UA62972C2 - Application of imidazopyrimidins and imidazopyridins for the treatment of neural disorders - Google Patents

Abstract

Corticotropin releasing factor (CRF) antagonists of formula (I) and their use in treating psychiatric disorders and neurological diseases, anxiety-related disorders, post-traumatic stress disorder, supranuclear palsy and feeding disorders as well as treatment of immunological, cardiovascular or heart-related diseases and colonic hypersensitivity associated with psychopathological disturbance and stress in mammals.

Description

The invention relates to new compounds, compositions and methods for the treatment of psychiatric disorders and neurological diseases, including general depression, disorders due to anxiety-depressive syndromes, post-traumatic stress disorders, disorders associated with supranuclear palsy and eating disorders, as well as for the treatment immunological, cardiovascular or heart diseases and colon hypersensitivity syndrome associated with psychopathological disorders and stress. In particular, the present invention relates to novel imidazopyrimidines and imidazopyridines, pharmaceutical compositions containing these compounds, and their use in the treatment of psychiatric disorders, neurological diseases, immunological, cardiovascular or heart diseases and colon hypersensitivity syndrome associated with psychopathological disorders and stress.

The factor that contributes to the release of adrenocorticotropic hormone (hereinafter referred to in the text as abbreviated as CAE), a 41 amino acid peptide, is the primary physiological regulator of the secretion of the peptide - a derivative of proopiomelanocortin (ROMS) from the anterior lobe of the pituitary gland (9. May Asad.

Zsi (OA) 80:4851 (1983); M/. Maiye ei ai., Zsivepse 213:1394 (1981)). In addition to the endocrine role in the pituitary gland, this hormone, as shown by the immunohistochemical localization of SAE, has a wide extra-hypothalamic distribution in the central nervous system and causes a wide range of autonomic, electrophysiological and behavioral effects, which corresponds to a neurotransmitter or neuromodulatory function in the brain (MU. Maie ei ai., Wes.

Nopt Vesv. 39:245 (1983); Sh. RE. Koob, Reg. Vepam Honey. 2; 39 (1985); E.V. de b5otsla eyi ai., U. Meshgozsi. 5:3189 (1985)). There is also evidence that SVAE plays an essential role in the integration of the immune system's response to physiological, psychological and immunological stressors (U.E. Viaiosk, Rpuzioiodisa! Nemiemuv 69:1 (1989); U.E. Mopieu, (Me Zsi. 41: 527 (1987)).

Evidence from clinical studies suggests that CA plays a role in psychiatric and neurological disorders, including depression, anxiety-depressive disorders, and eating disorders. The role of CAE is also postulated in the etiology and pathophysiology of the disease

Alzheimer's disease, Parkinson's disease, Huntington's disease, progressive supranuclear palsy and amyotrophic lateral sclerosis, since these diseases are associated with dysfunction of SAE neurons in the central nervous system (for a review, see E.V. de 5otsga, Nozr. Rgasiise 23:59 (1988 )|.

With an affective disorder or general depression, the concentration of SAE in the cerebrospinal fluid (C5E) of an individual who was not exposed to the action of drugs is significantly increased |S.V. Metageoiii ei ai., bsiepse 226:1342 (1984); SM. Vapki eyi ai., At. U. Rzuspiatsu 144:873 (1987); A.O. Egapse ei ai., VioI. Rzusniantu 28:86 (1988); M. Ahayu ei ai., Visi. Reuspianu 25:355 (1989)|). In addition, the density of SAE receptors in the frontal lobe of the cerebral cortex of suicide victims is significantly increased, which corresponds to the hypersecretion of SAE |S.V. Metegoi ei ai!., Agsp.

Sept. Rzuspianu 45:577 (1988)). In addition, there is a vague adrenocorticotropic (ASTH) reaction to SAE (which was administered intravenously), which was observed in patients in a depressed state (R.M. Soia ei ai., At. .).

Rzuspiaiu 141:619 (1984); R. Noizroeg and AI., Reuspopeigoepdosiipoiodu 9:147 (1984); R.MU. (019 eyi ai., Mem. Epa.

U. Mea. 314:1129 (1986)). Preclinical studies on rats and primates provided additional evidence in favor of the hypothesis that the hypersecretion of SVE plays a role in the symptoms observed in human depression | A.M. Zaraoi!: Ku, Agon. Sp. Reuspian 46:1047 (1989)). According to the preliminary data given in the work of Shgidogiadov and I., Meshgorzusporpaptasiodu 2:53 (1989), tricyclic antidepressants can change the levels of SVE and thus modulate the number of SVE receptors in the brain.

The role of SVAE was also postulated in the etiology of disorders caused by anxiety-depressive syndromes.

CAE causes anxiogenic effects in animals, and the interaction between benzodiazepine/non-benzodiazepine anxiolytics and CAE has been demonstrated in a number of models of anxiety-depressive behavior (O.V. Viyop eyi ai!., be 5si. 31:363 (1982); SM. Vepidde apa A.uU Yuipp Redii. Reriide5 16:83 (1986)). Previous experiments, conducted using a putative SVE receptor antagonist, α-helical sheep SVAE (9-41), on a number of behavioral examples demonstrated that this antagonist causes "anxiolytic-like" effects, which are qualitatively close to the action of benzodiazepines (S.M/ Vepidde apa A.Yu). Juipp Nogt. Vepam 21:393 (1987), Vgaip

Vezeagsi Nemiemuv 15:71 (1990)|.

All neurochemical and endocrine studies and experiments on receptor binding have shown that there is an interaction between SVE and benzodiazepine anxiolytics, and this is additional confirmation of the involvement of SAE in these disorders. Chlordiazepoxide weakens the "anxiogenic" effects of SAE as in the conflict test of ICT. Vgitsop eyi aI., Rrusporpaptasiodu 86:170 (1985); K.T. ViYtsop ei ai., Rheusporpagptatasoiodu 94:306 (1988), as well as in the test for fear caused by a sound stimulus (MA Zmegayum ei ai!., Reusporpagptatasoiodu 88:147 (1986)) conducted on rats. A benzodiazepine receptor antagonist (Ko 15-1788), which alone had no behavioral activity in the indicated conflict test, reduced the effects of SVE in a dose-dependent manner, whereas a benzodiazepine inverse agonist (bu 7142) enhanced the effects of SA ICT. Viyop ey ai.,

Rzusporpatptasiodu 94:306 (1988).

Additionally, CAE has been postulated to play a role in immunological, cardiovascular, or cardiac diseases such as hypertension, tachycardia and congestive heart failure, stroke, osteoporosis, preterm birth, psychosocial underdevelopment, stress-induced ascites, ulceration, diarrhea, postoperative ileus, and syndrome of increased sensitivity of the colon, associated with psychopathological disorders and stress.

The mechanisms and active sites through which standard anxiolytics and antidepressants exert their therapeutic effects remain to be elucidated. However, according to the proposed hypothesis, they take part in silencing the hypersecretion of SVE observed in the mentioned disorders. Of particular interest is the fact that previous studies on the effect of the CVE receptor antagonist (α-helical CAE 9-41) on a number of behavioral examples demonstrated that the CAE antagonist causes "anxiolytic-like" effects, which are qualitatively close to the action of benzodiazepines (for a review, see in S.G. Koob apa K.tT Viiyop, Ip: Sopisoigorip-NeiIeazipd Rasiog:

Vazis apa Siipisa! Zshshaieez oi a Meigoreriaye, E.V. where 5otsyga apa S.V. Metegoii edz., SAS Rhevzz r2gg21 (1990).

In the application of du Pont Merck PCT 0594/11050, a description of compounds - antagonists of the factor that promotes the release of adrenocorticotropic hormone, of the following formula is given:

Ki

Kai

KDl ex

Co and their use for the treatment of psychiatric disorders and neurological diseases. The description of this application includes fused pyridines and pyrimidines of the following formula:

Z id 2 A zbu ubem

But I, Her comfort is Arch

Where: M represents SV": or M; 2 is SV? or M; A is SVZO or M; and O is SV28 or M.

Other compounds that have activity as factors promoting the release of adrenocorticotropic hormone are disclosed in UUO 95/33750, MO 95/34563 and UMO 95/33727.

According to one of the aspects, the present invention introduces new compounds that bind to the receptors of the factor that promotes the release of adrenocorticotropic hormone, thereby reducing the anxiogenic effects of SAE secretions. The compounds of this invention are suitable for the treatment of psychiatric disorders and neurological diseases, disorders due to anxiety-depressive syndromes, post-traumatic stress disorders, disorders associated with supranuclear palsy, nutritional disorders, as well as for the treatment of immunological, cardiovascular or heart diseases and colon hypersensitivity syndrome associated with psychopathological disorders and stress in mammals.

According to another aspect, the present invention provides novel compounds of formula (I) (shown below) which are useful as antagonists of adrenocorticotropic hormone-releasing factor. The compounds of this invention show activity as antagonists of the factor that promotes the release of adrenocorticotropic hormone and apparently suppress the hypersecretion of SAB. The present invention also includes pharmaceutical compositions containing the specified compounds of formula (I) and methods of using such compounds to suppress CAE hypersecretion and/or to treat anxiogenic disorders.

According to another aspect, the present invention provides new compounds, pharmaceutical compositions and methods that can be used in the treatment of affective disorder, anxiety, depression, irritable bowel syndrome, post-traumatic stress disorder, supranuclear palsy, immunocompromised, Alzheimer's disease , gastrointestinal diseases, anorexia nervosa or other eating disorders, alcohol or drug withdrawal syndrome, drug addiction, inflammatory disorders, fertility-related problems and disorders that may be treated or alleviated by antagonism of CAE, including (but not limited to) disorders induced or maintained by CAE or a disorder selected from inflammatory disorders such as rheumatoid arthritis and osteoarthritis, pain, asthma, psoriasis and allergies; generalized anxiety-depressive state, panic, phobias, obsessive-compulsive disorder; disorders caused by post-traumatic stress; sleep disorders induced by stress; pain sensations, such as in fibromyalgia; mood disorders such as depression, including general depression, episodic depression, recurrent depression, childhood trauma-induced depression, and postpartum depression; dystemia; bipolar disorders; cyclothymia; fatigue syndrome; stress-induced headache; cancer; HIV infections (human immunodeficiency virus); neurodegenerative diseases such as Alzheimer's disease

Parkinson's and Huntington's disease; gastrointestinal diseases such as ulcers, irritable bowel syndrome, Crohn's disease, mucositis, diarrhea and postoperative ileus and colonic hypersensitivity syndrome associated with psychopathological disorders or stress; eating disorders such as anorexia nervosa or bulimia; hemorrhagic stress; stress-induced psychotic episodes; sick thyroid gland syndrome; syndrome of inappropriate antidiuretic hormone (AOH); adiposity; infertility; head injuries; spinal cord injuries; ischemic neuronal damage (for example, cerebral ischemia, such as cerebral hippocampal ischemia); excitotoxic neuronal damage; epilepsy; cardiovascular and cardiac disorders, including hypertension, tachycardia and congestive heart failure; blow; disorders of immune function, including stress-induced dysfunctions (e.g. stress-induced scrapie, porcine stress syndrome, bovine typhus, equine paroxysmal fibrillation and dysfunctions induced in chickens, shearing stress in sheep, or stress exposed to dogs when communicating with humans); muscle spasms; enuresis; senile dementia of Alzheimer's type; multi-infarct dementia; amyotrophic lateral sclerosis; dependence on chemical substances and addiction to them (for example, alcoholism, drug addiction, dependence on benzodiazepines or other drugs); drug or alcohol withdrawal syndromes; osteoporosis; psychosocial underdevelopment and hypoglycemia in mammals.

According to a further aspect of the present invention, the compounds provided by the present invention (Compounds of the present invention are particularly noted) are also useful as standards and reagents in determining the ability of a potential pharmaceutical drug to bind to the CVE receptor.

Thus, in the first variant, this invention introduces a new compound of formula I:

In ;

M. A. V

Not vi-k- | IN

M and 9 () or its stereoisomer or a pharmaceutically acceptable salt form, in which:

A is M or C-B7;

B is M or C-B8; provided that at least one of the groups A and B is M; p is an aryl or heteroaryl group attached through an unsaturated carbon atom;

X is selected from SN-VU, M-VE, O, 5(O)n and connection; n equals 0, 1 or 2;

B' is selected from C1-10 alkyl, C1-10 alkenyl, C2-10 alkynyl, C3-6 cycloazyl, C3-e cycloalkyl-C1-6 alkyl,

Ca alkoxy-Ci-4 alkyl, -502-Ci1-10 alkyl, -502-B"", and -502-B"E;

IN! is substituted with 0-1 substituents selected from -СМ, -5(О)п8и5, -СОВза, -СО28за, -МА'заСОвза, -

M(СО Ba)», -MAzaSOM A zad'vy, -MAzasoOvy, OMA zadiea, 1-morpholinyl, 1-piperidinyl, 1-piperazinyl, and

C3-C cycloalkyl, where 0-1 carbon atoms in Ca-C cycloalkyl are replaced by a group selected from -O-, -5(O)n-, -

МАЗа-, -МСОгВв-, -МСОВв- and -М5О2Во-, and where My in 1-piperazinyl is substituted 0-1 substituents selected from В!За, СО289, СОВИ and 50289;

IN! is also substituted with 0-3 substituents independently selected in each case from B'2, B", B/E, C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, Bg, C1, E, I, C -4 haloalkyl, -OB'Za, -"MD'Zad'va, C..4 alkoxy-C3-4 alkyl, and C3-C cycloalkyl, which is substituted 0-1 B? and in which 0-1 carbon atoms of Sv cycloalkyl are replaced by -O-; provided that B! is different from: (a) cyclohexyl - (CHg)" - group; (p) C-cyclopropyl-C-methoxypropyl group; (c) unsubstituted - (alkoxy)methyl group; and (a) 1-hydroxyalkyl group; also provided that when the B" alkyl is substituted by OH, the carbon atom adjacent to the M ring is different from

Sn";

B" represents aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each B" is substituted 0-1 -

ОВ" and 0-5 substituents chosen independently in each case from C1-e alkyl, C3-e cycloalkyl, Bg, SI,

E, I, C-4 haloalkyl, -SM, nitro, 5H, -5(O)p8!8, -SOV!", -OS(ОВ8, -"MAzaSOOV", -SHSOV", -"MA' asom A adcha, -MVizasSO2 BB, -MA17ad/iza, and -"SOMAadcha;

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, indazolyl, 2, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-B-oxide, 2,3-dihydrobenzothienyl-8-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted by 0 -4 carbon atoms by a substituent selected independently in each case from C1-in alkyl,

C3-ve cycloalkyl, Vg, SI, E, I, Si. haloalkyl, -СМ, nitro, -ОВ!", 5Н, -5(О)тВ!8, -"СОВ!", -ОС(О)В8, -"МазаСОВ!, -

М(СОВ2, -MAzaSOMAtad'za, -MAzasbO»ВвВВ, «MA tadza, and -SOMAard'za, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from В!za, СО2В!b , SOVII and 50281;

B!: represents a heterocyclyl and is a saturated or partially saturated heteroaryl, each heterocyclyl being a substituted 0-4 carbon atom substituent independently selected in each case from C1-C alkyl,

C3-e cycloalkyl, Bg, SI, E, I, C haloalkyl, -CM, nitro, -OVZa, 5H, -5(O)pv ie, -SOVIZa, -OC(O)B", -

MmA"asOov'za, "CO Ba)", -MAzasOMA zada, -MdzasoOgVyo, -MAZad'va, and -"SOMA zada, and each heterocyclyl is substituted on any nitrogen atom with 0-1 substituents selected from Ba . heteroaryl, or -(CH2)1-4-heterocycle, where the aryl, heteroaryl or heterocyclic group is substituted or unsubstituted;

IN? is selected from C1-6 alkyl, C3-6 cycloalkyl, C1-6 alkenyl, and C1-6 alkynyl and is substituted with 0-3 substituents selected from -CM, hydroxy, halo, and C 1 alkoxy; alternatively, B, in the case where X is a bond, is selected from -CM, CE3, and CoE5;

BZ, B" and BZ are selected independently in each case from H, Bg, SI, E, I, -CM, C-4 alkyl, C3-C cycloalkyl,

C1-6 alkoxy, C1-4 alkylthio, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, amino, C1-4 alkylamino, (C1-4 alkyl)2 amino and phenyl, each phenyl being substituted with 0-3 groups selected from C1- 7 alkyl, C3-C cycloalkyl, Bg, SI, E, I,

Cm haloalkyl, nitro, Cm alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, C1-4 alkylamino and (C1-4 alkyl)" amino; provided that when B! represents unsubstituted C1-10 alkyl, then BZ is different from substituted or unsubstituted phenyl;

BZ and BO are independently selected in each case from H, C-4 alkyl, C3-cycloalkyl-Cm alkyl and C3-6 cycloalkyl;

VZ is selected from H, Si. alkyl, C-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, C3-c cycloalkyl-

Seeds of alkyl, aryl, aryl (C-4 alkyl)-heteroaryl and heteroaryl (C-4 alkyl)-; za and D'ba are independently selected in each case from H, Ci-4 alkyl, Ci-4 haloalkyl, Ci-4 alkoxy-Ci-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-Ci-v alkyl;

B"" is selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 methoxy-C1-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-C1- in alkyl, aryl, aryl (C1-4 alkyl )-heteroaryl and heteroaryl (Sil alkyl)--a benzyl, each benzyl is substituted on the aryl component with 0-1 substituents selected from C.4 alkyl, Hg, C, E, I, C-4 haloalkyl, nitro, C -4h alkoxy, C-4 haloalkoxy, and dimethylamino;

Ba is selected from C-4 alkyl, C-4 haloalkyl, C-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-

Alkyl and benzyl, each benzyl is substituted on the aryl component with 0-1 substituents selected from

C-4 alkyl, Bg, C1, E, I, C4-haloalkyl, nitro, C4-alkoxy, C4-haloalkoxy, and dimethylamino;

B"5 is selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-

C-C alkyl;

IN? is independently selected in each case from H, C1-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl, and benzyl, each phenyl or benzyl being aryl-substituted 0-3 groups selected from C -4 alkyl, C1-4 alkyl, C1-4 haloalkyl, C1-4 haloalkyl, and dimethylamino; dza is independently selected in each case from H, C1-6 alkyl, C3-7 cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

IN! is chosen in each case from H, C1-6 alkyl, C30 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, C1-4 haloalkyl, B'5(O)p-C- 4 alkyl, and B"B10M-C".4 alkyl;

B!8 and BZ are selected independently in each case from H, C1-e alkyl, C3-o cycloalkyl, C3-e cycloalkyl-

C1-6 alkyl, C1-6 alkyl, C1-6 alkyl, and C1-6 haloalkyl; alternatively, in MA"B'? component B'" and BZ together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where M in 1-piperazinyl is a substituted 0-1 substituent selected from ВЗ, СО2В'"Е, SOV'!" and 502B!"; as an alternative, in MV'!7d' component B"? and BZ" together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where MA in 1-piperazinyl is substituted with 0-1 substituents selected from BZ, СО»2Б!Я, SOВ!: and 5028 ;

Ba and B/z are selected independently in each case from H, C1-e alkyl, C3-10 cycloalkyl, C3-e cycloalkyl-

Siv alkyl and C.4 haloalkyl; aryl is independently selected in each case from phenyl, naphthyl, indanyl and indenyl, each aryl being substituted with 0-5 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, methylenedioxy, C1-4 alkoxy-C1- 4 alkoxy, -"ОВ'", Vg, SI, E, I, C-4 haloalkyl, -SM, -MO",

ZN, -5(O)pV!8, -SOV!", -BO28!" -OS(O)B8, "MA ZSOV', -Щ(СОВ2, -"MA "SOM! Vya, -"MA!5SO2B!8, -MA!"B, and -SOMV' B": th to 1 fetsil , each phenyl substituent is substituted with 0-4 substituents selected from C1-C alkyl, C1-C alkoxy, Hg, C1, E, I, -CM, dimethylamino, C3, CoE5, OC3, 5O2Me, and acetyl; heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, triazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-8-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted on 0-4 carbon atoms a substituent selected independently in each case from C1-e alkyl, C3 cycloalkyl, Bg, SI, E, I,

Sm haloalkyl, -SM, nitro, -ОВ!", 5Н, -5(О)тВ!8, -СОВ!", -СО28!", -ОС(О)В'8, -МАСОВ"!, -ШСОВ '", -

MARSOMAVya, -MAZSO2 BB, -MA!VYA, and -SOMV" B", and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from Вё, СО2в't, СО and 5028Н!a ; and, provided that when O is imidazole or triazole, B' is other than unsubstituted C1-6 linear or branched alkyl, or C3-6 cycloalkyl. (LU variant, which is preferred, the present invention introduces a new compound of the formula Ia: y : 3

We We K dah dya

IN; (IB). (ha) In a more preferred embodiment, the present invention provides a novel compound of formula Ia, wherein:

X is selected from O, 5(O)n and a bond; n is equal to 0.1 or 2;

IN! is selected from C6 alkyl, C1-6 alkenyl, C6-6 alkynyl, and C3-6 cycloalkyl;

IN! is substituted by 0-1 substituents selected from -СМ, -5(О)пв75, -СОВ1за, -6028 732, and C3-in cycloalkyl, where 0-1 carbon atoms in Са cycloalkyl are replaced by a group selected from -О -, -5(О)п-, -МВ3а-, -МСО2ВЬ., -

MSOV'.- and -M5O»2Vo-;

IN! is also substituted with 0-2 substituents independently selected in each case from Ba, B"E, C 1 -C alkyl, C 8 alkenyl, C 8 -C alkynyl, BH, CI, E, CEz, CE2CEz, -OB1Za, -MVZadyba, C12 Alkoxy-C"? alkyl, and C3-C cycloalkyl, which is substituted 0-1 V? and in which 0-1 carbon atoms of Ca cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)»2 - group;

Ba is aryl and is selected from phenyl and indanyl, each H1 is substituted with 0-1 -OB" and 0-5 substituents independently selected in each case from C1-4 alkyl, C3-e cycloalkyl, B8, C1 , E, C-4 haloalkyl, -SM, -5(O)p818, -SOV1", -MVad'za, and -"SOMATadcha;

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from each in the case of C-4 alkyl, C3-e cycloalkyl, Bg, CI, E, SEz, -SM, -OB!", -5(O)tB!B, -SOV'", -MAad'zZa, and -SOMAad 'e, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from В'za, СО»

Owl and 5028; provided that B! is different from -(CHn):-4-aryl or -(CHn):-heteroaryl, wherein the aryl or heteroaryl group is substituted or unsubstituted;

IN? is selected from C1-1 alkyl, C1-1 alkenyl, and C1-1 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and Ci-4 alkoxy;

BZ and BZ are independently selected in each case from H, Bg, CI, E, -CM, Cm alkyl, C3-e cycloalkyl, C1-4 alkoxy, MH", Ci-" alkylamino, and (Ci-4" alkyl)" -amino;

IN? is selected independently in each case from H, C1-4 alkyl and C3-6 cycloalkyl;

BZ is selected from C-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl)-; z and D'ba are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B"" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-

Ci alkyl, aryl (Ci-2 alkyl)-, and heteroaryl (Ci-6 alkyl);

The fork is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-6 alkyl, and C3-6 cycloalkyl-C1-2 alkyl;

Vo is selected from C1-6 alkyl, C1-6 haloalkyl, C1-6 oxy-C1-alkyl, C3-6 cycloalkyl, and C3-6 cycloalkyl-C1-2 alkyl;

IN? is independently selected in each case from H, C1-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl and benzyl, each phenyl or benzyl being aryl-substituted 0-3 groups selected from C -4 alkyl, C8, C1, E, C1-4 haloalkyl, C1-4 haloalkyl, C1-4 haloalkoxy, and dimethylamino; dza is independently selected in each case from H, C1-6 alkyl, C3-7 cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B", B!8 and B!" is selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, and C1-6 haloalkyl; alternatively, in MB'"B"Z component B" and B'Z together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from from VZ, SO28!ya, SOV"" and 5028;

B" and B/za are independently selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C-4 alkyl, C3-e cycloalkyl, -OB"", Bg, CI, E, C-4 haloalkyl, -CM, -5( O)2B", -

Sov, -CO28!7, -MASOV!, -MAZSO2B'8, -MA!"VYA, and -SOMVA VU; and, the heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-oxide, 5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl, and benzodioxane, each heteroaryl is a 1-4 carbon atom substituted substituent selected independently in each case from C1-6 alkyl, C3-6 cycloalkyl, Bg , SI, E, Si-4 haloalkyl, -SM, -ОВ'", -5(0)tВ!8, -СОВ!", -СО28, -

ОС(ОВ!В, -МА"СОВ!", -ШЧСОВ! 2», -«МА"СО2В'В8, "МВА, and -СОМВ" В, and each heteroaryl is substituted on any nitrogen atom 0-1 by substituents selected from B", СО28/!la, СОВ"a and 50282, (25 In an even more preferred embodiment, the present invention introduces a new compound of the formula

Ia, where:

X is selected from O, 5 and a bond; B' is substituted C-C alkyl;

IN! is substituted by 0-1 substituents selected from -СМ, -СО2 132, and С3-в cycloalkyl, where 0-1 carbon atoms in Са-в cycloalkyl are replaced by a group selected from -О-, -5(О)п -, and -MV158-;

IN! is also substituted with 0-2 substituents independently selected in each case from Bhe, Bhe, C 6 alkyl, Cg-c alkenyl, Cc-c alkynyl, Bg, Si, E, SEZ, -OB'3a, -MVZad' Wow, S." alkoxy-Ci-2 alkyl, and C3-is cycloalkyl, which is substituted by 0-1 CH33 and in which 0-1 carbon atoms of Ca-in cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)" - group;

IN! is aryl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеСН",

ОоСссНн(СНЗз)г, OSНg.СНеоСНн;", and ОСЕ", and 0-3 substituents chosen independently in each case from СНЗ,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH" and -C(O)M(CH3)"2;

IN!" is heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH» СНз, СН(СНЗз)",

СНоСНоснН;», cyclopropyl, ОСсН3, ОСН».СН3, ОСН(СН3)г, ОСН.СНесСнН», ОС», Вг, СИ, Е, СЕз, -СМ, ЗСН3, -МН», -

Mne Hz, -M(CHz)", -C(O)MH", -C(O)MNOHz, and -C(O)M(CHz)2, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from СН3, СО2СН3, СОСН»3 and 5О2СН3; provided that B! is different from -(CH 2 r ) i -4-aryl or -(CH 2 r ) 1 i -4-heteroaryl, where the aryl or heteroaryl group is substituted or unsubstituted;

IN? selected from СН3, СНеСН3, СН(СН3)2, and СНЕСНоСН5;

ВЗ and ВЗ are chosen independently in each case from Н, СН3, СН2СН3, СН(СН33)г, and СНаСНоСН»; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CHvz,

SnesnH»z, CH(CHz)», СНСНоCH», cyclopropyl, OSHz, OSNoCH», OSH(CHZz)», OSH-CHnoCH», ОСЕ:;, VG, SI, E, SEz, -SM, 5СН3, 5О2СН3, -MHg, -MNOCH»z, -M(CHz)», -C(O)MH», -C(O)MNOVH», and -C(O)M(CHz)», and, the heteroaryl is selected independently in in each case from pyridyl, indolyl, benzothienyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-3-oxide, 2,3-dihydrobenzothienyl-b-dioxide, indolinyl, and benzoxazolin-2-one ilu, each heteroaryl is a substituent substituted by 2-4 carbon atoms, which is chosen independently in each case from CH3, СНеCH3, СН(CH3), СНаСНеаСН»3, cyclopropyl, ОСН3, ОСНегСН»,

Оосн(СнНз)», ОСН».СНосСнН», ОСЕз, Вг, СИ, ЕР, СЕз, -СМ, ЗСНз, 5О2СНз, -МНг, "МНОНз, -М(СНз)", -С(О)МН», -

С(О)МНеН", and -С(О)М(СНЗ3)", and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО»2СН3, СОСН» and 5О2СН». (2c| In an even more preferred embodiment, the present invention provides a new compound of formula Ia, wherein:

IN! is substituted by Si;

IN! is also substituted with 0-2 substituents chosen independently in each case from B! VE, SN,

СносСН3, СН(СН3)», СНаСНесСнН», -(СНг)зСН3, -СНАСН»:, -СНАСН(СН3), -СНАСН, -СНАС(СН3), -СНгОСсН», -

SnHsnNoOosnH;», P, CEz, cyclopropyl, CH3-cyclopropyl, cyclobutyl, CH3-cyclobutyl, cyclopentyl, CH3-cyclopentyl;

B!g is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеCH», and ОСЕ», and 0-2 substituents selected independently in each case from CH3, CH»CH3, CH(CH3)» СНгСНоСН;», Vg, SI, E,

SEz, -SM, and 5СН»Зз;

IN!" is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CHNaCH3, CH (СН3)г, СНаСНоСН», OSN»

ОоСНосСнН», ОС», Вг, СИ, Е, СЕз, -СМ, and ЗОН», and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО»2СН3, СОСН» and 5О2СН3 ; provided that B! is different from -(CH2)1-4-aryl or -(CH2):-"-heteroaryl, where the aryl or heteroaryl group is substituted or unsubstituted;

IN? is chosen from СН3, СНеСН», and СН(СН3)»;

VZ and VZ are chosen independently in each case from H and CHz; aryl is phenyl substituted with 2-4 substituents chosen independently in each case from CH3, СНеCH3, CH(CH3)», СННеоСнН5», cyclopropyl, ОСН3, ОСН»CH3, ОСН(СН3)2, ОСН.СНегсСнН» , OS», Vg, SI, E, SEz, -SM, 5СНz, 5О2СНz, -МН», -

Мне Нз,-М(СНз)».-С(О)МН», -С(О)МНС Нз, and-С(О)М(СНз)»; and, heteroaryl is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, CH»CH3, CH(CH33)»

SnHosSnHosCH», cyclopropyl, OSH3, OSH»CH3, OSH(CH3)», OSH»CHosCH:z, OS», Vg, SI, B..SEz, -SM, CH», 5O»CH3, -MH»g, -МНОН3, -М(СН3)», -С(О)МН», -С(О)МНС Na, and -С(О)М(СН3)». (24| In a further preferred embodiment, the present invention provides a novel compound of formula Ia wherein:

IN! is a substituted (cyclopropyl)-Ci alkyl or (cyclobutyl)-Ci alkyl; IN! is substituted 0-1 -CM;

IN! is also substituted with 0-1 substituents chosen independently in each case from

СноснНз, СснН(Снз)», СНСНесСнН», -(СНг)зСНзи, -СНАСН»:, -СНАСН(СНзи), - СН-СН, -СНАС(СНЗ3), -СНгОСсН with, -

СНННООосСНн;», E, SE3, cyclopropyl, and CH3-cyclopropyl;

IN! is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеCH", and ОСЕ", and 0-2 substituents selected independently in each case from CH3, CH»CH3, CH(CH3)", CHgCHNoCH;" , Vg, SI, E,

SEz, -SM, and 5СН»Зз;

IN!" is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, and pyrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH2CH3, CH(CH3)" , SNESNoSN", OSNz, OSNoSN", OSE", Vg,

SI, E, SEz, -SM, and SN". (2e| In another, even more preferred embodiment, the present invention provides a novel compound of formula Ia, wherein:

IN! is (cyclopropyl)-Ci alkyl or (cyclobutyl)-Ci alkyl, substituted by 1 substituent, which is selected independently in each case from B, B!E, CH3, CH»CH3, CH(CH3)», СНаСНеСН», -( CHg)zCH", - сн-сСно, -СНАСН(CH3), -CH-CH, -CH-С(CH3), -CHГОсСНИ, -СНа.CHГОосCH», PE, СЕз, cyclopropyl, and CH3- cyclopropyl;

B!g is phenyl substituted with 0-2 substituents chosen independently in each case from SNZz,

SNeoSN", SI, E, and SEz;

IN!" is a heteroaryl selected from furanyl, thienyl, and isoxazolyl, each heteroaryl being a 0-2 carbon substituted substituent independently selected in each case from CH33,

OSN;", SI, E, and SEz.

In an even more preferred embodiment, the present invention provides a novel compound of formula Ia, wherein:

B' is selected from the group (cyclopropyl) CH-CH3, (cyclopropyl)y CH-CHNeCH»3, (cyclopropyl CH-CHhOCH), (cyclopropyl CH-CHNa.CHosCH), (cyclopropyl CH-CHNa.CHhOsnH), (cyclopropyl) 2CH, phenyl(cyclopropyl)CH, furanyl(icyclopropyl)CH, thienyl(icyclopropyl)CH, isoxazolyl(icyclopropyl)CH, (CH3-furanyl) (cyclopropyl)CH, (cyclobutyl)CH-CH3, (cyclobutyl)CH-CHnoCH3, (cyclobutyl/uCH-CHgOSsCH", (cyclobutyl)usH-CHNa.CHgCHvz, (cyclobutylus H-CHNaCHgOsnH 5, (cyclobutyl2 CH, phenyl(cyclobutyl) CH, furanyl(cyclobutyl) CH, thienyl(icyclobutyl) CH, isoxazolyl(icyclobutyl) CH, and (CH3-furanyl)(cyclobutyl)CH.(29) In another, even more preferred embodiment, the present invention provides a novel compound of formula Ia wherein:

O is phenyl substituted with 2-4 substituents chosen independently in each case from SNZ3,

СнесСнН»з, СН(СНз)», СНаСНесНС», cyclopropyl, OSН3, OSН»СН3, OSН(СН3)г2, OSНаСНоснН», ОСЕ:», Ви, СИ, Е, and

SEZ (21 In another and even more preferred embodiment, the present invention provides a novel compound of formula Ia wherein:

O is a pyridyl substituted on 2-4 carbon atoms by a substituent chosen independently in each case from CH3, СНеCH3, CH(CH3)», CH»СНаCH3, cyclopropyl, OSН, OSНоCH3, OSН(СН33)».

OoSsnN.SNgsN;", OSEZ, VI, SI, E, and SEz. (2i| In another preferred embodiment, the present invention provides a new compound of formula Ia, wherein said compound is selected from the group: 3-(1-cyclopropylpropyl)-7-(2,4-dichlorophenyl)-2-ethyl-ZH- imidazo|4,5-5| pyridine; 3-(1-cyclopropylpropyl)-7-(2,4-dichlorophenyl)-2-methoxy-ZN-imidazoi|4,5-BI| pyridine; 3-(1-cyclopropylpropyl) )-7-(2,4-dichlorophenyl)-2-(methylsulfanyl)-ZH-imidazoi|4,5-BI pyridine; 7-(d-chloro-4--trifluoromethyl)phenyl|-3-(1-cyclopropylpropyl )-2-ethyl-ZN-imidazo(4,5-BI| pyridine;

7-(d-chloro-4-trifluoromethyl)phenyl|-3-(1-cyclopropylpropyl)-2-methoxy-ZN-imidazo(4,5-BI| pyridine; 7-(d-chloro-4--trifluoromethyl) )phenyl|-3-(1-cyclopropylpropyl)-2-(methylsulfanyl)-ZH-imidazoi|4,5-B pyridine; 3-(1-cyclopropylpropyl)-2-ethyl-7-I(2-methyl-4 --trifluoromethyl)phenyl|-ZN-imidazoi(4,5-BI| pyridine; 7-(2-chloro-4-methoxyphenyl)-3-(1-cyclopropylpropyl)-2-ethyl-ZN-imidazoi|4,5 -BI| pyridine; 7-(2-chloro-4-methoxyphenyl)-3-(1-cyclopropylpropyl)-2-methoxy-ZN-imidazo(|4,5-5|-pyridine; 3-(1-cyclopropylpropyl) -2-ethyl-7-(4-methoxy-2,5-dimethylphenyl)-ZH-imidazoi(4,5-BI| pyridine; 3-(1-cyclopropylpropyl)-2-methoxy-7-(4-methoxy- 2,5-dimethylphenoxy)-ZN-imidazoi|4,5-B| pyridine; 7-(2-chloro-4-methoxyphenyl)-3-(1-cyclopropylpropyl)-2-ethyl-ZN-imidazoi|4,5 -BI| pyridine; 7-(2-chloro-4-methoxyphenyl)-3-(1-cyclopropylpropyl)-2-methoxy-ZN-imidazoi(4,5-BI| pyridine; 7-(2-chloro-5- fluoro-4-methoxyphenyl)-3-(1-cyclopropylpropyl)-2-ethyl-ZN-imidazo(|4,5-BI| pyridine; 7-(2-chloro-fluoro-4-methoxyphenyl)-3-(1 -cyclopropylpropyl)-2-methoxy-ZN- imidazoi|4,5-B| pyridine; 7-(2-chloro-5-fluoro-4-methylphenyl)-3-(1-diclopropylpropyl)-2-ethyl-ZN-imidazoi|4,5-B| pyridine; 7-(2-chloro-fluoro-4-methylphenyl)-3-(1-cyclopropylpropyl)-2-methoxy-H-imidazoi|4,5-BI| pyridine; 3-(1-cyclopropylpropyl)-2-ethyl-7-(2,4,5-trimethylphenyl)-ZH-imidazoi|4,5-BI| pyridine; 3-(1-cyclopropylpropyl)-2-methoxy-7-(2,4,5-trimethylphenyl)-ZH-imidazoi|4,5-BI| pyridine; 3-(1-cyclopropylpropyl)-2-ethyl-7-(2,5,6-trimethyl-3-pyridinyl)-ZH-imidazoi(4,5-BI| pyridine; 3-(1-cyclopropylpropyl)-2- methoxy-7-(2,5,6-trimethyl-Z-pyridinyl)-ZH-imidazo(4,5-B| pyridine; 3-(1-cyclopropylpropyl)-7-(2,6-dimethyl-Z-pyridinyl )-2-ethyl-ZN-imidazoi|4,5-B| pyridine; 3-(1-cyclopropylpropyl)-7-(2,6-dimethyl-3-pyridinyl)-2-methoxy-ZN-imidazoi(4, 5-BI pyridine; 3-(1-cyclopropylpropyl)-7-(2,6-dimethoxy-3-pyridinyl)-2-ethyl-ZN-imidazoi|4,5-BI| pyridine; 7-(2,4- dichlorophenyl)-2-ethyl-3-(1-ethylpropyl)-ZH-imidazo(|4,5-BI| pyridine; 7-(2,4-dichlorophenyl)-3-(1-ethylpropyl)-2-methoxy- ZH-imidazoi|4,5-B|pyridine; 7-(d-chloro-4--trifluoromethyl)phenyl|-2-ethyl-3-(1-ethylpropyl)-ZH-imidazo(|4,5-BI| pyridine; 7-(d-chloro-4-trifluoromethyl)phenyl|-3-(1-ethylpropyl)-2-methoxy-ZN-imidazoi(4,5-BI| pyridine; 7-(d-chloro-4- (methylsulfonyl)phenyl|-2-ethyl-3-(1-ethylpropyl)-ZH-imidazoi|4,5-BI pyridine; 7-(d-chloro-4-(methylsulfonyl)phenyl|-3-(1-ethylpropyl) )-2-methoxy-ZN-imidazoi|4,5-BI| pyridine; 2-ethyl-3-(1-ethylpropyl)-7-(4-methoxy-2,5- dimethylphenyl)-ZH-imidazo(|4,5-BI| pyridine; 3-(1-ethylpropyl)-2-methoxy-7-(4-methoxy-2,5-dimethylphenyl)-ZH-imidazoi|4,5-B| pyridine; 7-(2-chloro-4-methoxyphenyl)-2-ethyl-3-(1-ethylpropyl)-ZN-imidazo|4,5-BI| pyridine; 7-(2-chloro-4-methoxyphenyl)-3-(1-ethylpropyl)-2-methoxy-ZN-imidazo(4,5-BI| pyridine; 2-ethyl-3-(1-ethylpropyl)-7- |I4-methoxy-2-"trifluoromethyl)phenyl|-ZH-imidazoi|4,5-BI pyridine; 3-(1-ethylpropyl)-2-methoxy-7-(4-methoxy-2-trifluoromethyl)phenyl|-ZH-imidazoi|4,5-BI| pyridine; 7-(2,6-dimethoxy-Z-pyridinyl)-2-ethyl-3-(1-ethylpropyl)-ZH-imidazo(|4,5-BI| pyridine; 7-(2,6-dimethyl-Z3- pyridinyl)-2-ethyl-3-(1-ethylpropyl)-ZH-imidazoi|4,5-B| pyridine; 2-ethyl-3-(1-ethylpropyl)-7-(2,5,6-trimethyl- 3-pyridinyl)-ZN-imidazo(4,5-BI| pyridine; 2-ethyl-3-(1-ethylpropyl)-7-(5-fluoro-4-methoxy-2-methylphenyl)-ZN-imidazoi|4 ,5-BI| pyridine; 3-(1-ethylpropyl)-7-(5-fluoro-4-methoxy-2-methylphenyl)-2-methoxy-ZN-imidazoi|4,5-BI| pyridine;

3-chloro-4-(2-ethyl-3-(1-ethylpropyl)-ZN-imidazoi(4,5-0I|pyridin-7-yl|benzonitrile;

3-Chloro-4-I3-(1-ethylpropyl)-2-methoxy-ZH-imidazoi(4,5-OI pyridin-7-yl|benzonitrile; 1-(3-chloro-4-(2-ethyl-3 -(1-ethylpropyl)-ZN-imidazo(4,5-b|pyridin-7-yl|phenyl)y -1-ethanol; 1-(3-chloro-4-I3-(1-ethylpropyl)-2- methoxy-ZN-imidazo(4,5-b|pyridin-7-ylIfenyl)-1-ethanol;

C-(dicyclopropylmethyl)-2-ethyl-7-(5-fluoro-4-methoxy-2-methylphenyl)-ZH-imidazo(|4,5-b|pyridine;

3-(dicyclopropylmethyl)-7-(5-fluoro-4-methoxy-2-methylphenyl)-2-methoxy-3H-imidazo(4,5-p|pyridine; 7-(2-chloro-4-methoxyphenyl)- 3-(dicyclopropylmethyl)-2-ethyl-ZN-imidazo(|4,5-b|pyridine; 7-(2-chloro-4-methoxyphenyl)-3-(dicyclopropylmethyl)-2-methoxy-ZN-imidazo(| 4,5-b|pyridine; 7-(2,4-dichlorophenyl)-3-(dicyclopropylmethyl)-2-ethyl-ZH-imidazo(|4,5-b|pyridine; 7-(2,4-dichlorophenyl) -3-(dicyclopropylmethyl)-2-methoxy-ZN-imidazo(4,5-b|pyridine; 7-(d-chloro-4--trifluoromethyl)phenyl|-3-(dicyclopropylmethyl)-2-ethyl-ZN- imidazo|4,5-|pyridine; 7-(d-chloro-4--trifluoromethyl)phenyl|-3-(dicyclopropylmethyl)-2-methoxy-ZN-imidazo(4,5-b|pyridine; 7-(2 ,4-dichlorophenyl)-2-ethyl-3-(1-ethyl-3-methoxypropyl)-ZH-imidazo|4,5-b|pyridine; 7-(2,4-dichlorophenyl)-3-(1-ethyl -3-methoxypropyl)-2-methoxy-ZN-imidazo|4,5-p|pyridine; 21 7-(d-chloro-4--trifluoromethyl)phenyl|-2-ethyl-3-(1-ethyl-3 -methoxypropyl)-ZN-imshazo|(4,5-b|pyridine; 7-(d-chloro-4--trifluoromethyl)phenyl|-3-(1-ethyl-3-methoxypropyl)-2-methoxy-ZN- imidazo(4,5-b|pyridine; 7-(2-chloro-4-methoxyphens)-2-eth l-3-(1-ethyl-3-methoxypropyl)-ZH-imidazo(4,5-b|pyridine; 7-(2-chloro-4-methoxyphenyl)-3-(1-ethyl-3-methoxypropyl)-2-methoxy-ZN-imidazoi|4,5-p|pyridine; 7-(2-chloro-5-fluoro-4-methoxyphenyl)-2-ethyl-3-(1-ethyl-3-methoxypropyl)-ZH-imidazo|4,5-b|pyridine; 7-(2-chloro-5-fluoro-4-methoxyphenyl)-3-(1-ethyl-3-methoxypropyl)-2-methoxy-ZN-imidazo(4,5-b|pyridine; 2-ethyl-3- (1-ethyl-3-methoxypropyl)-7-(4-methoxy-2,5-dimethylphenyl)-ZH-imidazoi|4,5-B|pyridine; 3-(1-ethyl-3-methoxypropyl)-2 -methoxy-7-(4-methoxy-2,5-dimethylphenyl)-ZH-imidazo(|4,5-b|pyridine; 2-ethyl-3-(1-ethyl-3-methoxypropyl)-7-(5 -fluoro-4-methoxy-2-methylphenyl)-ZH-imidazo(4,5-b|pyridinium; 3-(1-ethyl-3-methoxypropyl)-7-(5-fluoro-4-methoxy-2-methylphenyl) )-2-methoxy-ZN-imidazo(4,5-b|pyridipine; 7-(2-chloro-5-fluoro-4-methylphenyl)-2-ethyl-3-(1-ethyl-3-methoxypropyl)- ZH-imidazo(|4,5-b|pyridine; 7-(2-chloro-5-fluoro-4-methylphenyl)-3-(1-ethyl-3-methoxypropyl)-2-methoxy-ZH-imidazo|4 ,5-b|pyridine; 7-(d-chloro-4-(methylsulfonyl)phenyl|-2-ethyl-3-(1-ethyl-3-methoxypropyl)-ZN-imidazo(|4,5-b|pyridine ; 7-(d-chloro-4--(methylulfonyl)phenyl|-3-(1-ethyl-3-methoxypropyl)-2-methoxy-ZN-imidazo(4,5-p|pyridine; 1-(3- chloro-4-(2-ethyl-3-(1-ethyl-3-methoxypropyl)-ZH-imidazo(4,5-b|pyridin-7-ylIfenyl)-1-ethanol; 1-(3-chloro-4 -I3-(1-ethyl-3-methoxypropyl )-2-methoxy-ZN-imidazo(4,5-b|pyridin-7-yl|phenyl)-1-ethanol; 1-05-(2-ethyl-3-(1-ethyl-3-methoxypropyl)-ZH-imidazo(4,5-5|pyridin-7-yl|-b-methyl-2-pyridinyl)-1-ethanol 1-15-I(3-(1-ethyl-3-methoxypropyl)-2-methoxy-ZH-imidazo(4,5-b|pyridin-7-yl|-b-methyl-2-pyridinyl)-1 - ethanol;

2-ethyl-3-(1-ethyl-3-methoxypropyl)-7-(b-methoxy-2-methyl-33-pyridinyl)-ZH-imidazo(|4,5-b|Ipyridmn; 3-(1- ethyl-3-methoxypropyl)-2-methoxy-7-(6b-methoxy-2-methyl-3-pyridinyl)-ZH-imidazo(4,5-p|pyridine; 7-(2,6-dimethoxy-3- pyridinyl)-2-ethyl-3-(1-ethyl-3-methoxypropyl)-ZH-imidazo(4,5-b|pyridine; 7-(2,6-dimethoxy-3-pyridinyl)-3-(1- ethyl-3-methoxypropyl)-2-methoxy-ZN-imidazo(4,5-b|pyridine; 7-(2,6-dimethyl-3-pyridinyl)-2-ethyl-3-(1-ethyl-3- methoxypropyl)-ZH-imidazo(|4,5-b|pyridine; 7-(2,6-dimethyl-Z-pyridinyl)-3-(1-ethyl-Z-methoxypropyl)-2-methoxy-ZH-imidazo| 4,5-b|pyridine; 2-ethyl-3-(1-ethyl-3-methoxypropyl)-7-(2,5,6-trimethyl-3-pyridinyl)-ZH-imidazo|4,5-p| pyridine; 3-11-ethyl-3-methoxypropyl)-2-methoxy-7-(2,5,6-trimethyl-3-pyridinyl)-ZH-imidazo(|4,5-b|pyridine; 7-(2,4 -dichlorophenyl)-2-ethyl-3-(1-methoxymethyl)propyl|-ZH-imidazo|4,5-b|pyridine; 7-(2,4-dichlorophenyl)-2-methoxy-3-|11-( methoxymethyl)propyl|-ZH-imidazo(4,5-p|pyridine; 7-(d-chloro-4--trifluoromethyl)phenyl1-2-ethyl-3-/1-(methoxymethyl)propyl|-ZH-imidazo( |4,5-p|pyrid mp; 7-(d-chloro-4--trifluoromethyl)phenyl|-2-methoxy-3-|11-(methoxymethyl)propyl|-ZH-imidazo(4,5-b|pyridine; 7-(2-chloro-5 -fluoro-4-methylphenyl)-2-ethyl-3-|1-(methoxymethyl)propyl|-ZH-imidazo(4,5-b|pyridine; 7-(2-chloro-5-fluoro-4-methylphenyl) -2-methoxy-3-|1-(methoxymethyl)propyl|-ZH-imidazo|4,5-b|pyridine; 2-ethyl-7-(4-methoxy-2,5-dimethylphenyl)-3-(1 -(methoxymethyl)propyl|-ZH-imidazo(|4,5-b|pyridy; 2-methoxy-7-(4-methoxy-2,5-dimethylphenyl)-3-|1-(methoxymethyl)propyl|-ZH -imidazo(4,5-b|pyridine; 2-ethyl-7-(5-fluoro-4-methoxy-2-methylphenyl)-3-11-(methoxymethyl)propyl|-ZH-imidazo(4,5-b |pyridine; 7-(5-fluoro-4-methoxy-4-methylphenyl)-2-methoxy-3-|1-(methoxymethyl)propyl|-ZH-imidazo(4,5-b|pyridine; 2-ethyl- 3-|1-(methoxymethyl)propyl|-7-(b-methoxy-2-methyl-3-pyridinyl)-ZH-imidazo(4,5-b|pyridine; 2-methoxy-3-|1-(methoxymethyl )propyl|-7-(b-methoxy-2-methyl-3-pyridinyl)-ZH-imidazo(4,5-p|pyridine; 7-(2,6-dimethoxy-3-pyridinyl)-2-ethyl- 3-|1-(Methoxymethyl)propyl|-ZN-imidazo(4,5-b|pyridine; 7-(2:6-dimethoxy-3-pyridinide)-2-methoxy-3-|1-(methoxy Imethyl)propshy-ZN-imidazo(|4,5-b|pyridine; 7-(2,6-limethyl-3-pyridinyl)-2-ethyl-3-|1-(methoxymethyl)propyl|-3H-imidazo(4,5-b|pyridine; 7-(2,6-dimethyl- 3-pyridinyl)-2-methoxy-3-|1-(methoxymethyl)propyl|-ZH-imidazo(4,5-b|pyridnap; 2-ethyl-3-|1-(methoxymethyl)propyl|-7-( 2,5,6-trimethyl-3-pyridinyl)-ZH-imidazo(|4,5-b|pyridine; 2-methoxy-3-|1-(methoxymethyl)propyl|-7-(2,5,6- trimethyl-3-pyridinyl)-ZN-imidazo(4,5-b|pyridine; 7-(d-chloro-4-(methylsulfonyl)phenyl|-2-ethyl-3-|1-(methoxymethyl)protl|-ZN -imidazo|4,5-5|pyridipine; and 7-(d-chloro-4-(methylsulfonyl)phenyl|-2-methoxy-3-|1-(methoxymethyl)propyl|-ZN-imidazo(4,5- (2) In another, more preferred embodiment, the present invention provides a novel compound of formula Ia, wherein:

IN! is C3-C alkyl;

IN! is substituted with 0-1 substituents selected from -СМ, -5(О)п8и5, -СОВза, -СО28за, -МА'заСОвза, -

Mm(CO vza)", -"MA asom zada, dao" in, "SOM zada, 1-morpholinyl, 1-piperidinyl, 1-piperazinyl, and

Ca-in cycloalkyl, where 0-1 carbon atoms in Ca-in cycloalkyl are replaced by a group selected from -O-, -5(O)p-, -

MAza-, -МСО2В-, -МСОВ'- and -М5О2Во-, and where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from В!За, СО2В9, СОВИ and 50289; and

IN! is also substituted with 0-3 substituents independently selected in each case from B'2, B", B/E, C1-6 alkyl, C1-6 alkenyl, C0-6 alkynyl, Hg, CI, E, I, Si -4 haloalkyl, -OB"Za, -C1-» Alkoxy-Ci-2 alkyl, and MA Zad'va,

I(2K) In another, more preferred embodiment, the present invention provides a new compound of formula Ia, wherein:

X is selected from O, 5(O)n and a bond; n equals 0, 1 or 2;

IN! is selected from cyclopropyl, cyclobutyl and cyclopentyl:

IN! is substituted by 0-1 substituents selected from -СМ, -5(О)п8""5, -СОВЗа, -СО2832, and Са-в cycloalkyl, where 1 carbon atom in Са cycloalkyl is replaced by a group selected from - О-, -5(О)-, -МВ132-, -МСО»В-, -МСОВ- and -М5О2 В -;

IN! is also substituted with 0-2 substituents independently selected in each case from B'!2, B'E Su-v alkyl, Cg-v alkenyl, Co-v alkynyl, Bg, SI, E, CEz, CE2CEz, -« ОВ"3а, C. alkoxy-C-2 alkyl, and MA zad'va;

Ba is aryl and is selected from phenyl and indanyl, each H12 is substituted with 0-1 -OB" and 0-5 substituents independently selected in each case from C1-4 alkyl, C3-e cycloalkyl, B8, C1 .

IN!? is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from each in the case of C-4 alkyl, C3-e cycloalkyl, Bg, CI, E, SEz, -SM, -OB"", -5(O)tB!8, -SOV!", -MA7ad/za, and -SOMVard 'za, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B!za, CO»BIB, CO and 5028;

IN? is selected from C1-4 alkyl, C1-4 alkenyl, and C1-4 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and C1-4 alkoxy;

VZ and B? are independently selected in each case from H, Bg, CI, E, -CM, C-4 alkyl, C3-e cycloalkyl, C-4 alkoxy, MH", C-" alkylamino, and (C-4" alkyl)g- amino;

IN? is selected independently in each case from H, C1-4 alkyl and C3-6 cycloalkyl;

B" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl)- d'za and d'bg are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-Ci-b alkyl;

B!" is selected from C1-6 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-e cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl) );

Ba is selected from C 1-4 alkyl, C 1-2 haloalkyl, C 1-4 alkoxy-C 1-2 alkyl, and C 3-e cycloalkyl-C 1-2 alkyl;

Wb is selected from Ci-4 alkyl, Ci-haloalkyl, Ci-alkoxy-Ci-2 alkyl, C3-e cycloalkyl, and C3-6 cycloalkyl-Ci-2" alkyl;

IN? is independently selected in each case from H, Cm alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-c alkyl, phenyl and benzyl, each phenyl or benzyl being aryl-substituted 0-3 groups selected from C-4 alkyl, C8, C1, E, C1-4 haloalkyl, C1-4-alkoxy, C1-4h haloalkoxy, and dimethylamino;

Bza is independently selected in each case from H, C1-4 alkyl, C3-cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B", B!8 and BZ is selected in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C3-1 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, and C1-4 haloalkyl ; alternatively, in MA"B!Z component B" and BZ together form 1-pyrrolidinyl, 1-morpholipyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected with VZ, SO28!I, SOV": and 5028;

Ba and B/z are selected independently in each case from H, C1-e alkyl, C3-10 cycloalkyl, C3-e cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C1-4 alkyl, C3-e cycloalkyl, -OB'", Bg, C1, E, C1-4 haloalkyl, -CM, -5( O)pB8, -

SLEEP! -СО2В!", -MAZSOV', -MA"ZSO»2В!8, -MA!7В"Я, and -СОМВ!В"; and heteroaryl is independently selected in each case from pyridyl, pyrimidine, chryazyl, furanyl, quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, harolsh, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, voxazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothiens, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazol-2-on-yl, beisodioxolanyl and benzodioxane, each heteroaryl is substituted with 1-4 carbons atoms with a substituent selected independently in each case from C-e alkyl, C-e cycloalkyl, Bg, SI, E, C-4 haloalkyl, -СМ, -ОВ!", -5(О)тВ!8 -СОВ, -СО2В , -

ОС(О)В!В8, -МАЗСОВ', -Ш(СОВ)2, -МА!ЗСО»В'В8, "MAV, and -SOMVA" VU, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substitutes selected from Vya, СО2vcha, SOV'a and BO",

In another, even more preferred embodiment, the present invention provides a new compound of formula Ia, wherein:

X is selected from O, 5 and a bond;

B' is a substituted 0-1 substituents selected from -СМ, -СО28"3а, and Са-в cycloalkyl, where 0-1 vulyoleocs atoms in Св cycloalkyl are replaced by a group selected from -О-, -5(О) n-, and -MV"Za-;

B' is also substituted with 0-2 substituents independently selected in each case from Be, B/E, C 16 alkyl, C 8 alkenyl, C 8-b alkynyl, Bg, CI, E, CEz, -OB'Za, OH, - OSN», -OSNeSN», -«СНгОосСнН», -«СНаСНгОССнН»5, and -

MA Zad'va:

Va is aryl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеСН»

ОоСссНн(СНЗз)г, OSНg.СНеоСНн;", and ОСЕ", and 0-3 substituents chosen independently in each case from СНЗ,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH", and -C(O)M(CH3)"2;

IN!? is heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH» СНз, СН(СНЗз)",

СНоСНоснН;», cyclopropyl, ОСсН3, ОСН».СН3, ОСН(СН3)г, ОСН.СНесСнН», ОС», Вг, СИ, Е, СЕз, -СМ, ЗСН3, -МН», -

Mne Hz, -M(CHz)", -C(O)MH", -C(O)MNOHz, and -C(O)M(CHz)2, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from СН3, СО»2СН3, СОСН»3 and 502СН3;

IN? selected from СН3, СНеСН3, СН(СН3)2, and СНЕСНоСН5;

ВЗ and ВЗ are chosen independently in each case from Н, СН3, СНеСН3, СН(СН33)»2, and СНаСН»СН5; aryl is phenyl substituted with 2-4 substituents selected independently in each case from

СН3, СНосН», СН(СН3)», СННОСН», cyclopropyl, OSН3, OSН»СН», OSН(СН3)», OSНg.СНосНН», OS», Vy, SI, E,

СЕз, -СМ, 5СН3, 5О2СН3, -МНег, -МНОН3, -М(СН3)»2, -С(О)МН», -С(О)МНОН», and -С(О)М(СнН3)» , and, heteroaryl is independently selected in each case from pyridyl, indolyl, benzothienyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-bZ-oxide, 2,3-dihydrobenzothienyl-b-dioxide, indolinyl, and benzoxazolin-2-on-yl, each heteroaryl is a substituent with 2-4 carbon atoms substituted, which is chosen independently in each case from CH3, СНеCH3, СН(CH3)», СН»оСНоСН»3, cyclopropyl, ОСН3, ОСНеСН» 5, осн(СнНз)», OSN».СНосСнН», ОС», ВИ, СИ, Е, СЕз, -СМ, ЗСН3, 5О2СН3, -МНг, -МНОН3, -МЩ(СН3)2, -С(О) MN", -

С(О)МНеН", and -С(О)М(СНЗ3)", and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО»2СН3, СОСН» and 5О2СН». (2) In another, more preferred embodiment, the present invention provides a novel compound of formula Ia, wherein:

IN! is substituted by 0-2 substituents chosen independently in each case from Ba, B'!E, СН3, СНеСН»

СсН(СН3)г, СНСНоСН з, -(СНg)зСН3, -"СН-СН", -СНеСН(СнН3), -СН-СН, -"СН-С(СН3), -СНгОосСнН", -СНаСНгоснНН 5, E, and SEz;

Ba is a phenyl substituted with 0-1 substituents selected from OSH3, OSNoCH3, OSH(CH3)".

ОоСНоСНосНН», and ОСЕ», and 0-2 substituents chosen independently in each case from СН3, СНоСН3З3,

СН(СНЗ3)», СНеСНоСН»», Vg, SI, E, SEz, -SM, and ZON;

IN!? is a heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, СНаCH3, CH( СН3)г, СНаСНоСН», OSN»

ОоСНосСнН», ОС», Ви, СИ, Е, СЕз, -СМ, and 5СН»з, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО2СН3, СОСН» and 502СН3;

B2 is selected from СН3, СНеСН», and СН(СН3)»;

VZ and VZ are selected independently in each case from H and SNZ; aryl is phenyl substituted with 2-4 substituents selected independently in each case from

СН3, СНосН», СН(СН3)», СННОСН», cyclopropyl, OSН3, OSН»СН», OSН(СН3)», OSНg.СНосНН», OS», Vy, SI, E,

СЕз, -СМ, 5СНз, 5О2СНз, -МНег, -МНОНз, -М(СН3)2, -"С(О)МН", -ФС(СО)МНОН», and -С(СО)М(СН5)» , and, heteroarnl is a pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, CH3CH3, CH(CH3)g, CHaCHNeCH», cyclopropyl, OCH3, OCH3CH3, OCH(CH3)g , ОСНаСН»сСН з»,

ОС», В, СИ, Е, СЕз, -СМ, 5СН3, 5О02СН3, -МН», -МНОН3, -М(СН3)2, -С(О)МН», -С(О)МНСН3, and -С (ОМ(СНз)».

In another, even more preferred embodiment, the present invention provides a new compound of formula Ia, in which:

IN! with substituted 0-2 substituents chosen independently in each case from VZ, СН3, СНеСН3,

СсНн(СнЗз)», СНСНосН », -«(СНг)зСН3, -«СНгОСсН», -СНгСНгОснН», E, and SE»; and

B!g is phenyl substituted with 0-2 substituents chosen independently in each case from SNZz,

СноснН», СН(СН3)», СНгСНоСН,», Вг, СИ, Е, СЕз, -СМ, and СН». (20) In an even more preferred embodiment, the present invention provides a novel compound of the formula

Ia, in which:

O is phenyl substituted with 2-4 substituents chosen independently in each case from SNZ3,

СнесСнН»з, СН(СНз)», СНаСНесНС», cyclopropyl, OSН3, OSН»СН3, OSН(СН3)г2, OSНаСНоснН», ОСЕ:», Ви, СИ, Е, and

SEZ (game In another, even more preferred embodiment, the present invention provides a novel compound of formula Ia wherein: O is pyridyl substituted with 2-4 substituents independently selected in each case from CH3, CH3.CH3, CH(CH3 )g, СНаСНеСН», cyclopropyl, OSН3, OSНgСН3, OSН(СН3)г, OSНаСН»сСН z»,

OSE;", Vg, SI, E, and SEz. (ha) In another, more preferred embodiment, the present invention provides a novel compound of formula Ia, wherein:

IN! is selected from C1-10 alkyl, C1-10 alkenyl, C1-10 alkynyl, C3-6 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, and

C-4 alkoxy-C-4 alkyl;

IN! is substituted by a C3-C cycloalkyl group, where 0-1 carbon atoms in C1 cycloalkyl are replaced by a group selected from -О-, -5(О)п-, -МА1За-, -МСО»вВ/1в-, -МСОВ "B- and -MZO»2Во-;

IN! is also substituted with 0-3 substituents independently selected in each case from B'2, B", B/E, C1-6 alkyl, C1-6 alkenyl, C2-8 alkynyl, Bg, CI, E, I, Cm haloalkyl, -OV'Za, -KVzad'va, S.» alkoxy-Ci-2 alkyl, and C3- in cycloalkyl, which is substituted by 0-1 BZ and in which 0-1 carbon atoms of C1-cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)" - group;

B" is aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each B" is substituted 0-1 -

ОВ" and 0-5 substituents chosen independently in each case from C1-e alkyl, C3-e cycloalkyl, Bg, SI,

E, I, C-4 haloalkyl, -SM, nitro, 5H, -5(O)p8!8, -SOV!", -OS(ОВ8, -"MAzaSOOV", -SHSOV", -"MA' asom A adcha, -MA!5or2VV, -MAad'za, and -SOMVTad'za:

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, indazolyl, 2, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted by 0 -4 carbon atoms with a substituent selected independently in each case from C-C alkyl,

C3-in cycloalkyl, Bg, SI, E, I, C-4 haloalkyl, -SM, nitro, -OB"", 5H, -5(0)tB!8, -SOV!", -OC(O)B !V, -MA'zasSOVv/", -ЩСОВ7", -MmA'zasOoM A tad'tza, "MA zaboO"vV, "MA taditza, and SOM 7arV/cha, | each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B'za, СО2Б!б, СОБе and 50280;

B": represents a heterocyclyl and is a saturated or partially saturated heteroaryl, each heterocyclyl is a substituted 0-4 carbon atom substituent independently selected in each case from C1-C alkyl,

C3-ie cycloalkyl, Vk, SI, E, I. Sm haloallyl, -SM, nitro, ОВ, 5Н, -5(О)0В!"?, Owl, -ОС(О)ВВ, - ма'zaСбОвВиЗа -М (СОвВЗа)» -MAaSOMvzadiba -MAzaboOodi 0 -MAiZadi ota -SOMAZadiba and each heterocyclyl is substituted on any nitrogen atom by 0-1 substituents selected from В'За, СО»

SLEEP! and 5028", and wherein any sulfur atom is, if desired, mono- or dioxidized. (27) In another, even more preferred embodiment, the present invention provides a novel compound of formula Ia wherein:

X is selected from O, 5(O)n and a bond; n equals 0, 1 or 2;

IN! is selected from C1-6 alkyl, C6-6 alkenyl, C6-6 alkynyl, and C3-6 cycloalkyl;

IN! is a substituted C3-is cycloalkyl group, where 0-1 carbon atoms in Ca cycloalkyl are substituted by a group selected from -O-, -5(O)n-, and -MA13a-;

IN! is also substituted with 0-2 substituents independently selected in each case from B'3, VIB, C6 alkyl, C6 alkenyl, C6 alkynyl, Hg, C1, E, CE3, CE2CE3, -OVZa, -MVZad' va, C-2 alkoxy-C-2 alkyl, and C3-6 cycloalkyl, which is substituted 0-1 V? and in which 0-1 carbon atoms of Ca cycloalkyl are replaced by -O-;

IN? is aryl and is selected from phenyl and indanyl, each Be is substituted with 0-1 -OB" and 0-5 substituents independently selected in each case from C-4 alkyl, C3-e cycloalkyl, Bg, C1, E, C -4 haloalkyl, -SM, -5(O)p8!8, -SOV!", -"MAad/za and -SOMAadcha;

IN!? is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from each in the case of C1-4 alkyl, C3-e cycloalkyl,

Vg SI E, SEz, -"SM, "OV! -5(O)tV"8, -SOV'", -MAad'za and -SOMVad'cha | each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B'za, SOVA, SOV and 50280;

IN? is selected from C1-6 alkyl, C1-6 alkenyl, and C1-1 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and C1-6 alkoxy;

VAZ and VZ are chosen independently in each case from H, Vg, SI, E, -SM, Si. alkyl, C3 cycloalkyl, C1-4 alkoxy, MH", Ci-" alkylamino, and (Ci-4" alkyl)"-amino;

IN? is selected independently in each case from H, C1-4 alkyl and C3-6 cycloalkyl;

B" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl)- d'za and d'bg are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-Ci-b alkyl;

B!" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-e cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl) );

Ba is selected from C 1-4 alkyl, C 1-2 haloalkyl, C 1-4 alkoxy-C 1-2 alkyl, and C 3-e cycloalkyl-C 1-2 alkyl;

Vo is selected from C1-6 alkyl, C1-6 haloalkyl, C1-6 oxy-C1-alkyl, C3-6 cycloalkyl, and C3-6 cycloalkyl-C1-2 alkyl;

B" is independently selected in each case from H, C-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl, and benzyl, each phenyl or benzyl being 0-3 aryl substituted groups that selected from C-4 alkyl, C-4 alkyl, C-4 alkyl, C-4 haloalkyl, C-4 haloalkyl, and dimethylamino;

Bza is independently selected in each case from H, C1-4 alkyl, C3-cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B", B18 and B3 is selected in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C3-1 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, and C1-6 haloalkyl ; alternatively, in MB'"B"In component B" and B'Z together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents, which are selected from VZ, СО28!Я, SOV": and 5028;

Ba and B/zeg are independently selected in each case from H, C3-is alkyl, C3-io cycloalkyl, C3-is cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C1-4 alkyl, C3-e cycloalkyl, -OB'", B1, C1, E, C1-4 haloalkyl, -CM, -5( O)pB8, -

SLEEP! -СО2В!", -MAZSOV', -MA"ZSO»2В!8, -MA!7В"Я, and -СОМВ!В"; and heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted on 1-4 carbon atoms a substituent selected independently in each case from C3-e alkyl, C3-e cycloalkyl, Bg, CI, E, C-4 haloalkyl, -CM, -ОВ'", -5(0)тВ!8, -СОВ! ", -СО28, -

OS(O)V!V, -MAZSOV', -SHCSOV' 2", -MA!ZSO»V8, -MA!VYA, and -"SOMA! B, and each heteroaryl is substituted on any nitrogen atom 0-1 with substituents selected from B'5, СО2в'cha, СОВ'a, and 5028, (25) In another, even more preferred embodiment, this the invention introduces a new compound of formula Ia, in which:

X is selected from O, 5 and a bond; B' is a C-C alkyl;

IN! is a substituted C3-e alkyl, where 0-1 carbon atoms in the C3-e cycloalkyl are substituted by a group selected from -0-, -5(O)n-, and -MA13a-;

B' is also substituted with 0-2 substituents selected independently in each case from Bhe, Bhe, C 6 alkyl, Cg-c alkenyl, Cg-c alkynyl, E, Cez, -OB'Za, -MAZad'ba " ЗНаОСН»з, -СНаСНгОССнН», and C3-in cycloalkyl, which is substituted by 0-1 CH3 and in which 0-1 carbon atoms of Cl-in cycloalkyl are replaced by -O-; provided that B' is different from cyclohexyl - (CHg)" - group;

Va is aryl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеСН»

ОоСссНн(СНЗз)г, OSНg.СНеоСНн;", and ОСЕ", and 0-3 substituents chosen independently in each case from СНЗ,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH", and -C(O)M(CH3)"2;

IN!? is heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH» СНз, СН(СНЗз)",

СНоСНоснН;», cyclopropyl, ОСсНз, ОСН».СН», ОСН(СН3)г, ОСН.СНеСснН», ОС», Вг, СИ, Е, СЕз, -СМ, ЗСНз, -МН», -

Mne Hz, -M(CHz)", -C(O)MH", -C(O)MNOHz, and -C(O)M(CHz)2, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from СН3, СО»2СН3, СОСН»3 and 502СН3;

B2 is selected from СН3, СНеСН3, СН(СН3)»2, and СНаСН»СН5;

ВЗ and ВЗ are chosen independently in each case from Н, СН3, СНеСН3, СН(СН33)г, and СНаСНоСН»; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CH33,

SnesnH»z, CH(CHz)», СНСНоCH», cyclopropyl, OSNz, OSNoCH», OSN(СН3z)», OSN-СНоСН;», ОСЕ:;», VG, SI, E, SEz, -SM, 5СНz, 5О2СН3, -МНг, -МНОСН»3, -М(СН3)», -С(О)МН», -С(О)МНОН», and -С(О)М(СН3)», and the heteroaryl is selected independently in each case from pyridyl, indolyl, benzothienyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-bZ-oxide, 2,3-dihydrobenzothienyl-b-dioxide, indolinyl, and benzoxazolin-2- on-yl, each heteroaryl is a substituent substituted by 2-4 carbon atoms, chosen independently in each case from CH3, СНеCH3, СН(CH3)», СНаСНеаСН»3, cyclopropyl, ОСН3, ОСНегСН», осНн(СнН3)». OSN».СНосСнН», OS», VG, SI, E, SEz, -SM, ZSNz, 5О2СНz, -МНг, -МНОНз, -МЩ(СНз)2, -С(О)МН», -

С(О)МНеН", and -С(О)М(СНЗ)", and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО2СН3, СОСН» and 5О»СнН. (2U In another, even more preferred embodiment, the present invention provides a novel compound of formula Ia wherein:

B' is (cyclopropyl)C:alkyl or (cyclobutyl)C:alkyl;

IN! is substituted by 1-2 substituents chosen independently in each case from Ba, B'!E, СН3, СНеСН»

СсН(СН3)г, СНСНоСН з, -(СНг)зСН3, -СНеСН», -СН-СН(СнН3), -СН-СН, -СН-С(СН3), -СНгоОоСссСН», -СНаСНхОСснН 5, E,

CE3, cyclopropyl, CH3-cyclopropyl, cyclobutyl, CH3-cyclobutyl, cyclopentyl, CH3-cyclopentyl;

B!g is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеCH», and ОСЕ», and 0-2 substituents selected independently in each case from CH3, CH»CH3, CH(CH3)» СНгСНоСН;», Vg, SI, E,

SEz, -SM, and 5СН»Зз;

IN!? is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CHNaCH3, CH (СН3)г, СНаСНоСН», OSN»

ОоСНосСнН», OS», Vg, SI, E, SEz, -SM, and 5CH»z, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from CH3, СО2СН3, СОСН» and 502СН3;

IN? is chosen from СН3, СНеСН», and СН(СН3)»;

VZ and VZ are chosen independently in each case from H and CHz; aryl is phenyl substituted with 2-4 substituents chosen independently in each case from CH3, СНеCH3, CH(CH3)», СННеоСнН5», cyclopropyl, ОСН3, ОСН»CH3, ОСН(СН3)2, ОСН.СНегсСнН» , OS», Vg, SI, E, SEz, -SM, 5СНz, 5О2СНz, -МН», -

Mne Nz, -M(CHz)g) -"С(О)МНаг, -С(О)МНСНз, and -С(О)М(СНЗ)»2; and, heteroaryl is a pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, CH3CH3, CH(CH3)».

SnHosSnHosnH», cyclopropyl, OSH3, OSNoCH3, OSH(CH3)g», OSH»CH2OSCH3, OS», Vg, SI, ER, SE3, -SM, 5CH»vz, 5O»CH3, -MH»g, -MNOH3, -M(CH3), -"С(О)МН", -С(О)МНС Na, and -С(О)М(СН3)". (2Ch| In another, even more preferred embodiment, the present invention provides a novel compound of formula Ia, wherein:

B' is (cyclopropyl)C:alkyl or (cyclobutyl)C:alkyl;

IN! is substituted by 1-2 substituents chosen independently in each case from В"", ВЕ, СН3, СНеСН»З.,

Ссн(Снз)», СНСНесСН», -(СНег)зСНз, -"СНАСН", -"СНАСН(СН3), -СН-СН, -СН-С(СН3), -СНхОснН», -СНаСНгОСснНН 5, E,

CE", cyclopropyl, and CH3-cyclopropyl;

B!g is phenyl substituted with 0-2 substituents chosen independently in each case from SNZ,

SnosnH», CH(CH3)», CHgSNoCH», Vg, SI, ER, SEz, -SM, and 5CHZ;

IN!" is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, and pyrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, СНеCH3, CH(CH3)" , СНЕСНоСН», OSНz, OSNeСН», ОСЕ:», Vg,

SI, E, SEz, -SM, and SN". (2M| In another, even more preferred embodiment, the present invention provides a novel compound of formula Ia wherein: O is phenyl substituted with 2-4 substituents independently selected in each case from CH3, CH3CH3, CH(CH3 )", CH»CNeoCH3, cyclopropyl, OSH3, OSNaCH3, OSH(CH33)",

OosSnN. NesnN;», OS», Vg, SI, E, and SEz. (2M| In another variant, which is even more preferred, the present invention introduces a new compound of formula Ia, in which: O is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, СНеCH3, CH(CH3)», CH»CHneCH»3, cyclopropyl, OSH»3,

OosSNsN", OSN(SNz)", OSNSNoSnN;", OS", Vg, SI, E, and SEz.

IZ In another preferred embodiment, the present invention provides a new compound of formula Ir:

IN,

M - in the entrance

Mt M r (15).

In another, more preferred embodiment, the present invention provides a novel compound of formula IB, wherein:

X is selected from O, 5(O)n and a bond; n equals 0, 1 or 2;

IN! is selected from C1-6 alkyl, C6-6 alkenyl, C6-6 alkynyl, and C3-6 cycloalkyl;

IN! is substituted by 0-1 substituents selected from -СМ, -5(О)пвы5, -СОВ1za, -5028/13a, and C3-C cycloalkyl, where 0-1 carbon atoms in CА-C cycloalkyl are substituted by a group selected with -О-, -5(О)п-, -МВЗа-, -МСО» VV. -

MSOV.- and -M5O" in/v.

