3 6-1161 Ph-NH no ₂ H SO ₂ Me 6-1162 Ph-NH Cl H SO ₂ Me

- 89 040923

6-1163 Ph-NH SO ₂ Me H _CF3 6-1164 Ph-NH no ₂ H ome 6-1165 Ph-NH no ₂ H Br 6-1166 Ph-NH no ₂ H _CF3 6-1167 Ph-NH no ₂ H no ₂ 6-1168 Ph-NH no ₂ H Cl 6-1169 Ph-NH no ₂ H Me 6-1170 Ph-NH no ₂ H F 6-1171 Ph-NH ome H SO ₂ Me 6-1172 Ph-NH _CF3 H no ₂ 6-1173 Ph-NH CH ₂ SO ₂ Me H Br 6-1174 Ph-NH Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-1175 Ph-NH Cl ch ₂ och ₂ cf ₃ SMe 6-1176 Ph-NH Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-1177 Ph-NH Cl 4,5-dihydro-1,2- oxazol-3-yl SO ₂ Et 6-1178 Ph-NH Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-1179 Ph-NH Cl SMe Cl 6-1180 Ph-NH Cl SMe SO ₂ Me 6-1181 Ph-NH Cl Me SO ₂ Et 6-1182 Ph-NH Cl O (CH ₂ ) ₂ OMe Cl 6-1183 Ph-NH Cl OCH ₂ cyclopropyl Cl 6-1184 Ph-NH Cl OME Cl 6-1185 Ph-NH Cl NHAc Cl 6-1186 Ph-NH Cl OCH ₂ C(O)NMe ₂ Cl 6-1187 Ph-NH Cl Cl SO ₂ Me 6-1188 Ph-NH Cl pyrazole-nil SO ₂ Me 6-1189 Ph-NH Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-1190 Ph-NH Cl 1,2,3-triazol-1yl SO ₂ Me 6-1191 Ph-NH Cl 1,2,3-triazole-2- silt SO ₂ Me 6-1192 Ph-NH Cl F SO ₂ Me 6-1193 Ph-NH Me SO ₂ Me SO ₂ Me 6-1194 Ph-NH Me SO ₂ Me _CF3 6-1195 Ph-NH Me NMe ₂ SO ₂ Me 6-1196 Ph-NH Me S(O)Me _CF3 6-1197 Ph-NH Me SMe _CF3 6-1198 Ph-NH Me _{SO2CH2CH2OMe _ _ CF3} 6-1199 Ph-NH Me pyrazol-1-yl SO ₂ Me

- 90 040923

6-1200 Ph-NH Me 4-methoxypyrazol-1-yl SO ₂ Me 6-1201 Ph-NH Me 1,2,3-triazol-1yl SO ₂ Me 6-1202 Ph-NH Me 1,2,3-triazol-2yl SO ₂ Me 6-1203 Ph-NH Me Cl SO ₂ Me 6-1204 Ph-NH Me Me SO ₂ Me 6-1205 Ph-NH Me Me SMe 6-1206 Ph-NH Me SO ₂ Me Cl 6-1207 Ph-NH Me NMe ₂ SO ₂ Me 6-1208 Ph-NH Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-1209 Ph-NH _CF3 F _{SO2CH3 _} 6-1210 Ph-NH _CF3 SMe _{SO2CH3 _} 6-1211 Ph-NH _CF3 SEt _{SO2CH3 _} 6-1212 Ph-NH _CF3 S(O)Et _{SO2CH3 _} 6-1213 Ph-NH _{CF3 SO2CH3 _ SO2CH3 _} 6-1214 Ph-NH _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-1215 Ph-NH _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-1216 Ph-NH _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-1217 Ph-NH SMe SMe F 6-1218 Ph-NH SMe SEt F 6-1219 Ph-NH _{SO2CH3 _} F Cl 6-1220 Ph-NH F S(O)Me _CF3 6-1221 Ph-NH F SMe _CF3 6-1222 morpholine-1- IL no ₂ H SO ₂ Me 6-1223 morpholin-1yl Cl H SO ₂ Me 6-1224 morpholin-1yl SO ₂ Me H _CF3 6-1225 morpholin-1yl no ₂ H ome 6-1226 morpholin-1yl no ₂ H Br 6-1227 morpholin-1yl no ₂ H _CF3 6-1228 morpholin-1yl no ₂ H no ₂ 6-1229 morpholin-1yl no ₂ H Cl 6-1230 morpholin-1yl no ₂ H Me 6-1231 morpholin-1yl no ₂ H F

- 91 040923

6-1232 morpholin-1yl OME H SO ₂ Me 6-1233 morpholin-1yl _CF3 H NO ₂ 6-1234 morpholin-1yl CH ₂ SO ₂ Me H Br 6-1235 morpholin-1yl Cl CH ₂ OCH ₂ CF ₃ SO ₂ Me 6-1236 morpholin-1yl Cl ch ₂ och ₂ cf ₃ SMe 6-1237 morpholin-1yl Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-1238 morpholin-1yl Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-1239 morpholin-1yl Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-1240 morpholin-1yl Cl SMe Cl 6-1241 morpholin-1yl Cl SMe SO ₂ Me 6-1242 morpholin-1yl Cl Me SO ₂ Et 6-1243 morpholin-1yl Cl O (CH ₂ ) ₂ OMe Cl 6-1244 morpholin-1yl Cl OCH ₂ cyclopropyl Cl 6-1245 morpholin-1yl Cl OME Cl 6-1246 morpholin-1yl Cl NHAc Cl 6-1247 morpholin-1yl Cl OCH ₂ C(O)NMe ₂ Cl 6-1248 morpholin-1yl Cl Cl SO ₂ Me 6-1249 morpholin-1yl Cl pyrazol-1-yl SO ₂ Me 6-1250 morpholin-1yl Cl 4-methoxypyrazol-1-yl SO ₂ Me 6-1251 morpholin-1yl Cl 1,2,3-triazol-1yl SO ₂ Me 6-1252 morpholin-1yl Cl 1,2,3-triazole-2- silt SO ₂ Me 6-1253 morpholin-1yl Cl F SO ₂ Me 6-1254 morpholin-1yl Me SO ₂ Me SO ₂ Me

