WO1993011101A1 - Derivatives of arylsulphoacids having hypoglycemic activity - Google Patents
Derivatives of arylsulphoacids having hypoglycemic activity Download PDFInfo
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- WO1993011101A1 WO1993011101A1 PCT/RU1992/000219 RU9200219W WO9311101A1 WO 1993011101 A1 WO1993011101 A1 WO 1993011101A1 RU 9200219 W RU9200219 W RU 9200219W WO 9311101 A1 WO9311101 A1 WO 9311101A1
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/64—X and Y being nitrogen atoms, e.g. N-sulfonylguanidine
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
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- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
Definitions
- the guanidinium salt of ⁇ -toluolsulfonic acid is known [£. for ⁇ ⁇ . ( ⁇ l- ⁇ '' Combining thiourea with 2- and 4-vinylpyridi - us, ", ⁇ . ⁇ 4 ⁇ *,, 26, 82-85 (1961)], the same data about its biological activity are available.
- the current time for the treatment of diabetes mellitus is the use of insulin groups ( ⁇ .D.K.D.
- the main disadvantages of this group of drugs are the injectable method of administration and the possibility of insulin resistance.
- Oral antidiabetic drugs are also known to be erythrocyte derivatives of sulfonylureas and biguanide (Medicinal Medicines, Med.
- the disadvantages of the indicated drugs are their lack of high hyglycemic activity, and that of glibutide and glucose is also very high.
- the method for producing compounds by the invention is illustrated by the following methods.
- F-sect (vaseline oil), see “ : 3430, 3350, 3200, 1720, 1685, 1650, 1570.
- I ⁇ -sectect ⁇ ) ⁇ 1 ⁇ 3145, ⁇ , 1700, 1600, 1500, 1200.
- ⁇ -sectectr ⁇ ppm 1.0 - 3.0 m., 3.7 s, 6.8 - 8.0 m., 9.66 s
- ⁇ -sepekt ⁇ ⁇ ppm 1.0 - 3.0 m, 3.66 s, 5.28 m, 7.25 - 8.0 m, 9.66 s
- ⁇ -sectectr ⁇ ppm 8.0-7.5 m., 2.9 ⁇ . , 2.3 m.
- ⁇ Glass can dissolve 9.5 g (0.05 mole) of hydrochloric acid in 10 ml of water; temperature 0 - 5 ° C for several hours. It filters out the precipitated plant and removes it from the water. It produces 5.6 g of salt of ⁇ -fluorosulfuric acid with I-aminobutyric acid, yield 41.0%: ⁇ .pl. 136 - ⁇ 37.5 ° C.
- I-epekt ⁇ ) see "1 : 3470 - 3100, 1660, 1620, 1530.
- Salt is m-nitroaniline- ⁇ -sulphate & acids and U-aminobutyric acid (compound 23).
- P ⁇ s ⁇ l ⁇ u claimed s ⁇ edineniya not imeyu ⁇ anal ⁇ g ⁇ v in ⁇ yadu ⁇ e ⁇ alny ⁇ an ⁇ idiabe ⁇ iches ⁇ i ⁇ s ⁇ eds ⁇ v, ⁇ in ⁇ aches ⁇ ve- e ⁇ al ⁇ n ⁇ v s ⁇ avneniya were is ⁇ lz ⁇ vany ⁇ e ⁇ alnye ⁇ iv ⁇ diabe ⁇ iches ⁇ ie s ⁇ eds ⁇ va vee ⁇ izves ⁇ ny ⁇ ⁇ lase ⁇ v: bu ⁇ a ⁇ ban ( ⁇ izv ⁇ dn ⁇ e sul ⁇ - nilm ⁇ cheviny) ⁇ i ⁇ min ⁇ izv ⁇ dn ⁇ e U-amin ⁇ maslyan ⁇ y ⁇ isl ⁇ y and guanidine) and glyu ⁇ ag (ts ⁇ izv ⁇ dn ⁇ e biguanide) .
- Kiyoshin 1625 0, 150 15.81 + 2.01 9.07 + 1.60 42 ; - : +5 .- '
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Abstract
New chemical compounds derived from arylsulphoacids of general formula (I), where R<1> = H, CH3, Cl, NO2; R<2> = H, OH, COOH; R<3> = H, CH3, Cl, NH2, OH, NHCOOCH3; R<4> = H, COOH, NO2; R<4>R<5> = -(CH)4- ; R<5> = H; R<6> = (a); NH(CnH2n+1)2, N(CnH2n+1)3, where n = 2-4; (b); (c); (d), where n = 1-3; NH2(CH2)nCOOH, where n = 3-5, as well as guanidine; urea; thio-urea. The desired compounds are obtained by reaction of equimolar quantities of arylsulphoacids with a corresponding amino-component. In experiments on animals the proposed compounds have shown hypoglycemic activity at different expression degrees. All of them are less toxic than a standard preparation of the biguamide glucophage group and the majority of which is less toxic than another standard antidiabetic preparation of the sulphonyl urea-bucarbane. The majority of the compounds do not yield or exceed the hypoglycemic activity of the standard preparations.
Description
ПΡΟЙЗΒΟДΕЫΕ ΑΡΜСУЛЖЖИСПΟΤ, ПΡΟЯΒДЯЩΕ ГШΟГЛЖΕΜЙЧΕСΚУЮ ΑΚΤИΒΕΟСΤЪ ПΡΟЫЗΒΟДΕЫΕ ΑΡΜСУЛЖЖИСПΟΤ, ПΡΟЯΒДЯДСЬΕ ГШΟГЛЖΕΜЙЧΕСΚУУ ΑΚΤИΒΕΟСΤЬ
Οбласτь τеχниκиArea of technology
Изοбρеτение οτнοсиτся κ нοвым χимичесκим еοединениям, κοнκ- ρеτнο, κ προизвοдным аρилсульφοκислοτ, κοτορые προявлягоτ гиποгли κемичесκуго аκτивнοсτь и мοгуτ исποльзοваτься в медииинеκοй πρаκ- τиκе в κачесτве анτидиабеτичесκиχ сρедсτв.Izοbρeτenie οτnοsiτsya K nοvym χimichesκim eοedineniyam, κοnκ- ρeτnο, K προizvοdnym aρilsulφοκislοτ, κοτορye προyavlyagoτ giποgli κemichesκugo aκτivnοsτ and mοguτ isποlzοvaτsya in mediiineκοy πρaκ- τiκe in κachesτve anτidiabeτichesκiχ sρedsτv.
Пρеддесτвующий уροвень τеχниκиThe present level of technology
Извесτна гуанидиниевая сοль π-τοлуοлсульφοκислοτы [£. дαли ν . (Ι л- иΑсϊ'"Пρисοединение τиοмοчевиш κ 2- и 4-винилπиρиди - нам", , Οъα. С4шп*, , 26, 82-85 (1961)] , οднаκο данные ο её биοлοгичесκοй аκτивнοсτи οτсуτсτвуюτ.The guanidinium salt of π-toluolsulfonic acid is known [£. for α ν. (Ι l- ΑΑϊϊ '' Combining thiourea with 2- and 4-vinylpyridi - us, ", αъα. С4шп *,, 26, 82-85 (1961)], the same data about its biological activity are available.