IN! is also substituted with 0-2 substituents chosen independently in each "case from Ba, B", C 1 -C alkyl, C 2 -C alkenyl, C 2 -C alkynyl, HG, SI, E, CE3, CE2CE3, -OB'Za, - MdZad'va, Si." Alkoxy-Ci-2 alkyl, and C3-C cycloalkyl, which is substituted 0-1 V? and in which 0-1 carbon atoms of Ca cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)" - group;

IN? is aryl and is selected from phenyl and indanyl, each Be is substituted with 0-1 -OB" and 0-5 substituents independently selected in each case from C-4 alkyl, C3-e cycloalkyl, Bg, C1, E, C -4 haloalkyl, -SM, -5(O)p818, -"SOV, -MAad'za, and -SOMATadcha;

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from each in the case of C-4 alkyl, C3-- cycloalkyl. Bg, SI, E, SEz, -CM, -OB'", -5(O)tvB!8, -SOV!", -MAad/za, and -SOMA7ad'/za and each heteroaryl is substituted by any nitrogen atom 0-1 by substituents selected from В!za, СО»ВИБ, СО and 5О»n; provided that B' is different from -(CHg):-4-aryl or -(CHg)i-4-heteroaryl, wherein the aryl or heteroaryl group is substituted or unsubstituted;

B2 is selected from C1-4 alkyl, C1-4 alkenyl, and C1-4 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and Cm alkoxy;

B3 and B" are independently selected in each case from H, B8, C1, E, -CM, C1 alkyl, C3 cycloalkyl, C1-4 alkoxy, MH", C1-4 alkylamino, and (C1-4 alkyl)" -amino;

IN? is selected independently in each case from H, C1-4 alkyl and C3-6 cycloalkyl;

B" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl)- za and D'ba are independently selected in each case from H, Ci-4 alkyl, Ci-4 haloalkyl, Ci-4 alkoxy-Ci-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-Ci-v alkyl;

B!" is selected from C-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-e cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl) -;

The fork is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, and C3-e cycloalkyl-C1-2 alkyl;

Vo is selected from C1-6 alkyl, C1-6 haloalkyl, C1-6 oxy-C1-alkyl, C3-6 cycloalkyl, and C3-6 cycloalkyl-C1-2 alkyl;

B" is independently selected in each case from H, C-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl, and benzyl, each phenyl or benzyl being 0-3 aryl substituted groups that is selected from C-4 alkyl, C1-4 alkyl, C1-4 haloalkyl, C1-4 haloalkyl, C1-4 haloalkyl, and dimethylamino; diza, independently selected in each case from H, C1-4 alkyl, C3-7 cycloalkyl , and C3-is cycloalkyl-C1-6 alkyl;

B", B!8 and B!" is selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-6 alkyl, C1-4 haloalkyl; as an alternative, in MVV" component B" and B? together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from ВЗ, СО28!Я, SOВ": and 5028;

B" and B/za are independently selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C1-4 alkyl, C3-e cycloalkyl, -OB'", B1, C1, E, C1-4 haloalkyl, -CM, -5( O)pB8, -

Sov, -СО28!", -MA"SOV', -MA"ЗСО2В!В8, -MA!"В"Я, and -"SOMVA" V"; and heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothiens, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted on 1-4 carbon atoms by a substituent selected independently in each case from C3-6 alkyl, C3-6 cycloalkyl, C1, C1, E, C1-4 haloalkyl, -CM, -ОВ", -5(О)тВ!Б8, -СОВ! ", -СО2В8/, -

OS(O)V!V, -MAZSOV', -SHCSOV' 2", -MA!ZSO»V8, -MA!VYA, and -"SOMA! В, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from Ві, СО2віча, СОВ'а, and BO».

COMPOUNDS In another, even more preferred embodiment, the present invention provides a novel compound of formula IB, wherein:

X is selected from O, 5 and a bond; B' is substituted C-C alkyl;

IN! is substituted by 0-1 substituents selected from -СМ, -СО2Б"3а and C3-Я cycloalkyl, where 0-1 carbon atoms in Са-в cycloalkyl are replaced by a group selected from -О-, -«5(О) n-, and -"MAcha-;

IN! is also substituted with 0-2 substituents independently selected in each case from B'z, VIB, C6 alkyl, Cg-c alkenyl, Cg-c alkynyl, Bg, Si, E, Cez, -OVZa, -MVZad'va, WITH." alkoxy-Ci-2 alkyl, and C3-e cycloalkyl, which is substituted by 0-1 CH3 and in which 0-1 carbon atoms of C1-in cycloalkyl are replaced by -O-; provided that B' is different from cyclohexyl - (CHg)" - group;

IN! is aryl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеСН",

ОоСссНн(СНЗз)г, OSНg.СНеоСНн;", and ОСЕ", and 0-3 substituents chosen independently in each case from СНЗ,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH", and -C(O)M(CH3)"2;

IN!" is heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH» СНз, СН(СНЗз)",

СНоСНоснН;», cyclopropyl, ОСсН3, ОСН».СН3, ОСН(СН3)г, ОСН.СНесСнН», ОС», Вг, СИ, Е, СЕз, -СМ, ЗСН3, -МН», -

Mne Hz, -M(CHz)", -C(O)MH", -C(O)MNOHz, and -C(O)M(CHz)2, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from СН3, СО2СН3, СОСН»3 and 5О2СН3; provided that B! is different from -(CH2)i-4-aryl or -(CH2)1i-4-heteroaryl, where the aryl or heteroaryl group is substituted or unsubstituted;

IN? is chosen from CH3, CHgCH», CH(CH3)Hg, and СНеСНеCH»;

B3 and B" are independently selected in each case from H, CH3, CH2CH3, CH(CH33)g, and CNaCHNoCH"; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CH33,

СнеснН»з, СН(СН3з)», СНаСНосСнН», cyclopropyl, ОСН3, ОСНоCH», ОСН(СН33)г, ОСНаСНосСнН;», ОСЕ:», В, СИ, Е, СЕз, -СМ, 5СН3, 5О2СН3, - MHg, -MNOCH»z, -M(CHz)», -C(O)MH», -C(O)MNOVN», and -C(O)M(CHz)», and the heteroaryl is chosen independently in each case of pyridyl, indolyl, benzothienyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-bZ-oxide, 2,3-dihydrobenzothienyl-b-dioxide, indolinyl, and benzoxazolin-2-on-yl , each heteroaryl is a substituent substituted by 2-4 carbon atoms, which is chosen independently in each case from CH3, СНеCH3, СН(СН3)», СН»оСНоСН»3, cyclopropyl, ОСН3, ОСНеCH»5, осн(СнН3)». OSN».СНосСнН», OS», VI, SI, E, SEz, -SM, ZSNz, 5О2СНz, -МНг, -МНОНз, -М(СНз)», -С(О)МН», -

С(О)МНеН» and -С(О)М(СНЗ3)», and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО2СН3, СОСН» and 5О»СнН.

IZS| In another, even more preferred embodiment, the present invention provides a novel compound of formula IB wherein:

IN! is substituted by Si;

IN! is substituted 0-1 with substituents selected from -СМ, -СО»СНвз, and -СО2СНеСН»;

IN! is also substituted by 0-2 substituents chosen independently in each case from 22 V", CHz,

SnosSnHz, cH(CHz)", SNaSnesSnH", -(CHg)zCHz, -SNACH»o, -SNACH(CHz), -CH-CH, -CH-C(CHz), -CHgOSsH", -

СНснНоОоснН;», ER, CEz, cyclopropyl, CH3-cyclopropyl, cyclobutyl, CH3-cyclobutyl, cyclopentyl, CH3-cyclopentyl;

IN! is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеCH", and ОСЕ", and 0-2 substituents selected independently in each case from CH3, CH»CH3, CH(CH3)", CHgCHNoCH;" , Vg, SI, E,

SEz, -SM, and 5СН»Зз;

IN!" is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CHNaCH3, CH (СН3)г, СНаСНоСН», OSN»

ОоСНосН», ОСЕ;», Ви, СИ, Е, СЕз, -СМ, and ЗСН»вз, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО»2СН3, СОСН» and 5О2СН3; provided that B! is different from -(CH2)1-4-aryl or -(CH2):-"-heteroaryl, where the aryl or heteroaryl group is substituted or unsubstituted;

B2 is selected from СН3, СНеСН», and СН(СН3)»;

B3 and B" are independently selected in each case from H and CH3; aryl is phenyl substituted with 2-4 substituents independently selected in each case from

CHz, CHnosH», CH(CHz)», CHNSNoCH», cyclopropyl, OSHz, OSH»CH», OSH(CHz)», OSNg.CHosnH», OS», Vg, SI, E,

СЕз, -СМ, 5СНЗ, 5О2СНвз, -МНг, -МНОНз, -М(СНз)», -С(О)МН», -ФС(О)МНСН»з, and -С(О)М(СНЗ) "; and, heteroaryl is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, СНа.СН3, СН(СН3)г, СНаСНеСН», cyclopropyl, ОСН3, ОСН3СН3, ОСН(СН3)г, ОСНаСН»сСН з»,

OS», Vg, SI, E, SEz, -SM, 5СН3, 5О2СН3, -МНг, -МНОН3, -М(СН3)», -С(О)МН», -С(О)МНС Na, and - С(О)М(СНз)».

In another, even more preferred embodiment, the present invention provides a novel compound of formula IB, wherein:

IN! is a substituted (cyclopropyl)-Ci alkyl or (cyclobutyl)-Ci alkyl;

IN! is substituted 0-1 -CM;

IN! is also substituted with 0-1 substituents chosen independently in each case from B", B"", CH3,

SnosnH»z, CH(CHz)», СNaСНосCH», -(CHg)zCHz, -СНАСН»g, -«СНАСН(СНзи), -«СНаСН-СН, -СН-СН(СН»), Vg, SI, E, CE", cyclopropyl, and CH3-cyclopropyl;

IN! is also substituted 0-1 by substituents chosen independently in each case from B! VE, SNZz,

SnosSnHz, cH(CHz)", SNaSnesSnH", -(CHg)zCHz, -SNACH»o, -SNACH(CHz), -CH-CH, -CH-C(CHz), -CHgOSsH", -

СНННООССН;», E, SE3, cyclopropyl, and CH3-cyclopropyl;

IN!? is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, and pyrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, СНеCH3, CH(CH3)" , SNESNoSN", OSNz, OSNeSN", OSE", Vg,

SI, E, SEz, -SM, and SN".

In another, even more preferred embodiment, the present invention provides a novel compound of formula IB wherein:

WOW! is (cyclopropyl)-Ci alkyl or (cyclobutyl)-Ci alkyl, substituted by 1 substituent, which is selected independently in each case from B, B!E, CH3, CH»CH3, CH(CH3)», СНаСНеСН», -( СНг)зСН», - сСн-сСнНг, -СНАСН(СН3), -СНеСН, -СНеСН(СН3), -СН»2ОсСН:, -СНаСН»ОСснН», E, SEz, cyclopropyl, and СН3- cyclopropyl;

B!g is phenyl substituted with 0-2 substituents chosen independently in each case from SNZ,

SNeoSN", SI, E, and SEz;

IN!" is a heteroaryl selected from furanyl, thienyl, and isoxazolyl, each heteroaryl being a 0-2 carbon substituted substituent independently selected in each case from CH33,

OSN;", SI, E, and SEz.

IZI In an even more preferred embodiment, the present invention provides a novel compound of formula IB in which:

B' is selected from the group (cyclopropyl)u CH-CH3, (cyclopropyl)u CH-CHeCH»3, (cyclopropyl CH-CHhOCH), (cyclopropyl CH-CHNa.CHoSCH), (cyclopropyl CH-CHNa.CHhOsnH", (cyclopropyl )2CH, phenyl(cyclopropyl)CH, furanyl(cyclopropyl)CH, thienyl(cyclopropyl)CH, isoxazolyl(cyclopropyl)CH, (CH3-furanyl) (cyclopropyl)CH, (cyclobutyl)C H-CH333, (cyclobutyl)us H -СНеСнН», (cyclobutylusН-СНхОСН 5, (cyclobutyl)/СН-СНаСНоСН», (cyclobutyluСН-СНа.СНхОСсСН», (cyclobutyl)2СН, phenyl(cyclobutyl)СН, furanyl(icyclobutyl) СН, thienyl(icyclo.butyl) CH, isoxazolyl(icyclobutyl)CH, and (CH3-furanyl)(cyclobutyl)CH.

In another, more preferred embodiment, the present invention provides a novel compound of formula IB wherein: O is phenyl substituted with 2-4 substituents independently selected in each case from CH3, CH3.CH3, CH СН3)г, СНаСНеСН», cyclopropyl, OSН3, OSНgСН3, OSН(СН3)г, OSНаСН»сСН z»,

OSE:", VG, SI, E, and SEz.

In another, more preferred embodiment, the present invention provides a new compound of formula Ia, in which: O is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, CH3CH3, CH(CH3 )", СНаСНаСН»з, cyclopropshu, OSН3, OSНегСН»,

OoSsNn(SNz)", OSNaSNSN", OSE:, Vg, SI, E, and SEz.

IZI| In another preferred embodiment, the present invention provides a novel compound of formula Ia, wherein said compound is selected from the group consisting of: 1-(1-Diclopropylpropyl)-4-(2,4-dichlorophenyl)-2-ethyl-31-imidazo|4 ,5-s| pyridine; 1-(1-cyclopropylpropyl)-4-(2,4-dichlorophenyl)-2-methoxy-1H-imidazoi|4,5-s| pyridine; 1-(1-Diclopropylpropyl)-2-ethyl-4-(2-methyl-4-(trifluoromethyl)phenyl|-1 H-imidazo(4,5-c| pyridine; 4-(2-chloro-4-- trifluoromethyl)phenyl|-1-(1-cyclopropylpropyl)-2-ethyl-1H-imidazoi(4,5-c| pyridine; 4-(2-chloro-4--trifluoromethyl)phenyl|-1-(1-cyclopropylpropyl )-2-methoxy-1H-imidazoi4,5-c|pyridine;

4-(2-chloro-4-trifluoromethyl)phenyl|-1-(1-cyclopropylpropyl)-2-(methylsulfanyl)-1H-imidazoi|4,5-s pyridine; 4-(2-chloro-4-methoxyphenyl)-1-(1-cyclopropylpropyl)-2-ethyl-1H-imidazoi|4,5-s| pyridine; 4-(2-chloro-4-methoxyphenyl)-1-(1-cyclopropylpropyl)-2-methoxy-1H-imidazoi|4,5-s| pyridine; 1-(1-cyclopropylpropyl)-2-ethyl-4-(4-methoxy-2,5-dimethylphenyl)-1H-imidazo(4,5-c|pyridine; 1-(1-cyclopropylpropyl)-2- methoxy-4-(4-methoxy-2,5-dimethylphenyl)-1H-imidazoi|4,5-s|pyridine; 4-(2-chloro-4-methoxyphenyl)-1-(1-cyclopropylpropyl)-2- ethyl-1H-imidazoi|4,5-c|pyridine; 4-(2-chloro-4-methoxyphenyl)-1-(1-cyclopropylpropyl)-2-methoxy-1H-imidazoi|4,5-c|pyridine; 4-(2-chloro-5-fluoro-4-methoxyphenyl)-1-(1-cyclopropylpropyl)-2-ethyl-1H-imidazo(|4,5-c| pyridine; 4-(2-chloro-fluoro -4-msoxyphenyl)-1-(1-cyclopropylpropyl)-2-methoxy-1H-imidazoi|4,5-s| pyridine; 4-(2-chloro-5-fluoro-4-methylphenyl)-1-(1 -dcyclopropylpropyl)-2-ethyl-1H-imidazo(4,5-c|pyridine; 2.4-(2-chloro-fluoro-4-methylphenyl)-1-(1-cyclopropylpropyl)-2-methoxy-5-imidazo |4,5-s| pyridine; 1-(1-cyclopropylpropyl)-2-methoxy-4-(2,4,5-trimethylphenyl)-1H-imidazoi(4,5-s| pyridine; 1-(1- cyclopropylpropyl)-2-ethyl-4-(2,4,5-trimethylphenyl)-1H-imidazo(4,5-c| pyridine; 1-(1-cyclopropylpropyl)-2-ethyl-4-(2,5 ,6-trimethyl-3-pyridinyl)-1H-imidazoi(4,5-c| pyridine; 1-( 1-cyclopropylpropyl)-2-methoxy-4-(2,5,6-trimethyl-3-pyridinyl)-1H-imidazo|4,5-c| pyridine; 1-(1-cyclopropylpropyl)-4-(2,6-dimethyl-3-pyridinyl)-2-ethyl-1H-imidazoi(4,5-c| pyridine; 1-(1-cyclopropylpropyl)-4-( 2,6-dimethyl-3-pyridinyl)-2-methoxy-1H-imidazoi|4,5-c|pyridine; 1-(1-cyclopropylpropyl)-4-(2,6-dimethoxy-3-pyridinyl)-2 -ethyl-1H-imidazoi|4,5-s|pyridine; 4-(2,4-dichlorophenyl)-2-ethyl-1-(1-ethylpropyl)-1H-imidazoi|4,5-s|pyridine; 4-(2,4-dichlorophenyl)-1-(1-ethylpropyl)-2-methoxy-1H-imidazoi|4,5-s| pyridine; 4-(2-chloro-4--trifluoromethyl)phenyl|-1 -(1-ethylpropyl)-2-methoxy-1H-imidazoi|4,5-s|pyridine; 4-(2-chloro-4--trifluoromethyl)phenyl|-2-ethyl-1-(1-ethylpropyl) -1H-imidazoi(4,5-c| pyridine; 4-(2-chloro-4--(methylsulfonyl)phenyl)|-2-ethyl-1-(1-ethylpropyl)-1 H-imidazoi|4,5- c| pyridine; 4-(2-chloro-4 (methylsulfonyl)phenyl|-1-(1-ethylpropyl)-2-methoxy-1H-imidazoi4,5-c| pyridine; 2-ethyl-1-(1-ethylpropyl) )-4-(4-methoxy-2,5-dimethylphenyl)-1H-imidazoi|4,5-s| pyridine; 1-(1-ethylpropyl)-2-methoxy-4-(4-methoxy-2,5 -dimethylphenyl)-1H-imidazoi4,5-c|pyridine; 4-(2-chloro-4-methoxyphenyl)-2-ethyl-1-(1-ethylpropyl)-1H-im idazoi (4.5-s| pyridine; 4-(2-chloro-4-methoxyphenyl)-1-(1-ethylpropyl)-2-methoxy-1H-imidazoi|4,5-s| pyridine; 2-ethyl-1-(1-ethylpropyl)-4-I(4-methoxy-2-(trifluoromethyl)phenyl|-1 H-imidazoi|4,5-c| pyridine; 1-(1-ethylpropyl)-2 -methoxy-4-(4-methoxy-2-(trifluoromethyl)phenyl|-1 H-imidazo(4,5-c| pyridine; 1-(1-ethylpropyl)-4-(5-fluoro-4-methoxy- 2-methylphenyl)-2-methoxy-1H-imidazoi|4,5-c|pyridine; 2-ethyl-1-(1-ethylpropyl)-4-(5-fluoro-4-methoxy-2-methylphenyl|-1 H-imidazo|4,5-s|pyridine;

C-chloro-4-(1-(1-ethylpropyl)-2-methoxy-1H-imidazo(|4,5-c| pyridin-4-yl|benzonitrile;

C-chloro-4-(2-ethyl-1-(1-ethylpropyl)-1H-imidazo(4,5-c|pyridin-4-yl|benzonitrile; 1-(3-chloro-4-(2- ethyl-1-(1-ethylpropyl)-1H-imidazo(|4,5-c|pyridin-4-yl|phenyl)-1-ethanol; 1-(3-chloro-4-I|1-(1 -ethylpropyl)-2-methoxy-1H-imidazoi(4,5-c|Ipyridin-4-ylIfenyl)-1-ethanol; 1-(dicyclopropylmethyl)-2-ethyl-4-(5-fluoro-4-methoxy- 2-methylphenyl)-1H-imidazo|4,5-c|Ipyridine; 1-(dicyclopropyl methyl)-4-(5-fluoro-4-methoxy-2-methylphenyl)-2-methoxy-1H-imidazoi|4, 5-c|pyridine; 4-(2-chloro-4-methoxyphenyl)-1-(dicyclopropylmethyl)-2-ethyl-1H-imidazo(4,5-c|pyridine; 4-(2-chloro-4-methoxyphenyl) )-1-(dicyclopropylmethyl)-2-methoxy-1H-imidazo(4,5-c|pyridine; 4-(2,4-dichlorophenyl)-1-(dicyclopropyl methyl)-2-ethyl-1H-imidazoi(4 ,5-c|Ipyridine; 4-(2,4-dichlorophenyl)-1-(dicyclopropylmethyl)-2-methoxy-1 H-imidazo|4,5-c|Ipyridine; 4-(2-chloro-4-- trifluoromethyl)phenyl|-1-(dicyclopropylmethyl)-2-ethyl-1H-imidazo(4,5-pyridine; 4-(2-chloro-4--trifluoromethyl)phenyl|-1-(dicyclopropylmethyl)-2-methoxy- 1 H-imidazo(|4,5-с|pyridine; 4-(2,4-dichlorophenyl)-1-(1-ethyl-3-m ethoxypropyl)-2-methoxy-1H-imidazo|4,5-c|Ipyridine; 4-(2,4-dichlorophenyl)-2-ethyl-1-(1-ethyl-3-methoxypropyl)-1H-imidazo(|4,5-c|Ipyridine; 4-(2-chloro-4-- trifluoromethyl)phenyl|-1-(1-ethyl-3-methoxypropyl)-2-methoxy-1H-imidazo(4,5-c|pyridine; 4-(2-chloro-4-trifluoromethyl)phenyl|-2- ethyl-1-(1-ethyl-3-methoxypropyl)-1H-imidazo(4,5-c|pyridine; 4-(2-chloro-4-methoxyphenyl)-1-(1-ethyl-3-methoxypropyl) -2-methoxy-1H-imidazo|4,5-c|pyridine; 4-(2-chloro-4-methoxyphenyl)-2-ethyl-1-(1-ethyl-3-methoxypropyl)-1H-Imidazoi (4,5-s|pyridine; 4-(2-chloro-5-fluoro-4-methoxyphenyl)-1-(1-ethyl-3-methoxypropyl)-2-methoxy-1H-imidazo(4,5-s |pyridine; 4-(2-chloro-5-fluoro-4-methoxyphenyl)-2-ethyl-1-(1-ethyl-3-methoxypropyl)-1H-imidazo|4,5-c|pyridine; 1- (1-ethyl-3-methoxypropyl)-2-methoxy-4-(4-methoxy-2,5-dimethylphenyl)-1H-imidazo(|4,5-c|Ipyridine; 2-ethyl-1-(1- ethyl-3-methoxypropyl)-4-(4-methoxy-2,5-dimethylphenyl)-1H-imidazo(4,5-c|pyridine; 2-ethyl-1-(1-ethyl-3-methoxypropyl)-4 -(5-fluoro-4-methoxy-2-methylphenyl)-1H-imidazo|4,5-pyridine; 1-(1-ethyl-3-methoxypropyl)-4-(5-fluoro-4-methoxy-2- methylphenyl)-2-me toxy-1H-imidazoi4,5-c|Ipyridine; 4-(2-chloro-5-fluoro-4-methylphenyl)-1-(1-ethyl-3-methoxypropyl)-2-methoxy-1H-imidazo(4,5-c|Ipyridine; 4-(2- chloro-5-fluoro-4-methylphenyl)-2-ethyl-1-(1-ethyl-3-methoxypropyl)-1H-imidazo(4,5-pyridine; 4-(2-chloro-4--(methylsulfonyl) phenyl|-1-(1-ethyl-3-methoxypropyl)-2-methoxy-1H-imidazo(4,5-pyridine; 4-(2-chloro-4-(methylsulfonyl)phenyl)-2-ethyl-1- (1-ethyl-3-methoxypropyl)-1H-imidazoi(4,5-c|pyridine; 1-(3-chloro-4-|1-(1-ethyl-3-methoxypropyl)-2-methoxy-1H- imidazo(4,5-c|Ipyridin-4-yl|phenyl)-1-ethanol; 1-(3-chloro-4-(2-ethyl-1-(1-ethyl-3-methoxypropyl)-1H-imidazo (4,5-s|Ipyridin-4-yl|phenyl)-1-ethanol; 1-05-(11-(1-ethyl-3-methoxypropyl)-2-methoxy-1H-imidazo(4,5-s |Ipyridin-4-yl|I-bE-methyl-2-pyridinyl)-1-ethanol; 1-5-(2-ethyl-1-(1-ethyl-3-methoxypropyl)-1H-imidazo(4,5 -c|Ipyridin-4-ylI|I-6-methyl-2-pyridinyl)-1-ethanol; 1-(1-ethyl-3-methoxypropyl)-2-methoxy-4-(b-methoxy-2-methyl -3-pyridinyl)-1 H-imidazo|4,5-pyridine; 2-ethyl-1-(1-ethyl-3-methoxypropyl)-4-(b-methoxy-2-methyl-3-pyridinyl)-1 H-imidazo(|4,5-s|Ipyridine; 4-(2,6-dimethoc si-3-pyridinyl)-2-ethyl-1-(1-ethyl-3-methoxypropyl)-1H-imidazo(|4,5-c|Ipyridine; 4-(2,6-dimethoxy-3-pyridinyl-1-1-ethyl-3-methoxypropyl)-2-methoxy-1H-imidazo|4,5-c|pyridine; 4-(2,6-Dimethyl-3-pyridinyl)-1-(1-ethyl-3-methoxypropyl)-2-methoxy-1H-imidazo|4,5-c|Ipyridine;

4-(2,6-dimethyl-3-pyridinyl)-2-ethyl-1-1-ethyl-3-methoxypropyl)-1H-imidazoi(4,5-c|Ipyridine; 2-ethyl-1-(1- ethyl-3-methoxypropyl)-4-(2,5,6-trimethyl-3-pyridinyl)-1 H-imidazo(|4,5-c|Ipyridine; 1-(1-ethyl-3-methoxypropyl)-2 -methoxy-4-(2,5,6-trimethyl-3-pyridinyl)-1H-imidazo(4,5-c|Ipyridine; 4-(2,4-dichlorophenyl)-2-ethyl-1-I|1- (methoxymethyl)propyl|-1H-imidazo(4,5-c|Ipyridine; 4-(2,4-dichlorophenyl)-2-methoxy-1-|1-(methoxymethyl)propyl|-1H-imidazoi(4,5 -c|pyridine; 4-(2-chloro-4--trifluoromethyl)phenyl|-2-ethyl-1 -|1 -"methoxymethyl)propyl|-1 H-imidazo(|4,5-c|pyridine; 4 -(2-chloro-4--trifluoromethyl)phenyl|-2-methoxy-1-|1-(methoxymethyl)propyl|-1 H-imidazo(4,5-c|pyridine; 4-(2-chloro-5 -fluoro-4-methylphenyl)-2-ethyl-1-|1-(methoxymethyl)propyl|-1 H-imidazo(|4,5-c|Ipyridine; 4-(2-chloro-5-fluoro-4- methylphenyl)-2-methoxy-1-11-(methoxymethyl)propyl|-1 H-imidazo|4,5-c|Ipyridine; 2-methoxy-4-(4-methoxy-2,5-dimethylphenyl)-1 - |1-(methoxymethyl)propyl|-1 H-imidazo|4,5-c|Ipyridine; 2-ethyl-4-(4-methoxy-2,5-dimethylphenyl)-1-H11-(methoxymethyl)prop l|-1 H-imidazo|4,5-s|pyridine; 2-ethyl-4-(5-fluoro-4-methoxy-2-methylphenyl)-1-P1-(methoxymethyl)propyl|-1H-imidazo(|4,5-c|Ipyridine; 4-(5-fluoro -4-methoxy-4-methylphenyl)-2-methoxy-1-|1-(methoxymethyl)propyl|-1 H-imidazo(4,5-c|Ipyridine; 2-methoxy-1-|1-(methoxymethyl) propyl|-4-(b-methoxy-2-methyl-3-pyridinyl)-1H-imidazoi(4,5-c|Ipyridine; 2-ethyl-1-I1-(methoxymethyl)propyl|-4-(b- methoxy-2-methyl-3-pyridinyl)-1H-imidazo|4,5-c|Ipyridine; 4-(2,6-dimethoxy-3-pyridinyl)-2-ethyl-1-(1-(methoxymethyl) propyl|-1 H-imidazo(4,5-c|Ipyridine; 4-(2,6-dimethoxy-3-pyridinyl)-2-methoxy-1-|1-(methoxymethyl)propyl|-1 H-imidazo( 4,5-c|pyridine; 4-(2,6-dimethyl-3-pyridinyl)-2-ethyl-1-|1-(methoxymethyl)propyl|-1H-imidazo|4,5-c|Ipyridine; 4-(2,6-dimethyl-3-pyridinyl)-2-methoxy-1-|1-(methoxymethyl)propyl|)-1 H-imidazo(|4,5-c|Ipyridine; 2-ethyl-1- 1-(Methoxymethyl)propyl|-4-(2,5,6-trimethyl-3-pyridinyl)-1H-imidazo|4,5-c|Ipyridine; 2-methoxy-1-|1-(methoxymethyl)propyl /|-4-(2,5,6-trimethyl-3-pyridinyl)-1H-imidazo(4,5-c|Ipyridine; 4-(2-chloro-4--(methylsulfonyl)phenyl|-2-ethyl -1- |/1-(methoxymethyl)propyl|)-1H-imidazo(4,5-c|pyridine; and 4-(2-chloro-4-(methylsulfonyl)phenyl|-2-methoxy-1-P1-(methoxymethyl)propyl|-1H-imidazo(4,5-c|Ipyridine; or pharmaceutically acceptable salt forms of the specified compounds

In another, more preferred embodiment, the present invention provides a novel compound of formula IB, wherein:

B' is a C3-C alkyl;

B' is substituted with 0-1 substituents selected from -СМ, -5(О)п8и5, -СОв'За, -СО»в1за, -MA aso, -

Mm(CO vza)", -"MA asom zada, dao" in, "SOM zada, 1-morpholinyl, 1-piperidinyl, 1-piperazinyl, and

Ca-in cycloalkyl, where 0-1 carbon atoms in Ca-in cycloalkyl are replaced by a group selected from -O-, -5(O)p-, -

МАЗа-, -МСОгВв-, -МСОВв- and -М5О2Во-, and where My in 1-piperazinyl is substituted by 0-1 substituents selected from В'За, СО2в/, Совы and 50285; and

IN! is also substituted with 0-3 substituents independently selected in each case from B12, B1, B1, C4-C alkyl, C1-C alkenyl, C1-C alkynyl, C1, C1, E, I, C1-4 haloalkyl , -OB'Za, -C1.2 Alkoxy-Ci-2 alkyl, and MA'Zad'va,

IZK) In another, even more preferred embodiment, the present invention provides a new compound of formula IB, wherein:

X is selected from O, 5(O)n and a bond; n equals 0, 1 or 2;

IN! is selected from cyclopropyl, cyclobutyl and cyclopentyl:

IN! is substituted 0-1 by substituents selected from -СМ, -5(О)пвы5, -СОВ1за, -502813а, and Са-в cycloalkyl, where 1 carbon atom in Саз cycloalkyl is replaced by a group selected from -О-, - 5(О)п-, -МВ'За-, -МСО2В-, -МСОВ- and -М5О2 В -;

B' is also substituted with 0-2 substituents selected independently in each case from Be, B/E, C 1 alkyl, C 2 -alkenyl, C 2 alkynyl, Bg, SI, E, CE3, CE2CE3, -OB/1Za , C1.2 alkoxy-C1-2 alkyl, and -MV'Zad'va:

IN? is aryl and is selected from phenyl and indanyl, each Be is substituted with 0-1 -OB" and 0-5 substituents independently selected in each case from C-4 alkyl, C3-e cycloalkyl, Bg, C1, E, C » haloalkyl, -SM, -5(O)pA!18, -SOV1", -MVTad'za and -SOM A ad'cha;

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from each in the case of C-4 alkyl, C3-e cycloalkyl, Bg, SI, E, SEz, -SM, -OB!", -5(O)tB!8, -SOV'", -MAad'zZa, and -SOMAad and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B'za, CO''

Owl and 50";

IN? is selected from C1-4 alkyl, C1-4 alkenyl, and C0-1 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and Cm alkoxy;

B3 and B" are independently selected in each case from H, B8, C1, E, -CM, C1-4 alkyl, C1-4 cycloalkyl, C1-4 alkoxy, MH", C1-4 alkylamino, and (C1-4 alkyl) -amino;

AND? is selected independently in each case from H, C1-6 alkyl and C3-6 cycloalkyl;

B" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl)- d'za and d'bg are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-Ci-b alkyl;

B"" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C3-4 alkyl);

The fork is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, and C3-e cycloalkyl-C1-2 alkyl;

Vo is selected from C1-6 alkyl, C1-6 haloalkyl, C1-6 oxy-C1-alkyl, C3-6 cycloalkyl, and C3-6 cycloalkyl-C1-2 alkyl;

IN? is independently selected in each case from H, C1-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl and benzyl, each phenyl or benzyl being aryl-substituted 0-3 groups selected from C -4 alkyl, C8, C1, E, C1-4 haloalkyl, C1-4 haloalkyl, C1-4 haloalkoxy, and dimethylamino;

Bza is independently selected in each case from H, C1-4 alkyl, C3-cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B", B18 and B3 are each selected from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, and C1-6 haloalkyl ; alternatively, in MV'"B"Z component B" and B'Z together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents, which are chosen from VZ, СО28!я, SOV"" and 5028;

B" and B/za are selected independently in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C3-e cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C1-4 alkyl, C3-e cycloalkyl, -OB'", B1, C1, E, C1-4 haloalkyl, -CM, -5( O)pB8, -

Sov, -СО28!", -МА'СОВ!, -МА!СО»В'В, -МВ'"В"Я, and -СОМВ VУ; and the heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl , quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide . - is cycloalkyl, Bg, SI, E, Ci-4 haloalkyl, -SM, -OB'", -5(0)tВ!8, -СОВ!", -СО28, -

ОС(О)В!В8, -МАЗСОВ', -Ш(СОВ)2, -МА!ЗСО»В'В8, "MAV, and -SOMVA" VU, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from B", СО28/!la, SOV"a and 50282,

BRIEF DESCRIPTION OF THE DRAWINGS In another, even more preferred embodiment, the present invention provides a novel compound of formula IB wherein:

X is selected from O, 5 and a bond;

IN! is substituted 0-1 by substituents selected from -СМ, -СО2813а, and Са cycloalkyl, where 0-1 carbon atoms in Са-в cycloalkyl are substituted by a group selected from -О-, -5(О)п-, and -MA13a-;

IN! also substituted with 0-2 substituents chosen independently in each case from B! B", C, alkyl,

Salt of alkenyl, C-4 alkynyl, Vg, SI, E, SEz, -ОВ'Za., -OH, -ОСН3, -ОСНеСН3, -СНГОССН», -СНаСНГОССНН», and -

Mv'zad'va:

IN! is aryl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеСН",

ОоСссНн(СНЗз)г, OSНg.СНеоСНн;", and ОСЕ", and 0-3 substituents chosen independently in each case from СНЗ,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH", and -C(O)M(CH3)"2;

IN!" is heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH» СНз, СН(СНЗз)",

СНоСНоснН;», cyclopropyl, ОСсН3, ОСН».СН3, ОСН(СН3)г, ОСН.СНесСнН», ОС», Вг, СИ, Е, СЕз, -СМ, ЗСН3, -МН», -

Mne Hz, -M(CHz)", -C(O)MH", -C(O)MNOHz, and -C(O)M(CHz)2, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from СН3, СО»2СН3, СОСН»3 and 502СН3;

B2 is selected from СН3, СНеСН3, СН(СН3)»2, and СНаСН»СН5;

B3 and B" are independently selected in each case from H, CH3, CNeCH3, CH(CH33)g, and CNaCHNoCH"; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CHbz,

СносН»з, СН(СН3)», СНСНоCH», cyclopropyl, OSН3, OSН»СН», OSН(СН3)», OSНg.СНосН», OS», Vg, SI, E, SEz, -СМ, 5СН3, 5О2СН3 . in each case from pyridyl, indolyl, benzothienyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-bZ-oxide, 2,3-dihydrobenzothienyl-b-dioxide, indolinyl, and benzoxazolin-2-one -ylu, each heteroaryl is a substituent substituted by 2-4 carbon atoms, which is chosen independently in each case from CH3, СНеCH3, СН(CH3)», СНаСНеаСН»3, cyclopropyl, OSН3, OSНегСН», осн(Сн3)», OSН ».СНосСнН», OS», Vg, SI, E, SEz, -SM, ЗСН3, 5О2СН3, -МНг, -МНОН3, -МЩ(СН3)2, -С(О)МН», -

С(О)МНеН» and -С(О)М(СНЗ3)», and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО2СН3, СОСН» and 5О»СнН.

IZt) In another, even more preferred embodiment, the present invention provides a new compound of formula IB in which:

IN! is substituted by 0-2 substituents chosen independently in each case from

СсН(СН3)г, СНСНоСН з, -(СНг)сСН3, -СНеСН», -СНеСН(СнН3), -СН-СН, -СН-С(СН3), -СНгоОоСссН», -СНаСНхОСснН 5, Е, and SEz ;

IN? is a phenyl substituted with 0-1 substituents selected from ОСН3, ОСНоСН»3, ОСН(СН3)»

ОоСНоСНосНН», and ОСЕ», and 0-2 substituents chosen independently in each case from СН3, СНоСН3З3,

СН(СНЗ3)», СНеСНоСН»», Vg, SI, E, SEz, -SM, and ZON;

IN!" is a heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazylyl, isoxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH».CH3 , СН(СНЗ3)2, СНа.СНесСнН», Osn»

ОоСНосСнН», OS», Vg, SI, E, SEz, -SM, and 5CH»z, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from CH3, СО2СН3, СОСН» and 502СН3;

B2 is selected from СН3, СНеСН», and СН(СН3)»;

BZ and B" are independently selected in each case from H and CH3; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CH3, СНеCH3, СН(CH3)", СНСНеоСнН 5», cyclopropyl, ОСН3, OSN»CHz, OSN(CHz)2, OSN.SNegsSnN», OS», Vg, SI, E, SEz, -SM, 5СНz, 5О2СНз, -МН», -

MNeH»z, -Ш(CH3)g, -"C(O)MH", -C(O)MNON"c, and -C(O)M(CH 3)", and heteroaryl is pyridyl, substituted on 2-4 carbon atoms by a substituent chosen independently in each case from СН3, СНаСН3, СН(СН3)»

SnHosSnHosnH», cyclopropyl, OSH3, OSHoCH3, OSH(CH3)g», OSH»CH2OSCH3, OS», VI, SI, ER, SEz, -SM, 5CH»vz, 5O»CH3, -MH»g, -MNOH3, -M(CH3), -"С(О)МН", -С(О)МНС Na, and -С(О)М(СН3)".

IZp| In another, even more preferred embodiment, the present invention provides a novel compound of formula IB wherein:

IN! is substituted by 0-2 substituents chosen independently in each case from B'!i, СН3, СНеСН3,

СсНН(СН3)") СНСНоснН з, -(СНг)зСН3, -"СНГОсСнН», -СНаСНГОснН;», E, and SE»; and

B!g is phenyl substituted with 0-2 substituents chosen independently in each case from SNZ,

СноснН», СН(СН3)», СНгСНоСН,», Вг, СИ, Е, СЕз, -СМ, and СН».

In an even more preferred embodiment, the present invention provides a new compound of the formula

Ir wherein: O is phenyl substituted with 2-4 substituents independently selected in each case from

CHz, CHnosH», CH(CHz)», CHNSNoCH», cyclopropyl, OSHz, OSH»CH», OSH(CHz)», OSNg.CHosnH», OS», Vg, SI, E, and SEz.

IZrI In another, even more preferred embodiment, the present invention provides a new compound of formula IB in which: O is pyridyl substituted with 2-4 substituents independently selected in each case from CH3, CH3.CH3, CH(CH3) g, СНаСНеСН», cyclopropyl, OSН3, OSНgСН3, OSН(СН3)г, OSНаСН»сСН z»,

OSE", VI, SI, E, and SEz.

In another, more preferred embodiment, the present invention provides a novel compound of formula IB, wherein:

IN! is selected from C1-10 alkyl, C1-10 alkenyl, C1-10 alkynyl, C3-6 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, and

C-4 alkoxy-C-4 alkyl;

IN! is substituted by a C3-in cycloalkyl group, where 0-1 carbon atoms in C3 cycloalkyl are substituted by a group selected from -O-, -"5(O)n-, -"МА3а-, -МСО»Б'б-, - МСОВ' and -М5О» В -;

IN! is also substituted with 0-3 substituents independently selected in each case from B'2, B", B/E, C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, Hg, Si, E, I, Si -4 haloalkyl, -OVZa, -MVZad'va, C,.2 alkoxy-C3-2 alkyl, and C3-C cycloalkyl, which is substituted 0-1 B? and in which 0-1 carbon atoms of Ca cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)»2 - group;

B is aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each B is substituted 0-1 -

ОВ" and 0-5 substituents chosen independently in each case from C1-e alkyl, C3-e cycloalkyl, Bg, SI,

E, I, C-4 haloalkyl, -SM, nitro, 5H, -5(O)0B"8, -SOV!", -OS(OV!B, -MAZaSOV!", -"ShSOV", -"MA asom adyaa, -MA'zasO»VvV, -MV!7ad'za -boMv'tad'za:

IN!? is heteroaryl and is selected from pyridyl, pyrimidinyl, triazinyl; furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3 3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, beisodioxolanyl, and benzodioxane, each heteroaryl being a 0-4 carbon substituted substituent chosen independently in each case from C1-c alkyl,

C3-e cycloalkyl, Bg, SI, E, I, C-4 haloalkyl, -CM, nitro, -"ОВ!", 5Н, -5(О)тВ!8, -"СОВ'", -ОС(О )V!V, - MAaSOV, -

M(SOV'l", -MA asom ad'za, -MAzasO»vVV, -MATad'za, and -SOMA da, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B/ !za, SO", SOV and 5028; i

B!: represents a heterocyclyl and is a saturated or partially saturated heteroaryl, each heterocyclyl being a substituted 0-4 carbon atom substituent independently selected in each case from C1-C alkyl,

Czv cycloalkyl, Bg, SI, E, I, C-4 haloalkyl, -SM, nitro, OB, 5H, -5(O)p8!5, -SOVZa, -OC(O)BB, -

MmA'zaSOovza, -M(SOVZa)", -MA asom Zadiba, MA ZasboOgviyu, -MAZadiba and -SOMNAZaVIba and each heterocyclyl is substituted on any nitrogen atom with 0-1 substituents selected from B'Za, СО",

SLEEP! and 5028", and wherein any sulfur atom is, if desired, mono- or dioxidized.

IZH In another, even more preferred embodiment, the present invention provides a novel compound of formula B wherein:

X is selected from O, 5(O)n and a bond; n equals 0, 1 or 2;

IN! is selected from C6 alkyl, C1-6 alkenyl, C6-6 alkynyl, and C3-6 cycloalkyl;

IN! is substituted by a C3-e cycloalkyl group, where 0-1 carbon atoms in Ca-e cycloalkyl are substituted by a group selected from -O-, -5(O)n-, and -MA13a-;

IN! is also substituted with 0-2 substituents independently selected in each case from B'3, VIB, C6 alkyl, C8-6 alkenyl, C8-6 alkynyl, Hg, CI, E, CE3, CE2CE3, -OB'Za, - MdVZad'vba, Si." Alkoxy-Ci-2 alkyl, and C3 cycloalkyl, which is substituted 0-1 V? and in which 0-1 carbon atoms of Sv cycloalkyl are replaced by -O-;

IN? is aryl and is selected from phenyl and indanyl, each Be is substituted with 0-1 -OB" and 0-5 substituents independently selected in each case from C-4 alkyl, C3-e cycloalkyl, Bg, C1, E, C -4 haloalkyl, -SM, -5(0),,8!8, -SOV"", -MA!7aV/za, and -SOM A ad'cha;

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from each in the case of C1-4 alkyl, C3-e cycloalkyl, Bg, SI, E, SEz, -SM, -OB"", -5(O)tv!8, -SOV!", -"MAad/cha, and - SOMBad/cha and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B'za, CO', SO'dyayu and 5028B;

B2 is selected from C1-4 alkyl, C1-4 alkenyl, and C0-4 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and Ci-4 alkoxy;

VZ and B? are chosen independently in each case from H, Bg, SI, E, -CM, C-4 alkyl, C3-e cycloalkyl, C-4 alkoxy, MH", C-" alkylamino, and (C-4" alkyl)"- amino;

IN? is selected independently in each case from H, C1-4 alkyl and C3-6 cycloalkyl;

BZ is selected from Ci-4 alkyl, Ci-2 haloalkyl, Ci-2 alkoxy-Si-2 alkyl, C3-ie cycloalkyl-Si-2 alkyl, aryl (Si-2 alkyl)-, and heteroaryl (Si-2 alkyl)-; za and D'ba are independently selected in each case from H, Ci-4 alkyl, Ci-4 haloalkyl, Ci-4 alkoxy-Ci-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-Ci-v alkyl;

B!" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-e cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl) );

The fork is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, and C3-e cycloalkyl-C1-2 alkyl;

IN! is selected from C-4 alkyl, C-2 haloalkyl, C-2 alkoxy-C-2 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-

C-2 alkyl;

IN? is independently selected in each case from H, C1-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl and benzyl, each phenyl or benzyl being aryl-substituted 0-3 groups selected from C -4 alkyl, Bg, CI, E, Cm haloalkyl, C-4 alkoxy, C-4 haloalkoxy, and dimethylamino;

Bza is independently selected in each case from H, C1-4 alkyl, C3-cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B", B!8 and B!" is selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, and C1-6 haloalkyl; alternatively, in MB'"B"Z component B" and B'Z together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from from VZ, SO28!ya, SOV"" and 5028;

B" and B/za are independently selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C1-4 alkyl, C3-e cycloalkyl, -OB'", Bg, C1, E, C1-4 haloalkyl, -CM, -5( O)pB8, -

Sov, -сО28"", -MA Sov", -MA!SO»В!8, -МВ!"ВЯ, and -"СОМВ! "IN"; and heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydropszothienyl-b5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted on 1-4 carbon atoms a substituent selected independently in each case from C3-e alkyl, C3-e cycloalkyl, Bg, CI, E, C-4 haloalkyl, -CM, -ОВ'", -5(0)тВ!8, -СОВ! ", -СО28, -

ОС(О)В!В, -МАЗСОВ', -ШЧСОВ' 2», -MA!ЗСО»В8, -MA!ВЯ, and -SOMA!В, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from B", СО28/!la, SOV"a and 50282,

IZ5| In another, even more preferred embodiment, the present invention provides a novel compound of formula IB wherein:

X is selected from O, 5 and a bond;

B' is C 1 alkyl;

IN! is a substituted C3-e alkyl, where 0-1 carbon atoms in the Ca-e cycloalkyl are substituted by a group selected from -0-, -(O)n-, and -Mvcha.-;

IN! is also substituted with 0-2 substituents selected independently in each case from B'z, VIB, Cg-6 alkyl, Cg-c alkenyl, Cg-c alkynyl, E, Cez, -OB'Za, -MV'zZad' ba, -"СН»ОСсН", -СНаСНГОСнН», and C3-in cycloalkyl, which is substituted by 0-1 CH33 and in which 0-1 carbon atoms of Ca-in cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)" - group;

IN! is aryl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеСН",

ОоСссНн(СНЗз)г, OSНg.СНеоСНн;", and ОСЕ", and 0-3 substituents chosen independently in each case from СНЗ,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH", and -C(O)M(CH3)"2;

IN!" is heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH» СНз, СН(СНЗз)",

СНоСНосН;», cyclopropyl, ОСсН3, ОСН».СН3, ОСН(СН33)г, ОСНа.СНоСсН», ОС», Вг, СИ, Е, СЕз, -СМ, ЗСН3, -МН», -

Mne Hz, -M(CHz)", -C(O)MH", -C(O)MNOHz, and -C(O)M(CHz)2, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from СН3, СО2СН3, СОСН3 and 502СН3;

IN? is selected from CH3, CH3CH3, CH(CH3)2, and СНЕСНоCH5;

B3 and B" are independently selected in each case from H, CH3, CH2CH3, CH(CH33)g, and CNaCHNoCH"; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CH33,

СносН»з, СН(СН3)», СНСНоCH», cyclopropyl, OSН3, OSН»СН», OSН(СН3)», OSНg.СНосН», OS», Vg, SI, E, SEz, -СМ, 5СН3, 5О2СН3 . in each case from pyridyl, indolyl, benzothienyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-b-dioxide, indolinyl, and benzoxazolin-2-one -yl, each heteroaryl is a substituent substituted by 2-4 carbon atoms, which is chosen independently in each case from CH3, СНеCH3, СН(СН3)», СНаСНеаСН»3, cyclopropyl, ОСН3, ОСНегСН», осн(СнН3)», ОСН ».СНосСнН», OS», VG, SI, ER, SEz, -SM, ZSNz, 5О2СНz, -МНг, -МНОНз, -М(СНз)», -С(О)МН», -

С(О)МНеН", and -С(О)М(СНЗ)", and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО»2СН3, СОСН» and 5О2СН».

IZU In another, even more preferred embodiment, the present invention provides a novel compound of formula IB, wherein:

B' is (cyclopropyl)C 1 alkyl or (cyclobutyl) C: alkyl;

IN! is substituted by 1-2 substituents chosen independently in each case from В"", ВЕ, СН3, СНеСН»З.,

Ссн(Снз)», СНСНесСН», -(СНег)зСНз, -"СНАСН", -"СНАСН(СН3), -СН-СН, -СН-С(СН3), -СНхОснН», -СНаСНгОСснНН 5, E,

CE3, cyclopropyl, CH3-cyclopropyl, cyclobutyl, CH3-cyclobutyl, cyclopentyl, CH3-cyclopentyl;

IN! is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеCH», and ОСЕ», and 0-2 substituents selected independently in each case from CH3, CH»CH3, CH(CH3)», СНаСНоCH», Wu, SI, E,

SEz, -SM, and 5СН»Зз;

IN!? is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH»CH3 , СН(СН3)г, СНаСНоСН», OSН»

ОоСНосН», ОСЕ;», Би, СИ, Е, СЕз, -СМ, and ЗСН»вз, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО2СН3, СОСН» and 502СН3 ;

B2 is selected from СН3, СНеСН», and СН(СН3)»;

B3 and B" are independently selected in each case from H and CH3; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CH3, СНеCH3?, CH(CH3)», СНСНеоСнН 5», cyclopropyl, ОСН3 .

МНеН»з, -Ш(СН3)г, -"С(О)МН", -С(О)МНОН»в, and -С(О)М(СНЗ)»; and, heteroaryl is a pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, CH3CH3, CH(CH3)».

СнН.СНсН;», cyclopropyl, ОСН3, ОСН»СН3, ОСН(СН3)2, ОСНаСНеСН», ОС», В, СИ, Е, СЕ3, -СМ, 5СН3;5О2СНаз, -МНег, -МНеН3, -М( СН3», -С(О)МН», -ФСО)МНеУ Нв, and -С(О)М(СН3)».

Изц| In another, even more preferred embodiment, the present invention provides a novel compound of formula IB wherein:

B' is (cyclopropyl)C:alkyl or (cyclobutyl)C:alkyl;

IN! is substituted by 1-2 substituents chosen independently in each case from Ba, B'!E, СН3, СНеСН»

Ссн(Снз)», СНСНесСН», -(СНег)зСНз, -"СНАСН", -"СНАСН(СН3), -СН-СН, -СН-С(СН3), -СНхОснН», -СНаСНгОСснНН 5, E,

CE", cyclopropyl, and CH3- cyclopropyl;

Va is phenyl substituted with 0-2 substituents selected independently in each case from

CH3, SnNosH», CH(CH33)», CHgSNeCH 5, Vg, SI, E, SEz, -SM, and ZON";

IN!? is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, and pyrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH2CH3, CH(CH3)" , SNESNoSN", OSNz, OSNoSN", OSE", Vg,

SI, E, SEz, -SM, and SN".

IZM| In another, even more preferred embodiment, the present invention provides a novel compound of formula IB wherein: O is phenyl substituted with 2-4 substituents independently selected in each case from CH3, CH3CH3, CH(CH3)''. CH»CNeoCH3, cyclopropyl, OSH3, OSNaCH3, OSH(CH33)»

OosSnN. NesnN;», OS», VI, SI, E, and SEz.

IZM| In another, even more preferred embodiment, the present invention provides a compound of the formula II, in which: O is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, СНеCH3, CH(CH3 )", CH»CHneCH»z, cyclopropyl, OSH»Z,

OosSNsN", OSN(SNz)", OSNSNoSnN;", OS", Vg, SI, E, and SEz.

In addition to another preferred option, the present invention introduces a new compound of the formula Is: and E zu в--

M or (Is). (4a| In another, more preferred embodiment, the present invention provides a new compound of formula Ic in which:

X is selected from O, 5(O)n and a bond; n equals 0, 1 or 2;

IN! is selected from C6 alkyl, C1-6 alkenyl, C6-6 alkynyl, and C3-6 cycloalkyl;

IN! is substituted by 0-1 substituents selected from -СМ, -5(О)п8""5, -СОВЗа, -СО2832, and C3-C cycloalkyl, where 0-1 carbon atoms in Cα cycloalkyl are substituted by a group selected with -О-, -5(О)п-, -МВ3а-, -МСО2ВЬ., -

MSOV'.- and -M5O»2Vo-;

B' is also substituted with 0-2 substituents selected independently in each case from Be, B/E, C 1 -C alkyl, C 1 -C 2 alkenyl, C 2 -C 3 alkynyl, Bg, SI, E, CEz, CE»2CEz, -OVZa , -MVZad'vba, Si. Alkoxm-Ci-2 alkyl, and C3-8 cycloalkyl, which is substituted 0-1 V? and in which 0-1 carbon atoms of Ca cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)»2 - group;

Ba is aryl and is selected from phenyl and indanyl, each B! is substituted. 0-1 -OB' and 0-5 substituents selected independently in each case from C-4 alkyl, C3-e cycloalkyl, Bg, C1, E, C-4 haloalkyl, -CM, -5(O)p8! 8, -SOV!", -"MAad/za and -SOMAadcha;

IN!? is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from each in the case of C-4 alkyl, C3-e cycloalkyl, Bg, CI, E, SEz, -SM, -OB"", -5(O)tB!8, -SOV!", -MA7ad/za, and -SOMVard 'a, and each heteroaryl with any nitrogen atom substituted with 0-1 substituents selected from B'za, СО», СОДо and 5О»n; provided that B is different from -(CHg):-4 -aryl or -(CH2)i-4-heteroaryl, where the aryl or heteroaryl group is substituted or unsubstituted;

IN? is selected from C1-1 alkyl, C1-1 alkenyl, and C1-1 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and Ci-4 alkoxy;

VAZ is selected independently in each case from H, Bg, SI, E, -CM, C1-6 alkyl, C3-e cycloalkyl, C1-4 alkoxy,

MH", C-" alkylamino, and (C-4 alkyl) 2-amino;

IN? is selected independently in each case from H, C1-4 alkyl and C3-6 cycloalkyl;

B" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl)- za and D'ba are independently selected in each case from H, Ci-4 alkyl, Ci-4 haloalkyl, Ci-4 alkoxy-Ci-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-Ci-v alkyl;

B"" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-e cycloalkyl-C1-6 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl) )-;

The fork is selected from C1-4 alkyl, C1-6 haloalkyl, C1-2 alkoxy-C1-2 alkyl, and C3-6 cycloalkyl-C1 alkyl;

Vo is selected from C1-6 alkyl, C1-6 haloalkyl, C1-6 oxy-C1-alkyl, C3-6 cycloalkyl, and C3-6 cycloalkyl-C1-2 alkyl;

IN? is independently selected in each case from H, C1-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl and benzyl, each phenyl or benzyl being aryl-substituted 0-3 groups selected from C -4 alkyl, C8, C1, E, C1-4 haloalkyl, C1-4 haloalkyl, C1-4 haloalkoxy, and dimethylamino; dza is independently selected in each case from H, C1-6 alkyl, C3-7 cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B", B!8 and B!" is selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, and C1-6 haloalkyl; alternatively, in MB'"B"Z component B" and B'Z together form 1-pyrrolidinyl, 1-morpholipyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from VZ, SO28!ya, SOV"" and 5028;

B" and B/!za are independently selected in each case from H, C1-e alkyl, C3-o cycloalkyl, C3-e cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C-4 alkyl, C3-e cycloalkyl, -OB"", Bg, CI, E, C-4 haloalkyl, -CM, -5( O)2B", -

Sov, -сО28!", -MA'SOV!, -MA!SO»Вв!8, -МВ'"ВЯ, and -СОМВ В"; and the heteroaryl is selected independently in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-b-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl, and benzodioxane, each heteroaryl is a 1-4 carbon atom substituted substituent selected independently in each case from Ci-e alkyl, C3- is cycloalkyl, Bg, SI, E, Ci-4 haloalkyl, -SM, -OB'", -5(0)tВ!8, -СОВ!", -СО28, -

ОоС(ОВ!В, -МАСОВ', -ШЧСОВ 7», -«МА!СО2В'8, «MAV,» and -"SOMA"" В, and each heteroaryl g substituted on any nitrogen atom by 0-1 substituents, which are selected from B", SO", SOV"a and 502812,

IB) In another, more preferred embodiment, the present invention provides a new compound of formula I, in which:

X is selected from O, 5 and a bond;

IN! is substituted St, alkyl;

IN! is substituted by 0-1 substituents selected from -СМ, -СО2 132, and C3-C cycloalkyl, where 0-1 carbon atoms in CА-C cycloalkyl are replaced by a group selected from -О-, -5(О)п -, and -MA13a-;

B' is also substituted with 0-2 substituents independently selected in each case from B", B", C-C alkyl, Cg-C alkenyl, Cg-C alkynyl, Bg, SI, E, CEz, -OB' For, -"Md'Zad'va, Su." alkoxy-Ci-2 alkyl, and C3-is cycloalkyl, which is substituted by 0-1 CH33 and in which 0-1 carbon atoms of Ca-in cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)" - group;

IN! is aryl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеСН»5,

ОоСссНн(СНЗз)г, OSНg.СНеоСНн;", and ОСЕ", and 0-3 substituents chosen independently in each case from СНЗ,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH", and -C(O)M(CH3)"2;

IN!" is a heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl having 0-3 carbon atoms substituted with a substituent independently selected in each case from CH3, CH» СНз, СН(СНЗз)",

СНоСНоснН;», cyclopropyl, ОСсН3, ОСН».СН3, ОСН(СН3)г, ОСН.СНесСнН», ОС», Вг, СИ, Е, СЕз, -СМ, ЗСН3, -МН», -

Mne Hz, -M(CHz)", -C(O)MH", -C(O)MNOHz, and -C(O)M(CHz)2, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from СН3, СО»2СН3, СОСН» and 5О2СН3; provided that B! is different from -(CH2)i-4-aryl or -(CH2)1i-4-heteroaryl, where the aryl or heteroaryl group is substituted or unsubstituted;

IN? selected from СН3, СНеСН3, СН(СН3)2, and СНЕСНоСН5;

BZ is chosen independently in each case from H, CH3, СНеCH3, СН(СН33)г, and СНаСНоCH»; aryl is phenyl substituted with 2-4 substituents chosen independently in each case from CH3, CNeaCH3,

СН(СН3)г, СНаСНгСН», cyclopropyl, OSН3, OSНаСН3, OSН(СН3)2, OSНgСНесН», OS», Vi, SI, E, SEz, -SM,

ЗСН3, 5О2СН3, -МНе, -МНОН3, -Ш(СН3)", -"С(О)МН», -С(О)МНеОН3, and -С(О)М(СН3)», and heteroaryl is chosen independently in each case from pyridyl, indolyl, benzothienyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-b-oxide, 2,3-dihydrobisothienyl-b-dioxide, indolinyl, and benzoxazolin-2-one -yl, each heteroaryl is a substituent substituted by 2-4 carbon atoms, which is chosen independently in each case from CH3, СНеCH3, СН(СН3)», СНаСНеаСН»3, cyclopropyl, ОСН3, ОСНегСН», осн(СнН3)», ОСН ».СНосСнН», OS», Vg, SI, E, SEz, -SM, ЗСН3, 5О2СН3, -МНг, -МНОН3, -МЩ(СН3)2, -С(О)МН», -

С(О)МНеН» and -С(О)М(СНЗ3)», and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО2СН3, СОСН» and 5О»СнН.

In another, even more preferred embodiment, the present invention provides a new compound of formula I, in which:

IN! is substituted by Si;

IN! is substituted 0-1 with substituents selected from -СМ, -СО2СН3, and -СОСНеСН;

IN! is also substituted with 0-2 substituents chosen independently in each case from Bé, B'?, CH3,

SneosnHz, cH(CHz)», СНоСНесСn»z, -(CHg)zСНi, -СНЕСН»:, -СНеЕСН(СНаз), -СНе-СН, -СН-С(СН3), -СНоССН.», -

SnHsnNoOosnH;», P, CEz, cyclopropyl, CH3-cyclopropyl, cyclobutyl, CH3-cyclobutyl, cyclopentyl, CH3-cyclopentyl;

Va is phenyl substituted with 0-1 substituents selected from ОСН3, OSР»CH», and ОСЕ», and 0-2 substituents selected independently in each case. ;", Vg, SI, E,

SEz, -SM, and 5СН»Зз;

IN!? is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CHNaCH3, CH (СН3)г, СНаСНоСН», OSN»

ОоСНосСнН», ОС», Вг, СИ, Го СЕз, -СМ, and ЗСН», and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СН3, СО2СН3, СОСН» and 5О2СН3; provided that B! is different from -(CH2)1-4-aryl or -(CH2):-"-heteroaryl, where the aryl or heteroaryl group is substituted or unsubstituted;

IN? is chosen from СН3, СНеСН», and СН(СН3)»;

VZ is selected from H and CH3; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CH3, СНеCH3, CH(CH3)», CH»oCHnoCH»3, cyclopropyl, OSH3, OSNeCH»5, osHn(CnH3)», OSH» .СНосСнН», OS», Vg, SI, E, SEz, -SM, ЗСН3, 5О2СН3, -МНг, -МНОН3, -МЩ(СН3)2, -С(О)МН», -

C(O)MNeH", and-C(O)M(CH3)2; and, heteroaryl is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, СНеCH3, CH(CH3)», СНаСНеосСнН 5», cyclopropyl, OSН3, OSН»СН3, OSН(СН3)g .

Мне Нз, -М(СНз)», -С(О)МН», -Ф(О)МНО Нз, and -С(О)М(СНз)». 44) In another and even more preferred embodiment, the present invention provides a novel compound of formula Ic wherein:

B' is a substituted (cyclopropyl)-C:1 alkyl or (cyclobutyl)-C1 alkyl;

IN! is substituted 0-1 -CM;

IN! is also substituted 0-1 by substituents chosen independently in each case of

Бе, Б'!Э, СН3, СНеСН»з, СН(СН3)г, СНеСНеСН», -(СНг)зСН3, -"СНеСН", "СНеСН(СН3З), -"СН-СН, -СНАС(СН3З) , -

СнНГОоснН», -СНСНгОСсНнН», E, SE3, cyclopropyl, and CH3-cyclopropyl;

IN! is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеCH», and ОСЕ», and 0-2 substituents selected independently in each case from CH3, CH»CH3, CH(CH3)», СНСНоCH» Vg, SI, E,

SEz, -SM, and 5СН»Зз;

IN!" is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, and pyrazolyl, each heteroaryl being a substituted 0-3 carbon atom substituent independently selected in each case from CH3, CH2CH3, CH(CH3)" , SNESNoSN", OSNz, OSNoSN", OSE", Vg,

SI, E, SEz, -SM, and SN". (4e| In another, more preferred embodiment, the present invention provides a new compound of formula I, in which:

AND! is (cyclopropyl)-Ci:alkyl or (cyclobutyl)-Ci alkyl substituted with 71 substituents independently selected in each case from B", B!" CHz, CHgCHz, CH(CHz)g, СНаСНесСН», -(CHg)zCH»Z, - сн-сСно, -СНАСН(СН3), -СН-СН, -СН-С(СН3), -СНхОсСНИ, -СНаСН2гОСН », B, CE3, cyclopropyl, and CH3-cyclopropyl;

V!g is phenyl substituted with 0-2 substituents chosen independently in each case from SNZ,

SNgSNZ, SI, E, and SEz;

IN? is a heteroaryl selected from furanyl, thienyl, and isoxazolyl, each heteroaryl being a substituted 0-2 carbon substituent, independently selected in each case from CH33,

OSN;", SI, E, and SEz. 44 In an even more preferred embodiment, the present invention provides a novel compound of formula Ic wherein:

IN! is selected from the group (cyclopropyl CH-CH3, (cyclopropyl)u CH-CHNeCH", (cyclopropyl CHNA-CH.OCH 5, (cyclopropyl)u CH-CHNaCHnoCH»z, (cyclopropyl)u CH-CH»CHnoOsnH;", ( cyclopropyl)CH, phenyl(cyclopropyl)CH, furanyl(cyclopropyl)CH, thienyl(cyclopropyl)CH, isoxazolyl(cyclopropyl)CH, (CH3-furanyl) (cyclopropyl)CH, (cyclobutylCH-CH3, (cyclobutyl)CH- СНоСН3, (cyclobutyl)уСН-СНхОсНН», (cyclobutyl)USН-СНа.СНгСНвз, (cyclobutylus Н-СНаСНхОснН 5, (cyclobutyl)2: CH, phenyl(cyclobutyl) CH, furanyl(cyclobutyl)CH, thienyl(icyclobutyl) CH , isoxazolyl(cyclobutyl)CH, and (CH3-furanyl)(cyclobutyl)CH. 49) In another, even more preferred embodiment, the present invention provides a novel compound of formula I, wherein: O is a 2-4 substituted phenyl by substituents chosen independently in each case from CH3, CH3.CH3, CH(CH3)g, CH3CH3, cyclopropyl, OSCH3, OSCH3CH3, OSCH(CH3)», OSCh3CH»CH 5»,

OSE", VI, SI, E, and SEz.

In another, more preferred embodiment, the present invention provides a new compound of the formula I, in which: O is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, СНеCH3, CH( СН3), СНаСНеаСН»з, cyclopropyl, OSН3, OSН»СН»;

OoSsNn(SNz)", OSNaSNSN", OSE:, Vg, SI, E, and SEz.

ID In another preferred embodiment, the present invention provides a novel compound of formula I, wherein said compound is selected from the group consisting of: 6-(2,4-bis(trifluoromethyl)phenyl-9-(dicyclopropylmethyl)-8-ethyl-9H-purine 6-(2-chloro-4-cyapophepyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2-chloro-4-msoxy-5-chlorophenyl)-9-(dicyclopropylmethyl)-8 -ethyl-9H-purine; 6-(2-chloro-4-mshydroxy-5-methylphenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2-chloro-4-methoxyphenyl)-8 -ethyl-9-(2-hexyl)-9H-purine; 6-(2-chloro-4-msoxyphenyl)-8-ethyl-9-(2-pentyl)-9H-purine; 6-(2-chloro- 4-msoxyphenyl)-8-ethyl-9-(3-heptyl)-9H-purine; 6-(2-chloro-4-mshydroxyphenyl)-8-ethyl-9-(3-hexyl)-9H-purine; 6 -(2-chloro-4-msoxyphenyl)-8-ethyl-9-(4-heptyl)-9H-purine; 6-(2-chloro-4-msoxyphenyl)-9-(1-cyclopropylbutyl)-8-ethyl -9H-purine; 6-(2-chloro-4-methoxyphenyl)-9-(1-DICHLOpropylpropyl)-8-ethyl-9H-purine;

6-(2-chloro-4-msoxyphenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2-chloro-4-methoxyphenyl)-9-(dicyclopropylmethyl)-8-methoxy-9H-purine; 6-(2-chloro-4-methyl-5-fluorophenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2-chloro-4-methylphenyl)-8-ethyl-9-(2-pentyl)-9H-purine; 6-(2-chloro-4-msplphenyl)-8-ethyl-9-(4-heptyl)-9H-purine;

6-(2-chloro-4-ylphenyl)-9-(1-cyclopropylbutyl)-8-ethyl-9H-purine; 6-(2-chloro-4-methylphenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2-chloro-4-irifhoromethoxyphenyl)-8-ethyl-9-(2-pentyl)-9H-purine; 6-(2-chloro-4-yl(1)uhoromethoxyphenyl)-8-ethyl-9-(3-hexyl)-9H-purine; 6-(2-chloro-4-trifluoromethoxyphenyl)-9-(1-cyclopropylbutyl)-8-ethyl-9H-purine; 6-(2-chloro-4-tri(Y)thoromethoxyphenyl)-9-(1-cyclopropyl)-8-ethyl-9H-purine; 6b-(2-chloro-4-trafluoromethoxyphenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2-chloro-4-trini)trifluoromethylphenyl)-8-ethyl-9-(1-hexyn-3-yl)-9UN-purine; 6-(2-chloro-4-tri)thoromethylphenyl)-8-ethyl-9-(1-pentyn-3-yl)-9UN-purine; 6-(2-chloro-4-trifluoromethylphenyl)-8-ethyl-9-(1-pentyn-4-yl)-9H-purine; 6-(2-chloro-4-tri(|)thoromethylphenyl)-8-ethyl-9-(1-phenyl-2-butynyl)-9H-purine;

72 6-(2-chloro-4-trifluoromethylphenyl)-8-ethyl-9-(2-heptin-4-yl)-9H-purine; 6-(2-chloro-4-fluoromethylphenyl)-8-ethyl-9-(2-hexyn-4-yl)-9H-purine; 6-(2-chloro-4-trifluoromethylphenyl)-8-ethyl-9-(2-pentyl)-9H-purine; 6-(2-chloro-4-trifluoromethylphenyl)-8-ethyl-9-(4-heptyl)-9H-purine; 6-(2-chloro-4-trifluoromethylphenyl)-8-ethyl-9-((2-furanyl)ucyclopropylmethyl|-9H-purine; 6-(2-chloro-4-trifluoromethylphenyl)-8-ethyl-9- |11-(2-furanyl)propyl|-9H-purine; 6-(2-chloro-4--trifluoromethylphenyl)-9-(1-Cyclobutylethyl)-8-ethyl-9H-purine; 6-(2-chloro -4-trifluoromethylphenyl)-9-(1-cyclopropyl-2-butynyl)-8-ethyl-9H-purine; 6-(2-chloro-4-trifluoromethylphenyl)-9-(1-cyclopropyl-2-propenyl)- 8-ethyl-9H-purine; 6-(2-chloro-4-trifluoromethylphenyl)-9-(1-cyclopropylbutyl)-8-ethyl-9H-purine; 6-(2-chloro-4-trifluoromethylphenyl)-9- (1-cyclopropylpropyl)-8-ethyl-9H-purine; 6-(2-chloro-4--rifluoromethylphenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2-chloro-4- -trifluoromethylphenyl)-9-(dicyclopropylmethyl)-8-methoxy-9H-purine; 6-(2-chloro-4--rifluoromethylphenyl)-9-1-Cyclopropyl-1-(2-thienylmethyl|-8-ethyl-9H -purine; 9-(1-cyclobutylethyl)-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine; 9-1-cyclopropyl-(3-methylisoxazol-5-yl)umethyl/|-6- (2,4-dichlorophenyl)-8-ethyl-9H-purine; 9-(1-cyclopropyl-2-butynyl)-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine; 9-(1 -cyclopropyl-2- butynyl)-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine; 9-(1-cyclopropyl-2-propenyl)-6-(2,4-dichloro-6-methylphenyl)-8-ethyl-9H-purine;

73 9-(1-cyclopropyl-2-propenyl)-6-(2,4-Dichlorophenyl)-8-ethyl-9H-purine; 9-(1-cyclopropyl-2-propynyl)-8-ethyl-6-(2-fluoromethyl-4-methoxyphenyl)-9H-purine; 9-(1-cyclopropyl-4"-fluorobenzyl)-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine; 9-(1-cyclopropylbenzyl)-6-(2,4-dichlorophenyl)-8 -ethyl-9H-purine; 9-(1-cyclopropylbenzyl)-8-ethyl-6-(2-trifluoromethyl-4-methoxyphenyl)-9H-purine; 9-(1-cyclopropylbutyl)-6-(2,4- dichlorophenyl)-8-ethyl-9H-purine; 9-(1-Cyclopropylbutyl)-8-ethyl-6-(2,4,6-trimethylphenyl)-9H-purine; 9-(1-cyclopropylbutyl)-8-ethyl -6-(2-methyl-4,5-dimethoxyphenyl)-9H-purine; 9-(1-cyclopropylbutyl)-8-ethyl-6-(2-methyl-4-chlorophenyl)-9H-purine" 9-( 1-cyclopropylbutyl)-8-ethyl-6-(2-methyl-4-methoxyphenyl)-9H-purine; 9-(1-cyclopropylbutyl)-8-ethyl-6-(2-trifluoromethyl-4-chlorophenyl)-9H-purine; 9-(1-Cyclopropylbutyl)-8-ethyl-6-(2-trifluoromethyl-4-methoxyphenyl)-9H-purine; 9-(1-cyclopropylethyl)-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine; 9-(1-cyclopropylethyl)-8-ethyl-6-(2-trifluoromethyl-4-chlorophenyl)-9H-purine; 9-(1-cyclopropylpentyl)-8-ethyl-6-(2-methyl-4-methoxyphenyl)-9H-purine; 9-(1-cyclopropylpropyl)-6-(2,4-dichloro-b-methylphenyl)-8-ethyl-9H-purine; 9-(1-Diclopropylpropyl)-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine; 9-(1-cyclopropylpropyl)-8-ethyl-6-(2,4,6-trimethylphenyl)-9H-purine; 9-(1-cyclopropylpropyl)-8-ethyl-6-(2-trifluoromethyl)-4-chlorophenyl)-9H-purine; 6-(2,4-dichloro-5-fluorophenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2,4-dichloro-5-methylphenyl)-8-ethyl-9-(2-penten-3-yl)-9UN-purine; 6-(2,4-dichloro-b-methylphenyl)-9'-dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(1-hexyn-3-yl)-9UN-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(1-methoxycarbonylpropyl)-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(1-phenyl-2-butynyl)-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(2-heptin-4-yl)-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(2-hexyl)-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(2-hexyn-4-yl)-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(2-penten-3-yl)-9H-purine; 6-(2,4-dichlorophyll)-8-ethyl-9-(2-pentyl)-9H-purine; 6-(2,4-Dichlorophyll)-8-ethyl-9-(3-heptyl)-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(3-hexyl)-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(3-pentyl)-9H-purine; 6-(2,4-dichlorophenyl)-8-ethyl-9-(4-heptyl)-9H-purine; 6-(2,4-dichlorophnyl)-8-ethyl-9-|11-(2-methylcyclopropyl)ethyl|-9H-purine;

6-(2,4-dichlorophenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2,4-dichlorophenyl)-9-(dicyclopropylmethyl)-8-ethyl-9H-purine; 6-(2,4-dichlorophosphyl)-9-(dicyclopropylmethyl)-8-methoxy-9H-purine; 6-(2,4-dichlorophosphyl)-9-(diphenylmethyl)-8-ethyl-9H-purine; 9-(dicyclopropylmethyl)-6-(2,4-dimethylphenyl)-8-ethyl-9H-purine; 9-(dicyclopropylmethyl)-6-(2,4-dimethylphenyl)-8-ethyl-9H-purine; 9-(dicyclopropylmethyl)-6-(2,4-dimethoxypyridin-3-yl)-8-methoxy-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2,4,5-trichlorophenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-methoxy-4-trifluoromethylphenyl)-9H-purine; 9-(Dicyclopropylmethyl)-8-ethyl-6-(2-methyl-4,5-dimethoxyphenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-methyl-4chlorophenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-methyl-4-dimethylaminophenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-methyl-4-methoxy-5-chlorophenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-methyl-4-methoxy-5-fluorophenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-chloro-4-methoxy-5-fluorophenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-methyl-4-methoxyphenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-fluoromethyl-4-chlorophenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-trifluoromethyl-4-methoxyphenyl)-9H-purine; 9-(dicyclopropylmethyl)-8-ethyl-6-(2-trifluoromethyl-4-propyloxyphenyl)-9H-purine; 6-(2,6-dimethoxypyridin-3-yl)-8-ethyl-9-(2-pentyl)-9H-purine; 6-(2,4-dimethylphenyl)-8-ethyl-9-(2-pentyl)-9H-purine; 8-ethyl-6-(2-methyl-4,5-dimethoxyphenyl)-9-(2-pentyl)-9H-purine; 8-ethyl-6-(2-methyl-4,5-dimethoxyphenyl)-9-(3-pentyl)-9H-purine; 8-ethyl-9-(1-hexeyl-3-yl)-6-(2-methyl-4,5-dimethoxyphenyl)-9H-purine; 8-ethyl-9-(1-hexep-3-yl)-6-(2-trifluoromethyl-4-methoxyphenyl)-9H-purine; 8-ethyl-9-(2-hexyl)-6-(2-fluoromethyl-4-methoxyphenyl)-9H-purine; 8-ethyl-9-(2-pyridine)-6-(2-trifluoromethyl-4-methoxyphenyl)-9H-purine; 8-ethyl-9-(3-hexpl)-6-(2-methyl-4-methoxyphenyl)-9H-purine; 8-ethyl-9-(3-hexyl)-6-(2-trifluoromethyl-4-methoxyphenyl)-9H-purine; 8-ethyl-9-(3-pentyl)-6-(2-fluoromethyl-4-chlorophenyl)-9H-purine; 8-ethyl-9-(4-heptyl)-6-(2-methyl-4-chlorophenyl)-9H-purine; 8-ethyl-9-(4-heptyl)-6-(2-methyl-4-methoxyphenyl)-9H-purine; 8-ethyl-9-(4-phenyl)-6-(2-trifluoromethyl-4-chlorophenyl)-9H-purine; 8-ethyl-9-(4-heptyl)-6-(2-fluoromethyl-4-methoxyphenyl)-9H-purine; and 9-(dicyclopropylmethyl)-8-ethyl-6-(2-methyl-b-methoxy) -3-pyridyl)-9H-purine; or pharmaceutically acceptable salt forms of the specified compounds.