- 92 040923

6-1255 morpholin-1yl Me SO ₂ Me _CF3 6-1256 morpholin-1yl Me NMe ₂ SO ₂ Me 6-1257 morpholin-1yl Me S(O)Me _CF3 6-1258 morpholine-1- silt Me SMe _CF3 6-1259 morpholin-1yl Me _{SO2CH2CH2OMe _ _ CF3} 6-1260 morpholin-1yl Me pyrazol-1-yl SO ₂ Me 6-1261 morpholine-1- silt Me 4-methoxypyrazol-1-yl SO ₂ Me 6-1262 morpholin-1yl Me 1,2,3-triazol-1yl SO ₂ Me 6-1263 morpholine-1- silt Me 1,2,3-triazole-2- silt SO ₂ Me 6-1264 morpholin-1yl Me C1 SO ₂ Me 6-1265 morpholin-1yl Me Me SO ₂ Me 6-1266 morpholin-1yl Me Me SMe 6-1267 morpholin-1yl Me SO ₂ Me Cl 6-1268 morpholin-1yl Me NMe ₂ SO ₂ Me 6-1269 morpholine-1- silt Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-1270 morpholin-1yl _CF3 F _{SO2CH3 _} 6-1271 morpholin-1yl _CF3 SMe _{SO2CH3 _} 6-1272 morpholine-1- silt _CF3 SEt _{SO2CH3 _} 6-1273 morpholine-1- silt _CF3 S(O)Et _{SO2CH3 _} 6-1274 morpholin-1yl _{CF3 SO2CH3 _ SO2CH3 _} 6-1275 morpholine-1- silt _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-1276 morpholine-1- silt _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-1277 morpholin-1yl _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et

- 93 040923

6-1278 morpholin-1yl SMe SMe F 6-1279 morpholin-1yl SMe SEt F 6-1280 morpholin-1yl SO2CH3 F C1 6-1281 morpholine-1- silt F S(O)Me _CF3 6-1282 morpholin-1yl F SMe _CF3 6-1283 sec-Bu NO ₂ H SO ₂ Me 6-1284 sec-Bu Cl H SO ₂ Me 6-1285 sec-Bu SO ₂ Me H _CF3 6-1286 sec-Bu NO ₂ H ome 6-1287 sec-Bu NO ₂ H Br 6-1288 sec-Bu NO ₂ H _CF3 6-1289 sec-Bu NO ₂ H NO ₂ 6-1290 sec-Bu NO ₂ H Cl 6-1291 sec-Bu NO ₂ H Me 6-1292 sec-Bu NO ₂ H F 6-1293 sec-Bu ome H SO ₂ Me 6-1294 sec-Bu _CF3 H NO ₂ 6-1295 sec-Bu CH2SO2 Me H Br 6-1296 sec-Bu Cl CH2OCH2CF3 SO ₂ Me 6-1297 sec-Bu Cl CH2OCH2CF3 SMe 6-1298 sec-Bu Cl 5-cyanomethyl- 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-1299 sec-Bu Cl 4,5-dihydro-1,2oxazol-3-yl SO ₂ Et 6-1300 sec-Bu Cl CH ₂ OCH ₂ -tetrahydrofuran-2-yl SO ₂ Me 6-1301 sec-Bu Cl SMe Cl 6-1302 sec-Bu Cl SMe SO ₂ Me 6-1303 sec-Bu Cl Me SO ₂ Et 6-1304 sec-Bu Cl O (CH ₂ ) ₂ OMe Cl 6-1305 sec-Bu Cl OCH ₂ cyclopropyl Cl 6-1306 sec-Bu Cl OME Cl 6-1307 sec-Bu Cl NHAc Cl 6-1308 sec-Bu Cl OCH ₂ C(O)NMe ₂ Cl 6-1309 sec-Bu Cl Cl SO ₂ Me 6-1310 sec-Bu Cl pyrazol-1-yl SO ₂ Me 6-1311 sec-Bu Cl 4-methoxypyrazol-1-yl SO ₂ Me