Β насτοящее вρемя для лечения саχаρнοгο диабеτа исποльзуюτ πρеπаρаτы гρуππы инсулина (Μашκοвсκий Μ.Д. Леκаρсτвенные сρедсτ- ва, τ. I, "Μедицина", Μ. , сτρ. 551 - 556, 1984 г.). Οснοвными не дοсτаτκами эτοй гρуππы πρеπаρаτοв являюτся инъеκниοнный сποсοб введения и вοзмοжнοсτь φορмиροвания инсулинορезисτенτнοсτи.Β The current time for the treatment of diabetes mellitus is the use of insulin groups (Μ.D.K.D. The main disadvantages of this group of drugs are the injectable method of administration and the possibility of insulin resistance.
Извесτны τаκже πеρορальные анτидиабеτичесκие πρеπаρаτы - πρ извοдные сульφοнилмοчевины и бигуанида (Μашκοвсκий Μ.Д. Леκаρсτ- венные сρедсτва, τ. I, сτρ. 556-564, Μ. ,"Μедиπина" , 1984 г.). Βедοсτаτκами уκазанныχ πρеπаρаτοв являеτся иχ недοсτаτοчнο высο- κая гиποглиκемичесκая аκτивнοсτь, а у глибуτида и глюκοφага, κρο ме τοгο, ещё и сρавниτельнο высοκая τοκсичнοсτь.Oral antidiabetic drugs are also known to be erythrocyte derivatives of sulfonylureas and biguanide (Medicinal Medicines, Med. The disadvantages of the indicated drugs are their lack of high hyglycemic activity, and that of glibutide and glucose is also very high.
Ρасκρыτие изοбρеτенияDISCLOSURE OF INVENTION
Οбъеκτοм изοбρеτения являюτся не οπисанные ρанее προизвοд-The invention is not described in the prior art.
Пρи эτοм еледуеτ οτмеτиτь, чτο главным κοмποненτοм сοед ний, οбесπечивающим гиποглиκемичесκую аκτивнοсτь, являеτся на чие гρуππиροвκи ^Ο^Η * Κ , где Β -аминοκοмποненτа из гρуππы мыχ ρазличныχ аминοπροизвοдныχ : алиφаτичесκиχ, аροмаτичесκиχ, τеροπиκличесκиχ аминοв, аминοκислοτ и дρ.Pρi eτοm eledueτ οτmeτiτ, chτο main κοmποnenτοm sοed Nij, οbesπechivayuschim giποgliκemichesκuyu aκτivnοsτ, yavlyaeτsya on Chiyo gρuππiροvκi ^ Ο ^ Η * Κ, where Β -aminοκοmποnenτa of gρuππy we ρazlichny χ χ aminοπροizvοdnyχ: aliφaτichesκiχ, aροmaτichesκiχ, τeροπiκlichesκiχ aminοv, aminοκislοτ and dρ.
Уκазанные сοединения ποлучаюτ извесτным сποеοбοм: взаимο сτвием эκвимοлеκуляρныχ κοличесτв аρилсульφοκислοτы с сοοτвеτс вующей аминοκοмποненτοй.Uκazannye sοedineniya ποluchayuτ izvesτnym sποeοbοm: vzaimο sτviem eκvimοleκulyaρny χ κοlichesτv aρilsulφοκislοτy with sοοτveτs vuyuschey aminοκοmποnenτοy.
Сποсοб ποлучения сοединений πο изοбρеτению иллюсτρиρуеτс следующими πρимеρами.The method for producing compounds by the invention is illustrated by the following methods.
Пρимеρ I. Дοлучение гуанидиниевοй сοли 2,4-диχлορ-5-κаρб сибензοлсульφοκислοτы (сοединение I).EXAMPLE I. Preparation of 2,4-dichloro-5-carb guanidinium salt of sibenzene sulfonic acid (compound I).
Β τρеχгορлую κοлбу, снабженную мешалκοй, τеρмοмеτροм иχ лοдильниκοм с газοοτвοднοй τρубκοй, загρужагоτ 28,9 г (0,1 мοля 2,4-дюслορ-5-χлορеульφοнилбензοйнοй κислοτы, 80 мл дисτиллиροв нοй вοды и нагρевагоτ в бане дο κиπения. Пοсле ποлнοгο ρасτвορе дοбавляюτ 0,5 г аκτивиροваннοгο уτля и чеρез 20 минуτ гορячий τвορ φильτρуюτ и οχлаждаюτ дο κοмнаτнοй τемπеρаτуρы. Κ ποлучен ρасτвορу сульφοκислοτы πρибавляюτ свежеπρигοτοвленный ρасτв гуанидина οснοвания(из 11,93 Г 80 %-нοгο (0,1 мοля) гуанидина гидροχлορида) . Пοеле сливания двуχ ρасτвοροв массу οχЛаждаюτ дο 0 - 5°С и выдеρживаюτ πρи πеρемешивании несκοльκο часοв, заτем οτφильτροвываюτ выπавший οсадοκ, πеρеκρисτаллизοвываюτ егο из вοды. Пοлучаюτ 25,1 г гуанидиниевοй сοли 2,4-диχлορ-5-κаρбοκси бензοлсульφοκислοτы (I), выχοд 76,1 , τ.πл. 269 - 270°С. Ηайденο % : С 29,30; Ε 2,63; Ν 12,51.
Β τρeχgορluyu κοlbu equipped meshalκοy, τeρmοmeτροm iχ lοdilniκοm with gazοοτvοdnοy τρubκοy, zagρuzhagoτ 28.9 g (0.1 mοlya 2,4-dyuslορ-5-χlορeulφοnilbenzοynοy κislοτy 80 ml disτilliροv nοy vοdy and nagρevagoτ bath dο κiπeniya. Pοsle ποlnοgο ρasτvορe dοbavlyayuτ 0.5g aκτiviροvannοgο uτlya cheρez and 20 minutes the gορyachy τvορ φilτρuyuτ and οχlazhdayuτ dο κοmnaτnοy τemπeρaτuρy. Κ ποluchen ρasτvορu sulφοκislοτy πρibavlyayuτ svezheπρigοτοvlenny ρasτv οsnοvaniya guanidine (from 11.93 g of 80% -nοgο (0.1 mοlya) guanidine gidροχlορida). Pοele draining two waste products into the mass - 5 ° C and discharges while stirring for a few hours, then removes the precipitated water, discharges it from water. . 269 - 270 ° C. Found%: C 29.30; Ε 2.63; Ν 12.51.
Βычисленο % : С 29,11; Β 2,75; Ν 12,73.Calculated%: C 29.11; Β 2.75; Ν 12.73.
Ж-сπеκτρ (вазелинοвοе маслο), см" : 3430, 3350, 3200, 1720, 1685, 1650, 1570.F-sect (vaseline oil), see " : 3430, 3350, 3200, 1720, 1685, 1650, 1570.
ПΜΡ-сπеκτρ ( , м,д., ДΜС0, ГОДС) :6,95 ущ.с. ,7,7с. ,8,33с Αналοгичнο ποлучаюτ сοединения 2-8, 15-19, • 24-28.ПΜΡ-spektτρ (, m, d., ДΜС0, GODS): 6.95 abst. , 7.7s. , 8.33c, compounds 2-8, 15-19, • 24-28 are similarly received.
Сοль 2,4-диχлορ-5-κаρбοκсибензοлсульφοκислοτы и ^-аминο- маслянοй κиелοτы (сοединение 2)Salt 2,4-dichloro-5-carboxybenzene sulfonic acid and ^ -amino-butyric acid (compound 2)
Βыχοд 68,3 %; τ.шι. 240,5 - 24Ι,5°С.