In another, more preferred embodiment, the present invention provides a new compound of formula I, wherein:

IN! is C3-C cycloalkyl;

IN! is substituted by 0-1 substituents selected from -СМ, -5(О)пв8!и9 -СОв81За -б0О28за, -МВзасСО vda, -

M(SOVZa)", MA'zaSOMA zada'sa, -MAzasOg V ASOM zada i, morpholinyl, 1-piperidinyl, 1-piperazinyl, and

Ca-in cycloalkyl, where 0-1 carbon atoms in Ca-in cycloalkyl are replaced by a group selected from -O-, -5(O)p-, -

MAza-, -МСО2В-, -МСОВ'- and -М5О2В9-, and where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from В!За, СО», СО and 50285: and D! is also substituted with 0-3 substituents independently selected in each case from B"", B", B/e, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, HG, SI, E, I, C-4 haloalkyl, -OvB'za, -C1-2 alkoxy-Ci-6 alkyl, and MA 'Zad'va,

IC) In another, even more preferred embodiment, the present invention provides a new compound of formula IC, wherein:

X is selected from O, 5(O)n and a bond; n equals 0, 1 or 2;

IN! is selected from cyclopropyl, cyclobutyl and cyclopentyl:

B is a substituted 0-1 substituents selected from -СМ, -5(О)пВ"5, -СОВЗа, -СО2Н8132, and C1 cycloalkyl, where 1 carbon atom in the Са-в cycloalkyl is substituted by a group selected from -О -, -5(O)p-, -MA Za., -МСО»2В'о., -МСОВ!- and -М5О2 В.

IN! is also substituted with 0-2 substituents independently selected in each case from B'z, VIB, C6 alkyl, Cg-c alkenyl, C0-c alkynyl, Bg, Si, E, CEz, CE2CEz, -'OVZa, Si. Alkoxy-Si alkyl, and -MAZad'va;

Ba is aryl and is selected from phenyl and indanyl, each H1 is substituted with 0-1 -OB" and 0-5 substituents independently selected in each case from C1-4 alkyl, C3-e cycloalkyl, H, C , E, C-4 haloalkyl, -SM, -5(O)p8!8, -SOV!", -"MAadicha, and -SOMATad'cha;

IN!? is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and aipdacholyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from in each case from C-4 alkyl, C3-e cycloalkyl, Bg SI E CE, -SM, -OB"", -5(O)tB"8 -SOB', -MAadza and -SOMA72B/a, and each heteroaryl' l with substituted on any nitrogen atom 0-1 substituents selected from В"za, СО2В5, СОВо and 5028В;

IN? is selected from C-4 alkyl, C1-4 alkenyl, and C2-4 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and C1-6 alkoxy;

VAZ is selected independently in each case from H, B", CI, E, -CM, Ci-" alkyl, C3 cycloalkyl, Ci-4 alkoxy,

MH", C-a" alkylamino, and (C-4 alkyl)"-amino;

AND? is selected independently in each case from H, C1-6 alkyl and C3-6 cycloalkyl;

BZ is selected from C-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, tagheteroaryl (C1-2 alkyl)-; d'a and d'bg are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl ;

B"" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-ie cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, tagheteroaryl (C1-2 alkyl) ;

Ba is selected from C 1-4 alkyl, C 1-2 haloalkyl, C 1-4 alkoxy-C 1-2 alkyl, and C 3-e cycloalkyl-C 1-2 alkyl;

Wb is selected from Ci-4 alkyl, Ci-haloalkyl, Ci-alkoxy-Ci-2 alkyl, C3-e cycloalkyl, and C3-6 cycloalkyl-Ci-2" alkyl;

B" is independently selected in each case from H, C-4 alkyl, C3-7t cycloalkyl, C3-e cycloalkyl-C1-4, alkyl, phenyl and benzyl, each phenyl or benzyl being substituted on the aryl component by 0-3 groups, selected from Ci-4 alkyl, Hg, Ci, E, Ci-4 haloalkyl, Ci-4 alkoxy, Ci-4 haloalkyl, and dimethylamino; dza is independently selected in each case from H, Ci-4 alkyl, C3-7 cycloalkyl , and C3-is cycloalkyl-C1-6 alkyl;

A", B3 and B!? are independently selected in each case from H, C1-6 alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, and C1-4 haloalkyl ; as an alternative, in MA!"В" With component B" and

B!Z together form 1-pyrrolidinyl, 1-morpholsilyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from BZ, СО2Б!Я, СОВ": and 5028";

Ba and B/z are selected independently in each case from H, C1-e alkyl, C3-10 cycloalkyl, C3-e cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C-4 alkyl, C3-e cycloalkyl, -OB"", B, CI, E, C-4 haloalkyl, -CM, -5( O)2B", -

SON, -СО28!", -MAZSOV', -MA!?СО»2В!8, -MAVYA, and -"SOMVA" В"; and heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furapyl, quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, bepufuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, tetrazolyl, , indazolyl, 2,3-dihydrobenzofuranyl . atoms with a substituent selected independently in each case from Ci-e alkyl, C3-e cycloalkyl, Bg, Si, E, Ci-4 haloalkyl, -СМ, -ОВ'", -5(О)тВ"8, -СОВ ', -СО2В, -

ОоС(ОВ!В, -MASOV!", -Щ(СОВ'", -MA"СО»В!В8, "MAV, and -"SOMA"" B, and each heteroaryl with substituted on any nitrogen atom 0 -1 by substituents selected from B", СО2vla, СОВ'a and 50288,

In another, even more preferred embodiment, the present invention provides a new compound of formula I, in which:

X is selected from O, 5 and a bond;

IN! is substituted with 0-1 substituents selected from -СМ, -СО2В8з2, and Слв cycloalkyl, where 0-1 carbon atoms in Са-в cycloalkyl are replaced by a group selected from -О-, -(О)н-, and - MACHA;

B' is also substituted with 0-2 substituents selected independently in each case from Be, B/E, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, Bg, Si, E, Ce3, -OB/Za, - "OH, -"OSN", -"OSNesSnN»z, -СНgОСснН», -СНаСНgОСснН»5, and-

Mv'Zad'va,

Va is aryl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеСН»

ОоСссНн(СНЗз)г, OSНg.СНеоСНн;", and ОСЕ", and 0-3 substituents chosen independently in each case from СНЗ,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH", and -C(O)M(CH3)"2;

IN!? is a heteroaryl | is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a 0-3 carbon substituted substituent independently selected in each case from CH3, CH»CH3, CH( SNZz)",

СНоСНоснН;», cyclopropyl, ОСсНз, ОСН».СН», ОСН(СН3)г, ОСН.СНеСснН», ОС», Вг, СИ, Е, СЕз, -СМ, ЗСНз, -МН», -

Mne Hz, -M(CHz)", -C(O)MH", -C(O)MNOHz, and -C(O)M(CHz)2, and each heteroaryl is substituted on any nitrogen atom 0- 1 by substituents selected from СН3, СО2СН3, СОСН» and 502СН3;

IN? selected from СН3, СНеСН3, СН(СН3)»2, and СНЕСНоСН5;

ВЗ is selected from Н, СНЗ, СНеСН3, СН(СН3)г, and СНаСНосСН»; aryl is phenyl substituted with 2-4 substituents chosen independently in each case from CH3, СНеCH3, CH(CH3)», СННеоСнН5», cyclopropyl, ОСН3, ОСН»CH3, ОСН(СН3)2, ОСН.СНегсСнН» , OS», Vi, SI, E, SEz, -SM, 5СНz, 5О2СНz, -МН», -

Mne H3, -M(CH3)", -C(O)MH", -C(O)MNON»3, and -C(O)M(CnH3)", and, the heteroaryl is substituted independently in each case from pyridyl, indolyl, benzothienyl, 2,3-dihydrobepufuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-β-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, and benzoxazolin-2-on-yl, each heteroaryl is substituted by 2-4 carbon atoms, a substituent chosen independently in each case from СНЖ, СН»СН»з, СН(СНАСЗ)г, СНаСНосСН», cyclopropyl, OSН3, OSН»СН3, OSН(СН33)2, OSНаСНосН», OS", Vg, SI,

E, SE3, -SM, ZCH3, ZO»CH3, -MNg, -MNON3, -M(CH3)», -С(О)МН»г, -С(О)МНОН», and -С(О)М (CH3)2, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from CH3, СО2CH3, СОЧН3, and 5ОоCH». (4t) In another and even more preferred embodiment, the present invention provides a new compound of formula I in which:

IN! is substituted by 0-2 substituents chosen independently in each case from B!8., B, СН3, СНеСН»3,

Ссн(Снз)», СНСНесСН», -(СНег)зСНз, -"СНАСН", -"СНАСН(СН3), -СН-СН, -СН-С(СН3), -СНхОснН», -СНаСНгОСснНН 5, E, and CE";

IN? is a phenyl substituted with 0-1 substituents selected from ОСН3, ОСНоСН»3, ОСН(СН3)»

ОоСНоСНосНН», and ОСЕ», and 0-2 substituents chosen independently in each case from СН3, СНоСН3З3,

СН(СНЗ3)», СНеСНоСН»», Vg, SI, E, SEz, -SM, and ZON;

IN!" is a heteroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, CH»CH3, СН(СН3)г, СНаСНоСН», OSН»

ОоСНосСнН», OS», Vg, SI, E, SEz, -SM, and ZON», and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from CH3, СО2СН3, СОСН» and 502СН3;

B2 is selected from СН3, СНеСН», and СН(СН3)»;

VZ is selected from H and CH3; aryl is a phenyl substituted with 2-4 substituents chosen independently in each case from CH3, СНеCH3, CH(CH3)», СН»оСНоСН»3, cyclopropyl, ОСН3, ОСНеCH»5,

ОосНн(СнНз)», OSN».СНосСнН», ОС», Г, СИ, Е, SEз, -СМ, ЗСНз, 5О2СНз, -МНг, -МНОНз, -МЩ(СН3)2, -С(О)МН» , -

С(О)МНеОН", and -С(О)М(СН3)г, and heteroaryl is a pyridyl substituted on 2-4 carbon atoms by a substituent chosen independently in each case from СН3, СНеСН3, СН(СН3) », СНаСНеосСнН 5», cyclopropyl, OSН3, OSН»СН3, OSН(СН3)2, OSН.СНегсСнН», OS», Вг, СИ, Е, СЕз, -СМ, 5СН3, 5О2СН3, -МН», -

МНеН», -М(СН3)», -С(О)МН», -Ф(О)МНО Н3, and -С(О)М(СН3)». (4p)| In another, even more preferred embodiment, the present invention provides a novel compound of formula I, wherein:

IN! is substituted by 0-2 substituents chosen independently in each case from VZ, СН3, СНеСН3,

СсНн(СнЗз)», СНСНосН », -«(СНг)зСН3, -«СНгОСсН», -СНгСНгОснН», E, and SE»; and

B!g is phenyl substituted with 0-2 substituents chosen independently in each case from SNZ,

СноснН», СН(СН3)», СНгСНоСН,», Вг, СИ, Е, СЕз, -СМ, and СН».

I4oi| In an even more preferred variant, the present invention introduces a new compound of the formula

Is wherein: O is phenyl substituted with 2-4 substituents independently selected in each case from

CHz, CHnosH», CH(CHz)», CHNSNoCH», cyclopropyl, OSHz, OSH»CH», OSH(CHz)», OSNg.CHosnH», OS», Vg, SI, E, and SEz.

I4ri| In another, even more preferred embodiment, the present invention provides a compound of the formula Is wherein: O is pyridine substituted with 2-4 substituents independently selected in each case from CH3, CH3.CH3, CH(CH3)g .

OSE;", Vg, SI, E, and SEz. (44) In another, more preferred embodiment, the present invention provides a novel compound of formula I, wherein:

B' is selected from C1-10 alkyl, C1-10 alkenyl, C1-10 alkynyl, C3-1 cycloalkyl, C3-10 cycloalkyl-C1-6, alkyl and

C-4 alkoxy-C-4 alkyl;

IN! is substituted by a C3-C cycloalkyl group, where 0-1 carbon atoms in C1 cycloalkyl are replaced by a group selected from -О-, -5(О)п-, -МА1За-, -МСО»вВ/1в-, -МСОВ "B- and -MZO»2Во-;

IN! is also substituted with 0-3 substituents independently selected in each case from B12, B1, B1, C4-C alkyl, C1-C alkenyl, C1-C alkynyl, Vy, C1, E, I, C1-4 haloalkyl , -OV'Za, -MVZad'va, S.» alkoxy-Ci-2 alkyl, and C3- in cycloalkyl, which is substituted by 0-1 BZ and in which 0-1 carbon atoms of C1-cycloalkyl are replaced by -O-; provided that B! is different from the cyclohexyl - (CHg)" - group;

B!g is aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each B" is substituted 0-1 -

ОВ" and 0-5 substituents selected independently in each case from C1-e alkyl, C3-c, cycloalkyl, Bg, CI,

E, I, C-4 haloalkyl, -SM, nitro, 5H, -5(O)0B"8, -SOV!", -OS(OV!B, -MAZaSOV!", -"ShSOV", -"MA asom adyaa, -MA!5or2VV, -MAad'za, and -SOoMAad'za;

IN!" is and stearoaryl and is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolimyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofurapyl, beipothiepyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, ipadazolyl, 2 . 0-4 carbon atoms by a substituent selected independently in each case from C1-in alkyl,

C3-e cpcloalkyl, Vg, SI, E, I, Ci-4 haloalkyl, -SM, nitro, -OB!", 5H, -B(O)tv!?, -SOV'", -OS(O)B !8, - MA RaSOV, -

M(СОВ2, -MAzaSOMAtad'za, -MAvasboO»vB, "MV Tad'za, and -SOMAad/cha, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B'za, SO", SOV" and 5028"; i

B!: represents a heterocyclyl and is a saturated or partially saturated heteroaryl, each heterocyclyl being a substituted 0-4 carbon atom substituent independently selected in each case from C1-6 alkyl,

C3-e cycloalkyl, VI, SI, E, I, C4 haloalkyl, -CM, nitro, ОВ", 5Н, -5(О)О8», -СОВЗа, -ОС(О)Вю, - mA'aSbOvVa - СОвВза)», -MA'zasOMAZadiba MA IzasboOvi -MATZadi, and -SOMAZadye, and each heterocyclyl is substituted on any nitrogen atom with 0-1 substituents selected from В!За, СО2В/В,

Sov and 50285, and where any sulfur atom is, if desired, mono- or dioxidized.

I4g| In another, even more preferred embodiment, the present invention provides a novel compound of formula I, wherein:

X is selected from O, 5(O)n and a bond; n equals 0, 1 or 2;

IN! selected from C-C alkyl, C-C alkenyl, C-C alkynyl, and C-C cycloalkyl;

IN! is a substituted C3-.e, cycloalkyl group, where 0-1 carbon atoms in the C1 cycloalkyl are substituted by a group selected from -O-, -5(O)p-, and -MV"Za-;

B' is also substituted with 0-2 substituents selected independently in each case from Be, B'E, C 16 alkyl, C 1 -C alkenyl, C 2 -C alkynyl, Bg, SI, E, CEz, CE2CEz, -OVZa, - Mdzad'va, Si." Alkoxy-Ci-2 alkyl, and C3 cycloalkyl, which is substituted 0-1 V? and in which 0-1 carbon atoms of Sv cycloalkyl are replaced by -O-;

IN? is aryl and is selected from phenyl and indanyl, each B! is substituted by 0-1 -OB'" and 0-5 substituents selected independently in each case from C-4 alkyl, C3-e cycloalkyl, Bg, CI, E, C-4 haloalkyl, -CM, -5(O )pA8!18, -"SOV -MVTad'za, and -"SOMAad'cha;

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, furanyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a substituted 0-4 carbon substituent independently selected from each in the case of C-4 alkyl, C3-e cycloalkyl, Bg, SI, E, SEz, -SM, -OB"", -5(O)twA!8, -SOV"", -MA!7ad/1za, and -СОМА7ад/яа, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B'za, СО»

Owl and 50";

B2 is selected from C1-4 alkyl, C1-4 alkenyl, and C1-4 alkynyl and is substituted with 0-1 substituents selected from -CM, OH, CI, E, and C1-4 alkoxy;

BZ is selected from H, Bg, SI, E, -CM, C-4 alkyl, C3-e cycloalkyl, C-4 alkoxy, MH", C-" alkylamino, and (Ci-alkyl)C"-amino;

AND? is selected independently in each case from H, C1-6 alkyl and C3-6 cycloalkyl;

BZ is selected from C1-6 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-e cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl)-;

Visa and Viva are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B"" is selected from C1-4 alkyl, C1-2 haloalkyl, C1-2 alkoxy-C1-2 alkyl, C3-e cycloalkyl-C1-2 alkyl, aryl (C1-2 alkyl)-, and heteroaryl (C1-2 alkyl) );

Ba is selected from C 1-4 alkyl, C 1-2 haloalkyl, C 1-4 alkoxy-C 1-2 alkyl, and C 3-e cycloalkyl-C 1-2 alkyl;

Wb is selected from Ci-4 alkyl, Ci-haloalkyl, Ci-alkoxy-Ci-2 alkyl, C3-e cycloalkyl, and C3-6 cycloalkyl-Ci-2" alkyl;

B" is independently selected in each case from H, C-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl and benzyl, each phenyl or benzyl being substituted in the aryl component! 0-3 groups , selected from C-4 alkyl, Vg, C-4, E, C-4 haloalkyl,

C1-4Alkoxy, C1-4haloAlkoxy, and dimethylamino;

Bza is independently selected in each case from H, C1-4 alkyl, C3-cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B, Bb and B'? are independently selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-2 alkyl, and C1-4 haloalkyl; as an alternative, in MA!""В"With component AB" and

IN!" together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from ВЗ, СО2В!Я, СОВ": and 5028";

Va and v/!za are selected independently in each case from H, C1-e alkyl, C3-10 cycloalkyl, C3-e cycloalkyl-

Siv alkyl and Si. haloalkyl; aryl is phenyl substituted with 1-4 substituents independently selected in each case from C-4 alkyl, C3-e cycloalkyl, -OB'", Vu, CI, E, C-4 haloalkyl, -CM, -5( O)pB8, -

SON!" -СО2В!", -MASOV!, -MA!ZSO»В!В, -MA!VYA, and -SOMV! B" and heteroaryl is prepared independently in each case from pyridyl, pyrimidinyl, triazinyl, furapyl, quinolinyl, isoquinolinyl, thienyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, bepzofurapyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, tetrazolyl, ipadacholide, 2,3 -dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted by 1- 4 carbon atoms with a substituent selected independently in each case from C-e alkyl, C 3-e cycloalkyl, Bg, SI, E, C-4 haloalkyl, -СМ, -ОВ'", -5(О)тВ"8, -СОВ', -СО2В, -

ОоС(ОВ!В, -MASOV!", -Щ(СОВ'", -MA"СО»В!В8, "MAV, and -"SOMA"" B, and each heteroaryl is substituted on any nitrogen atom 0 -1 with substituents selected from B", СО2va, ОВЯ and 50288, (45) In another embodiment, which is even more preferred, the present invention introduces a new compound of the formula Is, in which:

X is selected and 5 O, 5 and connection;

B' is a C-C alkyl;

A» is a substituted C3-e alkyl, where 0-1 carbon atoms in Ca--in cycloalkyl are replaced by a group selected from -0-, -5(O)n-, and -MA13a-;

B' is also substituted with 0-2 substituents selected independently in each case from Be, B'E, C 16 alkyl, Cg-c alkenyl, Co-c alkynyl, E, CEz, -OB1Za, -MVZad'vda, "NgOSN », -СНаСНГОССнН», and C3-is cycloalkyl, which is substituted by 0-1 CH3 and in which 0-1 carbon atoms of Cl-in cycloalkyl are replaced by -O-; provided that B' is substituted by the cyclohexyl - (CHg)" - group;

Ba is arpl and is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеCH, осНн(СН3)2, ОСНг.СНгСнН 5", and ОСЕ:", and 0-3 substituents independently selected in each in the case of SNS,

SnosnH»z, CH(CHZz)g, СNaСНesCH», cyclopropyl, Vg, SI, E, SEz, -SM, 5CHz, -MNeg, -MNOHz, -M(CHz)2, -C(O)MH», -

C(O)MNeH", and -C(O)M(CH3)2;

IN!? is ivoroaryl and is selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, iskeazolyl, pyrazolyl, triazolyl, tetrazolyl, and indazolyl, each heteroaryl being a 0-3 carbon substituted substituent independently selected in each case from CH3, CH» СНз, СН(СНЗз)",

СНоСНоснН;», cyclopropyl, ОСсНз, ОСН».СН3, ОСН(СН3)г, ОСН.СНесСнН», ОС», В, СИ, Е, СЕз, -СМ, ЗСН3, -МН», -

Mne Hz, -M(CH3)2, -"F(O)MH", -"F(O)MNOH3", and -"C(O)M(CnH3)", and each heteroaryl is substituted at any a and nitrogen atoms with 0-1 substituents selected from СН3, СО2СН3, СОСН»3 and 502СН3;

B2 is selected from СН3, СНеСН3, СН(СН3)»2, and СНаСН»СН5;

BZ is selected from H, CH3, СНаСН3, СН(СН3)г, and СНаСНеСН»3; aryl is phenyl substituted with 2-4 substituents independently selected in each case from CH3, СНеCH3, CH(CH3)», СННеоСнН 5», cyclopropyl, ОСН3, ОСН»CH3, ОСН(CH3)», ОСН»СНеCH », OS», Vg, SI, E, SEz, -SM, 5СНz, 5О2СНz, -МН», -

MHC H»z, -M(CHz)2, -C(O)MH»g, -C(O)MNOHz, and -C(O)M(CHz)», and heteroaryl is synthesized independently in each case from pyridyl , indolyl, benzothienyl, 2,3-dihydrobep ufuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-b5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indoliyl, and benzoxazolin-2-on-yl, each heteroaryl is a substituted 2-4 carbon" substituent, chosen independently in each case from CH3, CH2CH3, CH(CH3)g, СНаСНоCH", cyclopropyl, OSН3, OSНоCH3, OSН(CH3)», ОНхСНесCH», ОСЕ;" ,

Hg, SI, E, SEz, -SM, 5CHz, 5О2CHz, -MNeg, -MNOHz, -M(CHz)", -С(О)МН»г, -С(О)МНОН»з, and -С( О)М(СНЗ)", and each heteroaryl is substituted on any a and оth nitrogen with 0-1 substituents selected from СН3, СО2СН3, СОСН3 and 5ОоСН".

In another, more preferred embodiment, the present invention provides a novel compound of formula I, wherein:

B' is (cyclopropyl)C alkyl or (cyclobutyl)C: alkyl;

IN! is substituted by 1-2 substituents chosen independently in each case from

СсНн(СнНЗз)», СНСНосН», -««(СНг)зСН3, -СНАСН», -СНАСН(СнНз), -СНеАСН, -«СНАС(СН3), -«СНгОсСнН», -«СнгСНгОснНН 5, E,

CEz, cyclopropyl, CH3-cyclopropyl, cnclobutyl, CH3-cyclobutyl, cyclopentyl, CH3-cyclopentyl;

B!g is phenyl substituted with 0-1 substituents selected from ОСН3, ОСНеCH», and ОСЕ», and 0-2 substituents selected independently in each case from CH3, CH»CH3, CH(CH3)» SNaSNoSN", Wu, SI, E,

SEz, -SM, and 5СН»Зз;

IN!" is an isisoaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, oxazolyl, pyrazolyl, triazolyl, and tetrazolyl, each heteroaryl being a substituted 0-3 carbon substituent independently selected in each case from CH3, СНаCH3, СН(СН3)г, СНаСНоСН», OSН»

ОоСНосСнН», OS», Vg, SI, E, SEz, -SM, and 5СН»z, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from СИ з, СО»2СН3, СОСН» with and 502СНз;

IN? is chosen from СН3, СНеСН», and СН(СН3)»;

VAZ is selected from H and SN"; 88 aryl is phenyl substituted with 2-4 substituents independently selected in each case from

CHz, CHnosH», CH(CHz)», CHNSNoCH», cyclopropyl, OSHz, OSH»CH», OSH(CHz)», OSNg.CHosnH», OS», Wu, SI, E,

СЕз, -СМ, 5СНз, 5О2СНз, -МН»г, -МНОНз, -М(СНз)», -С(О)МН», -С(О)МНО Нв, and -С(О)М(СНЗ) "; and, heteroaryl is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, СНа.СН3, СН(СН3)», СНаСНеСН»3, cyclopropyl. ОСН3, ОСНаСН3, ОСН(СН3)г, ОСНаСН»сСН»»,

OS», Vg, SI, E, SEz, -SM, 5СН3, 5О2СН3, -МН», -МНОН3, -М(СН3)2, -С(О)МН», -С(О)МНОН3, and-С (ОМ(СНз)».

I4C| In another, even more preferred embodiment, the present invention provides a novel compound of formula I, wherein:

B' is (cyclopropyl)C:alkyl or (cyclobutyl)C:alkyl;

IN! is substituted by 1-2 substituents chosen independently in each case from

Is, СН(СН3)», СНеСНосСН», -(СНг)зСН3, -"СНеСН", -СНАСН(СН3), -СНеСН, -СН-С(СН3), -СНоСНосНН», -"СНаСНГОоСснНН»,

E, CE3, cyclopropyl, and CH3-cyclopropyl;

B!g is phenyl substituted with 0-2 substituents chosen independently in each case from SNZz,

SnosnH», CH(CH3)», CHgSNoCH 5, Vi, SI, E, SEz, -SM, and 5CHZ;

IN!" is a heteroaryl selected from furanyl, thienyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, and pyrazolyl, each heteroaryl being a 0-3 carbon substituted substituent independently selected in each case from CH3, CH3CH3, CH(CH3)" , СНеСНосСН»з, OSНоСН», ОСЕ», Wu, SI, E,

SEz, -SM, and 5SN".

IIM| In another, even more preferred embodiment, the present invention provides a novel compound of formula I in which: O is phenyl substituted with 2-4 substituents independently selected in each case from CH3, CH»CH3, CH(CH3) », СНаСНесНС», cyclopropyl, OSН3, OSНоСН»з, OSН(СН33)», OSНоСН»,

OSE", VI, SI, E, and SEz.

IImM| In another variant, which is even more preferred, the present invention introduces a new compound of the formula I, in which: ХО is pyridyl substituted on 2-4 carbon atoms by a substituent selected independently in each case from CH3, CHNeCH3, CH(CH3 )", CH»CHneCH»z, cyclopropyl, OSH»Z,

OosSNsN", OSN(SNz)", OSNSNoSnN;", OS", Vg, SI, E, and SEz.

IBI In the third variant, this invention introduces a new pharmaceutical composition, which includes: a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of formula (1): incl. 3

M A Kk vi-k-u Her m

M 2 9 (or its stereoisomer or a pharmaceutically acceptable salt form, in which:

A represents M or C-B";

B is M or C-B8; provided that at least one of the groups A and B is M; p is an aryl or heteroaryl group attached through an unsaturated carbon atom;

X is selected from SN-VU, M-VE, O, 5(O)n and connection; n equals 0, 1 or 2;

B' is selected from C1-10 alkyl, C10-10 alkenyl, C1-10 alkynyl, C3-3 cycloalkyl, C3-e cycloalkyl-C1-6, alkyl,

Ca alkoxy-Ci-4 alkyl, -502-Ci1-10 alkyl, -502-B"", and -502-B"E;

IN! is substituted with 0-1 substituents selected from -СМ, -5(О)п8и5, -СОВзЗа, -СО28за, -МА'заСОВза, -

M(SO Ba)", -MAzaSOM V Zad'va, "MA zabOgv, SOM Zad'sa, 1-morpholipyl, 1-piperidinyl, 1-piperazinyl, and

C3-C cycloalkyl, where 0-1 carbon atoms in Ca-C cycloalkyl are replaced by a group selected from -O-, -5(O)n-, -

МАЗа-, -МСОгВв-, -МСОВв- and -М5О2В5-, and where My in 1-piperazinyl is substituted 0-1 substituents selected from Ba, СО289, СОВЯ and 50289;

IN! is also substituted with 0-3 substituents independently selected in each case from B", VI, Die, C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, Hg, C1-6, E, I, C1-4 haloalkyl . ! is different from: (a) a 3-cyclopropyl-3-methoxypropyl group; (b) an unsubstituted -(alkoxy)methyl group; and (c) a 1-hydroxyalkyl group; also provided that when the 1 alkyl is substituted by OH, carbon atom adjacent to the M ring, with different from

Sn";

B": represents aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each B" is substituted with 0-5 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, B6, C1-6, E . ShCSOV 7", -MAaOMA where, -

Mmv'aSO»VvV, -MA'Tad'za, and -soMv'tad'za:

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, ichochiolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothiepyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, heiracholyl, indazolyl, 2,3 - dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-b-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted by 0- 4 carbon atoms by a substituent selected independently in each case from C1-in alkyl,

C3-e cycloalkyl, Bg, SI, E, I, C-4 haloalkyl, -CM, nitro, -"ОВ!", 5Н, -5(О)тВ!8, -"СОВ'", -ОС(О )V!V, - MAaSOV, -

M(SOV'l), -MA asom ad'za, -MAZasO»vVV, -MATad'za, and -SOMAed'a, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B for, SO, SOV'Ta 5028175;

IN! is a heterocyclyl and is a saturated or partially saturated heteroaryl, each heterocyclide being a 0-4 carbon substituted substituent independently selected in each case from C-C alkyl,

Czv cycloalkyl, VH, SI, E, I, C-4 haloalkyl, -SM, nitro, ОВ'За, 5Н, -5(О)п8!й9, -СОВЗа, OS(О)ВВ, -

MmA"asOov'za, "CO VZa)", mmAasOMAZad'sa, "MA zaSOgv, -MVZadisa, and -"SOMA zada, and each heterocyclyl is substituted on any nitrogen atom with 0-1 substituents selected from Ba, CO", CO and 5028, where any sulfur atom is, if necessary, mono- or dioxidized;

IN? is selected from C 4 alkyl, C 3-1 cycloalkyl, C 1 alkenyl, and C 1 alkynyl and is substituted with 0-3 substituents selected from -CM, hydroxy, halo, and C 1 alkoxy; as an alternant, B2, in the case where X is a bond, is selected from -CM, CEz, and CoE5;

BZ, B" and BZ are selected independently in each case from H, Bg, CI, E, I, -CM, C1-4 alkyl, C3-C cycloalkyl,

C 1-4 alkylthio, C 1-4 alkylsulfinyl, C 1-4 alkylsulfonyl, amino, C 1-4 alkylamino, (C 1-4 alkyl)" amino and phenyl, each phenyl being substituted with 0-3 groups selected from C- 7 alkyl, C3-C cycloalkyl, Bg, SI, E, I,

C-4 haloalkyl, nitro, C-4 alkoxy, C-4 and haloalkyl, C-4 alkylthio, C-4 alkylsulfinyl, C-4 alkylsulfonyl,

Ci-e alkylamino and (Ci-4 alkyl)»2 amino; provided that when B' is unsubstituted C1-0 alkyl, then B3 is other than substituted or unsubstituted phenyl;

B3 and B" are independently selected in each case from H, C1-4 alkyl, C3-e cycloalkyl-C1-4 alkyl and C3-c cycloalkyl;

B!Z is selected from H, C-4 alkyl, C1-4 haloalkyl, C-4 alkoxy-Ci-4 alkyl, C3-e cycloalkyl, C3-6 cycloalkyl-C.-c, alkyl, aryl, aryl (Ci- "alkyl)-heteroaryl and heteroaryl (Ci-"alkyl)-; z and D'ba are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B"" is selected from C-4 alkyl, C-4 haloalkyl, C-4 methoxy-C-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-C3- in alkyl, aryl, aryl (Ci-4 alkyl)- heteroaryl and heteroaryl (C.4 alkyl)- and benzyl, each benzyl is substituted on the aryl component 0-1 by substituents selected from C.4 alkyl, Bg, CI, P, I, C-4 haloalkyl, nitro, C1- 4-Alkoxy, C-4 HaloAlkoxy and Dimethylamino; d/z is selected from C-4 alkyl, C-4 haloalkyl, C-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl,

Alkyl and benzyl, each benzyl is substituted on the aryl component with 0-1 substituents selected from

Ci-4 alkyl, Be, Si, E, I, Ci-4 haloalkyl, nitro, Ci-4 alkoxp, Ci-4 haloalkoxy, and dimethylamino;

B19 is selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-1 cycloalkyl, and C3-1 cycloalkyl

C-C alkyl;

B" is independently selected in each case from H, C-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl and benzyl, each phenyl or benzyl being aryl substituted 0-3 groups that selected from C-4 alkyl, Bg, C1, E, I, C1-4 haloalkyl, nitro, C1-4 alkoxy C1-4 haloalkoxy, and dimethylamino;

Bza is independently selected in each case from H, C1-4 alkyl, C3-cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

B!" is selected in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C3-1 cycloalkyl-C1-1 alkyl, C1-2 alkoxy C1-2 alkyl, C1-4 haloalkyl, B'EZ(O) n-Ct-4 alkyl, and V'EVTZeM-Co.g alkyl;

BB and BZ are selected independently in each case from H, C1-e alkyl, C3-10 cycloalkyl, C3-e cycloalkyl

C1-6 alkyl, C1-3 alkoxy-C1-3 alkyl, and C1-4 haloalkyl; as an alternative. in MV!"B!? component B'Y and B? jointly form 1-pyrrolidinyl, 1-morpholipyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from B" ,

СО»2ВЯ, СО and 5028; as an alternative, in MA!" syllable B!"? and B together form 1-pyrrolidinyl, 1-morpholipyl. 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from B",

СО»2В!Я, SOV'ya and 5028!Я;

B" and B/za are independently selected in each case from H, C1-6 alkyl, C3-0 cycloalkyl, C3-6 cycloalkyl-

C-C, alkyl and C-4 haloalkyl; aryl is independently selected in each case from phenyl, naphthyl, indanyl and indenyl, each aryl being substituted with 0-5 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, methylenedioxy, C1-4 alkoxy-C1- 4 Alkoxy, -"ОВ"", Vg, SI, E, I, Si-4" haloalkyl, -SM, -MO", 5H, -5(O)0B"?, -SOV", -

СО2вВ'" -оС(О)В'В -MA Сов, -ЩСОВ7», -МАСОМА17В8я, -МА"СО2В'8, -МВ А, and -SOMVA! B" i to 1 phenyl, each phenylpiper is substituted with 0-4 substituents selected from C1-6 alkyl, C1-6 alkoxy,

Vg, ST, P, I, -SM, dimstylamino, CEz, CoEz, OSEz, 5O2Me and acetyl; and heteroarpl is independently selected in each case from pyridyl, pyrimidinyl, triazypyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxaulyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, irpazolyl, tetrazolyl, indazolyl, 2, 3-dihydrobenzofuranyl, 2,3-dihydrobeitgnliepyl, 2,3-dihydrobenzothienyl-b-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, bispoxacholin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted by 0- 4 carbon atoms with a substituent selected independently in each case from C-e alkyl, C-e cycloalkyl, Bg, C-e, E, I, C-4 haloalkyl, -CM, nitro, -OB'"", 5H, -5 (O)tV!Z, -SOV!", -СО28!", -OS(O)VYA, -MASOV', -SHSOV7", -MARSOMA' V, -

MA"CO»B!B, -MA'B, and -SOMA!"B"Z, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B", СО2в'cha, СОВa and 502812,

IBI In the second version, this invention introduces a new method of treatment of affective disorder, state)! irivoiy, headache depression, irritable bowel syndrome, post-traumatic stress disorder, supranuclear palsy, immunocompromised, Alzheimer's disease, gastrointestinal disease, anorexia nervosa or other eating disorders, alcohol or drug withdrawal syndrome, drug addiction, inflammatory disorders, cardiac -vascular or heart diseases, problems and disorders related to fertility, HIV infections (human immunodeficiency virus), hemorrhagic stress, obesity, infertility, head and spinal cord injuries, epilepsy, stroke, ulcers.

Amyotrophic sclerosis, hypoglycemia, or disorders that can be treated or alleviated by antagonizing CAE, including (but not limited to) disorders induced or maintained by CAE, in a mammal, comprising: administering to the mammal a therapeutically effective amount of a compound of formula (1): yes 3

M. A. V

: with in-x-. vna B o () or its stereoisomeric or pharmaceutically acceptable salt form, in which:

A is M or C-B7;

B is M or C-B8; provided that at least one of the groups A and B is M; p is a aryl or heteroaryl group attached through an unsaturated carbon atom;

X is selected from CH-NVU, M-VO, O, 5(O)n and connection; n equals 0, 1 or 2;

IN! is selected from C1-10 alkyl, C10-10 alkenyl, C1-10 alkynyl, C3-2 cycloalkyl, C3-e cycloalkyl-C1-6, alkyl,

Ca alkoxy-Ci-4 alkyl, -502-Ci1-10 alkyl, -502-B"", and -502-B"E;

B' is substituted with 0-1 substituents selected from -СМ, -5(О)п8и5, -СОВ'За, -СО»в1за, -МА aso, -

Mm(SOV Za)", -"MAzaSOM A zada, dao" in, "SOM zada, 1-morpholinyl, 1-piperidinyl, 1-piperazinyl, and

C3-in cycloalkyl, where 0-1 carbon atoms in Ca-in cycloalkyl are replaced by a group selected from -O-, -5(O)n-, -

МАЗа-, -МСОгВв-, -МСОВв- and -М5О2Во-, and where My in 1-piperazinyl is substituted 0-1 substituents selected from В'За, СО2В1, СОВї and 50281;

IN! is also substituted with 0-3 substituents independently selected in each case from B'!2, B'E, B/E, Civ, alkyl, Cg-C alkenyl, Cg-C alkynyl, Bg, CI, E, I , C-4 haloalkyl, -OB"Za, -MDV'Zad/"sa, and C3.in cycloalkyl, which is substituted 0-1 V? and in which 0-1 carbon atoms of Ca-in cycloalkyl are replaced by -O-; provided that B! is different from: (a) 3-cyclopropyl-3-methoxypropyl group; (B) unsubstituted - (alkoxy)methyl group; and (c) 1-hydroxyalkyl group; also provided that when B! alkyl is substituted by OH, the carbon atom adjacent to the M ring is different from

Sn";

B": is aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each B": is substituted with 0-5 substituents independently selected in each case from C1-6 alkyl, C3-C4 alkyl, B8, C1, E, I , C-4 haloalkyl, -SM, nitro, -OB'", 5Н, -Б(О)28"8, -"СОВ'", -ОС(О)В8, -MA аСОВв!", -ШСОВ7» -MA'zasOMvadyaa, -

Mmv'aSO»VvV, -Mmd'ad'za, and -somMv'tad'za:

IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolyl, isoquinolinyl, thysnyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothysnyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetracholyl, indazolyl, 2, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydroisotypyl-b5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, bemzodioxolanyl and benzodioxane, each heteroaryl is substituted by 0 -4 carbon atoms by a substituent selected independently in each case from C1-in alkyl,

C3-in cycloalkyl, Bg, SI, E, I, C-4 haloalkyl, -SM, nitro, -OB"", 5H, -5(0)tB!8, -SOV!", -OC(O)B !B8, -MA!zaSOVv/", -ЩСОВ7", -MmA'zasOoM A tad'tza, "Aza boO"vV, "MA Tadiza and -SOMVad'za, and each heteroaryl is substituted on any nitrogen atom 0 -1 substitutes selected from V!za, SO", SOV and 50289;

B!: represents a heterocyclyl and is a saturated or partially saturated heteroaryl, each heterocyclyl being a substituted 0-4 carbon atom substituent independently selected in each case from C1-e alkyl,

C3 is cycloalkyl, VI, SI, E, I, Ci4 haloalkyl, -SM, pitro, OB", 5H, -5(O)pV"y5, -SOVZa, -OS(O)B", - mA'zaSbOvViZa -М(СОвВЗа)р, -МА'засОМАЗадиба MA IzasboOvi -MATZadi ota -SOMAZadye and each heterocyclyl is substituted on any nitrogen atom by 0-1 substituents selected from В!За, СО2В/В,

Owl and 5028! | wherein any sulfur atom is optionally mono- or dioxidized;

IN? is selected from C 1 -C 3 alkyl, C 3 -C 3 cycloalkyl, C 1 -C 4 alkenyl, and C 4 -alkynyl and is substituted with 0-3 substituents selected from -CM, hydroxy, halo, and C 4 -C 4 alkoxy; alternatively, B, in the case where X is a bond, is selected from -CM, CEz, and CoEv;

BZ, B" and BZ are selected independently in each case from H, Bg, CI, E, I, -CM, C1-4 alkyl, C3-C cncloalkyl,

C1-4 alkylthio, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, amino, C1-4 alkylamino, (C1-4 alkyl)" amino and phenyl, each phenyl being substituted with 0-3 groups selected from C-4 7 alkyl, C3-C cycloalkyl, Bg, SI, E, I,

C-4 haloalkyl, nitro, C-4 alkoxp, C-4 haloalkoxy, C-4 alkylthio, C1-4 alkylsulfinyl, C-4 alkylsulfonyl,

Ci-e alkylamino and (Ci-4 alkyl)»g amino; provided that cat B' represents unsubstituted C1-10 alkyl, then BZ is different from substituted or unsubstituted phenyl;

VZ and B!? are independently selected in each case from H, C1-4 alkyl, C3-e cycloalkyl-C1-4 alkyl and C3-c cycloalkyl;

BZ is selected from H, C. alkyl, C-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-

Alkyl, aryl, aryl (C 1-4 alkyl)-heteroaryl and heteroaryl (C 1-4 alkyl) seeds; d'a and d'ba are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl ;

B"" is selected from C.sub.4 alkyl, C.sub.4 haloalkyl, C.sub.6-alkyl-C.sub.4 alkyl, C.sub.3-is cycloalkyl, C.sub.3-is cycloalkyl-

C1-6 alkyl, aryl, aryl (Ci-4 alkyl)-heteroaryl and heteroaryl (Ci-4 alkyl)- and benzyl, each benzyl is substituted on the aryl component with 0-1 substituents selected from C.4 alkyl, Vg, C, E, I, C-4 haloalkyl, nitro, C-4 alkoxy, C-4 haloalkoxy, and dimethylamino;

B/a is selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-

Alkyl and benzyl, each benzyl is substituted on the aryl component with 0-1 substituents selected from

C1-4 alkyl, Be, C1, ER, I, C1-4 haloalkyl, nitro, C1-4 alkoxy, C1-4 haloalkoxy, and dimethylamino;

Vo is selected from C 1 alkyl, C 1 haloalkyl, C 1 oxy-C 4 alkyl, C 3-6 cycloalkyl, and C 3-6 cycloalkyl-C 1-6 alkyl;

IN? independently in each case from H, C1-4 alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, phenyl and benzyl, each phenyl or benzyl being aryl-substituted 0-3 groups selected from C -4 alkyl, C1-4 alkyl, C1-4 haloalkyl, and dimethylamino;

Bza is independently selected in each case from H, C1-4 alkyl, C3-cycloalkyl, and C3-e cycloalkyl-C1-6 alkyl;

IN! is selected in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl, C1-2 alkoxy-C1-6 alkyl, C1-4 haloalkyl, B'(O)n-C1 -4 alkyl, and B'"B'ZOM-Co" 4 alkyl;

B" and B"? are chosen independently in each case from H, C1-e alkyl, C3-e cycloalkyl, C3-e cycloalkyl-

C1-6 alkyl, C1-3 alkoxy-C1-3 alkyl, and C1-4 haloalkyl; as an alternative, in MAV!" component B!" and B!? jointly form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from VU,

СО»2В!Я, SOV'ya and 5028!Я; as an alternative, at MAV!" component B!" and B" together form 1-pyrrolidinyl, 1-morpholipyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from B",

SO»VYA, SOov'ta 5028;

Ba and B/z are independently selected in each case from H, C3-is alkyl, C3-io cycloalkyl, C3-is cycloalkyl-

C1-6 alkyl and C1-4 haloalkyl; aryl is independently selected in each case from phenyl, naphthyl, indanyl and indenyl, each aryl being substituted with 0-5 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, methylenedioxy, C1-4 alkoxy-C1- 4 Alkoxy, -ОВ!", Vg, SI, E, I, Ci-4 haloalkyl, -SM, -MO", ZN, -5(O)p8!8, -SOV', -

СО28в'" -ОС(О0)818, -MASOV', -Щ(СОВ7", -MA'SOM A! Vya, -MA"ZSO»В8, -MA!VYA, and -SOMV' V" i to 1 phenyl , each phenyl substituent is substituted with 0-4 substituents selected from C1-3 alkyl, C1-3 alkoxy,

Бе, СИ, Р, И, -СМ, dimethylamino, СЕз, С2Е5, ОСЕз, 5О2Me and acetyl; and heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, triazolyl, tetrazolyl, indazolyl, 2, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-b-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted by 0 -4 carbon atoms with a substituent selected independently in each case from C-e alkyl, C-e cycloalkyl, Bg, SI, E, I, C-4 haloalkyl, -CM, nitro, -OB"", 5H, -5 (О)тВ"З, -СОВ', -СО28!", -ОС(О)В!8, -MASOV', -ЩСОВ'g -MARSOMA В, -

MA"SO»B!B, -MA'B!I, and -SOMVA' VU, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B", СО2B/!la, СОВ' Ma and 50282,

In another preferred embodiment, B' is different from cyclohexyl-(CHg),2,3,4,5,6,7,8,9 or 10 - Group.

In another preferred embodiment, B' is different from aryl-(CHg).,2,3,4,5,6,7,8, 9 or 10 - Group where the aryl group is substituted or unsubstituted.

In another preferred embodiment, B! is different from heteroaryl-(CHg). 2,3,4,5,6,7,8,9 or 10 - Groups where the heteroaryl group is substituted or unsubstituted.

In another preferred embodiment, B! is different from heterocyclyl-(CHg) 2,3,4,5,6,7,8,9 or 10 - GrUupY, where the heterocyclyl group is substituted or unsubstituted.

In another preferred embodiment, when O is imidazole or triazole, B! is different from unsubstituted C 2 3,4,5,6,7,8,9 or 10 linear or branched alkyl, or C3,4 56,7 or in cycloalkyl.

In another preferred embodiment, B!: is not a substituted OB".

Many of the compounds of this invention have one or more asymmetric centers or planes. Unless otherwise stated, the present invention includes all chiral (enantiomeric and diastereomeric) and racemic forms. A variety of geometric isomers of olefins, C-M double bonds, and the like may also be present in the compounds described herein, and all of these stable isomers are contemplated by the present invention. These compounds can be isolated in optically active or racemic forms. Methods of obtaining optically active forms are well known in the art, for example, by resolution of racemic forms or synthesis from optically active starting materials. The present invention contemplates all chiral (cyanomeric and diastereomeric) and racemic forms, and all geometric isomeric forms of the structure, except in special cases where a specific stereochemistry or isomeric form is separately indicated.

The term "alkyl" includes both branched and straight chain alkyls having a defined number of carbon atoms. "Alkenyl" includes hydrocarbon chains in straight or branched configurations and one or more unsaturated carbon-carbon bonds which may be located at any stable position along the chain, eg, ethenyl, propenyl, and the like. "Alkynyl" includes hydrocarbon chains of straight or branched configurations and one or more carbon-carbon triple bonds which may be located at any stable position along the chain, eg, ethynyl, propynyl, and the like. The term "haloalkyl" includes both branched and straight chain alkyls having a certain number of carbon atoms substituted | or a greater number of halogens; "Alkoxy" is an alkyl group with the specified number of carbon atoms attached through an oxygen bridge; the term "cycloalkyl" is intended to include saturated ring groups, including mono-, bi-, or polycyclic ring systems such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "Tallow" or "halogen" includes fluorine, chlorine, bromine and iodine.

The term "substituted" indicates that one or more hydrogens on a specified atom are replaced by an atom selected from the specified group, provided that the normal valence of the specified atom is not exceeded, and that the substitution results in the formation of a stable compound. When the substituent is a keto (ie, 0) group, then 2 hydrogen atoms are substituted on this atom.

Any combination of substituents and/or variables is permitted only if it results in the formation of stable compounds. The terms "stable compound" or "stable structure" refer to compounds that are sufficiently robust to withstand isolation with a sufficient degree of purity from the reaction mixture and formulation of an effective therapeutic product.

The term "pharmaceutically acceptable salts" includes acidic or basic salts of compounds of formulas (I) and (II). Examples of pharmaceutically acceptable salts include (but are not limited to) mineral or organic acid salts of basic residues such as amines; alkaline or organic salts of such acid residues as carboxylic acids and the like.

Pharmaceutically acceptable salts of the compounds of this invention can be obtained through the reaction of the whole acidic or basic forms of these compounds with a stoichiometric amount of the corresponding base or acid in water or in an organic solvent, or in a mixture thereof; in general, non-aqueous media such as ether, ethyl acetate, ethanol, isopropanol, or acetonitrile are preferred. A list of acceptable salts can be found in the work

Vetipdiyupya Rnagptaseciisa! Zsiepsev, 171p unit, Musk Rybiizpipd Sotrapu, Eaziyuop, RA, 1985, r. 1418, to which reference is made in this text.

The term "prodrugs" refers to any covalently bound carriers that release the active parent drug of formula (I) or (II) in response to the use of this prodrug by a mammal.

Prodrugs of compounds of formula (I) or (II) are prepared by such modification of functional groups present in these compounds that these modified groups can be cleaved into parent compounds by conventional manipulations or by injection. Prodrugs include compounds in which hydroxy, amine, or sulfohydryl groups are attached to any group in such a way that when consumed by a mammal, they are cleaved to form, respectively, free hydroxyl, amine, or sulfohydryl groups.

Examples of prodrugs include (but are not limited to) acetate, formate and benzoate derivatives of alcohol and amine functional groups in compounds of formulas (I) and (II), and the like.

The term "therapeutically effective amount" of a compound of the present invention refers to an amount that is effective to counteract an abnormal level of SVAE or to be able to treat the symptoms of affective disorder, anxiety, depression, immunological, cardiovascular or cardiac diseases and colonic hypersensitivity associated with with psychopathological disorders and stress in the patient.

Synthesis

Compounds of formula (I) can be obtained by the following synthetic routes and according to the following schemes. When a detailed description is not provided, it is assumed that those skilled in organic synthesis will readily understand what is being discussed.

The synthesis of compounds of formula (I) can be carried out according to the reaction shown in Scheme 1.

Bspeme 1 and

Wash basins in the first place in LA, what do you think about F o

The compound of formula (I) can be alkylated on the imidazole nitrogen atom using a suitable reagent. Typical conditions for carrying out this transformation include treatment of compound (II) with a base such as sodium hydride, potassium tert-butoxide, sodium hexamethyldisilazide, and the like, followed by treatment with a reagent

U-B, where y corresponds to a halide (chloride, bromide, or iodide) or pseudohalide (tosylate, mesylate, triflate, etc.), at an appropriate temperature (07C or room temperature, with heating, if necessary) in a solvent such as tetrahydrofuran, dimegylformamide or dimethylsulfoxide. Alternatively, this reaction can be carried out under Mitsunobu conditions (Miizipory, Zupipevziz 1981, pp. 1-28).

Compound (II) is treated with an alcohol compound B'OH in combination with a phosphine (triphenyl, tribuyl, etc.) and a phosphine-activating reagent such as diethyl azodicarboxplat.

Compounds of formula (II) can be prepared in the manner shown in Scheme 2.

Just in time 2

R v

In h

My AV M car with 2. vi-x-u | OM o - I dah sive I; gray Kk r (ID)

M. sl. where am I (0)

A compound of formula (II) can be attached to an aromatic compound of formula (II) with removal of elements

M-K. For compound (II), K represents a halide, a pseudohalide (such as a mesylate, tosylate, or triflate), or thiomethyl, and P represents a protecting group (if the reaction conditions allow imidazole MH to be tested; otherwise, P may be II). Acceptable P groups may include benzyl, 4-methoxybenzyl, methoxymethyl, trimethylsilylethoxymethyl, tert-butoxycarbonyl, or benzyloxycarbonyl. For the compound (IM), M represents such groups as lithium, bromomagnesium, chlorozinc, (dihydroxy)boron, (dihydroxy)boron, trialkylstanyl, and the like. The coupling reaction can be carried out in the presence of a suitable catalyst, such as tetrakisirifsnylphosphip)palladium, bistriphenylphosphine)palladium dichloride, P,3- bisidiphenylphosphino)propanenickel dichloride and the like. Two particularly useful methods include the coupling of chloroheterocycles with similarly prepared arylzinc reagents according to the Medizvpi method. (9. Oga. Spet., 1977, 42, 1821), and coupling with arylboropolyethers according to the method of 5ygiki eyi a!. (Spet.

J etseg:5, 1989, 1405). Acceptable solvents for reactions of this type are, of course, tetrahydrofuran, diethyl ether, dimethylformamide or dimethylsulfoxide. Typical temperatures range from room temperature to the boiling point of a given solvent. After coupling P, the group can be removed and compound (II) can be obtained. Conditions for removal of protecting groups are well known to those skilled in the art of organic synthesis, for example, hydrogenation to remove benzyl or benzyloxycarbyl, use of a fluoride (such as tetrabutylammonium fluoride) to remove enlyletoxmethyl, use of an acid (such as trifluoroacetic acid) to remove tert-butoxycarbonyl or 4- methoxybenzyl, etc. Compounds of formula (II) can be prepared according to

Scheme 3.

Zepele 3 '

And with and with

NM pe A, "A -8 - | -IN

To us

Kk Kk ap)

AND; K z

M. Yes

Kk

SI)

The diamine compound of the formula (M) (in this case, P represents a group such as benzyl, which can be introduced already attached to the nitrogen atom; otherwise, P can first correspond to H, and at a later stage another protector is introduced) is used in a cyclocondensation reaction for creation of an imidazole ring. The conditions used depend, of course, on the choice of the X group and may include an intermediate (MI).

An overview of the reactions on the formed) imidachols can be found in the work of Sotrgepepsime Neiegosussis Spetizig (Regdatop Rgezv, 1984), vol!.5, pp. 457-498.

Preparation of compounds of formula (M), where A and B are nitrogen atoms, can be carried out according to Scheme 4.

Ripe 4

And not dz NM. M. I

I am M

O.M nem -4 - K Kk (M) (M, A and B as M) visible t

M

To us

Kk

SU)

The compound of formula (MI) can be obtained from commercial sources, especially for K - chloride). Compounds containing pseudohalide K groups can be prepared from the corresponding dihydrox compounds by treatment with a suitable activating reagent, such as organosulfospic anhydride or sulfonyl chloride. The compound (MII) can be converted into (M) by (i) monoalkylation with the compound P-MH" followed by the reduction of the nitro group; (i) reduction of the pyro group with the formation of an amine compound of the formula (MI) followed by monoalkylation with the compound P-MH"; or (iii) by using an ammonium source (ammonia, ammonium hydroxide, etc.) according to any scheme followed by protection of the amino group with a protector R. The chemistry of pyrimidines of this type is well presented in the literature, and a corresponding review can be found in Sotrgepepvime Neiegosusiis Spetivig, mo. !.6.

Alkylation of chloropyrmidines by amoebic compounds can be carried out both under acidic (for example, HCl or acetic acid) and under basic (trialkylamines, potassium tert-butoxide, etc.) conditions. The petro groups in compounds of this type can be reduced to amino groups using one of many conditions, including catalytic hydrogenation, stannous chloride, sodium dithionite, zinc metal, iron powder, and the like.

The preparation of compounds of formula (U), where A or B are nitrogen atoms, is presented in Scheme 5.

Bbspete 5 d' 7 7 R iii h

BUT. schi In NO. my VZ we in.

Som ohM om 9) o o o (o Fu v? 0" (kp)

Kyaz I

M is 7

He is not in ho Kk | She, . oh

R z y Kk

Shk in She p ia ach zh «tyti zh nn. i om R (in 8)

Kk Kk

R 7

SU, A m M) (KHM, ni vo

M on

Kk and (u.e)

A hydroxypyridone compound of formula (IX) can be subjected to nitration to give compound (X) using conditions such as concentrated or fuming nitric acid, if necessary, in the presence of concentrated sulfuric or acetic acid. Hydroxypyridone can be selectively monoactivated by the K group to form a compound of formula (Xi); one method of achieving this involves treating the dicyclohexylamine salt of compound (X) with phosphorus oxychloride to form (XI), where K-SI. Alternatively, both hydroxy and pyridone groups in compound (X) can be activated simultaneously, using harsher conditions such as phosphorus oxychloride and heating, to form compound (XII). Compound (XI) can be converted to the amino-protected compound (XII) using the same general route as discussed above for pyrimidines. Mooalkylation using compound (XIII) is also possible, but this may result in the formation of mixtures of regioisomeric products (XIM) and (XM). The nitro groups in these compounds can then be reduced as discussed above to form compounds of formula (M) where A or B corresponds to nitrogen.

An alternative approach to the method involving the introduction of B! groups at the primary stage, presented in Scheme 6. immediately 6 in B"

AND.

Kk ory nm ay M actions

In -- | In ve-kh- I In "her and "y bom OoM m

Kk Kk (about (ХУ (ХМ) and | in!

Z M Z i n: Shk

Kk lion N ley M lov fo- | and O- dI-- x- | Ts - i -- nom nom M 2 2

Kk Kk 4 (XM) (XX) Oh)

It is especially useful in cases where B' is such a group that alkylation of compound (II) is impractical (for example, a very large B' group), but it can be used in general.

In this method, compounds of the formula (HMI) or (HMI) (amino- or pyropyridines or pyrimidines) are alkylated with the amine reagent Ni-MNo under acidic or basic conditions as shown above. A nitro compound (XM) can be converted into an amine compound (XIX) through the nitro reduction reactions described above. Compound (XIX) can be cyclized into imidazole compound (XX). As above, the specified reaction will depend on the choice of the X group.

For example, for X-START:? an orthoester reagent such as В-CH(ВУС(ОВ)z) can be used when heated in pure solution or high-boiling solvents and in the presence, if necessary, of an acid catalyst (such as hydrochloric or sulfuric acid) (see Mopidotegu apa Tetrier, U. Ogd/ Spet., 1960. 25, 395). For X-MV!O, cyclization is carried out using such reagents as the guanidine reagent of the formula

В2В'ОМ-С(-МН)МН" or a urea derivative with the structure В2В'ОМ-С(-МНИЮ, where O corresponds to a group similar to

Osn", 5СН3 or 502СН".

For XO, the ring is formed using a reagent with the structure (B2O0)4C (in acetic acid catalysis), provided it is possible to use such a reagent with the appropriate B: group (see Vgomp apa GG Uuppa, ..

Spent boss. Reykip Tgapv. And 1974, 349). Alternatively, the diamine (XIX) is treated with phosgene followed by O-alkylation to introduce the LC: group (using a reagent such as B-I or B2-Bi). A similar path can be used for X-5 using thiophosgene or a similar reagent followed by 5-alkylation of B? group The sulfur atom in this compound (and, in general, the sulfide groups in a given molecule) can be oxidized to a sulfoxide or sulfone if desired by treatment with a suitable oxidizing agent, such as potassium permanganate, potassium peroxomoposulfate, or t-chloroperbenzoic acid. | finally, compound (XX) can be used in an aryl coupling reaction as shown above to replace the K group with the desired aryl group in compound (1).

The methods of synthesizing the compounds VI-OH, Vi-Uu and B'-MH2 are connected in that this alcohol can be used in the synthesis of the other two compounds, as shown in Scheme 7. , Ka i vl i zh i I. (bsebete 1; (bepate b)

For example, the hydroxy group can be converted into the following B groups using the specified reagents (this way is not limited to the specified 9 groups): methanesulfonate, using methanesulfonyl chloride or anhydride and the appropriate base; toluenesulfonate, using toluenesulfonyl chloride or anhydride and the appropriate base; iodide, using iodine/triphenylphosphine; bromide, using phosphorus tribromide or carbon tetrabromide/triphenylphosphine; or trifluoromethanesulfonate, using trifluoromethanesulfonic anhydride and a suitable base.

Both B!-OH and B!-) are used in the methods shown in Scheme I. Conversion of B) to B'-MZ requires the use of an azide source such as sodium azide and a solvent such as dimethylsulfoxide or dimethylformamide or water , and an interphase catalyst (such as acidic tetrabutylammonium sulfate).

Reduction of the azide compound H/!-Mz to B'-MH" can be carried out using reagents such as sodium borohydride or triphenylphosphine, or hydrogen gas and a catalyst (such as palladium on carbon). Amine

В!-МН" can then be used in the methods presented in Scheme 6.

In cases where the B'-OH compound can be represented by the structure of the formula (XXI) (Scheme 8), where B"g and B"E are substructures which, together with the carbinolmethine group, correspond to the group B", it can be obtained by attachment to a carbonyl compound.

Bsleshte 5 di» tsa dya works all shk KI yah om-ya” o on o shho sha o oho)

This way is especially useful in the case when V'g or V! corresponds to a cycloalkyl group, for example, cyclopropyl. To obtain an alcohol compound of the formula (XXI), the reaction of an organometallic reagent (where M' corresponds to a metal group, such as Her, SiSM. Si, MOSI, MoVg, MOI, ps, StCI, etc.) with aldehyde can be used. Alternatively, the ketone of formula (XXIII) can be treated with a reducing agent such as sodium borohydride, lithium aluminum hydride, and the like, which will also result in the formation of an alcohol of formula (XXII).

For the preparation of compounds of the formula (XXII), standard methods of synthesis of ketones, which are known to specialists in the field of organic synthesis, can be used.

For the synthesis of B'-OH alcohols, a homologous approach can also be used, which includes the ring-opening reaction of a cyclic ether with the help of organometallic reagents (Scheme 9).

Vsrete From virgins ate from where you are

СХ сн дю"M" gu ok) oo vit oh) on (ХУ)

In this case, the organometallic reagent B'z-M" was used, where M" corresponds to such metals as Ma, 7p or Cy. Especially useful is the method described in Nyupnei a)!., Tehigapedgop I etsegv, 1979, (17), pp. 1503-1506, which uses the reaction of organomagnesium reagents with cyclic ethers under catalytic conditions provided by copper (I) iodide. of the epoxy compound of the formula (XXI) In this method will give the alcohol compound of the formula (XXIM), and the use of the oxetane compound of the formula (XXU) will lead to the formation of the alcohol of the formula (XXMI). Both compounds (XXUM) and (XXMI) are varieties of B'-OH.

The synthesis of compound B'-MHg of the formula (XXII) is presented in Scheme 10.

Zepete 10 v! in!" IN! в'в дя дии о Мн, МН (ХХ) (ХХ) d'z vyi She tu , Y nya me-d'i: . nn. - a a (XXIX) СХ,

A simple reductive amination of the ketone (XXII) will lead to the formation of the amine (XXII). This reaction can be carried out using anhydrous ammonia in the presence of hydrogen and a catalyst. Alternatively, addition of an organometallic reagent to a nitrile compound gives an imine, which can be treated with a reducing agent (such as sodium cyanoborohydride) to form the amine (XXII). Finally, the compound of the formula (XXMII), where OO is optionally substituted by an oxygen atom (i.e., an oxime) or a nitrogen atom (i.e., a hydrazone), can be reacted with the organometallic reagent B'Z-M." In this case, the following metal groups M" were used like MoVg, SysSi or Sesi". Addition intermediates of formula (XXIX) can be subjected to reductive cleavage (using sodium/liquid ammonia or catalytic hydrogenation) to form amines (XXIII).

Amino acids, both natural and synthetic, are a potential source of useful starting material for the synthesis of the compounds of this invention. Scheme 11 depicts some possible applications of this approach.

Zepete 11 ' '

Fuck them! era internship V zuton oyu OO) skh) ' 1 1 chn, NAR MN-Rg (ХХКУ) ХУ) Х)

Protected amino acids of the formula (XXXI) are obtained from the starting compounds of the formula (XXX); protecting groups ("Po") include tert-butoxycarbonyl, benzyloxycarbonyl, and triphenylmethyl. Methods of such protection are described in the well-known literature on peptide chemistry. The carboxylic acid group can be reduced using reagents such as lithium borohydride to give the alcohol (XXXI). The hydroxy group can be converted to a leaving "B" group as described above. The compound of the formula (XXXI) can be treated with appropriate reagents to form a variety of functional groups included in the scope of this invention (compound (XXXIM)); substitution of U with cyanide ("in this case, sodium cyanide in heated dimethylformamide can be used) gives a nitrile, substitution of .) with mercaptan (in the presence of a base such as potassium carbonate) gives a disulfide, substitution of . with a secondary amine gives a tertiary amine, etc.

Compounds of formula (I) with unsaturated B! groups can serve as an additional source of compounds covered by the present invention. Unsaturated (double and triple) bonds can participate in cycloaddition chemistry with appropriate reagents (Scheme 12). Cycloaddition of an alkyne compound of the formula XXXMI to 1,3-dienes with the formation of 6-membered ring compounds similar to compounds of the formula XXXMI! (known as reaction

Diels-Alder), and the cycloaddition reaction with 3-atom dipolar reagents with the formation of heterocyclic compounds of the formula XXXMIII are known to specialists in the field of organic synthesis. A specific example of this approach is the synthesis of isoxazoline compounds of the formula XXXIX from alkyne XXXMI and a pythryl oxide reagent.

bspesche 12 ave. di» : ve / y In mV - shk vu

M s, » y 7» ХХХУ1ІІ

And - and m. viv ve y

M - tat M M rosu s chE vi-x-U || Ky vi-kh-K. zr - x

M M M

1" r r V

ХХХХХХ (КМ у и " а о

M-o- M.,B3 v-ya M-0 M g shsh-k-k z ' o

XXXIX

The synthesis procedure shown in Scheme 13 can be used to prepare 4,5-s imidazopyridines.

bspesche 13 si sv y . ko 1. sNergeui MO; 1 amoeba

She; BUT She and: in | | 2. ROSIz sa n7oto o

M on H 715 n

ХХХХХХХХХХХХХ 11

KN "what

EM, | ZD 2 ROSI1z -- 1 - Tea SINGULARS, English. nni iini, iklo eyes J

SNISM, iRgO MNE | nt and about Me

ХХХХІІІІХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХХЮХХХХХХХХХХХХХХХХХХХХХХХЮЮХХХХХХХХХа had

Hey! chh

AIV(ON), | 1. Smear, ---- A A 6 Mom tt y yuyu Rv

Ra ge; si. 2 2. SznesOn vani... PME/NO 2 Ag Ah хХХХХ ххкл

Nitration of 2,4-dihydroxypyridine (XXXX) by NMOz as previously described (Koaodeyi ei ai!., Veei. Tam. Spit. RNuvz-

Vav., 29, 38, 67 1948) led to the formation of the corresponding 3-nitropyridone (XXXXI), which was treated with an organic amine base such as cycloheptylamipi, which led to the selective formation of the corresponding 4-chloropyridone (XXXXIII). The latter, in turn, was reacted with the primary amine АМН», where A is the group described earlier, in an aprotic or protic solvent such as CH3СМ, ХОМ5О, ОМЕ, or an alkyl alcohol in the presence of an organic or inorganic base such as and rialkilamip, CaCO3, Ma2SoO3, and so on, and in the temperature range of 20-200"C with the formation of the 4-amine adduct (XXXXII). Pyridone (XXXIII) was converted into 2-chloropyrpidine (XXXXIM) by treatment with ROCIz, and (XXXXIM) was combined with arplboronic acid AgHV(OH)" under the conditions of palladium catalysis with the formation of compound (XXXXXM). Nitropyridine (XXXXXM) was reduced to the corresponding aminopyridine with the help of Mag25b2O4 or Re, Zp or Zpbig and transformed into imidazo(|4,5-s| pyridine by refluxing in propionic acid.

The same transformation can be carried out using a nitrile, imidate, thioimidate or trialkyl orthopropionate.

The synthetic procedure shown in Scheme 14 can be used to prepare 4,5-5 imidazopyridipes.

zslete 14 si 1 ks2 mo; v21Vvg, AoMOz AEV(ONI; I nya plyny Dryn Y, anna nyny

СНе РЯЗ(РРИИз)с1;

Co. MO o821 Vv(on);, OMELYO

Ah where - WHERE

Mo; but re

SR»SO; In tk ROS; from 2. VKN, k

M ov:x1 y o n Gai

Kk

XXIX 1, and II

IY

K, n 1. Ma»;55O, p VT 2. soup GU

Ag

BELLOWS

Reaction of 4-chloropyridone (XXXIII) with an aryl halide such as benzyl bromide in benzene and in the presence

AdgSO", as shown in Scheme 13 (Ztiy A. M. eiaii.,. Med. Spet., 36, 8, 1993), in the temperature range of 30-80"C will lead to the formation of the corresponding 2-benzyloxypyridine) (XXXXXMII). The latter was combined with arylboronic acid AgB(OH)" under the conditions of palladium catalysis with the formation of compound (XXXXX).

The benzyloxy group can be removed by treatment with a strong acid, such as trifluoroacetic, triflatic, sulfuric, hydrochloric, etc., with the formation of pyridone (I). The latter was converted to 2-halopyridine using

РОХ», РХ5 or the corresponding triflate, tosylate or mesylate, which was replaced by the primary amine АМНг with the formation of compound (II). The nitro group was reduced under the conditions shown in Scheme 13, and the aminopyridine was cyclized to imidazolo(4,5-b|pyridine) (GII) under the conditions shown in Scheme 13.

The following examples are given to further detail the invention. These examples, which show the best way to implement the present invention, are for illustration purposes only and are not limiting of the present invention.

Methods of obtaining 8-ethyl-9-(1-ethylpentyl)-6-(2,4,6-trimethylphenyl)purine (Table 1, Example 2, Strei ura A) and 9-butyl-8-ethyl-6-(2 ,4,6-trimethylphenyl)purine (Table 1, Example 27, Structure A) discussed below can be used to prepare all of the examples of Structure A in Table 1, Table 1A and

Tables 18 With minor procedural modifications where necessary and using reagents of acceptable structure.

Preparation methods of 3-(1-cyclopropylpropyl)-7-(2,4-dichlorophenyl)-2-ethyl-ZH-imidazo(|4,5-b|pyridine (Table 1, Example 38, Structure B) and 1-( 1-Cyclopropylpropyl)-4-(2,4-dichlorophsenyl)-2-syl-1H-imidazoi|4,5-c|Ipyridine (Table 1, Example 38, Structure C) can be used to obtain many compounds of example Structures B and C in Table 1, Table 1A, Table IV and Table 1C with minor procedural modifications where necessary and using reagents of acceptable structure.

Example 2

Preparation of 8-ethnyl-9-(1-ethylpentyl)-6-(2,4,6-trimethylphenyl)purine

Part A. A solution of 5-amino-4,6-dichloropyrimidine (10.0 g, 61.0 mmol) and triethylamine (12.8 mL, 91.5 mmol) in ethanol (100 mL) was treated with benzylamine (7.30 mL, 67 .1 mmol) and heated at 502C overnight. The resulting mixture was cooled and the crystalline solid was collected by filtration.

The solid was triturated with hexane, filtered and dried under vacuum. For the second time, the crystalline mass was collected from the mother liquor and purified as in the first case, and as a result, a total of 12.67 g (48.8 mmol, 8095) of 5-amino-6-benzylamino-4-chloropyrimidine was obtained. TI C (thin-layer chromatography) AN 0.10 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): a 7.62 (1H, 5), 7.13-6.97 (511, t), 6.61 (1H, Bgi, 9u25 Gu), 4.43 (2H . .

Part B. A solution of the diamine from Part A (10.45g, 44.5mmol) and three drops of concentrated hydrochloric acid in grpetyloriopropionate (7/Oml) was heated to 1007C for 1 hour, then cooled, poured into water (200ml) and extracted ethyl acetate (2 x 200 ml). The extracts were washed successively with brine (100 ml), then combined, dried over anhydrous sodium sulfate, filtered and evaporated. The residue was separated by column chromatography (silica gel, 20:80 ethyl acetate-hexane) to give the product, M-(6-benzylamipo-4-chloropyrpmidin-5-yl)-O-ethyl-propionimidate (12.82 g, 40.2 mmol , 9095), in the form of a crystalline solid. Tpl--85-862S. TI S VE 0.25 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): a 8.19 (Ш, 8), 7.35-7.29 (BN, t), 5.21 (IN, p 9-5 Hz), 4.70 ( 2H, a, 92-5.9 Hz), 4.29 (211, ri), 2.15 (2H, Bga, 9-7.3 Gu), 1.35 (ZN, 9-7.0 Hz) , 1.06 ZN, i, 9–7.3 Hz).

Part C. A solution of the imidate compound obtained in Part B (10.66 g, 33.4 mmol) and p-toluenesulfonic acid monohydrate (100 mg) in diphenyl ether (1 mL) was heated to 170°C for 2 hours.

The resulting mixture was cooled and poured into 5 mL of water. Then ecchiragukalm with ethyl acetate (2x50ml), and the extracts were washed successively with brine (50ml). combined, dried over anhydrous sodium sulfate, filtered and evaporated. The residual material was separated by column chromatography (silica gel, hexane to extract the diphenyl ether, then 30:70 ethyl acetate-hexane) to give the product, 9-bsipple-b-chloro-8-ethylpurine, as an oil (8.16g, 29.9 mmol, 8995). TI S A 0.20 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): a 8.72 (1H, 5), 7.37-7.29 (ZH, t), 7.19-7.14 (2H, t), 5.46 ( 2H, 5), 2.89 (2H, a, 9-7.7 Hu), 1.38 (ZH, i, 9-7.7 Hz). Mass spectroscopy (MNzg-SI): t/e 276 (6), 275 (36), 274 (20), 273 (100).

Part 0. A solution of zinc chloride (5.32 g, 39.1 mmol) in anhydrous, freshly distilled tetrahydrofuran and (Homl) was treated at room temperature with a solution of mesitylmagnesium bromide (39.1 ml, 1.0 M, 39.1 mmol) in diethyl ether. After 45 minutes, in a separate beaker, a solution of bis(triphenylphosphine)-palladium dichloride (0.92 g, 1.3 mmol) in tetrahydrofuran (10 mL) was treated with a solution of diisobutylaluminum hydride (2.b mL, 1.0 M, 2.6 mmol) in hexane. This mixture was stirred for 15 minutes, then treated drop by drop with a solution of mesitylzinc chloride using a cannula. Then, using a syringe, a solution of the chloropurine compound in 17 Oml of tetrahydrofuran was added, and the specified mixture was stirred for 12 hours at room temperature. it was poured into water (150O0ml) and acidified by adding 1M aqueous hydrochloric acid dropwise until this mixture became homogeneous. Extraction was then carried out with ethyl acetate (2 x 150 ml), and the extracts were successively washed with saturated brine solution (100 ml), combined, dried over anhydrous sodium sulfate, filtered and evaporated. The residue was separated by column chromatography (silica gel, 30:70 ethyl acetate-hexane) to give the product, 9-benzyl-8-ethyl-6-(2,4,6-trimethylphenyl)purine, (6.68 g, 18.7 mmol, 7295). as a white waxy solid. Tpl--121-12276. "H NMR (300 MHz, SOS"): a 9.00 (1H, 5), 7.38-7.31 (ZH, t), 7.23-7.21 (2H , t), 6.96 (2H, 5), 5.50 (2H, 5), 2.84 (211, a, 9U-7.6 Hz), 2.33 (311, c), 2.06 (6H . .

Part E. A solution of the powdery compound from Part O (5.33 g, 14.95 mmol) in trifluoroacetic acid (320 mL) was divided into four Parr beakers, and each portion was treated with 0.8 g of 2095 palladium hydroxide on carbon.

