SK27193A3 - Imidazopyridine derivatives, process for their preparation and their pharmaceutical compositions - Google Patents

Description

Imidazopyridine derivatives, processes for their preparation and pharmaceutical formulations based thereon.

The field of technology

The invention relates to a derivative of imidazo-pyridine, a process for the preparation and use of pharmaceutical preparations and their base.

SUMMARY OF THE INVENTION

The present invention is directed to the invention. derivatives of imidazopyridine as well as their salts of the general formula I

/ 1 /

The hydrogen atom represents a hydrogen atom or a hydrogen atom

- J represents the hydrogen atom, Hal, n in v ^ · w i i f C. * C. 1 7 Λ ^ 7 - "Ϊ · * eZ u-.y -» m *. CTIA, CINK NKA, M (A 1, NHCIF 5, NKS or 1 H-δ-t Ĺ t) · m = 7 = 3 represents hydrogen, cyalkyl, Ar-alkyl, cycloalkyl-alkyl with 3 up to S carbon atoms in the C 1 -C 6 alkyl group; - 3 " ^ VS ^ 5 * C0Η0Ϊ * -Cl-alkyl in 1c; - carbon atoms in alk * 'love - ΧςςA · ..5wi p'5 and C- *} ΓΤ V ¢ 3 Vv " 'Trans " ? 05 ^ '" * Q * ·' " * - ·; - (-) - - -? - de substituted with CODH- or C01A-; is hydrogen or Hal F. " 3 is alkyl of 1 to 6 carbon atoms each, and one or more hydrogen atoms are substituted by aro. hydrogen atom - P -: fluorine: an oxygen atom or a sulfur atom; is alkyl, alkene or alkynyl each having 6 carbon atoms; R 1 is a phenyl group which is unsubstituted but; optionally monosubstituted with a residue selected from the group consisting of Hal, N, OH, OA, COOH, COOA, CN, NO 2, NH 2,. N (O) - (NH) 2, NHSO 2 - 5 and 1K-6-tetrazolyl; represents phenyl substituted with Ar; represents a - or a six-membered heteroaromatic one with 1 to 3 nitrogen, oxygen and / or sulfur atoms, which is?  € orrorâ € ™ â € ™ â € ‹â €‹ â € ‹â €‹ â € ‹â €‹ â € ‹â € r ľ / * ^ / / t / «c ^ Giy " “* E + · > m - i · · ^ / »V * ^ V *. a / * 3 · i b WW · / '* J · «! and rt · #i V > 4 & J > A < > & J > W & It is an object of the present invention to provide novel compounds with:

j t .k ^ J r * -. * · * '? r '+ + a- ^ * ^ o * rp V * ^ w? V »« r K * »~ ^ ^ *» - *; * Ξ ·. τ - τττ ....---- /.es u *, .a ---- j * - t, —® ~ ^ --- -J ---- r · '-'--- í drugs.

It has been found that the compounds of the formula I and their salt possess valuable pharmacological properties together with door tolerability. These compounds exhibit especially the properties of a; angiotensin-II and may therefore be used as medicaments in human and veterinary medicine, in particular for prophylaxis and / or flying of cardiac, circulatory and vascular diseases. Fre dov ^ eikvm. it is the use of the treatment in which the dependence of T1, aldosteronism with cardiac insufficiency, and neurotrophic nerve sclerosis is the same. and uvperplasia of vessels and heart, anion pectoris, cardiac infarction, stroke, resterosis after angioplasty or b; / - ssps, arteriosclerosis, mlaucons, macular degeneration, peruricemia, kidney function disorders, e.g. .ia-jek, diabetic nephropathy, diabetic retirepeti?

The disorder, the disorders of the female reproductive organs of the cross-linked sinusoids, the disorders of perception, for example, daxancia, axesia, psxati disorders, states of fear, dapresis with and / or epilepsy. liato efect ss give ovarii! obvvklýir.i ma t ocami i r. vitro or ir. in vivo, as described, for example, in pater.tovorr. US SCO SO * and in 'Γ ") 9' / 'β3β7, given by J A. T. Chiu and Aalsi, J. Pharjiesco. 7XP. Tharap. 250, 867 a? 87 * / 1999 / and P. C. v'ong that? 257, 779 a? 725/1990, in vivo, in rats. w 0 T '- t and aal-

The compounds of formula (I), their salts, and the preparation of these compounds and their salts are used in the formula, wherein: a compound of formula (II) is reacted

/ II /

wherein O / H ', P.', = 'and Y are as defined in Formula I; - - - b1 sp sp t í í í í í í obecného obecného obecného obecného obecného obecného. SO1 - volytic a1a c o y d o r y ge o c t y e c t o c t o c e o o tions of their functional derivatives;

I Ψ »f» / / / al g g g g g g g g I I I I I I I va va va va Or more residues P 1, R 1, P 2, F 1 and / or Y for one or more other radicals R 1, R 2, R 4, R 4 and / or Y and / or base Or the acid of formula (I) - directs one of its radicals. salt. In the previous and next text, they have

Even if the paraneters H to R ', Y, A, Ar, Ar, Het, sy are listed in formulas I and II, they are not construed to be construed in any way in accordance with the invention. 'C ^ 31-a Λ ^ Λ ^ —G ^ ΐ £ V ^ ^ a ^ τ ^ 1 alkyl 1 1 s s s s s s s s s s s s s s ; * 1 g ·! ≫ j ^ > * - fi in J U: c: L; ±. Am; j. ^ r. c j ”idr''5'í, T-S atvl - ni - -“ --1-4- in " 1 ΐ 7λ! - .: ·. i --- '- 4- ·' -3 - * - '' ----- -. / - J --- u > à-- K. - > - i- - - wji - I - - -) —- · .- - - ^ · r 7 - - ', · - i »i · r 7« " - - - - - - - K: i -: r4 —- - 'η - n v. ... - - ^ > «&Quot; n /., ^ _ -S 0 - .9. in. e., -j -, 1 -, t - c '= -i ~ —77 = * V1 b'! 1 * · V * · 11—1 0—c " a '·' -n P? -. 7iTfl +:. ·· «ΡΛ-νΙ 1 —a -‘ v1 - τ 'λ —7? 'Vi aw " * 1—? - 0— o' -a 'il í.rä1!.:' —A - * - 7 ”1 1— '' " - 'O— OO _ O 7 mo - - - - 7 7ei i 1— -i 7 - * »· - * '· * 0 j -34i /' - | -r “at " .rl r-T " p v '1 - i + v' - 5 - T - Ť v " -Τ 'nvO 1 1 0 - c' 3I17 ', 2,2-trimethylpropyl. However, it is also possible that the alkyl or Bikines are each (= 2 to 6, preferably 2, 1 or 4) carbon atoms, in particular vinyl, 1- or 2-propenyl / allyl, 1,1-prop-2 -y1, 1-, 2- or 3-butenyl, ethynyl, 1- or 2-propyl (propargyl), 1-, 2- or 3-butynyl. Accordingly, residue 1A is preferably nonoxy, further ethoxy, propoxy, isopropoxy, butoxy, sec. butoxy, tert. butoxy, vinyl oxy, allyloxy, etinyloxy or propsryl oxy. The group COOA is preferably methoxycarbonyl or ethoxycarbonyl, further propyloxycarbonyl, isopropyloxycarbonyl, butyl oxycarbonyl, isocyloxycarbonyl, alkyloxycarbonyl and proparoxycarbonyl. The NHA group is preferably methylazone or ethylmino, NfA), preferably d: amino or diethylamino · -ethyl-

Hal is preferably fluorine, chlorine or iodine.