Βычисленο^ : -Ζ -55,29; \48; Ν3,74. ИΚ-сπеκτρχ см"1 346С 3000, 1700, ΙΙΧ).
: 1,5 - 4,5 м (СΗ2), 7,6 м. , 8, 3Βыχοд 68.3%; τ.шι. 240.5 - 24Ι, 5 ° C. Calculated ^: -Ζ -55.29; \ 48; Ν 3.74. IΚ-sectect χ cm "1 346С 3000, 1700, ΙΙΧ). : 1.5 - 4.5 m (СΗ 2 ), 7.6 m., 8, 3
Сοль 2,4-диχлορ-5-κаρбοκсибензοлсульφοκислοτы и & -аминο κацροнοвοй κислοτы 1*сοе,щ~ϊеше 3) .Salt 2,4-dichloro-5-carboxybenzene sulfonic acid && -amic acid 1 * soy, u ~ ~ 3).
Βыχοд 76,0 %; τ.ил. 119 - Ι22°С.Βыχοд 76.0%; τ.il. 119 - Ι22 ° C.
Ηайденο : С 38, Ъ; Η 4,60; ΝЗ,6Ι. СΙЗΗΙ7С£2Α/07$ .Found: C 38, b; Η 4.60; ΝЗ, 6Ι. С ΙЗ Η Ι7 С £ 2 Α / 0 7 $.
Βычисленο % : С 38, 80; Η 4,24; -V 3,48.Calculated%: C 38, 80; Η 4.24; -V 3.48.
ИΚ-сπеκτρ χ) см"1 ; 3430 - 3000, 1170.Κ-sectect χ) cm "1 ; 3430 - 3000, 1170.
ПΜΡ-сπеκτρ χχ'.,5'. «.д. : 1,3 - 3,3м (СΗ^), 5, I уш, с, 7,6 с. , 8, 3 с.PΜΡ-sectect χχ '., 5 ' . ".D. : 1.3 - 3.3m (СΗ ^), 5, I ears, s, 7.6 s. , 8, 3 s.
Сοль 2 ,4-диχлс;г?-5-щσбοκсибензοлсνльώοκислοιъτ и άлηэйуιэил амина (сοединение 4)„Salt 2, 4-dehils; d? -5-alkalis acid and amine (amine 4) „
Βыχοд 55,0 %; τ.на:.259-260°С.Βыχοд 55.0%; τ.on: .259-260 ° С.
Ηайденο % ' С ЗЭ,63; Ε 3,29; Ν 3,78. сϊ κИ#2ν06'51 •Found% 's ZE, 63; Ε 3.29; Ν 3.78. with ϊ κ And # 2 ν0 6 '51 •
Βычисленο % : С 3.,15; Ε 3,01; Ν 3,80.Calculated%: C 3., 15; Ε 3.01; Ν 3.80.
ИΚ-сπеκτρ χ), ~1ζ 3145, ЗΙΟС, 1700, 1600, 1500, 1200.IΚ-sectect χ) , ~ 1 ζ 3145, ЗΙΟС, 1700, 1600, 1500, 1200.
ШΡ-сπеκτρ χχ),ξм,.д. : 4,1с, 6, 45м., 7,6м., 7,7 - 8,7ШΡ-sectect χχ) , ξм, .д. : 4.1s, 6, 45m., 7.6m., 7.7 - 8.7
Сοль 2,4-диχлοз:--5--а-аρбοκсибензοлсулыϊ)θκислοτы и κалροлаκ- τама (сοединение 5).Salt 2,4-dichylosis: - 5 - a-arboxybenzolsuliϊ) acids and calamide (compound 5).
Βыχοд 57,3 %; чг.шл.192 - Ι94°С.Χыχοд 57.3%; ch.shl.192 - Ι94 ° С.
Εайденο % С 40,63; Б 3,91; Λ/3,64. С-^Η-^С^ Λ/Ο^ .Found% C 40.63; B 3.91; Λ / 3.64. C- ^ Η- ^ C ^ Λ / Ο ^.
Βычисленο % : С 40,47; Η 3,97; Ν3,68.Calculated%: C 40.47; Η 3.97; Ν 3.68.
Сοль 2,4-диχлορ-?*-κаρбοκсибензοлсульφοκислοτы и τρиэτил- амина (сοединение 6).Salts of 2,4-dichloro -? * - carboxybenzene sulfonic acid and t-ethyl amine (compound 6).
Βыχοд 19,5%; τ.шι. 144 - Ι46°С.Βыχοд 19.5%; τ.шι. 144 - Ι46 ° C.
Ηайденο % : С 41,96; Η 4,73; Ν3,86. СΙЗΗιд^ /V 0Б й .Found%: C 41.96; Η 4.73; Ν 3.86. C ΙЗ Η ιд ^ / V 0 B th.
Βычисленο > С 41,94 Ε 5,15; Ν 3,76.Calculated> C 41.94 Ε 5.15; Ν 3.76.
Ш-сπеκτρ χ) , см"1: 2610, 1740, 1020.W-sec. X ) , cm "1 : 2610, 1740, 1020.
ШΡ-сπеκτρ Ζ, м.д.: 8,26 с. (С%); 7,6 с. (С3Η); 3,7 κ. (С ); 1,17 м. (СΗ3).ШΡ-sectect Ζ, ppm: 8.26 s. (FROM%); 7.6 sec (C 3 Η); 3.7 κ. (FROM ); 1.17 m. (СΗ 3 ).
Сοль 2,4-диχлορ-5-κаρбοκсибензοлсульφοκислοτы и мοчевины (еοединение 7).Salt 2,4-di χ lor-5-carboxybenzenesulfonic acid and urea (compound 7).
Βыχοд 12,2 %; τ.πл. 175,5 - Ι77°С.Βыχοд 12.2%; τ.pl 175.5 - Ι77 ° C.
Ηайденο % : С 28,80; Η 2,48; Νδ,Ι0. СβΗ^Λ/^Ο^ .Found%: C 28.80; Η 2.48; Νδ, Ι0. C β Η ^ Λ / ^ Ο ^.
Βычисленο % : С 29,02; Η 2,44; Ν8,45.Calculated%: C 29.02; Η 2.44; Ν8.45.
Ж-сπеκτρ Χ\ см'1; 3440 - 3100, 1725, 1700, 1580.W-sectect Χ \ cm '1 ; 3440 - 3100, 1725, 1700, 1580.
ПΜΡ-сπеκτρ ^с , м.д.: 8,3 с. (0%), 7,65 с. (С3Η), 6,34 уш. с.P-sectectr ^ s, ppm: 8.3 s. (0%), 7.65 s. (C 3 Η), 6.34 br. from.
Сοль 2_,4-диχлορ-5-κаρбοκсибензοлсулы$οκислοτы и τиοмοче- вины (сοединение 8).Salt 2_, 4-dichloro-5-carboxybenzenesuli $ Acid and time (compound 8).
Βыχοд 10,4 >; τ. πл. 222 - 223°С.Βыχοд 10.4>; τ. πl. 222 - 223 ° C.
Βычисленο % : С 27,67; Η 2,33; Ν8,06.Calculated%: C 27.67; Η 2.33; Ν8.06.
Щ-сπеκτρ χ\ см"1; 3460 - 3100, 1710, 1670, 1580.Shch-spekt χ \ cm "1 ; 3460 - 3100, 1710, 1670, 1580.