The contents of each beaker were hydrogenated (50 psi) in a vibrator for 18 hours. The beakers were flushed with nitrogen, and the solutions were combined, filtered through celite, and evaporated. The residual material was separated by column chromatography (silica gel, 50:50 ethyl acetate-hexane) to give the product, 8-ethyl-6-(2,4,6-trimethylphenyl)purine (3.75 g, 14.1 mmol, 9495), in in the form of a white crystalline substance. Tpl-:-215- 21726. TI C Vk 0.17 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): a 12.35 (1H, Big 5), 9.03 (1H, 5), 6.96 (2H, 5), 3.05 (2H, a, 9-7 .7 Gu), 2.32 (ZN, 5), 2.05 (BN, 5), 1.50 (ZN, I, 9-7.7 Hz). Mass spectroscopy (MHz-SI): t/e 269 (2), 268 (19), 267 (100).

Part R. A solution of the purine compound from Part E (200 mg, 0.75 mmol), 3-heptanol (0.13 mL, 0.90 mmol), and triphenylphosphine (0.24 g, 0.90 mmol) in freshly distilled tetrahydrofuran ( 5 ml) was cooled to 0 C and treated dropwise with diethyl azodicarboxylate (0.14 ml, 0.90 mmol) using a syringe. This mixture was stirred for 12 hours, then evaporated. The residual material was separated by column chromatography (silica gel, 15:85 ethyl acetate-hexane) to give the title compound as a white solid (0.152g, 0.42 mmol, 5695). Tpl»99-10020. TI S A; 0.17 (10:90 ethyl acetate-hexane). "H NMR (300 MHz,

SOSIz):a 8.91 (1H, 5), 6.95 (2H, 5), 4.22 (1H, Bi), 2.92 (211. a, 9-7.7 Hz), 2.41 (2H, BI), 2.32 (ZN, 5), 2.10-1.98 (2H, t), 2.05 (ZN, 5), 2.04 (ZN. 5). 1.37 (311.1, 97.5 Hz), 1.34-1.23 (AN, t), 0.84 (ZN, i, 9-7.1 Hz), 0.81 (ZN, i, 9 -7.5 Hz).

Mass spectroscopy (MS-SI): t/e 367 (3), 366 (27), 365 (100).

Example 27

Preparation of 9-butyl-8-ethyl-6-(2,4,6-trimethylphenyl)purine

A solution of 8-ethyl-6-(2,4,6-trimethylphenyl)purine (200 mg, 0.75 mmol) in anhydrous dimethylformamide (5 ml) was cooled to 0"C and treated with a dispersion of sodium hydride in mineral oil (72 mg 5Ovag.95, 1.50 mmol).After 1 hour, bromobutane (0.10 mL, 0.90 mmol) was added via syringe, and the mixture was stirred for 12 hours. The mixture was poured into ethyl acetate (120 mL) and washed with water (3 x 120 mL) and brine (100 mL) The aqueous layers were successively back-extracted with ethyl acetate (120 mL), and the extracts were combined, dried over anhydrous sodium sulfate, filtered, and evaporated.The residue was separated by column chromatography (silica gel, 20:80 ethyl acetate-hexane) to give the title product as "viscous oil (64.2 mg, 0.20 mmol, 27965). TI C B; 0.20 (30:70 ethyl acetate-hexane). "H NMR (300 MHz,

SOSIzv): a 8.96 (11 th. 5), 6.95 (211, c), 4.25 (2H, her, 9-7.5 Hz), 2.93 (2H, a, 9-7 .7 Gu), 2.32 (ZN, 5), 2.04 (611, c), 1.91-1.46 (211, t), 1.50-1.38 (2H, t), 1 .39 (ZN, Her, 9-7.7 Hz), 1.01 (ZN, i, 9-7.5 Hz). Mass spectroscopy (MS-SI): mp 325 (3), 324 (23), 323 (100).

Example 35

Derivative of 6-(2,4-dichlorophenyl)-8-ethyl-9-(1-ethylpentyl)purine

A solution of 2,4-dihydrobenzeneboronic acid (572 mg, 3.00 mmol) and ethylene glycol (205 mg, 3.30 mmol) in benzene (20 mL) was heated in a reflux condenser with azeotropic extraction for about 8 h.

The resulting solution was cooled and treated with b-chloro-8-ethyl-9-(1-ethylpentyl)purine (see

Example 2, Part C, above; 562 mg, 2.00 mmol), thallium carbonate (1.03 g, 2.20 mmol) and tetrakis(triphenylphosphine)palladium (116 mg, 0.10 mmol). The resulting mixture was heated with an inverted refrigerator under a change of lime for 12 hours, then cooled, filtered through celite and evaporated. The resulting residue was separated by column chromatography (silica gel, 10:90 ethyl acetate-hexane) to give the title compound as a viscous oil (530 mg, 1.35 mmol, 68905). 90). TS A: 0.31 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): a 8.94 (1H, 5), 7.71 (1H, a, 9-8.4 Hz), 7.58 (1H, a, 9-1.8 Hz ), 7.41 (1H, aa. at -8.4, 1.8 Hz), 4.27 (1H, ro), 2.95 (2H, a, 9-7, Hz), 2.41 (2H, Bi), 2.11-1.98 (2H,pI), 1.42(311. 1.9) 27.3 Hz). 1.37-1.20 (ZH, t), 1.09-0.99 (1Н, т), 0.84 (ЗН, и, 9У-7.7 Hz), 0.82 (ЗН/ .9-7.7 Hz) Mass spectroscopy (MNz-SI): t/e, calc. . for SgoNg5IMaSi2: 391.1456, found 391.1455: 395 (11), 394 (14), 393 (71), 392 (29), 391 (100).

Example 38

Preparation of 3-(1-cyclopropylpropyl)-7-(2,4-dichlorophenyl)-2-ethyl-ZH-imidazo(4,5-b|pyridine

Part A. 2,4-dihydroxypyridine (15.0 g, 135 mmol) was heated in NMO3 (85 mL) at 80"C for 15-20 minutes until it went into solution. The specified temperature was maintained for 5 minutes, and after cooling, it was poured into ice/water ("7200 ml). The precipitated solid was filtered and dried (19.0 g, 9095 yield). "H NMR (300 MHz, atvo ab): 12.3-12.5 (1H, Bg5). And 1.75-11.95 (1H, Bi), 7.41 (1H, a 0-73 Hz), 5 .99 (1H, and 20--7.3 Hz).

Part B. 4-Hydroxy-3-nitropyridone (8.0 g, 51.25 mmol) and cycloheptylamine (6b.8 mL, 53.4 mmol) were refluxed in methanol (100 mL) for 15 min. The solvent was evaporated and the residual solid was washed with 1:11 EtOAc/hexanes and dried under vacuum. The cycloheptylamine salt was stirred in ROSIiz (bOml) for 40 hours, it was exposed to ice/water ("6b00ml). The precipitated product was collected and dried under vacuum (7.0 g, yield 7895). "H NMR (300 MHz, atvo ab): 12.8-13.05 (1H, biv), 7.73 (1p, ayu9-7.0 Hz), 6.50 (1H, 4-70 Hu).

Part C. 4-chloro-3-nitro-pyridone (0.5 g, 2.86 mmol), AdgSO3 (0.83 g, 3 mmol) and benzyl bromide (C), 30 ml,

with mmol) was mixed in anhydrous benzene (20 mL) at 60°C for 5 hours. The reaction mixture was filtered and evaporated in vacuo. The residue was subjected to silica gel chromatography (1095 EAs/hexanes as eluent) to give the product (0.6 and 79905 ). "IN NMR (300 MHz, SOS"): 8.15 (1H, and 94.0 Hz), 7.30-7.42 (B5H, t), 7.04 (1H, and 44.0 Hz ), 5.50 (2H, 5).

Part 0. 2-benzyloxy-4-chloro-3-nitropyridine (0.5 g, 1.9 mmol), 2,4-dichlorophenylboronic acid (0.363 g, 1.9 mmol), Ra(PPz)2O5" (76 mg, . This mixture was distributed between

EODAc (100ml) and water (30ml), and EUAc was washed with water, brine, dried and evaporated under vacuum.

The residue was chromatographed on silica gel (1095 EtOAc/hexanes as eluent) to give the product (37mg yield

Bho9rv). "H NMR (300 MHz, SOSI»z): 8.31 (1H, y, 9-5.1 Hz), 7.51 (1H, y, uU-2.2 1 c), 7.30-7 .43 (6H, t), 7.20 (1H, and 3-8.0

Hz), 6.91 (1H, ash-5, I Hz), 5.56 (2, 5).

Part of BE. 2-Benzenoxy-4-(2,4-dichlorophenyl)-3-nitropyridip (1.65 g, 4.39 mmol) was stirred in

SEzZSO»H (Bml) at 25"C for 4 hours. SEZSO2H was evaporated in vacuo, and the residue was filtered for 2090

EtOAc/hexanes and used in the next reaction. "H NMR (300 MHz, SOSIv). 7.62 (1 H, a 9d-27.0 Hz), 7.53 pn, ashu-2g2 Gu), 7.34 1Hn, aaz-1.0.22 Hod ), 7.22 in, a.1-8.1 Po, 6.33(1 N, ash-7.o Hz).

Part of RE. 4-(2,4-dichlorophenyl)-3-nitropyridone (4.39 mmol) was heated with an inverted refrigerator)

ROSIz, (5 ml) for 5 hours. After cooling, it was poured into ice/water (-bOml) and extracted with EtOAc (2x100O0ml). EtOAc was washed with saturated NaHCO 3 , brine, dried and evaporated in vacuo.

It was used in the next reaction without further purification. "H NMR (300 MHz, SOSIv): 8.60 (1Na 325.2 Hz), 7.54 (1H, a, yuth22 Hz), 7.36 (1H, aa 0-81, 2.2 GHz), 7.20 1H, ashu-vy Gu).

Part of school 2-chloro-4-(2,4-dichlorophenyl)-3-nitropyridine (0.5 g, 1.65 mmol), 1-cyclopropylpropylamine hydrochloride (461 mg, 3.4 mmol) and diisopropyl ethylamine (1.2 bml, 0.72 mmol) were heated with an inverted refrigerator in CH3SM (10 ml) for 64 hours. The mixture was partitioned between EtOAc (70 mL) and water (40 mL).

The aqueous layer was extracted with EtOAc (500 mL) and the combined EtOAc extracts were washed with brine, dried and evaporated in vacuo. The residue was chromatographed on silica gel (1095 EAs/hexanes as eluent) to give the product (310 mg, yield 5195). "H NMR (300 MHz, SOSIv): 8.29 (1H, a 0-47 Hz), 7.76 (1H, Bha .1-8.0

Hz), 7.46 (1H, ashue2g, 2 Hz), 7.32 (1H, aa 0-8.5, 2.2 Hz), 7.15 (1H, a 9-85 Gu), 3.72 -3.85 (IN, t), 1.70-1.80 (2Н, t), 0.90-1.08 (4Н, t), 0.30-0.66 (4Н, t).

Part H. 2-(1-cyclopropyl)propylamino-4-(2,4-dichlorophenyl)-3-nitropyridine (310 mg, 0.5 mmol) was dissolved in dioxane (3 mL), and water (3 mL) containing concentrated MNAOH (0.3 ml), followed by the addition of Mag52O4 (1.1 g, 6.86 mmol). The reaction mixture was stirred at 25°C for 4 hours and extracted with EtOAc (100 mL). EtOAc was stirred with brine, dried and evaporated in vacuo. The residue was chromatographed on silica gel (2595 EtOAc/hexane and -195 concentrated MNAOH as eluent) to give the product ( 15Omg, output 5195). "H NMR (300 MHz, SOSIv): 7.73 (1H, and y-25.5 Hz), 7.53 (1H. and 3-16 Hu), 7.35 (1H, aa 0-8, 1.8 Hz), 7.24 (1H, and w-8.I Hz), 6.35 (1H, and 9-5.5 Hz), 4.3 (11-I, Bg5 ), 3.5 (1H, biv), 3.42-3.55 (1H, t), 3.04 (2H, Brgv), 1.70-1.81 (2H, t), 0.88- 1.08 (4H, t), 0.3-0.6 (4H, t).

Part 1. 3-Amino-2-(1-cyclopropyl)propylamino-4-(2,4-dichlorophenyl)-pyridine (140mg, 0.42mmol) was refluxed in propionic acid (5Xml) for 23 hours. Then this mixture was diluted with water (50 ml), neutralized with solid Mansoz and alkalized with 5095 Mahon. Then it was extracted

KODAcs (80ml) and EOAcs were dried and evaporated in vacuo. The residue was chromatographed on silica gel (1095 and 2095 EoOAc/hexanes as eluent) to give the product, which was crystallized from hexanes (7mg, yield 4590).

Tpl-118-11926. "H NMR (300 MHz, SOSIz): 8.91 (1H, and 04.7 Hz), 7.62 (1H, and 2-72 Hu), 7.55 1H, ashSh-18 Hu), 7.37 (IN, aa shu-?2, 1.8 Hz), 7.23 (IN, a y-sh4.7 Gu), 3.50-3.70 (1H, biv), 2.87-2.96 (2H, a), 2.36-2.56 (1H, t), 2.18-2.35 (IN, t), 1.90-2.05 (1H, t), 1.38 (ЗН , 0), 0.86 (311, U, 0.75-0.84 (1H, t), 0.40-0.54 (1H, t), 0.15-0.25 (1H, t) .

Example of ZVA

Preparation of 1-(1-cyclopropylpropyl)-4-(2,4-dichlorophenyl)-2-ethyl-1H-imidazo(|4,5-c|pyridine

Part A. A mixture of 4-chloro-3-pyrro-2-pyridone (2.0 g, 11.4 mmol), 1-cyclopropylpropylamine hydrochloride (1.5 g, 11.4 mmol), and N,M-diisopropylethylamine (4.8 mL, 27.4 mmol) in SNZSM (50 ml) was stirred at 2570 for 16 hours and with an inverted refrigerator for 4 hours. After cooling, it was evaporated in vacuo and the residue was partitioned between EOAc (100 mL) and water (50 mL). The insoluble substance was removed, washed with water and EOAc, and dried under vacuum (1.51 g). The filtrate layers were separated and the aqueous layer was extracted with EtOAc (2x50ml). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with EtOAc (2x) and dried under vacuum to obtain 0.69 g of a yellow solid.

The total weight of 4-(1-cyclopropylpropyl)amino-3-nitro-2-pyridone was 2.20 g with a yield of 8195. , and shu-v,8 Gy), 7.33 (1H, 9U-6.9 Hz), 6.03 (1H, au-7.7 Hz), 3.18-3.24 (IN, t) , 1.60-1.74 (2H, t), 1.03-1.11 (1H, t), 0.91 (ZH, 0, 0.40-0.60 (1H, t), 0, 20-0.39 (1H, t).

Part B. 4-(1-Cyclopropyl)propylamino-3-nitro-2-pyridone (2.20g, 9.27 mmol) was stirred in ROSE (1 mL) at 257C for 16 hours. It was then poured into ice/water (220ml) and stirred until all

ROSIz will not react. This mixture was neutralized with solid ManHsSOO, filtered and extracted with EtOAc (xboml). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The crude oil was chromatographed on silica gel (100 g) and eluted with 10-2095 EtOAc/hexanes to give 1.91 g of 2-chloro-4-(1-cyclopropylpropyl)amino-3-nitropyridine in a yield of 8195. "H NMR ( 300 MHz, SOSIz): 7.96 (1H, and y-6.3 Hz), 6.58 (1H, and 9-63 Hz), 6.52 (1H, and 9y-5.5 Hz), 2 ,90-3.00 (IN, t), 1.61-1.82 (211, t), 1.01 (ZN, K.1--7.7 I tsu, 0.90-1.02 ( 1 H, t), 0.51-0.70 (2H, t), 0.21-0.34 (2H, t).

Part C. A mixture of 2-chloro-4-(1-cyclopropyl)propylamino-3-nitropyridine (730 mg, 2.85 mmol), 2,4-dichlorophenylboronic acid (544 mg, 2.85 mmol), dichlorobis(triphenylphosphine)palladium ( PI) (114 mg, 0.17 mmol) and barium hydroxide octahydrate (899 mg, 2.85 mmol) were heated in a dry flask under a reflux nitrogen atmosphere in dimethoxy (8.bml) and water (8.bml) for 1.5 hours After cooling, the mixture was partitioned between EtOAc (100 mL) and water (20 mL) and filtered through celite. The aqueous layer was extracted

EUDAs (2x50ml). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was chromatographed on silica gel (40 mg) and eluted with 3095

EtOAc/hexanes to yield a yellow oil; 1.00g, output 9095. "H NMR (300 MHz, SOSIz): 8.24 (1H, a 0-62 Hu), 7.87 (IN, ha 9-73 Hu), 7.43 (1H, 5 ), 7.34 (211.5), 6.71 (111.4 9-62 Hz), 3.00-3.10 (IN, t), 1.70-1.85 (2Н, t), 0.95-1.15 (4H, t), 0.50-0.71 (211, t), 0.25-0.40 (2H, t).

Part 0. To a solution of the product from Part C (0.94g, 2.57 mmol) in dioxane (26bml), water (2bml) and coprecipitated MNAOH (1.0ml) was added Mag252O4 and stirred at room temperature for 2 hours. CH2Cl2 was added and extracted. The aqueous layer was extracted by SNesi" (2x). The organic layers were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a yellow solid in the amount of 1.01 g. The obtained product was used in the next reaction without additional purification.

Part E. Amin p Chapinni I) (1.01 g, 3.00 mmol) was subjected to cyclization by refluxing in propioic acid (27 mL, 365.5 mmol) for 8 hours. After cooling to room temperature, 1M Mahon and 5095 Mahon were added. Extracted with EUAs (2 x 60 ml) and SNesi" (bOml).

The organics were combined and washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude oil was chromatographed on silica gel (40 g) and eluent 30905

EtOAc/hexanes to give a pale yellow solid (after trituration with hexane) in the amount of 520 mg with a yield of 4695. "H NMR (300 MHz, SOCI3"): 8.43 (1H, and y-5.8 Hz), 7 ... 81, 1.8 Hz), 3.40-3.50 (1H, t), 2.80-2.90 (2H, and 97.7 Hz), 2.10-2.30 (2H, t. ), 1.50-1.64 (1H, t), 1.37 (311, 19-:7.3 Hz), 0.87 (ЗН, 19-7.3 Hz), 0.81-0, 91 (1H, t), 0.48-0.58 (2H, t), 0.18-0.26 (1H, t). Elemental analysis, calculated for SgoNgiMzSi2: C, 64.18; H, 5.665 ; M, 11.23; found: C, 64.37; H, 5.66; M. 11.15.

Example 831

Preparation of 6-(2-chloro-4-methoxyphenyl)-9-dicyclopropylmethyl-8-ethylpurine

Part A. To a solution of dicyclopropyl ketone (50 g) in absolute methanol (150 ml) in an autoclave was added

Um4 Raney nickel (12g, dehydrated, in suspension with methanol) and then anhydrous ammonia (17g). This mixture was subjected to a pressure of 120 atm of hydrogen at 150-1607C for 5 hours, then cooled, and excess gases were released. The resulting suspension was filtered through Celite, and the filtrate was subjected to distillation to about a third of the original volume (atmospheric pressure, Vigro column). The distillate solution was cooled to 0°C, diluted with volumes of diethyl ether, and treated with a 4M solution of hydrochloric acid in anhydrous dioxane until the formation of a precipitate ceased. The solid product (dicyclopropylmethylamine hydrochloride) was collected by filtration, washed with excess diethyl ether and dried in vacuum (45.22 g, 306 mmol, 6795). IN NMR (300 MHz, methanol-da): a 1.94 (IN, i, 9U-29.3 Hz), 1.11-0.99 ( 2H, t),0.75-0.59 (4H, t), 0.48-0.37 (411, t). Mass spectroscopy (MNaz-OSI): t/e 114(5), 113( 100).

Chatisha B. A solution of 5-amino-4,6-dichloropyrimidine (5.00 g, 30.5 mmol) and diisopropylethylamine (12.0 mL, 68.9 mmol) in ethanol (100 mL) was treated with the amine from Part A (3.891 g, 25.8 mmol) and heated with an inverted refrigerator for 72 hours. The resulting mixture was cooled and poured into water (300 ml), and then extracted with ethyl acetate (2 x 300 ml). The extracts were washed with brine, combined, dried over sodium sulfate, filtered and evaporated. The residual oil was separated by column chromatography (30:70 ethyl acetate-hexane), and the desired product, 5-amino-4-chloro-6-dicyclopropylmethylaminopyrimidine, was triturated with a heated ether-hexane mixture, collected by filtration and dried in vacuo (3.15 g , 13.2 mmol, 4395). Tpl-137-1382S. TI S V; 0.17 (30:70 ethyl acetate-hexane). "N

NMR (300 MHz, SOSI3): a 8.01 (1H, 5), 4.95 (1H, Nha, .1-7.3 Hu), 3.45 (1H, a, U-7.0 Hu ), 3.37 (2H, Big), 1.06-0.94 (2H, t), 0.59-0.32 (811, t). Mass spectroscopy (MNzg-SI): t/e 243 (1), 242 (5), 241 (36), 240 (16), 239 (100).

Part C. A solution of the diamine from Part B (1.80g, 7.54 mmol) and 1 drop of concentrated hydrochloric acid in triethylorthopropionate (12ml) was heated to 100°C for 6 hours. The excess orthoether was removed by distillation (partial vacuum, molecular distillation). , and the residue of the distillation was transferred to the solid state to give the product, M-(4-chloro-6-dicyclopropylmethylaminopyrimidin-5-yl)-O-ethyl-propionimidate. "H NMR (300 MHz, SOCI3"): a 8.08 ( 1H. 5), 4.84 (1H, ha, 9-8.0 Gu), 4.35 (2H, Bi), 3.45 (IN, a, 9-7.7 Hz), 2.14 ( 211.4, 9-7.3

Hz). 1.41 (311, I. 9-71 Gu), 1.08 (ZN, i, 9U-7.7 Gu), 1.03-0.93 (2H, t), 0.58-0.27 (8H, t). Mass spectroscopy (MHz-

SI): t/e 327 (1), 326 (7), 325 (36), 324 (21), 323 (100).

Part 0. A solution of the imidaibo compound obtained in Part C above and p-toluenesulfonic acid monohydrate (50 mg) in diphenyl ether (1 Oml) was heated to 170° over 2 and one. The resulting mixture was cooled and separated by column chromatography (silica gel, hexane to extract the diphenyl ether, then 30:70 ethyl acetate-hexane) and obtaining the product, b-chloro-9-dicyclopropylmethyl-8-ethylpurine as a solid (1.42 g, 5.13 mmol, 6895 for two stages C and 0). Tpl-99-1002C TI C B; 0.26 (10:70 ethyl acetate-hexane). "H NMR (300 MHz, SOCI3): a 8.63 (1H, 5), 2.99 (2H. bi), 1.92 (1H. ri), 1.50 (ZH, 9U-7.3 Hz), 0.87-0.78 (2H, t), 0.50-0.39 (4H, t), 0.20-0.10 (4H, t). Mass spectroscopy (MS-SI): t/e 280 (6), 279 (36), 278 (19), 277 (100).

Part E. A solution of 4-amino-3-chlorophenol hydrochloride (18.6 g, 103 mmol) and sodium acetate (18.6 g, 227 mmol) in glacial acetic acid (200 mL) was gently heated with an inverted condenser for 12 h, then cooled and poured into 4 volumes of water. The mixture was neutralized by adding sodium bicarbonate dropwise, and extracted with ethyl acetate (2x500ml). The extracts were washed with brine, combined, dried over magnesium sulfate. filtered and evaporated. The resulting solid was triturated with heated ether; filtration and vacuum drying gave 4-acetamido-3-chlorophenol (16.1g, 86.7 mmol, 8495). Tale: 128-12920. TI C Vi 0.14 (50:50 ethyl acetate-hexane). "H NMR (300

MHz, 4:1 СОСИ3З-СО3О0): а 7.66 (1Н, а, У-8.8 Hz), 6.88 (1Н, а. 9-1.7 Hz), 6.74 (1Н. аа , 0-8.8, 1.7 Gu), 2.19 (ZN, 5),

Mabs-spectroscopy (NgO-(aS/M5): t/e 186(100).

Part of ER. A solution of phenol from Part E (14.6 g, 78.8 mmol), methyl iodide (10.00 mL, 160 mmol), and sodium carbonate (10.0 g, 94.3 mmol) in acetonitrile (200 mL) was heated under reflux for 48 hours, cooled and poured into water (800 ml). The mixture was then extracted with ethyl acetate (2 x 800 mL), and the extracts were washed with brine, combined, dried over magnesium sulfate, filtered, and evaporated.

The resulting solid was recrystallized from ether-ethyl acetate to give the pure product, 2-chloro-4-methoxyacetanilide (13.2 g, 66.3 mmol, 8490). Tpl-118-11"S. TS Ak 0.30 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIZz): a 8.15 (1H, y, 9U-9.2 Hu), 7 .39 (1H, Bgv), 6.92 (1H. y. 923.0 Hz), 6.82 (IN, aa, y-9.2, 3.0 Gu), 3.78 (ZH, 5) , 2.22 (ZN, 5). Mass spectroscopy (MS-SI): t/e 219 (19), 217 (60), 202 (40), 201 (14), 200 (100).

Part 2. A solution of the amide from Part E (10.1 g, 50.7 mmol) and sodium hydroxide (1 mL, 5 M, 50 mmol) in 9595 ethanol (200 mL) was heated to 507°C for 24 hours. Then, an additional 5 mL of the hydroxide solution was added of sodium, and the mixture was heated with an inverted refrigerator for another 48 hours. The resulting solution was cooled and evaporated, and the residue was partitioned between ether and water. The aqueous phase was extracted a second time with ether, and the extract was washed with brine, combined, dried over sodium sulfate, filtered and evaporated

The resulting product, 2-chloro-4-methoxyaniline, was purified by eluting through a short silica gel column with 30:70 ethyl acetate-hexane, and the eluent was evaporated (7.98g, 10095).

Part H. A solution of aniline from Part (c (7.98 g, 50 mmol) in concentrated hydrochloric acid (25 mL) was cooled to -57C and treated dropwise with a concentrated aqueous solution of sodium nitrite (3.80 g, 55.1 mmol). After 30 minutes to 15 ml of cyclohexane and 15 ml of dichloromethane were added to the mixture, and then treated dropwise with a concentrated aqueous solution of potassium iodide (16.6 g, 100 mmol). This mixture was stirred for 4 hours, then extracted with dichloromethane (2 x 100 ml). The extracts were washed successively with 1 M aqueous sodium bisulfate (100 ml ) and brine (bOml), then combined, dried over magnesium sulfate, filtered and evaporated to give a sufficiently pure product, 3-chloro-4-iodoanisole (7.00g, 26.1 mmol, 5295). TI-C B; 0 .39 (5:95 ethyl acetate-hexane). "H NMR (300 MHz. SOCI3): a 7.69 (1H, a, 9U-8.8 Hu), 7.03 (1H,

Bgv), 6.92 (1H, a, 9U-3.0 Hz), 6.57 (111, aa, .1-8.8, 3.0 Hz), 3.78 (ZH, 5). Mass spectroscopy (NgO-C/M5): t/e 269 (100).

Part I. A solution of the iodide compound from Part H (7.00 g, 26.1 mmol) in anhydrous tetrahydrofuran (5 mmol) was cooled to -90°C and treated with a solution of p-butyllithium (16.5 ml, 1.6 M, 26.4 mmol) in hexane.

After 15 minutes, this solution was processed

Part of ER. A solution of phenol from Part E (14.6 g, 78.8 mmol), methyl iodide (10.00 mL, 160 mmol), and sodium carbonate (10.0 g, 94.3 mmol) in acetonitrile (200 mL) was heated under reflux for 48 hours, cooled and poured into water (800 ml). The mixture was then extracted with ethyl acetate (2 x 800 mL), and the extracts were washed with brine, combined, dried over magnesium sulfate, filtered, and evaporated.

The resulting solid was recrystallized from ether-ethyl acetate to give the pure product, 2-chloro-4-methoxyacetanilide (13.2 g, 66.3 mmol, 8495). Tpl. 118-1197S. TS A 0.30 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSI"): a 8.15 (1H, a, 929.2 Hz), 7.39 (1H. riv), 6.92 (1H. a. 1-3.0 Gu ), 6.82 (1H, aa, 9-92, 3.0 Hz), 3.78 (ZH, 5), 2.22 (ZH, 5). Mass spectroscopy (MHz-ST): t/e 219 (19), 217 (60), 202 (40), 201 (14), 200 (100).

More frequent 20. A solution of the amide from Part E (10.1 g, 50.7 mmol) and sodium hydroxide (1 Oml, 5M, 50 mmol) in 9595 ethanol (200 ml) was heated to 507°C for 24 hours. Then, an additional bml of the hydroxide solution was added of sodium, and the mixture was refluxed for another 48 h. The solution was cooled and evaporated, and the residue was partitioned between ether and water. The aqueous phase was extracted a second time with ether, and the extracts were washed with brine, combined, dried over sodium sulfate, filtered, and evaporated .

The resulting product, 2-chloro-4-methoxyaniline, was purified by eluting through a short silica gel column with 30:70 ethyl acetate-hexane, and the eluent was evaporated (7.98 g, 10095).

Part H. A solution of aniline from Part (c (7.98 g, 50 mmol) in concentrated hydrochloric acid (25 mL) was cooled to -57C and treated dropwise with a concentrated aqueous solution of sodium nitrite (3.80 g, 55.1 mmol). After 30 minutes, the mixture 15 ml of cyclohexane and 15 ml of dichloromethane were added, and then treated dropwise with a concentrated aqueous solution of potassium iodide (16.6 g, 100 mmol). This mixture was stirred for 4 hours, then extracted with dichloromethane (2 x 100 ml). The extracts were washed successively with 1 M aqueous sodium bisulfite (100 ml ) and brine (bOml), then combined, dried over magnesium sulfate, filtered and evaporated to give a sufficiently pure product, 3-chloro-4-iodoanisole (7.00g, 26.1 mmol, 5296). TI C B; 0, 39 (5:95 ethyl acetate-hexane). "H NMR (300 MHz. SOCI3): a 7.69 (1H, a, uU-8.8 Hu), 7.03 (1H, rg:), 6.92 (1H, y, 9U-3.0 Hz), 6.57 (1H, aa, o-8.5, 3.0 Hz), 3.78 (ZH, 5). Mass spectroscopy (HgO-SS/M5): t /e 269 (100).

Part I. A solution of the iodine compound from Part H (7.00 g, 26.1 mmol) in anhydrous tetrahydrofuran (5 Oml) was cooled to -907C and treated with a solution of p-butyllithium (16.5 ml, 1.6 M, 26.4 mmol) in hexane. After 15 minutes, this solution was treated with triisopropylborate (6b, 1Oml, 26.4 mmol) and warmed to room temperature for 6 hours. The resulting mixture was treated with a 6M aqueous solution of hydrochloric acid (ml) and water (5ml) with stirring for 1 hour, then poured into water (100ml) and diluted with ethyl acetate (2x100ml). The extracts were washed sequentially with 1 M aqueous solution of sodium bisulfite and brine (each 8 Oml), combined, dried over sodium sulfate, filtered and evaporated. The resulting solid was triturated with 1:1 ether-hexane, collected by filtration, and dried in vacuo. The pure product, 2-chloro-4-methoxybenzeneboronic acid (3.05 g, 16.4 mmol. 63905) was obtained. Tel.-191-195260.

Part .). A solution of chloride from Part O (77mg, 2.78 mmol), boronic acid from Part I (77mg, 4.13 mmol), 2M aqueous sodium carbonate (4ml, 8mmol) and triphenylphosphine (164mg, 0.625mmol) in OME (20ml) degassed by a number of repeated cycles of pumping - flushing with nitrogen. Palladium (II) acetate (35 mg, 0.156 mmol) was then added, and the indicated mixture was again degassed and heated with an inverted refrigerator for 14 h. Then it was cooled, poured into water (100 ml). The specified mixture was extracted with ethyl acetate (2x100 ml), and the extracts were washed successively with brine (bOml), combined. dried over sodium sulfate, filtered and evaporated. The residual material was separated by column chromatography (silica gel, 15:85 ethyl acetate-hexane) to give the title product as a solid, which was purified by recrystallization from hexane (791 mg, 2.07 mmol, 7490).

Tpl--139-1402C (hexane). TI S A; 0.18 (30:70 ethyl acetate-hexane). INYAMR (300 MHz, SOSIz): a 8.93 (1H.5), 7.74 pn, a»sh-84 Gy), 710 (IN, a.1-2.6 Hz), 6.96 (1H , aa 9-84, 2.6 Hz), 4.20 (1Н, m BI), 3.87 (ЗН, 5), 2.97 (2Н. m bi), 2.00 (211, m BI), 1.44 (ZN, rg 9-7 Gu), 0.89-0.79 (2H, t), 0.62-0.52 (2H, t), 0.51-0.40 (211, t), 0 ,26-0,16 (2H, t).

Mass spectroscopy (MS-SI): t/e 387 (1), 386 (9), 385 (41), 384 (30), 383 (100). Analysis, calculation. for С21НазСИМаО:

C, 65.87; H, 6.05; M, 14.63; found: P. 65,77; H, 6.03; M, 14.57.

In Table 1, Table TA, and Table 18, melting point data, unless otherwise noted, correspond to compounds of Structure A.

TABLE of these viv girls girl i ve - va -

M MU We go M c. wa-x-x with v2-x-X | v2-x-u ay 2 Mi "M i M - vo V o ve ko Vo vi! 1 cues to vd Z (A (B) (S na aa a a eh p t E k v te t v" EE ra pe Tpya; -1 tn, sn, IC sy, se, n sv, sk, s, K, 128-129

E shko sv, i sn, sia, n sn, en, sv, 985-100 3 po sv And sy, sn, n sv, snu snssn, oil 4 pu SAT, n sn, st, n sia, sn, sin, a 528, sk, E sya, st, v s shen, s-Sd 143-155 in s sv, n s, sya, n sv, s, hay - 7 sn, sn, n SI, sn NI) sv, tn , pp. 68-71

In syu, sya, H sn, sn, n sn, sv, (sn., Osya, maslo a SIV sn, Pe sy, sya, n sn, sn, etc. 196-197 sn, st, N sya, sn, in sya, s Isn.y,-(03) "00 oil

Moss sv, n sy, sn, NI sn, san, ISNY-4025 "0 oil 12 tv, sn, in sn, sk, n sn, t. such sn), - sy, sk, in sya, sn, nn sn , 2nd, pp. 120-121

Mmoenuogts, o sia, si so o e-zh svi 205-210 15 Se, sn; E sya, sn, n sny, «--сН n 110-150 1E sya, sya, Н sn, st, ). sv ss e-SN 186-187 p sn sv H sn, sk, H sn, I sen, 121-122

18 sn, p. se E sya, sk, Kk sn, B 4-sv,-s,K, 48-60 21 sn, In. p sn, sk, is sn, in 4.-s,n,-S,H, - 22 sn, sv; in sn, sya, Kk sn, H 2-Isny-sN, - 13 sn, ge, KE sn, sk, x sn, n З- (SY s - 24 s t, E sy, sy, M sn, in (sn,)»OsYa, - 2 SY, l and sy, s, E sy, n ssssy, - 26 ty, Ii in s", sn, x sn, n s,d, 125-123 y! mon, s, E. sy, sn, Kk SN, n S.Ya, oil 48:n, t in sn, sn, E sia, Kk s,n, masle 29 sn, IR Kk cm, sn, E sn, snosn, snOosi, - sn, IK E sn, sy, E sya, s os,n, 91-93 with sn, hm, E sv, sn, Kk sv, n sny 120-121 32 pn, num m " st, sn, E sya, n o(sn,)7Oosn, che

Uh sn, Mi E sn, sn, n sn, snosn, sen, - 34 LY, 7E, IM pi s1 Kk n sn, s, oil ze sn, p, and NU si n n sya s, oil

In sp, t, n si si ts " son, stos, - 3? pp. Oth M Shchi. vi n n s,v, s. - z sn, ti K t. Ki n n sv, a-SY, oil id 118-119 (in) 125-126 ' (se 19 g, sn, " g si N n sn, sna - sn, sv, г s g n S.V, s, oil 11 ku g n her la n n s, (sun, OSYA, " 42 sy, sun, R s si N n San sen " 43 si sv N gi si N n sn, svi - with svv sv, n si su n n sk, svid - 45 sv, si, N nd si V n s. t, n t a in H s-s,8, sk oil d) sn, sn, n sx s n n s-s, s--s 158-157

Because you are, dream tsi a s1 n n n Hey oil 51 si In, Kk 1 si Н nn 1-,0U-S,5, oil and se gn, SHCHI si si Н n В 2-вг-сН, -

for SE, sya, V si s i i n 4-sn,- sv, 114-115 54 sv, sy, 2! 21 s1 g! n g 4-s,n,-C,H, oil 58 sn, sn, n si si n n K 2-5 -s, - 56 sv, sn, n s1 si in Kk n with hsy C, - 57 sn , sk, n si si n n v Isv,nOsn, - 58 sn, sv, n s si n v. g! snysu, - "a sv sv, n si a Kn k n sv, RY bo su, st Kk si si n k n s, -

S sia, sv, n si sa n n N sia, - 62 sn, st, " si si n n styusn, sniosn, - 5BU sia, sn, n s se V n sl, OSaN, -

Be sia, sv, n 21 si n n n os, -

I sv, sv, i si sa n N ia en, osi,

B sia, sv 9 si s1 n In snsn, sn, - 7 sia, sv, NI sy, osv, H sn, sn, sv, tia

BV sya, sna, H sna, osn, Нn sna, sna, sv, oil 69 sy, se, x sna, osv, n sy, sya, snusya, - 70 sia, sv, n st, ssv, n sna, sna , sun, - 7 st sv, n sia, sun, n sv, sleep ses-si, - 72 sn, sn, M sn, os, n sun, sin, sa - 73 sy, sv, n sy, sv, n s, S.V, sv, m 74 sn, sya, Kk sia, osn, n sn, sv, is, Osn, - 75 s, sn, Kk sy, osv, n sn, s, snsm - 16 sn, sn and si, Gaia Nn sia, siy svi - "7 sn, sn, n sn, sn, n sn, sn, (p. 192) - ta sn, sv n s. l N sn, s sn.nISNI, - 79 sn . osv, n s -OH, s - v s s nos sv nos es a-s, 151-169 83 sia, sn, x sn, o n sn, n s, 134-135 84 sn, siv n sn, sn, n sv, K 1-4201-s,ya, - 85 sn, sya, n sya, osn, Nn sy, n 2-VI-SK, - in sv, sn, n sn, osn, n syn, n 4- 2Hn,-s,8, and 87 sn, sv N se, sn, Kk sn, Kk 4 s.B,-sN, - va sn, sn, n sia, osn, n sn, I 2-1sn,-s4 , - 89 sy, sn, n syt, ost, H sy, n 3-(s,8,-s,n, - 9 sy, sy, x sy, osn, kn sy, BE (sy, sy, - 9 sn, sn, N sya, osv, n st, n stosu, - 32 sn, sn, n sn, OSI. Kk sia, Kk sov, -

93 SN. sn, N sn, ak, n sn, GE SN. -

Fa sia Iv N se, zn, n sn, n s - in t, sec N se, SN, n sia, cNosn, SN, OXYA, - 96 sn sn, n sv, osy, i sn, s osn, - 97 siesh sv NI sk, osn, n sn, n os, « cha sy, sv, n sk, osy, n sn, n oisVIz Osy, - 35 sn sv, k sp, ost, Kk s, stosn, sen, - 100 st sun, 1 sc, sun, n sun, n st 118-140 191 n sun, r se, sun, n sun, s sun, 198-199 103 n sun, E sun, sun, k sia, son, sa 142 -148 103 Ye sya, E sn, sn, I en, g. snsn, 140-142 104 n sn, KE sn, sn, n se, ek sen, nya

Ken n sv, Kk st, sn, n sia, sv s-SYA, - 105 in sn, E cm, sn, Kk st, san, S» - 107 ts sv, Kk sn, sy, n sv, s, sn , shk 108 N sn, KE sn, sn, n sya, s, isn, Osn, - 109 V sya, E sn, sya, N sya, s styu - n sv, IN sn, sya. Kk sv, on, (sny, 01 U - nia sy, N sn, sn sya, sk (sny) 1о2 - 112 I sn, chn sn, sy, n sn, sv, sn, sn, - 113 n sv n sy, ak n sn, ss, sv, - 114 m se nos sy, p sn, ses, V, snyusy, - 115 n sn, n sy, sy, H sn, s-S,N, sya, - 116 n st n sy, sn, H sn, e-s,H, s-s,V, - 117 V se, n sn, sya, H sn, n a . 118 Н sy, NI sn, sn, Н se, n 3-(ssho-s,H, . 119 N sn, K s. s n sn, n 2-Vg- s - 120 N sc n sy, sn, in sya, n 4-sn, s, . 121 n sn . 1p,-CH oil 14 n sy, in sy, sn, n sv, n Isnosy, - 125 n sy, " st, sv, n sn, n ss, - 128 n sv, ts sy, sn, n snu, n s,n, -

U and 7n, N sy, sn, N sya, Kk s,v, - 126 n sn, n sn, sn, n sn, k sv, - 129 n sya, n sy, sn, n s, strosk, sTOsN, -

Mo n sleep, n sleep, sun n sleep sun, sun, R 131 Kk sleep NO sleep, sun, Kk sun, n os,n, - 132 Kk sleep, n sun, sun, n sia, Kk sun. WASPS, -

u n sn, H sy, sv, N sia, snysv, s,8, - m4 n sv, NI s si H in sn s. - no sv, Ts gi si n v en, sv, t. 136 Nn sv " "1 s n n sov, sshchosV, - 137 v sn, " si si n n siv se - 138 n sv, Ks si Kk V with. s-OH, - 119 Kk sn, n gi si Kk n s, sia - 140 n sy, M si si n Kk sin, s,n, , 141 n se, n si si n x sv, Isn,,osN, - 142 n sv n s1 si NI Kk sv ss - 143 NI sk, N s pi n nn sn, ISN, 14501u - 144 n se, n "Ch sei n n sia, Isn,"-(023) 7 - 145 n sya, n s a n n siv, skusn, - 146 n sya, " se sI n n s-s,k, s.v. 1 n sy, nie si Kk n s-s,n, snOosn, - 146 n sn, Mn s si n Kk s-s,n, s, - 149 I sy, n si si n NI s-s.n, ss, . 150 sv, n si si N n n se - 151 Kn sy, nsi 1 nnn n zZ-(snyuo1-sn - 152 i sia, CI skh si n n n 2-VE-s,r, - 153 Kk sy, n s: se1 n n n 4-sn.-s, N, - 154 Kk sya, i s sa i N H 4-s,n,-s,Y, - 155 i st, N s si cy Kk Kk 2- sny, - 156 a sv, i si si i n: n 3-(cA) Sun - 157 i st, n s si n n N nisvu, os, - hv ya yan, Mk t a n yan n svyusy, - 159 N sv, N s. s1 N N n s. - 159 nsu, Kn her si n in n s,V, - 161 n sya, n si si n n n sn, - t no svono s s nia snosn, snyusy, - 153 n sn, v si s1 TSI n sya, os,N, - 154 Kk s n si si Kk n n os,v, - 155 i s n si a n n n se, OS, - 165 n st, n si si n Kk sn,Chsya, sen, - 167 n sn, n sun, sun, n sun, sun sec, - 188 n s n sv, osv, n sun, s,n, s, - 159 n s " sy, osv, n sn, s pines, " 170 N sn, K sn .

173 n s, no sv, "sn, tsi se, sp, tv 0. - um n sv, n st. osn, n ss s isny osn, - 175 n s NI sr, sia, M sn, sn, ssn - 176 N sn, NI sv, osn, n SN, sn, (sya) (01u i - 1" n sv, n sv, osn, n sy sv, sn, (02) - in n se, n sy, ost, N sn, si, sne - 179 n sn, n sn, ost, n sia, "--s, sv - 180 n sun, n st, sun, no s, sd, stosia, - 181 Kk sun, n sun, east, n sv, ss, s. - 142 n sv, cho "Y sk no sn, e-SZH, " - SDSH - 183 K se, NI SE, yen, N sy, n s.n, - 1855 nn sk, Kk sy, os, I sy, n 3- (sn, -s,n, - 185 Kk sn, N sn, sen, ch se n 2-vk-s,n, - 135 n sn, n sk, cm, i sy, n i-sn,- sn, - 187 n sn, n sy, osn, H sn, n 4-s,n,-S.V, -- 125 n sn, n sn, osn, i sy, n 2-1 -s.n, - 189 n sn, n sn, «sv, ch si, gi 3 -12, - s - iz n sia, n sn, session, n sn, n (ek, os, - 151 in sn n sv, osn, n sn, n snosn, - 132 n sn, Kk sk, ost, N sya, n sun - 193 V sk, Kk sk, osn, H sn, n Z - 194 R sn, I: sk, osv, H sn, n sei - 195 V sn. n se, osn, n sn, snpisn, sv,Ichsk, - yiv nos, 0noos, osv no sv s,v, osn, . 197 N sn, k SE, osv, NN sn, n «y, - 158 n sn, n sk, osv, n sk, n axis axis, - 133 n sn, n se, z, i eV pines, s schi 230 sn, sk, nossv, sn, n sn, sv, sv, 98-12 21 s with n sv, si, n sn, sv, sn - 202 Ш sn o N se, sn, n se, s, in, s, oil 703 sv, 2 n sk, sn, n se, s. st, osk, - 2 sn a n sp, sn, " se, s, en, - 205 sn, | no V sn, sia, H sn, sn «-«-V, - 26 sv, o n sv sn, N sy, sya, s, - 207 sv a Te sv sv, n se, sy, sn, - 208 sn, o K sv, sn, n sv, sen (Sv OsV, - 209. sn, o Kk sn, st n s sk snon - 210 sn, i) n sn, sn, Kn sia, sn, sni oh 211 sn, o n st, sn, n sn, sk sv - 212 sn, o n sn, s Kk sn, s, svmsn,, -

213 sv s n sn, s), n sk, se-sya, g . -, 214 sv, o Kk sn, si, i sya, p-8, snosya, - 215 sv o Kn sn, sn, and sn, «-s,N, siv, - 216 s o n sn, sn, y sn, e-sV, s-s, - 2 sv, Another n sy, s, "and sn, n sv, - p1vosv, s n en, sn, Kn sn, n 3-(sn,o)-S, 5, - 219 sv Ha) PI sk, sya, n sn, n 2-vh-sd, - 120 sn, o n sn, s", Kk sy, H 4-sn,-s,n, - 221 s o n sun, sun, Gesya, n 4-0, SK, - 222 sun o ns, sun, n sv, K 2eIsv-s, - 2:13 sv, s n si, si, n sv Kk 3- SI Suk - 224 sv, o ns s NI sv, n sstrosy, - 225 sv, y n sy, SI, ts sn, n stosn, - 216 sv, о n sn, sn, n sv, n sy - 227 sv o n sy, sk, n snu n sv at, 228 sn, o n sya, sn, i sv, Kk sn, - 225 s o i sn, sn, n sya, skfosn, snOosn, - 230 s o i st sy, n sun, sv, os, - 231 sv, a i sp, s, n sn, sv, os,n, - 233 sia, 2 n s sy, no sn, N osn, - osn, - 213 sia, s n sleep, sleep, and sleep. sis, p. - 234 sya, s in s1 "is N GI p. sv, - 2135 s o V s s n n s, s, - 236 s u g V s si i GI sv, snosy, - 737 sv, a n si s h n sl sv - 238. sv, b i sg, N Kk sv, se-sun, - 2139. su s n si si vi Kk sn, sn, - 250 sk s n sis s ia n s, sn, - 24 sn, a n si si iz Kk s, ISN.I OSN , - 2415 here at 2! si s n n sya, syasn - 343 sk o n s1 si n no sn, sn - 244 sn, o n s1 s Nn Kk sk (sn. (d) - 245 DCs o i s1 «1 n n sv, snynsy) , - 2546 su, o n si si N Kk s-SK, sia, - 247 su, (m N «1 s n n s-s stos, - 248 s, o n si si Kk n s-sZhK, S. V, - 24959 s o I) sa so Н n --СЯ, s-sv 112-131 250 sv s n s si n KE n s oh 251. sv, o ns s Kk n n 3-(sno-s ,K, - 252 sn, o " si a Hn K n 2-vk-SYA, -

253 sv, about this si si n NI n a-sn.s,, - 154. sn, g I. s si m Kn n 4-3, p 255 sk a n si s1 n K n 2-isv-s, , - i55 sk o n g -1 " n n Z-isan,- tn - 257 Sv, and Kk g 1 NI N n (sny aOs, - 258 sya, o n s1 t n n n n snyse, - 259. sv . n seosYa, sNOsYa, -

TEZ si i n no Sh "y Ne on Os,k, - 164 st a e s s1 N n n oon, - 255 sw, 2 n si si n n n sisn,.,"oSV, - 266 sn, 2 Kk х ч н н pines, sv - 257 s, 2 h sn, tn, in sn, s,n, sv, i 2568 sk a vi sn, pn, "Ch s s, sn, - 269 sv, o y sy, chn, n sy, S.V, snsn, - mo sk 2 ni t, pu TSI sn, s, s - 271 sy, 2 po-sv opn, n sv, S.V, a-s,8, 2713 sv, 2 N gy, SON, p st s, sen - iz se s h sv, Z n sv sv, sad, - mes i erotv i se sni, h1sn,1,osn, : 215 si, o i s, en , h sn, san, sny - 276 sn, o n p, pen, SHHI sv, S.V (SN)a-(01) M - 213 sia, o I sn, osn, IN sn, sv, iskiUog - tb sv o wn SK, In, ts sv, s, sini, - lz sv v! " Sk, osn, n sn, s-sN, s, - 28s sv a wn g, sv, n sn, s-s.8 . tn, n s Kk s, - 284 sya, Ge v sy, a n s n 3-(snOo-s.n, - 285 s o n sk, ost n sya, n 2-NI-sY, - 296 sn, a N pe Osn, n sn, n 4-sn,.-s,n, - 287 sn, o M sn, sp, n sy, n 4-s.n, sn, - 18 sn, o n sn, sesn . in sy, ss, M) sya, Kk syatosya, - 232 sv o p SIV ss, I sv, Ni siv, -

233 si, se ch se. (their N sy, n sv, t 294 sn, gn s, pa PI sy, n s. t 295 sy, s n s, osi i sya, snyuosn, snysn, t 296 sk s n yen, ee 15! s , p. sosE, se, - z00 sya, sya, sv, n s n n s-s,n, s-S, 106-105 391 cm, Ko N SE, sy, n sn, s, se - z02 sv, 5 n sv, e, Kk sn, sv s, " za1 sia, 5 n se, sy, n sn, s, sNOsn, - with sn, 5 in sv, t n sia, gn, sv, - 305 se, 5 ) s, SN, SHI SB, s, s-SK -. zob se, V n sv, Sn, n sn, s, S.V, - 307 tear E n sn, Se Z sya, sn, s, 7 308 sn, 5 n sn, t i se S, hundred sN, - 309 sy, 5 n sv, a, n sn, S sny - 310 sn, 8 n sn, ech n sia, s,n, Pi; vkrya" In Sho h 111 St., 5 Chn Sun.

Syn n sv, s, (sn, - 112 sv.

IZ k SE, si "n sv, p.

SNY, - 313 ih E in sy Chi n sn, s-s,N, s, - 314 s E and sy ti n su, se-s,n, stosn, « 315 se, and k sv, and n sn, s-s, s, - 315 sv, 5 Ni) sia, sa n sn, e-s8, «-s,n, - 317 sn, 5 Kk sya, si n sn, n sen, - 3195 sn, E n sny sy n sn, n 3-(sto-sYa, - 313 sn Z n sn, si p sv, n 2-vg-S,V, -. 123 sk, « n sn, Ne n sv, n 4-sn ,-S, - 323 sn, 5 H Sn, 7 n sv, n 4-siy-s,n, - 382 syn, 5 n sn, 7 n sn, n 2-isv-s,B, - 123. sv 8 these s", I: First st n 1-4s, 1-s, H, - 324 sn, 5 n sn, pa Hn s, n (eco sN, - 325 sn E H sy, E in s, n " Nesy, - 325 sv, 5 Kk sn, s. and sy, sn ns", syzhk ssosn, - 332 sn, B n sn, st, I sn, sn, os, -x 331 sn, 5 Kk sv, sn n st n os, - 132 sv, 8 Kk sia, si, but sv, n sten, osn, -

-

114 sc, 5 EE su si N nn B, sv -

315 sk Zh n a s n n sv st, .

zz36 sv, 5 ns s s n i sp svise, -

137 sv, - n si s1 n n sn, sa - z1ya sv, g H s1 sa Н H sn, 2-s,H, -

319. DES, 5 N si s n N sia, s -

130 s 8 n s1 si n n sn, sk -

341 p. 5 M si si n n san, (sno,osn, -

m st Bn s s nn s,n, snesk -

343 sv, 5 n ki si N n sn, (syu, i -

34: s 5 I) d1 si n N sia, sny o21 -

345 sv v n si si N n sn stmisnk,. -

zb sn, 5 n si is in H s-g, sn, -

3417 sv g: n chi si i I s-g, dream, -

348 sk 5 V si si Kn n s-sN, sov -

349 s 5 n si p N n «-sZhK, s-sn, -

z5a st, 5 Kk si s n Kk n s,n, -

zch1 sc, 5 nsi 21 n n NI z (sto -s,y, -7 352 sc, 5 n s Sh n n n 4-8 s

353 sk, is in si se n n I "-sN, sv, -

355 si E n si i n Kk i 4-s,n,-s,H, -

z55 st, E Kk s g n Kn n 2-(sn-s, -

356 sn, is En s1 l i n n 3-(sS.ny - s, -

397 sp, 5 n si s1 n n n (se.), OosN, -

zyaya se, E in se si N Kk n sEyusN, -

zch9 SV yes in s jan cn NI n sn -

zbo sn, in B si s n n Kk sn, -

zv1 sv, z n si sh n nn n s -

za s 5 n se a no no snosv, stosv, -

3563 si, z n « si n n sn, os.n, -

354 St., B g! si s M n H ss,V, -

zb5 sya, 5 n ",a sa n n in o(sn,),-osYa, - zve sn, U N se si i n snyuosn, sv, - z" sn, 5 n sn, Fk, n se sn sia , - iBv sv, 8 n s asn kn si s se, - 369 sn, z n sn, osi, n sy, sv, spon, - 370 sia, I hi! sia, osn, n sv sin, sv, - 371 sun, 8 n sia, ov n sun, sv, s-sK, - 312 sy, 8 and sun KV n sia, sv, Sen -

173 sv, B E s, osn, N sn, s,v, sv, " 374 sny, g in sn, Osn, n s, sn sny. OosN, - u5 sy, with Kk sy, osn, n sn, sn . Kk sn, sv, sne, - 319. syu E n sia, osn, o sy, 2-s,8, s -

ZO se, 5 n su, axes, N si, e-s, 8, snsn, - from sn, 5 n sn, sn, H sn, 2-S,N, sen, - 382 sn, 5 Ks os, n sv, s-s,N, e-s,N, k, 383 sv, 5 n sia, osn, n ss Kk sv, - 384 sn, and H sy, osn, " sn, n 3-10 -saN , -

U85 sn, 5 n sn, sen, and sn, i 2-Vk-s,n, - 386 sy, 5 n sn, osn, n sy, n 4-sn,-s.n, and 187 sv 5 n sk . n 3-gs,n sa - 330 sy, 8 Kk sy, osn, I sn, n (sn.)zosn, - 3914 sn, 5 n sn, osn, ts sy, n snposv, - 392 sn, Z H se . osv, n sy, xiaos, spos, - zo sn, 5 E s, sn, n sv, sn Osc, -, ke sn, 5 n sn, osn, n sia, Kk ss,ya, - 399 sn, 5 n st, Osn, n sn, n osn, osi, - 399. sya, v no sv osv h sv stvosya, s - 400 sk sn, N si si n sn, s,n, 5-sN, 153-155 491 sya . e-SaN, 187-184 4 sk, sk, se, sya, sya, n sn, nsk, oil av sya, syu, s sv sn, "n s ezh, sya, 98-99 406 sv, sn, sv , sun, sun, n sun, n sun, 149-150 4107 sun, sun, sun sun, sun, N sun, s. ,.osn, h 409 sun sun, sun sun, sun, N sny, svosya, sn, chsy, - 410 sya, sna, sv sx sn, K sya, sec, stos, ROSH 41 sna, sna, n sna, s AND N sv sna, - 412 sna, sna, n sya, s1 k n -sd sen, -

413 Sv, Sn, Kk se, g n n yee-s. s-s,n, 139-140 414 s, sn, kn sy, si N N sv, s,v. oil (Asi 415 si sv, her si, 1 k Kk sn, sn oil 416 st sia "y sia, si N n n sv, - 417 sv, sn, n sn, si n n s sis osn, - 18 sn, sun, n sun, si N n n Is osi, - 419 st, sv N sun, si n Nn sNyuosn, stosu, - 42 sia, sv, n sn, and Kk n san, pines, - 171 s N si sn, n H sun, sun, - 4:73 sun, sun, n si sun, H n s-s,n, "p - 4:13 sia sia V si sia, ni n e-suN, "e-sn 171- 178 a24 sk, sv n si s, NK n sya, sya, oil 425 sv sn, and s1 With sv, nn s,n s,n, - 425 sya s n si sy, n N ! si o, 427 sn . i s1 sk, n ns. 433 sn, sk, IN SI si n sn, s-s,H, sei, 194-195 434 sn, s, n sn, SI, H st, san e-S,С oil 415 st s s n sn, st n sun, sun, sun 155157 36 sun, SK, n sun, sun, sun, sun, «-s, sun, oil 437. sun, sun, N se» sun, st oil 418 sun, sun, Kk sun, osn, TSI n n a-isn,))-s,N, oil az sn, s n sn, sen, SHCHI n sv, s-sn, oil 440 sn, s n sn, osi, n p sy,. dream oil 441 st, sn, Hn s1 MM, n h sp S.V, - 44: sn, sv, n si Mne, n M s-son, sec, - 443 sn, sn, n si Mme, N g s-S ,N s-sUN, - 424 sn sk, n si Mne, n n GE: sov, - 445 sn, sv Kk si ne.

N n s, "sa - 446 sn, sv, Kk sa Kn, n nn n sin, - 47 sn, sv n si kne, N n s.n, sn osn, - 488 sn, sv, n si Mane, NO n n sni osi, - 443. s, s, n si Mme, n no snosk, snusv, -z or sn, sn, N si mm, n n sk, sN. osi, - 451 sn, sn, Kk sn, Mne, Kk n sn, with M

452 sn, sc, TSI sn, MM, n n s-s.N, se - 153 st, sn, n sa, mme, v n s-s,N, -«-SЖ, - 454 sk sy, n sv , Mmekh, n N ns - 455 sv, sk, n sn, "me, n N sv, sv « 456 sk, st, h SV, zva, in n x sv, - 157 DSK sn, N sn, Malya, AND.

N sia, (sn,,osn, - 458 sk, s n sn, kMme, v n ni ysni sy, - 1559 sn, sn, no sv, im H po stvosn, snosn, -7 "va sn sn, n st Kme, n n s.v pines, - 4b1 s, s Mme, SK, st n sn, sn, s, - 462 sya, Sk, MMeh sn, sn, n sn, s-g, sv, - 453 sn, sn, Mk sn, sn.

K sn, se-san, e-sS.N, - 44 sc, sc MMme; sv sun, n sun, Kk s,n, - 4565 sv si.

Mmme SV, sy, N sia, san, sn, - 456 st st, Mme; SV, sn, n sv, n s, -- 467 s sv MMme, s, sn, p sn, sok (sny ALL, - 458 ost, sv, not sn sv n sn, Kk (snu sv, - 459 s, sv, me sn, sy, and sn, snosv, snos, - it sb s obme, sn, en, Kk sn, sn, svyusn, - 411 stv s, Н sn, s and sn, sn, sen, - pi sy sv, n sn, gy, n sya se-S,8 s,n, - 473 sy sv, H sn, sn, Kk sn, s-sy, s-s,n, m 474 sy sia, H sn, pi . . ,оссВ, - axes NE, n сн, с NI. ск, сн, сносн, - 48: hundred св, н сн, си, нс, сай, с, - 182 ся, св, н сн, с, н сн . - 495 sy, sn, TSI) sn, sv N se, sn, s - cha sya, sv n sv, sya, Нn sn, n sen, t, 487 sy, ss ich sn sn, n sn, sn (sn. i)osn, - ava sy, syn, n sn, sn, and sn n (sn,).ose, - 489 sn, sn, n sya, sn, Kk sn, snosYa, snosE, and 450 svo sv, N sn , sy, n sy, sn, pines, - 4131 p s, Iii sy, sy, h Nn s s, 96-97

492. SE, sn sn, SE, n I: e-s,i siv, - 493 sv, sn, Kn sv, se, V K s-s,H 2-s,n, 493-159 494 st Fo n sn, gu, n I: KI sya, 99-100 495 sya, sv Kk sv, sn, N n sya, s, - 496 sn, SV, Kk sv, sn, n yn n s,n, - 437 sn, sn, n sn, sy, N N st, East axis, - 496 sn, sv V sn, sn, n N n (sny, osYa, - 499. sn, s N sia, sn, n n drifts, stosn, - pp sia, sn, n sy, sia, n N sk svosn, - 501 st, si N sia, sy, N sn, sn, s,n, - 502 se, sn, N sk, sia, Н sn, sn, s,N, oil 503 se, sn, Kk SE, sy, K sn, en, s oil 504 sn. sn, " sk, sy, in sn, sn, svOos,, - 06 sn, sn, I si F n n sk, sn, maslo id, sv) 507 sv, sk, n s1 s in Kk sv, sk maslo bo sya, SV. si si, N si St, " n sv se--s, oil (A) 28-45 (B) 116-117. (s vi» sun, sun, n si SE, n nn session, s-sS,H, 145-145 513 sun, sia, E si SE, n n sv, s.n, oil 5-4 sn, sv, n s SE, n Kk s s,n, oil ziz sia, st, in si SE, Н n sn, sn,og,, - 5iv sv, sn, E osn, g Н si sn, s-s,v, - 527 s, s k osn, s n s session, s-S.N, 883-189 5a sn syu n os, sa N si sv, s,d, 109-110 iz sia, sn, Hn osN, s1 N si sn, sny Osn, - 522 sn, sv noosyu, s n si soya, snos, - 821 sn, sn, N sya, sy, nn sya, | pp. s 115-140 52x se, v; N sya, Ka EV n sn sv, s,N, 2 521 sn, sy, N sti Ga n s, s,n, 938-191: 524 s sy, N sv, osn, TSI N en, s,n, maslo a sn . , s,n, - 528 sya, sn, n si Se, nn n sn, sn, oil 529 sn, sv n s st, Kk a sv, sv, - "zy sn, sv, noov o s n Fo s s ,n, sun, 129-131 vzhh sun, sk n sun, sp, n sk sia, sun, sesy, 77-85 517 sun, o n sia, st, n sia, se, sny z, - 533 sv, sun , N si si ih! n sn, (sn,), SS, - 34 sn, sya, n sn, ost, n n sk, nese, - 535 sn, sya, r. osya, sn, V sn, sn, sn) Nsn, - 3 sv, sv, n sv, si Kk Kk sv, (sen, - 537 sv sn, n sv, sn, sn, Kk sn, "sn NeV, - 538 s sn her p shk, n in ot (stvsn oil 539 sv , sn, B a CE, V s sn, blue, - 540 sn, SK, in osn, si H s1 «sn sne, NK 541 s sn, n sy, en, n sn, sn, s-S,H, 118-127 in syap» o M sn, sk, Ks sn, s«-sy - 843 sv, syu, kn si s p n sya, s-sy, butter 544 sy, sn, M sn, osn, and n sn, ss, oil 545 sp st Kk osn, sv, n sy, sn s - 46 s n sn, s ts n sn, s-S,H, - 547 Shsk sn, n si tn, sy, n sn, s-s,H, - 548 sn, sn, n si ev, n n sn, "e-s oil 5495 sy, sn, " si sk, n - sn, t-sN - 550 sn, sn, Kk sen, s n se sn, se-sn, - 521 sv, s, n sny st, Kk sv, sya, sv, oil 552 SE o I sn, s, Kk sn, sy, sy, - 553 sk, sn, N si et K n sya, sv, - 554 SV, sn, Kk sn, sesv, n n sn, sv, - for sv 7 n Goa I sv n sv, sya, sv, - vav s si, Kk SN, Ki n n si si, - 557 si, sn, n sn, si, sia, Nn sia, sn, t, sia, st N s Se, N n sn, s butter 539 si si in "1 ss, K s st, sn, - zba se, sk k osn, si n ii st, sn, - 551 sy, s n sn, sy, n sv, s.

Sa 192-103 562 sv o M sn, sk, no s sia, Sun - 5653 sv s n 1 pi N n sya, sa - vich sy, sv ya sv, os, N n sya, s, naslo 265 sn, sn , n osn, sn, and sn. sleep, sleep -

5Eb5 sk, sv X sn, g N ns, SNU - 567 en, sn, n sia, "Kk, st, n sy sna - 5eYa stu sc, n si SE, n Kk sn, sv, - 559 s en, " s sk, n si s sy. - 570 im siv n osn, 1 i s1 S.Y, sn, - 571 syu sk n sn, sv, n sya, sv, ethos" naspo 572 sn, o ps sn, n "s, sv, s.vogsn,, - 573 sn, sn, n si g1 n n sn, sno (sn,, - 574 s sv, n sn, asn, n n sn SOS, t, "75 sv, sya, these osn, sy, n en, s, SUO SY, ) a - "tb sv, gy, IN 2n, gi k n sv, SUK Osn, - 577 sv, sy, "y sn, sy, sy, i san, so (sV,, - 578 sk, sn, n si skh, n n s.n, SOSNY - 579 sv, Sk, n si s, n si s, sno(sn,, -

ZB:n, sn, n on, U n s1. sya, svasn, n- 51 s, sy, i sy, ti, N sya, p.8, s.osn, oil 582 si, z n sn, sn, n sn, s. s.vOsn, - 583 sk, sv, M s1 si n n sn, s.osi, - va os, SN, ch sia, osn, nn sn, sunosn, - cha5 se, V, nese, sy n sn ... n s1 sk, v n s", SV OsSY, that 5va st, sv n si St n s sv, suyavosi, - 59o snu sn, n osn, s n si sn, s,Oosn, - 591 p. sv i sv, "p, n sya, K "-S,eshchone) oil (sn), 5a2 sk, p ch sy, sk, n sv, n s-s, NisniOne) - sya), 293 sv sn, NN si si n n n se, nysN(Ome) - (sn). 594 sv, sn, B sn, «sn, nn nn and s-S,NSN(OMe) -

East, 595 sb, sk, n sun, sv, n sn, n s-m) k (st, 596 sn, sn, n sn, 1 in I: n s-S,H,SN(OyMe) - (sn ,, .

SNI , 599 sk, sn, Kk si SE, Kk s n ss, Oome) -

YSN.z

Bai sk, sy, E osn, 1 n s Kk e-S,H,SN (OM) -

ISI

BO: SV, sn, sn, si s i n s sn, - 502 sp, sv si, s si n K s-s,N, s, - 60 s, sn, sya, s ha and K. ss s- SK 155-156

BOE sv sk, sn, si si " Kk n S.V, - bo5 st, s, s s s n n s,n, sia, -

OB sn, sn, sya, si gi N n n s -

For? st sv, sk, si (0! Tsi. n sv (sn, Osn, - 608 SN, sn, sn, shchi S n cy sy, s, -

BO sv, se, sn, si s1 N N s.n, sn, - vii s, se, si, si si Kk n s s, t, 63 sv, sv, sn, osn, sn, n si, sia, dream, - 512 sn, sn, st, sun, sn, n sn, s-s.y, SAN, - 613 sn sn, sk, osv sn, I sya, s-s. s-s.n, - bis, sn, sy, osn, sn, " sv, n sid, - 615 s sv, sk, osn, sy, and sv, sv, sv, - 516 sn, s sn, sv, sn, " sya, n sn, - 67 si sn, sya, ots si, n sn, sya, Isn,rOsN, -

Bin sn, sn, sk, osn, s, n sn, sia, siy, - biz sn, sn, sp, osv, si, and sn, sn, s,v, - 520 sy, sn, sy, osn, sn , Kk Sun, Sun, Sat -

Ba. sk, sy, sy, st, Kk n sn, s,n, « tush sn, sy, sn, o in N s-s,K, sn, - 623 en, SN, sy, sn, os, n e- sK "es, - bv24 sp, Os, sy, si osn, NI n Kk sk, -.a 625 sn sya, sna, osv, n N s.N, "kv, - 5256 sn, sv, sia, sn . , sv, sn, o. N n sn, sn, - 630 hundred sn, sn, sn, os, nn sid, s. - bi os sv s, sv, si n In sv s - 632 sn sn, sn, sun, si n n s-s,n s - 633 si, sn, sn, sia, si n n s-s,H, s-SW, m 634 sn, sia, sv, sn, s n i ns, k, - 535 sv s sn, sn, s " n sv sv, -

636 Snu In vesk, : n n n S.V, - 517 sk, In, "y, sn, 1 k n sia isny sia, - 38 IB sia, s sk Z N N "n, sv - 619 sy, sn, SM, sn, : n n sy, sy, - va sn, se, sn, sn, shchi N N s s,V, - 541 sy, sn, sn, sg1 t, n nn sad, sia « 642 sn . n sv - 645 sn, Osn, sy, 1 g, n n s, sv - choose sp, vty on, s1 in, : Н N s.ts, - 547 "p, "7 sn, si , in i sv, isnu,OsN, - vaya si st, si g, nn sy, s, - 519 TK, In, sa y v is! sleep, sleep, -

Barya sn, sv, s1 x, n Kk san, s, s- 51 "n sn, sn, si I-y n si s. s - 552 sn, six si I, n h s2-s,n, sn - 651 sn, sn, «v, sy g. - bo Kn, sn, sk si and n si n sn, - 57 yeyosv, sy, sk ;, n skh sv, Isn, Osn, - vv sv pr sy, s1 and n a sn, sn, - voz tn, p sn, si t, n s sn, s, -

Because tp, sn, ev, sk1 still n si sy, sn, - 51 sv, "7, jan, pt | n si s, San . 262 bV, sn, sn, osn, y n g s-s,, sv , - without swap, sya, es, I Kk a s-SYA, as, - ev sn. sn, st, sn, and Kk si | sv, - 665 st sn, es, I Kn s s. sen, -

BOS sv, «sn, ps, , n a n sv, - 657 si sv sn, osv, and N gi sv, IstrOsy, - i se osv, sv, osva n si sn, sia, - vBa so s so n a sn, sv, 7 570 st sv, st, osv, and KN si sv, sn, - yo s st, sn, (v n ns s, - 672 sv, sk, sn, sv, hl, I: | "e-s, s. - 573 yen, sy, s sy, s n I: | s-s,y, -sYa, - " 74 sn, sk sn, sn, en, nn n sd, - 675 sn , sn, SK, s she n Kk sk sia, -

vtb tn, sn, sk, sya, Sho i N n S, -

BIT sn, sn, sy. sy, p, n in SA, (sny ZOosn, - boss Osn, s sn, s, and K sn, sk, - 66 s sn, sy, sya, s n n s,n, s,N, - ba sk . 109 b sk, sn, V s1 sx, Still si siv, - - 69 s, sia, n sn, S. sn, in st, sn, - 85 g sv, H sn, SV, Ii n --S,N , s-s,n, 11-03 vyab sun, 00 sv n sun, SI and si, s-S,Y, s-s,Y, 187-188

YeeVvT sn, sn, n KI ST SCHI h se-s,N, sn, - baya s, s, and sn, s sa n e-sn, s2-s,n 119-121 689 st, sk, i" sn , ve N n ya sn 108-109 "bo sk, sn, ci osn, Xia, n s n s.n, naslo 651 sy, sn, n s1 si " si n st - 52 s, t, n s 3 SY , N Ge sn oil 593 s, su, p sn, o, i E --С,Н, С.В, oil 634 SE. sy, i osn, si i sn, s-essn sn, - uche sv sy, n si s n y «-Sa sn, -

BE s sa, n se Se sn, I «-sN, p.8, - 97 sn, sn, n sn, sl, nn sn, sn, oil

BE s sv, n osn, Sy n se, sy, s, - 659 Sv, sy, I si (its n si sia, s.n, - 700 sa. s i sn, Se sv, v sn sia, m 7 sv a TI so, o. n v s se - 102 en, s. m osi, s n sn, s, sn, - 7013. st i n s S "y a s,n, sd, - 704 sk, 5 ) Kn s i. -s.N - tot sn, o n s1 sii n si s-sn, sh-sN, - tav SI, o n sk, sn s, n s-s,n, s-y, - 79 sn o Н sn . . st -

76 sy, I. and sy, sy, sy, n s-s, K, s - toast with her sy os, Н Н sn, sk, I - the sn, o n osn, s, m sy, sya, sd , - 715 sya, 2 n si SE, n si sia, sv 7 7 kn, g Kk sn, sk, sv, n sn, sn, - 721 sn, sn.

KE sn, sy n su, s.n, sSNISN,), 145-147 122 sy, sya, n s1 si i ,V sya, sis), - those sn, sv, N si sv n n s. ss), - 724 s, sv, N si se. n v sya, segsk), oil ti5 sv, sya, v! sy, SS NO n sk, ss). oil 725 sy sia, n si si NI n s, siaISK,), - 727 sn sv, n SE, k1 n n s ss), kaslo 778 sy sn, n sn, kg in n sv, SS, - and C sn , n SE, Su and! n s, SNISN,) - 7599 st, sn, V si skh I N sei, sVISN,), - tob, sn, v si g g H sn, snisyu,), - 7" sn, sn, n si (s s in sn, ss, - 733 sp. s n sv osi, I N sv SNISK,)a R 734 sn, sn, n sn, o. g H s,v, sNIsT), - 75 sn, s, n s1 se , Н sv, SsNiSY,), - te sn, sn, kn si S ikh i s,y, sn(sn,), 737 sy.