The radical Ar is preferably a substituted-phenyl group, preferably a fanyl group substituted in p-colohs, -VV, but the weight of the phenyl substituted in the O-substituents is C31H, COOA, and 1H-δ-tetrazolyl. Accordingly, Ar represents preferably phenyl, o-, m- or (in particular) p-pcrboxyphenyl, o-, m- or .- n -promo-oxycarbonylphenyl, o-, m- or. -ethoxycarbonylphenyl, o-, m- or (in particular) -p-nitrophenyl, o-, m-seco-1 H-τ-tetrazolyl phenyl, further preferably o-, m- or (especially) p-aminophenyl, o- , m- or / especially p -dimethylaninephenyl, m- or / especially p -diethylaminophenyl, o-, m- or p-tolyl, o-, m- or p-trifluoromethylphenyl, o-, m- or p-hydroxyphenyl, TT «* - in r-na ^ '. Vv · ® jrirl rt - n - p' or - - - ^ 0 -vn • 33r, v '; Λ - T · - ‘- ----- ---- ui - > J J “* ----- J ----- .. 1, / -,. , j. p " 1 ΐ '-. rt Γ-— ^' - 0 «. Τ »· ** 3 - T ·” - '- " ------------ < j ~ > 1— s 1 a. · 'Λ 3Γ " I Λ - ---- j. - - ------ »- j -λ - t.— c. T and r-Vi / o ^ far ·; ' - > - · r— p1 ϋ " η 7—— - - " C. " ·······················································································u - -v —1 ------ ^ a-.vl ^ _ pi a! *. P - - p.'a + OT ·· ^ rJa * * '—— TI— ¢ 1 and ^. crophenyl, o-, m- or p -acetamidophenyl, -o-, m- or p-trifluoroacetyl amophenyl, o-, m- or p-methylsulphoramidophenyl; , o-, m- or p-trifluoromethylsulfonamidophenyl. Preferably Ar is 4-biphenylyl, 2'-carboxy-4-biphenylyl, 2'-methoxycarbonyl-4-biphenylyl, 2-cyan-4-biphenyl- lyl or 2 '- (i-5-tetrazolyl) -yl-biphenylyl. 'Ja * - · i 3 r * y _j_ • is preferably 2- or 1 _ O _ p " ahT _- v- ^ ~ I) - --- v. J J y, · / -, T - 'well. f - 2- í 'and' " '0_ 1 _ 0_ / _ i - »~ a_eco o-imioazo- - Λ 75 7 Λ; 'Γ! ≪ _ '- - J -.y - i - »i: -, or 7--./- 0 _ g .3 r - 1 - or s - pyraz olyl, 2-, - or 5-isoxazolyl, 2 -, 4- or δ-thiazolyl, η-i-thiazolyl, 2-, 3- or 4-pyridyl, 2-, β- or δ- or 5-pyridinyl, further preferably 2,3-triazole- * -, -4- or -8-yl 1,2, Λ-triazole-1-, -3- to-5to-δ-γ-1,1,1,3-oxsciazol-4-one or δ-γ 1, 1,2,4-3X8 (118231-3- or -3-y 1,1,1,4-thiadiazole-2-but-00 * 0β > -j!, J4 " - 3 w j . «A ϋ 0 -“ J " c.toDi? J - j 1) yw * ru * duw. ^ S1 ^ - el ah ^ 4-rvn ·! ^ 71 .71 Γ3; 1 ^ τγ * r »o -7 -í r > r 0 - " - 7 - A - 6- or 7-benzofuryl, 2-, 3-, 4-, 5-, 5- or 7-benzothienyl, 1-, 2-, 3-, 4-; 5-, 6- weak 7-indolyl, 1-, 2-, 3-, 4-, 3-, 6-or 7-isoindolyl, 1-, 2-, 4- or 3-benzididyl olefin, 1- , 3-, 4-, 3-, 5- or 7-benzopyrazolyl, 2-, 4-, 5-, 6- or 7-benzoxazolyl, 3-, 4-, 5-, 6- or 7-benzisoxazolyl , 2-, 5-, 5- or 6- or 7-benzazolyl, 2-, 4-, 3-, 6- or 7-benzoisothiazolyl, 4-, 5-, 5- or 7-benzothiazolyl; 2,1,3-oxadiazolyl, 2-, 3-, 4-, C-7-s, and S; n -31 ir "? 1— 0— k - C._ ζ _ 7— g 1 a b O ° —i - r · ^ v. Ί t r7 _ - 7 “eT 3h5 5 - 4 · * 0-, 7- or r-quinazolyl, -2-, -3-, -5- or -7-i: 3,4-byridyl, 3K-2-, -3-, -3-, -5-, or 7-iridazo [4,3-b] -

jj, j i-j-j j j-j-j ^ c - w j j. , -J * - 4-4V /. J 7 W i-y - J -) U - P «- - 7 - - - - - - -7..4 r-p * ϊ ^ p * 7 Λ /« 1 fl -f / rvrí πνί •. ™ y .ý j “f '· * s- - * - ** -J J / - j / - / LiJ < X - —J. · &Quot; Het " it also includes homogeneous residues in which the resorbable ring is susceptible to one or more of one or two groups A, preferably not to one another and to a? M «4 I i f r * l / i oriv. © Irvλ + .yl groups. Examples of such homologous metals include 3-, 4- or 3-methyl-2-furyl, 2-, 4- or 3-methyl-3-furyl, 1,2-d-methyl-3- furyl, 3-, 4- or 3-methyl-2- (4-y-i) - * 3 uy - · w J. * -y - ^ v * -u -ny Jl y ^ ϊ ** £ - rwjv C11-18-thienyl, 2- or 3-methyl-4-pyrrolyl, -, 3-, 4- or 3-methyl-2-pyrrolyl, 3,3-dinethyl-z-ethyl 2-pyrrolyl, 2-, 4- or 3-methyl-1-imidazolyl, 4-methyl-3-cyrazolyl, 4- or 3-methyl-3-oxo-oxazolyl, 3- or 3- methyl-4-isoxazolyl, 3 'or i-methyl-δ-isoxazolyl, 3,4-dimethyl-δ-isoxazolyl, 4- or δ-retyl-2-thiazolyl, 4-or 3-. ethyl 2-thiazolyl, 2- or 3-methyl-4-thiolyl, 2- or 4-methyl-3-thiazolyl, 2,4-dimethyl-3-thiazolyl, 3-, 4- , 3-or 5-methyl-2-pyridyl, 2-, 4-, 3- or 6-methyl-3-pyridyl, 2- or 3-methyl-4-pyridyl, 4-methyl-2- pyri r. i d i η y 1, i, 6-dine ty 1--2 - pvrimidinvl, 2-, 3- or 5-hetvl-i-n '" d i. 2,6-N-N-methyl-4-pyrimidinyl, 3-, 4-, 3-, 6- or 7-methyl-2-benzofuryl, with 2-ethyl-3-benzofurinyl, 3-ethyl -2-benzotier.yl, slsbo -'.- '2 3Γ: ľ ÍľT: Íd3Z olvl T- i - JJ · _ P _ * _ ^ _ £ - p'3 »i 7« n3t «1 —P - I - t 't' »- c --- J -1-- - - '- ethyl -: - weak · ._ fz