-94040923

6-1312 sec-Bu Cl 1,2,3-triazole-1- IL SO ₂ Me 6-1313 sec-Bu Cl 1,2,3-triazole-2- silt SO ₂ Me 6-1314 sec-Bu Cl F SO ₂ Me 6-1315 sec-Bu Me SO ₂ Me SO ₂ Me 6-1316 sec-Bu Me SO ₂ Me _CF3 6-1317 sec-Bu Me NMe ₂ SO ₂ Me 6-1318 sec-Bu Me S(O)Me _CF3 6-1319 sec-Bu Me SMe _CF3 6-1320 sec-Bu Me _{SO2CH2CH2OMe _ _ CF3} 6-1321 sec-Bu Me pyrazol-1-yl SO ₂ Me 6-1322 sec-Bu Me 4-methoxypyrazol-1-yl SO ₂ Me 6-1323 sec-Bu Me 1,2,3-triazol-1yl SO ₂ Me 6-1324 sec-Bu Me 1,2,3-triazole-2- silt SO ₂ Me 6-1325 sec-Bu Me C1 SO ₂ Me 6-1326 sec-Bu Me Me SO ₂ Me 6-1327 sec-Bu Me Me SMe 6-1328 sec-Bu Me SO ₂ Me Cl 6-1329 sec-Bu Me NMe ₂ SO ₂ Me 6-1330 sec-Bu Me NH(CH ₂ ) ₂ OMe SO ₂ Me 6-1331 sec-Bu _CF3 F _{SO2CH3 _} 6-1332 sec-Bu _CF3 SMe _{SO2CH3 _} 6-1333 sec-Bu _CF3 SEt _{SO2CH3 _} 6-1334 sec-Bu _CF3 S(O)Et _{SO2CH3 _} 6-1335 sec-Bu _{CF3 SO2CH3 _ SO2CH3 _} 6-1336 sec-Bu _{CF3 OCH2CH2OMe _ SO2CH3 _} 6-1337 sec-Bu _CF3 OCH ₂ (CO)NMe ₂ SO2Me 6-1338 sec-Bu _CF3 CH ₂ O-tetrahydrofuran-2-yl SO ₂ Et 6-1339 sec-Bu SMe SMe F 6-1340 sec-Bu SMe SEt F 6-1341 sec-Bu _{SO2CH3 _} F Cl 6-1342 sec-Bu F S(O)Me _CF3 6-1343 sec-Bu F SMe _CF3

- 95 040923

Table 7

Compounds of general formula (I) according to the invention, in which A is nitrogen, V is hydrogen, W is fluorine

No. R X z Physical data CH-nmr, dmsod _6.400 MHz) 7-1 H Cl _CF3 7-2 Me Cl _CF3 7-3 Et Cl _CF3 7-4 _CF3 Cl _CF3 7-5 CH ₂ OMe Cl _CF3 7-6 c-Pr Cl _CF3 7-7 _CO2et Cl _CF3 7-8 CO ₂ Me Cl _CF3 7-9 benzyl Cl _CF3 7-10 phenyl Cl _CF3 7-11 pyrazin-2-yl Cl _CF3 7-12 4-OMe-Ph Cl _CF3 7-13 4-Cl-Ph Cl _CF3 7-14 t-Bu Cl _CF3 7-15 furan-2-yl Cl _CF3 7-16 i-Pr Cl _CF3 7-17 CH ₂ CH ₂ OMe Cl _CF3 7-18 ch ₂ cf ₃ Cl _CF3 7-19 tetrahydrofuran-2-yl Cl _CF3 7-20 n-Pr Cl _CF3 7-21 _CH2OEt Cl _CF3 7-22 cyclobutyl Cl _CF3 7-23 cyclopentyl Cl _CF3 7-24 Me ₂ N Cl _CF3 7-25 Ph-NH Cl _CF3 7-26 morpholine-1-IL Cl _CF3 7-27 H Cl Cl 7-28 Me Cl Cl 7-29 Et Cl Cl 7-30 _CF3 Cl Cl 7-31 _CH2OMe Cl Cl 7-32 c-Pr Cl Cl 7-33 _CO2et Cl Cl 7-34 CO ₂ Me Cl Cl

- 96 040923

7-35 benzyl Cl Cl 7-36 phenyl Cl Cl 7-37 pyrazin-2-yl Cl Cl 7-38 4-OMe-Ph Cl Cl 7-39 4-Cl-Ph Cl Cl 7-40 t-Bu Cl Cl 7-41 furan-2-yl Cl Cl 7-42 i-Pr Cl Cl 7-43 CH ₂ CH ₂ OMe Cl Cl 7-44 CH ₂ CF ₃ Cl Cl 7-45 tetrahydrofuran-2-yl Cl Cl 7-46 n-Pr Cl Cl 7-47 _CH2OEt Cl Cl 7-48 cyclobutyl Cl Cl 7-49 cyclopentyl Cl Cl 7-50 Me ₂ N Cl Cl 7-51 Ph-NH Cl Cl 7-52 morpholine-1-NL Cl Cl 7-53 H Me Cl 7-54 Me Me Cl 7-55 Et Me Cl 7-56 _CF3 Me Cl 7-57 _CH2OMe Me Cl 7-58 c-Pr Me Cl 7-59 _CO2et Me Cl 7-60 CO ₂ Me Me Cl 7-61 benzyl Me Cl 7-62 phenyl Me Cl 7-63 pyrazin-2-yl Me Cl 7-64 4-OMe-Ph Me Cl 7-65 4-Cl-Ph Me Cl 7-66 t-Bu Me Cl 7-67 furan-2-yl Me Cl 7-68 i-Pr Me Cl 7-69 CH ₂ CH ₂ OMe Me Cl 7-70 CH ₂ CF ₃ Me Cl 7-71 tetrahydrofuran-2-yl Me Cl 7-72 n-Pr Me Cl 7-73 _CH2OEt Me Cl 7-74 cyclobutyl Me Cl 7-75 cyclopentyl Me Cl 7-76 Me ₂ N Me Cl 7-77 Ph-NH Me Cl