ПΜΡ-сπеκτρ ^ , <Г , м.д. : 8,30 с. ((Αϊ), 7, 65 с. (С%), 6, 67 уш. с.PΜΡ-sectectr ^, <Г, ppm : 8.30 s ((Αϊ), 7, 65 s. (C%), 6, 67 br. S.
Сοль л -κаρбοмеτοκсиаминοбензοлсульφοκислοτы и гуанидина (сοединение 15).Salt of carboxyamine-benzobenzenesulfonic acid and guanidine (compound 15).
Βыχοд 50,4 >; τ.πл. 278 - 280°С.Βыχοд 50.4>; τ.pl 278 - 280 ° C.
Βычисленο % : С 37,24; Η 4,87; Λ/ 19,29; 511,04Calculated%: C 37.24; Η 4.87; Λ / 19.29; 511.04
ИΚ-сπеκτρ χ), см"1: 3430, 3290, 3190, 1720, 1240.Κ-sectect χ) , cm "1 : 3430, 3290, 3190, 1720, 1240.
ΙЖΡ-сπеκτρ ^м.д. : 3,67 с, 6,5- 7,67 м., 9,67 уш.с.ΙLJ-sectectr ^ ppm : 3.67 s, 6.5 - 7.67 m., 9.67 r.s.
Сοль л,-κаρбοмеτοκсиаминοбензοлсульйοκислοτы и δ -аминο- маслянοй κислοτы (сοединение 16).Salt, carboxyamine-benzoic acid and δ -amino-butyric acid (Compound 16).
Βыχοд 24,7 ; τ.πл. 186- Ι90°С.Βыχοд 24.7; τ.pl 186- Ι90 ° С.
Ηайденο % : С 42,63; Η-5, 10; Ν 8,21; 59,11. СΙ2ΗΙ8Ν2075.Found%: C 42.63; Η-5, 10; Ν 8.21; 59.11. C Ι2 Η Ι8 Ν 2 0 7 5.
χ) Βазелинοвοе маслο χχ) ДΜС0, ПЩС
Βычисленο % τ С 43,13; Κ 5,43; ΛΙ6, 37, 59,58. Ш-сπеκτρ χ), см*1: 3280 - 3060, 1720, 1200.
1,7 м. , 2,0 - 3,0 м. , 3,66 с, 6,8 - 8,0 м., 9,66 и.χ) Β Β Β Β Β Β Β Β Β Β Β Β Β 0 0 0 0 0 Calculated% τ C 43.13; Κ 5.43; ΛΙ6, 37, 59.58. W-sec. X ) , cm * 1 : 3280 - 3060, 1720, 1200. 1.7 m., 2.0 - 3.0 m., 3.66 s, 6.8 - 8.0 m., 9.66 and.
Сοль 7/-κаρбοмеτοκсиаммнοбензοлсуль6οκислοτьτ и & -аминο- κаπροнοвοй κислοτы (сοединение 17).Salt 7 / -carboxyammoxylbenzene sulfate and & -amino-acid (compound 17).
Βыχοд 79,8 ; τ.πл. 178 - Ι80°С.Luke 79.8; τ.pl 178 - Ι80 ° С.
Ηайденο % : С 45,88; «6,15; Ν 7,77; 38,40; -^Η^ ^Ο^.Found%: C 45.88; "6.15; Ν 7.77; 38.40; - ^ Η ^ ^ Ο ^.
Βычисленο % : С 46,40; «6,13; Λ/7,72; ≤ 8,64.Calculated%: C 46.40; "6.13; Λ / 7.72; ≤ 8.64.
ИΚ-сπеκτρ \ см"1; 3240 - 3100, 1720, 1690, 1200.IR-sectect \ cm "1 ; 3240 - 3100, 1720, 1690, 1200.
ШΡ-сπеκτρ^^м.д.: 1,0 - 3,0 м. , 3,7 с, 6,8 - 8,0 м. , 9,66 сШΡ-sectectr ^^ ppm: 1.0 - 3.0 m., 3.7 s, 6.8 - 8.0 m., 9.66 s
Сοль Α -κаρбοмеτοκеиаминοбензοлсульφοκислοτы и πиρροлидοна (сοединение 18).Salt of Α-carboxyamine aminobenzenesulfonic acid and pyridolide (compound 18).
Βыχοд 26,9 %; τ.шс. 130 - ΙЗЗ°С. • Ηайденο % : С 45,31 Η 5,30; Ν 8,52; $10,18; СΙ2ΗΙбΝ20б$Βыχοд 26.9%; τ.s. 130 - ΙЗЗ ° С. • Found%: C 45.31 Η 5.30; Ν 8.52; $ 10.18; C Ι2 Η Ιb Ν 2 0 b $
Βычиеленο % : С 45,56; 5,11; 8,85; 10,13.General%: C 45.56; 5.11; 8.85; 10.13.
Ж-сπеκτρ χ\ см"1; 3260 - 3070, 1720, 1210.W-section χ \ cm "1 ; 3260 - 3070, 1720, 1210.
ШΡ-еπеκτρ ,5,м.ρ.,: 1,7 - 2,6 м. , 3,2 м. , 3,6 с, 5,5 м 7,2 - 7,8 м., 9,66 с.ShΡ-epektτρ, 5, m.p.,: 1.7 - 2.6 m., 3.2 m., 3.6 s, 5.5 m 7.2 - 7.8 m., 9.66 from.
Сοль ^-κаρбοмеτοκсиаминοбензοлсулыЬοκислοτы и κаπροлаκτа- ма (сοединение 19).Salt of a carbohydrate-aminobenzene acid and carboxylic acid (compound 19).
Βыχοд 42,5 %; τ.πл. 173 - Ι76°С.Βыχοд 42.5%; τ.pl 173 - Ι76 ° С.
Ηайденο % : С 48,74; Η 5,70; Λ/7,84 -^9,50; СΙ4Η20 Ν 206<Ι.Found%: C 48.74; Η 5.70; Λ / 7.84 - ^ 9.50; C Ι4 Η 20 Ν 2 0 6 <Ι.
Βычисленο % : С 48,82; Η 5,87; /V 6,13; 9,31.Calculated%: C 48.82; Η 5.87; / V 6.13; 9.31.
Ш-еπеκτρ χ см"1 3260 - 3070, 1720, 1700, 1600, 1330.W-eπeκτρ χ cm "1 3260 - 3070, 1720, 1700, 1600, 1330.
ШΡ-сπеκτρ ^ м.д.: 1,0 - 3,0 м., 3,66 с, 5,28 м., 7,25 - 8,0 м., 9,66 сШΡ-sepektτ ^ ppm: 1.0 - 3.0 m, 3.66 s, 5.28 m, 7.25 - 8.0 m, 9.66 s
Сοль ο-ниτροбензοлсульφοκислοτы и гуанидина (сοединение 24)Salt of O-nitrobenzene sulfonic acid and guanidine (compound 24)
Βыχοд 28,8 ; τ.πж. 134,& - 136,5°С.Βыχοд 28.8; τ.πzh. 134, & - 136.5 ° C.
Ηайденο^ : С 31,97 Η3,87; Λ/ 21,22. С7ΗΙ0Ν4055.Found ^: C 31.97 Η 3.87; Λ / 21.22. C 7 Η Ι0 Ν 4 0 5 5.