The remainder Y is an idea of "® preferably an oxygen atom.

The radical R 'is preferably A, on the butyl group, preferably propyl, pentyl or hexyl. λ ^

The residue P 'is preferably C01H, preferably riYf-' u ΡΛ ^ ΡΛτ fw 0ι in i. / B. k c jj j ^ j w ^ ^ w j v j) ^ - ^ * ·· .λ | u · ^ · gt ^ · V: ^ ** < £ ty ^, Ό j, " 5 ^ o * T '* ^ a o ^ t Z * ·· < ~ o q «· ** - a ·' ^ T * tr ^ r λ« ^ / · », i. * - * · - —JJ 5. «- > wl ^ - 5- - -V / - - - w W V C- - ^ * .... and r * r * a ^ r. ^ c £ *. s • í-T - ^ CYO " ΐΐ * 2 r? - - _ ri: ^ _ _ n ^ r _ _ / ^ - l} _ oVa ^ -i ^ v ^ rV ^ á · w-- ^ «2 3 5 '^ - 3 4 jv —- 2' 5 ^ vi * 2'5 * r 5 ** · £ 'w-' r * ^ c ^ ^ ζ ^ · · 5 ľ ľ ľ ľ T T ľ rc- - · -v ^ ^ V® · i * «· c ^ V * r " * * ^ c1 / '” and 1 · · * - - · > - · - «- ',, ·, J · α — .a. v ./ ·· ». · ·« - - - - —w- - ** j ^ ^ o '' * - - · -— .; - 2123 0 2-phenylethyl, o-, r- or / rs jrr.a / p-ksrboxybenzyl, o-, i - λ / rp - »c / ~ - r · and * · λ vvv sn ^^ rv 'ar * '· / - »* rr _ íi: ä -s ^' ΓΡ " l'O '-» - .v. · / -.C c i .. · - / j, - - J .V / - · - . w1 x. * -i-x. ·, '- J - # i -i · ~ ^, i * «~ ς, W4X., - " - -a f v / v '/ o -'- vin in " -al "7'Γ ~ - τη— c'ia'in / * ic.?". o f r - ** 4 * r · λ ri ^ * " 17v " 1 - ~ i - o 1; 'ii / ri'TiB / γ_5γΪ »-' '' Γ'ϊΓ7ν1 T— u- c " 1 i'l i / 'r S " i aS / r-Wo: / J ... · * - mw / * »C jj. ** > - / vi ^ · *» * 4. ^^ J J | about. [beta] 1 -benzyl chloride is added. as εe cvklorrorv'n-etv1. Cyclobutyl-nyl, cyclopentyl-ethyl. cy 1 1 h h: cy 1 r. e 1, 1- or 2-cyclohexylethyl, cycloheptylretyl, cyclooctylaiethyl; Het-alkyl, such as tert-2- or 3-thienylmethyl, 1- or 2- 2-thienyl ethyl; Ar-alkenyl, such as 4-biphenylylsetyl, 2'-carboxy-4-biphenylylnistyl, 2-siethoxycarbonyl-4-biphenylylethyl, 2-ethoxycarbonyl, 1-4-biphenyl-1-propyl, 2'-cyano- biphenylthyl, ethyl, 2 '- (H-δ-tetrszolyl) -4-biphenylylmethyl; Py-CO-allyl, such as 2-oxopropyl, 2-oxobutyl,

N, N -ethyl-2-oxobutyl, 3,3-dimethyl-2-oxobutyl; Ar-C 1-6 -alkyl, such as benzoylethyl, o-, s- or p -carboxybenzoylmethyl, o-, m-or p-ret oxybenzoylbenzylimethyl, o-, r- or p-ethoxycarbonyl-benzoylmethyl , o-, r-, p-cyanobenzyltryl, o-, n- or p-n-benzoylpropyl, o-, t- or p-aminobenzoylethyl; Het-C1-alkyl, such as 2-tertiarycarbonylT: ethyl. If 1 is a hydrogen atom in the alkyl moiety of P. > then the radical (c) is preferably, for example, * -ethoxycarbonylbenzyl, * -cyclohexyl- [alpha] -; -ethoxycarbonylmethyl, 1-ethoxycarbonyl-2-phenylethyl. Ø4,5

Zwšok?. preferably represents a hydrogen atom.

P. and R " they are preferably each alkyl, such as methyl or ethyl, as well as trifluoromethyl, further preferably fluoro: methyl, difluoromethyl, pentafluoroethyl or heptafluoropropyl.

The compounds of the formula I of the knife contain one or more chelating agents and therefore the knife can be present in various active or optically active forms. and k ti n in c h - forms. • VV ec U - '• - (" n " in the formula " all these phrases. -i · · τ r r r r r r r r r r r r r r r r r r r r r r r r r r r r '- _ _ - - - - - - - - - W' '& & & & & & & & & & & & & & * · - i. * D .J: - U £ vS * w »; w-íu..viw.; W. '/ ^ / .ÍíCJíí .-. IíA'J .; * · - = - Γ * C * T * β C · ír. '7 *' · Λ3η '" P f *. Λ T Λ ^ C ^ * Λ ·· · · »^ ΛΟΠ ^ Ο ^ " Γ Ty · C ^ C Λ3ΤΜ ΤΤ “7 Λ ^ ^ Τ« * * Μ · μ V ·· J * VV ····· * »· - · - * - k > * J f ^ «·· ^ '·» ^ www *. ·, D. «Α / k V · w 4 * - ·« IV IIWV · _ _ 0 _ 0 ^ Γ *. * Γ * π & quot * ^ ^ Σ ^ S S S S S S S S S S S S S S S S S S S S S S S S S ^ λ λγ " »* -f ^ ί ^ # 3 ϋ 4k« fc - « . _ * a. «- > - —i—« f? ^ · a 'λ i'ftk · * ^ * " · * VV ».k ^ ^ w V'« V - U - ·. _ w ii; · i 5 ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii ii 1 - in / -, 'Ξ · £ 2 b? .TO [..9.Π; Liks; represents C11H, ΛΛΛΛν ΛΛΛρ »J · w y | ‘- / v j You 2 - - ^ CjNôD, NO, or e. 1H-δ-tetrszolyl; ·· r " 3-d s t c t i c - * y ¥ f · w m / ^ m. is a. | 0 JJ v ^ ·· *, 0 - ✓ fOMU Λ.Τ ^ o Ί 12 · - '1H-č- * tetrazolvl v -i / TT τ' - ~ n -iV a · u - 'hf J -Ji. . ,, -i, in the formula Z d P. represents ankvl s * w K > cheeks and 1 e: c atoms T 9 "f y Wi ·. y