- 97 040923

7-78 morpholin-1-yl Me Cl 7-79 H Cl SMe 7-80 Me Cl SMe 7-81 Et Cl SMe 7-82 _CF3 Cl SMe 7-83 CH ₂ OMe Cl SMe 7-84 c-Pr Cl SMe 7-85 _CO2et Cl SMe 7-86 CO ₂ Me Cl SMe 7-87 benzyl Cl SMe 7-88 phenyl Cl SMe 7-89 pyrazin-2-yl Cl SMe 7-90 4-OMe-Ph Cl SMe 7-91 4-Cl-Ph Cl SMe 7-92 t-Bu Cl SMe 7-93 furan-2-yl Cl SMe 7-94 i-Pr Cl SMe 7-95 CH ₂ CH ₂ OMe Cl SMe 7-96 CH ₂ CF ₃ Cl SMe 7-97 tetrahydrofuran-2-yl Cl SMe 7-98 n-Pr Cl SMe 7-99 _CH2OEt Cl SMe 7-100 cyclobutyl Cl SMe 7-101 cyclopentyl Cl SMe 7-102 Me ₂ N Cl SMe 7-103 Ph-NH Cl SMe 7-104 morpholine-1-IL Cl SMe 7-105 H Cl SO ₂ Me 7-106 Me Cl SO ₂ Me 7-107 Et Cl SO ₂ Me 7-108 _CF3 Cl SO ₂ Me 7-109 _CH2OMe Cl SO ₂ Me 7-110 c-Pr Cl SO ₂ Me 7-111 _CO2et Cl SO ₂ Me 7-112 CO ₂ Me Cl SO ₂ Me 7-113 benzyl Cl SO ₂ Me 7-114 phenyl Cl SO ₂ Me 7-115 pyrazin-2-yl Cl SO ₂ Me 7-116 4-OMe-Ph Cl SO ₂ Me 7-117 4-Cl-Ph Cl SO ₂ Me 7-118 t-Bu Cl SO ₂ Me 7-119 furan-2-yl Cl SO ₂ Me 7-120 i-Pr Cl SO ₂ Me 7-121 CH ₂ CH ₂ OMe Cl SO ₂ Me

- 98 040923

7-122 ch ₂ cf ₃ Cl SO ₂ Me 7-123 tetrahydrofuran-2-yl Cl SO ₂ Me 7-124 n-Pr Cl SO ₂ Me 7-125 _CH2OEt Cl SO ₂ Me 7-126 cyclobutyl Cl SO ₂ Me 7-127 cyclopentyl Cl SO ₂ Me 7-128 Me ₂ N Cl SO ₂ Me 7-129 Ph-NH Cl SO ₂ Me 7-130 morpholin-1-yl Cl SO ₂ Me 7-131 Η Me _CF3 7-132 Me Me _CF3 7-133 Et Me _CF3 7-134 _CF3 Me _CF3 7-135 _CH2OMe Me _CF3 7-136 c-Pr Me _CF3 7-137 _CO2et Me _CF3 7-138 CO ₂ Me Me _CF3 7-139 benzyl Me _CF3 7-140 phenyl Me _CF3 7-141 pyrazin-2-yl Me _CF3 7-142 4-OMe-Ph Me _CF3 7-143 4-Cl-Ph Me _CF3 7-144 t-Bu Me _CF3 7-145 furan-2-yl Me _CF3 7-146 i-Pr Me _CF3 7-147 CH ₂ CH ₂ OMe Me _CF3 7-148 CH ₂ CF ₃ Me _CF3 7-149 tetrahydrofuran-2-yl Me _CF3 7-150 n-Pr Me _CF3 7-151 _CH2OEt Me _CF3 7-152 cyclobutyl Me _CF3 7-153 cyclopentyl Me _CF3 7-154 Me ₂ N Me _CF3 7-155 Ph-NH Me _CF3 7-156 morpholine-1-IL Me _CF3 7-157 H _{CH2OMe CF3} 7-158 Me _{CH2OMe CF3} 7-159 Et _{CH2OMe CF3} 7-160 _{CF3 CH2OMe CF3} 7-161 _{CH2OMe CH2OMe CF3} 7-162 c-Pr _{CH2OMe CF3} 7-163 _{CO2et CH2OMe CF3} 7-164 CO ₂ Me _{CH2OMe CF3}