SN, Ya si sh KE n sn, svi, - 73B sn, s s: si Oh, gn siv, sNISsN), - 735 se, sn, ts si o, E n sv, sNtsya,), - 740 sk, sy, n si o, sn, n sv, sishsy,, - 7241 sn, s, TSI sia, o, sg, V Siy snisn,, - 14: sy, sn, n se .. gi In s.n, snIsn ,, - ta s, sy, n si TI osn, H sv, snsn,, - 754 sy, sn, Kk "a sk osn, Нn s, snsЯ,), - 745 sp, sp, " sn, s: osn , n sk snsn,, - 746 sy, se, n sn, s ov, nn SON, SNISN, 1z - tatost, sv, M sn, s. but sv, sv s-sv, 140-143 748 sk, sy n si skh I: n s, s-s,H, 102-108 (A) 75-82 (s; 745 sya, s n s1 sk i n Hediy se-sn 105-108 750 sn, sn, n «i 0 n n s, e-s, 8, naslo 151 s, sn, and sn, oh, n p sk, s, naslo t5a s, sy, N si (3 Kk n sk, 2e-s,, 108-109

753 sv 5 n SE, s K n sv, s-ey, oil aa) 85-97 (2) 754 sv, s, n sn, s N N s,N, e-sy, 87-58 t55 s sv, n Se, SE, n n en, s-s,8, - 756 st sv H 21 sy in Kk en, e-SN, - 757 sn, sv, n se si IZ n sk, sn, - 758 sn, sv N si a si Kk sn, s-s.ya, -. 759 sv sn, n sn, osn, E n s, s-s,n, - 760 sn, tn, n sn, osn, si in sn, «sv, - 761 sn sn, n si sv, E n s, s-sv, - 763 sn, sk, n si SE, s n sia, s-sd, - 753 sn sn, n s1 SE, E Ii s s«-sV, - 76 sn sv, N s1 oi a ns , s-sv, NO. 755 sv sv, n s osn, gn sn, s-s - yBB ste sv, n se osy, syu, N NE, s-S,W, - 767 sn, SB, i s, Feb sv NN ev, s -s,j, oil 76ja sv, sv, n si n sa n sn, e-S,N, . 759 sn, sv, n sei «s osn, nn s, e-s - that sv sv in se s, osn; H sun, s-sd, - 7th sun, sa n sun, s sun nn sun, s-S,H, - 774 sun, sv, n sv. sv osn nn sya s-sN, -- tis si, b, n sn, sv NN st sn, sti ta5- o te sn, s Kk si si n n sn, s. - 775 St. Sun. Nn s se n n s, v, sn, oil 779 sya, sv, v St, s n Kk ov, si oil 750 sn, sn, N si, si n Es sv se - 781 sn, s N se, se, N Kk sv, sn, - 782 sn, sv, V si Fk n n sia, s,n, - 3 sv sn, n si si E v sia, s,n, - 7854 sn, s n si sa s n sia . Sun, Sun, Sun, Wed, Sun, Sun, Sun - yours, Sun, Sun Wed, Sun, Sun, -

730 g, sn, n s1 osn, s1 | nya s, shi tii sno «v n si on, E n sin, s,n, i 792. sn SN, p s1 osn, sv, | with Sun, - 793 Thu, V n Sk, St Sun | s sn, naslo 794 sya, s n s1 n si in g sp, - 795 sya, sv, n Ka sa osv nn sv, s,n, - 796 sn, sv, n si sn, osv, sv, sv, - 737 sya, "(v n sna, s osy, nn sna, s,n, 798 sna, sv, Kk sna, sna, osn, NN sk sv, - 799 sya, sna, n sna, SYA, sna, |: S.V, sn, naslo 800 sya si n se, s n n n k-snuyun sn, 138-139 801 sia, sv, n se, a n n s sUN, -sv, 138-139 80: sia, si , nn SE, s in nn s. session oil

IAI

122-129 and Pe 803 p5, sv no se, si n n sn, s-sya, maslo vo4 sya, s n SE, sa n n sya, nai maslo o sya, s z! SE, 71 n Kk sn, with maspo

I: Y. KN in SE, s n Kk sn, san -

But? Sun, Sun, Sun, Sun, Sun, Sun, oil

Won s, sn, n sn, si " n s, s, H, wax oil, sn, n Se, "s " n s.n, sv, yao sia oil, sv, n si s n n n M 4- sn,o-s,n, - 411 sya, sn, n si sn n n e-s,V, s-sW, 180-182 812 cm, sv n si sk n n sp, s-S,V, -

Viz sya sv, n si st n NI sya, s-sV, - 814 sn, sk n s1 F n n sn, se, - 815 sn, sv, K sia a V n sn s. o: 86 sn, sv n se cm I: n se, ka - 817 st sv, n s sy n i sv, p. - vi8 sya s, n si sk N Kk sun, s,n, - 819 s sv n si s n n sen, s, - 820 sia, sv, V SE, se, n nn n 4-sn.o-s ,n, - 521 sia, sn. n Se, SE, n N s-s.d, -«-S,N, 145-250 822 sya sn, N seE, Sv, n n sia, se-s, - 823 sv sn n se, se, Kk n sn, s-s, N, - 824 syu sn, n sr, se, GE n sn, syn, masle 8235 sn, sk, n st, se, Kk n sn sia, - 826 st sk n SE, sv, n n sn, Sens -

827 sya, sa, with Se, SE, and I sen, sv - 828 sya, sn, n Yev, se, "y n sn, syn, . - 825 sn, sya, N SR, st, N n sn, sn , - 830 sun, sy, n si ost, N n n «-sya, o-s,, 58-50 v31 se, sv n s osn, N n e-S.N, «-sn, 139-140 832 sya, sn, n su osn, N n sn, e-s,n, naslo 833 sn, sn, Kk si en, N n n -sV, Oil 834 sya, sn, Kk s1 SS, Kk n sn, so, oil 835 sya, sn, p sa osn, n| sya, st oil 836 sya, sn n si osn, y sy, SN oil 837 sna, sn, v si osn, n n sen sn, oil 38 sn, sk, n si osn, n n sv, sn, oil 835 sn, sn, i sx osi, E I s, sn, oil 840 s, s n si s1 E n Kk 4-snOyu-sn, - 841 sn, sn, H s1 si E Kk --s.M, e--S,N, 148-144

For syu sv N s1 si E ns s-S,H, - 8413 sn, sk, ns su EK n sn, s-s.N, - 844 st, sv, NI s si g n sk, sn, - 845 s sv n s si EK n sn, s - va sv, st, Kk s« si E in sn, sy -, 847 sia, sv V si s E n sv, sk, - 845 sn, sia, n s1 s E I; sn, s,n, - 849 syu, sn, n si a E Kn sp, s - as sn, sk, NI si si gi n Kk 4-sno-sN, « v51 SE, sk N s g si Kk "- S.N, s-S,N, - 82 sk, sv n s s s1 Gu sp, 2e-s - 853 s, sv, i si si si N sn, ss, - yaza sya, s Kk si si sa No si, s.n, - 855 sn, sv, n si si si Kk sn, sv, - 856 sn, sn, n SI and si n sn, Sena - 357 si sv n si sa s1 n sn, s, - z58 s, si n "1 si s Kk sv, s, N, - 859 st, sn, n si s si n S.V, s, - vva sn, sn, H sn, on, RE n n 1-st- s,N, -, 951 se sn, z! sn, osn, E n s-sN, s-s8 128-12! vb2 st, sv, n sya, osk, E n sin, s-s,n, - ve sv, sn, n sn, osn, E n sya, "-2.8, - vve s sn, n sn, ren, E n sia, sn, -

Veya se, st, n sv, osv, E I: sya, sn, - yaBb sya, sn, n sv is R n sya, su -

827 SK, sk, E sn, ost, Z n sikh sv -

VBYA osya, sv i sn, sn, E N sn, sv, - like sn, sn, n sn, OS, E I! sv, s, - i sv sv, n sn, os, si N n 4-s560-s,N, oil visn, sv, ns sv is n s-s,y, s-SV, 179-181 872 sk . 874 sv, sun n sv se N sun, S.V, - 815 sun, mon, n sun, Sun, si in sun, s, - 8756 sun, sv, KE sun, FC, si N st siv - 877 tn, sk, E sya, osn, s: in s, s. -. vta sn, sv B sch, osE, si no s, sn, - 8793 sn, sv KE s, os, si N sk s - all sv, Es sn, E i n 4-2po-s,n, - 881 sya, sn, n s1 sn, E n s-s,n, s-sn, 130-131 vva ss o0No0s1 sko sp s-sv, I vaz sn, sc, n si sy, E n sn, s-2. N, - 4 si sv, G s si, E n sn, sia, - vv st, si, N «h sv, E n sn, savae - vaye sn, sv, n si sv, E V sn, so - 887 sya, sk, n s sn, EK n siv s - vv sov, Kk si sn, E n sen, s.n, -

U sn, sn, tsi i sya, E i sya sya, - 832 sn, sn, Ks se, s n n i-sno-s,v, - 89) sn. sv, n si se, s: n e-ShN "-s,8, ". 852 sy, sy, E si se, p n s,k, e-sZhK - 093 sn, sy, v si sy, spi n sne, "e-sh,N, - vza sn, sn n si se, si ( In sun, Sun, - 895 sun, sun, n s1 sun, si n st. - 895 century BC, n si Sx, si n sk, sk, - 899 century BC, BC, Kk si se, si i s, sya, - 900 century SN, SN, Kk sia osv, k Kk n sd, naslo 01 century SV . , n a sv, E n «-s,V, «-S8, - 905 st, sn n a se, E N sia e-su, -

Fo6 st, sv, Kk s sv, E n sn, e-s, H, -

906 , Kk si St, E n ev, sn, . 91 sun, sun, n si se, E N sv, san, - 912 sn sk Kk si SE, E NN sad, son, - zla s sp, Kk si axis, si n i 4-sto-S, - 314 sia . e-сН, - 916 сн, св N с осн, сх n сн, s-сН, - 917 сн, сн, n с оси, с n св, с, - ziv sya, sk, Kn s osn, si n st sya, - 913 syu, sv, n e osv, s1 n sk, sna - 920 sn, sv, M s: osi, s N sn, se - 921 sk t n s: os, si NI s, s,V, i 922 sn, sv n si osk, « n sn, s, 7 923. sn, su, n se osn, E in n 4-sno-sn, - 924 sia, sv Kk sv esv, E in s-s, v, s-s.V, - rz sny sv, n s osn, E n s.n, s-oN, - r sv, sn, Kk s osn, e n sv s-S8, - 927 st, sv n si osn, E n sn, sv,

b2E sv, sv n «t osn, E I: en, sa, - 929 sn, sv n s: osn, E Kk sia, sv - 919 sv, SV, n s osn, і n se sv, - 931. sn , NE, v s osn, E n s,n, s,n, - 932 st, sv, gus osy, E n sv, sya, - 933 s st, n s sia, sia, n p 4-sp, -s,y, - 34 st, st v t ost, son e-S,V, e-s,H, 150-151 935 st sv n si osn, sia, VN siy, s-s,H, - 935 syu sv, n si osv, s N sv, s-S,K, there are 937 sv sv, N s osn, su V sv, s, - 938 sn sv, n si osya, VN sv, s,v, - 939 s sun, n a osn, s NN sya, Seny - 9490 sn, sv, n s sv, sv, NN ov, sa, - 941 sn, sv, i a osn, sv A sv, sv, - 942 sya, sv, n si os, syu N sia, sia, - 935 si si, n si, osn, sn, nn 4-sna-s, - 945 st, sv n si, os s, NN s-SOK, s- 148-151

with. svo sv no sv os sm sy, St. maslo vav sx, se 0000 sv, osv syu SN s ih Y

Phys sx, sp, 08 o0osv, osso si SN sy, sen and to syu sv, I 00sya, os, su X sn, p. and ovi syu sv n sn, osn, st sn sn, su, masyu 52 sn s n sy, osn, sn, Kk s, sn, oil 53 sn, SV, V si N s Kk n 4-spo-s 7 954 s, s n se I si n s«-s s-S,8, 151-153 55556 SE, sn, n si g! si n so «e-s,V, -7 kv st sk, n si n svn sia, s-s,i, - in? st, SV, n si Ya p 1 n si, en, - ty sia, sk, n si n s1 n si, san, - 59 st, sk n s1 n s n sia, sna - vo sia, sv Kk si N si I: sia, art. - 964 sn, GE, n si and sen, n s-s,V s-s,N - che sia, NE n si se os, nn sk, s-sv, - ve cm, NE n si az ss, NN sk . 969 sn, sn, tsi s Ki osn, g sn, Seny b 973 sn, sn, Kk s1 si os, kn sn, sa, - 71 sn, sn, N si si osn, nn s,v, s,n, 938 sm, sm, n si a osn. nn sn, sv - tu sm, sya, N si syu osn, KN Kk 4-sno-S,H, .« 979 syu, snu, n si syu osn, NN se-S,8 s-s,8, - 975 s, sn, n si s, sn, n S.V, s-sN, - 76 sn, sn, n s1 sv sv, n sv, -- - 977 s, sv n si sv sv Kk se, s, . 78 St. Sv. , osi, K SN, s,N, - 982 sia, sn, I si se osv i sn, Sai, . 983 sn, sv n sn, si osv M n 4-snuo-s,H, 7 94 st sp H sv, s osv k ey e-s,B, a

Св сн, св, В сн, с сн, я с,в, с-с,В, - 986 си, св, n сн си осн нн са, е-с,н, -

yav: st sn n sn. c1 ost I sn, sv, . ev sk, sn n sy, 71 osv, E sn, eyi - 989. syu sn, Kk sy, si osi, Kk sia, seni - 9930 syu, sni, Kn se, si sm kn si, SV - 951 st sni, Kk se, si osn, Kk sn, sn, - 992 st, sv, n sn, si sn, Kk sia, s;y, - 995 sv, sn, is, sia, ov NN n a-sto-s,n , - 894 с св Кк сн, сн, ос, к с-С8, е-с, - з55 сн, st Кк сн, с, са св, с-сВ, - 996 са, st n сн, с осн КН с . osv, nn sn, sp, - 399 st sv, n sn, s. os NN si, se . 1000 sn, sn, n sv, s, in vn sn, sa 7 1001 sya sv, n sn, s sn, M sn, s,n, i 1002 sk, SV, p sn, sy, os, N s sn, - 1003 st, sn, n sn, ost os, n n «-sno-sd, butter 1004 sn, sv, n s, os, ost, V s-sV, sov, 138-140

T005 s, s n sya, os, os, NN s, e-F,n, - 1005 sv sv, i sy, osv, os, VN sk, s-S,8, . 1007 sun, sun, n sun, sun, sun, sun, sun, - 1008 sun, sun, Sun sun, sun, sun, sun sun, sun, sun, - 1009 sun, sun Sun sun, sun, sun, VN se, sna - 1012 st st v sya, osya, osya, vn s, sk - t011 sv, sv, n sy, osya, osya, V sya, sv, . 10192 sya, sv n sya, osn, o, nn sin, sya, naslo 1013 sya, sv, n s1 osn, osn, Vn 4-sto-s,n, - 1014 sya, su In s1 osn osv NN e- s,, s-S,B, and 1015 sya, sn, B si osn; osn, V sv, e-s.N, .- 1016 sya, st n si osn, osn, sv, s-s,n, - 1017 sn, s n s sv, os n sv, sn, - 1018 sn, sk, n si osn, osv NN sun, sv, - 1019 sn, sv N si os, os, NN si, sini - 1020 sn, s n a osv, osv, V s,s, sa, - 1021 sia, syn n si osn, osk, nn en sn, - 1022 sv, sk, n si ov in B: sv, s, - 1023 sn, sv, n si OSE, nn n I. 1-sna-s.n oil 1024 s sn, n si OSE, n n s-s,N, -e-s8, 119-205. -

1021 sn, sv Te s1 OSe, n is sn, sn, oil 1028 sya, sy, E s1 OSE, n ia sv, s. oil 1029 sv V N si SSE, n N s, snu - 1039 sya, sya n Ge sot, Kk n s, sa, a 1031 sv, sn NI s osv, n n s s, - 1012 sv, l Ni si os , her n s.y sn oil 1033 sn, st n sh o, n n H 4-snyu-s,n, -

Me axes, s n s, n N s-s,M, se-s.N, - 1035 sn, sn, n si BOR, n n s,n, 2e-s,8 - 1035 sp, sv, in ! с SE, n H сн, с-сЖ, - 1057 es, I! s zse, in H sn, s, - iiy3a sya sv, ! sia OT, ch g! sya, sa - 19039 sn sn, Kk si BE, n n sy, Ga: And we eat s sn, Kk s1 that, Kk n san, sn, - 1041 sy, sv, n si B, y n sn. dream, Ne 1042 St, St N Si Be, Kk Kk on, dream, . io44 sn, sk, n sii SE, and Kk n 1-sn,a-s,, 105-107 1045 sn, sn, n SE, o IS Kk e-s.N, «es, 159-159 1045 sn, sk, n si oz Kk i s-g, a-S.n, 130-132 1047 st sy, M SE, ven, and k "-s.K, "e-s5 - zvo eko0Ogy, 2! si SN, n n es e-s,8 - 1069 sia, sk V st, sov, n n e-S.N, 2-S,N, - 1355 sia si H s1 sosn, n n s-s.N . sv, n s se, NI n n 4-sna-sv, 113-115 1054 sk, sv, n sv zhk n n n 4-sno-s,, - 1055 «s sn, E osn, osni, and 2- 0. s-s,N, 129-153 4056 sk si n osn, axis Kk nn san, w-Tssh,V, - 1057 sn, sv, U o ost mk NK se, s-s,y, - 10595 sk, sv N st, Osn, n N sk, s, " 1059. sv, sn, n ost, osn, NI n sn, se 7 1060 sia, sv, N osn, osn, NE n sn, Se - 61 s Z, n os, osn, n n sya, s, - 1062 sk, sn, Kk osn, osn, n n si s. - more osv osv, I osv, ov, i ns, s, - 1065 st, sn i ov St, n y k 4-svo-s, - 1065 sv, sya, K ost, se, n n s-sv , se-сН, 158-159 x 1065 СН, сн, Kk ost, Se, I I: сн - - 1067 сн, св, no осн, св, н n st, с-СН, -

166 sy, s, kooosyu st, n y sy sy 7 zib65 sn, sv, E osk, Se, p Kk si sv - iy7j0 sia, SE Kk osn, SR, n n sv, sv. - 1071 Sun, Sun, N osk, SR, nn n sun, s, - 1012 sia, sv Vesn, se, W n sv, SV, - shShsta sun, sun, n os, se, n n s, sik, - 194 sn st, n st, ok, n H and 4-sno-s,n, oil 1075 sv, a! nn se, osn, n n 8-S,H, s-s.y, 123-130 1075 sv sv n sg, sya, g n sin, e-s, 1154127 shield sya sv Kk se, osn, n Kk sn . k Kk sun, Se - 1081 sya, grades Kk SE, osn, n K sv s - 1042 sya, s, Kk se, osn, Ge and se, sn, naslo ibiya3 sia, sv, n se, osv, n n sia , sn, 71-78 1084 sk, S, Kk osn, si osn, and n 1-sta-sn, - 10858 skh, sy, and osn, s osy, n s-su s-m - 1095 СН, sn, Kk osn, s osn, s! WITH; s-s,n, " 1097 sn, s, KE axes, s ost, n s --s - vva sn, sn, Kk osn, sg os, g sk, sv, - 1089 sn, s n Osn, si osy n se sya, - 1095 sv, sv, n sya, sye sya, nsk, syny -. 10914. СН, сн, Ch osn, si osn, N s, sv, - 1092 sn s n osn, a sen, n sl, sn, 1093 sn, sn, no is, sa stv kn San, S.V, - 1094 DC /sV, sv, n osv, sn, osn, H n 4-stvOo-s,H, - 1095 СН , st, n osn, sy, osn, H ss, s-s, - 10956 D sv, sy, n osn, sy, osn, I s,n, s-s - 1097 sn, sn, H ssv, se os , In sv" «-с2,Н, - 098 sk, sn, M osn, su, osn, N si, sn, - 1999 "sk, sn, n osn, sk, osn, n sn, s, - 1100 sn , sun, n sun, su, sun, I) sun, SA - 4105 sv sun, I! osya, sn, osn, NN sn, «y, - 1102 sk, su n osn, sn, osn, V sn, su, - 1103 siy. s N osn, s os, NN. sn, s, - 1104 sk, s n osn, sk, osn, H 4-sn-sA, -sh mob sv s, "o os sk ovya s-suK a-sy - 1106 SN, si, " osn, SR, osv nn s --SW, - 1107 sk sia, KE osn, SE, osn, n sia, e-SUN, -

Uyuya sv sn, IN os, st, osv, in sv s I - 1109 sk, s ks sv, os, AK sy, s - 1tso s sv, ns sv zho nn sy, s - 114. sv s, i es se .

M4 dream sv, but osv, si osv, n n i-sna-s,n, - from sn, sv, I: Yahno M sya os, N s-s,N, s-g, - im st sv, kov si sv I am St. p. p. 8, - to her? sx, sv, n sk si osn, NN sn, s-s,8, - iiya sv sv, n osy, st osn, i b, sn - 11419 sn sn no osn, se osn, /N s si, - 1126 s, sv, n sun, sy s, sn s - 1121 sn, sk NI osn, s sv v sya, san, - 11293 sv, sv nn sn si osn. nn sun, sen n- 1123 sun, sun, I sk, si os, sn, sk, - 1124 sv, sv i osn, osn, osya, (Ya n 4-SBo-SD, - 1125 s, sv i osn. осв, ос, НН сс с-сВ, - 11285 sk сн, n осн, осн, осн Н en, --с,Н, - 11257 св, сн, хо од, сн, н сн, «сн, - 1123 se, sv, but osyu, os, os, NN sun, sen, - 1129 sv, sn, in osy, sen, osk, nn sn, sg, - 1130 sn, sn, NI osv, sen, osv, n sia, sna - po sia ev Ki osn, sia, in VN s, sia - 1117 min, sn, n osn, sn, os, ns s,H, - 1133 sv, sv N osn, osv, os NN on S.V , - iz sp, svi sya, s gi sya, s, svoho,sy, 119-411 piz st sn N SYA, sv, n sya, su sn,sya, 134-135 1136 s, sv, s svno sv s sei mo-mi1 1137 sun, sun, Kk sun, sun, n sun, syh sia 142-147 1138 B sv, n s1 si n n sov snOOsYA, - 19 sv sia, n si si n n s sk sv, - 1140 sv, se, n si si n n s, skktsi - cha si Fu, n cha «s. sk st. sno5o,sN, - 1147 sv, sv n si osv, n N sya, sn,sYa, -

114a set, p, v. s1 on, Kk Kk si sn1 - 1149 sf su, n si osn, x Tsi s sim - 1155 CM, sn, n st, osYa, n p sk, -syh maslo 151 s si n si se, n N se, s . ost, CI n syv sh-s,H, - 1155 sya sk M si OS, N n se, sh-Suc oil 1155 sia, "V, » si sn, n n sia s-g, 115-125 11547 sn s n se, osn, n H sn s2--SD, oil 1158 sya, osv o 0/N si si nn ks, --s,N, maspo 11589 sv sv n se, osn, s n sen, s-sN , - 1169 sv, sn, A si, sv, E N sn, se-s,V - 1161 sv, sv a s si IN n a-k-s,K, s-s,K, oil 11562 sya, sv n sn, os, sv In ahv-s, s-s, ih 1165 sv, sv n s sv, PI n 4-E-S, s-s.n, oil 1154 st, sn, in 21 OSY, N n a-vE-s,n, s-s, - 1165 sk, sv, n su OSE, V no 4-v-SD, s-B5N, - 11656 sn, sn, yan si sy, v in 1-ke- SN, s«--, t-, 1157 syu sn and SE, sen, nn 4-k-s,v, is--.8 - 1166 sia, sna, V s 1 no sia, 4-E-SЖ , «-С,Н, - 1169 сю св, в сн, сен, си n 4-в-с.д, -с-сН, - 1170 ся, св, н с, св E no a-k-Сщ, s-s,y, - 1175 sy, sun, V si s1 Kk Kk sia, se-s.N, 109-15 0 1172 sun, sun, sun sun, sun, sun, sun sun, th

Mao sia, sv n s se, I ia sia, e-s.V, 135-117 1174 sv sv n si sen, n NI sn, s-s.n, - 1175 sia, V n si osv, N n s.n , s-S,n, - 1175 st, sn, n si sn, n N sia, "e-s - 177 s, s no osv o bvo Kk k si -e-d, - 1178 st, s n si s k sia, sa, e-s,v - 11793 sn, NE, |) sn, osv, s VE s e-g.n, - 1180 sv, s i sv ev E n sn, e-s,n, t 1182 SE sn, V s1 s n N s. 2nd - 11825 st, sv V sn, axes, sn, n s, s-s,n, - 1183 st, s, n a st n n s, s-s.8 t 1184 st s n ti os, N N sya . n sv, s-s, B, -

tav g «tsa shchi gi gi Kk sn, Ha s-s,n, ' iiz33 OSJ 7, n sa, osy, and I s, s-s, - 11923 sia, sv, " sia, osv, E K son, "K.V, - 1191 sch, sv, H s p I and sp, --sH, - 1192 sn, en, H sn, osn, sn, and sn, s-s, . 1193. sk, sy, VN si SR, in N sina e-s - 1194 Ggsk, s n s1 osn, K Kk sv se-sn, - 1945 s sy, n si OSE, n n sn, ---pV, - 1195 sv, s, n s1 sn, N n sn, s--s I, - и19: sk sv, Kk SE, ots, Н n sn, s-s, - 1198. sk, IC, Iz SI gi N sv, p,8, - -S.N. t, 1199 s KN, n si, oS, si n SW, se-s,n, - 1250 sv, t n si, os, E E s, p-khan - 12812 V, sn, n "and S I V p. a-S,V - 1202 sg sn, Kk sy, s:n, tn, H s-s,N, p-ssh, ni 1201 tn, sn, I chi sg, і n sh -S,N. se-s,ya, - 12594 sn sy, Kk s1 osn, Kk H "-s,M, e--, - 1205 sn, s, k "s s-g k Kk s-S, N s:sn, - 1206 sn, sn, n ki sn, M Kk "pan se-s,k - 1237 ev, sya KE se, osv, Kk Kk mon-s, s-sn, - 1208 st sv, N si si I sv, s-s,K. 8-siN - 12069 sk, "V n l osn, "1 K e-6,H, s-s.N, - 1210 sn, st nn sn, sn, E Kk sk-s.N, s-s.N, - 12m11 vp, g nn sn, g I) i-s, su 63-85 1212 b, osv, i osa, p n i 2 -S,M, s-sK 152-184 1213 sy, "V, n osn, l nn n sp, e-s - 1714 sv sia, p osy "1 y n s, ss - 1215 s sn, in osn, 1 N B si, s-s,, - 1216 st, sn no on, lu m n sv, sia, - 147 st sv, N osn, p N W s.N, s, - 1238 sv, SV, N osv . -sto-s,N, - 1222 sv, s, Kk osn, sn, n yk s-s,.V, s-s,n, oil 1223 t se, n sv, S, n N SK ss, " 1224 sk, s nn sn, sn, n n sv, s-suv - 1325 sya, sv Kk o, s n n sn, s-sK, - 1226 sk, sv, n ost sy, "y I sy, s,n , shk 1277 sk, sun, n osn st, n N sen, sun, -

1229 s, EM, and osv, sk, n E sn, s « 1543 st sk N oS, s, N Kk mon, sen, - 230 s, sn, n osn, sn, n i sn, sn, o 1251 s sn, Kk osn, sn, n n N a-stons, - 1232 st, sya, no osi, Fe N E s-bN, s-sW, 176-178 1233 sk, sv, N osn, Osn, n E sd , "d - 423 sn, "NN, n ren, OSI II G- sn, s-s2 - 1235 s "8 Kk osya, osn, V Ye sia, 2-s.y, - 123656 sn, SN, NK ost , osk, N Is sn, sn, - 123? syu sn, Nn osn, Osn, N E S.A, s,N, - 1238 sn, st k ost, osn, n KE sv, sn, - 1239 st, sv n OS, sk, n E sia, sen, - 1240 sk st N os, sk, I E sv, sn . 1241 sk, sy, n ost osyakh, " E n k-snuy-sN, - 1242 si sy, n se, e n n 2-s, se-S8B t 1243 st, sn, N Se, E n n sn s -С,8, - 1344 с сн n se, Е В н с, se-suM 115-156 1245 с, с, с, n SE, Е в н си, с-с.н, - мия сн sn, n se, E I: ch sun, su - 1247 «sv, st, nK se, Ye Te ns Sun, - zlav sv, sn, n se. g n i Sen, SV, - 1243 sv si, N sg, g i n sv, sya, - i" sv, sv, n se, E n ni sn, sa, . 1251 s sy, N nev, E NI n Kk a-sno-sSeM, 57th 1252 S sy KE se, E NI yin vlosy, vposn, Oil 1253 С, сн, N SE, E n вкс сн, sk 119-120 1254 сн, сы, W Ст, и NI n с. ся, 115-119 1235 св, сн, E си ОСя, v n sn s-S,N, naslo 1255 sv sn, I: s Ot, E n sn, sii, oil 1257 sv sya, n 1 SE, KE n I svesn-snasn p3-v5 1258 sya, sn, p SE , svin n n sesN, 2-st, 163-165 1153 DC "8, st n "Ta s Lu n sn, -sZhK 3245-46 1260 st, sn, N sk, s NI n e-sya, e-sy . N s s-s, - 19564 s sn, in SE, os,n, Kk nn s SU - id65 s, sy, n se, Os, EV u sya, sk, - 136 6 si su nsk, os n n sen, sun, - 1287 t.

SN, n st, os, H, and n sy, s, -

1255 sya, sy n SE, osi i a sn, sn, - 1259. SN, sn Kk Xia, osn, nn n a-sno-s,N, - 1284 si su, n se, on E ch «ss k -s,H - t2v5 sp, sn, i sia, sp E H s.V, -e-SK, - 1286 st sn, H sn, Ge E n S.V, --s - 1287 sy, sn, H SY, s t Hn se, s-s,H, - 1286 s, sn, and sy, o E H sn, sya, - 1289 sn, sn. n sy, sya: e n san, se, ny 12953 sn, sya, I am, a. eE Kk sSyun s. - 1231 s sia, Kk SY, s e n s.n, san, - 1252 s si n sn, s E n sn, sk - 124 s sk, Kk sn, sn E k K a-sn, Cho-s, H, - 1294 s, sv, I sn, don, sv, NN sn, s, 101-102

Mzheya sm, sn, N st, osya, en, N sn, Sleep, oil

I295 СН, sk, N s s n n s, 4-so-s,n, oil 1297. sv SN, n t: SI M s sv s, 113-135 1998. D SN sya n s gay "y sn, sya, sn, 123-125 12959 sy, S n (g s in sv, sn, sn, 125-127 1306 s sia and g «1 NN st sei, es 157-159 1101 sp, and n st OS, sn, n ge-s.n -SsSK - 1301 sn, o n s sk, p N sen, e-sN 143-150 1303. s o NI si osn, Iz N st-s ses.y, 124-155 13094 sn, o n s R. " I! e-pPu s-s,v, - 1195 sy, y: Kk t: sya, n Kk s-s, s-s,V, - 1108 SV, s Kk set, osv, n Kk sto, s-g, - 1307 sv o Kk sg g! k sn, -e--, s-s,H, - иZ06 sn, o Kk sn, osn, s kn s-s ss, - 1309 sk , a n sun, sun, E n e-SYA, e-s,N, - 15:0 sun, Ha! sk - 1112 sy, Ge) n Si osk, n y sy, s - 1313 FV o n gi ost, n Kk sn, sn - 1314 sn n Kn 2 sn, n g sya, sya, - iz s a N SE, oS, n K sn, sn, - 1315. si a N si si osv sn, SN, - 1317 sy, o N si, OSI, 1 Kn sn, sn, - 7 ziv Os, a Kn sv zh t n sv, s, - 1319 sn, SV, N s si N n s.n, sk oil 1320 st s K si si n n sv, sv, oil 1321 SV, sn, i si si n Kn s-sN, 2-sn- сН, oil

1122 sun, sun, " s s ch n se snISNDYUNI, kasloe 1323 sv sya, nsi s Mk se son, o maspo 1124 sk, sn, n ki1 s nya s. so kaslo 1125 s V n s sg n n sk, elephant oil 4396 sk, sn, Kk sv, osn, s n n 2-s1-6, H, oil and 127 sn, sv, kn su, osn, si I: n 3-21-s,, oil 1328 sn . ) n z-sn-S., oil 13231 si sv, Kk sn, osn, si N n 1-si-s,, oil 1332 sv, sv, Kn sn, osn, si n n 4-82p0-S,H , oils 1333 sv, sv, n sv, sn, t I n 2.5-(spokaslo sep, 13134 sn.

N SE, osn, s1 Kn ih 2-sna-s,N, naspao 1335 sv, sy, N si si n vsk s-se maslo 1336 st sn, What si pi n tsi. sn, sis, 96-97 1337 sn, sn, kn s1 s n v n spioniistyosv oil 1118 osn, sv, Kk se skh NN V n speonIsn,s,n, oil 1139 l 7, Kk ih si n n i isshcon, n, oil 130 t sv, and si s1 Kk no sn(snu), s(01-1- 154-155 letrieiipui

1343 st, sv, n si si n v sv, so,su, shaslo 1342 sv, sya, Kk si g n Ni st, seo,sk, naslo 1123 p. sn Kk «1 1 k Kk sn, sk kaslo 1544 sn, sv K skh s Kk Kk sp, pine, myaslo ita5 sv, sn, K s1 si ni i n 2-s21-s. 115-152 1ME st NE, i s1 gi i i H 3-s1-s,8, oil 1487 se, sn, N si s n i. n d-v-pN, 545-149 1344 sya, sk, n si s n nn n 4-sn-S,, 199-700 1345 sv, sn, n si si n n G.V 4-S1-sYa, 183-184 1150 SV, s n sii t" n nn se-2y, s-sSYA, -

1151 sv, si, Kk sn, osn, sn, i a-S.K, -N, -

1352 sya, s K s1 se, n n s-sn, se-s,v, -

1353 St., Sun. n n k-su, e-s., -

ii154 s, s M s1 OSE, n n -sv s-sn, -

1355 sn, sy, n si sn, nn s-s2,H, s-s,H, -

1356 sn, sv, n sk, es, n n se-SV, e-SLy -

1357. sn, sv, n gi si n spj "V s-S, - xx 1158 st, sv, V sya, zhk a Kk -sK, s-S,Y, -

13595 sm, sm, Kk sy, o, ' n 2-5 "-SY -

115O SE, SE, n ou IN, , H 8e-2V, e-s,y, - 11651 ge, sv N Gi g, e n s.n, se-s, - i362 ZV sy, n s1 on, E n s,V, son, - 1163 sya, sn, n chi ssYa, E | sn, "-s.N, - iz64 sya, sv n si osv E N sv, s,N, - 136: sya, sv N si ss E n s Sun, - 1366 st s NN aooo ok NO. sl, san, - iz" sya, s, n si OSYA, Z n sv, sn, - ii368 sv, su, M skh osv, E V sv, sia, - 1365. sn, sya, n si osi, E n r 4-sto-s,v, - 1379. bV, Su, x st, sv, I: in sn, s. oil and 371 sv sia, n "1 "1 Kk Ge! sn, 2-sn,-a- sC, oil 117 l sv Kk «E, osn, sn, n sv, 2-CH- es, - 11112 sn sv k se st, Н E sn, 2-sn, s sya, - 1174 sn, sn, n si gen, n nn sk, ask i-s-sYa, not 11753 sv, sv, n si OSE, n K sk, shesnu ss, - 1376. Yu SN, sn, n si sia, Kk n st sn, s-s , - 1377 "V SN, g! sg, osn, n n sn "-Sny- tys - 1378 sk, se, G:! si si n se sv, 2-sn, o-s, - 1375 sn, sv B sn, osv, si n sv, 2-sn,-s s, - 380 sk s N is s1 In Kk st, i-sn,- ss, - t13yai s t, n si si N n sy, 2-snua- s,V, - 1182 sv, se n se, osn, sn, n sy, sis, - 11383 sn, sy, Kk 1 "a n H sn, 8-23, - z3yaa sn, Н, n si osn, H in sv, gonu on, - 1183 sya, sv n g tet, vn V sya, a-s-2-98, - 1386 sya, SV, in si sn, V N sv, 1-s.,-s-oD . sya, sv, n sia, s sei n sv 2-s,- ss, - 1390 sv, o Kk si si n Nn su, 3-siv,-e-, - izya1 sia, s is h s1 Н H sv, o p-2" - pyridyl and - e2-С.Н, і3z32 sn, sv, gy sy, осн, сн, я св, и-1а- -. pyridyl 1- s-m 1393 sk, sy, n si se Kk n si, 4-2" - pyridyl 1- h s-uy, 1394. sia, sn, n si osn, E Kk se, o4-- - pyridyl 1- s-sk

1395 sya, sv, N si OST, N her sn, o 2-0- - pyridyl 1- e-s, Y 1395. sn, sn, yes si sy, n n sn, I " pshridyli1- . so, 1337 sn , sn, E CE, osn, n H sn 2-2" - pyridyl 1- "-s,y, iz9v8 st sv, Kk si c1 n sn, sn, 3-a- - pyridyl 1 - ss 1399. sn, sv, and sn, sv, si and sk, aa - pyridyl 1- e-S.N, 1400 "sn, o n gi si NI N sn, ,2-0- -" pridiya!1 - s-s,B ,

Key: (a) For compounds labeled "oil", the data are given below:

Example 3, spectral data: TI C V; 0.27 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.90 (1H, 5), 6.95 (211, c), 4.45 (1H, ri), 4.27-4.17 (2H, t) , 3.85 (1H, ad, 9U-9.5, 4.8 Hu), 3.27 (ZH, 5), 2.94 (2H, a, 9-7.5 Hu), 2.56- 2.46 (1H, t), 2.32 (ZN, 5), 2.06 (ZN, 5), 2.03 (ZN, 5), 1.37 (ZN, i, .1-7.5 Hz), 0.85 (311.5 9-7.5 Hz). Mass spectroscopy (MS-SI): mp 355 (3), 354 (25), 353 (100). Analysis, calculated for SgiNovMaO 5NgO: C, 66.46; H, 8.23;

M, 14.76; found: C, 67.00; H, 8,10; M, 14.38.

Example 8, spectral data: TI C V; 0.34 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.89 (1H, 5), 6.95 (2H, 5), 4.46 (1H, Bi), 3.41-3.933 (1H, t), 3 .22 (ZH, 5), 2.94 (2H, a, 9-7.3 Hu), 2.93-2.85 (1H, t), 2.84-2.69 (2H, t), 2.51 (IN, BO, 2.32 (ZN, 5), 2.30-2.20 (1H, t), 2.04 (6H, 5), 1.37 (ZN, i, 9-7 .7 Hz), 0.84 (ZH, i, 9-7.3 Gu).

Mass spectroscopy (MH-SI): t/e, calc. for Sg2NzoMaO: 366.2420, found 366.2400; 369 (3), 368 (27), 367 (100). Example 10, spectral data: TI C V; 0.13 (ethyl acetate). "H NMR (300 MHz, SOSI3): b 8.93 (1H, 5), 8.10 (IN, 5), 7.96 (1H, 5), 6.96 (2H, 5), 4.39 (1H, Bi), 4.24-4.14 (1H, t), 4.12-4.00 (1H, t), 3.20 (1H, Bi), 2.80 (2H, a, 97 ,0 Hu), 2.78-2.68 (1H, t), 2.42 (1H, Bi), 2.33 (ZH, 5), 2.13-2.04 (1H, t), 2 .06 (ZN, 5), 2.03 (ZN, 5), 1.933 (ZN, i, 9U-7.5 Hz), 0.80 (ZN, i, 9-7.3 Hu). Mass spectroscopy (MNag-SI): t/e, calcd for Cg2ZiNzoM7: 404.2563, found 4042556; 406 (4), 405 (28), 404 (100).

Example 11, spectral data: TI C V; 0.60 (ethyl acetate). "H NMR (300 MHz, SOSIz): b 8.92 (1H, 5), 8.51 (IN, 5), 6.96 (2H, 5), 4.78-4.68 (1H, t), 4 ,57-4.47 (1H, t), 4.32-4.22 (1H, t), 3.43 (1H, ro), 2.81 (2H, a, 9-6.9 Hu), 2.78 (18 BO, 2.43 (1H, Bi), 2.33 (ZH, 5), 2.10-2.00 (1H, t), 2.07 (ZH, 5), 2.03 (ZH, 5), 1.32 (ZH, Her, .1-7.0 Hz), 0.78 (ZH, i, uU-7.5 Hz). Mass spectroscopy (MHz-SI): t/ e. calculated for Sg2NhoMe: 405.2515, found 405.2509; 407 (4), 406 (27), 405 (100).

Example 18, spectral data: TI C V; 0.20 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 9.00 (PI, 5), 7.26 (1 H, indistinct), 6.96 (2H, 5), 6.86-6.76 (ZH, t ), 5.46 (2Н, 5), 3.76 (ЗН, 5), 2.85 (2Н, а, 9-7.7 Hu), 2.33 (ЗН, 5), 2.06 (6Н , 5), 1.28 (ZN, i, 9-7.7 Hz). Mass spectroscopy (MNZ-SI): m/e 389 (4), 388 (28), 387 (100). Analysis, calculation . for SgaNgaMaO: C, 74.58; H, 6.78; M, 14.50; found: C, 74.36; H, 6.73; M, 13.83.

Example 27, spectral data: TI C V; 0.20 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.96 (1H, 5), 6.95 (2H, 5), 4.25 (211.11, 9-7.5 Gu), 2.93 (2H, a , 9-7.7 Hu), 2.32 (ZH, 5), 2.04 (6H,5), 1.91-1.86 (2H,t), 1.50-1.38 (2H, t), 1.39 (ZN, Her. 9-7.7 Hz), 1.01 (ZN, i, 9-7.5 Hz). Mass spectroscopy (MHz-SI): t/e 325 (3 ), 324 (23), 323 (100).

Example 28, spectral data: TI C V; 0.28 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.96 (1H. 5), 6.95 (2H, 5), 4.24 (211, 6. 9-7.9 Hz), 2.93 (2H, a , 9-7.6 Hu), 2.32 (ZN, 5), 2.04 (6H, 5), 1.90 (211, t), 1.44-1.36 (711, t), 0.93 (ZN, i, 9-7, Gu). Mass spectroscopy (MNz-SI): t/e 339 (3), 338 (25), 337 (100). Analysis, calculated for

Sg21Ngvima: C, 74.96; N, 8.40; M, 16.56; found: C, 74.24; 11, 8, 22; M, 16.25.

Example 34, spectral data: mass spectrometry (EI): mp 365 (M-2), 363 (MaAN' 10095). Example 35, spectral data: TI C Ah 0.31 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.94 (1H, 5), 7.71 (111, a, 3-84 Hu), 7.58 (1H, a, 9-18 Hz), 7, 41 (1H, aa, 9u-8.4, 1.8 Gu), 4.27 (1H, Bi), 2.95 (2H, a, .1-7.3 Hz), 2.41 (2H, bi), 2.11-1.98 (2Н, BO), 1.42 (ЗН, и, 9-7.3 Gu), 1.37-1.20 (ЗН, т), 1.09-0 .99 (1Н, т), 0.84 (ЗН, и, 9-7.7 Hz), 0.82 (ЗН, и, уУ-7.7 Hz). Mass spectroscopy (МНз-СИ): т /e, calculated for C2OH2g5Ma4Si2: 391.456, found 391.1458, 394 (14), 393(71), 392(29), 391 (100).

Example 38, spectral data: Mass spectroscopy (MS-SI): m/e 375 (MAN' 10095). Example 40, spectral data: Mass spectroscopy (MS-SI): m/e 377 (MaAN', 10095). Example 48, spectral data: Mass spectroscopy (MHz-

SI): t/e 423 (MN, 10095). Example 50, spectral data: TI C V; 0.27 (30:70 ethyl acetate-hexane). "H NMR (300

MHz, SOSIv): 6 9.03 (1H, 5), 7.70 (1H, a, 9-8.0 Hz), 7.59 (1H, a, U-1.8 Hz), 7.41 (1H, aa, 2-8.0,1.8 Hz), 7.36-7.30 (2H, t), 7.24-7.19 (ZH, t), 5.50 (2H, 5 ), 2.87 (2Н, а, 9-7.5 Hz), 1.31 (ЗН, и, 9-7.5 Hz). Mass spectroscopy (MS-SI): t/e, calc. for SgonivMaSi: 382.0752; found 382.0746; 388 (3), 387 (12), 386 (16), 385 166), 384(26), 383 (100).

Example 51, spectral data: Mass spectroscopy (MS-SI): t/e 413 (MAN', 10095). Example 54, spectral data:

Mass spectroscopy (MS-SI): t/e 459 (MaN', 10095). Example 68, spectral data: TS Az 0.28 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.91 (1H, 5), 6.69 (2H, 5), 4.30-4.19 (1H, t), 3.82 (ZH, 5), 2 .92 (2H, a, 9-7.6 Hz), 2.41 (1H, Bo), 2.08 (ZH, 5), 2.07 (ZH, 5), 2.06 (1H, bi) , 1.38 (ZH, i, 9-7.6 Hz), 1.36-1.22 (4H, t), 1.10-0.98 (1H. t), 0.96-0.87 (1H, t), 0.84 (ZH, i, 9-7.0 Hz), 0.81 (ZH, i, 9-6.7 Hz). Mass spectroscopy (MHz-SI): t/e

383 (4), Z3X2 (27), 381 (100).

Example 122, spectral data: TI C V; 0.10 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.97 (111.5), 6.94 (211.8), 4.14 (2Н, а, 9-7.7 Hz), 3.48 (1Н ) . 366 (25), 365 (100).

Example 123, spectral data: TI C V; 0.24 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.97 (IN, 5), 6.94 (2H. c), 4.25 (211, 9-8, Hz), 3.48 (1H, a, 9- 7.I Hz), 2.63 (ZH, 5), 2.31 (ZH, 5), 2.01 (6H, 5), 1.81 (2H, t), 1.47-1.19 ( 8H, t), 0.91 (6H, t). Mass spectroscopy (MH3-SiI): t/e 381 (4), 380 (27), 379 (100). Analysis, calculated for SgaNzaMa: C, 76.15; H, 9.05; M, 14.80; found: C, 76.29; H, 9.09; M, 14.75.

Example 202, spectral data: TI S A; 0.20 (10:90 ethyl acetate-hexane). H NMR (300 MHz, SOCI3): b 8.82 (1H, 5), 6.96 (2H, 5), 4.46-4.38 (1H, t), 4.13 (ZH, 5), 2, 34 (ZH, 5), 2.28-2.11 (2H, t), 2.07 (6H, 5), 1.95-1.81 (2H, t), 1.38- 1.17 ( ЗН, t), 1.14-0.99 (1Н, t), 0.683 (ЗН, B 9-7.7 Hz), 0.80 (ЗН, И, 9-7.7 Hz). Mass-speciroskoyiya (Mnz-SI): t/e, calc. for Cg2HzoMmaO: 366.2420; found 366.2408; 369 (4), 368 (26), 367 (100).

Example 404, spectral data: TI C V; 0.20 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 6.93 (2H, 5), 4.20 (2H, 9-7.7 Hz), 2.90 (2H, a, 9-7.6 Hu), 2.83 (ZH, 5), 2.30 (ZH, 5), 2.03 (6H, 5), 1.88 (211, t), 1.42-1.34 (711, t), 0.93 (ZH , i, 9-6 Hz).

Example 414, spectral data: TI C V; 0.36 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.92 (IN, 5), 7.66 (IN, y, .1-8.1 Gu), 7.32-7.26 (2H, t), 4.54 (1H, t), 2.95 (2H, a, 9-74 Hu), 2.43 (ZH, 5), 2.39 (111, t), 2.03 (IN, t), 1.74 (ZN, a, 9-7.0 Gu), 1.41 (ZN, i, 9-7.5 Hz), 1.31 (1N. t), 1.16 (IN, t), 0.92 (ZH, i, 9-7.3 Hz). Mass spectroscopy (MHz-SI): t/e, calculated for St9NhaMaSi: 343.1690; found 343.1704; 346 (7), 345 ( 34), 344 (23), 343 (100).

Example 415, spectral data: TI C V; 0.25 (10:90 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.91 (I1H, c), 7.71 (NI, a, 9-8, Hz), 7.34-7.30 (2H, t), 4, 30-4.20 (1H, t), 2.94 (2H, a, 9-7.5 Hz), 2.50-2.35 (2H, t), 2.44 (311, c), 2 .08-1.95 (2H, t), 1.43 (ZH, i, 9-7.5 Hz), 1.29 (ZH, t), 1.08-0.98 (1H, t), 0.84 (ZH, 9-7.0 Hz), 0.81 (ZH, i, uU-7.3 Hz). Mass spectroscopy (MHz-SI): t/e 374 (7), 373 (33 ), 372 (25), 371 (100). Analysis, calculation for СгиН2?7СИМа:

C, 68.00; N, 7.35; M, 15.10; found: C, 68.25; H, 7.30, M, 14.85.

Example 424, spectral data: TI C V; 0.28 (5:95 ethyl acetate-dichloromethane). "H NMR (300 MHz, SOSIz): b 8.95 (1H, 5), 7.60 (1H, a, 9-7.7 Hu), 7.37 (1H, y, 9-0.8 Hu ), 7.21 (1H, ay, 9U-7.7, 0.8 Gu), 4.58-4.50 (1H, t), 2.96 (2H, da, 9-7.5, 2 ,0 Hz), 2.46-2.33 (1H, t), 2.40 (ЗН, 5), 2.08-1.96 (1Н, t), 1.74 (ЗН, а, 9- 6.6 Hz), 1.40 (ZN, 9-75 Gu), 1.39-1.22 (IN, t), 1.20-1.08 (IN, t), 0.92 (ZN, mass spectroscopy (MHz-SI): t/e, calculated for

SieNgaSiIMey: 343.1690; found 343.1697; 346 (8), 345 (38), 344 (25), 343 (100).

Example 434, spectral data: TI C V; 0.78 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.90 (IN, 5), 6.95 (2H, 5), 2.97 (2H, 9-7.3 Hz), 2.60-2.50 (1H, t), 2.41-2.33 (1H, t), 2.32 (ЗН, 5), 2.20-2.10 (1Н, t), 2.05 (ЗН, 5), 2.02 (ZH, 5), 1.85-1.80 (1H, t), 1.39 (ZH, i, 9U-7.5 Hz), 0.85 (ZH, i, 9-7, 5 Hz), 0.50-0.35 (2H, t), 0.25-0.15 (IN, t), 0.10-0.00 (1H, t). Mass spectroscopic (MHz-SI ): i.e., calculated for SgzNzoMy: 362.2470; found 362.2458; 365 (4), 364 (27), 363 (100).

Example 436, spectral data: TI C V; 0.31 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIizv): b 8.88 (IN, 5), 7.77 (1H, da, U-9.2 Hu), 6.87 (2H, t), 4.40-4 .25 (1H, t), 3.86 (ZH, 5), 2.99 (2H, a, 9-7.5 Hz), 2.60-2.35 (2H, t), 2.47 ( ZN, 5), 2.15-2.00 (1H, t), 1.80-1.70 (1H, t), 1.45 (ZN, i, 9-7.5 Gu), 0.84 (ЗН, и, 9-7.5 Hz), 0.50-0.35 (2Н, т), 0.30-0.20 (1Н, т), 0.10-0.00 (1Н, т ), -0.85 - -0.95 (1H, t).

Example 437, spectral data: TI C V; 0.25 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.90 (IN, 5), 7.73 (1H, a, U-9.2 Gu), 6.89-6.86 (2H, t), 4 ,58-4.51 (1Н, t), 3.86 (ЗН, 5), 2.95 (2Н, yes, 9-7.6, 1.8 Hz), 2.47 (ЗН, 5), 2.45-2.34 (1H, t), 2.07-1.97 (IN, t), 1.73 (ZN, y, 9-7.0 Gu), 1.42 (ZN, y, 9-76 Hz), 1.40-1.27 (1H, t), 1.20-1.07 (IN, t), 0.92 (ЗН, и 9U-7.4 Hz). Mass spectroscopy (МНз-СИ): t/e, calculated for СгоН27М4О: 3392185, found: 339.2187; 341(3), 340(22), 339 (100). Analysis, calculated for СгоНобиМаО: С, 70.98 ; H, 7.74; M, 16.55; found: C, 69.97; H, 7.48; M, 15.84.

Example 438, spectral data: TI C V; 0.42 (40:60 ethyl acetate-hexane). "H NMR (300 MHz, SOS): b 8.98 (IN, 5), 7.77 (1H, a, 9-91 Hz), 7.17 (2H, a, 9-8.8 Hz), 6.90-6.83 (4H, t), 5.42 (2H, 5), 3.86 (ZH, 5), 3.78 (ZH, 5), 2.86 (2H, a, 9- 7.5 Hz), 2.49 (ZN, 5), 1.33 (ZN, i, 9-7.5 Hz). Mass spectroscopy (MHz-SI): t/e 391(4), 390 ( 26), 389 (100).

Analysis, calculation. for SgzNgaMaOho: S, 71,11; H, 6.24; M, 14.42; found: C, 71.14; H, 5.97; M, 14.03.

Example 439, spectral data: TS B; 0.41 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.89 (IN, 5), 7.77 (IN, y, 9-31 Gu), 6.89 (2H, t), 3.86 (ZH, 5 ), 3.53 (1H, t), 2.91 (2H, a, 9-7.5 Hz), 2.49 (ЗН, 5), 2.28 (IN, t), 2.21 (1H , t), 1.43 (ZN, i, 9U-7.3 Hz), 0.86 (ZN, Her, 9U-7.3 Hz), 0.78 (2H, t), 0.46 (2 , t), 0.20 (1Н, t).

Example 440, spectral data: TI C V; 0.28 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIizv): b 8.89 (IN, 5), 7.73 (1H, a, U-9.1 Hu), 6.90-6.86 (2H, t), 4 ,60-4.40 (1H, t), 3.86 (ZH, 5), 2.95 (2H, yes, 9-7.7, 2.2 Hz), 247 (ZH, 5), 2, 44-2.36 (1H, t), 2.05-1.98 (IN, t), 1.74 (ZN, y, 9-7.0 Gu), 1.42 (ZN, i, 9- 7.5 Hz), 1.40-1.20 (B5H, t), 1.13-1.05 (1H, t), 0.830 (ZH, i 9-6.6 Hz).

Example 502, spectral data: TI C V; 0.63 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSs): b 8.92 (IN, 5), 6.95 (2H, 5), 4.60-4.47 (1H, t), 2.93 (2H, a, 9-7.7 Hz), 2.43-2.33 (1H, t), 2.32 (ЗН, 5), 2.16-2.06 (1Н, t), 2.05 (ЗН, 5 ), 2.03 (ZN, 5), 1.76 (ZN, y, 9U-7.0 Gu), 1.36 (ZN, Her, 9-7.7 163 Gu), 1.36-1, 20 (4Н, т), 0.86 (ЗН, и, 9-7.2 Г).

Mass spectroscopy (MH-SI): t/e, calc. For С22НзоМай: 350.2470, found: 350.2480; 353(3), 352(28), 351 (100).

Example 503, spectral data: 1 H NMR (300 MHz, SOSI»z): b 8.92 (1H, 5), 6.94 (2H, 5), 4.58-4.48 (1H, t), 2.93 (2H, a, uU-7.3 Gu), 2.32 (ZH, 5), 2.05 (ZH, 5), 2.02 (ZH, 5), 1.76 (ZH, a , 9-6.6 Hz), 1.36 (ZN, i, 9-7.3 Gu), 1.34-1.05 (VN, t), 0.88 (ZN, i, 9-7 Hz ). Mass spectroscopy (MH-SI): t/e, calcd. for С2зНз2Ма: 365.2705, found: 365.2685; 367(3), 366(27), 365 (100).

Example 506, spectral data: TI C V; 0.28 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOS): b 8.95 (IN, 5), 7.67 (1H, y, 9-84 Hu), 7.57 (1H, a, 9-1.8 Hu), 7.42-7.37 (1H, t), 4.56 (1H, sextet, 9U-7.1 Hu), 2.99 (2H, a, 97.5 Hu), 2.43-2.33 (1H, t), 2.09-1.97 (1H, t), 1.74 (ЗН, и, 9-7.0 Hz), 1.41 (ЗН, и 9-7.35 Hz), 1.35-1.07 (2H, t), 0.92 (ZH, y, 9-7.3 Hz). Mass spectroscopy (MHz-SI): t/e 367(12), 366(14) , 365 (67), 364 (24), 363 (100).

Example 507, spectral data: Mass spectroscopy (MS-SI): m/e 377 (M-AN' 100925).

Example 511, spectral data: TI C V; 0.51 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.97 (IN, 5), 7.87 (1Н, а, 9-81 Hu), 7.83 (1Н, а, 9-1.1 Hu), 7.68 (1H, aa, 9-81, 1.1 Hu), 3.60-3.51 (1H, t), 2.94 (2H, a, uU-7.5 Hu), 2.53 -2.39 (1H, t), 2.36-2.20 (1H, t), 1.96 (1H, Big), 1.42 (ЗН, и, 9-7.5 Hz), 0, 88 (ZH, i, 9-73 Hz), 0.88-0.78 (IN, t), 0.52-0.44 (2H, t), 0.24-0.16 (1H, t) Mass spectroscopy (MS-SI): t/e 412(7), 411(33), 410 (23), 409 (100).

Example 513, spectral data: TI C V; 0.62 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSs): b 8.97 (IN, 5), 7.87 (1H, a, 9U-8.0 Hu), 7.83 (1H, a, 9-0.7 Hu ), 7.68 (1H, aa, 9U-8.0, 0.7 Hz), 4.21 (1H, Bo), 2.96 (2H, a, 9-7.5

Hz), 2.42 (2H, Bi), 2.12-1.97 (2H, t), 1.43 (ZH, i, 9-7.5 Hz), 1.40-1.20 (4H , t), 0.85 (ZH, i, 9U-7.3 Hz), 0.83 (ZH, i, 9- 7.6 Hz). Mass spectroscopy (MS-SI): t/e 428 (8), 427(38), 426 (29), 425 (100).

Example 514, spectral data: TI C V; 0.51 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.96 (IN, 5), 7.86 (1Н, а, 9-81 Hu), 7.83 (1Н, а, 9-08 Hu), 7, 68 (1H, aa, 9U-8.1, 0.8 Hz), 4.20 (1H, Bo), 2.97 (2H, a, 9-7.7

Hz), 2.54-2.39 (2H, t), 2.15-2.01 (2H, t), 1.43 (ZH, i, 9-7.7 Hz), 0.84 (6H , and, 2-7.5 Hz). Mass spectroscopy (MS-SI): t/e 400 (7), 399(37), 398 (26), 397 (100).

Example 524, spectral data: TI C V; 0.50 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOS): b 8.89 (IN, 5), 7.76 (1H, a, 9Х-9.1 Hz), 6.90-6.87 (2H, t), 4 .35 (1Н, m Bi), 3.86 (ЗН, 5), 2.93 (2Н, а, 9-7.6 Hz), 2.48 (ЗН, 5), 2.39 (2Н, Big ), 2.00-1.90 (2H, t), 1.43 (ZH, i, 9-7.6 Hu), 1.38-1.22 (2H, t), 1.18-1, 02 (2H, t), 0.90 (6H, i, 9-7.3 Hz).

Mass spectroscopy (MH-SI): t/e, calcd. for Sgg2Nazi Mao: 367.2498, found: 367.2506; 369 (3), 368(25), 367 (100).

Example 526, spectral data: TI C V; 0.28 (10:90 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.91 (IN, 5), 7.69 (1H, a, U-8.1 Hz), 7.34-7.30 (2H, t), 4 ,40-4.35 (1H, t), 2.93 (2H, a, 9-7.4 Hu), 2.44 (ZH, 5), 2.38 (2H, t), 1.96 ( 2H, t), 1.43 (ЗН, и 9У-7.5 Hz), 1.35-1.22 (2H, t), 1.15-1.05 (2H, t), 0.90 ( 6H, her, 9-7.1 Hz). Mabs-spectroscopy (MNzg-SI): mp 374 (8), 373(35), 372 (25), 371 (100). Analysis, calculated for Cg1iH27MaSiI : C, 68.00; H, 7.35; M, 15.10; found: C, 67.89; H, 7.38; M, 14.94.

Example 528, spectral data: TI C V; 0.65 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.97 (IN, 5), 7.86 (1H, a, 9U-8.0 Hu), 7.82 (1H, a, 9-1.1 Hz ), 7.67 (1H, aa, U-8.0, 1.1 Hu), 4.38 (1H, Bo), 2.95 (2H, a, 9-7.5

Hz), 2.39 (2H, Bi), 2.04-1.92 (2H, BP), 1.42 (ZN, 9U-7.5 Hz), 1.40-1.21 (ZN, t ), 1.19-1.03 (1H, t), 0.91 (6H, i, 9--7.3

Hz). Mass spectroscopy (MS-SI): t/e 428 (8), 427(37), 426 (27), 425 (100).

Example 538, spectral data: TI C V; 0.56 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.96 (IN, 5), 7.88 (1H, a, 9U-8.0 Hu), 7.83 (1H, a, 9-08 Hu), 7.68 (1H, aa, 9U-8.0, 0.8 Hz), 3.77 (1H, Big), 2.95 (2H, a, 9-7.5

Hz), 2.61 (1H, Bi), 2.08 (1H, BO, 1.45 (ZH, i, 9-7.5 Hz), 1.36-1.25 (1H, t), 1 .17 (ZN, a, 9-6.6 Gu), 0.71 (ZN, 5 20-7.3

Hz), 0.69 (ZH, a, 9-7.0 Hz). Mass spectroscopy (MS-SI): t/e 414 (7), 413(33), 412 (24), 411 (100).

Example 534, spectral data: Mass spectroscopy (EB5I): mp 363 (M--2), 361 (M, 100925).

Example 544, spectral data: TS B; 0.63 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.90 (IN, 5), 7.74 (1H, a, U-9.1 Hz), 6.89-6.86 (2H, t), 3 .86 (ZH, 5), 3.79-3.73 (1H, t), 2.93 (ZH, yes, 9-7.7,2.6 Hz), 2.49 (ZH, 5), 2.03-1.99 (IN, t), 1.81 (ZN, y, 9-6.9 Gu), 1.41 (ZN, y, 9-7.3 Hz), 0.84-0 .74 (2H, t), 0.53-0.41 (2H, t), 0.28- 0.21 (1H, t).

Example 548, spectral data: TI C V; 0.42 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.99 (IN, 5), 7.84 (1H, a, 9-7.7 Hz), 7.82 (1H, a, 2-0.9 Hz ), 7.68 (1H, aa, 9-7.7, 0.9 Hz), 3.83-3.70 (1H, t), 3.00-2.90 (2H, t), 2, 09-1.98 (1H, t), 1.83 (ZN, a, 9U-7.0 Gu), 1.40 (ZN, U-7.3 Hz), 0.88-0.78 (1H , t), 0.57-0.41 (2H, t), 0.30-0.20 (IN, t). Mass spectroscopy (MHz-SI): t/e 398 (6), 397 (31 ), 396 (22), 395 (100).

Example 551, spectral data: TI C V; 0.56 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOS): b 8.93 (IN, 5), 6.94 (2H, 5), 4.75 (1H, heptet, 9U-7.0 Hz), 2.95 (2H , a, 9-7.7 Hu), 2.32 (ZH, 5), 2.04 (6H, 5), 1.80 (6H, a, U-7.0

Hz), 1.36 (ZH, i, 9-7.7 Hz). Mass spectroscopy (MS-SI): t/e 311 (4), 310 (34), 309 (100). Analysis, calculation. for

StenHama-0.5H2HO: C, 71.89; H, 7.94; M, 17.65; found: C, 71.59; H, 7.83; M, 17.41.

Example 558, spectral data: TS B; 0.53 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.98 (IN, 5), 7.86-7.81 (2H, t), 7.67 (IN, aa, U-8.4, 1.1 Hz), 4.60-4.48 (1H, t), 3.01-2.93 (2H, t), 2.49-2.35 (1H, t), 2.13-2.00 ( IN, t), 1.76 (ZN, a, 9-7.0 Hz), 1.41 (ZN, i 9U-7.5 Hz), 1.40-1.20 (4H, t), 0 .87 (ZH, i, 9-7.3 Hz). Mass spectroscopy (MHz-SI): t/e 414 (8), 413 (38), 412 (27), 411 (100). 165 Example 564 , spectral data: TI C B; 0.34 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOCI3): b 8.89 (IN, 5), 7.77 (IN, a, 2- 9.2 Hz), 6.89 (2H, t), 4.30-4.20 (1H, t), 3.86 (ZH, 5), 2.93 (2H, a, 9-7.5 Hz), 2.48 (ZH, 5), 2.45-2.35 (2H, t), 2.10-1.95 (2H, t), 1.44 (ZH, i, 9-7, 5 Hz), 1.40-1.20 (ZH, t), 1.10-0.95 (1H, t), 0.84 (ZH, i, 9-7.3

Hz), 0.81 (ZH, i, 9U-7.3 Hz).

Example 571, spectral data: TS B; 0.40 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.89 (IN, 5), 6.95 (2H, 5), 4.51 (1H, Big), 3.44-3.24 (4H, t) , 2.96 (2H, a, 9-7.3 Hz), 2.95-2.87 (1H, t), 2.85-2.75 (1H, t), 2.59-2.49 (1Н, т), 2.32 (ЗН, 5), 2.27-2.18 (1Н, т), 2.04 (ЗН, 5), 2.04 (ЗН, 5), 1.38 ( ZN, i, 9-7.7 Hz), 1.12 (ZN, and 90-70

Hz), 0.84 (ZN, B 9U-7.3 Hz). Mass spectroscopy (MNzg-SI): t/e, calc. for С2зНз2М4О: 380.2576, found: 380.2554; 383 (4), 382 (28), 381 (100).

Example 581, spectral data: TI C V; 0.33 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.89 (IN, 5), 6.95 (2H, 5), 4.49-4.39 (1H, t), 4.23-4.13 ( 1H, t), 3.91 (1H, ad, yU-9.9, 4.8 Hu), 3.48 (1H, ad, 9-91, 7.0 Hu), 3.30 (1H, da , 9-91, 7.0 Hu), 2.95 (2H, a, 9-7.7 Hu), 2.60-2.47 (1H, t), 2.32 (ZH, c), 2 ,15-2.01 (1H, t), 2.04 (ZH, 5), 2.03 (ZH, 5), 1.37 (ZH, i, 9U-7.5 Hz), 1.00 ( ЗН, и, 9-7.0 Hz), 0.86 (ЗН, и, 9-7.3 Hz). Mass spectroscopy (МНз-СИ): t/e, calculated for Сг2Нзи MO: 367.2498 , found: 367 2497; 369 (4), 368 (27), 367 (100).

Example 591, spectral data: TI C V; 0.42 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.91 (IN, 5), 6.95 (2H, 5), 3.76 (1H, Bi), 3.47-3.40 (1H, t) , 3.21 (ZN, 5), 2.99-2.90 (1H, t), 2.88 (2H, a, 9-7.3 Hu), 2.76 (IN, Bo, 2.51 -2.А1 (1Н, t), 2.32 (ЗН, в), 2.09 (1Н, Big), 2.08 (ЗН, 5), 2.04 (ЗН, 5), 1.95 ( ЗН, и, 9У-7.3 Hz), 0.56-0.44 (2Н, т), 0.30-0.21 (1Н, т). Mass spectroscopy (МНз-СИ): т/е , calculated for SgZiNziMaO: 379.2498, found: 379.2514; 381 (4), 380 (27), 379 (100).

Example 690, spectral data: TI C V; 0.12 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 9.01 (IN, 5), 7.38-7.22 (BN, t), 6.75 (1H, 5), 6.69 (1H, 5) , 5.48 (2Н, 5), 3.70 (ЗН, 5), 2.84 (2Н, а, 9-7.7 Hz), 2.37 (ЗН, 5),

2.05 (ZN, 5), 1.26 (ZN, i, 9-7.7 Hz). Mass spectroscopy (MS-SI): t/e 375 (4), 374 (28), 373 (100).

Example 692, spectral data: TI C V; 0.32 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.98 (IN, 5), 7.48 (1H, 5), 7.37-7.18 (BN, t), 7.11 (1H, 5) , 5.49 (2H, 5), 2.84 (2H, a, 9-7.3 Hz), 2.38 (ЗН, 5), 2.29 (БН, 5), 1.931 (ЗН, 9U-7.3 Hz). Mass spectroscopy (MHz-SI): t/e, calculated for SgzNhaMy: 356.2001, found: 356.1978; 359 (4), 358 (28), 357 (100) .

Example 693, spectral data: TI C V; 0.22 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.90 (IN, 5), 7.78 (1H, a, 9-9.5 Hz), 6.90-6.87 (2H, t), 3 .86 (ZN, 5), 3.62 (1H, B), 2.91 (2H, a, 9-7.5 Hu), 2.50 (ZN, 5), 2.40 (1H, Bo) . -1.25 (1H, t), 1.13-1.03 (1H, t), 0.95-0.75 (2H, t), 0.85 (ZH, i, 9-7, Hz) . (100).

Example 697, spectral data: TI C V; 0.28 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIizv): b 8.89 (IN, 5), 7.74 (IN, y, 9-95 Gu), 6.90-6.86 (2H, t), 4.58 -4.45 (1H, t), 2.95 (2H, yes, 9-7.7, 2.2 Hz), 2.48 (ZH, 5), 2.45- 2.35 (1H, t ), 2.09-1.99 (1H, t), 1.74 (ZH, y, 9-7.0 Gu), 1.42 (ZH, 97.5 Hz), 1.37-1.23 (ZH, t), 1.11-1.03 (1H, t), 0.86 (ZH, i, 9-7.0 Gu).

Example 724, spectral data: TI C V; 0.45 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.92 (I1H, v5), 7.75 (1H, a, y-8.4 Hu), 7.09 (1H, a, 9-26 Hz), 6.96 (1H, aa, 9U-8.4, 2.6 Gu), 3.87 (ZH, 5), 3.76 (1H, Bi), 2.94 (2H, a, 9U-7, 3 Hz), 2.61 (1H, Bi), 2.09 (1H, ro), 1.45 (ZH, i, 9-7.3 Hz), 1.36-1.26 (1H, t) , 1.15 (ZN, a, 9-6.6 Gu), 0.71 (ZN, i, 9-7.3 Hz), 0.68 (ZN, i, 9-6.6 Hz). -spectroscopy (MNzg-SI): t/e 377 (1), 376 (8), 375 (38), 374 (25), 373 (100).

Example 725, spectral data: TI C V; 0.31 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIizv): b 8.88 (IN, 5), 7.80 (IN, a, 2-9.2 Hu), 6.89 (2H, t), 3.86 (ZH , 5), 3.75 (1H, t), 2.92 (2H, a, 9-74 Hu), 2.60 (1H, t), 2.48 (ZH, 5), 2.05 (1H , t), 1.46 (ZN, i, U-7.4 Hz), 1.16 (ZN, a, 9-7.0 Hz), 0.70 (ZN, i, 9-73 Hz), 0.67 (ZN, a, 9U-6.6 Hz).

Example 727, spectral data: TI C V; 0.44 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.90 (IN, 5), 7.84 (IN, a, 9U-2.2 Hu), 7.74 (1H, a, 9-84 Hu), 7.65 (1H, aa, 9U-8.4, 2.2 Hz), 3.76 (1H, Bi), 2.93 (1H, a, 9-7.3

Hz), 2.60 (1H, Big), 2.08 (1H, BO, 1.42 (ZH, i, 9-7.3 Hz), 1.37-1.27 (1H, t), 1 ,16 (ZN, a, 9-7.0 Gu), 0.69 (ZN, i 2--7.3

Hz), 0.67 (ZH, a, 9-7.0 Hz). Mass spectroscopy (MS-SI): t/e 414 (7), 413 (33), 412 (27), 411 (100).

Example 750, spectral data: TI C V; 0.42 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.94 (IN, 5), 7.73 (1H, a, 0-84 Hz), 7.10 (1H, a, U-2.6 Hu), 6.96 (1H, aa, 9-8.4, 2.6 Hz), 3.87 (ZH, 5), 3.63 (1H, m Bg), 2.92 (hn, a, 9-7 ,3 Hz), 2.38 (1H, Bi), 2.22-2.10 (1H, t), 1.94 (1H, BI), 1.42 (ZH, i, 9-7.3 Hz ), 1.41-1.29 (1Н, ha), 1.23-1.08 (IN, t), 0.91 (ЗН, и, 9-7.3 Hz), 0.89-0, 79 (1H, t), 0.51-0.41 (2H, t), 025-0.15 (1H, t). Mass spectroscopy (MHz-SI): t/e 388 (8), 387 ( 34), 386 (25), 385 (100).

Example 751, spectral data: TI C V; 0.36 (40:60 ethyl acetate-hexane). "H NMR (300 MHz, SOSI»v): b 8.89 (IN, 5), 7.77 (IN, y, 9-91 Hu), 6.90 (2Н, t), 3.86 (ZN , 5), 3.62 (1Н, т), 2.84 (2Н, а, 9-7.5 Hz), 2.49 (ЗН, 5), 2.40 (IN, т), 2.19 (1H, t), 1.90 (1H, t), 1.43 (ZN, Her, 9-7.5 Gu), 1.38 (1H, t), 1.19 (IN, t), 0 .91 (ZH, i, U-7.3 Hz), 0.80 (1H, t), 0.49 (2H, t), 021 (1H, t).

Example 753, spectral data: TI C B: 0.44 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.92 (IN, 5), 7.84 (IN, a, 9-18 Hz), 7.73 (1H, a, 9-85 Hu), 7, 65 (1H, ad, 9U-8.5, 1.8 Hz), 3.65 (1H, Big), 2.92 (2H, a, 9-7.5

Hz), 2.38 (1H, Bi), 2.25-2.14 (1H, t), 1.94 (1H, Bi), 1.43-1.26 (1H, t), 1.40 (ZH, i, 9-7.5 Hz), 1.21-1.06 (1H, t), 0.92 (ZH, i, 9-7.3 Hz), 0.91-0.79 ( 1H, t), 0.52-0.44 (2H, t), 0.22-0.16 (IN, t). Mass spectroscopy (MS-SI): t/e 426 (9), 425 (42), 424 (31), 423 (100).

Example 767, spectral data: (MHz-SI): t/e 379 (M-AN' 10095). 167 Example 776, spectral data: TI C V; 0.41 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.93 (1H, 5), 7.73 (1H, a, 9-84 Hz), 7.09 (1H, a, y-2.6 Hu), 6.96 (1H, aa, 9U-8.4, 2.6 Gu), 4.28 (1H, ri), 3.87 (ZH, 5), 2.95 (2H, a, 9-7, 3 Hz), 2.41 (2H, Bi), 2.10-1.93 (2H, t), 1.43 (ZH, i, 9-7.3 Hz), 1.40-1.23 ( 1H, t), 1.18-1.03 (IN, t), 0.91 (ZH, i 9-7.3 Hz), 0.82 (ZH, 9-7.5 Gu).

Mabs-spectroscopy (MHz-SI): t/e, calc. for SgoNovSIMaO: 373.1795, found: 373.1815; 376 (8), 375 (35), 374 (24), 373 (100).

Example 777, spectral data: TI C V; 0.46 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSI"): b 8.89 (IN, 5), 7.76 (1H, a, 9-9.0 Hz), 6.90-6.87 (2H, t) , 4.29 (1H, Bo), 3.86 (ZN, 5), 2.94 (2H, a, 9-74 Hu), 2.48 (ZN, 5), 2.40 (2H, BO, 2.10-1.92 (2H, t), 1.44 (ZH, 90-74 Hz), 1.37-1.22 (1H, t), 1.18-1.02 (1H, t) , 0.90 (ZH, i, 9–7.3 Hz), 0.81 (ZH, i, 9–7.3 Hz). : 353.2341, found: 353.2328; 355 (3), 354 (23), 353 (100).

Example 778, spectral data: TI C V; 0.58 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.97 (IN, 5), 7.86 (IN, a, 9U-8.0 Hu), 7.83 (1H, a, 9-08 Hu), 7.68 (1H, aa, 9U-8.0, 0.8 Hz), 4.30 (1H, Big), 2.96 (2H, a, 9-7.5

Hz), 2.41 (2H, Bi), 2.11-1.95 (2H, t), 1.43 (ZH, i 9-7.5 Gu), 1.42-1.22 (2H, t), 0.92 (ZH, i, 9U-7.3 Hz), 0.83 (ZH, i, yU-7.3 Hz). Mass spectroscopy (MS-SI): t/e 414 (8), 413 (39), 412 (28), 411 (100).

Example 779, spectral data: TI C V; 0.44 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.91 (IN, 5), 7.84 (1H, a, 9U-I.8 Hu), 7.72 (1H, a, 9-8.0 Hu ), 7.65 (1H, aa, 9-8.0, 1.8 Hz), 4.31 (1H, ri), 2.94 (2H, a, 9-7.5

Hz), 2.40 (2H, Bi), 2.10-1.93 (2H, t), 1.40 (ZH, i, 9-7.5 Hz), 1.37-1.21 (1H , t), 1.19-1.02 (1Н, t), 0.91 (ЗН, и, 9-7.3

Hz), 0.81 (ZH, i, 9-7.3 Hz). Mass spectroscopy (MS-SI): t/e 414 (9), 413 (43), 412 (31), 411 (100).

Example 793, spectral data: Mass spectroscopy (MNzg-SI): t/e 367 (MAN, 10095). Example 799, spectral data: TI C V; 0.61 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.90 (1H, 5), 7.47 (1H, 5), 7.10 (1H, 5), 4.28 (1H, Bo), 2.93 (2H ) , 1.42 (ZH, i, 9-7.3 Hz), 1.35-1.21 (1H, t), 1.19-1.03 (IN, t), 0.90 (ZH, i 9U-7.2 Hz), 0.81 (ZN, i, 9-7.3 Hz). Mass spectroscopy (MHz-SI): t/e, calculated for Cg2HzoMa: 350.2470, found: 350, 2476, 353 (3), 352 (24), 351 (100).

Example 802, spectral data: TI S R; 0.38 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz: b 8.92 (1H, 5), 7.84 (1H, a, 9-18 Hu), 7.73 (IN, a, 9-84 Hu), 7.65 (1H, aa, 9U-8.4, 1.8 Hu), 3.53 (1H, Bo), 2.91 (1H, a, 9-74 Hu), 2.52-2.35 (1H, t), 2.34-2.20 (1Н, t), 1.95 (1Н, Bi), 1.40 (ЗН, и, 9-7.4 Hz), 0.89-0.79 (1Н , t), 0.87 (ЗН, и 9-7.3 Hz), 0.55-0.42 (2Н, т), 0.25-0.15 (1Н, t). -SI): t/e 412 (8), 411 (41), 410 (29), 409 (100).