-.- r, ^ «ΓΟ ',' Μ'Ο ΠΛ · ί ί · ΛΛΊΐ: 'l'l-f V .------ - in -λ ν - -. Γ.,,, -J-p-O, or O-H-tetrazolyl. Furthermore, the compounds of formula (Ie), such as 1ae, Ibe, Ice and Id, which correspond to the general formulas (I) as well as Ta, I ', Ic and Id, are preferred, and R * is hydrogen;

Tf ** í as x x ď T P T T T T T T T,,,,,,,,,,,, T,, -, -v. J. O T? ν ^ Λ-ni --‘- i answer cotr I, how ej To --9 Th tc O Td, read in them 1 i and Δ v-· r-alkyl > F ““ ““ - / / SA SA SA SA SA SA SA SA SA »» »» - - - - - - - - - - - COE I, as well as Ib, Tc and Id, in addition thereto, are the carboxybenzyl, methoxycarbonylbenzyl, cyanobenzyl, nitrobobenzyl or amobenzyl; ταν T- > - X 1 - X 1h and 1dh, which correspond to the general formulas Iaa, Ib, Ic and Id, in addition to which the following examples are given; in C 3 to C 5 atoms in the cycloalkyl-f, -C-, T-1 or tertiary amine. , which -vic ^ vacsiú '' Cícr '^ m pattern * ^ · la, Ib, Ic g A. SA, but in addition F.J imagination- i ““ Τλ " Q Ί V * “-s A r · -ii * G“ V * Λ " " 3. In the present invention, such as Het-alkyl is used; how and; la j c or. I, like C f la! C and Xi ^ nsviac v n i c ii v 1 s k R · ^ ~ t?

As well as Ar-CO-alkyl; t-.k 7 > V O * and V V f r * ó ----, - >. T'- 'Τ.Λ, -O, i'- o ^ A 7 »Q» f J ς Λ - v- | iis v läv n. - í T · -, 'Tr »- o Idl, which" "1 w, Ϊ3. -C and Id, in addition to Iba, lem and Idn, which tbt λ, - ^ ya TA neviοΛi J ii C- i T rs y * 1 Wii J A. il a 'ír, V- * · T- • á • Ά ** J 44 SJ * v, Ib, Ic and Id, in addition ij · f in them, however, RP ^ r-ads + and- in them R " Ar 1 -alkyl; “V o V - > ~ Tslr - i --- > The hydrogen atom, the benzyl, the carboxybenzyl, the nitroxycarbonylbenzyl, the cyanobenzyl, the nitrobenzyl, the benzobenzyl, the α-carboxy-β-cyclohexane, is a hydrogen atom. 1 = 1-tyl, -cyclohexyl-q (- ~ 3-xy-3-ylthyl, ethyl, phenylmethyl, 3-y-4-biphenyl-1, meth, 3-x; / p-butyl-4- biphenylsulfonic acid (1,3-dimethyl-2-oxobutyl) -1,3-dimethyl-2-oxobutyl; lao, Ibo, Ico and Ido, which are represented by the general formulas (I), (Ia, Ib, Ic and Id), in which the radical is hydrogen, benzyl, β-carboxybenzyl, ω-carboxybenzyl, β-methyl methoxycarbonylbenzyl, β-methoxycarbonylbenzyl, p-cyanobenzyl, p-nitrobenzyl, p-aminobenzyl, cis -carboxy-cyclohexylmethyl, o-cyclohexyl ω-methoxycarbonylmethyl, 2-thienylmethyl, 2-carboxymethyl, 2-thienylmethyl; 4-biphenylylmethyl, 2, 2- (ethoxycarbonyl-4-biphenyl) methyl, 2 ' - (1-etrazolyl) -biphenylmethyl or 3,3-dimethyl-2-oxobutyl. 7vl3? ΪΓ.8 ** vc B. Formulas in which Y and I and / or P. 'are hydrogen atoms

Moreover, the compounds of the formula I as well as the starting materials for their preparation can be prepared by methods known per se, such as those described in the literature, for example by standard publications such as Houber.-V / E, et al. der orgar.ischen Chemistry, »- · < o

Georg-Thieme-Verlag, Stuttgart; in particular, in 3P-A2-030C 709 and in U.S. Pat. No. 4 ESC-4, under the reaction conditions known and suitable for said reactions. There are also three known variants which are not mentioned here in detail

If desired, starting materials can also be prepared ir. so that they are not isolated from the reaction mixture, but are allowed to react directly further to form compounds of formula I.

The compounds of general formula (I) can preferably be obtained by reacting a compound of general formula (III):

In r.3Cf. j 2 / l λγ K r " --- jw * J jod al nu as a 1ky 13 'C Γ 9 d 51S VU 9 9 9 ľ ¾ 3 3 S / / / a a a a a a a a a a a a carbon atoms (preferably phenyl- or p -tolylsulfonyl) pi to. Suitably, the compound of formula (II) with a compound of formula (III) is converted by treating the first compound of formula (III) with a base at the salt, for example, by treatment with an alkali metal alkoxide such as sodium methoxide or tert. potassium butoxide in an alcohol such as methane or amide such as dinetformate (DM7) or by treatment with an alkali metal hydride such as sodium ryiride or by treatment with an alkali metal alkoxide in DMF. This sol * is allowed to react in i-i and ^ r ^ r q V · i r λ c ^ ^ λ ^ vra i. t- *; iu j. | with a compound of formula (II), conveniently at -20 ° C to 003 ° C, preferably from 0 ° C to 0 ° C. Also suitable as bases are alkali metal carbonates, such as sodium carbonate or potassium carbonate, or alkali metal hydrogen carbonates, such as alkali metal and potassium alcohols. λ c * ar ^ V i X «* fcn ^ 35 ^ rv ^ · > * · J Ä« .4 > ≪ and bb > i * 3 ^ 11 «J C« J in · · / /. wCiil and Gyt > αΙϊ ,; 5 '' J o. The starting materials, in particular those of the general formula II, are known, some of which are known in the art. The compounds of formula (III) in which P 1 'is hydrogen may be obtained, for example, by condensation of 3'-dismino-cR @ 2 -, 2-dihydro-2-oxo or - 2-thioxo-cyridine or 3,4-dia-