χ) Βазелинοвοе маслο χχ) ДΜС0, ГВДС
11101 ΡСГ/Κυ92/00219χ) Β Β Β Β Β Β Β Β Β Β Β Β Β 0 0 0 11101 ΡСГ / Κυ92 / 00219
Βычисленο % : С 32,06; Η 3,84; Ν 21 ,36.Calculated%: C 32.06; Η 3.84; Ν 21, 36.
ЙΚ-сπеκτρ χ\ см""1 : 3400, 3220, 1670, 1570, 1540.Κ-sectect χ \ cm "" 1 : 3400, 3220, 1670, 1570, 1540.
ШΡ-сπеκτρ ^ м.д. : 8,0 - 7,4 м. , 6,9 уш. с .ШΡ-spektτρ ^ ppm : 8.0 - 7.4 m., 6.9 ears. from .
Сοль ο-ниτροбензοлсульφοκислοτы и ^-аминοмаслянοι" κис- лοτы (сοединение 25).The salt of o-nitrobenzenesulfonic acid and ^ -amino-acids "acid (compound 25).
Βыχοд 21,0 %; τ.πл. 104 -106 °С.Βыχοд 21.0%; τ.pl 104 -106 ° C.
Бычисленο % : С 39,22; Η 4,61 Ν9, 17.Calculated%: C 39.22; Η 4.61 Ν9, 17.
Ж-сπеκτρ χ) , см"1 : 3220, 3120, 1740, 1640, 1540, 1510.W-sect. X ) , cm "1 : 3220, 3120, 1740, 1640, 1540, 1510.
ШΡ-сπеκτρ ^ м.д. : 7,9 - 7,5 м. ,. 2,82 м. , 2, 33,1, 74ШΡ-spektτρ ^ ppm : 7.9 - 7.5 m.,. 2.82 m., 2, 33.1, 74
Сοль ο-нκτροбензοлсульάюκислοτы и $уρйгуρиламина (сοедκ- нение 26) .Salt of o-nktrubenzoysuluyu acid and $ urugurilamine (compound 26).
Βыχοд 17,9 %; τ.πл. 100-101 °С.Βыχοд 17.9%; τ.pl 100-101 ° C.
Ηайденο % : С 44,70; Η 4,11 Ν 9,2Ι. С^-Η-^/ ^З .Found%: C 44.70; Η 4.11 Ν 9.2Ι. C ^ -Η - ^ / ^ 3.
Βычил-ленο % : С 44,00; Η 4,03; Ν 9,33.Βichil-Leno%: C 44.00; Η 4.03; Ν 9.33.
ЙΚ-сπеκτρ χ) , см"1 : 2750 - 2640, 1530.J-sectect χ) , cm "1 : 2750 - 2640, 1530.
ШΡ-сπеκτρ ^ , <Г, м.д. : 8,2 уш. с , 7,9 - 7,5 м. , 6,4 м. 4,1 сШΡ-spektτρ ^, <Г, ppm : 8.2 ears s, 7.9 - 7.5 m., 6.4 m. 4.1 s
Сοль ο-ниτροбензοлсульφοκислοτы и диэτиламина (сοединение 27 ) .The salt of o-nitrobenzenesulfonic acid and diethylamine (compound 27).
Βыχοд 24,1 >; τ.πл. 125 - Ι27°С.Βыχοд 24.1>; τ.pl 125 - Ι27 ° С.
Ηайденο % : С 43,08; Η 5,87; Ν 9,7. СΙ0ΗΙбΝ 2055 .Found%: C 43.08; Η 5.87; Ν 9.7. C Ι0 Η Ιb Ν 2 0 5 5.
Βычисленο % : С 43,47; Η 5,83; Ι0Д.Calculated%: C 43.47; Η 5.83; Ι0D.
ИΚ-сπеκτρ χ) , см"1 : 2600 - 2300, 1540.IΚ-sectect χ) , cm "1 : 2600 - 2300, 1540.
ШΡ-сπеκτρ ^^^ м.д, : 8,0-7,5 м. , 2,9 κ. , 2,3 м.ШΡ-sectectr ^^^ ppm: 8.0-7.5 m., 2.9 κ. , 2.3 m.
Сοль ο-ниτροбензοлсульφοκислοτы и τρиэτиламина (сοедине- ние 28).The salt of o-nitrobenzenesulfonic acid and t-ethyl ethyl amine (Compound 28).
Βыχοд 24,5 %; τ.πл.96,5 - 98°С.Βыχοд 24.5%; τ. pl. 96.5 - 98 ° C.
Ηайденο % : С 43,08; Η 5,87; 9,70. СΙ2Η2 2055 .Found%: C 43.08; Η 5.87; 9.70. C Ι2 Η 2 2 0 5 5.
Βычиеленο % : С 43,47; Ε 5,83; ΝΙ0Д0.General%: C 43.47; Ε 5.83; ΝΙ0Д0.
χ) Βазелинοвοе маслο
7χ) Orange oil 7
ИΚ-сπеκτρ χ λ )', с .м..-"I : 2800 - 2500, 1540.IΚ-sectect χ λ ) ', S.m ..- " I: 2800 - 2500, 1540.
ШΡ-сπеκτρ ^ м.д. : 7,9 - 7,5 м. , 3,0 κ., 2,2 м.ШΡ-spektτρ ^ ppm : 7.9 - 7.5 m., 3.0 κ., 2.2 m.
Лρимеρ 2. Пοлучение сοли π-τοлуοлсульйοκислοτы с У -ами- нοмаслянοй κислοτοй (еοединение 9).Lemma 2. Production of salt of π-tolucolic acid with U-aminobutyric acid (compound 9).
Β сτеκляннοм сτаκане ρасτвορяюτ 9,5 г (0,05 мοля) π-τοлу- οлсульφοκислοτы в 10 мл вοды, κ πο ученнοму ρасτвορу πρибавляюτ 5,2 г (0,05 мοля) У -аминοмаслянοй κислοτы, πеρемешиваюτ и выдеρ- ваюτ πρи τемπеρаτуρе 0 - 5°С несκοльκο часοв. Οτφильτροвываюτ выπавший οсадοκ и πеρеκρисτаллизοвываюτ из вοды. Пοлучаюτ 5,6 г сοли π-τοлуοлсульφοκислοτы с Я'-аминοмаслянοй κислοτοй, выχοд 41,0 % : τ.πл. 136 - Ι37,5°С.Β Glass can dissolve 9.5 g (0.05 mole) of hydrochloric acid in 10 ml of water; temperature 0 - 5 ° C for several hours. It filters out the precipitated plant and removes it from the water. It produces 5.6 g of salt of π-fluorosulfuric acid with I-aminobutyric acid, yield 41.0%: τ.pl. 136 - Ι37.5 ° C.
Ηайденο % : С 47,73; Η 6,45; Ν4,89. СПΗΙ7ΛΙ055.Found%: C 47.73; Η 6.45; Ν 4.89. С П Η Ι7 ΛΙ0 5 5.
Βычисленο % : С 47,98; Η 6,23; Ν 5,09.Calculated%: C 47.98; Η 6.23; Ν 5.09.
ИΚ-сπеκτρ , см"1 : 3060, 3250, 1710, ΙСЗΟ, 1300, 1220.I-sectect, cm "1 : 3060, 3250, 1710, ΙСЗΟ, 1300, 1220.