- 99 040923

7-165 benzyl _{CH2OMe CF3} 7-166 phenyl _{CH2OMe CF3} 7-167 pyrazin-2-yl _{CH2OMe CF3} 7-168 4-OMe-Ph _{CH2OMe CF3} 7-169 4-Cl-Ph _{CH2OMe CF3} 7-170 t-Bu _{CH2OMe CF3} 7-171 furan-2-yl _{CH2OMe CF3} 7-172 i-Pr _{CH2OMe CF3} 7-173 CH ₂ CH ₂ OMe _{CH2OMe CF3} 7-174 CH ₂ CF _{3 CH2OMe CF3} 7-175 tetrahydrofuran-2-yl _{CH2OMe CF3} 7-176 n-Pr _{CH2OMe CF3} 7-177 _{CH2OEt CH2OMe CF3} 7-178 cyclobutyl _{CH2OMe CF3} 7-179 cyclopentyl _{CH2OMe CF3} 7-180 Me ₂ N _{CH2OMe CF3} 7-181 Ph-NH _{CH2OMe CF3} 7-182 morpholine-1-IL _{CH2OMe CF3} 7-183 H CH ₂ SMe _CF3 7-184 Me CH ₂ SMe _CF3 7-185 Et CH ₂ SMe _CF3 7-186 _CF3 CH ₂ SMe _CF3 7-187 _CH2OMe CH ₂ SMe _CF3 7-188 c-Pr CH ₂ SMe _CF3 7-189 _CO2et CH ₂ SMe _CF3 7-190 CO ₂ Me CH ₂ SMe _CF3 7-191 benzyl CH ₂ SMe _CF3 7-192 phenyl CH ₂ SMe _CF3 7-193 pyrazin-2-yl CH ₂ SMe _CF3 7-194 4-OMe-Ph CH ₂ SMe _CF3 7-195 4-Cl-Ph CH ₂ SMe _CF3 7-196 t-Bu CH ₂ SMe _CF3 7-197 furan-2-yl CH ₂ SMe _CF3 7-198 i-Pr CH ₂ SMe _CF3 7-199 CH ₂ CH ₂ OMe CH ₂ SMe _CF3 7-200 CH ₂ CF ₃ CH ₂ SMe _CF3 7-201 tetrahydrofuran-2-yl CH ₂ SMe _CF3 7-202 n-Pr CH ₂ SMe _CF3 7-203 _CH2OEt CH ₂ SMe _CF3 7-204 cyclobutyl CH ₂ SMe _CF3 7-205 cyclopentyl CH ₂ SMe _CF3 7-206 Me ₂ N CH ₂ SMe _CF3 7-207 Ph-NH CH ₂ SMe _CF3

- 100 040923

7-208 morpholin-1-yl CH ₂ SMe _CF3 7-209 H CH ₂ SO ₂ Me _CF3 7-210 Me CH ₂ SO ₂ Me _CF3 7-211 Et CH ₂ SO ₂ Me _CF3 7-212 _CF3 CH ₂ SO ₂ Me _CF3 7-213 CH ₂ OMe CH ₂ SO ₂ Me _CF3 7-214 c-Pr CH ₂ SO ₂ Me _CF3 7-215 _CO2et CH ₂ SO ₂ Me _CF3 7-216 CO ₂ Me CH ₂ SO ₂ Me _CF3 7-217 benzyl CH ₂ SO ₂ Me _CF3 7-218 phenyl CH ₂ SO ₂ Me _CF3 7-219 pyrazin-2-yl CH ₂ SO ₂ Me _CF3 7-220 4-OMe-Ph CH ₂ SO ₂ Me _CF3 7-221 4-Cl-Ph CH ₂ SO ₂ Me _CF3 7-222 t-Bu CH ₂ SO ₂ Me _CF3 7-223 furan-2-yl CH ₂ SO ₂ Me _CF3 7-224 i-Pr CH ₂ SO ₂ Me _CF3 7-225 CH ₂ CH ₂ OMe CH ₂ SO ₂ Me _CF3 7-226 CH ₂ CF ₃ CH ₂ SO ₂ Me _CF3 7-227 tetrahydrofuran-2-yl CH ₂ SO ₂ Me _CF3 7-228 n-Pr CH ₂ SO ₂ Me _CF3 7-229 _CH2OEt CH ₂ SO ₂ Me _CF3 7-230 cyclobutyl CH ₂ SO ₂ Me _CF3 7-231 cyclopentyl CH ₂ SO ₂ Me _CF3 7-232 Me ₂ N CH ₂ SO ₂ Me _CF3 7-233 Ph-NH CH ₂ SO ₂ Me _CF3 7-234 morpholine-1-IL CH ₂ SO ₂ Me _CF3 7-235 H _{CH2OC2H4OMe _ _ CF3} 7-236 Me _{CH2OC2H4OMe _ _ CF3} 7-237 Et _{CH2OC2H4OMe _ _ CF3} 7-238 _{CF3 CH2OC2H4OMe _ _ CF3} 7-239 _{CH2OMe CH2OC2H4OMe _ _ CF3} 7-240 c-Pr _{CH2OC2H4OMe _ _ CF3} 7-241 _{CO2et CH2OC2H4OMe _ _ CF3} 7-242 CO ₂ Me _{CH2OC2H4OMe _ _ CF3} 7-243 benzyl _{CH2OC2H4OMe _ _ CF3} 7-244 phenyl _{CH2OC2H4OMe _ _ CF3} 7-245 pyrazin-2-yl _{CH2OC2H4OMe _ _ CF3} 7-246 4-OMe-Ph _{CH2OC2H4OMe _ _ CF3} 7-247 4-Cl-Ph _{CH2OC2H4OMe _ _ CF3} 7-248 t-Bu _{CH2OC2H4OMe _ _ CF3} 7-249 furan-2-yl _{CH2OC2H4OMe _ _ CF3} 7-250 i-Pr _{CH2OC2H4OMe _ _ CF3} 7-251 CH ₂ CH ₂ OMe _{CH2OC2H4OMe _ _ CF3}