A mino-2-chloro-6-β-pyridine 3 carboxylic acid of the formula P1 -CDH in the presence of polyphosphoric acid. Furthermore, the compounds of the formula I are liberated from their functional derivatives by the action of solvolytic, e.g. hydrolytic or hydrogenolytic agents. - 1 2 -

Top ss " · '" The compounds of formula (I) can also be prepared from the compound of formula (I), but instead of δ-tetrazolyl groups, they contain 5-olefins which are functionally modified in the 1-position (protected by a protecting group). . Suitable protecting groups are, for example, triphenylmethyl, which is cleavable by treatment with hydrochloric acid or formic acid in an inert solvent or a mixture of solvents, for example methane or a mixture of styrene / dichloromethane / methanol / 2-cyanoethyl groups, which can be treated with sodium hydroxide in the mixture water / TI-1 'or p-nitrobenzyl, cleaving with hydrogen in the presence of Raney nickel in ethanol (see ZF-A2-C 291 969). _l. 1 ® 1 = - it is possible to convert the compounds of the formula I into other compounds of the formula I, whereby one or more of the O:

the residues P ', P., y, P. and / or Y are converted to a different radical R, H, R4 and / or Y. Thus, for example, the nitro group is reduced to a mino group, e.g. In Π 'jj_ si 9C' 3 ^ cv »'V <' i and τγ with qV · *, r or ol or ethanol and / or alternatively, the functional group or hydroxyl group or the solvol or starch is nolytically released by a functionally modified amine group and / or hydro - or a halogen atom is replaced, for example by reaction with copper cyanide, cyano and / or the nitrile group is hydrolysed to the carboxy group and / or the nitrile ring is reacted with a hydrobromic acid derivative, for example sodium azide in N-methylpyrrolidone or trimethylein house in toluene to form tetrazolyl counter.

Thus, for example, it is possible to acylate free amines by reaction with an acid chloride or a anhydride or by alkylating a free hydroxy and / or imino group by treatment with an unsubstituted or substituted alkyl halide or an N-alkyl alcohol or aldehyde , such as formaldehyde, in the presence of a reducing agent such as sodium borohydride or formic acid, conveniently in an inert solvent such as dichloromethane or THF. and / or in the presence of a base, such as triethylamine or pyridine, at a temperature of s s -1 '

If desired, it is possible, in the compounds of the formula I, to functionally and / or hydroxy function according to conventional methods by solvolysis or hydrogenolysis. Thus, for example, a compound of formula (X) which contains an NKC 'group may be converted to the corresponding compound of formula (I) which instead contains an NHg-al or COOH group. The ester groups can be saponified, for example, by treatment with sodium hydroxide or potassium hydroxide in water, a mixture of water and THF or a mixture of water and dioxane at a temperature of from 1 to 1: 3. w ·? 30SCn®!? 0 V2D27CS Tj

Γ05 Z C; “CrSC3tS7UÍ € CN or?. &Quot; is cyahalkyl, with azidic acid derivatives leading to the formation of tetrazoles of the general formula I wherein ΡΓ -s V " rs ^ àoV '! ·' 1 - ^ ^ m ·· »* ·· ϊ *. Zolyl alkyl. The reaction is preferably carried out using triazyl azide, such as triethylamine in an inert solvent, for example aromatic 3-methyl-3-one and 2-methyl-2-carbonyl ether. < hydrocarbon, axo toluene eclote 2 1 to 1

C / * p s w U ΰ L 1,! .Λ ^ Π ft 'ä ^ ¾ 5¾ », i * " / »^ ^ m m lt lt lt lt lt lt lt lt w w w w w w w w w w w w w w J J J m XVC.

* · A - 0 - > * a and ΐ -I Μη o a ~ .1 - Stitched I. u ï C. C. j V U. 3 ant λ · ant ant V * λ τ · '' ^ ίλ n T ^ ^ λ V ·· '< «WA * w • nJ / 6 J 1 to · A 0W MA JJ Ä AV by reaction with kvs eiinam in A r? for the appropriate acid addition salts. In particular, acids which give physiologically acceptable salts are suitable. Thus, for example, inorganic acids such as hydrochloric acid or hydrobromic acid, phosphoric acids such as orthophosphoric acid amidosulfonic acid can be used. Furthermore, organic acids, in particular aliphatic, alicyclic, arsiphatic, aromatic or heterocyclic, mono- or polybasic carboxylic or sulfonic acids or acid-derived acids for the isolation and / or purification of sulfuric acid compounds c and I., e.g. propionic acid, pivalic acid, diethylacetic acid, malonic acid, succinic acid, pimelic acid fumaric acid, maleic acid, lactic acid, tartaric acid, malic acid, citric acid, glonic acid, ascorbic acid, nicotinic acid , iso-nicotinic acid, methane or ethanesulfonic acid, ethic disulfonic acid, 2-hydroxyethanesulfonic acid, benzene sulfonic acid, p-toluenesulfonic acid, naphthalic-mono and disulfonic acid, and lauryl sulfonic acid. Acid salts which are not physiologically suitable, for example picrates, can be used

The second page ^ 9 can ^ " 'account', " '"

- which contain a carboxy group or a tetrazolyl group for the conversion of a carboxy group or a tetrazolyl group. 2'JJ. 3 | ^ " T * '* Vj ^ P - ** ^ «r; ^ ^ Q T *. TT glifoxide or sodium or potassium carbonate, or the corresponding salts with metals, in particular alkaline or alkaline earth metals, or the corresponding ammonium salts. Another solism is preferred. ; λγ-

The novel compounds of the formula I and their physiologically acceptable salts are used for the preparation of pharmaceutical preparations. In this context, these compounds are treated together with at least 21SCUC9 carrier or excipient and; together with one or more additional active ingredients to a suitable dosage form. The preparations thus obtained can be used as medicaments in human or veterinary medicine. Suitable carriers are organic or inorganic substances which are suitable for oral administration or oral or rectal administration or parenteral administration or administration in the form of inhalation and which do not react with the novel compounds of the invention. . Such carriers are, for example, water, vegetable oils, alcohols, polyethylene glycol, glycerol triacetate and fatty acid fatty acids, gelatin, soybean lecithin, carbohydrate, such as lactose, weak starches, stearar. hoTrick, ma?; so weak r * a ^ ^ > > 7c Λ «ό1« «a and i ^« ί? r r t tn c c t cM atv λ r »Q 7 Å