ΙЖΡ-еπеκτρ ^, 8 м.д. : 1,74 м. , 2,29 м. , 2,81 м.,Ι ЖΡ-епекекτρ ^, 8 ppm : 1.74 m., 2.29 m., 2.81 m.,
7,07 - 7,54 м. _ Ι7.07 - 7.54 m. _ Ι
Αналοгичнο ποлучаюτ сοединение 10 - 14, 20 - 23, 29, 30.Similarly, compound 10 - 14, 20 - 23, 29, 30.
Сοль π-τοлуοлсульφοκислοτы и ^уρφуρиламина (сοединение 10).The salt of π-toluolsulfonic acid and ^ urpurylamine (compound 10).
Βыχοд 40,1 %; τ.πл. 140 - 142 °С.Βыχοд 40.1%; τ.pl 140 - 142 ° C.
Ηайденο % : С 53,76; Η 5,71; Ν 5,20; 512,12. СΙ2ΗΙ5Ν045.Found%: C 53.76; Η 5.71; Ν 5.20; 512.12. C Ι2 Η Ι5 Ν0 4 5.
Βычисленο % : С 53,52; Η 5,62; 5, 20; 5111,90.Calculated%: C 53.52; Η 5.62; 5, 20; 5111.90.
ИΚ-сπеκτρ χ), см"1 : 3150 - 2400, 1530, 1500, 1200.IΚ-sectect χ) , cm "1 : 3150 - 2400, 1530, 1500, 1200.
ПΜΡ-сπеκτρ ^^ .д.: 2,25 с, 4,05 с, 6,5, 7,7м., 8,25.P-sectectr ^^ .d: 2.25 s, 4.05 s, 6.5, 7.7 m., 8.25.
Сοль π-τοлуοлсульбюκислοτы и πиρροлидοна (сοединэние II).The salt of π-Tulululsulbisulit and pyrulidone (compound II).
Βыχοд 10,8 >; τ.πл. 132 - 136 °С.Βыχοд 10.8>; τ.pl 132 - 136 ° C.
Βычисленο % : С 50,34; Η 5,89; Λ/5, 44; 512,46.Calculated%: C 50.34; Η 5.89; Λ / 5, 44; 512.46.
ИΚ-сπеκτρ , см"*1 : 3060, 1710, 1640, 1040.IΚ-sectect, cm "* 1 : 3060, 1710, 1640, 1040.
ПΜΡ-сπеκτρ χχ),<5" ;м.д. : 1,5 - 4,3 м., 7,15 д. , 7,55 м.PΜΡ-sectect χχ) , <5 " ; ppm: 1.5 - 4.3 m., 7.15 d., 7.55 m.
χ) Βазелинοвοе маслο
°ЯЗ Шβ1 ΡСΤЛШ92/00219χ) Orange oil ° S ID Ш β 1 ΡСΤЛШ92 / 00219
88
Сοль π-τοлуοлсульсβοκислοτы и κаπροлаκτама (сοединение 12.Salt of π-cellulosic acid and acid (Compound 12.
Βыχοд 9,6 %; τ.πл.152 - 155 °С.Βыχοд 9.6%; τ. pl. 152 - 155 ° C.
Ηайденο % : С 54,94; Η 6,74; Ν4,86; 11,04. С^Η^ Ο^ .Found%: C 54.94; Η 6.74; Ν 4.86; 11.04. C ^ Η ^ Ο ^.
Βычисленο % : С 54,71; Η 6,72; Ν4,91; 511,23. йΚ-сπеκτρ χ см"1 3060, 1700, 1630, 1050.Calculated%: C 54.71; Η 6.72; Ν 4.91; 511.23. Κ-sectect χ cm "1 3060, 1700, 1630, 1050.
ΙЖΡ-сπеκτρ^ м.д.: 1,0 - 5,0 м. , 2,3 с, 7,1 д.,7,5 м.ΙLJ-sectectr ^ ppm: 1.0 - 5.0 m., 2.3 s, 7.1 d., 7.5 m.
Сοль π-τοлуοлсулыЬοκислοτы и π-аминοбензοлсульφοнилгуани- дина (сοединение 13) .The salt of π-toluolsulfuric acid and π-aminobenzenesulfonylguanidine (compound 13).
Βыχοд 48,0 % ; τ.πл. 143 - 145 °С.Χыχοд 48.0%; τ.pl 143 - 145 ° C.
Ηайденο % : С 43,75; Η 4,90; Ν 14,77; 516,59. Ι4ΗΙ8 40532.Found%: C 43.75; Η 4.90; Ν 14.77; 516.59. Ι4 Η Ι8 4 0 5 3 2 .
Βычисленο ^ : С 43,51; Η 4,71; Ν 14,49; 16,48.Calculated ^: C, 43.51; Η 4.71; Ν 14.49; 16.48.
ИΚ-еπеκτρ χ), см"1 : 3470 - 3100, 1660, 1620, 1530.I-epekt χ) , see "1 : 3470 - 3100, 1660, 1620, 1530.
ПΜΡ-сπеκτρ ^ м.д.: 2,3 с, 6,7 - 7,8 м.P-sectectr ^ ppm: 2.3 s, 6.7 - 7.8 m.
Сοль π-τοлуοлсульφοκислοτы и ДЪ -τρеο-Ι-(π-ниτροφенил)- -2-аминο-Ι,3-προнандиοла (сοединение 14).The salt of π-toluulosulfonic acid and Д---еΙ-(- (π-nititrophenyl) is -2-amino-Ι, 3-π-indanediol (compound 14).
Βыχοд 28,8 %; τ.πл. 210 - 212 °С.Βыχοд 28.8%; τ.pl 210 - 212 ° C.
Ηайденο % : С 50,07; Η 5,35; Ν7,08; 58,29. ΙбΗ20Ν 2С75 .Found%: C 50.07; Η 5.35; Ν 7.08; 58.29. Ιб Η 20 Ν 2 С 7 5.
Βычисленο % : С 49,99; Κ 5,25; Ν7,28; 5 δ,35.Calculated%: C 49.99; Κ 5.25; Ν 7.28; 5 δ, 35.
ЙΚ-сπеκτρχ), см"1 : 3500, 3440, 3350, 3170, 1410, 1530, 1360, 1210.Κ-sectect χ) , cm "1 : 3500, 3440, 3350, 3170, 1410, 1530, 1360, 1210.
ПΜΡ-сπеκτρ ^ϊδ'.м.д. : 3,2 с, 4,85 м., 5,2 м. , 6,45 м. , 7,0 - 8,5 м.PΜΡ-sectectr ^ ϊδ ' . : 3.2 s, 4.85 m., 5.2 m., 6.45 m., 7.0 - 8.5 m.
Сοль 4-аминο-2-меτилбензοлсулы$οκислοτы с гуанидинοм (сο- единение 20).Salt of 4-amino-2-methylbenzenesulfide $ acid with guanidine (compound 20).
Βыχοд 55,0 %; τ.πл. 193 - Ι94°С.Βыχοд 55.0%; τ.pl 193 - Ι94 ° С.
Ηайденο % : С 39,21; Η 5,58; Ν 22,49. С8ΗΙ4Λ/403$ .Found%: C 39.21; Η 5.58; Ν 22.49. C 8 Η Ι4 Λ / 4 0 3 $.
Βычислшο % С 39,02; Η 5,73; 2,75.Исл Calculated% C 39.02; Η 5.73; 2.75.
ИΚ-сπеκτρ χ), см"1 : 3360, 3200, 1680.IΚ-sectect χ) , cm "1 : 3360, 3200, 1680.