- 101 040923

7-252 ch ₂ cf _{3 CH2OC2H4OMe _ _ CF3} 7-253 tetrahydrofuran-2-yl _{CH2OC2H4OMe _ _ CF3} 7-254 n-Pr _{CH2OC2H4OMe _ _ CF3} 7-255 _{CH2OEt CH2OC2H4OMe _ _ CF3} 7-256 cyclobutyl _{CH2OC2H4OMe _ _ CF3} 7-257 cyclopentyl _{CH2OC2H4OMe _ _ CF3} 7-258 Me ₂ N _{CH2OC2H4OMe _ _ CF3} 7-259 Ph-NH _{CH2OC2H4OMe _ _ CF3} 7-260 morpholin-1-yl _{CH2OC2H4OMe _ _ CF3} 7-261 Η OCH ₂ -tetrahydrofuran-2-yl _CF3 7-262 Me OCH ₂ - tetrahydrofuran-2-yl _CF3 7-263 Et OCH ₂ - tetrahydrofuran-2-yl _CF3 7-264 _CF3 OCH ₂ - tetrahydrofuran-2-yl _CF3 7-265 _CH2OMe OCH ₂ - tetrahydrofuran-2-yl _CF3 7-266 c-Pr OCH ₂ - tetrahydrofuran-2-yl _CF3 7-267 _CO2et OCH ₂ - tetrahydrofuran-2-yl _CF3 7-268 CO ₂ Me OCH ₂ - tetrahydrofuran-2-yl _CF3 7-269 benzyl OCH ₂ - tetrahydrofuran-2-yl _CF3 7-270 phenyl OCH ₂ - tetrahydrofuran-2-yl _CF3 7-271 pyrazin-2-yl OCH ₂ - tetrahydrofuran-2-yl _CF3 7-272 4-OMe-Ph OCH ₂ - tetrahydrofuran-2-yl _CF3 7-273 4-Cl-Ph OCH ₂ - tetrahydrofuran-2-yl _CF3 7-274 t-Bu OCH ₂ - tetrahydrofuran-2-yl _CF3 7-275 furan-2-yl OCH ₂ - tetrahydrofuran-2-yl _CF3 7-276 i-Pr OCH ₂ - tetrahydrofuran-2-yl _CF3 7-277 CH ₂ CH ₂ OMe OCH ₂ - tetrahydrofuran-2-yl _CF3

- 102 040923

7-278 ch ₂ cf ₃ OCH ₂ - tetrahydrofuran-2-yl _CF3 7-279 tetrahydrofuran-2-yl OCH ₂ - tetrahydrofuran-2-yl _CF3 7-280 n-Pr OCH ₂ - tetrahydrofuran-2-yl _CF3 7-281 _CH2OEt OCH ₂ - tetrahydrofuran-2-yl _CF3 7-282 cyclobutyl OCH ₂ - tetrahydrofuran-2-yl _CF3 7-283 cyclopentyl OCH ₂ - tetrahydrofuran-2-yl _CF3 7-284 Me ₂ N OCH ₂ - tetrahydrofuran-2-yl _CF3 7-285 Ph-NH OCH ₂ - tetrahydrofuran-2-yl _CF3 7-286 morpholin-1-yl OCH ₂ - tetrahydrofuran-2-yl _CF3 7-287 Η (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-288 Me (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-289 Et (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-290 _CF3 (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-291 _CH2OMe (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-292 c-Pr (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-293 _CO2et (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-294 CO ₂ Me (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-295 benzyl (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3

- 103 040923

7-296 phenyl (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-297 pyrazin-2-yl (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-298 4-OMe-Ph (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-299 4-Cl-Ph (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-300 t-Bu (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-301 furan-2-yl (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-302 i-Pr (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-303 CH ₂ CH ₂ OMe (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-304 CH ₂ CF ₃ (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-305 tetrahydrofuran -2-yl (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-306 n-Pr (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-307 _CH2OEt (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-308 cyclobutyl (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-309 cyclopentyl (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-310 Me ₂ N (1,1-dioxido-1,2thiadiazolid in-1 yl)methyl _CF3

- 104 040923

7-311 Ph-NH (1,1-dioxido-1,2thiadiazolidin-1yl)methyl _CF3 7-312 morpholin-1-yl (1,1-dioxido-1,2thiadiazolidin-1 yl)methyl _CF3 7-313 Η (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-314 Me (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-315 Et (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-316 _CF3 (3-methyl-2- oxoimidazolidin-1 yl)methyl _CF3 7-317 _CH2OMe (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-318 c-Pr (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-319 _CO2et (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-320 CO ₂ Me (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-321 benzyl (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-322 phenyl (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-323 pyrazin-2-yl (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-324 4-OMe-Ph (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-325 4-Cl-Ph (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3

- 105 040923

7-326 t-Bu (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-327 furan-2-yl (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-328 i-Pr (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-329 CH ₂ CH ₂ OMe (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-330 CH ₂ CF ₃ (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-331 tetrahydrofuran-2-yl (3-methyl-2- oxoimidazolidin-1 yl)methyl _CF3 7-332 n-Pr (3-methyl-2oxoimidazolidin-1yl)methyl _CF3 7-333 _CH2OEt (3-methyl-2oxoimidazolidin-1yl)methyl _CF3 7-334 cyclobutyl (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-335 cyclopentyl (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-336 Me ₂ N (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-337 Ph-NH (3-methyl-2- oxoimidazolidin-1yl)methyl _CF3 7-338 morpholine-1-IL (3-methyl-2oxoimidazolidin-1yl)methyl _CF3 7-339 H (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3

- 106 040923

7-340 Me (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-341 Et (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-342 _CF3 (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-343 _CH2OMe (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-344 c-Pr (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-345 _CO2et (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-346 CO ₂ Me (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-347 benzyl (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-348 phenyl (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-349 pyrazin-2-yl (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-350 4-OMe-Ph (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3