w. · M M A A w w it it it it it w w w VA VA VA VA VA VA 4 4 4 4 4 | · ≫ In W «* ^ La w W W W W j j j V V V V V V le le le le le le le le le le le le le le le le le le le le le le; attention should be paid especially to coated tablets and capsules with coatings or lenses resistant to gastric juices. The rectal administration is provided by lace, for parenteral administration, solutions, in particular oily or aqueous solutions, ingested suspensions, emulsions or immaculatates. Fre application in the form of inhalation sprays can be used with sprays containing the active ingredient either disentangled or suspended in a propellant or propellant mixture (such as hydrocarbons such as propane or butane or fluorinated hydrocarbons such as heptafluoropropane). In doing so, the active substance is - * 3. V ^ λ -? ? Λ "VT c - - ™ r.3a · 7 7 * 7 7 n" r- r * '?! One or more additional physiologically acceptable solvents, for example ethanol. Inhalation solutions can be applied with ^ v ^ 1 · " - r’rc1 ť * - > t * £ 71 1 τ ^ and v * i? T " rr.c " Δ * · a - ^ · < / - · - v '-------- ·· - »* w / · - •• j - * U. For example, the preparations can be sterilized and / or the knife contains excipients, such as preservatives or stabilizers and / or blenders, emulsifiers, salts for the preparation of injectable preparations. adjusting osmotic pressure, buffers, dyes C / C ^ and ^ ^ O Τ '" *) i-17 c' T ^ · Λ * τ ry · * 3 ^ ^ X · 7 ^ ^ ^ 7I · '^ Λ · Ï / Cti jlus ~ .ícíwi.c - i v. r ^ v · rvA j d i. The compounds of the present invention contain one or more other active ingredients, for example one or more vitamins, the diuretics and the active ingredients. Generally, similarly to other known commercially available formulations, the invention may be administered, in particular with about 1 mg to 1 g of U3-S6C, as described in U.S. Pat. up to 50C mg ~ - V Λ. J V 5- - · - * ^ - W.T. ^ ·

Preferably, the daily dose is between about C, 1 and 100 and / kg, in particular 1 and 50 mg / kg of body weight. However, the specific dose for a patient depends on a variety of factors, such as the efficacy of a particular compound, age, body weight, and overall health: patient status, sex, diet, time and portions of vision, excretion rates , on the combination of drugs and the severity of the disease that is being treated. In the following examples, the term " conventional processing "

If water is desired, depending on the nature of the final product, the pH is optionally adjusted to 2 to 1C, the ethylation phase is then extracted, and the residue is purified by chromatography on silica gel or crystallisation or ^ ~ ^ »O * S ** ΟΤΙ j < ? Í 5 5 > And the remainder

CLOUT. “V * cVfira” • v. · Ρ *. ^ · · W * c β ^ · • ·. - W r.Cl.v W ... JAmC «. - / Xi. I. W. *. 7, w · i * / »b as used: with ethyl acetate / netanol, 9 DO! represents -4,5-dihydro-1-oxo-1H-imidazole; , 5-a. - 7-

EXAMPLE 1: 19.1 g of 2-butyl-4,5-dihydro-4-oxo-1 H or imidazo [4,5-c] pyridine (m.p. 2S5) are dissolved. 2903C, which can be obtained by heating 3,4-diathino-2-chloropyri- dine and polyacrylic acid in polyphosphoric acid first at 100 to 50 ° C with a temperature of 170 to 18 ° C / ° C. DM7 ml. The solution is mixed with 15.5 g of potassium carbonate and stirred for 6 minutes. d, dropwise a solution of 27, i; g retylester tor. the mixture

Lvl ro ΟΓΟΪΙ1 ”? Vír I.flV S Zľľ 9 3 S £ lT. ^ 3 ^ 3 '6 3 3 w ^ j ^ 3

ΛΛ - f. i SS - - - - - - - - - - - - - - - - - - - - - - - - - - - Z Z Z Z Z. VB VB VB VB VB VB VB VB VB VB VB VB VB ec ec ec J J J J J J J J J....... - A. 3 £ w ... .. 'ä. d-4i. The use of stylacezate and the mixture of ethyl acetate and f = is obtained first with 2-butyl- cis- p -tethoxycarbonyloenzyl-DDI having a melting point of 1 24 ° C and a rotary phase of 2-butyl-1-carboxamide. to xykarb o-

≫ ~ 4 «_ £ - 1 ^ ·«. I ka C Ολ ς. c - r ^ -

Similarly, by reacting p-bromoethylsulfurate, tert-3, 6-bis-β-cyanobenzyl-d1 is obtained with a melting point of 122.5 tyl-3-β-cyanobenzyl-301 having a melting point of 2C TOC.

Similarly, from 4 ' -dihydro-4-O-O-2-propyl-1 / B / H-imidazo [4 ' -c] pyridine (m.p. 25-3C); which can be obtained from 3,4-dimino-2-chloropyridine and butyric acid in the polyphosphoric acid to yield 7.5-isopropyl-methanesulfonate. 2-cropyl-DDI / oil; P 1 C 1 1 1 in ethyl acetate / and 3-fluoro: cyclohexyl λ '*, ar-r in " 1 ". - Tir > ^ - vr ~ - ΉΌ " T - ‘and - l - > * a * -n - i s / 'Ιϊ-' · '1 • J -« -. / - -; ·. '-'. . _ _ r. - J. ' .

Example

Similarly to Example 1, 2-butyl-5 - (* - cyclohexyl-cyclohexyl-3-yl-DDI) which can be obtained by benzylating 2-butyl-4, 6-dihydro-4-oxo- 1 (or 3) H-isothiazole-4,5-c-pyridine to give 3-bromo-1-H-2'-compounds which can be reacted with the acid ester ester of < 1 > -bromo-cyclohexyl-2-butyl-3-bromo-1- (5- (* -cyclohexyl- (n-methoxycarbonyl-1-yl) -JH, from which the benzyl group cleaves from the hydrocarbonyl group) and p-bromo-isatyl-benzoic acid methyl ester obtain 2-butyl-5- (α-butyl-hexyl) -butoxycarbonyl-ethyl-3-methyl-oxycarbonylamino-benzoic acid; -DOI, Pf 0.63, rc, iq - i - - - c c. * ≫ * • 1 · W i. of solution 3 - 29 & 2-buty1-3-z-ethoxylate: m.p. 218-293 ° C in 5 ° C: 1 ° C. X X ^ j j j j '' '' '' '' '' '' '«« «. w »« 4 < n *. 3 c i j: il_ ii «*. * l. - b. thi j - - - / * - £. w ^ j w b. v - 2C b. -L -t u. - - »J. Enz i enz enz,,,,, ** ** ** ** ** ** ** ** ** ** ** ** ** ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^. BWV " ' orr 7 - V ^ i J fm -3 n ^ * 70 r ť b * f ^ r% ·· «μ / V * < ρ »a / M - f

you 7 ^ Λ Λ ^ 'f' «/ .Sb > w C Tm K, sA, 's s ^ m ern' · -butvl-3 v _ r * - * raw / U. - Λ 0 b ensvl-DOI O t melting point! · + Imm W F'íí " 50Π9 S9 7. 2 " 9 Γ-y T " u 9 " t V1 ^ Τ '' > r c V C ~ - -3 --- -or xy k a r b o n y1b en zy1-ô- (2-1 i a ny1me ty1) -201,

Similarly, 2-butyl-6-cyclohexyl-o-oxo-3-carbonyl is obtained from methyl-.beta.-bromo-.alpha.-clonexylacetic acid. b enzyme 1 -DO I, f 0.63.