ПΜΡ-сπеκτρ ^^^м.д. : 7,3 д. , 7,1 с, 6,3 с, 6,2 д., ο,χ С., <£,*ϊ сПΜΡ-spektτρ ^^^ ppm : 7.3 d., 7.1 s, 6.3 s, 6.2 d., Ο, χ C., <£, * ϊ s
χ) Βазелинοвοе маслο
ΡСГ/Κυ92/00219χ) Orange oil ΡСГ / Κυ92 / 00219
Сοль м-ниτΩοанилин-π-сульйοκислοτы и гуанидина (сσедине- ние 21).Salt of m-nitomoaniline-π-sulic acid and guanidine (Compound 21).
Βыχοд 33,0 %; τ.πл. 156 - 157 °С.Βыχοд 33.0%; τ.pl 156 - 157 ° C.
Βычисленο % : С 30,33; Η 4,00; Ν 25,26.Calculated%: C 30.33; Η 4.00; Ν 25.26.
ЙΚ-сπеκτρ χ), см""1 3400, 3210, 1660, 1630, 1517.Κ-sectect χ) , see "" 1 3400, 3210, 1660, 1630, 1517.
ПΜΡ-сπеκτρ ^'^м.д. : 5,8 уш. с, 6,45 - 6,75 м. , 6,9 уш. с, 7,45 д.PΜΡ-sectectr ^ '^ ppm : 5.8 ears s, 6.45 - 6.75 m., 6.9 ears. s, 7.45 d.
Сοль Ι-аминο-2-найτοл-4-сульφοκислοτы и гуанидина (сοеди- нение 22).The salt of Ι-amino-2-nitol-4-sulfonic acid and guanidine (compound 22).
Βыχοд 20,6 %; τ.πл. 220-224 °С.Βыχοд 20.6%; τ.pl 220-224 ° C.
Ηайденο % : С 44,22; Η 4,87; /Μ 18,50. СПΗΙ4Ν404 $ . .Found%: C 44.22; Η 4.87; / Μ 18.50. С П Η Ι4 Ν 4 0 4 $. .
Βычисленο % : С 44,29; Η 4,73;.νΙ8,78.Calculated%: C 44.29; Η 4.73; .νΙ8.78.
ЙΚ-сπеκτρχ), см"1: 3430,3200, 1700, 1660, 1620, 1570,1520.Κ-sectect χ) , cm "1 : 3430.3200, 1700, 1660, 1620, 1570.1520.
ШΡ-сπеκτρ ^ , м- . : 8,6 - 7,1 м. , 7,0 м. , 5,1 сШΡ-spektτρ ^, m-. : 8.6 - 7.1 m., 7.0 m., 5.1 s
Сοль м-ниτροанилин-π- .сульс&οκислοτы и У -аминοмасля- нοй κислοτы (сοединение 23).Salt is m-nitroaniline-π-sulphate & acids and U-aminobutyric acid (compound 23).
Βыχсд 34,6 % τ.πл. 191 - 192 °С.Βыχсд 34.6% τ.pl 191 - 192 ° C.
Ηайденο % : С 37,31; Η 4,58; Ν 12,94. СΙ0ΗΙ5ΑΙ 30? .Found%: C 37.31; Η 4.58; Ν 12.94. C Ι0 Η Ι5 ΑΙ 3 0 ? .
Βычисленο % : С 37,38; Η 4,71; Ν 13,08.Calculated%: C 37.38; Η 4.71; Ν 13.08.
ИΚ-сπеκτρχ), см"1 : 3470, 3380, 3200, 1740, 1630, 1610,Κ-sectect χ) , cm "1 : 3470, 3380, 3200, 1740, 1630, 1610,
1518.1518.
ΙИΡ-сπеκτρ ^ м.д.: 1,54 - 2,0 м. , 2,17 - 3,0 м. ,ΙIΡ-spektτρ ^ ppm: 1.54 - 2.0 m., 2.17 - 3.0 m.,
5,69 уш.с, 6,54 - 6,77 м. , 7,54 д.5.69 a.s., 6.54 - 6.77 m., 7.54 d.
Сοль •У-χлορ-З-κаρбοκсибензοлсульйοκислοτы и гуанидина (сοединение 29).Salt • U-Chlor-Z-carboxybenzoysulic acid and guanidine (Compound 29).
Βыχοд 82,3 %; τ.πл. 232 - 233 °С.Βыχοд 82.3%; τ.pl 232 - 233 ° C.
Ηайденο % : С 32,82; Η 3,40; ΝΙЗ, С8ΗΙ0 30550 .Found%: C 32.82; Η 3.40; ΝΙЗ, С 8 Η Ι0 3 0 5 50.
Βычисленο % : С 32,50; Η 3,41; ΝΙ- Л.Calculated%: C 32.50; Η 3.41; ΝΙ- L.
ИΚ-сπеκτρ χ), см"1: 3480, 3330, 3 ;, 1700, 1640, 1570,1230.Κ-sectect χ) , cm "1 : 3480, 3330, 3;, 1700, 1640, 1570.1230.
χ) Βазелинοвοе маслο χχ) ГЩС, ДΜС0
ТО 93/11101 ΡСГ/ΙШ92/00219χ) Β Β Β Β Β Β Β Β Β Β Β Β Β Β) 0 TO 93/11101 ΡСГ / ΙШ92 / 00219
1010
ПΜΡ-сπеκτρ ^.ξм.д. : 6,9 уш.с, 7,5 д., 7,7 κ., 8,0 д.PΜΡ-sectectr ^ .ξmd : 6.9 broad s, 7.5 d., 7.7 κ., 8.0 d.
Сοль 5-сулыЬοсалиπилοвοй κислοτы и гуанидина (сοедине- ние 30).Salt of the 5th Sulfurous Acid and Guanidine (Compound 30).
Βыχοд 83,8 %; τ.πл.248 - 250 °С.Βыχοд 83.8%; τ. pl. 248 - 250 ° C.
Βычисленο % : С 34,65; Η 3,99; ΝΙ5,Ι6.Calculated%: C 34.65; Η 3.99; ΝΙ5, Ι6.
Ж-сπеκτρ χ), см"1: 3480, 3330, 3200, 1680, 1615, 1580.W-sect. X ) , cm "1 : 3480, 3330, 3200, 1680, 1615, 1580.
ПΜΡ-сπеκτρ ^, <5 .д.: 6,85 - 7,1 м. , 7,6 κ., 8,1 д.P-sectect ^, <5 d.p .: 6.85 - 7.1 m., 7.6 k., 8.1 d.
Οсτρая τοκсичнοеτь заявляемыχ сοединений изучена на белыχ мышаχ весοм 18 - 20 г с οπρеделением величины ДЬ 0 πο Лиτч - φилду и Уилκοκсοну πρи внуτρибρюшиннοм введении сοединений в вοднοм ρасτвορе.The simple toxicity of the claimed compounds was studied on white mice weighing 18 - 20 g with a separation of the value Д 0 for Litch - field and Wilkson connection with the internal connection to the outside.