- 107 040923

7-351 4-Cl-Ph (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-352 t-Bu (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-353 furan-2-yl (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-354 i-Pr (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-355 CH ₂ CH ₂ OMe (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-356 CH ₂ CF ₃ (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-357 tetrahydrofuran -2-yl (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-358 n-Pr (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-359 _CH2OEt (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-360 cyclobutyl (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-361 cyclopentyl (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-362 Me ₂ N (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-363 Ph-NH (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-364 morpholine-1-IL (3-methoxy-4-methyl-5oxo-4,5-dihydro-1H1,2,4-triazol-1yl)methyl _CF3 7-365 i-Pr C1 Me

- 108 040923

Table 8

Compounds according to the invention of general formula (I), in which

A is CY, Z is trifluoromethyl and R is methyl o H _γ

Ν—N Y\ \ Y // \\

Me^ _n ^N \\ x ° n

W\V

No. X Y V W Physical Data 8-1 C1 SOM H Cl 8-2 C1 SOM H Br 8-3 C1 SOM H CN 8-4 C1 SOM H no ₂ 8-5 C1 SOM H Me 8-6 C1 SOM H Et 8-7 C1 SOM H IPr 8-8 C1 SOM H cPr 8-9 C1 SOM H tBu 8-10 C1 SOM H _CF3 8-11 C1 SOM H _CHF2t 8-12 C1 SOM H c ₂ f ₅ 8-13 C1 SOM H _CH2OMe 8-14 C1 SOM H ome 8-15 C1 SOM H OEt 8-16 C1 SOM H OCF ₃ 8-17 C1 SOM H SMe 8-18 C1 SOM H SOM 8-19 C1 SOM H SO ₂ Me 8-20 C1 SOM Cl H 8-21 C1 SOM Br H 8-22 C1 SOM CN H 8-23 C1 SOM no ₂ H 8-24 C1 SOM Me H 8-25 C1 SOM Et H 8-26 C1 SOM IPr H 8-27 C1 SOM cPr H 8-28 C1 SOM tBu H 8-29 C1 SOM _CF3 H 8-30 C1 SOM _CHF2t H

- 109 040923

8-31 Cl SOM c ₂ f ₅ H 8-32 Cl SOM _CH2OMe H 8-33 Cl SOM ome H 8-34 Cl SOM OEt H 8-35 Cl SOM OCF ₃ H 8-36 Cl SOM SMe H 8-37 Cl SOM SOM H 8-38 Cl SOM SO ₂ Me H 8-39 Me SO ₂ Me H Cl 8-40 Me SO ₂ Me H Br 8-41 Me SO ₂ Me H CN 8-42 Me SO ₂ Me H no ₂ 8-43 Me SO ₂ Me H Me 8-44 Me SO ₂ Me H Et 8-45 Me SO ₂ Me H IPr 8-46 Me SO ₂ Me H cPr 8-47 Me SO ₂ Me H tBu 8-48 Me SO ₂ Me H _CF3 8-49 Me SO ₂ Me H _CHF2t 8-50 Me SO ₂ Me H c ₂ f ₅ 8-51 Me SO ₂ Me H _CH2OMe 8-52 Me SO ₂ Me H ome 8-53 Me SO ₂ Me H OEt

- 110 040923

8-54 Me SO ₂ Me H OCF ₃ 8-55 Me SO ₂ Me H SMe 8-56 Me SO ₂ Me H SOM 8-57 Me SO ₂ Me H SO ₂ Me 8-58 Me SO ₂ Me Cl H 8-59 Me SO ₂ Me Br H 8-60 Me SO ₂ Me CN H 8-61 Me SO ₂ Me no ₂ H 8-62 Me SO ₂ Me Me H 8-63 Me SO ₂ Me Et H 8-64 Me SO ₂ Me IPr H 8-65 Me SO ₂ Me cPr H 8-66 Me SO ₂ Me tBu H 8-67 Me SO ₂ Me _CF3 H 8-68 Me SO ₂ Me _CHF2t H 8-69 Me SO ₂ Me c ₂ f ₅ H 8-70 Me SO ₂ Me _CH2OMe H 8-71 Me SO ₂ Me ome H 8-72 Me SO ₂ Me OEt H 8-73 Me SO ₂ Me OCF ₃ H 8-74 Me SO ₂ Me SMe H 8-75 Me SO ₂ Me SOM H 8-76 g_ Me SO ₂ Me SO ₂ Me H

B. Formulation examples.

a) The dusting product is obtained by mixing 10 wt.h. compounds of formula (I) and/or salts thereof and 90 wt.h. talc as an inert substance, and grinding the mixture in a hammer mill.

b) Easily dispersible in water wettable powder is obtained by mixing 25 wt.h. compounds of formula (I) and/or salts thereof, 64 wt.h. kaolin-containing quartz as an inert substance, 10 wt.h. potassium lignosulfonate and 1 mass part of sodium oleoyl methyl taurate as wetting agent and dispersant, and grinding the mixture in a spin-disk mill.

c) Easily dispersible in water dispersion concentrate is obtained by mixing 20 wt.h. compounds of formula (I) and/or salts thereof with 6 wt.h. alkylphenolpolyglycol ether (®Triton X 207), 3 wt.h. isotridecanolpolyglycol ether (8 EO) and 71 wt.h. paraffinic mineral oil (boiling range, for example, from 255 to 277°C), and grinding the mixture in a ball mill to grind to a fineness of grinding less than 5 μm.

d) Emulsifiable concentrate is obtained from 15 wt.h. compounds of formula (I) and/or salts thereof, 75 wt.h. cyclohexanone as a solvent and 10 wt.h. ethoxylated nonylphenol as an emulsifier.