Example 803, spectral data: TI C V; 0.33 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOS): b 8.93 (IN, 5), 7.85 (1H, a, 20-22 Hz), 7.71 (1H, a, U-8.4 Hu), 7.64 (1H, ad, 9-8.4, 2.2 Hz), 3.77 (1H, yes, U-9.9, 7.0 Gu), 2.93

(IN, yes, 9U-7.5, 2.0 Hz),), 2.09-1.98 (1H, t), 1.82 (ЗН, а, 9U-7.0 Hz), 168 1 .39 (ZH, i, 9-7.5 Hz), 0.86-0.78 (1H, t), 0.59-0.50 (1H, t), 0.49-0.40 (1H , t), 0.29-0.20 (1H, t). Mass spectroscopy (MS-SI): t/e 399 (2), 398 (8), 397 (39), 396 (24), 395 (100).

Example 804, spectral data: TI C V; 0.31 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.92 (IN, 5), 7.84 (1H, a, 9U-1.8 Hz), 7.71-7.62 (2H, t), 4 .55 (1H, t), 2.95 (2H, a, 9-7.5 Hz), 2.43-2.32 (1H, t), 2.10-1.98 (IN, t), 1.75 (ZN, a, 9-7.0 Gu), 1.39 (ZN, i, 9-7.5 Hz), 1.38-1.27 (1H, t), 1.19-1 .09 (1H, t), 0.93 (ZH, ii, 9-7, Hz).

Mabs spectroscopy (Mnz-SI): t/e 400 (7), 399 (32), 398 (22), 397 (100). Analysis, calculation. for Schi9NgoSiIRziMa: C, 57.51; H, 5.08; M, 14.12; found: C, 57.55; H, 5.06; M, 13.95.

Example 805, spectral data: TI C B; 0.41 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.92 (IN, 5), 7.84 (1H, a, 9-1, Hu), 7.70 (1H, a, u-8.0 Hu) , 7.64 (1H, ad, 9U-8.0, 1.8 Hu), 4.58-4.49 (1H, t), 2.95 (1H, a, 97.5 Hu), 2, 45-2.33 (1H, t), 2.11-2.00 (IN, t), 1.75 (ZN, a, 9-6.6 Hz), 1.39 (ZN, i, 9- 7.5 Hz), 1.38-1.21 (4H, t), 0.86 (ZH, i, 9-7.0 Hz). Mass spectroscopy (MHz-SI): t/e 414 (8 ), 413 (40), 412 (29), A11 (100).

Example 807, spectral data: TI C V; 0.49 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.91 (IN, 5), 7.84 (IN, a, 9-18 Hu), 7.73 (1H, a, 9-8.4 Hu), 7.65 (1H, ad, 9U-8.4, 1.8 Hu), 4.38-4.19 (1H, t), 2.94 (IN, a, 9U-7.5 Hu), 2 ,40 (2H, bi), 2.10-1.98 (2H, t), 1.41 (ЗН, 9-7.5 Hz), 1.38-1.20 (ЗН, t), 1, 09-0.99 (IN, t), 0.84 (ZN, i, 97.0 Hu), 0.81 (ZN, i, 2-7.5 Hz). Mass spectroscopy (MNz-SI): t/e 428 (7), 427 (32), 426(25), 425 (100).

Example 808, spectral data: TI C V; 0.51 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.91 (IN, 5), 7.84 (IN, a, 9-18 Hu), 7.72 (1H, a, 9-84 Hu), 7, 64 (1H, aa, 9U-8.4, 1.8 Hz), 4.37 (1H, Bi), 2.93 (1H, a, 9-7.5

Hz), 2.38 (2H, Bi), 2.02-1.90 (2H, t), 1.40 (ZH, i, 9-7.5 Gu), 1.38-1.20 (2H , t), 1.18-1.01 (2H, t), 0.90 (6H, i 9--7.3

Hz). Mass spectroscopy (MS-SI): t/e 428 (8), 427 (39), 426(30), 425 (100).

Example 809, spectral data: TI C V; 0.40 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.90 (IN, 5), 7.84 (IN, a, 9U-2.2 Hz), 7.72 (1H, a, 9-81 Hz), 7.65 (1H, aa, 9U-8,I, 2.2 Hz), 4.20 (1H, Big), 2.94 (1H, a, 9-7.5

Hz), 2.51-2.38 (2H, t), 2.13-2.00 (2H, t), 1.41 (ZH, its 9-7.5 Hz), 0.82 (6H, and, 9-7.3 Hz). Mass spectroscopy (MS-SI): t/e 400 (7), 399 (36), 398(25), 397 (100).

Example 824, spectral data: TI C V; 0.27 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.94 (IN, 5), 8.10 (1H, 5), 7.94 (1H, a, 2-8.8 Hz), 7.87 (1H , a, 9-81 Hz), 4.56 (1H, t), 2.96 (2H, a, 9-7.5 Hz), 2.40 (IN, t), 2.10-2.00 (1Н, т), 1.76 (ЗН, а, 9-7.0 Hz), 1.39 (ЗН, и, 927.5 Hz), 1.33-1.10 (2Н, т), 0 ,93 (ZN, i, 927.1 Gshch). ZE

NMR (300 MHz, SOSIv): b -58.2, -63.4. Mass spectroscopy (MS-SI): t/e 433 (3), 432 (24), 431 (100).

Example 832, spectral data: TI C V; 0.34 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOS"): b 8.94 (IN, 5), 7.73 (1H, a, 9U-8.5 Hz), 7.10 (1H, y, 9-2.6 Gu), 6.96 (1H, ai, 9-8.5, 2.6 Gu), 3.87 (ZH, 5), 3.55 (1H, Big), 2.92 (2H, a, 9 -7.3 Hz), 2.53-2.35 (1H, t), 2.31-2.18 (1H, t), 1.96 (IN, Bo), 1.42 (ZN, i 9 -7.3 Hz), 0.87 (ZH, i, 9-7.5 Gu), 0.87-0.79 (IN, t), 0.53-0.43 (2H, t), 0 ,25-0.15 (1H, t). Mass spectroscopy (MHz-SI): t/e 374 (8), 373 (34), 372 (24), 371 (100).

Example 833, spectral data: TI C V; 0.20 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.96 (IN, 5), 7.70 (1H, a, 9-84 Hz), 7.10 (1H, a, 9-2.5 Hz), 6.96 (1H, ad, 9U-8.4, 2.5 Hz), 4.16 (2H, a, 9-7.0 Gu), 3.87 (ZH, 5), 3.01 (2H , a, 9-7.3 Hz), 1.46 (ZN, Her, 9-7.3 Gu), 1.37-1.27 (1H, t), 0.66-0.52 (4H, Mass spectroscopy (MS-SI): mass 346 (6), 345 (32), 344 (23), 343 (100).

Example 834, spectral data: TI C V; 0.18 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOS"): b 8.94 (IN, 5), 7.69 (1H, a, 9U-8.4 Hz), 7.09 (1H, a, 9-1 Hu) , 6.96 (1H, aa, 9-84, 1 Hu), 4.60-4.50 (1H, t), 3.87 (ZH, 5), 2.97 (2H, a, 9-7 .3 Hz), 2.49-2.33 (1H, t), 2.09-1.97 (1H, t), 1.74 (ЗН, а, 9-7.0 Hz), 1.41 (ZN, i 9-7.5 Hu), 1.40-1.22 (1H, t), 1.21-1.09 (1H, t), 0.92 (ZN, i, 9-7, Hu).Mass spectroscopy (MS-SI): m/e, calcd for Sti9Hg2aSIMAO: 359.1639, found 359.1623; 362 (7), 361 (33), 360 (23), 359 (100). Analysis, calculated for C1i9HgzSIMaO-0.5HgO: c, 62.20; H, 6.32; M, 15.27; found: C, 62.33; H, 6.36; M, 14.86.

Example 835, spectral data: TI C V; 0.39 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.94 (IN, 5), 7.69 (1H, a, 9U-8.4 Hu), 7.09 (1H, y, U-2.5y) . (2H, t), 2.48-2.35 (1H, t), 2.11-1.99 (1H, t), 1.74 (ЗН, а, 2-6.9 Hz), 1, 41 (ZN, i, 9-7.5 Gu), 1.38-1.22 (ZN, t), 1.14-1.00 (1 H, t), 0.86 (ZN, i, 9 -7.1 Hz).Mass spectroscopy (MHz-SI): t/e 376 (7), 375 (33), 374 (23), 373 (100).

Example 836, spectral data: TI C V; 0.42 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSs): b 8.94 (IN, 5), 7.79 (1H, y, U-8.8 Hu), 7.09 (1H, y, 9-2.5 Hu ), 6.95 (1H, ay, 9-88, 2.5 Gu), 4.55-4.47 (1H, t), 3.87 (ZH, 5), 3.01-2.92 ( 2H, t), 2.48-2.35 (1H, t), 2.10-1.97 (1H, t), 1.74 (ЗН, а, 9-7.0 Hz), 1.41 (ZN, i, 9-7.5 Gu), 1.35-1.20 (B5H, t), 1.18-1.02 (IN, t), 0.84 (ZN, i 9-7, 0 Hu). Mass-spectroscopy (MHz-SI): t/e, calculated for С2гиНгеСИМа4О: 387.1952, found 387.1944; 391 (1), 390 (8), 389 (35), 388 (25) , 387 (100).

Example 837, spectral data: TI C B: 0.45 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.93 (IN, 5), 7.73 (1H, a, uU-8.8 Hz), 7.09 (1H, y, 9U-2.6 Hz ), 6.96 (1H, ay, 9-8.8, 2.6 Gu), 4.25 (1H, Bi), 3.87 (ZH, 5), 2.95 (gnH, a, 9- 7.3 Hz), 2.41 (2H, Bi), 2.10-2.00 (2H, t), 1.43 (ZH, i, 9-7.3 Hz), 1.37-1, 20 (ZH, t), 1.12-0.98 (1H, t), 0.84 (ZH, 9-7.3 Hz), 0.82 (ZH, i, 9-7.4 Hz). Mass spectroscopy (MS-SI): mp 390 (8), 389 (34), 388 (25), 387 (100).

Example 838, spectral data: TI C V; 0.48 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOS): b 8.94 (IN, 5), 7.72 (1H, a, 2-85 Hz), 7.09 (1H, a, U-2.2 Hu), 6.96 (1H, ad, -8.5, 2.2 Hz), 4.36 (1H, m ri), 3.87 (ZH, 5), 2.94 (gnH, a, 9-7, 3 Hz), 2.39 (2H, bi), 2.02-1.90 (2H, t), 1.42 (ZH, i, 9-7.3 Hz), 1.3539-1.21 ( 2H, t), 1.18-1.03 (2H, t), 0.90 (6H, i, 9-7.3 Hz). Mass spectroscopy (MHz-SI): t/e, calculated for SgiNgoSIMAO: 387,1952, found 387,1958; 391 (1), 390 (8), 389 (34), 388 (26), 387 (100).

Example 839, spectral data: TI C V; 0.36 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz"): b 8.92 (Ш, 5), 7.73 (1Н, а, 9-8.5 Hz), 7.09 (1Н, а, 9-26 Hz) , 6.96 (1H, aa, 9-8.8, 2.6 Hz), 4.19 (1H, run 5), 3.87 (ZH, 5), 2.96 (2H, a, 9- 7.5 Gu), 2.52-2.38 (2H, t), 2.13-1.99 (2H, t), 1.43 (ZN, Her, 9-7.5 Hz), 0, 83 (6Н, и, У-7.3 Hz). Mass spectroscopy (МНз-СИ): t/e, calculated for С.9НаСИМаО: 359.1639, found 359.1632; 362 (7), 361 ( 34), 360 (23), 359 (100).

Example 870, spectral data: Mass spectroscopy (MH3-SI): t/e 423 (M -- H', 100925).

Example 900, spectral data: TI C V; 0.38 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOS): b 8.93 (IN, 5), 7.75 (1H, a, 9-9.2 Hu), 6.90-6.86 (2H, t), 4 .23 (2H, 9-7.7 Hz), 3.86 (ZH, 5), 2.95 (2H, a, 9-7.7 Gu), 2.48 (ZH, 5), 1.93 -1.83 (2Н, т), 1.15 (ЗН, и, У-7.6 Hu), 1.43-1.36 (4Н, т), 0.92 (ЗН, и 9-7, 0 Hz).

Example 902, spectral data: TI C V; 0.28 (5:95 ethyl acetate-dichloromethane)."H NMR (300 MHz, COS13): b 8.94 (1H, 5), 7.63 (1H, a, 9-81 Hz), 7.37 ( 1H, 9, 9U-1.0 Hz), 7.21 (1H, aa, O-8, Y, 1.0 Hu), 4.38 (1H, bg), 2.94 (2H, a, 97 .5 Gu), 2.41 (ZN, 5), 2.40 (2H, ri), 2.00-1.90 (2H, t), 1.42 (ZN, i, 9-7.5 Hz ), 1.935-1.22 (2H, t), 1.17-1.03 (2H, t), 0.90 (6H, i, 9-7.3 Hz). Mass spectroscopy (MHz-SI) : t/e, calculated for SgiNgvSiIMaO: 371,2002, found 371,1993; 374 (8), 373 (34), 372 (25), 371 (100).

Example 944, spectral data: Mass spectroscopy (MH3-SI): mp 377 (M -- H', 100925).

Example 945, spectral data: Mass spectroscopy (MH3-SI): mp 365 (M -- H', 100925).

Example 947, spectral data: Mass spectroscopy (MH3-SI): mp 353 (M -- H', 100925).

Example 951, spectral data: Mass spectroscopy (MH3-SI): mp 381 (M -- H', 100925).

Example 952, spectral data: Mass spectroscopy (MH3-SI): mp 353 (M -- H', 10095).

Example 1003, spectral data: TI C V; 0.10 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.99 (IN, 5), 7.43 (1H, 5), 7.19 (2H, a, 9-88 Hu), 6.86 (2H, a , 9U-8.8 Hu), 6.84 (1Н, 5), 5.42 (2Н, 5), 3.94 (ЗН, 5), 3.91 (ЗН, 5), 3.78 (ЗН , 5), 2.86 (2Н, а, 9-7.7 Hz), 2.45 (ЗН, 5), 1.935 (ЗН, и, 9-7.7 Hz). ): m/e 421 (4), 420 (27), 419 (100). Analysis, calculation. For SgaNovMaOz: C, 68.88; H, 6.26; M, 13.39; found: C, 68 .53, H, 6.30, M, 12.96.

Example 1012, spectral data: Tpl-147-14820. TI S V; 0.18 (30:70 ethyl acetate-hexane). "H NMR (300 MHz,

SOS"): b 8.88 (1H, 5), 7.60 (1H, 5), 6.77 (1H, 5), 4.61 (2H, i, U-8.6 Gu), 3, 44 (1H, m ro), 3.24 (2H, i, 9-8.6 Hz), 2.94 (2H, BP), 2.44 (ZH, 5), 2.03 (2H, m Bi ), 1.45 (ZN, Bg, 9-6 Hz), 0.89-0.79 (2H, t), 0.58 (2H, Bi), 0.50-0.40 (2H, t ), 0.27-0.17 (2H, t). Mass spectroscopy (MS-SI): t/e 377 (4), 376 (27), 375 (100). Analysis, calculation. for SgzNovMaO: C, 73.77; N, 7.01; M, 14.96; found: C, 73.69; N, 7.08; M, 14.40.

Example 1023, spectral data: TI C V; 0.22 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 9.04 (IN, 5), 7.78 (1H, a, U-8.4 Hz), 7.44 (1H, a, 9-1.1 Hz ), 7.30 (1H, aa, 9-8.4, 1.1 Hz), 171 7.20 (2H, a, 9-85 Hz), 6.87 (2H, a, yu-8.5 Hz), 5.44 (2H, 5), 3.79 (ZH, 5), 2.90 (2H, a, 9-7.5 Hz), 1.32 (ZH, i, 9-7.5 Hz). Mass spectroscopy (MHz-

SI): t/e 467 (1), 466 (8), 465 (35), 464 (27), 463 (100).

Example 1027, spectral data: TI S VA; 0.41 (25:75 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.96 (IN, 5), 7.76 (1H, y, 9-8.4 Hu), 7.45-7.44 (1H, t), 7 .27 (1H, at, U-8 Gu), 4.61-4.51 (1H, t), 2.98 (2H, aa, 9U-7.5, 1.6

Hz), 2.48-2.35 (1H, t), 2.10-1.98 (1TN, t), 1.75 (ЗН, а, 9-7.0 Gu), 1.41 (ЗН , i, 9-7.5 Hu), 1.35-1.22 (2H, t), 0.93 (ZH, and y-7.2 Hz). Mass spectroscopy (MH-SI): t/e, calc. for Si9Na« SiEzMaO: 413.1349, found 413.1344; 416 (8), 415 (35), 414 (24), A13 (100).

Example 1028, spectral data: TI S VA; 0.45 (25:75 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.96 (IN, 5), 7.77 (1Н, а, 9-84 Hu), 7.44 (IN, t), 7.27 (1Н, at , 9-8 Hu), 4.57-4.49 (1H, t), 2.97 (2H, yes, 9U9-7.7, 1.7 Hu), 2.47-2.36 (1H, t), 2.12-2.02 (1H, t), 1.75 (ZN, 9, 9-7.0 Hz), 1.41 (ZN, her, 9-7.7 Gu), 1, 33-1.21 (4H, t), 0.86 (ZH, y, 9U-7.3 Hz). Mass spectroscopy (MH,-SI): t/e, calculated for SgoNgzSIezMa0: 427.1509, found 427,1507; 430 (8), 429 (35), 428 (25), 427 (100).

Example 1032, spectral data: TI C V; 0.44 (25:75 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.95(1

H, 5), 7.80 (1H, a, 9-8.4 Hz), 7.45-7.44 (1H, t), 7.30 (IN, at, 9-8 Gu), 4, 23-4.17 (1H, t), 2.97 (2H, a, 9-7.6 Hu), 2.54-2.39 (2H, t), 2.14-2.00 (2H, t), 1.43 (ЗН, и, 9-7.6 Hz), 0.84 (6Н, и, У-7.3 Hz). Mass spectroscopy (MH,-SI): t/e, calc. for C1i9Nai« SIEziMaO: 413.1368, found 413.1373; 416 (8), 415 (34), 414 (24), 413 (100).

Example 1150, spectral data: TI C V; 0.23 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz"): b 8.90 (IN, 5), 7.73 (1H, y, U-8.8 Hu), 7.36 (1H, a, 9-26 Hu) , 7.17 (1H, aa, 9-88, 2.6 Gu), 3.92 (ZH, 5), 3.70-3.55 (1H, t), 2.91 (2H, a, 9 -74 Hz), 2.45-2.35 (1H, t), 2.25-2.15 (1H, t), 2.00-1.90 (1H, t), 1.40 (ЗН, i, 9-7.4 Gu), 1.40-1.30 (1H, t), 1.20-1.10 (IN, t), 0.91 (ZN, i, 9-7.2 Hz ), 0.87-0.77 (1H, t), 0.54-0.44 (2H, t), 0.25-0.15 (IN, t). Mass spectroscopy (MHz-SI): t/e, calculated for Sg2NovEzM4O: 419.2057, found 419.2058; 421 (3), 420 (25), 419 (100).

Example 1153, spectral data: TI C V; 0.48 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 9.00 (IN, 5), 7.89 (IN, y, 9U-8.0 Hz), 7.84 (1H, 5), 7.69 (1H , a, 9U-8.0 Hz), 7.40-7.30 (5H, t), 5.14 (IN, y, 9-10.2 Gu), 2.82 (IN, aa, 915, 5, 7.7 Hz), 2.68 (1H, aa, 9-15.5, 7.7 Hz), 2.15 (1H, Bi), 1.23 (ZN, 9-7.7 Gu) , 1.13-1.03 (1H, t), 0.78-0.62 (2H, t), 0.53-0.43 (1H, t). Mass spectroscopy (MHz-SI): t /e, calcd for SgangiSieziMa: 457.1407, found 457.1389; 460 (9), 459 (35), 458 (29), 457 (100).

Example 1155, spectral data: TI C V; 0.46 (25:75 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz"): b 8.98 (IN, 5), 7.83 (IN, a, 9-84 Hz), 7.46-7.27 (7Н, т), 5, 13 (IN, a, U-10.7 Hz), 2.88-2.62 (2H, t), 2.15 (1H, BO), 1.26 (ZN, 97.5 Gu), 1, 12-1.02 (1H, t), 0.78-0.62 (2H, t), 0.54-0.44 (1H, t). Mass spectroscopy (MHz-SI): t/e, calculated for

SgaNai SI; ZMO: 473.1361, found 473.1365; 476 (9), 475 (36), 474 (29), 473 (100).

Example 1157, spectral data: TI C V; 0.19 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.93 (IN, 5), 7.77 (IN, a, 9-8.8 Hz), 7.40-7.30 (6Н, т), 7 ,19 (1H, aa, 9-8.8, 2.2 Hz), 5.13 (IN, y, 9U-10.6 Gu), 3.92 (ZH, 5), 2.79 (1H, ad, 9-15, 7.7 Hu), 2.64 (1H, da, 9-15, 7.7 Hu), 2.12 (1H, Bi), 1.21 (ZN, i 9-7, 7 Hz), 1.10-1.00 (1H, t), 0.77-0.62 (2H, t), 0.55-0.45 (1H, t). Mass spectroscopy (MHz-SI ): t/e, calculated for Sg5NovEEzMaO: 453.1902, found 453.1903; 455 (4), 454 (28), 453 (100).

Example 1158, spectral data: TI C V; 0.16 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIiz): b 8.98 (IN, 5), 7.46-7.25 (7H, t), 5.12 (1H, Bga, 9-9 Gu), 2.85 -2.62 (2Н, t), 2.14 (IN, BI), 2.13 (ЗН, а, 9-0.7 Hz), 1.18 (ЗН, da, 9-7,7.4 ,1 Hz), 0.75-0.35 (4H, t). Mass spectroscopy (MHz-SI): t/e, calculated for Cg4HgzSiOMa: 437.1300, found 437.1294; 440 (19), 439 (67), 438 (32), 437 (100).

Example 1161, spectral data: Mass spectroscopy (MH3-SI): t/e 441 (Ma-H', 10095).

Example 1163, spectral data: TI C V; 0.44 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 9.00 (IN, 5), 7.89 (1H, y, 9U-8.4 Gu), 7.84 (1H, 5), 7.69 (1H , a, 9U-8.4 Hu), 7.38 (2H, y, 9-9 Hu), 7.05 (2H, a, 9-9 Hu), 5.08 (IN, a, 9u-10 ,2 Hu), 2.82 (1H, aa, 9-15.5, 7.7 Hz), 2.68 (1H, ad, 9U-15.5, 7.7 Hu), 2.14 (IN , t), 1.25 (ZN, i, 9-7.7 Gu), 1.10-1.01 (IN, t), 0.74-0.62 (2H, t), 0.51- 0.41 (1H, t). Mass spectroscopy (MHz-SI): t/e, calculated for

SgaNgoSiRaMa: 475.1313, found 475.1307; 479 (1), 478 (9), 477 (35), 476 (30), 475 (100).

Example 1222, spectral data: Mass spectroscopy (MH3-SI): m/e 363 (M--H', 100905).

Example 1252, spectral data: TI S VA; 0.24 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.72

(IN, 5), 7.87 (1H, aa, 9-88, 5.5 Gu), 7.46 (1H, aa, 9-88, 2.5 Hz), 7.35-7.26 ( IN, t), 7.24-7.18 (BN, t), 7.08-7.01 (4Н, t), 4.89-4.79 (1Н, t), 4.49 (2Н, a, 90-121 Hu), 4.37 (2H, a, 9121 Hu), 4.27 (2H, her 20-93 Hz), 4.01 (2H, aa, 9U-9.9, 5.2 Gu), 2.98 (2Н, а, 9-7.7 Hz), 1.39 (ЗН, и, 9-7.7 Hz). Mass spectroscopy (MH-SI): t/e, calc. for

C2iNgoBaMaO»: 565.2227, found 565.2226; 567 (7), 566 (36), 565 (100).

Example 1255, spectral data: TI C V; 0.50 (25:75 ethyl acetate-hexane). "H NMR (300 MHz, SOSIiz): b 8.96 (IN, 5), 7.80 (1H, y, 9-84 Gu), 7.45-7.43 (1H, t), 7.31 -7.27 (1H, at, U-8 Hu), 3.80-3.73 (1H, t), 2.93 (2H, a, 9-7.3

Hz), 2.40 (IN, ro, 2.25-2.14 (IN, t), 1.95 (1Н, Bi), 1.42 (ЗН, и, 9-:7.5 Hz), 1.35-1.10 (2H, t), 0.92 (ZH, i, 9U-7.3 Gu), 0.91-0.80 (IN, t), 0.53-0.44 ( 2H, t), 0.24-0.14 (IN, t). Mass spectroscopy (MHz-SI): t/e, calculated for

SgiNgazS1 zma: 439.1519, found 439.1524; 442 (8), 441 (34), 440 (26), 439 (100).

Example 1256, spectral data: TI C V; 0.48 (25:75 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.95 (IN, 5), 7.79 (1H, y, uU-8.4 Gu), 7.45-7.43 (1H, t), 7 ,27 (IN, at, 9U-8 Hu), 4.35-4.25 (1H, t), 2.96 (2H, a, 9-74 Hu), 2.42 (2H, p), 2 ,12-1.93 (2H, t), 1.43 (ZN, i, 9-74 Hu), 1.37-1.22 173 (2H, t), 0.91 (ZN, i, 9 72 Gu), 0.83 (ZN, i,

Ch7.5 Hz). Mass spectroscopy (MH-SI): t/e, calc. for SgoNagzSIezMaO: 427.1514, found 427.1515; 430 (8), 429 (34), 428 (25), 427 (100).

Example 1295, spectral data: TI C V; 0.37 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.91 (IN, 5), 7.38 (1H, 5), 6.83 (1H, 5), 4.46 (IN, t, U-7, 3 Hu), 3.94 (ZN, 5), 3.91 (ZN, 5), 2.96 (2H, a, y-7.6 Hz), 2.49-2.39 (IN, t) , 2.43 (ZN, 5), 2.12-2.02 (IN, t), 1.75 (ZN, y, 9U-6.5 Hz), 1.44 (ZN, y, 9-7 .5 Hu), 0.86 (ZH, і, 927.5 Hz). Mass spectroscopy (MHz-SI): t/e, calculated. For СгоН27МаО»: 355.2134, found 355.2139; 357(3 ), 356 (23), 355 (100).

Example 1296, spectral data: TI C B, 0.37 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 9.00 (IN, 5), 7.68 (IN, 9, 9-84 Hz), 7.57 (1H, a, uU-2.2 Hz), 7.39 (1H, ay, U-8,4,2,2 Hu), 7.27 (2H, a, uU-8.4 Hz), 6.89 (2H, 9, 9U-8,4 Hu ), 5.56 (1H, aa, uU-9.7, 7.4 Hz), 3.79 (ZH, 5), 2.92-2.75 (ZH, t), 2.65-2, 55 (1H, t), 1.91 (ZH, i, 9-7.5 Hu), 0.92 (ZH, i, 9-6.6 Hz). Mass spectroscopy (MHz-SI): t/ is, calculated for SgzNgzSi2MaO: 441.1249, found 441.1247; 445 (12), 444 (18), 443 (67), 442 (30), 441 (100).

Example 1319, spectral data: Mass spectroscopy (MH3-SI): t/e 459 (Ma-H' 10090).

Example 1320, spectral data: "H NMR (300 MHz, SOCI3): b 8.99 (1H, 5), 7.68 (1H, y, uU-8.4 Hz), 7.58 (IN, a, 4-4.9 Gu), 7.42-7.30 (t, 6H), 6.04 (d, 1H), 2.82 (t, 2H), 2.16 (0, ЗН, .m7, 4 Hz), 1.27(3Н,0О-7,3,7, 714).

Example 1321 7906-5 spectral data: "H NMR (300 MHz, SOCI3): b 9.02 (1H, c), 7.98 (a, 1), 7.71 (ad, 1H), 7.57 (a, 1n), 7.42-7.26 (t, ЗН), 7.15 (t, 1Н), 5.38 (0, 1Н), 2.65 (t, 1Н), 2.4 ( t, 1H), 1.85 (t, 1H), 1.82 (5, ЗН), 0.97 (I ЗН), 0.8 (t, 2Н), 0.6 (t, 2Н).

Example 1322, spectral data: Mass spectroscopy (MH3-SI): t/e 437 (MAN' 100925).

Example 1323, spectral data: Mass spectroscopy (MH3-SI): mp 455 (M-A-H', 100925).

Example 1324, spectral data: Mass spectroscopy (ESI): t/e 425 (MAN), 381 (MAN'-SO", 100925).

Example 1325, spectral data:-Mass spectroscopy (MHz-SI): t/e 413 (MAN', 100925).

Example 1326 spectral data: Mass spectroscopy (MH3-SI): t/e 427 (MAN', 10095).

Example 1327, spectral data: Mass spectroscopy (MH3-SI): t/e 427 (M-AN', 100925).

Example 1328, spectral data: Mass spectroscopy (MH3-SI): t/e 427 (M-AN', 100925).

Example 1329, spectral data: Mass spectroscopy (MH3-SI): t/e 423 (M-AN', 100925).

Example 1330, spectral data: Mass spectroscopy (MH3-SI): t/e 418 (M-AN', 100925).

Example 1331, spectral data: Mass spectroscopy (MH3-SI): t/e 418 (M-AN', 100925).

Example 1332, spectral data: Mass spectroscopy (MH3-SI): t/e 499 (M-AN', 100925).

Example 1333 spectral data: Mass spectroscopy (MH3-SI): t/e 453 (MAN', 10095).

Example 1334, spectral data: Mass spectroscopy (MH3-SI): t/e 423 (M-AN', 100925).

Example 1335, spectral data: Mass spectroscopy (MH-SI): t/e 372 (MAN, 100925).

Example 1337, spectral data: Mass spectroscopy (MS-SI): t/e 443 (MaAN', 100925).

Example 1338, spectral data: Mass spectroscopy (MH3-SI): mp 427 (Ma-H', 10090).

Example 1339, spectral data: Mass spectroscopy (MH3-SI): mp 379 (Ma-H', 10090).

Example 1341, spectral data: Mass spectroscopy (MH3-SI): t/e 393 (Ma-H', 10090).

Example 1342, spectral data: Mass spectroscopy (MH3-SI): mp 378 (Ma-H', 10090).

Example 1343, spectral data: Mass spectroscopy (MH3-SI): mp 346 (Ma-H', 10090).

Example 1344, spectral data:. Mass spectroscopy (MS-SI): m/e 363 (MAN', 100965).

Example 1346, spectral data: Mass spectroscopy (MH3-SI): t/e 416 (Ma-H', 10090).

Example 1370, spectral data: TI C V; 0.23 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIiz): b 8.89 (IN, 5), 7.72 (1H, a, 0-84 Hz), 7.35 (1H, y, 92.5 Hz), 7, 17 (IN, ad, yu-8.4, 2.5 Hu), 4.27 (1H, Bi), 3.91 (ZH, 5), 2.93 (2H, a, 9-7.7 Hz ), 2.40 (2H, ri), 2.10-1.95 (2H, t), 1.41 (ZN, her, 9-:7.7 Gu), 1.59-1.27 (1H , t), 1.20-1.07 (1ТН, t), 0.91 (ЗН, 6 9-7.3 Hz), 0.81 (ЗН, и, У-7.5 Hz). spectroscopy (MHz-SI): t/e, calculated for SgiNovEzMaO: 407.2058, found 407.2052; 409 (3), 408 (24), 407 (100).

Example 1371, spectral data: Mass spectroscopy (ESI): mp 377 (M2), 375 (M' 10090). (B) O1-2-tetrazolyl (c) O2-1,2,4-triazol-2-yl

TABLE 1A div viv ri I dia.. 4 nos. ( led - and 1 "DID from IAE

Mshchi dyk M dae neo V finis s o VO NN o IF zh» zny zh ve I: ko vi ve p iv visa i1 VI? 11 in? gd) IV). heh)

She; pin iii in ND Pp mon nn gave niv gave kedy dv dan NN lini vapinttnn

M di x v vd! in: di vk ve vi? Tpl.,

PRI p pe p. naltnsttichtttannttnishtn internet Anna, 1943 sn, sn, n SY, sn, sn, nn SY; SN oil

Key: What (a) For the compounds marked "oil", the data are given below: 175 Example 1043, spectral data: TI C B; 0.40 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, COsSiv): a 8.91 (1H, 5), 7.43 (1H, 5), 7.10 (1H, c), 4.60-4.50 (1H, t) , 2.94 (2H, ad, 9-7.5, 2.0 Hz), 2.45-2.35 (1H, t), 2.35 (ZH, 5), 2.28 (BN, 5 ), 2.07-1.97 (1H, t), 1.73 (ZH, y, 9-6.9 Hz), 1.41 (ZH, 6 9-7.5 Hz), 1.40- 1.27 (1H, t), 1.20-1.07 (IN, t), 0.92 (ZH, i, 9-7.3 Hz). Mass spectroscopy (MHz-SI): t/e , calculated for SgiNooMy: 337.2392, found 3372396; 339 (3), 338 (23), 337 (100). Analysis, calculated for SgiNoviMy: C, 74.96; H, 8.40; M, 16 , 65; found: C, 74.28; H, 8.02; M, 16.37.

TABLE IV i div viv 1a iv 1a

К - К К -, E) with Кк - и и uch m: и Mal Mav M zy В vi -х- | yin ni-- x- | ; d2-- x- | iya «y t v t vi? Did you come with me? (c) (B) (E

M vi H t eV NA dy mi "PEV um ppnanlttasha'rnnnnnntk plyni dn lm dnyni nm chyuchni DOIP NLLennnch 1270 sun, Sun, SE, o sne 17 ss Ne s-saN, - on 1271 sun, se, SE, sun,o ,- s-s,, ss, -

Sai, 1272 st., St. SE, OSNITO-00oe-si. e-s, -

MISYA, i 1273 sm, sm, St, pines; 00e-bn o e-sv, -

Mmmmm! 1 1274 SN, SN, SE. ossnuyn- s-0 sn, t- (OVIS.,N, 1275 «s. sp, osi, SN, sn, san, 7-19 1276 sn, sn on sk, sv. s.n, - 1377 sn, sv , sun, sun, sun, sun, A 1278 st NE, fall sun, sun, sun, - 1279 sun hundred O(st- sun sun, sleep - on 1280 SN, sun, asngo; - sun, sun, San. - sov, 1281 СН сн осн о- СН, СВ, сн, -

MISNI, 12 82 Si se, OiSN.1:- sn, sv, sn. -

NyvySs17

TABLE 1C

1" century

Kk

SN -kh- h Ka vi

Ki! to tn

Mpricl. хХ g y v i: v "s 1501 sn, s1 SE, n s, osn, 75-78 1502 SN, si SE, kn SN, sny, oil 1503 SNI s1 si in s.n, s,shOosn, - 150 sy, ri osv, i s;y, senses, - 1505 sn SE, OsN, N son, sg.SHCOosN, - 1508 sy, si vOo,sN, N son, s.naOsy, - 1507 SN, si pines , n SON, S, SNa -

IOV sia, sn, Osn, SNI San, s,niasn, - 1509 i, si sv, E sa, s.nesn, - 1510 sn, sn osn, E sn, s, Inoosn, - 1 sni svi Se, St, sia, s.asn, - 1312 sn. sgi1 SE. i s--B, s.nAosn, - 1513 СН, с1 с1 Н -С,Н. cSaNAOSNU - 1514 sn, si osn, n 2e-s,N; s,nuOosn, - 1515 se, SE, osv, n ss, szNOSN, - 1316 СН» si BO,N, Н с-сН, sanosН, -

I317 CH; si sosyu, N s-s. sok, 4 1518 sn, sy, osn, SNI 2s-s,H, S.NiOsNa - 1519 sy, si sy, E s-s,H, S.N,OSK, -

1520 dream sne osn, Ek s-SN s.nIosu, - woo! dream St., Sun., Sleep 8-3, SUS, - 1522 St. Si. Sat. St.

Inc. sn..- SI s1 V sov, SNISN - 1524 sya, her OSNI n SN, snOosSy, - 1525 sy, sk, osv N San snaosn, - 156 sn, si 505СВ N San; СсОосСву -

KB si; s1 sosya, n sv snyusn, - 15728 sn, sy, sn, sn, SON, snose, - 529 sya, si sn, ssan, snsn, - 1530 sy, sya, osn, ,E so sn.osu, - 1531 si, sn, sn, sn, sn, sys, - 1532 sn. si CE, n s-sV, sn,osn, . 1533 se; si si N «-С4Н sn,osn, - 1514 sya, si Osn, N s-SW snpyusn, - 1535 sn, SE, osy, Н s-sN, sn,osn, - 1516 sn, s1 osn, KN s- sU sN.oSN, - 1537 sk; si сОоск, н с-С;Н, сНёos, - 1535 sk, SE, OSY sna с-сН, СНьОСсН - 1539 сн, си сн, Е вс, stosu - 150 sya; sk, Osn, E ssuV, SIS, - 1541 sya, sn, sv, sya, son, sndsn, - 1542 o si SE, n sna s,n,Osn, oil 1343 a si s1 n sn sSanOs, - 1544 o si wasp, n Sam. SN, OSYA, - 1545 o SE, osn, n San, s.nOse, . 1542 o vu BOSNa Io son, ss, - 1547 o si sosk, N son, s.vosn, - 1548 o sn; osn, sk, sanu SNO SY, - 1549 o si snu Z Sun s.vosn, - 15590 (t) sn, OSY, E San, s.N.OsSYA, - 1531 o sy, sn. sya, sani enosn, and 1552 a si SE, n s-SN, s. VOSY, - 1553. b sI1 s1 n s-Ssl s,, osi, - 1554 o si osi, n "2-SV, s Ose, - 1555 o sya, se, n se-sy, SiIN, OSN, - 15548 ge! si an, B s-sy, sen, osn, -

1557 o si SOS K s-s.n, s,naosn, - 1558 i! sn, osn, sv, s-suN, sSzvaosnu - 1559 o si sn, E s2-sSYx s.,n,osn, - 0. sn, osn, E s-SUN, Sas» - 1551 o sn sn, SN, e-Sy, s.nyosn, - 1552 o si se, n sen. stos, oil 1563 o si ost, Kn sin, snizsn, - 1564 o Se, osn, n s,v, sny sn, - 1365 o vi BOJYA, V Sv sny, - 1566 ob si sSsosn, Nn S.n, sNse , - 157 o st osn, sn, SN» sn.osn, - 6 o si sk, E san, snosya, - 1569 o sn, osni; E san, SNUsNu - 1570 o sia, sn. everything en snosn, - 1571 o si SE, E s-s,N, snsn, . 1571 o Ki si n 2-suH, sn,osYa, - 1573 o si osi, n s-SzH, sn.osi, - 1574 o se, osn, n s-SaNe stasn - 14750 s1 50,СН, in s- 08 sNaOsNi - 1516 o si sosi, n s-s,n, sn,osv, - 1577 o sn, osn, sn, s-s,n stOsy, - 1578 (is) s SN, KE VISIN, sny, - 1579 o sn, Osn, Gi s-s, stIsV, - 1580 o sn, sy, sy, s-s.V, sn.osn, - tTAvI,n 10 ve ih. sleep hu with

Most of you

Mpricl. U gu e vi i" de To nab sy, sn, si K Sai, "-soN, 109-131 182 sy, 1 si n son, Sen osi, - 1603 sn, si osn, n SaNya SaN,OsN, - 164 sn. Sg, Os, n sn, s., vasn. - 1605 sy, si Bon. n Sian, stos, - 1506 sn, hundred pines, I owl, szn, Osn, - I am looking for sn, sn. Osn, sn, Sen, Seny sYa, - 1608 sun si son, Z sun, sZNaOsN, - 1609 sun. sv, sun, E san, s,schosN, . 1510 SN. sv, sn, sia, san, sS.nosn, - 11 sleep a se, I so sune sosny, - 42 che: "1 si H s-SN, stosu, - 1513 sn; si osn, in osn, s.n.chosn, -

Iv14 se, SE axes, n s-sYa, s.nosn, - 1615 sun, s BOSN, N s-s. saNn.OsN, - 1516 sn, si sose, and 2-2, sS.n.osn, - ib7 sv, se, osn, sv, ss, saneost, - 1613 sy; si sia, Eh s-S sanoosi, -

Ev19 СН, сн, осн, h с-СуНв са.носН, - 160 св сн, сн, сн, с-С,Н, с,н, осн, - 1621 сн, сх SE, Н сн, снюсн, kaspo k822 Se, Dee Bee and Sun; snsn, - 163 SN, si osn n St, SOS, - 1624 sy, SE, osn, NN syn, stosy, - 1625 Sn, si Zbs, (n sn, sOosya, - 1526 sv, s1 pines, Kn san, sEsn , - 1527 se, sun, sun, SY. Sun sun, Oosn, - 1625 sun, si sun. Her NE, svosn, - 1522 sy, NE, axis, E sun, pine - 1610 sun, SN, NE sv , SN, stos, - 181, sn, si SE; In s-suV, sN, osi, - 1631 sn, si s1 K -S,y, SNoOSYAH - 631 sv, si she, I se-sy, snosn, - 1514 Sn, Se. Osn Kk s-s snsYa, -

1635 si "ki 8bosn, KN s-s.N, svOosk, - 1636 SYA" si sosn. n s-Szb Kai -. 1837 St. sv o sv s-s.V, snsn, - 1638 sni s1 sn, E se-s.N, snyusn, - 1639 sn, sn, axis, E s-S.N, sys, - 1640 sn, SN, sya, SN, s-s.n svsia, - 164 a si SE, n s.n, S. osn, aslo ni s si s n sen, s,nOsN, - 1643 o skh osn, N san, s.naosi , A 16 a SE, osk, ni siy, sn. OSNI - 1645 o s BOzSN. n si sishchosy, - 1646 s si sosn, n san, sUn,osn. - 1647 и сн, осн, сн, San, С.О сн, - 1648 o si se, E sov, s.nHosy, - 1545 0 сн, оС, E Son. s,n,sn, - 1650 o'clock sy, sya, san, sv,osn, - 1851 o SI SE, N s-s.N,. sen,osn, - 1652 a si si n s-zN, sUn,osYa, - 1554 o EV: osn, K sh-SN sosni - z655 She BOS nn tyni Z EN fri 1556 in si sesn, n s-siY, sh -shshchosy, - 1557 ЕВ) сн, ОСЙ, sy, ена сОосв, - иБ3й ия; г1 сн, Е с-сН, сСИн,осн, - (58 o SN Osy, E i) in, suvosn, - 1560 (c) сн, си, СН, s tok, sashOosya, - 1661 o si se, p) San, SsNIOSYA, oil 1552 i) si osn, y sin, stos, - 1683 o SE, osi, n Sen, SIS, - 1554 o si BOSN.

N san, snOsn, - 1555 o si pine, N SN, SsNsy, - 15665 0 I osn, SN, soy, snosn, - 1687 ke si sy; E sin, stok, - on BA sia, os, E s.n, SsNSE, - 1659 and SV sn, SY, son, SOS, - go o s1 SE, in! s-s sNyusia, -

157 o sa si n sem stos, -

I672 o si ren, n sssin, SNOSYA, - 1673 o se, Osn, N ss, svIOSNa - 1674 se s 5OSNu i) ss, sNoSN, - 1675 Mo) si Osy, y ss sNIyuSsn, - - sho Sl SN Snu 0 ss SOS ul 1677 o s1 sun, E SIY, s YAOSNI - 16 o NE, osn, E s-suN, eNOSV, - ie o sn, sya sn, s-sv, snosn, -

The following methods of preparation of 1-benzyl-b-methyl-4-(2,4,6-trimethylphenyl)imidazo (|4,5-c|Ipyridine (Example 2001, Table 2, Structure A) can be applied to obtain all compounds examples

Structures of A in Table 2 with minor procedural modifications where necessary and using reagents of acceptable structure.

The methods shown in Schemes 13 and 14 can be used to prepare many of the example compounds of Structures B and C in Table 2 with minor procedural modifications where necessary and using reagents of acceptable structure.

Example 2001

Preparation of 1-benzyl-b-methyl-4-(2,4,6-trimethylphenyl)imidazo (4,5-c|Ipyridine

Part A. A solution of 4-chloro-b-methc3-nitroshridone (5.0 g, 26.5 mmol) in acetonitrile (9 mL) was treated with benzylamine (2.89 mL, 26.5 mmol) and diisoprophrethylamine (5.54 mL, 31.8 mmol). This mixture was heated with an inverted refrigerator for 4 hours, then cooled to room temperature and stirred for 12 hours. This mixture was partitioned between dichloromethane and water (200 ml of each reagent), and the aqueous layer was extracted with dichloromethane (200 ml). The extracts were washed successively with water (200 ml) and combined, and the resulting precipitate was collected by filtration. The filtrate was dried over sodium sulfate, re-filtered and evaporated to give the secondary crystalline product, 4-benzylamino-b-metshi-3-nitroshridone (total 6.74g, 26.0 mmol, 9895). Tpl-.-246-247"0. TI C Ah 0.35 (10:90 isopropanol-ethnoacetate). "H NMR (300 MHz, SOCI3): a 10.48 (1H, Bug 5), 9.69 ( 1H, Bi 5), 7.41-7.26 (BN, t), 5.66 (IN, 5), 4.57 (2H, a, 9U-5.5 Hz), 2.26 (ZH, 5). Mass spectroscopy (MS-SI): t/e 261 (10), 260 (70), 226 (100).

Part B. A solution of pyridone from Part A (6.72 g, 25.9 mmol) in phosphorus oxychloride (52 mL, 25.5 mmol) was stirred at room temperature for 3 days. The reaction mixture was poured into a mixture of ice (150 g) and dichloromethane (200 ml). After melting the ice, another 100 ml of dichloromethane was added, and with the help of solid MansSoz, the pH of this mixture was set to 7. This mixture was separated, and the aqueous phase was extracted with dichloromethane. The extracts were combined, dried over sodium sulfate, filtered, and evaporated to give the product, (4-benzylamino-2-chloro-b6-methyl-3-nitropyridine), as a bright yellow solid (6.45 g, 23.2 mmol, 9095). TI C B: 0.76 (ethyl acetate). "H NMR (300 MHz, SOSIv): a 7.43-7.26 (5H, t), 7.04 (1H, BP), 6.47 (1H, 5), 4.48 (2H, y, 9-5.5 Hu), 2.40 (ZN, 5). Mass spectroscopy (MHz-SI): t/e 281 (5), 280 (35), 279 (17), 278 (100).

Part C. A solution of the nitro compound from Part B, above, (6.42g, 23.1 mmol) in methanol was treated with iron powder (13.61g) and glacial acetic acid (13.bml). The resulting mixture was heated under reflux for 2 h, then cooled, filtered through celite (washed with methanol) and evaporated. The residual material was dissolved in dichloromethane (231 ml) and 1 M aqueous HCl (162 ml), and with the help of solid ManHCO3, the neutral pH value was set. The mixture was filtered through celite and separated, and the aqueous phase was extracted with dichloromethane. The extracts were combined, dried over sodium sulfate, filtered and evaporated to give the product, 3-amino-4-benzylamino-2-chloro-o-methylpyridinium as a solid (5.59g, 22.6 mmol, 9895). Tal-177-17820. TI S V; 0.60 (ethyl acetate). "H NMR (300

MHz, SOSI»v): a 7.41-7.32 (5H, t), 6.933 (1H, 5), 4.54 (1H, Bi), 4.36 (2H, y, 3-51 Gu) , 3.30 (2H, g 5), 2.35 (ZH, 5).

Mabs spectroscopy (Mnz-SI): t/e 251 (6), 250 (37), 249 (19), 248 (100).

Part 0. A suspension of the diamine from Part C, above, (2.15 g, 8.68 mmol) in triethyl orthopropionate (5 mL) was treated with concentrated NOS (3 drops) and heated with a reflux condenser for 1 hour, then cooled, and the excess orthoether was extracted by vacuum distillation. The residue after distillation was dissolved in ethyl acetate (120 ml) and washed with water and brine (100 ml each). The aqueous phases were successively back-extracted with ethyl acetate, and the extracts were combined, dried over sodium sulfate, filtered, and evaporated to give M-(4-benzylamino-2-chloro-b-methylifidin-3-yl)/propionamide O-ethyl imidate (2, 62g, 91965). THOSE. C Vk 0.40 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): a 7.39-7.29 (5H, t), 6.29 (IN, 5), 4.64 (IN, Org, 9U-5.8 Hz), 4 .37 (2H, a, 9-58 Hz), 4.25 (2H, Bi), 2.35 (ZH, 5), 2.18-2.11 (2H, ha), 1.36 (ZH, i, 97.0 Hu), 1.06 (ZN, i, 9-7.7 Hz). Mass spectroscopy (MHz-SI): t/e 335 (7), 334 (34), 333 (22) , 332 (100).

Part E. A solution of the compound from Part O (2.62 g, 7.90 mmol) in phenyl ether (10 mL) was heated to 1707 for b hours, then cooled and poured into ethyl acetate (150 mL). Then it was washed with water and brine (100 ml each), dried over sodium sulfate, filtered and evaporated. The residual liquid was separated by column chromatography (hexane, then ethyl acetate) to give the product, 1-benzyl-4-chloro-2-ethyl-b-methylimidazo(4,5-pyridine, in the form of oil (2.16 g, 9695). Tal -.140-14170. TI C Ak 0.06 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): a 7.36-7.32 (ZH, t), 7.02-6 .98 (2H, t), 6.93 (1H, 5), 5.31 (2H, 5), 2.89 (2H, a, 9-7.3 Hz), 2.58 (ЗН, 5) , 1.39 (ZH, i, 9-7.3 Hz). Mass spectroscopy (MHz-SI): t/e 289 (6), 288

(35), 287 (20), 286 (100).

Part R. A solution of zinc chloride (538 mg) in tetrahydrofuran (u/ml) was treated with a tetrahydrofuran solution of 2-mesitylmagnesium bromide (3.95 ml, 1.0 M) and stirred for 1 hour. In another flask, a solution of bis(striphenylphosphine)palladium chloride (9 µg, 0.132 mmol) in tetrahydrofuran (Xml) was treated with a solution of diisobutylaluminum hydride (0.26 µg, 1.0 M) in hexane, and this solution was stirred for 20 minutes. The arylzinc solution was then cannulated into a flask containing the palladium catalyst, followed by the addition of the chloride obtained in Part E. The mixture was heated with a reflux condenser for 12 h, then cooled and poured into water (100 mL). It was then extracted with ethyl acetate (2x150ml), and the extracts were washed with brine, combined, dried over sodium sulfate, filtered and evaporated. The residual material was separated by column chromatography (1:11 ethyl acetate-hexane) to give the title product as a solid, which was recrystallized from ether for purification (187 mg, 29965). Tpl-:177-1802C (ether). TI C Vk 0.27 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): I 7.38-7.32 (ZH, t), 7.10-7.05 (2H, t), 6.96 (1H, 5), 6.93 ( 2Н, 5), 5.32 (2Н, 5), 2.84 (2Н, а, 9-7.3 Hz), 2.64 (ЗН, 5), 2.30 (ЗН, 5), 2, 02 (6Н, 5), 1.26 (ЗН, и, 9-7.3 Hz). Mass spectroscopy (МНз-СИ): t/e 372 (4), 371 (29), 370 (100). Analysis, calculated for C25H27Ma: C, 81.26; H, 7.38; M, 11.37; found: C, 80.70; H, 7.26; M, 11.20.

TABLE 2 IDs 1K in external sleep -x- | ro sni-x- KD siz-x-5u. || y "Mk y 1 "M" 5 l x "M 5 i 1

Vb vi ke di kb ti ti actions vii

In short circuit (A) (c) (S

My application /-XI: Vo v d «le 2001 p. S,Nu masdo 2095 se, si si n n s-S,H 128-130 2005 sn, si si i n e-S,n,. - soybeans, si sk1 N H 2-сСИ,-se-с5Н, oil 2007 sn, s si n B zone o-сН, - 2006 sn, s1 si N НЙ o 2-ОСН,-с-с,Н, - 2009 sia, si styn n 2,5-ISNYz-2-sV. - 2015 st, si si n N z-(sv1sn-5-sn- ss, - 2911 s, si si In n n 9- fluorenyl oil 2017 sv, si si n H 1- tetrahydronaphthyl oil 2013 sia, bo s1 n n 1 -indanil oil 2814 st. si "1 N V- yachroman oil 2015 st. Ck n 5 dibenzosoverenil - 2938 sya, si st, n n e-s.n - 2919 sn, si sp, n n ss, 145-147 2020 sia, si sv, In Kk e-sa masla 2921 sp. si o sk , V n s-Sa 125-135 2022 sv, 91 se, v n 2-si,, - 2023 sia, 910 sk, n 2-SN,-s-S,V z8-39

2024 dream si sv N n 3-sNna sn, | - 2025 sm. si sv, N E 2-OsSNu-s-sUN, - 2025 s si st, n E 2.5- (SNI se SuV - 2027 sy, si st, n Ya z- (sk. sn-5-SN.-e- s, - 928 sk, si st, Н H 8- fluorenyl - 2029 sk: si sv, Н n 1- tetrahydronaphthyl 2030 sn, si SE.

GT I. 1-indanil 2031 sy, c1 sec, n Kk 4- chromanil 2012 se, c1 se, n n 2-okooes-c,H, - 2933 SY. c1 SE PI H 5-dibenzosuberyl - 2034 dreams. с1 св, Н 5-dibenzosuberenyl - 2935 sn. s1 osv, in k e-s, H 2 2oza sn. si Osn, Kk N s-s.Nn, - 2037 sk, s1 axis, Kk n sen - 2038 se, si axis, NN N e-S,Ni - 2919 sya, s1 osn, Kk n ss, . 2640 sn, si axis, Kk n zesn,-e-S, - 2041 svv si osya, Kk n ZASN, - 2042 sn, s1 osk, Kk n 2-OSNI-s-s,H, - 2045 SNa si osya, Kk H 2.5-4сН5)3-0-С,Н, - 2044 сне 21 ося, B Нн 2-(СЕхаСн-5-СНИ-с-сН, - 2945 ся, си ося, n 9-fluorenyl - 2046 ся, - 2050 sy, si osn, H nn 5-dibenzosuberyl - 2053 s, si osya, NN n 5- dibenzosuberenyl x 2052 s. gi osk, nn s-syn - 2053 s, s1 OS, Kk | s-H, naslo 2054 sn, s1: oOse, N Kk s-sSvN,, - 2055 sn, si osv, NN I" "-S - z056 sn, si osv; NN i ss - 2057 sn, SI osv in n 2-sB, s- САнь - 2058. сн, си ост НН н 3-СН-с-с,Н, - 2059 сн, с1 ОоСся, ВН Кк 2-ОоСНиг сн, - 2060 ся, си ост, Н н 2.5- (СНИ) 1 сНХ , - 2061 sy. si ost, NN | 2-(Stzasn-5-CH,-e-CH, -

2052 st. с1 осе, НЦІ 9- fluorenyl - 2063 Snu Si OsCE, nn n 1-tetrahydronaphthyl - 2064 сн, с1 ос, я n 1-indanyl " 2065 se, Fi osk, NK H 4- chromanium - 2066 sya, 21 Осе, NN H 2-oxo-e-teH, - 2067 sya, si obsya, Kk H 5- dioenzosuberyl - 2oKya sya, b1 ost, V Kn 5- dibenzosoverenyl - 2069 sya, c1 sv, H n -t-Si, - 2079 Sun si sun, N n s-s,v, - 2071 sn, s1 sn, n n s-sa - 2072 sn, si sn, NI. n s-SNz - 2071 sn, s1 sn, n Kk s-sen - 2074 sn, si sn, N H 2-sy,-se-s,8, - 2075 sv s1 sn, I H 3-SN,-s-Sz NE - 2976 sn. si sn, Kk H 2-OSNI- s-C, - 2077 sn, si sn, n i 2.551 as CH - 2078 sn, sx sn, and n 2-1 sЯau sn -8-SNI- ss - 2079 sn, si sia, n n 9- fluorenyl - zov sn, si sv, i n 1- tetrahydronaphthyl - 2081 s, s) s, NN 1-indanyl - 2282 sn, si sv, n ia 4- chromanil - 2083 sk, si CH, N ia a-okets-Sen, - 2284 si, si si n ne 5-dibenzosuberych - 2085 si sv, nn 5-dibenzosuberenyl - 2085 s. sk, SI n i s-SN, - 2087 si

SE. (s NI N s-sv, 141-145 2088 Sn, SE, Si n K s-sen - 2089 sna SE, s1 n I: s-SNx - 2990 sn, sv, si E n s-S z - 2091 sn , Ce, c E I 2-CH-2-c,y, - 27032 Snu CE; (СИ n H 3-СНа-с-СзН, - 72993 СН, CE, си1 n n 2-Оосн,-с-с ,H, - 2294 sya, SE, si H n 2. 5- (SNU) us San - 2095 Shk, sk, si n n 2-(sp,rsk-5-sSnuns-s,, - 2095 СН, SE, si n (in 9-fluorenyl - 2097 sn.

SE, 1- tetrahydronaphthyl - 2238 St; SE, (s n H x-indanyl - 2099 sn, sc; k1 n n 4-chromanil -

2100 en, CE, si n n 2-Okoes-c,, - 7101 CH, CE, C1 N n veDdyShenzosoverenyl - 2102 Sya, SR, si n ya 8-dibenzosoverenyl - 2103 sya. SE, osn, NN Kk s-seN - 2104 sya, svv os non e-sav 103-105 2105 sun, SE, Oosk, M ni s-sna - 2106 sun. SE, ost, Mn pi «-0.Н - 2107 сно сЕ, ос, НН Н с-съН,, - 2108 sya, SE, axis, n 2-сСВИ-с- SN, - 2109 sya, SR, axis, Kk H 3-sn-o-s, - 2110 sy; SE, os, NK H 2-OSNI-s- Sena - 211 sy, sr, osn, VN KE 2,5- SN): s-S,H, - 2112 sy. SE, osn, NN n 2-5 Сски)асН-5-СН-е-с,В, - 2113 sya, SE, Osn, NN Н 5 - flusrenil - 2114 sn. se, osn, M Kk x-tetrahydronaphthyl - 2115 sk, Sk, osn, NN and 1-indanil - 2116 sn, SE, Osn, n t. 4-chromanil - 2117 sv, osn, VN n 1 okoo-e- with, H, -

Thebes SN, SE, OSN; NN n 5 "-diabenzosuberyl - 21195 sia, Sv, osn, E I; 5-Dibenzosuberenyl t 2120 sn. se, E KE n s-sni - 2121 SN; SE, E N n se-s,N, - 2122 sya; se, E n Kk seSuV - 2123 syayi sv, E n Ne e-s 118-122 2124 s, SE, E Kk and s-SoNi - 3125 SN, SB, E Hn n 2-sn-2-s.N, - 2126 сн, св Р n B 3-сн,-с-с,В, - 2197 СН; CE, E n n 1-Oosnu-s- sn, - 2124 CH, st E H n 7.5-(СНИ)ane-С,Н, - 2129 sya; SR E N H 2-iSsKR SN Sny esS,H, 185-156 2130 Sn, se R K H 9- fpuorenyl 184-185 ziz1 sn, st, E H and 1-tetrahydronaphthnl - 2122 sia, sv, E n n 1 -indanil - 2133 sm; se, ЕНН 4-chromanil - tim CH. Sl Her I n 2 oxoe-sai - 2135 SN, sc, E n n 5-DIbenzosuberyl - 2136 sn; sv, E n n e-dibenzosuberenyl - 2137 sia, sy, osp, s, n e-san -

2138 dream sleep, Osn. sn, n 2-S.N, - 2119 sn, sk, basic. sv, n ss, - 2140 sy, st osn, sk, K 2-СН, - 2141 СН, s osn, sv, n F-SoViz - 5142 sn.

Сy, осн, сн, Kn 2-СН,-с-С5Не - 2143 сна сн, оси, сер, Кк 3-сн,- сс - 2144 сн, сн, осн, сн, Кк 2-OSNI-с-с, On - 2145 sk, sn.

OSYA, sn, Kk Zh. 5- (SNU: o-S,N, - 2146 sv: sn, osya, sv and 2-(snYiasy-5-SNI-s-sniN, - 2147 sn: sya, Os, SV , Kk 9- fuusrenyl - 2148 sy, sn. osn, SV, n 1- tetrahydronaphthyl - 2149 sy, sia, osn, sn, Kk 1-indanyl - 2150 sy, sn, osn, sv, n 4-chronanil e 21513 sv , c ost SV, n choyurse-SsuNu - 2152 sy, sn. osn, sv Kk 5-dibenzosuberyl - 2153 sv, sn, osn, sv, K 5- dibenzosuberenyl - 2154, SE, sn osn, si H ssan; - 2155 sn, st, osn, c1 n s-s,N, 115-116 2156 sy. .

OosyaYa, si H 2-x -- sen, - 2162 sn. sn, obsya, si n 2. 8-KSN 2 s-s,N, - 2163 sn, Xia, osn, sI1 N as UsNA5-SNI-s- So - 2164 sy. sn, osn, si H 9 - flusrenil - 2165 SE, sia, Os, «1 n 1-tetrahydronaphthyl - 21664 s sv osn, si H 1-indianil - 2167 sn. c ost, si B 4-chromanil. 7168 SNI sya, osn, s1 H 2 oxsts-sS,H, - 2169 sn, sya.

OosSh, c1 n 5 -dibenzosuberyl - 2170 sia. sia, Osn, SI n 5- dibenzasuberenii - 2171 sy, SV.

Osn.

ЕН с-СН, - 215 сн, SV, OS, EE n с-Сий -

2176 си, сн, оси 0/ю n 2-сн5-о-сН - 2177 СЯ, СН, ОС, Рв я ЗесНс- с, - 2178 Св сн, ОСЯ, и Я 2-сНи-с-сН, - 2119 dream

CH; OSYA, in Ni a.5-4СН;- с -СьН, - 2189 сн, сн, ОСя, (I В 2-(снИсн-5-снИ-е-с,.В, - 2181 sy, sya, asya, There are 9. flusrenii - 2182 sa.

EYU, OSYA, in n 1-tetrahydronaphthyl - 7183 sn.

Sleep osn, E n 1- Indanyl - ziva s with osn, KE n 4- chrokanil - 2185 sn, CH, OS in n vtokoussnO - 2186 sn. c, OS and 5-dibenzosuberyl - 2187 sn: SYA, CH, in n 5-dibenzosuberenyl - 2ivya sn. sun, sun, n sia, s-s.N, - 2189 sun, sun, sun, il sun, s-S.Na - 214th sun. sn, s, n sn, e-s,n,; - 21933 sm. sun, SV, Kk sy, ss - 2192, sch, sn, sp, Kk sia, "bu - 2181 sia. sya, sv, H sya, 2-СН5-с- СН, - 2154 snu sn. sv g: SV z-svu-s-SNe - 21935 sya.

Sn, SK, H sn; 2-осН,-е-СуН, - 2196 сн с, св Н са, 2,а- (СН), -е-сНН, - 2197 сн, сн, с, и сн, 2- сн, сн-Б- СН,-с-с,Н, - 2198 сн, сн, СВ, Ni сн, o va-fluorenyl - 2199 ся; se, sn, K si 1-tetrahydronaphthyl - 2200 sia, Xia SN Kk sn; 1-indanil - 2201 sy, sn, sn, Kk sn, «- chromanil - 2202 sn. sn, sn, n sna 2-okoos-sS, - 220 sy, s sn, n SN; z-dibenzosueeryl - 2204 sy, sn, sn, v sia, «-Dibenzosuberenyl - 7208 s is si n sn, s-sv - 2206 syu, si si N sia, s-Sude - 2207 st si s1 i sn, s- SeNy - 2208 sya, si si k sv e-SUN - 2225 sk, s1 "1 Kk sya, e-SeNiv - 2810 sna. c1 si E si, 2-sNu-s- sne - 2211 s, ss nn se, 3-Sn-s- s - 2312 sia, si1 si n si, 2-Oosk,-s-СН, - 8213 СН, s1 bi n SYA, 2, 5- (SNI -s- s -

2214 sq. si si and snu 2-8), Н-5-СВu-с sv, - 2215 sni si si n СН» h- fluorenyl - ббос б 00б1 00 No sn, 00 1-tetrahydronaphthyl oil 2217 s, s si H st 1-indanyl - 2216 sn, c1 c1 H SV 4-chromanium - 2219 CH, c1 c1 n cv, 2-akoos-s.H, - 2220 cn, c c no cv 5- dibenzosuberyl - 2221 c a si E st 5 - dibenzosuberenil - 2222 sn. sn, osn, SN, H s-s - 2223 sya sk, osn, Osy, H ss, oil 2224 sn. се, ос, ОС В s-sy - 2275 sya. sia osn, axes, and e-Sz Na - 22125 Sn. SN, OSN, SV, N e-SeNi - - tat? Sk. sv, os, osn, VN 2-sn.-s-sN, oil 2229 sn. сн, осн, осн, NK 3-сСИ,-с-с.й, - 2229 сн, сн, ося, осе, МН 2-0сНу-с- С - 2230 сКУ, sya, sya, osv НН 3.5- (СЯ ;-с- SU. - 2231 sk. sn, Oosya, sk, H 2-ISnrsn-Z-sNI- ss, - 2232 sk; se, sv, os o /H 5- fluorenyl - 2213 Sk, sn, sia, osn, NN 1- tetrahydronaphthyl - 2234 sy. CE, osm, osn, H 1-indanyl - 2235 sia, sia, sia, Ost, NN 4- chromanide - 22136 sn, «kN, osn, os, H 2- UKos-s,n, - 2217 sk, sn, osn, OS, n v- dibenzosuberyl - 2238 sn. sn, osn, osn, B 5- dibenzosoverenyl - 2239 o si "a N Kk s-s,n, - 2240 axis, N H s-s,n, - 2241 axis axis NN n s-s,V, - 2742 o s1 zhu, V Hn s-g, - 2243 axis sn, H n e-s,N, - 2244 0 ost is n n s-Sey, - 2245 b SE, sn, Н N s-SN, . с,Н, х -2418 (c) сн, оси, Е Н с-с.Н, - 2249 b сн. сн, н сы, с-сн, " 2259 о чч "ии н сы, с-С,Н , -

Key: a) Spectral data for compounds marked as "oil" are given below:

Example 2003, spectral data: Mass spectroscopy (MS-MS): m/e 374 (MaeN' 10095). Example 2006, spectral data: TI C V; 0.20 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSI"): b 8.94 (1H, 5), 7.67 (1H, a, y8.1 Hz), 7.57 (1H, a, 9-1.8 Hz) , 7.40 (1H, aa, 90-81, 1.8 Gu), 4.83 (1H, a, 9-8.0 Hz), 3.20-3.04 (1H, t), 2, 98 (2H, hell,

CheT7.3 Hz), 2.50-2.38 (1H, t), 2.30-2.15 (2H, t), (2H, bg), 2.03-1.93 (2H, t) , 1.75-1.80 (1H, t), 1.42 (ZH, i, 9-7.3 Hz), 0.68 (ZH, a, 9-6.9 Hz). Mass spectroscopy (MH-SI): t/e, calc. for Sti9NgiSioMa: 375.1143, found 375.1149;

Z80 (2), 379 (12), 378 (15), 377 (66), 376 (27), 375 (100).

Example 2011, spectral data: Mass spectroscopy (MS-SI): t/e 457 (MAN, 100925).

Example 2012, spectral data: TI C V; 0.38 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.94 (IN, 5), 7.72 (1H, a, 0-85 Hu), 7.58 (1H, 9, 9-18 Hu), 7, 47-7.40 (2H, t), 7.24-7.18 (1H, ha), 6.56 (1H, y, 9U-7.7 Hz), 6b.18-6.10 (IN, t), 4.82-4.76 (IN, t), 3.15-2.30 (5H, t), 2.10-1.77 (ZN, pi), 1.27 (ZN, 5 9y -7.5 Gu). Mass spectroscopy (MHz-SI): t/e, calculated for SgZiNgSi2Ma: 423.1143, found 423.1142; 427 (13), 426 (18), 425 (67), 424 (31), 423 (100).

Example 2013, spectral data: TI C V; 0.28 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.91 (IN, 5), 7.68 (1H, y, 9-8.5 Hz), 7.58 (1H, y, 9-1.8 Hz ), 7.46-7.38 (2H, t), 7.22-7.15 (IN, t), 6.91 (1H, a, 9-7.7 Gu), 6.42 (IN, g, 9u-7 Hz), 5.30-5.22 (1H, t), 3.43-3.33 (1H, t), 3.20-3.03 (1H, t), 2.89 -2.76 (2H, t), 2.56-2.43 (1H, t), 2.01-1.90 (1H, t), 1.91 (ZH, i, 9-7.5 Hz ).Mass spectroscopy (MN3-SI): t/e, calculated for Cg2NiOSi2Ma: 409.0987, found 409.0987; 413 (12), 412 (17), 411 (67), 410 (29), 409 (100).

Example 2014, spectral data: TI C V; 0.38 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIzv): b 8.95 (IN, 5), 7.71 (1H, a, 9-84 Hz), 7.59 (1H, y, 9-2.2 Hu), 7.42 (1H, aa, 9-84, 2.2 Hz), 7.26-7.19 (1H, t), 6.98-6.90 (1H, t), 6.58 (1H, y, 97.7 Hz), 6.30-6.22 (1H, t), 4.60-4.53 (Ш, t), 4.43-4.33 (IN, t), 4.20 (1H, Bi), 2.82-2.72 (1H, t), 2.69-2.58 (1H, t), 2.46-2.36 (1H, t), 2.18-2 .08 (1Н, т), 1.29 (ЗН, и, 9-7.5 Hz). Mass spectroscopy (МНз-СИ): т/е, calculated for Сг2НиоСи2МаО: 425.0936, found 425.0926 429 (12), 428 (17), 427 (67), 426 (30), 425 (100).

Example 2020 spectral data: TI C V; 0.43 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.98 (IN, 5), 7.81 (2H, a, 9-8.4 Hz), 7.67 (1H, aa, 9-8.0, 0.7 Gu), 4.26 (1H, t), 3.00 (2H, a, 9-7.6 Hz), 2.75-2.66 (2H, t), 2.06-1, 90 (4H, t), 1.50-1.36 (4H, t), 1.40 (ZH, i, 9-7.5 Hz). Mass spectroscopy (MHz-SI): t/e 412( 7), 411(34), 410 (25), 409 (100).

Example 2053, spectral data: TI C V; 0.36 (25:75 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz"): b 8.96 (IN, 5), 7.73 (1H, y, 9U-8.4 Hz), 7.44 (1H, y, 90-11 Gu) , 7.28 (1H, ai, 9-84, 1.1 Hu), 4.79 (1H, pentet, -8.4 Hz), 3.01 (2H, a, 97.7 Hu), 2, 62-2.50 (2H, t), 2.23-2.07 (2H, t), 1.89-1.77 (2H, t), 1.66-1.49 (2H, t), 1.41 (ZN, i, 9-7.7 Gu).

Mabs-spectroscopy (MHz-SI): t/e, calc. for C1i9NiOSiIEzMaO: 411.1205, found 411.1208; 414(7), 413 (34), 412 (24), 411 (100).

Example 2223, spectral data: TI C V; 0.36 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOCI3): b 8.91 (IN, 5), 7.33 (1H, 5), 6.83 (1H, 5), 4.78 (1H, pentet, U-8, 5 Hz), 3.94 (ZN, 5), 3.90 (ZN, 5), 2.98 (2H, a, 9-76 Gu), 2.58-2.48 (2H, t), 2 ... spectroscopy (MH3-SI): t/e, calculated for SgH27MaO: 367.2134, found 367.2120; 369 (3), 368 (24), 367 (100).

Example 2227, spectral data: TI S A; 0.45 (50:50 ethyl acetate-hexane). "H NMR (300 MHz, SOSIv): b 8.90 (IN, 5), 7.37 (IN, 5), 6.83 (1H, 5), 4.85 (IN, a, U-8, 4 Hz), 3.94 (ZN, 5), 3.91 (ZN, 5), 3.19-3.11 (IN, t), 2.96 (2H, ad, ue7.9, 1.5 Hz), 2.41 (ZH, 5), 2.24-2.16 (2H, t), 2.04-1.94 (2H, t), 1.71-1.62 (2H, t) . »: 381.2290, found 381.2294; 383 (4), 382 (25), 381 (100).

The following methods of preparation of 3-benzyl-5-methyl-7-(2,4,6-trimethylphenyl)-imidazo (4,5-b|Ipyridine (Example 3001, Table 3) can be applied to obtain all examples of compounds of Structure A in

Tables C with minor procedural modifications where necessary and using reagents of acceptable structure.

The methods shown in Schemes 13 and 14 can be used to prepare many of the example compounds of Structures B and C in Table 2 with minor procedural modifications where necessary and using reagents of acceptable structure.

Example 3001

Preparation of 3-benzyl-5-methyl-7-(2,4,6-trimethylphenyl)imidazo|4,5-5|pyridine

Part A. A solution of 2,4,6-trimethylbenzeneboronic acid in benzene (0.5M) is treated with excess p-butanol, and this solution is heated in an inverted condenser with a Dean-Sears distillation head for azeotropic extraction of water. The solvent is removed by evaporation, and the resulting dibutyl 2,4,6-trimethylbenzeneboronate is used directly in Part B.

Part B. In this case, the method of Snikus (Zpiveskiv) and others can be used. (By, 9U.M.; 2Nao, V.R.;

Zpagr, M.U.; Zpieskiv, M., Sap. 9). Spent 1994, 72, 227-236). According to this method, a solution of 4-chloro-b6-methyl-3-nitro-2-pyridoimine in dimethylformamide (0.1 M) is treated with boron from Part A (1.2 equiv.), tribasic potassium phosphate (2.4 equiv. ) and 1,1'-bisidiphenylphosphino)-ferrocene|dichloropalladium (0.1 equiv.). This mixture is stirred at room temperature for 30 hours, then poured into 4 volumes of ethyl acetate. Then wash with equal volumes of water and then with brine. The extract is dried over sodium sulfate, filtered and evaporated. Chromatographic separation leads to pure b-methyl-3-nitro-4-(2,4,6-trimethylphenyl)-2-iridone.

Part C The pyridone from Part B is suspended in 6 equiv. of phosphorus oxychloride and then stir under gentle heating until this compound dissolves. This mixture is cooled and poured onto ice. After melting, the mixture was extracted twice with dichloromethane, and the extracts were combined, dried over sodium sulfate, filtered, and evaporated. The resulting product, 2-chloro-6-methyl-3-nitro-4-(2,4,6-trimethylphenyl)pyridine, is purified by recrystallization or chromatography.

Part 0. Chloride from Frequent C is dissolved in ethanol and treated with benzylamine (1.2 equiv.). This mixture is heated with an inverted refrigerator until the starting material is absorbed, which is monitored by thin layer chromatography. The mixture was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer is separated, washed with brine, dried over sodium sulfate, filtered and evaporated. The product, 2-benzylamino-b-methyl-3-nitro-4-(2,4,6-trimethylphenyl)pyridine, is purified by recrystallization or chromatography.

Part E. The nitro compound from Part Y is dissolved in 1:11 aqueous dioxane and treated with conc. aq. ammonium hydroxide solution. Solid sodium dithionite is added to this solution in several portions over the course of 2 hours. This mixture was further stirred for 4 hours, then partitioned between water and ethyl acetate. The organic layer is separated, washed with brine, dried over sodium sulfate, filtered and evaporated. The product, 3-amino-2-benzylamino-β6-methyl-4-(2,4,6-trimethylphenyl)pyridine, is purified by recrystallization or chromatography.

Part R. A suspension of the diamine from Part E, above, in triethyl orthopropionate is treated with concentrated hydrochloric acid and heated with a reflux condenser for 1 hour, then cooled and the excess orthoether removed by vacuum distillation.

The residue after distillation contains sufficiently pure /N-(2-benzylamino-4-(2,4,6-trimethylphenia)-6-methylpyridine-3-s|Ipropionamide O-ethyl imidate.

Part C. A solution of the compound from Part E in phenyl ether is treated with a catalytic amount of p-toluenesulfonic acid and heated to 170°C for 6 hours, then cooled. The residual liquid is separated by column chromatography (hexane, then ethyl acetate) to give the title product.

TABLE 3 4 Kk. X si yy Z i z

V z M ry M sy -x-K | i sna - kn i i SNI -x- | Mizi is also 1 of HER and "M i y".

KB Ka Ko ve ve ka

Wee Wee Kee

Nv E5 ke (A) (B) (c) under inii ion in ono un-t oon chemni b CHARMERS evacuated

Tpl.