Similarly, 2-methylpyrrolidone is obtained from 3-methylpyrrolidone-3-propylbenzene in 3; 1 - [(6-methoxycarbonylbenzyl-DOI, P.f. C, 47] using ethyl acetate / nexane 9: 1).

Similarly, 2-butyl-3-p-oxoxycarbonyls of 1-O- (methoxy-3-hydroxybenzyl) -propionic acid is obtained from 2-bromo-3-ferropropyl-propionic acid. -2-phenylethyl-JOI, Rf 0.64. Τϊ - A ^ s s - - y i i λ λ λ c c c c i i i i i i i ^ ^ 0 ^ 77 "- 7 - * ** ^ mf Ί _« > '* ^ Jli_ í ;. w o - JJ ··· J w · - J w ·· * · - ** > »Y ** - - · OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ OZ -D-D; o-p-nitro-benzenes 1 - 7 - p - methoxycarbones 1 - 2 - pro - 1 - D 91 ε 5- (1,3 - di - naphthyl) 2 - oxo - hutyl) - 3 - cethoxycarbonylbenzyl -2-propyl-DDI.

Similarly, from 2-butyl-3-p-acidbenzyl-N-4-bromomethyl-biphanyl-2-carboxylic acid ethyl ester, 2-butyl-3-benzoylbenzyls are obtained. 1 bi ery 1 y 1-4 - xety 1) -DDI o -o. terlote spin 55 C.

Fez oona sa z 2 - b u i y 1 -1 - o - a n b 9 r. z y 1 - ZO I s c] j · '2j ^ e 2 - * 3' JI * t V - C ^ lT '/ S.r.b: 5Π3Τ' 1 - ^

Γ.ΛΓ, * O 07 ^; To a solution of 3 g of 2-butynyl-4,5-dihydro-4-ox 3-1-ol in 3 ml of H-midazo [4,5-c] pyridine in 73 ml. A solution of 0.4 g of sodium in 10 ml of non-alcohol was added dropwise at 20 ° C. In t - 5? Í nr " '' o r ^ Vwc ^ M-la 3j * í * - τ ': —.τ' · * r · - * -v τ c c > - < τ * -. V λ · ff Tff- * »* k ·» · - > J. «4 M wVp · à '"' ·· * C * SA ^ ·. #. 'k - ·' / * j w A ** ** 1 w < «* v w '_ L v tk J _ |

The residue was dissolved in 30 µl of H 2 F and cooled to C ° C. A solution of 3.7 g of p-bromobenzoyl bromide is added to this solution and the mixture is stirred at room temperature for 15 hours, then evaporated. The usual work-up and chromatography on silica gel with ethyl acetate / toluene 7: 3 gave firstly 2-3 parts of a solid (DDI), m.p. 2 - b u t y 1 - 3 - p - r i t r o b e r. of Y-D-I having a melting point of 193 to 19 ° C. - PC - 2. e - melting 55 5? to 5 ° C. 1 g of 2-butyl-3-p-methoxylcarbonyl-1-5-p-nitro-benzyl-D is dissolved. in 50 ml of methanol. The solution obtained is subjected to hydrogenation at 2 ° C and 1 µl F in the presence of 0.5 g of 5% palladium on charcoal until the absorption of hydrogen is complete. The catalyst is then filtered off and the filtrate is evaporated. The residue was chromatographed on silica gel eluting with ethyl acetate: hexane 9: 1 to give 5-p-aninobenzyl-2-butyl-3-p-ethoxy-carboxymethylbenzyl-DOI at a temperature of about 1: 1. kt three Mixture 1 g CM ** ”- J r Ti CT 0 tt J 2.) c. X ^ 1 N hydroxi is m.a * and hours cri hours at 2C‘C. The mixture is then acidified with hydrochloric acid. After the usual processing, 2-bu- • f 1 β T e - Ve v ·, f * λ r * 'T r ^ e ^ - - t " »* M Τ ^' Λ ^ ^ y -, j w . ä L ·, i. .J - y f * ·. -. - - - · i «äj v * - - * v« * * 7 0 • i in W #

Similar to saponification. the corresponding methyl esters obtain the following ΓΟΙ: 5 - p - aminobenzy - 1 - 2 - buty - 3 - p - carbo: 1 -, 1 -, o temperature of 130 ° C: 2 - butyl -, - p-carboxybenzyl-, o taplota of topical 249-2-butyl-3,5-bis-β-carboxybaryl, melting point 15CDC; 3 - p - k a r b o x y b a n z y 1 - £ - p r o p y 1 -, o melting point 239 C; 3,5-bis-β-carboxybaryl-2-propyl, mp 209 ° C; 5-benzyl-3-p-carboxybenzyl-2-butyl-, m.p. in the form of a potassium salt, with a melting point above 30 ° C; 2121 L * -1-β-carboxycarbonyl-5-β-tert -benzyl-2-propyl-, 3 melting point 3003C; 2-Butyl-3-p-carboxybenzyl-5- (2-thienylmethyl) -, at a temperature of about? n 1 ^ Λ. 3- p -carboxybanzyl-5- (3,3-dimethyl-2-oxobutyl) -2-propyl- melting point 195 ° C; 2-butyl-3-p-carboxybenzyl-5-one; -carboxy- [eta] < 5 > -cyclonexylmethyl-, m.p. 195 [deg.] C .; 2-butyl-3-p-carboxybenzyl-5-carboxy-benzyl, in the form of sesquihydrate, mp 234 ° C and r > t.ac- 2 - b u t y 1 - 3 - p - pc rb 3 x y e 1 - 5 - (1-carboxy-2-phenylethyl) -, o

7 t v'ir.í Q i J c c. The product yields 2-butyl-3-n-carbamoylbenzyl- (2-ynyl-4-piethyl) -benzyl. about the temperature of spin 2i1 o.-

EXAMPLE 7 t-Cl-Cl. ΐΐ »a * * * * 4 4 4 * * * * * * * * * * * * * * * o o o o o o Metz

»» »^ ^ ^ · S S S S S S S S S S S S S f f f f f f f f f f f f f. .2 si v 0 p -

* * K * C

A mixture of 4.21 g of 2-butyl-3,5-bis-p-cyanobenzyl-DOI, 41.2 g of tertiary tin and 30 ml of toluene was boiled for 72 hours and then evaporated. The residue was stirred at 20 ° C for 2 hours with an ICC of methanolic hydrochloric acid. The usual treatment using a mixture of saturated sodium chloride solution and dichloromethane yields 2-butyl-3,5-bis (β- (β-5-tetrazolyl) benzyl-10-ol having a melting point of 2-23C. - 22 - ~ s * _ in V · * β τίΗ and »· '» ·'! «T} '") T 7 ι # ζ Vo _ * JUV Ji.í 3 w - ^ ujr _, y ÍW. ≫ 1 i ím -. and t-. §Y. + J J ± 1. X o Γ. G 3 - (C 3 -) - (p- (H-δ-tetrazolyl) benzyl) -DOI. me

The image e is from 2 - b u t v 1 - 3 - p and a r. b = nzy 1 - 5 - 2 2 * - methoxylcarbonylamino-4-methyl) -DO1 obtains 2-butyl-δ- (2'-ethoxycarbonylbiphenyl) 1'-methyl) -3'- (1 H-δ-tetrazolyl) benzyl) -D: O is the melting point of 1-43 C.