e) Water-dispersible granules are obtained by mixing wt.h. compounds of formula (I) and/or salts thereof, wt.h. calcium lignosulfonate, wt.h. sodium lauryl sulfate, wt.h. polyvinyl alcohol and wt.h. kaolin, grinding the mixture in a spin-disk mill, and granulating the powder in a fluidized bed by spraying water as the granulating liquid.

f) Water-dispersible granules are also obtained by homogenization and pre-grinding in a colloid mill

- 111 040923 wt.h. compounds of formula (I) and/or salts thereof, wt.h. 2,2'-dinaphthylmethane-6,6'-sodium disulfonate, parts by weight sodium oleoylmethyltaurate, parts by weight polyvinyl alcohol, wt.h. calcium carbonate and wt.h. water, then grinding the mixture in a ball mill and spraying and drying the resulting suspension in an irrigation column using a single-phase nozzle.

B. Biological examples.

1. Pre-emergence herbicidal action against harmful plants.

Seeds of monocot and dicot weeds and cultivated plants are planted in sandy soil in wood fiber pots and covered with soil. Then the compounds of the invention, prepared in the form of wettable powders (WP) or emulsion concentrates (EC), are applied to the surface of the covering soil in the form of an aqueous suspension or emulsion at a water application rate that is from 600 to 800 l/ha, with the addition of 0 .2% wetting agent. After treatment, the pots are placed in a greenhouse and kept under good conditions for the growth of the test plants. Damage to test plants is assessed visually after a 3-week test period compared to untreated controls (percent herbicidal activity (%): 100% activity=plants died, 0% activity=same as control plants).

In this test, for example, Compounds Nos. 2-242 and 2-243 at 320 g/ha each showed at least 80% efficacy against Echinochloa cms galli, Setaria viridis, Amaranthus retroflexus, Stellaria media, Veronica persica and Viola tricolor.

2. Post-emergence herbicidal action against harmful plants.

Seeds of monocot and dicotyledonous weeds and cultivated plants are planted in sandy soil in wood fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2-3 weeks after sowing, the test plants are treated at the single leaf stage. The compounds of the invention prepared as wettable powders (WP) or as emulsion concentrates (EC) are then sprayed on the green parts of plants in the form of an aqueous suspension or emulsion at a water application rate of 600-800 l/ha, with the addition of 0. 2% wetting agent. After the test plants are left in the greenhouse under optimal growth conditions for about 3 weeks, the effect of the preparations is assessed visually in comparison with untreated controls (percent herbicidal effect (%): 100% activity=plants died, 0% activity=as control plants).

In this test, for example, Compounds Nos. 2-242 and 2-243 at 80 g/ha each showed at least 80% efficacy against Echinochloa cms galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Stellaria media and Viola tricolor.

Claims (12)

1. N-(1,3,4-oxadiazol-2-yl)arylcarboxamide of formula (I) or salts thereof where the substituents have the following meanings: A is N or C-Y, R is hydrogen or (C1-C ₆ )alkyl, X is halogen or (C1-C ₆ )alkyl, Y is halogen, (C1-C ₆ )alkyl, S(O) _n R ² or 2-oxoazetidin-1-yl or C(O)N(R1) ₂ , Z is halogen, (C1-C ₆ )alkyl, S(O) _n R ² or halo(C1-C ₆ )alkyl, V is hydrogen, halogen or (C1-C ₆ )alkyl, W is hydrogen, halogen or (C1-C ₆ )haloalkyl, provided that in each case at least one of V and W is not hydrogen, i.e. that in the positions of the radicals V and W of the compound (I) only V or only W can represent hydrogen, R ¹ is hydrogen, (C1-C ₆ )alkyl, (C1-C ₆ )haloalkyl or (C ₃ -C ₆ )cycloalkyl(C1C ₆ )alkyl, R ² is (C1-C ₆ )alkyl, n is 0, 1 or 2, provided that the compounds 4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide, 4-bromo-2,6-difluoro-2-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)benzamide - 112 040923 excluded. 2. K-(1,3,4-oxadiazol-2-yl)arylcarboxamide according to claim 1, which is characterized in that A represents C-Y, V is hydrogen, W represents fluorine and the radicals R, X, Y and Z, as well as the radicals R'-R ² and n, each independently of the other, have the meanings indicated in π. 1. 3. Herbicidal composition, which is characterized in that it contains at least one compound of formula (I) according to claim 1 or 2 in a herbicidally active amount. 4. Herbicidal composition according to claim 3 in a mixture with auxiliary substances of the composition. 5. Herbicidal composition according to claim 3 or 4, which contains at least one additional pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators. 6. Herbicidal composition according to claim 5, which contains an antidote. 7. Herbicidal composition according to claim 6, which contains cyprosulfamide, cloquintocet-mexil, mefenpyr-diethyl or isoxadifen-ethyl. 8. Herbicidal composition according to any one of claims 3 to 7, which contains an additional herbicide. 9. A method for controlling unwanted plants, characterized in that an effective amount of at least one compound of formula (I) according to claim 1 or 2 or a herbicidal composition according to any one of claims 3 to 8 is applied to the plants or to the location of the unwanted vegetation . 10. The use of compounds of formula (I) according to claim 1 or 2 or herbicidal compositions according to any one of claims 3 to 8 to control unwanted plants. 11. Use according to claim 10, characterized in that the compounds of formula (I) are used to control unwanted plants in crops of useful plants. 12. The use according to claim 11, which is characterized in that the beneficial plants are transgenic beneficial plants.