Mpricl. HO LANGUAGES what ra i ni pi i dno ii NN SN S OON z0a7 sn, si si Н n si-ORtOS,N, - 3002 sn, si «1 n n si-osos,n, 90-91 3003 sya, s1 SI N n Sigoosk, 57-59 3004 sy, si si ik n si-oOzosnisN,), no-a81 1005 se, si ai n n SOS NISN,) Z 6520-62 3006 sn, s si n n si-oNsNI -

VN sn, si si N H sigOo)n(SoH,) 120-121 zrov sn, sii si re i so) nisn(SY, 21 147-149 3909 sy, sk1 si n n Sizo) (1- morpholinyl I 158- 159 3910 son, si s1 n n 50SENE 132-133 1031 sn. si s1 n ih 50, (4-SN.U-S.N, | 154-155 zm12 sn, si s i! n 50.013-OSNI-sN, 155-158 3913 с си сИ1 ВН з0,-(2-thienyl | 176-178 3014 сн, с1 си n n n BONN 127-129 3915 ся, SI си n I BOS, 100-161 3016 сн, си st1 n nn Oman 79-80 3017 syn, s si Kk N Sbeo1-42-s1-s,N, 110-113 3018 sn, si SE, n n se) Osa, - 3019 sy, si SE, n n si-Fshchoos,n , -

from 22 pm si se n Kk sse-los,n, - 3021 sk. si se, N V si O1OSNISN,), - 3022 sk, si sv, K N si-OzOSsN.sNIsSN, - 3023 sya; si st, Hn in Ssi-O) (SN); - 3024 sy; si SEZ Kk n s(-0) (SNU) 2 - 31025 sn, si sv.

Kk n Si50)NYSNISNU) z) - 3026 sn, c1 st Kn Vo sSio! (1- morpholinild !/ - 3027 sya, с1 сЕ, Н H 505, | - zozya sia. si sv, н n 50.14-СсНИ-С,Н) is 3029 sn. si syu in NI BOo,c4-Oosn,- SN - zozo sn. si sv, N n 503-(2- thienyl. | - 3031 sn, s1 sta n N osy, - 3012 sk. si sv, n n tele y - 3033 sv s1 sv, N n BOS. - 3034 sy. s1 F . si osn, nn n sikhozos,N, - zozv s osn, s1 ost, NN i si OrOSYA sn, - 3019 sn, si os.

Kk i si ooSM,sN(SIU, - 1940 sya, s1 osk, N k si-01 (SNO; - 3041 sn. sF1 ost.

VN n Sion.) - 3042 sno c1 axis, B " C(-oMISNiCH,)g)1 - 3943 sno si axis, Bn si-or(1-morpholinyl. | - zo44 Se si osv V n BONN, - z045 sya, "1 osv, nn H 5o(4-СсН,-Сси - 3045 sn, s1 ost. nn n 850.14-ОСН,- Св - 12047 sya, si os NN H 50,-12-thienyl. ) - ziv sn, si osn, V n 50, - 3043 sn, si ost NN n 802, x 3059 sy. . -

3058 dream si ost V n sms, - zo59 sn, cS1 OsSE; N N SIEOINISNISN gg - zoB0 sn. si osv N n Sig03(1-morpholinl) - 3061 s ti osv, В Н 50,s,Н, - 3052 sn, Si osv, Mn n 5014. svu-s,VY - 3063 sn, s1 ost, NN N Bo , 4-Oosnu- s, - 1064 sy. 21 ost, n 80,-(a-tienilo | - za65 sya, s t; nn y Bonn, - z065 sn, Si OosE, V N 80.s5N, - zp87 sn, gi os, n N BONNY - zs68 sna si Here, NN N Siz«br-(2-s1- 0, - zov sn. si sv, n N s1-010s,n, - za70 sn, si s, N n siza)0s,n,

3071 SN. s sn, n H si-oos,n, - 3072 p. spis yK N sor OSN(SNI) r - 3073 sk, s sn, n N si-o1osnUsNsN, - z074 sya, 541 sya, N n siOum(sn, - 3075 sni s1 sn n n sgz0 Syan, z - 3076 sn s1 sv, n n sizounISK(SNYI 12 - 3077 sn. si sv, n nO00os(х0111- morpholinyl ) - 3078 snu. si sv, Н N BOS - 3079 Е, si s, and n bo, 14-sn-soi - 3089 sx, si si N n 5Oo. (4-OoSNI-sNY - 381 sp; si sv h H 50.2 tienii | - 3985 sk. si sia, g i BOZHN,V, - 3083 sia, si sn, n n 505С38" - zova sn, si sn, n n osiv, - zode sn, si sia, N ksi-01-12-с235-С,Н1 - 3085 SN, SE, s1 h n Si«OzOSaN, . zorya sn . , - z0ch1 sn. sk, 1 n N syzo)(sn.), - 3092 sna st s I N sfiaORngsN,), - 3091 tn, SE, si n K sigOIMISNISN,) 215 - 3094 svo sk, s1 n n si -01(1- morpholinil | - z295 sn, sv, si Kk n vozham -

3096 sn, SE, 1 k and 8O»i4-СсН, с) - 3097 сн, Ск, с1 PI NI 50:14-OSN,-СеН - star sne Sk, с n v 50, (2-thienil.D | - 3099 SN, sk, si i n won - z10o sn, SE, si Н H 5OXYA, - 3101 Сн SE, /с1 В n 505сНе - zida sn. st, si Н H сСи«0-(2-с1-с ,No - 3103 sia.

SE, Xia V N si-v10son, - zisa sn. se, wasps, V n si-oosn; - 3105 sun, SE, sun, in E sg«oos,n, - 105 sun, Sun, sun, N N SsI-OOSNISN, 1 - 1107 sun sun, sun, in N sosnu SN z - ziva sb se, sun, NN N SizO)MISN,) 4 - 3109 sn.

SE, Osn, c) In si0)MmisUih - 2110 sn, sv, osn, KN n C(ig0RM(СН(СН) з)) - 3112 sn, st osk, M ko sb-0u02- morpholinil; - 3112 sn SE , os, V n 50, - 3113 sn.

Sv, os, NN n for a-snI sy - 3114 sn.

SE, osn, H n hoO, (4-osn,-сС,Н, - 3115 sn. sk, osn, KN n 8b,-(2- thienyl. | - 3116 sn, sk, os, Kk NI. 5o, bachelor's degree, - 3417 bachelor's degree

SE, wasps, Kk n O.S.

N, - 3118 sv, SE, os, NN Nn BOo,s,y, - 3119 sv, SE, os, NN n s(50)- (8-21, - 3125 sn, sia, t n n SikhaTas,N , - zhihi1 sn, SE, E n N Si5010s; NI - 31322 SYA, st E Kk n se-o1os,, - 1173 SN, SK E n n sSe«OBOSNISNII HU - 2124 sn, se in N n se-ozoSTsSN( SNI - 3125 SN, SE, E N i si) MisN.)x - 3126 Sn, sv, E B n si20) (SN) - 31127 sya, sk, E N n SgeOHMISN(ISNU) 515 - 3128 sya, SE.

E B i c0-9355- morpholinil ) - 1129 SY.

SE, E N n selovey - 1130. SN, sk, EE n n 5O, (4-СН,-С,В,) - 1131 sn. sv E N H 50o. (4-OSN,-Suv - 3132 sya, sv, E N H 5o.-IZ-tisncil. | - 1133 SN, ST, EE in N BONsNaСН, -

3134 SK. St. E n n es. 7 3135 sk, sk, E n Hn 5OSN, - 3136 SE. sya, E n n C(zbr-(2-с21-с;Н - 3137 Sya.

Sn, osn, sn, n SfieOo)Os,N, - z118 sn. sk, sk, sn, N Sieo)os,n, - 3129 sni sn, osn, su, N Si«OzOSs,N, - zi4o sn. sn, OoSYA, sn, n Si«OrOSNISV,). - 3141 sv, osn, osn; sn, NN sikhO1OosTSN (SN, - 1142 sn. s, osn, sv, N so )KTSN(СНХ)" 13 - 3145 sn; sn, osNU st Bo 00 sik0111- morpholinil o ) - 3146 sn sy, osn, SN n Osa - 3147 sn, sn. osn, sn, n 50515, SYU - 3148 sn. sn. osn, sn, E 54 OSNI-seschi - 3149 sk, sn, Os, SK, n 50.-(2- tienil. | - 1150 sk. sv, ost, sn, n osn, - 3151 sya, sya, osn, SN, n Bon, - z153 sn, sya, osn, sn n Statei, y - 1153 sya SE Osn, SV, n sfor-(2-с1-seN, - 1154 sk sn, osn, si n sg-0 )os,N, - 3155 s. sya, yuosya, si N sigvrosuv, - 3156 s. sn, osn, s1 n b efeo)os,V, - 3157 sya; sn, OoSnu sI1 N SihOTOSNISNUYA z - 1158 s. sia , osn, si n sigoosnIsnisn,). - 3159 sn, s, Os, si N SgeOIM(SNI) with - 3180 Sn.

Xia, Os, si n si«o) n(S,N.); - 3162 sne svo asn, si n si-0UMISNISN,) 14 - 3167 sn. c OosYaya, c1 n cSyz0)311-morpholinyl) - 3163 sya, sya, osn, si In BO,S,n, - 31654 sk, ev, osn, si n 50,14-СН,-С,Schi - 3165 sn ; sn, oSya, si I kazs4-osN,- СН) - 3165 sn. sia осн, ги п что.-(2- tight - 3157 s sia, sv s n vostsen, - ziva St. sn, OST, s B 50, - 31659 Se sn, osv, si N BO - 3170 sn, sia, osn -

3172 sn: s, OSN 0 N si-okos,n, - 3173 sya, Sn, OS, in n si«ozos,V, - 3174 sn, sya. educational institution, E N SiIkOT Osn SN". - 3175 sm, SE, OS.

SE n sfiveorosNNisN.), - 3176 syu sn, OS, in n sin OK (SN, - 1177 sn, SV.

Osn; (EE V Seh0)1M(SzNeY; - zitya sn, sn, OSE, R ia SO NISN(IS 313 - 3173 sn. st, osn, t n siori1- morpholinyl U - 1189 S.

NE, OS in n 50, s, n, - 2181 sn, S b in N 50O.14-SNU- S - 3187 sy, sn. OSN, E and 50.14 OSN, - S.) - with 83 Sn. sn, asn, KE NE 50.-12-tienilL | h 3184 сн, сн, ОС, is n OSNO, - z185 сСХ, Sp, OSN, EE and BO, - 31665 св со ОС, is Н 5О.С,Н - 3187 сн.

SV, OSV, v n сСивОо)-(2-с1-С,Н - зивв сн, сн, сн Кк сна Си«010ОСоН - 3189 СН.

Snu SN, H sn, si-0Tos,, - 1192 sn. snu sn, n sn, sichoTOsСІ - 3191 sy, Xia, sn, N sn, «sk(etoOsnisn,); 13192 sun, sun, sv, n sy, SihOrOSISNISN,. - 2193 sm. dream sn, H sn, sieozn(SE,),; - 2194 sm. сн, с, Я сн, сие0)М(сня - 3195 сн, ся, св, Н сн, си«О)Ммисниисни 41) - 3196 се, сн, SK, Кк сю, сСбя0111- morpholinil | - 3187 sk, sn, s Kk sn, vas. - 31198 sn, st, se, H sn, ko. (g4-сSNi-SN,) - 3159 sya, sya, sn, E sy, vo;ia-osn, sv - 3200 sya, sn, s, n sn, BOa,-(y-tienil | - 3205 sya, sya, sv, H sna, oz, - 3292 sna. sna, sna, I sv, 50, - 21203 sna. sya, sva, N sv vo.san, - 3204 sy, sn. sv, n sia, si-0)-12-021-0 - 205 sna si s1 n sy, s(-010сUN, - 3205 st, si s N sk, sSi«OrOs,N, - -

1210 sk, si si N sn, Si«O1SN,I, - z211 sn, si si n se, seevIshO1 - 132172 sna si si n sn, si-OUschISKISN, 1, - 17213 sn, s1 s n snu. 0 cSbeor(1- morpholinyl | . 1714 s, si si n sn, BO,СН, - 12165 s, si si n sn. 5O,(4-sNisH,Y - 3216 s. si se in CH, 5054-osn, s - 3117 sy, "g" and n SV. 5O,-a- tieni - 316 sp, s si in sia, BOSNSY, - 3213 sia, ach si and sn, von, - 3220 sv, s s1 and sy, 50 , - 3221 sia ss K sia, Sikou-(2-601-0,NY - 3222 sia.

Xia, osXia. oS, N si-0)K,, - 3223 sn, sn, asn, asn, V si-oroye,, - behind sn, sn, osya, osya, V st«OrOSiV, - 3225 sn, sya, os, ost , I sSikoorOsSNysya.) - for 25 s, sy, Oose, OSYA, and sisoOrosnynisY,) - 3227 st. sya, osv, osn, n Siza)vesy,), - 32238 sn. sn, osn, osv, and c1-01(SN), - 1225 sn.

Sn, ost, osv, and Zion NE, 4 - 3230 sy, sya, N, os, V Siv) (z-morpholinil) - 3233 sn, se osv osn and VO»s;nya - z237 sya. sia, os, os, V zo 4-sn,-s,schi - 31233 sn. с, ос, ос, Н 5о:14-Оося,- си, - 3234 сн, ся, ося, осн, но 5о,-и2- thienil. | - 3235 Sn, sn, osn, os, " Bona, - 3236 sn. sn, osn, osn, p «bin, - 323u7 sya sv, osya, osv, VN von, - 3238 sn, Xia, osya, osn, N si-0r-(3-Cs1-CH - 3239 o si gi Н H Osn - 3248 o С1 st, Kk n 50os,Н - z241 o si osn, nn n BOS - 3242 o; si osv, nn h OS a 3243 1244 1244 1244 1244 1244 1244 1244 1245 1245 1245 AND

3248 o 000 sya, osn, is n 5. and 37249 o S, Sk, n sn, BOo,,n, - 3250 o s1 sh p sy, vovszna . 3253 sy; si s1 n H SevOo)-43-s1-S,H,) 115-I18 inet in bin V OV o .

The methods used to prepare the compounds of Structure A in Table 1 can be applied to the compounds

Structures A in Table 4. For example, replacement of benzeneboronic acids in a palladium-catalyzed aryl cross-linking method (see Examples 35 or 831) with variously substituted pyridine- and pyrimidineboronic acids will lead to the desired b-pyridyl- or b-pyrimidylpurine compounds.

The methods shown in Schemes 13 and 14 can be used to prepare many of the compounds of example Structures B and C in Table 4 with minor procedural modifications where necessary and using reagents of acceptable structure.

TABLE 4 1 niv and kiv viv v de V Z Me Z she , and sleep -k-X | z, sy" -x- | Sn -k

We are 5 and i "t I ih RE - Mi kb ki ke Ko ke di il y che ë

Gi VA Ya

IA, 3; (b)

Application -хХ k 7 V Uch eatE V vi» pl pyt i t t p i i i t 4002 sn, sv, s mis, Mn sv. s-sN, - 2093 EI sn, sno visn), Their KE Sen. 2-3 Well - from 004 sia. si, sko visn); Mk sny --ov - 4005 st st sno city. My sleep, s-S,H, - h005 SNI SN Sn MISNI): ZM n Snu SN - 4027 sn, sv, svo Mis, Mo n sanu sn, -

Fovya sn, sya, so visn), Mo sv, sn, - avoz sm, sn, so visn), Mo p sk. s, - 10190 se, sun, sno shesvi: Mo p h 4-sshcho-s,k, - 1911 o sun, sya mis) No oe-S,V. ssh--S.N, - 4012 s sn. sno month), Z no sv, e-S,8, - 4013 o sv sno Visn Mo N sin; s-sUN, - 1014 o svo sy mis), mo i s, s-S2H,; there is 1015 o'clock sno wisn) o N sno, s-si, - 4016 o sno, sya schi), con NE, sno, - 4017 o si, skomsni, ko no s, sv, - 4018 o sno, si miss ), M no sv, S.V, - 4013 Ges sv sno shshsn, Kv sv siv, - 4020 o sn sn mis), Mo i N a-snUO-sen, oh 4021 s, sy, SN se, MO svo -СН, с-с.Н, - 3025 сн, СН сн сн, M сн, se, с-с, -

2033 sn, s, SN sna no osya, Sai sv VI Y 4024 sn, NE, se SN m sn, s, s-s,V - yo25 sn, sn, sy sn, M sya, sv, 2-S,N , - 4b26 sv, sn, sy sn Mo sn, s, s,n, - b27 sn, sv, sn sn, M sn, s, SON, - ch0za sv, sn, sn sn. mo sia, so s.n, - 4029 sn, sn, sn sn sh sia, st, san. - 4030 сн, св, сн СН, m св, in 4-СНаю-с,Н, - 4031 о сы, сн сн, Mo св с-свн с-с,н, - 4032 а сы, сы snu m o sya , sk, e-sN, - «033 o sy, sy sn, m sia, sv, s-s,N. - 4034 o sna sn sy, M st, ev, --сН, - 4035 o sya, sy sn, m sn, s, e-sN - 2035 o sn, sn sy, m sn, sk, SN, - 4037 G » snu sn sn, M st s, S.V, - 4038 a sn, sn sia, mo sn, sv, sn, - 1035 a SV, sk sy, m s, sya s.K, - 4940 o sv sk SN . m st n a-sn-s,H, - 4021 sn, sya, si SN, M No e-ye, sp-FN, - 4942 sn, sn, sk SV nn on sn, s-s - 4043 sn. sv, sn SN sho n sin; s-sYa, - 4044 st, sn, sn SW, m n s, s-sNe - 045 sn, st sn BSN, mn sen, s-o. - 4046 sn, sv, sn 5SN, nn nn sna SV, - 4047 sn. sv, se 5SN, M nn p. y - «od sia, sv, sna yasna Mns Sun - 4049 sia. Sat SN Sn. i in siy, s.n, - 4050 sy, sn sn SN i: SHY H 4-so-s,n, - 4051 o and He vSNa Mn o e-v, s-Sy - 4257 o syu, SN BSNI m kn sn, s-S,V - 4053 o sia, SE 5SN, Mn sna, s-SON, - 4a54 o sn sn SYA, m in son, s-s, - 4055 (o so sia 8syaya.Y chno sv, s-szn, - 4o55 o sn, sc 5SN, M nn sv, s.n, - 4057 o sy, sy BSV, nn Kn S.V" sn, - 4058 o s. sya yaeSYA, Kk in sn, s, n, -7 4059 c) sn, sn SN, M nn saBa san, - 4065 o st se sn, M v Kk a-sn,a-Snu ,

4061 dream sun, M sun, Mo vSnu s-S,v, «-sun, - 4062 sat; BSK s mo BSN, sn s-sK, - «obu sya s Kk sn, mo vya, s se-sUy, - 064 sn, Bs, M se; ko 5Bs so, s-SaN, - 4065 sk, VS NN sy, mo Zstv sv, e-P,N, - 4065 sya, SN, and SN m ven, sv, syn, - aobt osv, ВС Ш sv, Mo BSYA, SV syn, - aobvv sn so In sn, m vsn, sy, syn, - abz sya, Sun In sleep Mo Yasya, s sn, - ato sya; BSB M sn, mo yasn, but a-snyu-sS, - 40710 5Zsv, and sv, MO sv, o-SU5 00os-sSsh, - 10720 ВС M snu mo all, s s-sSv, - 40730 BO, M sn . , s, sya, - 4077 o VSE, M. sn, km vsa, szh, san. -

Thursday at 00:00 a.m., Mon, 8:00 p.m.; - 40790 B5СЬ M stv mo SN, sDe siv, - 408 o BsSn, her sleep M 5sn, /Н 4-сн.о-с,Н, - ovi сн, svo i сн Mo Su oseСunu 0 e-сy - 4082 сн . 4th sn, sn, n sn; M sya, sv, 2-sU, - 4085 sya, sv tsk SV m sya, s s-s,N, - «086 sya, sv, M sm m syu, sn, sv, - 4087 sn, sv, V sy M sya sv siv, - aoBE sk os Mn sk, Mo osv sb s,n, - 089 sv; svo M sn, m st, sv, s.n., - 4090 sya, sya, MK sn, mo sn, 00 4-sno-si, - mya oso on sn, oosya os-s, 0oe-soV, - 40920 sv Kk sn, mo sn, st s-Sai, - cho93 osv kn sn, m sv sv, s-sun, I 034 os Kk sn, m s st, s-szN, - po boss M sn, I sv sa, ss, - 40960 svv mM se, mo sy, sv, sv, - 40970 s, M sn, mo sy, SV sv, - 40980 st M sv, Mo ost, sv siv, -

4099 s sv, M sn, MO yen, sv, sen; and there are 4100. sun, M sun, M sun, Not 4-sun, Uo-s,n, - 4101 sun, St. сн сн, "и НОоос-сн, с-с,н, - 4102 СН, сна СН ся, М н сн, с-г, н 4103 ska сн, сы СЯ, M Нн сн, с-с,н, - 4104 SN SN, SN SE, M n Sin, s-S.N, - 4195 SN St, SN SI, M N San, e-s na - 4106 SV, St SN Sya, N N SV, s, - o?sk sn, sn sn.

M V sanu San - 169 sy, sya, sna sia, kn n sna, SN, - 4109 sna, sna, sk sna, M n san, s.n, - 4114 sk, sv, sna snu KI n H 4-snu -s,N, - 4111 o sleep, sleep sleep M H s-s,V, s-s,n. - 4112 o sn, sn sy, M H sn, s-s.N, - 4113 o sy, sk sn; v n san, sk-S-:n, - 4114. 0 sn, sn- sy, M n sn, e-sSUN, - 4115 s sn, sn SNU Kk n s.n, k-S.N, - 416 Ge) sn, si si, M N sn, sv, - 4117 o s, si SNI and Kk Snu Sun - 4118 o en, sn sn, K n SON, sn, - 4113 o sy, sn sv: ШЙ СНu, sn . SNO no s-ssh, s-g, - 4122 sni sn, M nis, son sn, e-SN, - 4123 sn sy, M Mmisny, so S sk s, «-S,n . 41374 sv, si, M ms), sno on sn, s-s, - 4125 sn, sn, i shkisn,), SE nd San s-SzN. - 4126 Sv, Sn, I Shen, Sok SN) Sn, - 4127 Sv, Sn. no zhshshsvi)., skovn SON, su - 4129 СН сн, Ya Best) son syn, Sn, - 4129 sya, sk ko zhisn,), sok s,y, S.V, - 41530 сн, сн.

Kk shchen). sok n 4-sp., o-sn, - 4131 o sv, 8 osn). so V se-S,N, s-sschn, - 4132 o sn, no nose, Sun sia, s-SUN, - 41133 o sv Ko m(esv,y, sok sen, 2-SIN, - 4133 o sn, m ooschen), sec ost, s-s,Nn, - oh, 4135 o sn, no shsn,;o, s Kk Sanya s-s.n, - 4135 d) sn, mo zhshsv,), so Kk sya, S.V, -

4175 o o.s.n., In o.s.n. s no s, s-sv, - 4176 o OSY; m os sno n SNU zn. - 4177 o o.s.n., M o.s.n.; sn nn st San, - 4178 o osv, m osn, syn su, SzNa - 4179 o os, M osn, sy nn sya, seV" - 4189 o os; M os, SN nn n 4-snIo-siv, - 4181 sya, OS MO shSHSVY, SON os-SW s-suN, - 4182 sE, axis, M axis, sko N sn, s-sn, - "183 sy; education, mo. sno i 0 szh, s-SiN, - i184 sno, osya, B o schen), sno no os, s-sy, - 4185 sno, oS, M Mshisn)yi sno no o s,v, s-sn, - 4186 sia. os, Mo mis, son sia, S.V, - 4187 sn, os, M cysts. sno nosy, s.n, - 4188 sya, os, Mo snu, so no su, p. - 4189 sn: osn, Mo shen), SN nosu, sv, - 4190. sn; os, in shsvu sr n H 4-snyu-sen, - 4191 o os, 8 Mis), sn No s-ssh, e-S,N, - 4192 o osv; Ministry of Internal Affairs); sno SN sy, s-sW, - 4193 o osn Mo venY), SNO no osv, s-sy, - 4194 o osn, M shЖs)U sno sia, s-s,i, - 4195 o os, mo ve) . , sno no s, sno - 4139 o os. MM month), Sun No s, Sen, - 4200 o ost mo still). sv n 4-sn.o-sn, - 4201 sv, MISNI M oS. sno no s-s, s-san, - 4202 sn, MISNI): In osn, s in sn, s-SUN, - 4203 Sn, (SNI): M" osi, sya no st, s-sy, - 4304 sn, (SNY: M osya, sya vo s, s-S,N, - 4205 sn, MmIsn,. M osn, sya kn sv e-sN, - 4305 sya, MshsN,).; In axis, sno Kn st sia, - 4207 SN, MISNI), M Mosn. SN no SV, SN, - 4208 SV, msh(SNII, M Mosn. SN no st, SV, - 4209 SN, all), M ost SN no SV SN, - 4210 dreams; dreams.

M os. sno kn H 4-Сн,О-с,н, о 4211 о ше), in осн, СН Но с-сж, "-СН, - 4212 о шсн,), M ос sno in sv, s-с,8 , -

4213 9) shIsn.i, osu, sn K sn, s-sN, - 4214 o MmIiSN,. M osn, sia N Sun. village Sn. 7 4215 o M(SN.ua M osn, SN В KN, s-sN, - 4216 0 MisnY, ZhK osv, SNO No 0sn sn, 7 47217 OO Sh(SYA,) I. osy, SE nn son, s, - 414218 o mshesn,, M ren, sn n sn, sn, - 4219 0 k(sSnu M osn, sn n sS.n. san, - 42200 msh(snY, MO osn, SEN no a-svo-s,v , - 4221 c, sk, |z! OS, sn Sy. 0 2- fFuranyl - 4222 sy: Os M osn, sn no Co 0 3- Furanil - . 4223 sn, osn, M oxy, sn n sn, b - 4224 СН, осн, и оси, си н сн, и - 4225 с ос, Ж ос, ск сен, з. sno os, 0 snASKV - 4229 sn, ov, M osn, sn Kk sS.N s.sn, - 4229 sya, os, M osV, sn nn sy, sen, - 230 sn, os, (F os. sn nos s-san; 7 pi.

Key: a) For the compounds marked as "oil", the spectral data are given below:

Example 4166, elemental analysis: calc. for С1и9Но5М5О2 C 64.20, H 7.10, M 19.70; C 64.13, H 6.67, M 19.30 were found.

Example 4171, elemental analysis: calc. for SgoNgzM5Oz C 62.98, H 6.09, M 18.36; C 62.80, H 6.10, M 18.19 were found. p) C-0-CH,

The methods used to prepare the compounds of Table 1 can be applied to the synthesis of the compounds

Structures A in Table 5 and Table BA. The methods used to prepare analogues bearing the benzofuran group are illustrated in the following examples.

The methods shown in Schemes 13 and 14 can be used to prepare many of the example compounds of Structures B and C in Table 5 and Table 5A with minor procedural modifications where necessary and using reagents of acceptable structure.

Example 5001

Preparation of 9-dicyclopropylmethyl-8-ethyl-6-(b-methyl-2,3-dihydrobenzofuran-5-yl)purine

Part A. A dispersion of sodium hydride in mineral oil (5.05 g, 50 wt. 90, 105 ml) was washed with hexane and dried under vacuum. OME (100 mL) was added, and the suspension was cooled to 0°C and treated with a solution of t-cresol (100 mL, 95.6 mmol) in OME (20 mL). The resulting mixture was stirred for 1 hour, then treated with chloromethyl methyl ether (8.00 mL, 105 mmol). The mixture was stirred overnight and then poured into ethyl acetate (200 mL). It was then washed with water (3x20 mL) and brine (1000 mL), and the aqueous phases were successively back-extracted with ethyl acetate. The extracts were combined, dried over magnesium sulfate, filtered, and evaporated. The oily product was purified by eluting through a plug of silica gel with 10:90 ethyl acetate-hexane. Evaporation gave the pure product, 3-(methoxymethoxy)toluene, as an oil (13.3g, 91.5 mmol, 9695 ). TI C Ah 0.46 (10:90 ethyl acetate-hexane). "H NMR (300 MHz, SOSI»v): a 7.17 (1H, 5 9-7.7 Hz), 6.86-6 .81 (ZH, t), 5.17 (2H, c), 3.48 (ZH, 5), 2.33 (ZH, 5). Mass spectroscopy (NgO-C2C/M5): t/e 153 (60), 121 (100).

Part B. A solution of 3-(methoxymethoxy)toluene (5.00 g, 32.9 mmol) and TMEOSA (M, M, M, M-tetramethylethylene diamine) in TNE (500 ml) was cooled to 0"C and treated with a hexane solution of butyllithium (22.Oml, 1.6M, 35.2 mmol). After 4 hours, this solution was cooled to -78"C and treated dropwise with ethylene oxide (2.00 ml, 40 mmol, which was condensed from the flask through a cold tap into a graduated dropper watering can). This mixture was stirred and warmed to room temperature overnight, then poured into a saturated aqueous solution of ammonium chloride (120 ml). It was then subjected to extraction with ethyl acetate (2 x 120 ml), and the extracts were washed successively with brine, combined, dried over magnesium sulfate, filtered and evaporated. The residual oil was separated by column chromatography to give the desired product, 2-(2-(methoxymethoxy)-4-methylphenyl|ethanol) as a viscous liquid (2.25g, 11.5 mmol, 3595) and 2.50g of regenerated starting material. "H NMR spectrum revealed a regioselectivity exceeding 10:1. TI C B; 0.09 (10:90 ethyl acetate-hexane). "H NMR (300 MHz, SOCIv): a 7.06 (1H, 5, 9-7.7 Hu), 6.92 (1H, Bi 5), 6.78 (IN, rg a, 9u-7.7 Hu), 5.20 (2H, 5), 3.83 (2H, a, 9-64 Hz), 3.49 (ZH, 5), 2.89 (2H, i, 9uU-6.6 Gu), 214

2.32 (ZN, 5), 1.61 (IN, i, U-5.9 Hz). Mass spectroscopy (MS-OSI): t/e 214 (76), 212 (100), 197 (9), 182(30), 165

Part C. The MOM solution of the compound from Part B (1.84 g, 9.38 mmol) was dissolved in 1:1 TNE-isopropanol (20 mL) and treated with NOS in dioxane (2.5 mL, 4M, 10.0 mmol). The reaction mixture was stirred at room temperature overnight. As a result of aqueous treatment, a fairly pure product, 2-(2-hydroxy-4-methylphenyl)ethanol, was obtained.

Part 0. A solution of the diol from Part C (ca. 9 mmol) and triphenylphosphine (2.83 g, 10.8 mmol) in TNE (20 mL) was cooled to 0°C and treated with diethyl azodicarboxylate (1.7 mL, 10.8 This solution was stirred overnight, then evaporated, and the residue was separated using an evaporative column to give the product, β-methyl-2,3-dihydrobenzofuran (780 mg, 5.81 mmol, 65965).

TI C B 0.29 (2:98 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): a 7.07 (1H, 6 9-74 Hz), 6.66 (1H, a, 9-74 Hu), 6.62 (1H, 5), 4.54 (2H, i, 9U-8.6 Hz), 3.16 (2H, i, 9-86 Hz), 2.30 (ZH, 5). Mass spectroscopy. (020-(2C/M5):t /e 135(100).

Part E. A solution of the above compound (780mg) and M-bromosuccinimide (1.24g, 6.97mmol) in dichloroethane (10ml) was heated under reflux overnight, then cooled, filtered and evaporated. The method of column chromatography (hexane, then 2:98 ethyl acetate-hexane) gave first 5-bromo-6-methylbenzofuran (27Omg, 1.27 mmol, 2295), then 5-bromo-6-methyl-2,3-dihydrobenzofuran (923mg , 4.33 mol, 7595), both compounds in the form of a solid substance. For the dihydroproduct: TISE: 0.35 (2:98 ethyl acetate-hexane).

T"H NMR (300 MHz, SOSI3): a 7.31 (1H, 5), 6.68 (1H, 5), 4.56 (2H, and 9u-8.8 Hz), 3.17 (2H , i, 9U-8.8 Gu), 2.33 (ZN, 5).

Mass spectroscopy (NgO-2C/M5): mp 215(76), 213 (100).

Part R. A solution of the bromide from Part E (923 mg, 4.33 mmol) in tetrahydrofuran (20 mL) was cooled to -78°C and treated with a hexane solution of p-butyllithium (3.0 mL, 1.6 M, 4.8 mmol). The reaction mixture was treated with triisopropylborate (1.00 ml, 4.33 mmol) for 1 hour and warmed to room temperature for 6 hours.

Then ml of 6M aqueous NSI and 3 ml of water were added, and the resulting mixture was stirred for 1 hour. Then it was poured into water (100 ml) and extracted with ethyl acetate (2 x 100 ml). The extracts were washed with brine (bOml), combined, dried over sodium sulfate, filtered and evaporated to give a solid, which was purified by trituration with hexane. 6b-methyl-2,3-dihydrobenzofuran-5-boronic acid (718 mg, 4.03 mmol. 9390) was obtained.

Part a. A mixture of boronic acid from Part E (298mg, 1.67mmol), b-chloro-9-dicyclopropylmethyl-8-ethylpurine (309mg, 1.12mmol), 2M aqueous sodium carbonate solution (1.7ml, 3.4mmol) and triphenylphosphine (bimg, 0.233 mmol) in UOME (20 mL) was degassed by repeated cycles of vacuum pumping and nitrogen flushing. Palladium (II) acetate (1 mg, 0.058 mmol) was then added to it, and the mixture was degassed again, and then heated with an inverted refrigerator for 14 hours. Then it was cooled and poured into water (100 ml). This mixture was extracted with ethyl acetate (2x100ml), and the extracts were washed successively with brine (bOml), combined, dried over sodium sulfate, filtered and evaporated.

The residual material was separated by column chromatography (silica gel, 20:80 ethyl acetate-hexane) to give the title product as a solid. Then this substance was recrystallized for purification from ether (253 mg, 0.77 mmol, 6995). Tal--147-148"S. TI C Ak 0.18 (30:70 ethyl acetate-hexane). "H NMR (300 MHz, SOCI3): a 8.88 (1Н, 5), 7.60 (1Н, 5), 6.77 (1H, 5), 4.61 (2H, i, U-8.6 Hu), 3.44 (IN, m Bi), 3.24 (2H, i, 9-86 Hu ), 2.94 (2H, Bi), 2.44 (ZN, 5), 2.03 (2H, m Bi), 1.45 (ZN, Bgi, 9-6 Hz), 0.89-0, 79 (2H, t), 0.58 (2H, Bi), 0.50-0.40 (2H, t), 0.27-0.17 (2H, t). Mass spectroscopy (MS-SI): t/e 377(4), 376(27), 375 (100).

Analysis, calculation. for SgzNoviMaO: C, 73.77; H, 7.01; M, 14.96; found: C, 73.69; N, 7.08; M, 14.40.

Examples 5201, 5231 and 5232

Preparation of 9-dicyclopropylmethyl-8-ethyl-6-(b-methylbenzofuran-5-yl)purine, 6-(2-bromo-6-methylbenzofuran-5-yl)-9U-dicyclopropylmethyl-8-ethylpurinutab-(7-bromo -6-methyl-2,3-dihydrobenzofuran-5-yl)y-Y-dicyclopropylmethyl-8-ethylpurine

A solution of the compound from Example 5001 (250 mg, 0.668 mmol) and M-bromosuccinimide (119 mg, 0.669 mmol) in 1,2-dichloroethane (100 mL) was heated with reflux for 12 hours, then cooled and evaporated. The resulting mixture was dissolved in ether, filtered and evaporated, and the residual material was separated by flash chromatography (silica gel, 20:80 ethyl acetate-hexane) to give, in sequence, the following three products: 6-(2-bromo-6-methylbenzofuran- 5-yl)-9N-dicyclopropylmethyl-8-ethylpurine: Tpl-: 177-178"0. TS A; 0.23 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOCIv): a 8, 92 (1H, 5), 7.85 (1H, 5), 7.42 (1H, 5), 6.74 (1H, 5), 4.15 (IN, m Bi), 2.97 (2H, m Bi), 2.54 (ZN, 5), 2.00 (2H, m Bi, 1.44 (ZN, Bgi, 9-7 Hz), 0.90-0.80 (2H, t), 0 .63-0.53 (2H, t), 0.50-0.40 (2H, t), 0.26-0.16 (2H, t). Mass spectroscopy (MHz-SI): t/e , calculated for CgzHg2"VIiMaO: 451.1133, found 451.1132; 455(3), 454(25), 453(99), 452(31), 451(100). 9-Dicyclopropylmethyl-8-ethyl- 6-(b-methylbenzofuran-5-yl)purine: Tal--139-1417C. TI C B; 0.16 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOCI3): a 8.92 (1H, 5), 7.95 (1H, 5), 7.60 (1H, y, 9-22 Gu), 7.48 (1H, a, 20-0.7 Hz), 6.78 (1H , aa, 0-22, 0.7 Hu), 4.40 (1H, m Bi), 2.97 (2H, m Bi), 2.56 (ZN, 5), 2.04 (2H, m Bi), 1.44 (ZN, bg and 9u-7 Hz), 0.90-0.80 (2H, t), 0.62-0.52 (2H, t), 0.51-0.41 (2H, t), 0.29-0.18 (2H, t). Mass spectroscopy (MH-SI): t/e, calc. for СгзНо5МаО: 373.2028, found 373.2033; 375(3), 374(26), 373(100). 6-(7-bromo-6-methyl-2,3-dihydrobenzofuran-5-yl)-N-dicyclopropylmethyl-8-ethylpurine: Tpl--179-1807C. 11 S

Be 0.04 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSI3): a 8.89 (1H, 5), 7.47 (1H, 5), 4.73 (2H, i, 9-8.6 Gu), 3.80 (IN . , 0.89-0.79 (2H, t), 0.61-0.52 (2H, t), 0.51-0.41 (2H, t), 0.28-0.18 (2H, Mass spectroscopy (MS-SI): t/e, calculated for SgzNovV/gMaO: 453.1290, found 453.1285; 455(98), 453(100).

TABLE 5 sion VIV , 15 va vi»- v»- i 3 M or M wai chu snz-X b snz-x-X snz- kn vi t B

KIZ vig2 Kk a. m A. z. - tu urugtlte (A (8) p

Y, inn pini pd id VN inv v ya As vi r nn in PN pd i in PN ii inv nni pp pov pan

M HO A a r s ke in Tpl., app. "с 5001 СН, Н сн, сн, сн. о с-с.и с-с,Нн, 147-145 0022 syn. х! СН, св, се. о E: | 4- (СН.О0) - B, t- 5003 сн, н сн, св, сн, 5 си, с-С,.Н, t 5004 СН, Н СН, сн, сн; and С.,Н. с -СОН, - 5005 сн, Is sn, Sy, SN, o s.,n, s -s.N. -

3944 SM, y osi sia, si, osi, sh-SUV5 - 5046 sn, bearers st sv, o sk. s-s,H, - 5046 sv, 8 s1 sn, sv in! Sena s-SN, - 5047 st. s.n, - 5aeu sia, NN si sia, sv, o s." sn, - zo5o sn, nn si sn, SV, Ha sn, sn, - 5051 sn nn s1- o sia; o s-s.n, s-s, - 5052 sn, Mn si o sn, He n 4-(sn5o)-SK, - 5053 s no o sy; o sn, s-SN, - 5054 sn, NN si o sn, o Siv» s-sW - 5055 sn, VN gs1 o sn. o sov, s-g, - 5056 sya, No si o sya, and sina s-s:N, - 5057 sya, B sF1 o sn, o SN SzN. . svbv sv, But si o sn, si s.v, -

Zo59 se, in "a o sn o sn, s, - both, mo si o sv, o sn, sv, - 50561 0 no si sn, sp, o s-sN, s-SN, - 5062 0 no sya . OO no sia, sv, s, Z san, se-SN, - 5055 o in sv sn, SV, o sen, s-buN, - 5057 o ko sia, sn, sn, ge sen, sn, -

Beans o No sn, syu sy, o san, save - 50690 no sn, sv, sv, o Sava SN - 5070 (o no sn, snu, sv, os sy, sov, - 50734 0 nN sv s sv. o s -С3в5 s-sV, - 5072 o N sv, o sna o n 4-(sn.0)-s,H, - 50739 nn s o sv, os sy, s-sN, - 5074 o NN st o sya, o Sava s-sN, - 5075 o ko sya, o sy, z sv, «-sya, - 5076 (o ns, o sn, o s.N, s-sZ, - 5077 0 no s, o sn, o son, s - 50780 i sv, 0 sv 0 sv, sin, - 5079 o nn st o NE, o siv, sn, - zo o v st o sy, o SN, s, - ovi o no si sk, sn, o с-с,Н, с-С38, -

5082 OO no si sv. sv, o n 4-(sn,01-sN, - 5083 o No s1 sn, sn, o sn, s-S.N, - 504 OO no si sp, sn, o son s-sy, - 5ono o n si sn. sn, o san, s-SNu - "he is wearing sia. sleep, o sn, s--s, - 5087 Do no si sn, sn, o San, syn, -

ZOV o No si sn, s, o SN san, - 5069 (o no si sk, sn, o sn, sn, - 5090 o n si st sn, o sn, suv, - 5o31 o si o sn, o s- o s-CH - 5992. 0 ns o sy, o i 4-(svo s, - 5093 0 nn sg o sy, o se s-S,H - 50940 n si o sn, o sa se-s,n, -

Because o no si o sn, o S.V, s-s,, - 5096 o n si o sv, o S.V, s-S,K, - 5097. o nn s1 o sn, o san. Sv, - 5038 o ns o sn, o sia, sn, - "093. 0 and si o sn, o sia, sv, - 51000 i si o sn. o sn, sv, - 5101 sn, sn, sya, st se, o s-sSa s-Skhn, - 5102 s, sya, sn, sn, SN, o n 4-(sto)-sS, - 5zioz sv, sya, sb sya, sn, o sn, s-sUNy 5104 sny, sn, SN, sya, sn, o siv, e-S.n, - 5105 sy, sn, SYA, s, s, Ge) sn, " -с, - 5196 сн, СМу sya, сн, св, о с.н, e-С3Н, - 107 сн, ся, сн, св, сн, о сн сн, - 2108 сн, ся, ся, сн, св . s,v, - 5111 sn, K s1 o s-0 kn s-s.uN, s-s,n, - n51i2 s, NN si 0 0szo VN Kk 4-(sto-s,n, - 51113 s, NN s) 0 (s-o Mk i: K e-SON, - zi14 syu NN О0ОсС1 00 00 sho Mk s, e-sSIN, - ti so VO 0ОС1 00:50 Mk sn, e-sV, - 5116 svo no s1 00 00s-o0 Mk s e-SN, - 5117 syu, nn si o s-o My san, SzN. - 5318 SE Kk s1 0 (sya nn sv sen. - zce s NO Os1 00 0 so My sn, sn , -

zi20 sn, N si o s-0 MN sn, sS.n, -

BI21 sn, zho si o Sto MON os-Cy, c-СН8, - 5122 S. no s1 00 00xyuo zhk B 4-(сН.Оо-с,Н, - 5121 сн, H si ob Схо Сн, сн, e -сУН, - 5124 сн, в си о с-о вен, san» с-сН, - 5125 С, НН си 0 svo kn, с.н, с-с,Н, - 5126 С, no si o se sv . st. sn, - zizoz sia, nn si o Sho mon, sn, s,n, .- 5131 s 8 s o se M se SN s-sy, - 5133 sn, NN s: 0 ssn, M n 4-Isn ,U0u-seN, - 5133 s. NN si 0 se, M sn, s-S,V, - 5134 si and si o sec, M S.V, s-sN, - 5135 SE, in si 0 ss, Kk sleep, s-b,N, - 5136 s no so ssv, M sv, s-Sun, - 5137 S No SI 0 sov, Kk Son. sn. -

B138 St. No si o ossn, M SIV, san, - 5139 s NN s1 o sen, n SV, Sn. - 3140 s no s1 00 o ssv M sun, sun. - 141 svo yo s1 00 000s5o zhu, p. s-s,y, - 5142 SE, nn si 0 syu z, H 4-1sn,01-s,n, - 5143 s, si a s-o ks. sy, s-sN, - 5144 sv, bear 00 000s-o kyu, szh, e-S,H, - 545 syu НО с1 0 sgo zh, su, ss, - 5146 С, НН si o so zh, sg. s-s,V, - 147 s, and SE 0 so kov, s, san, - 5148 s, NN si 0 syu zhd, s;v, syn, - 5149 s, NN s1 0 sao zhu, sv, s, - z150 s and s1 0 so zhu, sv, san, - 5151 s, I si 6 (5 o s-s,H, s-S,H, - 5152 s, Ж si 0 (s-o o n 4- (sno3-s,n, - 5153. S kN s1 0 so o sn, s-SkhN, - 5154 s, no s1 959 sfe o SU s-S.V, - 5155. SV. NN si o syu o sv, s-sy, - zi56 hundred i s1 000 s- o Sena s-sN, - 5157. s, NN si o sia o sv, sn, -

5i58 sn, But sI o Sa0 o Sn sin, - 5159. p. ( НнНс1 о со о с, Sn - 5166 sya, no s o seo о сн, sn. - "16th сн, NN с1 00 st o s-сН, с- SV, - 5162 SN, nn a o ss, о Kk 4a-(sno-s,V, - 5163 sn No cI1 o ss o sy. e-SN, - 51564 s, no si o sn, o sia s-sSin - 5165 SN, n si o sl, o SV. s -СН, 5Bi6ye syu, NN si 0 ss o Sava s-sW, - 51567 sn, NN SI o sv, 0 sv sn, - 5166 syu no s1 o sist 0 Son, san, - 5169 s, no s1 o snsn . .0О-с.Н, - 5173 св. - 5175 p., NN p. s, NN s, OO s-o o s,n, SON - 5180 sv, n sn, a se-b o sn, sp, - -shchai sia, mn sia, 0 ss, 0 s-OV, se-s , - 5182 st. - vin5 sn, NN Sv 0 sni b i: KSH s-s, - 5185 sya, NN s, 0 ssv, 0 sani e-sv, - h187 s NN st 0 sia, 0 sn, s zn, - 5188 s nn s, o ss o sSan p. 8, - 5189 sya, NN svv o s, 0 sn, sn, - 51390 sya, y s, 9 sn, 0 sn, sne - 5191 Sv no s1 o sneya, MY, s-S,ya, s-SN, - 5192 sya, NN si o snsya, Zh, n 4-i(sn,0)-sen, - 5193. SN, N si o snyn.

ЖН, сн, s-02Ж, - 5194 sya, mn si o sia,n, SN, sin, s-sn, - 5195 SV, NN SI o syasya, nen, sn, e-S, -

5iZzb sn, n "1 b sNnzhn, mn, San, "-SNa shchi 5197 sv, n si o sny, Ve, san, syn, - 5iza syu, M si 0 sn KSV, sn. sen, - 51939 sk, NN SI o sn,n,. MV, sun, sun, - 5200 sya, I si a snsn., sun, SNU san, - 5201 Sv, p sia, "sn sk a 2-s,N, e-s38, 133-141 5202 sv, I sv , s sn o H 4-(sn5o-s,n, - 5293 sv, ns s sn o sn, s-sN - 5294 sn, no sn, sn sia 9) Son, se-s,ya, - vB?O » sv, NN sun, sv sun o sen. s-ShN, - 5205 s NN s, sno sn o s.n, s-SzN, - swat sn, kos so sno o san, sne - 56202 sn. Kk sia, sia SN o sen, sna - 209 sn, From SN, sn si a San, s, - 5210 sn; V sya, sno sno o sno, sno, - 5211 syu nn si sia Osn o s: sv s-SN, - 5213 s, NN si sn si o n 4-(sn,oО1-СhН, - "211 sv VN si so osn o spa s-Sin, - 5214 syu, Ya si sn sia o sov, s-m, - 5215 sn Kk si sy sn 0 Sn» s-s,V, - 5215 SN; n s sy sn o s, n, «-S8, - 5217 sv, NN si sno sn Ge) sn. s, n, a

B21I6 sno no si sno sno sya, S.V, - 5219 sya, NN si s sno sno sno sn, sno, - -26 sno -оН, с-сН, - 5227 с, no са, сн сНоВ сн ВН 4-исн,0)-сН, - 223 сн, n са сно ссн ссн сн сн, с-СзН, - 5224 сн, НН св с со сно sn se, e-sV, - 5225 sv, NN sn, sNsNoOosn sne s-s,V, - 5226 sv, no sia, sno sNsn sN sn, s-g, - 5227 sn, nos o sno sNysn sN s. Sleep - 5228 sp. no sn, sno sne sia S.Y, s - 52293 SV. n sia, sn o sn sn sn, s.n, - 5230 p. no sya, sya sne sy sya, syn, - 5231 SYA, N sv, sn Ssve v) s-eN, ss. 177-178 x 5232 sya, NN sya, s, sv, o e-s, 8, s-s, 179-160 5233 sv, NN st, sno sec, and s-OV, s-sN, - 5234 sp, NN art. sn, o e-szn, s-s,n, - t nn nin viny ZP pp p pn p mon non ntnrnpntitnn

TABLE FOR

K1B 5 that v1a-4 k1a- k1a- ik t y Ku'ki snz-h-u | snz-x-zh | snz-x-x ov and kita si sn siz

K12 812 в" щ vi? в" шк He schy vro ros Ne (A) (vi (si and inal yani lk. JAN. ZNO o s no nn

Mkh t a s Kk" I: Tpl., app. "s ni nin o p ko o DL ni Op po p nni 5212 sn, VE sn, se, a s-s,n, s-s,N, 179-180 5234 St., Si Sn. sy, o s-S,N, s-s.N, and 5236 sn; СЙ, сн, сн, о ес, с-Са3Н5 t

К.

The methods used to prepare the compounds of Table 1 can be applied to the synthesis of the compounds

Structures A in Table 6. For example, replacement of benzeneboronic acids in a palladium-catalyzed aryl crosslinking (see Examples 35 or 831) with variously substituted pentaatomic heteroarylboronic acids will give the desired b-heteroarylpurine compounds.

The methods shown in Schemes 13 and 14 can be used to prepare many of the compounds of example Structures B and C in Table 6 with minor procedural modifications where necessary and using reagents of acceptable structure.

TABLE 6 viv shR viv vat tiv - va- ,

M y I Myh v M y: sna - yo svz - AY sn o - p hu y y ve ; y Kn y SHHI res her- r- o

AS (B) (c)

M hv a v s a ve di" Tpl., app. zach soi sy, nn ss, M 2 ss, se-svn, e-S,H, oil 6002 sy, M ss, M o ssn, sv, s-SN i 5003 sn. nn ss, ch o ss, szh, 2-8, - 6o04 sn, M ss, "m o ssn, s, se-SN, - vap5 sya, Kk sesn, B Ge sen, sk, s-sK, - va06 sun, NN ss, K o ss, sv, Sun, - 600? s, nn ss, M o ss, s, s, - 6008 si, i ss m o ssya, sv, sia - 6va05 sn. nn ss "M o ss siv, siv, - 6010 sya, NN ss, M o ss, no 4-C0-S, 0 - 6011 on sn, M o ssn, s-s, s-EzN" - b6o17 o nn sst in o ss .

6014 o no sov Mo 00 00 ssn, sa, s-SW - 5015 a v es M o ss siv, s-sW, - 5016 on ss. At 00 ss 0 s san; - 6017 hours ss, M oo ss, sv, sun, - bo18 to h ss mo 0000 ssn, CH sv, - 019 ssv M o ss s S.V, - 6020 ss M o ssv, N i-sto- s;e, - 60314 sn, sn, ss MO 000000 SSN, s-Su; 00 e-S - 6022 sv, sv asn, M 0 ss, s s-san, - base3 sya, sya, sov, M 00 ssn, SV, s-S, - 6024 sn, sya, ss M o ssn,. с, с-СаВ, - в025 сн, ся, сс, Mо соб, с, с-С,й, - 6026 сн, ся, сс, Моес, сн, SA; - - vases? sn, sv, ss, M 000 00 ss, ss sn, - voza sv, SYA, ss, M o ssn, sn, ss, - 6029 sn, sn, ss, B 0 ss st san, - 6030 sn, su, sov, M 09 0 ss, No y-snyu-evo 0 6031 sn, NN ss, MO VSN, eSN, ss s-oV, - 6032 sn. 8 ssN, M ssN, ss s, s-sN, - 6033 sn, M ss, VO ssSn, SSN, Sat, s-syn, - 6034 sn, NN osn, mmM all, ssn, SN, s-sUV, - 6035 сн, нн сс, М MсЙ, сс, с, e-СН, -

BoOzie sya, I bsn, M Sun, ssya, sv SVI - 6037 sn, NN ssn, M SN, Osn, s, sne - 5038 sn, y sen, M Sya, sov so, son, - 6039 sn, nn ss, M Mon. sst s, sn - vogo sn, nn ssya, M vs, ss, N a-snuesIo- 6041 o nn son, mmM mn, ssn, s-S, s-SzNu - vov2 on ss, m o yysn, ssN, sn . , s-sy, - 6o46 o in ss, M sn, sn, SE, s. - 6047 on sen, m ven, ssn, szh san. - voch8 ok ss, m ns, ss, s, Sv, - 6049 o nn sen, mo sv ss, s, sav, - 6o5O o no ssv mo sya, es, NN 0 4-svo-sSy, - 6vov1 sn, SN, ss, M ven, bSY 2-8. 0s-o -

6o52 sn, sc, dream. Mo vs, ss, sn, s-sazn, - 6055 sk, sya ss, Mo MeK, ssn, sv, s-sSUy - vovi sn. sia, EU mo as. ss c, c-C, H, -

BOB sn, sya, ssv, Mo VsN, ss, s, e-sUn, 4

Vova sn, sya, esM,. zmZh sun, sun, sun, s - 6057 sun, sk, ss. M ms, ssya, sv, sn, -

BEANS si, sya, ss mo Men, ss, sya, sn, - 6059 sn, sya, ss, M Zhsn, es, s, sev, - 6vabo sya, sn. сСН, и шн, ссн, Н 4-сн10-С,Н, - 6о61 сн, нн сс, M си СС, se-s,n, с-SUN, - 6062 sya, I ссн, M Ksn сснУ св, а - Sun, -

BOB sia, nn ss, M MsS,n, SS. Sat, s-Sya, -

BoBE sn, nn sen, M MS,ya. SSSK, sb, s-s, - 6055 sn. nn ssn, km mya, ss, .s.V, s-S.N, - 5066 sn. nn ss, M MSn, ss, sk, snu - bob sya, nn ssya, mm mmszh, ssN, sv, SN - 5058 sn, nn sosyu, Mo sut ssN, sv, syn, - 5069 sya, No sen, M ms , SS SN, SA - 6070 SN. nn ss, mm mmm,n, SS, H 4-sSo-sS, -- vo71 o No son, MB o MS SsSNI se-sui, s-s,n, - 6072 o no sec, M MS. ss, sk, s-s,n, - 6073 o i ss, m Zhzh,n, se. sn se-s3H, - 6074 on ss, Mo ms ss, sn, s-s,, - 6075 (v; n ss, Mo acon. ss. cm, e-S3Ne - bota o no osn, m ys,ya, sen, sy, SV, - 6077 o n ss, m ms, ss s, SN, - bot o no osn, M vs, ss, su, siy, - 679 0 no os, mo mya, ssn, s, san, - bovo o no ss, mm vs,, ss, 8 4-СН,0-С, Ж -- vovi сн, св, ссЕ, M Сн, сс, se-С, с-с,, -

BoV sya, sya, sosya, M vs, sen, SV, s-s,N, - 683 sn. sya, ssya, M Ks, ss, sv, s-SN, - bov84 sn, st, ss, M all, ss V, s-SN, - b6oa5 sn, sya, ssSn; Mo Sen. ssya, SV, s-sN, - bove sn. sv, ss, nn Si SsNU SV, SUNe -

FOR? sny, sya, ssyaya, mm zhi ss. sya sn, - voya8 sn, sya, ssn, M MS, ssV. B, sov, - 5039 sia. svv ss mo ms. ssn, s san, -

6090 bedrooms sn, сSN, M non, СSN, H a-svossg 091 с, no ссЯ, MO sen, OMSN, sosuv 0 ЕЗОН; Y 6052 sya, M ssSfU Mo ss MSN, SV son, and boz3 00sn, BUT ssn, y sSsn, oMSnU Sai, seba i voza sn, Mo sen, mo ss, VK, s, 2nd, - voze sn, m ssya, M ss, MN, sya, s-SN. - 6096 st, n ssn, M sen, SN, SE, sn, - 607 sv, y ss, m ssn, MsV, y, suk, - epoya sn, NN ssn, M ss, VN, S, SV, -

God, nos, M sov Sat, St, Sen, - 6100 Sn, nn ss, m ss. yKN, y 0 4-svyuo-S,, /- 6101 sn, h sov Mo VSYv OSSN, s-sZh, s-sSZh, - 8102 sya. no ss, M o vSen, ssN, SV, s-SUn, - 6103 sn, V ss M o mun, ssya, s, s-sin, . 6104 stv no sen, km to her, sov s, s-сON, - 6105, sn, NN esya, Mo ms, ss, sya, s-SV, - v106 sya, n ss, mm ks, ssn, SV, sn, , 6vi0t7 sn, NN ss, mm nan, s ssh siv, - v108 s. no ss, Mo zZs,y ssya, s, sn, - 6109 sv, nN ss, m Zho,, sn, SV, San, - 6110 sn, m ss, M Zov, ss, in 4-sto-Si, - 6111 o no sen, mo all, SSN s-s 00 ss, - 6112 o no os, mm vs, ssya, SE s-sUN, - 6113 o no ss, mo ns, se, sЖzh s-saN, I 5114 on ss, mm in ss, s, s-SN, - 5115. DD(( p n ss, m mzhshsh ssya, sv, s-S,N, - 5116 on ss, M kun, sen, sn, s - 5117 o no ss, M all, ss, SYA, . s, - 6118 on ss, m sv, ss, s, szna - 6119 o no ss, no vs, os, st. sen, - 6129 o no ss, mo Mme,, ss, NN 4-svo-sn, - 6121 syu, sya, ssYa, M vsY, SSN, s-sZh, 00 e-s - 6123 sn, sn, sSK, M ss, ss, SV, s-sN, - 6133 sn, st, ss, m Mseav osv, s, s-SUN, - 6124 sk, sn, SYA, mm zhn, ss, s, s-S - 6125 sv, sv, ssya, M zhЖ,n, ss, st «- San, - 6126 sm, sya, ss Mo ns, SYA, sn, sne - 6i27 sm, sna, ss, M vs ssya, s, sn" .

65128 SN, SN sen. M ra sen, su, s.n,., shchi 6129 sn. SNI sen, M k.n., sen, San, S.Ne t 5130 p. SN, sen, M m,V, sen, nn 4-sn,-s,n, -

I pop pat day o o foam op pan vn vv v VV OK

Key: a) For the compounds marked as "oil", the spectral data are given below: Example 6001, spectral data:

Mass spectroscopy (MS-SI): m/e 338 (MN, 10095).

The methods used to prepare the compounds of Table 1 can be applied to the synthesis of the compounds

Structures A in Table 7. Preparation of those compounds obtained by cycloaddition of compounds with alkynyl-bearing B! groups, is illustrated by the following examples.

The methods outlined in Schemes 13 and 14 can be used to prepare many of the example compounds of Structures B and C in Table 7 with minor procedural modifications where necessary and using reagents of acceptable structure.

Example 7409

Preparation of 9-|1-cyclopropyl-1-(3-methyl-isoxazol-5-yl)umethyl|)|-6-(2,4-dichlorophenyl)-8-ethyl-UN-purine

To a stirred solution of the compound from Example 7241 (90 mg, 0.24 mmol) prepared in a manner similar to that of Example 2 using 6-(2,4-dichlorophenyl)-8-ethyl-9H- purine and 3-cyclopropyl-1-propyn-3-ol) in methylene chloride (2 ml) was added chloroacetaldoxime (25 mg, 0.27 mmol) and triethylamine (0.038 ml, 0.27 mmol). (The chloroacetaldoxime used was previously prepared by reacting equimolar amounts of acetaldoxime and M-chlorosuccinimide in UOME, followed by extraction of the product with diethyl ether and washing with water.) The cycloaddition reaction was monitored by TIS (thin-layer chromatography), and chloroacetaldoxime and triethylamine were added in addition until not all of the source material was absorbed. The reaction mixture was purified by direct injection into a column packed with silica gel and eluted using a gradient of 10090 hexane to 2590 ethyl acetate in hexane. 72 mg of white foam was collected. Mass spectroscopy (MH3-SI) 428 (Manu. NAM5 (High-resolution mass spectroscopy): m/e-428.1037 (Mane, C21NhoSi2M5O). Purity 29795 (reverse-phase high-performance liquid chromatography).

Examples 7396 and 7398

Preparation of 6-(2,4-dichlorophenyl)-9-(11-(3-ethoxycarbonyl-isoxazol-5-yl)butyl|-8-ethyl-9H purine and 9-H1-(4-cyano-3-ethoxycarbonyl- isoxazol-5-yl)butyl|-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine

A solution of the compound from Example 7259 (120 mg, 0.321 mmol), which was prepared in a manner similar to that of Example 2, using 6-(2,4-dichlorophenyl)-8-ethyl-9UN-purine and 1-hexyne-3- ol), ethyl chlorooxymidoacetate (146 mg, 0.963 mmol) and diisopropylethylamine (170 μl, 0.976 mmol) in toluene (2 ml) was heated with an inverted refrigerator for 20 hours, then cooled and diluted with 20 ml of ethyl acetate. Then the mixture was washed with water (2x20ml) and saturated aqueous brine (20ml), and the aqueous phases were successively back-extracted with ethyl acetate (20ml). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and evaporated. The residual material was separated by column chromatography (silica gel, 1:4 ethyl acetate-hexane) to give, sequentially, unreacted starting material (approximately 500 mg), then the compound from Example 7396 (58.7 mg, 0.120 mmol, 37905) and finally , compounds from Example 7398 (23.8 mg, 0.046 mmol, 1495); the last two compounds in the form of solid amorphous substances.

Example 7396, spectral data: TI C V; 0.27 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz"): b 8.96 (IN, 5), 7.67 (1H, a, 9-81 Hz), 7.58 (1H, a, 91.8 Hz), 7 .41 (1H, aa, 9-81, 1.8 Hu), 6.86 (1H, 5), 5.83 (1H, aa, -9.9, 6.2 Hu), 4.43 (2H , a, 9U-7.3 Hz), 2.98 (2H, a, 97.7 Hz), 2.91-2.78 (IN, t), 2.63-2.49 (1H, t) , 1.42 (ZN, ii, 9-7.7 Hu), 1.40 (ZN, 6 9U-7.3 Hu), 1.39-1.19 (2H, t), 1.00 , i, 9uU-7.3 Hz).Mass spectroscopy (MHz-SI): t/e, calculated for

SgziNgaS2M5O: 488.1256, found 488.1252; 493(3), 492(13), 491(18), 490(68), 489(28), 488(100).

Example 7398, spectral data: TI C V; 0.11 (20:80 ethyl acetate-hexane). "H NMR (300 MHz, SOSIz): b 8.99 (IN, 5), 7.72 (1H, a, 9-81 Hz), 7.59 (IN, a, 9-1.8 Hz), 7.42 (1H, ai, 0-81, 1.8 Hz), 5.40 (1H, ad, 9-10.4, 5.0 Hu), 4.42 (2H, a, 9-74 Hu ), 3.00-2.90 (2H, t), 2.66-2.52 (1H, t), 2.51-2.38 (1H, t), 1.46 (ZN, I, 9 -74 Hz), 1.41 (ZN, i,

ЧУ7, З Hz), 1.40-1.10 (2Н, t), 0.98 (ЗН, и, 9-7.2 Hz). Mass spectroscopy (MH-SI): t/e, calc. for SgaNo5Si2MvOl: 531.1315, found 531.1315; 531(100).

TABLE 7 o M, visa 9 s M

M y: "M y M still sleep -x SNa-x SNI -y I osyu-nn i-y

M M Ii ko vi de ki po v vi vi vi vi

Vo to I (A) (8) (C)

IR app. x in v kiz vi di" I. s i Tpl., z v zo sn. s, sn, n se, sia, zvyaok sa1 - 7002 ska sk, SV, N sv, s, zvyaZOK 51 - 7001 sia. sn, sv, H sy, sn, connection (1 - 7004 sn, sya, sn, H sya, s-S,ya, connection 01 - 7005 sn, sn. sn, V sv, sy, connection p t 7006 sn, sya, s, n sy, ban connection ai - 7007 sya, sya, sv, n sya, SN, connection (2 - tosya sna s, sya, n sn, s-s,n., CONNECTION b2 - 7099 s. sv, sya, i sv sy, connection OZ - x 7010 sn, st, sn, n sn, sn, zVYaZoK 3 - 7011 sn, sn, sv, i sy, S,N, zBYAZOK OZ -

7912 sn, sy, sk, n sn, e-sn. connection 3 sk 7013 sv, sia, sn, nn sn sn, sn, s - 7014 sk, sya, sn, sn sn, s, sn. s - 1015 sc, sn, sn, n sn, s, sna sa - 7016 sn; sun, sun, H SN, e-S,i, sun, 4 - 7017 sun. St., Sun. st SV, n sv, sun, sun, 65 - 7019 sun, sia, sun, n sun, S.Ya, son, s - 7020 sun, sun, sia, V s, s-Szh, sun, 05 - 7021 sk . sv, sn, in sn, syaz Connection o6 - 7022 sn, s, sv, no sn, s.n.

Connection o - 7023 st, sun, sun, n sy, sun, Connection se - 7024 sun, sv sv, n sn, s-S,, CONNECTION 65 - to25 sia, sia, sia, NN SV, Susn ZV'YAUK c7 - 7026 sya, sna, sna, n sna, sya, communication sya - 7027 sna. sn, sn, H sn, s, sn, vi - 7028 sn. sun, sun, n sun, s, sia, si - 1029 sk, sia sv, n sv sun, Sya, sa - 7030 sn, sv sia, no si sv, sna, s - 7031 sv, r1 si NI) n SN , connection (1 - 7032 sn, si si TSI |: San, connection 1 - 7033 sn, s1 si and H SN, connection C1 - 7034 sya. d1 s1 n Kk s-s,n, connection b1 - 7o35 sy, s si k In SN connection 2 - 7036 sy si s1 Kk N Si, connection 62 - 7037 sn, cha n N SUB, connection 22 - thesis sv, si s1 N n s-s, n, connection 2 - 7039 sn.

Connection 3 - 7041 sna si si Н n sС,. zVYAZOK s - 7047 sn, si s1 n E se-O,H, connection s3 - 7043 sya, s si n n si, sv, «s - 7044 sna si si E N sn СНе 4 - 7945 st, s1 si Н N St. Xia. o - 7045 pm (1 si n n s-bV, sn, 64 - 7047 s, s1 si N Kk sv, sk, a5 - tv se, si si n son, sn, 85 - 7049 sn, si s1 n Kk s,n, sia , co -

7050 sn, gi si N H s-s,N, sn, s5 - 7051 sn. sg s1 N V sn, communication about - 7052 sya. si si N n Son. connection sb - 7o53 sya, («s si i n Sak. connection ov - 7954 sv, si s n V s-s,, connection ov - 7055 sna, si si n N SNizhSNoO connection 07 - 70558 si. s1 si n n SN, connection p8 - 7057 sn. si s nn n sn, sn. 52 - 7061 sy; sn, osN, n n NE connection bi - 7062 sn. sn, Os, and n SN connection p1 - 7063 sn. connection di - 7064 se, sya, osk, N E s-s,n, connection s1 - 7065 sn. sa - 7067 sn. sya; sya, osn, V n San connection 3 - to7i sna Sn osn, NN p Sub, connection 3 x 72 sn, sna, osn, 5 n 2-SN. connection 3 - 7973 sn, sya, osn, "M n NE, SN, SI - 7a74 SN, SN, SUN, NN Н san, SN, Са - 7075 svv sv east, V n SUK p. 64 - 7076 SN, SN os, H se-sV, SN, bi - 7077 sn, sn, osn, NN n sn, sn. 5 - taya sy. sya, sya, n n SN sn. 65 - tota sy, sya, osn, Б N sn, "sn.

ОЗ - 7ovo сн сн, осв, in H с-с,Н, сн, 5 - т7ов1 сн, сн, св, Кк Н сн, connection св - 7ав2 сн, ся, се, Е n СН, connection ob - toyaz сн , "NN, OSN, | N SE, connection 06 - 7084 sya, "n, osYa, n E se-s.n, connection ab - 7r85 sy, sn, axis, NN n ss connection 7 - 7086 sn. sya, sya, n y sya, the connection of sv naslo 7087 sn. sleep, sleep, sleep, sleep, s1 -

tova si, SYA, os, Mn n sn, si, sv1 - 7tovo sia, syu osv, (VN n Sn syu ba 00 - 7090 sk, sni, osn, in Kk s.n, sni seg - 79981 sni, si osn , n K SN, connection b1 - 7092 sv, si sy, N n son. connection F1 schi 7093 sn, s1 sk, n g! Sy, connection sa1 - 7094 sy, s1 osn, n in se-SN,. connection si - 7095 sy, sg: osn, n n sya. bundle s2 - 7096 syu, Si osya, kn n sya; connection s2 - 70937 sn, si osn, N n s, connection s2 - 7098 sn, s sia, ri N s-sSu, connection 52 - 7059 sn. "1 os, N n SN, svchYaZOK s - 7100 sn si Fon, n n San; connection p - 7101 sn. si sn, n N Syn, connection 3 - 7102 Sn. si osn, MN in s-S,H, connection 93 - 7103 sn, si osya, NN n sn, sy, va - 71601 sna si OsE, nn n s. sn, s - 7105 sn, s os, B N sn, sya, (4 - t1i06 SN, SI ost, N n s-sN, st. 4 - 7107 sn, s osn, nn n sy, sv, 95 - lv sk. si os, nn n sanu sk; o5 - 7109 sv. osn, N N Sa connection ob - 7113 sy, si osn, nn Sub connection 6 - 7114 sn si osn, n n sebab, CONNECTION 6 - 7115 s on si osf, nn NN Sn.esSN about connection 7 - 7115 sy, s1 AXIS, n NN SV, connection Ov maslo 7117 sny, si os NN N SN, sno FI - tiv sn, si osYaya, V n sv, syu, a - 7119 si, s1 os, NN K siv, sn, F - 7120 sn, su os, NN Kk sen, sk, 62 - 7121 sv, si skh, n n si, connection si - 7122 sn, si SE , n N S.N. connection 9 - 7123 p. si sv, n n sk. bond 61 - 7124 sn, c1 CE, H n c-С3Н, bond 61 - 7125 sn. si sk, n n SN. communication C7 -

7126 s, syu VN n San, communication with? 7 727 Sn Si Sv, Ii n Sun. connection b2 - tn sv, si st 0 VN H s-C,H, connection 2 - 7129 sk, si sv, Н H sn, connection 93 - 7130 sn, so sv; NN n S.n, connection at c3 - 7131 sn. si sv, nn n Sun: 0 connection 3 - 7132 sn, so sv n n s-Sun, connection 53 - 7133 sia, si sv, N n sv, sn, y - 7134 sn. s1 sv, N N son, SN, 64 - 7135 sn. si se, n N sa. dream o - tizv sia, si sv, nn s-on, s 004 - 7137 sn, si se, Н N sn, sn, 05 - 7izv sn, si sv, nn n sn, sn; 65 - 7139 st. si sv n n sn, sia, 95 - 7150 snu si SE, n N e-s,n, sv, s - 1141 sy. (ov! St, N N sk, connection sb - 7142 sy, si sk, n NI S,N. connection OB - 7143 sia, si SE, n n s,nN,. connection Ob - 7144 SN. p1 7 se, n n s-S,.v, bond p6 - 7145 sna si St, n H CH.-SN bond a7 - 7145 sn si SE, Н n sn, bond 8 oil 7147 sn si sv n K san, s. si - 7148 sv, si st, n n sv, sn, vi - 7149 sna s1 SE, n n sin, sn, s: - 7150 sn. s1 se, n Kk sk. sn. 82 - t7i5i s , SE, C1 ): n sn, connection s1 - 7152 sya, SE, s1 n n Sn, connection si - 7153 SNU sv, si n Kk sS.. CONNECTION s - 7154 s stv si n No os-sun, ZBYAYUK (c - 7155 sleep.

SE, c1 n n sv, connection c2 - 7156 sn, St, si n N S.Yah connection s - 7157 si sv, si N N SN, connection s - tiv sia, sE, sig n s-S, H, link 02 - 7158 CH, CE, si n n CH, zBYAZOKYU c3 - 716th CH, CE, (1 H n SN

Connection 03 - tib1 snu Sk, s n n San, connection with - 7162 sn.

CE, (c1 n n c-C,H connection 3 - 7163 Xia; CE, c1 N In sn; sn, 4 -

71654 sm, SE; si n n sn sn, bv4 - 7165 s, sv, si i and sv ost Fm4o00- 7156 Sn. st si N n s-SNU p. fri - 7167 sno St.

SE, si n I: sn. sya, 05 - th sun, SE, si n n sun, sch, 5 - 7170 sun. sv, si Н n 2-СН, СН, 05 - 7171 sv, sv, s n and sy, bond o6 - 7172 sn, sia, s1 n n b.N. contact 06 - 7173 snu sv, si n n SN. connection be - 7174 Snu sv, SI n n s-s,n, Connection 06 - 7175 SN, SE, si n n SNivSN CONNECTION 7 - titv sn, sv, si n Nn SN, connection SV - 7177 si, SE, si N N s, sia, 51 - 7178 Xia, Xia, si N n i: sn, 61 - tit5 Sn, SE, si I E San sn. (2 - 7180 SN.

Wed, Sat, Sat, Sat, Sun 62 - 7185 Sat, Sat, Sun, Sat, Sun Contact - tiv2 Sat, Sat, Sat, Sat, Sun, NN Sun, communication 01 - 7i18z Sun.

Sn, osn, SV, n szn, connection 61 - ti sya, sn, osn, sn, n ss, connection 01 - 7185 sn, sya, osn, sn and sn, connection 02 - 7186 sn. sy, asn, sn, Kk SU communication 98 - 7187 sn. sia, axes, sn, n SU, connection so - 7188 sn. sun, Sun, sun, sun, sun, sun, CONNECTION 42 - 7189 sun. sn, osn, sn, n sn, connection aZ - 71990. sn, s ost sn, Kk Son, ZB'K 3 - 7191 sn. sy, OosYaya, sn, n С,n, CONNECTION o3 - 7192 sya, sn, osn, sn, n e-S,H, connection OZ - 7193 sya, sya, osn, se, n SN, sn, 4 - tiza sn, sv osn, sv NK sanu sniv s - 7195 sny, sn, Oosp, SV, B sn, sn, - 7195 sya, sk, osn, se, Kk s-s, sn, a - 7197 sy, sn, osn , sm, kn sm, sm, p5 - 7198 sm. sk, osE, sn, n sn sleep e5 - 7199 sy, sy, osn, sia, n sv, sy, "5 - 7200 sn, se, osv, SY, and s-SN, sia, 05 - 7201 s, sv , os, su, K sn, connection sb -

7202 si; sn, Os8, sv, (g sin, connection 96 - 7253 sn. sk, Osn, sv, N San. connection 6 - 7204 sn. sia, osn, sn, ni s-s,y, Connection 66 - 7705 sun, si, sun, sun, r sne-sun Connection st - 1226 syu sia, sun, sun, I SYA, connection 8 - 7297 sia, sia, sun, sv, n sun sun, in - 7208 sun, sn, Osn, sn, n si, sn. c1 - 7209 sya, sna, oS sn, n son. sn, a? - 7210 sya, sya, os, sn, " sn, sy. 62

7211 o s1 se, N n San s, - 7212 o si se, n E s, so si - 7213 o « SE, Kk n SN, zVyaaZhMU s - 7215 o s Xia, n N SI, ZvyaK b - 7215 o b sv, n K s.n, sn, sa - 7216 sya SE se, N NK sn, s si - 7217 sv s sv, n H sn. s, a - 7218 syu, si sv, Kk n SIN, connection 2

2219 svv si sk I: n SN. link 02 - 7220 syu si st, N n SON, p. a - 7221 o st, «1 N CI sn, sn, «i - 7222 o st, si V n SN, sv vi - 7223 v! SE, si n n SU. connection 62 - 7224 a st, si n N San, connection 02 - 1225 v St, g n n sov, sv, sa - 72256 sv, SE, s1 N V son, sn. a - 7227 sn, sk, s n I: sn, sv ti - 7225 sn.