Similarly, 2-butyl-3-p-benzyl-5-cyanomethyl-1-DOI gives 2-butyl-3- (p- (1H-δ-tetrazolyl) benzyl) -1H- (1H) -O-tetrazolylmethyl) -DOI, m.p. 26 DEG C. (with decomposition). l). * r1

The following non-limiting examples refer to pharmaceutical metals which contain a compound of the formula I or a salt thereof as an active ingredient.

Usually with tablets, tablets are grown; the composition that can be - if n OK í * ^ 2 CG CG i * C i ... C · Λ j U. i.Ci «JJ -t S ϋ w.; C > J fcj is desirable - c- Λ ^ ^ Λ úl w i. The active ingredient of the general formula (I-11) is coated with cellulose 278.8 mg lactose 10 mg / maize starch 11 mg stearar. ho y y y ~ y ~ v ** orr ·. ^ · + * V " λ r * “r * ^ 7 τ '* · * ·.« · v, e. j »w - ·· * · '* · · v 0? EXAMPLE S Hard gelatin capsules

Typically, the two-piece hard gelatin capsule is filled with each cartridge. of this composition

Uľinná ľ. ó t pieces of general formula T 150 .sk .sk t z óza cellulose magnesium stearate *? ς * · »· ✓ w - '5 Example 5 / Lakka gelatin capsules Λ U * · · · ^ " rj 7 .íl Ci * * " ΛΛss V ’fs'ss a aΛΛΛΛΛΛΛΛΛΛΛΛΛΛΛΛΛΛΛΛ W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W Wiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaia · - U .j '-J 3 contains 50 mg of a release agent = onvovsm ι a-p - - L,?? r 1 to -3 U T U £ ττ τ τ:: c flow 200 ~, a ^ ra ·; * 4 * Ä. Ui.iii-sj - - - in 2 kg 1, 2-prose oco to «.η i · * r .- * i o1 u_ _ i * .. .7 v» i. * T? IT: s 3-t. clr.is sniru Ληςρ ^ ΐ ’“ * 3 P? nn?? ; '^ Ί r > ^ a' í 1 ·.?. + V · *? ta · / U -rf 4. ····· · y —- - »wA ^ · (t • o r

Scented suscanzia re-oral acliksciu

They usually prepare both *. cia unit / ml ml / contains ICO mg / ^ T 7 / " o * " * V * " * ^ ^ f ^ * " j--/ / / - / C1 j j j j j j j j j j j j j j j U U U U U r 'a? - J '- 4 - with: Ή »T? e λ v '' U U * Ä. w «_ ^ w« Λ ·

Claims (5)

P A - N 1 Y. Y F \ t where 4 R 1 O TJ r or A; Vg1 OR —c-1 - " J * > A ΠΛΛ * · ΡΛΛΑ V--) - J λ " j v. | or Het-C 3 -alkyl always having up to 5 carbon atoms in alkyl-C 1-6 alkyl; 3 moieties wherein one hydrogen atom in the alkyl moiety is optionally substituted with C 11 H- or COOA-; -.4 «< 4% ΛO 'represents hydrogen or Hal; R " water is alkyl of 1 to 6 carbon atoms, with one or more hydrogen atoms being optionally substituted with fluorine atoms; it represents an oxygen atom or a sulfur atom; represents alkyl, alkenyl or alkynyl with up to 6 mV * " 1-fVe · s- .. - .- k- - * · · - < tb > C Λ Λ ΤΤ »O O O O et kv et et et et et et et et et et et et et et et predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje predstavuje et et '' '',,,,,, , CHA, CN, NO, ττ, NHA, N, O, NHC, R, NH, R, and K-δ-tetrazolyl; Ar " is phenyl substituted with Ar; The hat is a six-membered heteroaronatic ring with 1 and 1 nitrogen, oxygen and / or sulfur atoms, optionally attached to the mine or pyridine ring, and the sludge is a fluorine, chlorine, bromine or iodine atom 2. Imidazopyridine derivatives of the group consisting of: 2-butyl-benzyl-3-p-carboxybenzyl-4,5-dihydro-4-oxo-imidzo [4,5-c] pyridine and its salts; / 2 - hli * v? - 7 - · “- In • 'h3W * · 1 ar * 1 - o. - ~ c, - n τ 'ov- * " ·' o * '·· * ** - - -' 'j /' '' '' •• “u - 'V - w' ~ * * 1 / - - * In -y · | '' • '" i / a w ^ - L - ^ V ^ - " Í -. í r ^ β " λ / i; * - λ / -v ^ · 5 ^ ^ ô “3 > - c - ^ - - - > _ / * · “J / - - - - * · - w - * - - - - " 5 * τ '- Vo w h or * 7 wil ~ ^ trH r * " γ —--------- -------- )ΛΛ · ---- ^ ^ ^, 4-oxo-3H-imilazo / 4,5-o-cyridine and its salts. 3. A process for the preparation of imidazopyridine derivatives as well as their salts of the general formula I according to claim 1, characterized in that the compound of the formula II E-t-i is reacted. (11) wherein the reactive is chlorine, bromine, n is operably modified iodine or free or xy group s is as defined in formula I - III - with III - formula III Wherein R 1, R 2, R 1, R 1 and Y are as defined in formula I; or that the compound of formula (I) is liberated by the action of a sol-volytic or hydrophilic agent from its functional derivatives: and / or that one TJ / la / or Y is changed in the compound of formula (I) per day but- 0 O-- J. *? Λ and / or Y a / c 1 n ^ s. ^ w > o re l C C C C C C - - J J J J J J J - - - - - - - - - - - - ____56! ▼ * >. 'T! Or more other residues P: f F ', ru from their salts. Pharmaceutical Manufacturing of a Pharmaceutical Formulation; and / or one of the physiologically acceptable acid addition salts thereof together with at least one solid, liquid or semi-liquid carrier or excipient. to a suitable dosage form. 5. Pharmaceutical preparation, m.p. , v v ξ π ε X -i - /. - α «- - c i take one fuse er.inu general h o formula T or t from their fyzole o j? c c suitable acid addition salts. 7. Fusion of the compounds of formula (T) according to claim 1 and / or their physiologically acceptable addition salts with T'-T'r - - TV - / v «Z-uoer.inv ^ jffriqr λ ^ η ^ 5. A process for the preparation of a medicament for the preparation of a suitable salt with creoic acid can be used.