SE; si n H Sn, zvayuk si - 7229 sn, SE, 1 N g! dream

Connection p - 1230 sv, sk, si n n sn, p. in - 7231 sia. st, sv, n SE, SON, sno az oil 7233 sn, si si v i s-S,H, connection o - 7233 Ge: si s i n s-S,, connection 9 - tazi se si1 s k « n s-S,, connection 49 maslo 7235 o si st, Kk o 0os-s, ZVYAZOK dZ - 7236 sv, si ost NN N s-sSun, Communication s - 72371 Sn. sK;oosk, Kk N s-Sin. bond c9 - 7236 sn, sy, axis, c1 n c-SuH, bond 9 - 7239 se, si c GE sn, c-S,n,. connection with her

7240 sia, se; OS Ya n s-Sun. communication 09 - 7241 sn, Goi si n v s-Ss,; connection c10 oil 72412 Ge; s1 g n H e-SUN, connection sii - 7243 Xia si SE, I N s-S,8, connection s10 oil 7245 (c) s1 SE, V n s-S,, connection 010 - 7245 sya, s1 SN, G.

N s-S.K. communication 00 - 7245 p. si t nn Kk e-Si, connection 51j - 7247 sya, sp osn, si n s-S,H, connection 010 - 7248 sn, s si Н sn, s-sb, connection s10 - 7249 sk, sv, os B in s-s,n, connection 519 oil 17250 si, «a s1 N B S.n, connection 10 oil 7251 o si si n n s.n. communication 610 - 7252 Sk; (si SE, n n s.B, communication 010 9-99 7253 o si sv, n n Syn. communication bij - 7254 sn, si sn, NN n su, znyayukK sib - 7255 sn, si osE, NV n s,n, connection 010 - ta556 sn, sn, osn, si n sia, connection 610 - 7257 sn. si si n sn, Dream, Connection si - 7258 sn.

NN N s.K, connection 010 - 7259 sn, si si n Н sn, connection 610 Oil 7259 o SI s1 n n s,k, Connection s10 - 7251 sya. s1 SE, K N s.n, connection 010 oil 7252 in si SE, n n S, connection s10 - 7263 sya. si os NN N SC, connection c10 - 7254 sn, c1 osk, Н N su. connection c10 - 7265 sy, sn, Osn, SI N Sun, connection 6010 - 7266 sy. s1 si n son, SU. connection 910 oil 1267 sk, SE, osn, n H Сs,, connection 010 - t258 sya, Si si n n SN; communication 010 oil 7269 o si s1 nn n T. Nuy LINK 910 - 7220 sya, s1 se, n N SK; connection 010 oil 7271 o s1 SE, N N S.nNy connection 910 - 7272 sv, s OSV, NN N Sny connection 610 - 7273 sn: C1 osE, n n sny connection "10 - 7274 sya; sia, os, si N S.Ny connection 910 - 1275 sn. si SI n sia, S.Ny communication 014 - 7276 se, sk, Osn, nn n SzN.; contact 010 - 73977 sv s1 si n e sn, mon, sab -

7278 o si si I n sn, sn. a10 - 7273 sleep s; SE.

N n sn, sya, sow oil 7280 (v. si sv, n I: snu sn, 610 - tavi sv si os, Vn sya, SN. bio - 7282 s; si ost, I VN sya, sv 010 - 72283 sya, sya, SV, "1 n syn, sn. s1o - ta st o s: sI N se, sya, sya, aFaib - 7285 sya, sk, Osn, kn n sn, sn, (Fo - 7285 sn, si with her B s-CH connection tI1 oil 7287 o Fi si V n s-b,n, connection s11 - 7288 sn "FI SE, N n s-SuUn. connection F11 oil 7289 o se SE, n n s-S, NE connection 011 - 7239 sk1 osn, Н N s-S,N.

Connection F11 - 7291 sn, c1 axis, n H c-C,N. connection c11 - 7292 sn, sn, Osn, si n s-sS,N. connection a11 - 7293 sy, si si H SN, e-SUN, Connection s11 - 7294 sy, SE, Osn, H IN s-siIn, connection 011 - 7295 sn, si si H n s,.n. connection 11 oil 7296 a si si N n Sen. bundle 11 - 7297 sn. si CE, n n SinN, connection Phi oil 7298 o si SE, n n San, connection 011 - 77299 sn. si osn, Ya n s,.n, zVYAZK 011 - 7300 sn, SRO Ose, N K s,n. CONTACT 011 - 7391 sn. si, osSya, si n s, connection 11 - 7302 sv, si si In sv, SA, connection C11 - 7303 sn, SE, Osn, 2! n S,n, connection s11 - 171304 sya, si s Kn n Sun, connection sii 88-89 7305 o s si k n sn, svYAZK s11 - 1306 sn, si SE, n n S,nU connection 011 Oil 7307 o si SE, n Kn su, connection 11 - 7308 sia, si sv, Kk n S,n, connection 011 - 7:09 sun, si OSE, Kk n Sun, connection sii: 7310 sv, si, os si NN dream, Communication 911 - 7311 sn; si si V si, SU, communication p11 - 7312 sia, s, sv BK Nn SU. connection 11 - 7313 sia, si si Kk n S,N. contact b11 156-157 7314 o si si KE n sen. communication 011 - 7315 Sv; si SR, I n sS.n. connection with 1st 150-151

7316 0 SI SE, n N S.Ya, communication сI1 - 7317 sn. s1 osn, n Kk S,N.

Communication c11 - 7318 SN; s1 osv, NK n S«N.

By connection (11 - 7319 St. SN, OSN, SI n.

SE, education, n N S.A.

Connection sii - 7322 s, si si n n SN, Connection sp12 - 7323 o si si n n SN, connection 17 - 7324 sn, si SE, n NN Son, connection 012 maslo 7325 v! si se, n n SUK binds b12 - 7326 s, si os, no.

Song, connection pi: - 7327 sm; s1 education, Nn N Son. what are you talking about? - 7328 Xia, sn, os, (si n Song, connection 12 - 7129 sn. s si N sn, San, zZvyayuk syz - 7339 si; SE, osK, n n Sai; connection o 0212 - 7331 sn. si si N N Sat, B, connection 012 - 7332 o si s1 n n Sun, connection s12 - 2333 sn, si sv, n n Sun, Connection 0127 i 1334 s si sv, n n NzN connection p17 - 7315 sna "1 ost nn K SaK, connection 517 - 7335 sna.

Si os, n n S, 8, contact number 912 - 7317 Sk; sE, sya, si n SN, communication s12 - 7318 sya, si s1 In CH, SN, zvLZOK 612 - 7339 sni SE, os, Kn n Sun, Communication 012 - 7340. si, si (si Н n 2- С,Н, CONNECTION s12 - 7341 o s1 si N Kk s-С,, Connection Ф12 - 7342 sn. 1 SE, Н n s-С,Н, Connection 617 128-130 73az o s1 St, Н N s -SiH, CONNECTION 012 - 7344 sn. si osn, Н H s-С,Н., Connection 9212 - 7345 sn, с1 se, Н Н s-С,Н, connection (012 - 7346 sn. . 012 - 7349 sn. si sv, n n s-SUN, connection bI3 oil 7350. sn, si si n ya s-SuN, connection s13 - 7351 sn. si SE, n N s-S,N. connection ts oil 7352 sn.

7354 sn, sk s1 H n sn, CONNECTION 07 - 7355 sn, p. осн, сн, I: сн CONNECTION 7 oil 7356. sn, sya, Osn, SN, H C, H, connection 7 oil 7357 sv, SE, Os, NN n San, connection with oil t7zev sn. sn, Osn, sn, n sn, connection 7 oil 7359 sni with s1 n SK, seSUuN, connection c7 155-158 7zEo sn, SE, os, Ya Kk SK, connection OV kaspo 7361 sn. sn, osya, Osn, n Sun. connection 910 oil 7352 o si s1 n I sn. connection 1 « 7363 o s1 SE, H n SN, Connection s1 - 7364 se, si osv, Н N sk, connection 51 - 7365 sn, s os, s these SN. connection 51 - 7366 sn. si si H si, sn, bond s1 - t3e CH: SE, OSN, H n si, connection s1 - 7368 sn, CH, OSN, EE n sn, bond 1 - 7369 a "1 si Kk H C,H, zv 'yazozh 1 - 1370 a si SE, B n Syn. connection si - 73171 sy, si ose, nn n S.n, connection 01 - 1372 sn, sn, osn, si1 n Son, connection 1 and 7373 sya, s1 se NN sn, San" connection s1 - tu sy, SE, OS, n k sun, connection 51 - 7375 s, sun, Osn, E E san, zv 01 - 7376 o s: si n Kk SUN, connection C - 7377 o s SE, N n S.N, connection SI - 7378 SN, st1 ost, N n Sun, connection 1 - 7379 SN. art, Osn, cS1 n Son, connection 01 - 7382 sn si sg1 H sn; San, Communication - 7Zvi sia.

St, axis VN n SN, connection FI - 7382 sn, sn, Osn; ЕЕ Н СН, bond 1 - 7zaz o si si H |: с-С,Н, bond с - 7384 o сС1 св, Н Кк Е-С,Н; connection si - 7385 sia, C1 osE, H Нn s-SN; connection 0 SI - 7386 sn, sn, osn, s n se-Sun, connection 1 - 17387 sn, si s1 n SN; с-С,, connection 03 - zve CH, SE, Osn, Нн Не-С, connection - 1385 sya; St OS, in N e-S,N. SI connection - 7390 sec. si sv, n H e-SoH, connection 914 oil 7351 sch, "1 si n V s-s,n. zvNHZOK sii -

7391 sna si Se, n n s-S,. communication sbi5 oil 7392 sn, SI si Kk Nn s-b,, communication 915 - 7393 s s SE, nn «-s,n, ZvyAZoOK b16 339-340 7394 sna si si n n s-s, n, ЗБЯЗОМ p16 - 7395 сн. s SE, n n s-SuN, Connection 17 - tz95 sn, si si n n s-sIN, CONNECTION 017 oil 7197 sn; s Se, n n e-S,n, Connection "si18 - 7394 sty si si n n s-s,n, connection 018 oil 7389 sn, si s n sn, SYakh connection Ov oil 7409 sy; si Sta N K s-s,N, connection 19 - 7441 sn, sI1 si n n s-s,N, connection sIZ oil 74972 st, «1 si n Kk e-s,n, Connection 029 oil 7403 sn . s sv, Kk K s-SU, Communication p39 - 2494 sn, si «ii n n SN; connection 61 oil 7195 sv, "s si H 2 sn, seo s,n oil 7408 sn, s1 si Hn n sv, s-o 921 oil 7407 syu si si N n sene S"O 022 oil 1408 sk, (4 su n n 4-E- s-o SYA, oil s,v.sya, 7409 sn. lunch

Key: (e) o groups: 61 5 I-So so is I-Z 0 -O zho, 03 I va - h./ t s5 g Gret ob - sn.

OT 5 spesk, SE e rg-sneSsNoSN, "9 I-i vioz TON sn y

F11e too, 0I2- -

Us /y and /y si1- -- 142 well;

A I-i a15- I c15- sh- pla sleep

So 0 mi St

B, -O - and Y sat: and 4 Her C20 x 021: 1-4 sat 2225 I-4 sat (p) For the compounds designated as "oil", the spectral data are given below: Example 7056, spectral data:

Mass spectroscopy (EI): mass 363 (Ma-2), 361 (MU, 10095). Example 7086, spectral data: TI C Ac 0.25 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 8.91 (1H, 5), 7.72 (IN, a, 92-9.2 Gu), 6.90-6.84 (2H, t), 6, 08 (1N, aaad, U-15.4 Hz, 6.6 N, 1.4 Hz), 5.67 (1N, dda, 9U-15.4 Hz, 6.5 N, 1.5 Gu), 5.24 (1H, rg pentet, U-7.0 Hu), 3.85 (ZH, 5), 2.96 (2H, da, 9-7.5, 1.1 Hu), 2.47 ( ZN, 5), 1.81 (ZN, a, 9-7.0 Hz), 1.73 (ZN, ac 9U-6.2, 1.3 Gu), 1.41 (ZN, 6 9-7 .5 Hz).

Mass spectroscopy (MS-SI): t/e 339(3), 338(23), 337(100).

Example 7116, spectral data: TI C V; 0.15 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 8.96 (1H, 5), 7.68 (1H, a, 9U-8.4 Hz), 7.09 (1H, a, 9U-2.6 Gu ), 6.96 (1H, aa, 9-84, 2.6 Gu), 6.09 (1H, aadd, 9-15.4 Hz, 6.6H, 1.8

Hz), 5.67 (1H, adda, 9-15.4 Hz, 6.5H, 1.4 Hu), 5.23 (1H, Bg pentet, U-6.8 Hu), 3.87 (ZH , 5), 2.98 (2Н, а, 9-7.5 Hz), 1.82 (ЗН, а, 9-7.0 Hz), 1.73 (ЗН, ак 90-6.6, 1 .3 Hz), 1.40 (ZN, i, 9-7.5 Hz). Mass spectroscopy (MS-SI): t/e 360(7), 359(33), 358(23), 357(100).

Example 7145, spectral data: Tpl--78-7920. TI S V; 0.52 (30:70 ethyl acetate-hexane). "'NMR (300 MHz,

SOSIv):6 9.01 (1H, 5), 7.86-7.81 (2H, t), 7.68 (1H, y, 9-8.0 Gu), 6.38 (2H, aaa, 9-17.2 Hz, 10.6H, 5.8 Hz), 5.90-5.83 (IN, t), 5.40 (2H, aa, 9-10.6, 1.3 Hz), 5.29 (2H, a 0-17.2, 0.9 Hz), 2.97 (2H, a, 9-7.6 Hz), 1.41 (ZN, 6 9-76 Gu).

Mabs spectroscopy (Mnz-SI): t/e 396(8), 395(36), 394(25), 393(100). Analysis, calculation. for Sti9NieSIezMaya: C, 58.10;

H, 4.12; M, 14.26; found: C, 58.14; H, 4.28; M, 13.74.

Example 7146, spectral data: TI C V; 0.43 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIz) b 8 99 (1H, c), 7.84-7.79 (2H. t), 7.67 (1H, aa, 9-8.5, 1.1 Hu), 6.10 (1H, add, 9-15.4 Hz, 6.8H, 1.8 Hu), 5.70 (1H, ada, 9-15.4 Hz, 6.5H, 1.1 Hu), 5.24 (1H, pentet, U-7.0 Hu), 2.99 (2H, a, 9-7.5 Hz), 1.83 (ZH, a, 9-7.0 Hz), 1, 74 (ZN, a 9-6.6, 1.3 Gu), 1.40 (ZN, 5 92-7.5 Hz). Mass spectroscopy (MS-SI): t/e 398(7), 397(36), 396(25), 395(100).

Example 7231, spectral data: Tpl--78-887С. TI S V; 0.55 (50:50 ethyl acetate-hexane). NMR (300 MHz,

SOSI"): Main isomer: b 8.90 (1H, 5), 6.95 (2H, 5), 4.68-3.05 (BN, t), 3.02-2.92 (2H, t ), 2.70-2.55 (2H, t), 2.32 (ZH, 5), 2.20-2.00 (2H, t), 2.05 (ZH, 5), 1.96 ( ЗН, 5), 1.70-1.45 (4Н, t), 1.39 (ЗН, ии, 9-7.7 Hu), 0.93 (ЗН, и, 9-7.3 Hu);

Side isomer: 5 8.89 (1H, 5), 6.95 (2H, 5), 4.68-3.05 (6H, t), 3.02-2.92 (2H, t), 2, 70-2.55 (2H, t), 2.32 (ZH, 5), 2.20-2.00 (2H, t), 2.06 (ZH, 5), 2.01 (ZH, 5 ), 1.70-1.45 (4H, t), 1.38 (ZH, i, 9-7.7 Hz), 0.90 (ZH, i, 9-7.3 Hz). Mass spectroscopy (MH-SI): t/e, calc. for С25Нз5МаО»: 423.2760, found 423.2748; 425(5), 424(29), 423(100).

Analysis, calculation. for C25NzaMaO»o-NgO: C, 68.15; H, 8.24; M, 12.72; found: C, 67.80; H, 7.89; M, 12,24.

Example 7234, spectral data: TI C V; 0.46 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIzv): b 8.99 (1H, 5), 7.87 (1H, y, 9U-8.0 Hu), 7.83 (1H, 5), 7.68 (1H, a, 9U-8.0 Hu), 6.50 (1H, a, 9-3.0 Hz), 5.99 (1H, a, 9-3.0 Hu), 5.10 (IN, a, 9-10.6 Hu), 2.99-2.79 (2H, t), 2.20 (ЗН, 5), 2.10-2.00 (1Н, t), 1.30 (ЗН, 5 9-7.5 Hz), 1.00-0.90 (1H, t), 0.71-0.59 (2H, t), 0.56-0.46 (1H, t). Mass spectroscopy (MHz-SI): t/e 463(35), 461(100):

Example 7241, spectral data: Mass spectroscopy (MNzg-SI): t/e 371 (MAN, 10095). Example 7243, spectral data: TI C V; 0.43 (30:70 ethyl acetate-hexane). NMR (300 MHz, COS1z): b 9.01 (1H, 5), 7.85 (1H, a, 98.0 Hu), 7.83 (1H, 5), 7.69 (1H, y, 9-8.0 Hz), 5.24 (1H, ay, 9U-8.4, 2.5 Hz), 3.28 (IN, yes, 9-15.5, 7.5 Gu), 3, 14 (IN, yes, 9-15.5, 7.5 Hz), 2.56 (IN, 9, 9U-2.5 Hz), 1.78-1.67 (1H, t), 1.48 (ZH, i, 9-7.5 Hz), 0.92-0.81 (2H, t), 0.66-0.49 (2H, t). Mass spectroscopy (MH-SI): t/e, calcd. for SgoNi?SiIEziMa: 405.1094, found 405.1098; 408(8), 407(34), 406(25), 405(100).

Example 7249, spectral data: TI C V; 0.19 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 8.93 (1H,

5), 7.72 (1H, a, 9U-8.5 Gu), 7.37 (1H, a, 9-2.5 Hz), 7.18 (1H, ad, 9-8.5, 2 ,5 Hz), 5.23 (1H, aa, U-8,I, 2.6 Hu), 3.92 (ZH, 5), 3.31-3.04 (2H, t), 2.54 (1H, y, 9-2.6 Gu), 1.76-1.64 (1H, t), 1.47 (ZN, Her, 9-7.5 Hz), 0.90-0.80 ( 2H, t), 0.64-0.52 (2H, t). Mass spectroscopy (MNzg-SI): t/e, calc. for Sg2g1iNgobzMaO: 401.1603, found 401.1602; 403(6), 402(24), 401(100).

Example 7250, spectral data: TI C V; 0.17 (20:80 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 9.01 (1H, 5), 7.67 (1H, a, 9-8.5 Hz), 7.58 (1H, a, 9U-1.8 Gu ), 7.41 (1H, aa, o-8.5, 1.8 Hz), 5.53 (1H, a, uU-8.0, 2.6 Gu), 3.20 (IN, da, 9U-15.8, 7.5 Hz), 3.05 (IN, ad, 9-15.8, 7.5 Gu), 2.55 (1H, y, 9-2.6 Hz), 2, 42-2.29 (1H, t), 2.28-2.15 (1H, t), 1.46 (ЗН, и, 9-7.5 Hz), 1.04 (ЗН, 5 9-7 .5 Hz). Mass spectroscopy (MHz-SI): t/e, calculated for SiNi7C12M, 359.0830, found 359.0835; 364(2), 363(12), 362(14), 361(67 ), 360(24), 359(100).

Example 7259, spectral data: TI C V; 0.22 (20:80 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 9.01 (1H, 5), 7.67 (1H, j, 9-81 Hz), 7.58 (1H, a, 9J-1.8 Hz), 7.40 (1H, aa, 9-81, 1.68 Hu), 5.63 (1H, ai, 1-7.9, 2.5 Hu), 3.20 (IN, da, 9-15, 7, 7.7 Hu), 3.05 (IN, yes, 9-15.7, 7.7 Hz), 2.54 (1H, a, 9-2.5 Hu), 2.37-2, 24 (1H, t), 2.19-2.06 (1H, t), 1.60-1.45 (IN, t), 1.46 (ЗН, и, 9-7.7 Hz), 1 ,3539-1.25 (1H, t), 0.99 (ZH, y, 9U-7.3 Hz). Mass spectroscopy (MH3-SI): t/e, calculated for C1i9NiOSi2My: 373.0987, found 373.0984; 378(3), 377(12), 376(15), 375(66), 374(26), 373(100).

Example 7261, spectral data: TI C V; 0.52 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIzv): b 9.03 (1H, 5), 7.84 (2H, t), 7.68 (1H, aa, 9U-7.3, 0.7 Hu), 5, 65 (1H, ai, U-8,I, 2.6 Hu), 3.24-3.02 (2H, t), 2.55 (1H, a, 9-26 Hu), 2.33-2 .25 (1H, t), 220-212 (IN, t), 1.46 (ZH, 5 9U-7.5 Hz), 1.00 (ZH, i, 9-7.3 Hz). Mass spectroscopy (MH-SI): t/e, calcd. for SgoNioSiIEzMa: 407.1250, found 407.1243; 410(8), 409(36), 408(25), 407(100).

Example 7266, spectral data: TI C V; 0.19 (20:80 ethyl acetate-hexane). "'NMR (300 MHz, SOSIv): b 9.01 (1H, a, 9-1.5 Hu), 7.38 (1H, a, U-I.8 Hz), 7.24 (1H, a , --I.8 Hz), 5.70-5.58 (1H, t), 3.24-3.00 (2H, t), 2.55 (1H, a, 9-25

Hz), 2.40-2.25 (1H, t), 2.20-2.05 (1H, t), 2.10 (ZN, ai, 9-1.8 Hu), 1.62-1 .47 (1Н, т), 1.43 (ЗН, и, 9-7.5 Hz), 1.42-1.27 (IN, т), 1.00 (ЗН, и, 9-7.3 Hz). Mass spectroscopy (MH-SI): t/e, calc. for SgoNgiSi2Maya: 387.1143, found 387.1144; 392(3), 391(12), 390(16), 389(66), 388(27), 387(100).

Example 7268, spectral data: TI C V; 0.29 (20:80 ethyl acetate-hexane). NMR (300 MHz, SOSIzv): b 9.01 (1H, 5), 7.67 (1H, a, 9-8.5 Hz), 7.58 (1H, a, 9-22 Hz), 7 .41 (1H, ai, 0-8.5, 2.2 Hu), 5.60 (1H, a, 9-7.9, 2.6 Hu), 3.19 (1H, da, 9-15 ,3, 7.3 Hu), 3.05 (IN, ad, 9U-15.3, 7.3 Hu), 2.54 (1H, y, 2-2.6 Hz), 2.38-2 .23 (1H, t), 2.20-2.05 (1H, t), 1.58-1.44 (1H, t), 1.46 (ЗН, и, 9-7.3 Hz), 1.40-1.23 (5H, t), 0.87 (ZH, i, 9-7.0 Hz). Mass spectroscopy (MH-SI): t/e, calcd. for SgiNgzSi2My: 401.1300, found 401.1300; 406(3), 405(13), 404(17), 403(69), 402(28), 401(100).

Example 7270, spectral data: TI C B, 0.60 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 9.03 (1H, 5), 7.84 (2H, t), 7.68 (1H, ad, 9-9.01, 0.7 Hz), 5, 62 (1H, a, 9U-8,I, 2.6 Hu), 3.24-3.02 (2H, t), 2.55 (1H, a, 9-26 Hu), 2.34-2 ... 0.88 (ZH, i, 9-7.0 Hz). Mass spectroscopy (MH-SI): t/e, calcd. for Сг2НозСИЕзМы: 435.1563, found 435.1566; 438(9), 437(36), 436(27), 435(100).

Example 7279, spectral data: TI C V; 0.31 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 8.97 (1H, 5), 7.84 (2H, t), 7.68 (1H, a, 9-7.7 Hu), 4.74-4 .67 (1H, t), 3.45-3.36 (1H, t), 3.03 (2H, a, 9-7.7 Gu), 3.00-2.93 (1H, t), 1.93 (IN, i, U-2.7 Hu), 1.86 (ZN, a, 9-7.0 Hu), 1.43 (ZN, i, U-7.5 Hz). spectroscopy (MHz-SI): t/e 396(7), 395(34), 394(24), 393(100).

Example 7286, spectral data: TI C V; 0.29 (20:80 ethyl acetate-hexane). "'NMR (300 MHz, SOSIv): b 8.97 (1H, 5), 7.68 (1H, a, 9-84 Hu), 7.58 (1H, y, 9-1.8 Hz), 7.41 (1H, aa, 0-8/4, 1.8 Hu), 5.19 (1H, da, 9U-8.4, 2.6 Hu), 3.26 (tn, aa, 0O- 15.7, 7.3 Hz), 3.14 (1Н, ad, 9-15.7, 7.3 Hz), 1.88 (ЗН, а, 9-26 Hz), 1.70-1, 60 (1H, t), 1.47 (ZH, i 9U-7.3

Hz), 0.89-0.78 (2H, t), 0.60-0.43 (2H, t). Mass spectroscopy (MH-SI): t/e, calc. for SgoNizS12My: 385.0986, found 385.0992; 390(3), 389(12), 388(15), 387(66), 386(26), 385(100).

Example 7288, spectral data: Mass spectroscopy (MHz-SI): t/e 419 (Man, 100925).

Example 7295, spectral data: TI C V; 0.19 (20:80 ethyl acetate-hexane). "'NMR (300 MHz, SOSIv): b 8.99 (1H, 5), 7.67 (1H, a, 9-84 Hz), 7.57 (1H, a, 9-22 Hz), 7, 40 (1H, ay, yu-8.4, 2.2 Hz), 5.49 (1H, id, 9-7,7,2,2 Gu), 3.19 (IN, yes, 9-15, 3, 7.7 Hz), 3.05 (1H, ad, 9U-15.3, 7.7 Hz), 2.26 (1H, ad, 9-21.3, 7.7 Gu), 2, 13 (1Н, yes, 9-21.3, 7.7 Gu), 1.87 (ЗН, и, 9У-2.2 Hz), 1.45 (ЗН, 5 0-7.7 Hz), 1 ,01 (ZH, и, 9-7.7 Hz). Mass spectroscopy (MHz-SI): t/e, calculated for

StioNioSioMa: 373.0987, found 373.0987; 378(3), 377(13), 376(15), 375(68), 374(25), 373(100).

Example 7297, spectral data: TI C V; 0.48 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 9.01 (1H, 5), 7.83 (2H, t), 7.67 (1H, ai, 9-7.4, 0.8 Hz), 5, 51 (1H, ai, 9-8, I, 2.2 Hz), 3.25-3.03 (2H, t), 2.35-2.13 (2H, t), 1.88 (ZH, y, 9U-2.2 Hz), 1.45 (ZN, 5 0-7.5 Hz), 1.01 (ZN, y, 9-7.3 Hz). Mass spectroscopy (MH-SI): t/e, calcd. for

SgoNioSiIEzMa: 407.1250, found 407.1267; 410(8), 409(35), 408(25), 407(100).

Example 7306, spectral data: Mass spectroscopy (MHz-SI): t/e 429 (Man, 100925).

Example 7324, spectral data: TI C V; 0.38 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 8.99 (1H, 5), 7.84 (1H, a, 9-84 Hu), 7.83 (1H, a, 9-18 Hu), 7, 68 (1H, aa, y-8.4, 128 Hz), 7.36 (1H, a, 9-3 Hz), 6.51 (1H, a, 2-5

Hz), 6.39 (IN, aa, 9U-5.3 Hz), 5.78 (1H, ad, 9-9, 7 Gu), 3.00-2.85 (2H, t), 2, 75-2.52 (2H, t), 1.37 (ZN, 6 9-7.5 Gu), 0.98 (ZN, i, 9-7.5 Hz). Mass spectroscopy (MS-SI): t/e 439(1), 438(8), 437(34), 436(26), 435(100).

Example 7349, spectral data: TI C V; 0.20 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIzv): b 9.00 (1H, 5), 7.87 (1H, a, 9-8.0 Hz), 7.83 (1H, 5), 7.69 (1H, a, 9-8.0 Hu), 5.01 (1H, a, 9U-10.6 Hu), 2.93 (IN, ad, 9U-15.9, 7.5 Hu), 2.75 ( 1H, ad, 9-15.9, 7.5 Gu), 2.58 (ZH, 5), 2.04-1.94 (1H, t), 1.93 (ZH, 5), 1.33 (ZH, i, 9-7.5 Hz), 1.32-1.22 (1H, t), 1.00-0.87 (IN, t), 0.74-0.60 (ZH, t ). Mass spectroscopy (MH-SI): t/e, calcd. for SgzNg2SiEziM5O: 476.1465, found 476.1469; 478(35), 476(100).

Example 7351 spectral data: TI C V; 0.44 (30:70 ethyl acetate-hexane). "NMR (300 MHz, SOSIz"): b 8.99 (1H, 5), 7.88-7.82 (2H, t), 7.68 (1H, a, 9U-8.0 Hz), 6 .35 (1H, aada, O-17.2, 10.6H, 5.1 Hu), Z Hz), 5.33 (IN, Bg a, 9U-10.6 Hu), 5.26 (IN, rga, 9-17.2 Hu), 4.43-4.37 (1H, t), 3.02-2.90 (2H, t), 1.99-1.89 (1H, t), 1 ... t). Mass spectroscopy (MS-SI): t/e 411(1), 410(7), 409(34), 408(25), 407(100). 246 Example 7352, spectral data: TISA; 0.13 (20:80 ethyl acetate-hexane). NMR (300 MHz, SOSIz): b 8.96 (IN, 5), 7.69 (1H, y, 9U-8.4 Hz), 7.58 (1H, y, 9-22 Gu), 7 .41 (1H, da, y-8.8, 2.2 Hz), 6.33 (1H, aada, O-17.2, 10.6, 5.2

Hz), 5.35-5.20 (2H, t), 4.42-4.35 (1H, t), 3.03-2.88 (2H, t), 2.00-1.89 ( 1Н, t), 1.40 (ЗН, и, У-7.6 Hz), 0.92-0.82 (1Н,

t), 0.62-0.52 (2H, ha), 0.40-0.30 (1H, t). Mass spectroscopy (MH-SI): t/e, calc. for С1и9СиМа: 373.1000, found 373.0995; 378(3), 377(12), 376(15), 375(66), 374(26), 373(100).

Example 7355, spectral data: Mass spectroscopy (MS-SI): t/e 337 (MAN, 100925).

Example 7356, spectral data: Mass spectroscopy (MS-SI): t/e 365 (MAN, 100925).

Example 7357, spectral data: TI C V; 0.19 (30:70 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 8.91 (1H, 8), 7.70 (1H, a, 9-84 Hu), 7.35 (1H, a, 9-26 Hu), 7, 19 (1H, aa, 9-84, 2.6 Hu), 6.42 (1H, avda, O-16.9, 10.3, 6.6 Hu), 527 (IN, a, 9U-10, 2 Hz), 5.14 (1H, a, 9-17.3 Hz), 5.08-4.99 (1H, t), 3.91 (ZH, 5), 2.99-2.90 ( 2H, t), 2.42-2.29 (1H, t), 2.27-2.15 (1H, t), 1.39 (ЗН, и, 9U-7.5 Hz), 1.38 -1.10 (2H, t), 0.95 (ZH, y, 9-7.1 Hz). Mass spectroscopy (MHz-SI): t/e, calculated for Sg1iNgaEziMaO: 405.1915, found 405 ,1923; 407(5), 406(24), 405(100). Analysis, calculations for

Sg21NazEz Mao: S, 62,37; H, 5.73; M, 13.85; found: C, 62.42; H, 5.73; M, 13.48.

Example 7358, spectral data: Mass spectroscopy (MS-SI): t/e 379 (MAN, 100925).

Example 7360, spectral data: TI C V; 0.13 (30:70 ethyl acetate-hexane). "'NMR (300 MHz, SOSIv): b 8.91 (1H, 8), 7.68 (1H, a, 9-88 Hz), 7.935 (1H, a, 9-26 Gu), 7.16 ( 1H, aa, 9-88, 2.6 Hz), 6.15-6.06 (IN, t), 5.73-5.63 (1H, t), 5.28-5.18 (1H, t), 3.91 (ZH, 5), 2.96 (2H, a, 9-74 Gu), 1.82 (ZH, a, 9-7.3 Hz), 1.74 (ZH, a 9 -66, 1.3 Hz), 1.39 (ZN, and 9y-7.4 Hu). Mass spectroscopy (MHz-SI): t/e, calculated for SgoNogEziMmaO: 391.1733, found 391.1736 393 (3), 392(23), 391(100).

Example 7361, spectral data: TI C V; 0.43 (50:50 ethyl acetate-hexane). NMR (300 MHz, SOSIzv): b 8.96 (1H, 8), 7.42 (1H, 5), 6.84 (1H, 5), 5.55 (1H, ai, uU-5.5 , 2.2 Hz), 3.94 (ZH, 5), 3.92 (ZH, 5), 3.49-2.98 (2H, t), 2.54 (IN, a, y-2, 6 Hu), 2.45 (ZN, 5), 2.35-2.16 (2H, t), 1.48 (ZN, i 9-7.5 Hz), 1.03 (ZN, i, 9 -7.5 Hz). Mass spectroscopy (MH-SI): t/e, calcd. for SgiNg5MaO»: 365.1978, found 365.1966; 367(6), 366(24), 365(100).

Example 7390, spectral data: TI C V; 0.45 (30:70 ethyl acetate-hexane). "'NMR (300 MHz, SOSIv): b 8.99 (1H, 8), 7.88 (IN, y, uU-8.0 Gu), 7.83 (1H, 5), 7.69 (IN , a, 9-80 Hz), 7.30-7.22 (1H, t), 7.07-7.01 (IN, t), 6.99-6.92 (1H, t), 5, 25 (IN, a, U-10.2 Hz), 2.97-2.78 (2H, t), 2.23 (1H, ri), 1.32 (ZN, Her, 957.3 Hz), 1.10-1.00 (1H, t), 0.81-0.71 (1H, t), 0.64-0.54 (1H, t), 0.50-0.40 (1H, t ).Mass spectroscopy (MN3-SI): t/e, calculated for Cg2NiZSiEzyme5: 463.0971, found 463.0960; 467(3), 466(10), 465(99), 464(28), 463 (100).

Example 7392, spectral data: TI C V; 0.44 (30:70 ethyl acetate-hexane). "'NMR (300 MHz, SOSIv): b 8.99 (1H, 8), 7.88 (1H, y, 9U-8.0 Hz), 7.83 (1H, 5), 7.68 (IN , a, 9-80 Hz), 7.30 (1H, Brg a, 9-48 Hz), 7.18 (1H, Bg a, 9-48 Gu), 6.92 (1H, t), 5, 12 (1H, y, U-9.9 Hu), 2.92-2.67 (2H, t), 2.13 (1H, Bo, 1.28 (ZN, 9-7.5 Hu), 1 .08-0.99 (1H, t), 0.79-0.69 (IN, t), 0.55-0.45 (2H, t). Mass spectroscopy (MHz-SI): t/e , calculated for C22NiOSiIEzMa5: 463.0971, found 463.0953; 467(3), 466(10), 465(39), 464(29), 463(100).

Example 7396, spectral data: TI C V; 0.27 (20:80 ethyl acetate-hexane). NMR (300 MHz, SOSIzv): b 8.96 (1H, 8), 7.67 (1H, a, 9-8, Hz), 7.58 (1H, a, 9-1.8 Hu), 7.41 (1H, aa, 9-80, 1.8 Hz), 6.86 (1H, 5), 5.83 (1H, aa, 9U-9.9, 6.2

Hz), 4.43 (2H, a, 9-7.3 Hz), 2.98 (2H, a, 9-7.7 Hz), 2.91-2.78 (1H, t), 2, 63-2.49 (1Н, т), 1.42 (ЗН, и, 9У-7.7 Gu), 1.40 (ЗН, B 97.3 Hz), 1.39-1.19 (2Н, t), 1.00 (ZN, i, 9U-7.3 Hz). Mass spectroscopy (MH-SI): t/e, calcd. for

SgZiNgaSi2M5Oz: 488.1256, found 488.1252; 493(3), 492(13), 491(18), 490(68), 489(28), 488(100).

Example 7398, spectral data: TI C V; 0.11 (20:80 ethyl acetate-hexane). NMR (300 MHz, SOSIz): b 8.99 (1H, 8), 7.72 IN, a, min Hz), 7.59 (1H, a, U-1.8 Gu), 7.42 ( 1H, ad, 9-81, 1.8 Hz), 5.40 (1H, aa, 9-10.4, 5.0 Gu), 442 (2H, a, 9-74 Hz), 3.00- 2.90 (2H, t), 2.66-2.52 (1H, t), 2.51-2.38 (1IN, t), 1.46 (ZH, ii, 9U-7.4 Hz) , 1.41 (ZN, 5 0-73

Hz), 1.40-1.10 (2H, t), 0.98 (ZH, i, 9-7.2 Hz). Mass spectroscopy (MNzg-SI): t/e, calc. for Sg24No5Si«MvOx: 531.1315, found 531.1315; 531(100).

Example 7399, spectral data: TI C V; 0.13 (20:80 ethyl acetate-hexane). NMR (300 MHz, SOSIv): b 8.98 (1H, 8), 7.38 (1H, a, 9-1.8 Hu), 7.23 (1H, a, 91.8 Hu), 6 ,15-6.06 (1H, t), 5.76-5.63 (1H, t), 5.26-5.20 (1H, t), 2.96 (2H, a, 9-74 Hz ), 2.10 (ZN, 5), 1.83 (ZN, a, 9-7.0 Hu), 1.74 (ZN, a, 9-6.6 Hu), 1.37 (ZN, and , 9-7.4 Hz). Mass spectroscopy (MH-SI): t/e, calcd. for Si9NaSi»My: 375.1117, found 375.1123; 380(2), 379(12), 378(15), 377(66), 376(26), 375(100).

Example 7401, spectral data: TI C V; 0.20 (ethyl acetate). NMR (300 MHz, SOSIv): b 8.99 (1H, 5), 7.71 (1H, 9, 9-84 Hz), 7.58 (1H, a, 9-18 Hz), 7, 41 (1H, ay, d-8.4, 1.8 Hz), 7.11 (1H, a, U-1.1 Hu), 6.87 (1H, a, 9U-1.1 Hu) , 5.41 (IN, a, 2-10.3 Gu), 3.34 (ZN, 5), 3.08 (1H, ad, 9U-15.8, 7.7 Hz), 2.89 ( IN, 4, 915.8, 7.7 Hz), 2.39-2.25 (1H, t), 1.14 (ZN. B 9-7.7 Hz), 1.07-0.97 ( 1H, t), 0.70-0.58 (2H, t), 0.52-0.42 (1H, t). Mass spectroscopy (MHz-SI): t/e, calculated for SgiNgiSioMa: 4271205 , found 427,1196; 429(66), 427(100).

Example 7402, spectral data: Mass spectroscopy (MHz-SI): t/e 424 (Man, 100925).

Example 7404, spectral data: Mass spectroscopy (MHz-SI): t/e 419 (Man, 100925).

Example 7405, spectral data: Mass spectroscopy (MH-SI): t/e 487 (Man, 100925).

Example 7406, spectral data: Mass spectroscopy (MH-SI): t/e 501 (Man, 100925).

Example 7407, spectral data: Mass spectroscopy (MH-SI): t/e 517 (Manet, 100925).

Example 7408, spectral data: Mass spectroscopy (MH-SI): t/e 457 (Manet, 100925).

Example 7409, spectral data: Mass spectroscopy (MH-SI): t/e 429 (Man, 100925).

Application

A test for the binding of SAB-NI1 receptors for the assessment of biological activity

Below is a description of the procedure for isolating cell membranes containing cloned human SAB-NI receptors for use in a standard binding assay, as well as a description of the assay itself.

Matrix RNA was isolated from human hippocampus. The mRNA was reverse transcribed using oligo(a) 12-18, and the coding region was amplified by ROSA from initiation to termination codons. The resulting ROSA fragment was cloned into the EsoyAM site of the rOEEMU, from where this insert was regenerated using Khpo!/!-Khvai and cloned into Khpo!--Khrai! sites of the rtZag vector (which contains the SMMU promoter, 5M40 TT splice and early poly A markers, the Epstein-Barr virus replicator (Ervivip-Va!tt) and a hygromycin-selective marker). The resulting expression vector named rysiCAEVA was transfected into 293 EVMA cells, and cells harboring the episome were selected in the presence of 4A00 mM hygromycin. Cells that had undergone 4 weeks of selection in hygromycin were pooled, adapted to growth in suspension, and used to generate membranes in the binding assay discussed below. Individual aliquots containing approximately 1x103 suspended cells were then centrifuged to pellet and frozen.

For the binding assay, the above-mentioned pellet frozen after centrifugation, containing 293 EVMA cells transfected with NSAID receptors, was homogenized in 10 ml of ice-cooled tissue buffer (50 mM NEREB5 buffer, pH 7.0, containing 10 mM MoSi»?, 2 mM EaTA (ethylene glycol tetraacetic acid), mg/l aprotinin, 1 mg/ml leupeptin and 1 mg/ml pepstatin). This homogenate was centrifuged at 40,000 V for 12 minutes, and the obtained sediment was again homogenized in 10 ml of tissue buffer. After another centrifugation at 40,000 x 9 for 12 minutes, this sediment was resuspended to a protein concentration of 360 mg/ml for use in the specified sample.

Binding assays were performed in 96-well plates; each cell had a capacity of ZOO ml. To each cell, 50 ml of solutions of the tested drugs were added (final concentrations of the drug varied from 1079 to 109 M), 100 ml of 725)-CAE-VIiV4i (125)-0-SVE) (final concentration of 150 pM) and 150 ml of the cell homogenate described above. The plates were then incubated at room temperature for 2 hours, and the incubates were filtered through CE/E filters (pre-impregnated with 0.395 polyethyleneimine) using an appropriate cell harvester. Before removing individual filters to evaluate radioactivity using a gamma counter, they were washed 2 times with ice-cooled sample buffer.

Curves of inhibition of 125)-0-SVE binding to cell membranes at different dilutions of the tested drug were analyzed using the LIGAND (PISAMO) curve fitting program by the iterative method (R.U. Mypsop apa 0. Nkodraga, Apai. Viospet., 107: 120 (1980), which gives Ki values for inhibition, which are then used to estimate biological activity.

Alternatively, in binding assays similar to those discussed above, tissues and cells that naturally express CAE receptors can be used.

A compound is considered active when it has a value of K| for inhibition of SAE is less than about 10,000 nm.

Inhibition of SAE-stimulated adenylate cyclase activity

Inhibition of CAE-stimulated adenylate cyclase activity can be carried out by the method described in a. Vanadiia eii ai., Zuparze 1:572 (1987). Briefly, the tests are carried out at 37"C for 10 minutes in 200ml of buffer containing 100mM Ttiv-HCI (pH 7.4 at 37"C), 10mM Masi, 0.4mM ESTA, 0.195 B5A (bovine serum albumin) , 1 mM isobutylmethylxanthine (IVMH), 250 units/ml phosphocreatine kinase, 5 mM creatine phosphate, 100 mM guanosine 5'-triphosphate, 100 nM osv, antagonist peptides (concentration range from 1079 to 105 M) and 0.8 mg of primary wet tissue (approximately 40- bOmg protein). Reactions were initiated by adding 1 mM

ATRA2RI|ATP (adenosine triphosphate) (approximately 2-4 mCi/tube) and finished by adding 100 ml of 50 mM Ttiv-

CARRIERS 45MM ATP and 295 Natriidodecylsulfate. To control the regeneration of cAMP (cyclic adenosine monophosphate), 1 ml of IZN was added to each test tube before separation. CAMP (approximately 40,000 decays/minute). Separation of GRI SAMR from G2RI| ATP was carried out by successive elution through columns with Dovex (Yuozmekh) and aluminum oxide.

Biological tests on a living organism

The activity of the compounds of this invention can be assessed using any biological test available and acceptable in the field. Illustrative tests include sound startle test, stair climbing test, and chronic use test. These and other models, useful for testing the compounds of this invention, are outlined in the work of S.M. Vepidde apa A). Oipp, Vgaip

Vezeagsip Nehemiah 15:71 (1990). The compounds can be tested on any species of rodents or small mammals.

The compounds of this invention are useful in the treatment of imbalances associated with abnormal levels of adrenocorticotropic hormone-releasing factor in patients suffering from depression, affective disorders and/or disorders caused by anxiety-depressive syndromes.

The compounds of this invention can be prescribed for the treatment of these abnormalities in any way that ensures contact of the active agent with the site of its action in the body of a mammal. They can be prescribed in any conventional way that is acceptable for use in combination with pharmaceutical preparations, both as a single therapeutic agent and as a combination of therapeutic agents. They can be prescribed separately, but preferably with a pharmaceutical carrier, the choice of which depends on the chosen regimen and standard pharmaceutical practice.

The choice of dosage will vary depending on known factors, such as the pharmacodynamic characteristics of this agent, the method and scheme of its appointment; age, health and weight of the patient; nature and degree of development of symptoms; type of other prescribed means of treatment; frequency of treatment and desired effect. For use in the treatment of these diseases, the compounds of this invention can be prescribed orally at a daily dosage of the active ingredient from 0.002 to 200 mg per kg of body weight. Of course, a dose of 0.01 to 10 mg/kg in the form of 1-4 single doses (per day) or in the form of a long-acting drug will be effective for obtaining the desired pharmacological effect.

Dosage forms (compositions) acceptable for the purpose contain from about 1 mg to about 100 mg of active ingredient per unit. In these pharmaceutical compositions, the active ingredient will, of course, be present in an amount that is approximately 0.5-95 wt.9o of the total weight of this composition.

The active ingredient may be administered orally in solid dosage forms such as capsules, tablets, and powders, or in liquid dosage forms such as elixirs, syrups, and/or suspensions. The compounds of this invention can also be administered parenterally, in the form of sterile liquid dosage forms.

Gelatin capsules contain the active ingredient and an acceptable carrier such as, for example, lactose, starch, magnesium stearate, stearic acid or cellulose derivatives. Similar diluents can be used to make compacted tablets. Both tablets and capsules can be manufactured as sustained-release products to ensure continuous release of the therapeutic agent over a period of time. Compacted tablets can be coated with sugar or a film to mask an unpleasant taste or protect the active ingredients from exposure to the atmosphere, or for selective breakdown in the gastrointestinal tract.

intestinal tract.

Liquid dosage forms for oral administration may contain dyes and flavors that facilitate the patient's use of the medication.

In general, acceptable carriers for parenteral solutions include water, pharmaceutically acceptable oils, saline, aqueous dextrose (glucose), and similar sugar solutions and glycols such as propylene glycol or polyethylene glycol. It is preferable when solutions for parenteral administration contain a water-soluble salt of the active ingredient, acceptable stabilizers and, when necessary, buffer substances. Acceptable stabilizers are such antioxidants as sodium bisulfite, sodium sulfite, or ascorbic acid, which can be used separately and in combination. In addition, citric acid and its salts and EDTA are used. In addition, parenteral solutions may contain preservatives such as benzalkonium chloride, methyl or propyl paraben, and chlorobutanol.

A list of acceptable pharmaceutical carriers is given in "Netipdiopye Rpappaseciisa! bsiepsev", A. Ovoy, which is commonly referred to in this field.

Useful pharmaceutical dosage forms for the administration of the compounds of this invention may be illustrated as follows:

Capsules

A substantial number of single capsules can be made by filling standard two-cell hard gelatin capsules with 100 mg of powdered active ingredient, 150 mg of lactose, 50 mg of cellulose, and bmg of magnesium stearate.

Soft gelatin capsules

Prepare a mixture of the active ingredient with easily digestible oil such as soybean, cotton or olive oil and inject it with the help of a discharge piston pump into the gelatin to form soft gelatin capsules containing 100 mg of the active ingredient. Then the capsules are washed and dried.

Tablets

A significant number of tablets can be prepared by conventional methods, so that a unit dose will contain 100 mg of active ingredient, 0.2 mg of colloidal silicon dioxide, 5 mg of magnesium stearate, 275 mg of microcrystalline cellulose, 11 mg of starch and 98.8 mg of lactose. Appropriate coatings can be applied to the manufactured tablets to improve taste and protect against adsorption.

The compounds of this invention may also be used as reagents or standards in biochemical studies of neurological function, dysfunction and disease.

Although the description of the present invention is limited to certain preferred embodiments, other embodiments will also be apparent to those skilled in the art. Therefore, the present invention is not limited to the given description and examples of variants, but can be modified or changed without losing its essence.

The full scope of the invention is outlined by the following claims.

Claims (6)

1. Imidazopyrimidines and imidazopyridines of formula (1) you My AV from v-x-k. .Y M - B Iv) (1) or their stereoisomer or a pharmaceutically acceptable salt form, in which: A is M or C-B7; B is M or C-B8; provided that at least one of the groups A and B is M; p is an aryl or heteroaryl group attached through an unsaturated carbon atom; X is selected from SN-VU, M-V!E, O, 5(O)n and connection; n equals 0, 1 or 2; IN! is selected from C1-10 alkyl, C1-10 alkenyl, C1-10 alkynyl, C3-z cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, C1-4 alkoxy- Sil alkyl, -502-C1-10 alkyl, -502 -812 and -5O2-B'; IN! is replaced by 0-1 substituents selected from -СМ, -5(О)claim 8/y5, -BOVza, -СО»в1za, "-МВзабО вза, -(СОВа) 5, - MmA'zaSOMAzadyea, " MA Zabov, "SOM of 1-morpholinyl, 1-piperidinyl, 1-piperazinyl, and C3-C cycloalkyl, where 0-1 carbon atoms in Ca-C cycloalkyl are replaced by a group selected from -O-, -5(О )p-, -МАЗа-, -МСО»ББ., - МСО В - and -М5О2В!о-, and where Ma in 1-piperazinyl is substituted by 0-1 substituents selected from За, СО», СОв'Ета 50289; IN! is also substituted with 0-3 substituents independently selected in each case from B", B!E, B/E, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkynyl, Bg, Si, E, I, C1-4 haloalkyl, -OV'Za, -YVZadyeA, C..4 alkoxy-C-4 alkyl and C3.in cycloalkyl, which is substituted by 0-1 BZ and in which 0-1 carbon atoms of Ca-in cycloalkyl are replaced by - AT-; provided that B! is different from: (a) cyclohexyl-(CHg)2-group; (p) C-cyclopropyl-C-methoxypropyl group; (c) unsubstituted -(alkoxy)methyl group; and (a) 1-hydroxyalkyl group; also provided that when EV! alkyl is substituted by OH, the carbon atom adjacent to the M ring is different from CH2e; B": is aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each Kg being 0-1 substituted. -OB!" and 0-5 substituents selected independently in each case from C1-e alkyl, C3-e cycloalkyl, Bg, C1-e, E, I, C1-4 haloalkyl, -CM, nitro, 5H, -5(0)08! 8, -SOV!", -OS(О0)8!8, -MAZaSOV!, -Ш(СОВ'7", -Мв'ЕСОМАадиза, - МАзасо»гВв!, -МА7tad'za, and -сСОМvad'za: B!” is heteroaryl and is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted on 0-4 carbon atoms by a substituent chosen independently in each case from Ci-e alkyl, C3-e cycloalkyl, Bg, Si, E, I, Ci-4 haloalkyl, -CM, nitro, - ОВ, 5Н, -5 (0)tV!8, -"SOV", -OS(O)VV, -MATzaSOV", -SHSOV", -MAZaSOMAta d'za, "-MATzaSO"vV, "MA ad'tza, and - СОМ ard'za, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from Ba, СОгв'в, Сов and 502; IN! is a heterocyclyl and a saturated or partially saturated heteroaryl, each heterocyclyl is a substituent substituted on 0-4 carbon atoms, independently selected in each case from C1-e alkyl, C3-e cycloalkyl, Bg, C1, E, I, C4 haloalkyl, - СМ, nitro, -ОВЗа, 5Н, -5(О)пВы5, -СОВЗа, -ОС(О)В5, -МаесSOвВЗа, -ЩСОВЗа)», - MA'ZSOMvzad'sa, -Yuv'zasOgvyu, -MV 'Zad'ba, and -SOMV'Zad'sa, and each heterocyclyl is substituted on any nitrogen atom with 0-1 substituents selected from B'Za, CO", CO, and 50285, and where any sulfur atom , if necessary, is mono- or dioxidized; provided that K! is different from -(CHg):-4-aryl, -(CHg)i-4-heteroaryl, or -(CHg):-4-heterocycle, wherein the aryl, heteroaryl, or heterocyclic group is substituted or unsubstituted; IN? is selected from C1-4 alkyl, C3-6 cycloalkyl, C2-4 alkenyl, and C1-4 alkynyl and is substituted with 0-3 substituents selected from -CM, hydroxy, halo, and C1-4 alkoxy; alternatively, B: in the case where X is a bond, is selected from -CM, CEz, and CE; BZ, B' and EZ are independently selected in each case from H, HG, SI, E, I, -CM, C1-4 alkyl, C3-6 cycloalkyl, C1-4 alkoxy, C1-4 alkylthio, C1-4 alkylsulfinyl, C-4 alkylsulfonyl, amino, C-4 alkylamino, (C1-4 alkyl)2g amino and phenyl, each phenyl being substituted with 0-3 groups selected from C-7 alkyl, C3-3 cycloalkyl, Bg, C1, E , I, C1 haloalkyl, nitro, C1-6 alkylamino, C1-6 alkylamino, and C1-6 alkyl)2 amino; provided that when VE! is unsubstituted C 1-6 alkyl, then EZ is different from substituted or unsubstituted phenyl; B3 and B" are independently selected in each case from H, C1-4 alkyl, C3-e cycloalkyl-C1-4 alkyl and C3-c cycloalkyl; B"3 is selected from H, C1-4 alkyl, C4 haloalkyl, C3- 4 alkoxy-C1-4 alkyl, C3-cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, aryl, aryl (C1-4 alkyl)-heteroaryl and heteroaryl (C3-4 alkyl)-; d'za and v/ba are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-6 cycloalkyl and C3-6 cycloalkyl-C1-6 alkyl; B" is selected from C-4 alkyl, C-4 haloalkyl, C-4 alkoxy-C-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-Ci-e alkyl, aryl, aryl (Ci-4 alkyl)-- heteroaryl and heteroaryl (Ci-4 alkyl)- and benzyl, each benzyl is substituted on the aryl component 0-1 with substituents selected from C-4 alkyl, Bg, C-4, E, I, C-4 haloalkyl, nitro, C- 4-Alkoxy, C-4-halo-Alkoxy and dimethylamino; dza is selected from C-4-alkyl, C-4-haloalkyl, C-4-Alkoxy-C-4-alkyl, C3-e cycloalkyl, C3-e cycloalkyl-Ci-v alkyl and benzyl, each benzyl is substituted on the aryl component with 0-1 substituents selected from C-4 alkyl, Bg, C1, E, I, C1-4 haloalkyl, nitro, C4-4 alkoxy, C4-4 haloalkyl, and dimethylamino; Vo is selected from Ci-4 alkyl, Ci-4 haloalkyl, Ci-4 alkoxy-Ci-4 alkyl, C3-- cycloalkyl and C3-e cycloalkyl-C1-6 alkyl; B" is chosen independently in each case from H, Si. alkyl, C3-7 cycloalkyl, C3-e cycloalkyl-C:-e alkyl, phenyl and benzyl, each phenyl or benzyl is substituted on the aryl component 0-3 groups selected from C-4 alkyl, Bg, SI, E, I, C-4" haloalkyl, nitro, C-4" alkoxy, C-4 haloalkoxy and dimethylamino; Visa is selected independently in each case from H, C1-6 alkyl, C3-7 cycloalkyl and C3-6 cycloalkyl-C1-6 alkyl; A" is selected in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C3-e cycloalkyl-C1-e alkyl, C1" alkoxy-C12 alkyl, C1-4 haloalkyl, B'5(O)p-Ci-a alkyl, and B!" M-C". 4 alkyl; BZ and BZ are independently selected in each case from H, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 3 -E cycloalkyl-C 1 -C 6 alkyl, C 1 -C 6 -C 6 alkyl, and C 1 -C 4 haloalkyl; as an alternative, in ME!"В"With component B" and В!" together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted 0-1 with substituents selected from B"3, CO2B'Y, SOB" and 5028; alternatively, in ME"»B!zB component B!75 and B together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from BZ, СО28В!", Сов! and 5028!я; Ba and в'Za are independently selected in each case from H, C1-6 alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl and C1-4 haloalkyl; aryl is independently selected in each case from phenyl, naphthyl, indanyl and indenyl, each aryl being substituted with 0-5 substituents independently selected in each case from C1-6 alkyl, C3-cycloalkyl, methylenedioxy, C1-4 alkoxy-C1-4 Alkoxy, -OB!", Vg, SI, E, I, Ci-4 haloalkyl, -SM, -MO», 5Н, -5(О)claim 8!8, -СОВ!", -СО28!" -OS(OVV, - MA"SOV'", -SHSOVl", -MA'SOMAVya, -MAZSO2VV, -MV'TV!I and -"SOMA! VZ ii up to 1 phenyl, each phenyl substituent is substituted with 0-4 substituents , selected from C1-6 alkyl, C1-6 alkoxy, Bg, C1, E, I, -CM, dimethylamino, C3, CoE5, OC3, 5O2Me, and acetyl; heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, triazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3- dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl, and benzodioxane, each heteroaryl is a 0-4 carbon substituted substituent selected independently in each case from C1 -is alkyl, C3-is cycloalkyl, Bg, Si, E, I, Si-4 haloalkyl, -SM, nitro, -OB!", 5H,. -5(O)tB"8, -SOV'", - BO28!", -OS(O)B8, -MASOV, -ShS ОВ' 2, -MA'SOMA"Vya, -"MAZSO"2B'8, -MA!VZ and -SOMV""B"", and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected of B"5, CO"gvyaa, SOV'cha and 502812: and, provided that when O is imidazole or triazole, PE! is different from unsubstituted C1-C linear or branched alkyl, or C3-C3 cycloalkyl. 2. The compound according to claim 1, which differs in that it corresponds to the compound of the formula Ia: В M с в выхХ- M dv Кк г (Iv). 3. The compound according to claim 1, which differs in that it corresponds to the compound of the formula Ir: in! and x KE! M h Kk k- h- ma v) (15;. 4. The compound according to claim 1, which differs in that it corresponds to the compound of the formula I: IN M. V z. g in M or (Is). 5. Pharmaceutical composition, which includes: a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of formula (1): vi i Z M Ah KE ; ее к-к- M «- Iv) (1) or its stereoisomer or a pharmaceutically acceptable salt form, in which: A is M or C-B7; B is M or C-B8; provided that at least one of the groups A and B is M; p is an aryl or heteroaryl group attached through an unsaturated carbon atom; X is selected from SN-VU, M-VO, O, 5(O) n and connection; n equals 0, 1 or 2; IN! is selected from C1-10 alkyl, C1-10 alkenyl, C1-10 alkynyl, C3-3 cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, C1-4 alkoxy- C.a alkyl, -502-Ci1-io alkyl, -502-812 and -"502-B/E; IN! is replaced by 0-1 substitutes selected from -СМ, -5(О)claim 8175, -СОВза, -СО»вВ1за, - Маасовза, "(СО Вза) ", - mAgasOMAZad'sa, -d'zasOgvo, " COM, 1-morpholinyl, 1-piperidinyl, 1-piperazinyl, and C3-C cycloalkyl, where 0-1 carbon atoms in Ca cycloalkyl are replaced by a group selected from -O-, -5(O)n-, -MA13a- , -МСО»ВБ., - МСО В - and -М5О2В!о-, and where Ma in 1-piperazinyl is substituted by 0-1 substituents selected from Za, СО», boOvВ'bta 502; IN! is also substituted with 0-3 substituents independently selected in each case from 2, BB, VIe, C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, Hg, C1, E, I, C1-4 haloalkyl, - ОВ'За, -МВЗадвба and Сз.в cycloalkyl, which is substituted by 0-1 BZ and in which 0-1 carbon atoms of Св cycloalkyl are replaced by -О-; provided that B! is different from: (a) 3-cyclopropyl-3-methoxypropyl group; (b) unsubstituted -(alkoxy)methyl group; and (c) 1-hydroxyalkyl group; provided also that when E! alkyl is substituted by OH, the carbon atom adjacent to the M ring is different from CH2g; B1z is aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each B12 is substituted with 0-5 substituents independently selected in each case from C1-e alkyl, C3-e cycloalkyl, Bg, C1-e, E, I, C1-4 haloalkyl, -SM, nitro, - OB, 5H, -(O) B", -SOV', -OS(OB', -MmvA'SOV!, -MSOV", -mv'gasomMvtadiza, - Mm'ya-asO»v8, -Mvtadiza and - COM tad'za: B» is heteroaryl and is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl , benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, And in 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl, and benzodioxane, each heteroaryl is a substituted 0-4 carbon atom substituent that is independently selected in each case C-is alkyl, C3-is cycloalkyl, Bg, Si, E, I, Ci-4 haloalkyl, -CM, nitro, - ОВ", 5Н, -5(О)тВ!8, -"СОВ '", -ОС(ОВ'8, -МаасОВв!", -ЩСОВ7», -«MA'zasOMAaviza, "Mao" vyV, -"MA7ad'za and - СОМ ard'a, and each heteroaryl is substituted by any which nitrogen atom has 0-1 substituents selected from В/ча, СОгв'в, Сов and 502; B!: is a heterocyclyl and is a saturated or partially saturated heteroaryl, each heterocyclyl is a substituted 0-4 carbon atom substituent independently selected in each case from C1-e alkyl, C3-e cycloalkyl, Bg, C, E, I, Si haloalkyl, -SM, nitro, ОВ'За, 5Н, -5(О)пА5, -бОВ1За, -ОС(О)Вв, -МвАзабОвВЗа, -(СОвЗа)», - МА'ЗСОМвзад'sa, -Юв' zasOgvyu, -MV'Zad'ba, and -SOMV'Zad'sa, and each heterocyclyl is substituted on any nitrogen atom with 0-1 substituents selected from В'За, СО2В9, СОВ5 and 50285, and where any which sulfur atom, if necessary, is mono- or dioxidized; IN? is selected from C1-4 alkyl, C3-1 cycloalkyl, C1-1 alkenyl, and C1-4 alkynyl and is substituted with 0-3 substituents selected from -CM, hydroxy, halo, and C1-4 alkoxy; alternatively, B, in the case where X is a bond, is selected from -CM, CEz, and CoEv; BAZ, B" and BZ are independently selected in each case from H, Bg, SI, E, I, -CM, C-4 alkyl, C3-1 cycloalkyl, C1-4 alkoxy, C-4 alkylthio, C-4 alkylsulfinyl, C-4 alkylsulfonyl, amino, C-4 alkylamino, (C1-4 alkyl)2g amino and phenyl, each phenyl being substituted with 0-3 groups selected from C-7 alkyl, C3-6 cycloalkyl, Bg, C1, E , I, C1-4 haloalkyl, nitro, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylamino and (C1-6 alkyl)2 amino; provided that when VE! is unsubstituted C 1-6 alkyl, then EZ is different from substituted or unsubstituted phenyl; B3 and B" are independently selected in each case from H, C1-4 alkyl, C3-e cycloalkyl-C1-4 alkyl and C3-b cycloalkyl; B13 is selected from H, C1-4 alkyl, C1-haloalkyl, C3- 4 alkoxy-Ci-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, aryl, aryl (C1-4 alkyl)-heteroaryl and heteroaryl (C3-4 alkyl)-; d'za and vda are chosen independently in each case from H, Si. alkyl, C1-4 haloalkyl, C1-4 alkoxy-Ci-6 alkyl, C3-6 cycloalkyl, and C3-e cycloalkyl-Ci-6 alkyl; B" is selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-Ci-e alkyl, aryl, aryl (Ci-4 alkyl)-heteroaryl and heteroaryl (C3-4 alkyl)- and benzyl, each benzyl is substituted on the aryl component with 0-1 substituents selected from C.4 alkyl, Bg, C.1, E, I, C. haloalkyl, nitro, C.4 alkoxy , C-4 haloalkoxy and dimethylamino; dza is selected from Ci-a alkyl, Ci-4 haloalkyl, Ci-4 alkoxy-Ci-4 alkyl, C3-e cycloalkyl, C3-e cycloalkyl-Ci-6 alkyl and benzyl, each benzyl is substituted on the aryl component 0-1 substituents selected from Si. alkyl, Cg, C, E, I, C-a, haloalkyl, nitro, C-4 alkoxy, C-4 haloalkoxy and dimethylamino; IN! is selected from C-4 alkyl, C-4 haloalkyl, C 1-4 alkyl, C 3-e cycloalkyl, and C 3-e cycloalkyl-C 1-6 alkyl; B" is independently selected in each case from H, C1-6 alkyl, C3-7 cycloalkyl, C3-6 cycloalkyl-C6-6 alkyl, phenyl and benzyl, each phenyl or benzyl being substituted on the aryl component by 0-3 groups selected from from C-4 alkyl, Bg, C1, E, I, C4-haloalkyl, nitro, C4-alkoxy, C4-haloalkoxy and dimethylamino; Visa is selected independently in each case from H, C1-4C alkyl, C3-7 cycloalkyl, and C3-E cycloalkyl-C1-6 alkyl; A" is selected in each case from H, C1-6 alkyl, C3-6 cycloalkyl, C3-e cycloalkyl-C1-e alkyl, C1" alkoxy-C2 alkyl, C1-4 haloalkyl, K""5(O)p-Cch- a4 alkyl and B7UATZOM-C2.4 alkyl; BZ and BZ are independently selected in each case from H, C 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 3 -E cycloalkyl -C 1 -C 6 alkyl, C 1 -C 6 alkyl -C 1 -C 2 alkyl, and C 1 -C 4 haloalkyl; as an alternative, in ME!"В"With component B"" and В!" together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from B"Z, СО2БЯ, СОВ" and 5028; alternatively, in ME""B!zB component B!75 and B together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents of choice with VZ, СО28В!", Owl! and 5028!i; Va and v'Za are independently selected in each case from H, C1-6 alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl and C1-4 haloalkyl; aryl is independently selected in each case from phenyl, naphthyl, indanyl and indenyl, each aryl being substituted with 0-5 substituents independently selected in each case from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, methylenedioxy, C 1 -4 alkoxy-C 1 -4 alkoxy . OVV, - MA"SOV'", -SHSOVl", -MA'SOMAVya, -MAZSO2VV, -MV'TV!I and -"SOMA! VZ ii to 1 phenyl, each phenyl substituent is substituted with 0-4 substituents selected from C1-C alkyl, C1-C alkoxy, Hg, C1, E, I, -CM, dimethylamino, C3, C3, CoE3, OC3, 5O2Me, and acetyl; and heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, triazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl- 5-oxide, 2,3-dihydrobenzothienyl-5 -dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl, and benzodioxane, each heteroaryl is a substituent with 0-4 carbon atoms substituted, selected independently in each case from C1-e alkyl, C3-e cycloalkyl, Bg, C1, E, I, C-4 haloalkyl, -SM, nitro, -OB!", 5H,. -5(О)тВ"8, -СОВ'", -БО28!", -ОС(О)В8, -MASOV, -SHСОВ' 2, -MA'SOMA"Vya, -"MAZSO"2В'8, - MA!VZ and -SOMVA!"В"U, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B", СО»vyaa, SOV!cha and 50281", 6. A method of treating affective disorder, anxiety, depression, headache, irritable bowel syndrome, post-traumatic stress disorder, supranuclear palsy, reduced immunity, Alzheimer's disease, gastrointestinal diseases, anorexia nervosa or other digestive disorders, alcohol withdrawal or narcotic syndrome, drug addiction, inflammatory disorders, cardiovascular or heart diseases, problems and disorders related to fertility, HIV infections (human immunodeficiency virus), hemorrhagic stress, obesity, infertility, head and spinal cord injuries, epilepsy, stroke . you My AV from v-x-y. M - B Iv) (1) or its stereoisomeric or pharmaceutically acceptable salt form, in which: A is M or C-B7; B is M or C-B8; provided that at least one of the groups A and B is M; Or is an aryl or heteroaryl group attached through an unsaturated carbon atom; X is selected from SN-VU, M-V!E, O, 5(O)n and connection; n equals 0, 1 or 2; IN! is selected from C1-10 alkyl, C1-10 alkenyl, C1-10 alkynyl, C3-z cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, C1-4 alkoxy- Sil alkyl, -502-C1-10 alkyl, -502 -812 and -5O2-B'; IN! is replaced by 0-1 substitutes selected from -СМ, -5(О)claim 8!5, -«СОвВза, -5028/13a, - MA!zaСО vza, -(СОВа) 5, - MmA'zaSOMAzadyea , "MA zaBov, "SOM zada, 1-morpholinyl, 1-piperidinyl, 1-piperazinyl, and C3-v cycloalkyl, where 0-1 carbon atoms in Ca cycloalkyl are replaced by a group selected from -O-, -5(O )p-, -МА13а-, -МСО»ВБ., - МСОВ'- and -М5О»2В/о-, and where Ma in 1-piperazinyl is substituted by 0-1 substituents selected from За, СО2В/и» , Soviet Union 50289; IN! is also substituted with 0-3 substituents independently selected in each case from B"2, B", B/E, C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, Hg, CI, E, I, Si -4 haloalkyl, -OB'Za, -"MVZad'vba and C3.v cycloalkyl, which is substituted by 0-1 BZ and in which 0-1 carbon atoms of the cycloalkyl are replaced by -O-; provided that B! is different from: (a) 3-cyclopropyl-3-methoxypropyl group; (b) unsubstituted -(alkoxy)methyl group; and (c) 1-hydroxyalkyl group; also provided that when EV! alkyl is substituted by OH, the carbon atom adjacent to the M ring is different from CH2e; B1: is aryl and is selected from phenyl, naphthyl, indanyl and indenyl, each B12 is substituted with 0-5 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, B8, C1-6, E, And, C1-4 haloalkyl, -SM, nitro, - ОВ", 5Н, -5(0)claim 8!8, -СОВ!, -ОС(О)Б8, -МAZаСОВ", -ШСОВ'», -МAZаSOMATadza , "MA zasoO"vV, "MA tad'za and - SOM ad'za; IN!" is heteroaryl and is selected from pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, indazolyl, 2,3 -dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, 2,3-dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-dioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl and benzodioxane, each heteroaryl is substituted by 0- 4 carbon atoms with a substituent chosen independently in each case from C-e alkyl, C-e cycloalkyl, Bg, C-e, E, I, C-4 haloalkyl, -CM, nitro, - ОБ, 5Н, -5(0) tV!8, -"SOV!", -OS(O)VV, -MA'zasOv!", -Ш(СОВ72, -"МAZaSOMAavza, -MVzabOgVV, "MA ad'za and - SOM ard'za, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from Ba, COg'v, Cov and 502; B!: is heterocyclyl and is a saturated or partially saturated heteroaryl, each heterocyclyl is substituted a substituent of 0-4 carbon atoms, which is chosen independently in each case from Ci-e alkyl, C3-e cycloalkyl, Bg, Si, E, I, Ca haloalkyl, -CM, nitro, ОЗа, 5Н, -5(О )0iV5, -SOV'Za, -OS(O)V5, -MA'asSOvVZa, -Щ(СОВЗа)", - MmAgasOMAZadyea, -d'zasOvViyu, -MAZadiba and -SOMAZad'ba, | each heterocyclyl is substituted on any nitrogen atom with 0-1 substituents selected from B'Za, CO', CO', and 50285, and wherein any sulfur atom is optionally mono- or dioxidized; IN? is selected from C1-4 alkyl, C3-6 cycloalkyl, C2-4 alkenyl, and C1-4 alkynyl and is substituted with 0-3 substituents selected from -CM, hydroxy, halo, and C1-4 alkoxy; alternatively, B, in the case where X is a bond, is selected from -CM, CEz, and CoEv; BAZ, B" and BZ are independently selected in each case from H, Bg, SI, E, I, -CM, C-4 alkyl, C3-1 cycloalkyl, C1-4 alkoxy, C-4 alkylthio, C-4 alkylsulfinyl, C-4 alkylsulfonyl, amino, C-4 alkylamino, (C1-4 alkyl)2g amino and phenyl, each phenyl being substituted with 0-3 groups selected from C-7 alkyl, C3-6 cycloalkyl, Bg, C1, E , I, C-4b haloalkyl, nitro, C4-alkoxy, C-4 haloalkoxy, C-4 alkylthio, C-4 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 alkylamino and (C1-6 alkyl)2 amino; provided, that when B1 is unsubstituted C1-10 alkyl, then E3 is other than substituted or unsubstituted phenyl; B3 and B" are independently selected in each case from H, C1-4 alkyl, C3-e cycloalkyl-C1-4 alkyl and C3-b cycloalkyl; B"3 is selected from H, C1-4 alkyl, C4 haloalkyl, C-4 alkoxy-C1-4 alkyl, C3-cycloalkyl, C3-e cycloalkyl-C1-6 alkyl, aryl, aryl (C1-4 alkyl)-heteroaryl and heteroaryl (C3-4 alkyl)-; d'za and v/ba are independently selected in each case from H, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-6 cycloalkyl and C3-6 cycloalkyl-C1-6 alkyl; B" is selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-cycloalkyl, C3-e cycloalkyl-Ci-e alkyl, aryl, aryl (Ci-4 alkyl)-heteroaryl and heteroaryl (C3-4 alkyl)- and benzyl, each benzyl is substituted on the aryl component with 0-1 substituents selected from C4-alkyl, Bg, C1, E, I, C1-haloalkyl, nitro, C4-alkoxy, C -4 haloalkoxy and dimethylamino; B!" is selected from Ca alkyl, C-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-b cycloalkyl, C3-e cycloalkyl-Ci-e alkyl and benzyl, each benzyl is substituted on the aryl component 0-1 substituents selected from C1-4 alkyl, B8, C1-4 haloalkyl, C1-4 haloalkyl, C1-4 haloalkyl, C1-4 haloalkyl, and dimethylamino; B5 is selected from C-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C3-- cycloalkyl and C3-e cycloalkyl-C1-6 alkyl; B" is independently selected in each case from H, C1-6 alkyl, C3-7 cycloalkyl, C3-6 cycloalkyl-C6-6 alkyl, phenyl and benzyl, each phenyl or benzyl being substituted on the aryl component by 0-3 groups selected from from C-4 alkyl, Bg, C1, E, I, C1, haloalkyl, nitro, C4-alkoxy, C4-haloalkoxy and dimethylamino; The visa is chosen independently in each case with H, C. alkyl, C3-7 cycloalkyl and C3-6 cycloalkyl-C1-6 alkyl; A" is selected in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C3-e cycloalkyl-C1-e alkyl, C1" alkoxy-C12 alkyl, C1-4 haloalkyl, B'5(O)p-Ci-a alkyl, and B!" M-C". 4 alkyl; BB and BZ are independently selected in each case from H, Ci-C alkyl, C3-O cycloalkyl, C3-C cycloalkyl-Ci-C alkyl, Ci-Alkoxy-Ci-2 alkyl and Ci-4 haloalkyl; as an alternative, in ME!"B"Z components B" and B"? together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from "З, СО28ВЯ, СОВ" and 5028; alternatively, in ME!" components "5 and B" together form 1-pyrrolidinyl, 1-morpholinyl, 1-piperidinyl or 1-piperazinyl, where Ma in 1-piperazinyl is substituted with 0-1 substituents selected from B"Z , CO2B'Ya, SOV" and 5028; Ba and b'Za are selected independently in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C3-6 cycloalkyl-C1-6 alkyl and C1-4 haloalkyl; aryl is independently selected in each case from phenyl, naphthyl, indanyl and indenyl, each aryl being substituted with 0-5 substituents independently selected in each case from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, methylenedioxy, C 1 -4 alkoxy-C 1 -4 alkoxy . OVV, - MARSOV, -SHSOV'L", -MASOMV' B, -MA"CO2B'B, -MV'B!Z and -SOMA!B": and up to 1 phenyl, each phenyl substituent is substituted with 0-4 substituents , selected from C1-C alkyl, C1-C alkoxy, Bg, C1, E, I, -CM, dimethylamino, C3, CoEv, OC3, 5O2Me, and acetyl; and heteroaryl is independently selected in each case from pyridyl, pyrimidinyl, triazinyl , furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, isoxazolyl, triazolyl, tetrazolyl, indazolyl, 2,3-dihydrobenzofuranyl, 2,3- dihydrobenzothienyl -dihydrobenzothienyl-5-oxide, 2,3-dihydrobenzothienyl-5-d ioxide, indolinyl, benzoxazolin-2-on-yl, benzodioxolanyl, and benzodioxane, each heteroaryl is a substituent with 0-4 carbon atoms substituted, selected independently in each case from C1-e alkyl, C3-e cycloalkyl, Bg, C1, E , I, C-4 haloalkyl, -SM, nitro, -OB", 5H,. -5(O)tv!8, -"SOV'", -BO028!", -OS(O)V!V, -"MASOV, -SHSOV", -"MA SOM V, -"MA"SO"V !8, -MAV'Z and -SOMV""B"U, and each heteroaryl is substituted on any nitrogen atom with 0-1 substituents selected from B", CO»vB!la, SOV!a and 50282,