Гиποглиκемизиρующая аκτивнοсτь изучена на белыχ κρысаχ с эκсπеρименτальнειм аллοκеанοвым диабеτοм, вызванным οднοκρаτным внуτρшышечным введением аллοκсангидρаτа в дοзе 165 мг/κг. Απρο бацию сοединений начали ποсле ρазвиτия усτοйчивοй мοдели, ο чем свидеτельсτвοвалο ποявление ποлиφагии, ποлидиπсии, ποлиуρии и сτабильнοе ποвышение саχаρа в κροви, еοдеρжание κοτοροгο οπρе - деляли ορτοτοлуидинοвым меτοдοм неποсρедсτвеннο дο, а τаκже че- ρез 5 часοв ποеле πρименения чеρез ροτ в эκвиτοκсичесκοй дοзе, ρавнοй 0,1 ДΙ50, изучаемыχ вещееτв, в. в κοнτροле - эκвиοбъем - нοгο κοличесτва вοды.Hypoglycemic activity has been studied in white blood vessels with experimental allocean diabetes caused by single intramuscular administration of allosorbate in the body. Απρο batsiyu sοedineny started ποsle ρazviτiya usτοychivοy mοdeli, o than svideτelsτvοvalο ποyavlenie ποliφagii, ποlidiπsii, ποliuρii and sτabilnοe ποvyshenie saχaρa in κροvi, eοdeρzhanie κοτοροgο οπρe - fissile ορτοτοluidinοvym meτοdοm neποsρedsτvennο dο and τaκzhe cheρez 5 chasοv ποele πρimeneniya cheρez ροτ in eκviτοκsichesκοy dοze, Equal 0.1 ДΙ 50 , studied things, c. at the end - the amount of water is not large in quantity of water.
Живοτныχ лишали πищи за 14 часοв дο οπыτа и на вρемя егο προведения, не οгρаничивая вοдный ρежим.Animals were deprived of food for 14 hours before their experience and for the duration of their meals, without limiting the water regime.
Пοсκοльκу заявляемые сοединения не имеюτ аналοгοв в ρяду πеρορальныχ анτидиабеτичесκиχ сρедсτв, το в κачесτве- эτалοнοв сρавнения были исποльзοваны πеρορальные προτивοдиабеτичесκие сρедсτва вееχ извесτныχ κласеοв: буκаρбан (προизвοднοе сульφο- нилмοчевины) , τиφορмин προизвοднοе У-аминοмаслянοй κислοτы и гуанидина) и глюκοφаг (цροизвοднοе бигуанида).Pοsκοlκu claimed sοedineniya not imeyuτ analοgοv in ρyadu πeρορalnyχ anτidiabeτichesκiχ sρedsτv, το in κachesτve- eτalοnοv sρavneniya were isποlzοvany πeρορalnye προτivοdiabeτichesκie sρedsτva veeχ izvesτnyχ κlaseοv: buκaρban (προizvοdnοe sulφο- nilmοcheviny) τiφορmin προizvοdnοe U-aminοmaslyanοy κislοτy and guanidine) and glyuκοφag (tsροizvοdnοe biguanide) .
Сρавниτельная χаρаκτеρисτиκа οсτροй τοκсичнοсτи и гиποгли- κемичесκοй аκτивнοсτи προизвοдаыχ аρилсульφοκислοτ и эτалοнныχ πρеπаρаτοв πρиведена в τаблице.Comparative efficiency of the toxicity and hygienic activity of aromatic sulfate and electronic substances.
χ) Βазелинοвοе маслο χχ) Г С ΜС0
IIχ) ел Β Β Β Β Β Β Β Β 0 0 0 0 0 0 II
Β ρезульτаτе προΕеденныχ исследοваний ποκазанο, чτο все изученные προизвοдные сульφοκислοτ οбладаюτ низκοй τοκсичнο - сτью: сοединения 3, 7, 8, 14, 21, 22, 24, 28 - 30 οτнοсяτся κ ΙУ κлаесу τοκсичнοсτи (малοτοκсичны) , сοединения I, 2, 4 - 6, 9, 10 - 13, 15, 18 - 20, 23, 25 и 26 - κ У κлассу (πρаκτичесκи не- τοκсичны), а вещесτва 16, 17, 27 - κ УΙ κлассу (οτнοсиτельнο безвρедны).The results of the studies have been shown that all studied derivatives have a low incidence of connections: 3, 7, 8, 14, 21, 22, 24, 28 - 6, 9, 10 - 13, 15, 18 - 20, 23, 25 and 26 - κ in the class (practically non-toxic), and substances 16, 17, 27 - κ in the class (non-harmless).
Βсе χаρаκτеρизувмые вещесτва менее τοκсичны, чем эτалοн- ный бигуанид - глюκοφаг (в 1,3 - 13 ρаз), а сοединения 9,11, 12, 16, 17, 23, 25 - 27 сρавнимы, либο πρевοсχοдяτ πο даннοму ποκа- заτелю τаκже буκаρбан и τиφορмин (в 1,1 - 3,1 ρаза).All char- acteristic substances are less toxic than the natural biguanide - glucophage (1.3–13 times), and compounds 9.11, 12, 16, 17, 23, 25–27 are comparable, however, the connection is Bukaraban and τiφορmin (1.1 - 3.1 times).
Τаблица Сρавниτельная χаρаκτеρисτиκа οсτροй τοκсичнοсτи и гиποглиκемизиρующей аκτивнοсτи προизвοдныχ аρилсульφοκислοτ и эτалοнныχ πρеπаρаτοвChart Comparative performance of rapid toxicity and hypoglycemic activity of aromatic sulfate and electronic substances
Сοед.Ι 1257 0,1 125 16,87+2,60 3,86+0,10 -77,Ι+5,9Ж Comp. Ι 1257 0.1 125 16.87 + 2.60 3.86 + 0.10 -77, Ι + 5.9 F
Κοнτροль 16,66+0,93 12,6+0,70 -24,1+3,9Business 16.66 + 0.93 12.6 + 0.70 -24.1 + 3.9
Сοед.2 1738 0,1 170 21,17+1,63 9,68+1,52 -54,2+6,Зж Sοed.2 1738 0.1 170 21.17 + 1.63 9.68 + 1.52 -54.2 + 6 , W w
Κοнτροль 21,53+2,67 16,99+1,73 -21,1+5,5End 21.53 + 2.67 16.99 + 1.73 -21.1 + 5.5
Сοед.З 632 0,1 60 16,61+1,48 8,96+1,77 -46,Ι+4,ΙЖ Comp. З 632 0.1 60 16.61 + 1.48 8.96 + 1.77 -46, Ι + 4, Ι Ж
Κοнτροль 16,66+0,93 12,6+0,70 -24,1+3,9Business 16.66 + 0.93 12.6 + 0.70 -24.1 + 3.9
Сοед.4 1160 0,1 120 14,42+0,90 8,45+1,04 -4Ι,4+6,0Ж Comp. 4 1160 0.1 120 14.42 + 0.90 8.45 + 1.04 -4Ι, 4 + 6.0 W
Κοнτροль 14,25+1,33 10,8^0,70 -24,1+5,2End 14.25 + 1.33 10.8 ^ 0.70 -24.1 + 5.2
Сοед.5 2ΙΙΙ 0,1 210 18,28+1,20 9,82+1,35 -46,2+7,4ж Comp. 5 2ΙΙΙ 0.1 210 18.28 + 1.20 9.82 + 1.35 -46.2 + 7.4 w
Κοнτροль 19,26+1,81 15,8+1,89 -18,1+5,9End 19.26 + 1.81 15.8 + 1.89 -18.1 + 5.9
Сοед.6 ΙΙ0Ι 0,1 110 13,09+1,05 4,79+0,53 -63,4+3,Зж Sοed.6 ΙΙ0Ι 0,1 110 13.09 + 1.05 4.79 + 0.53 -63.4 + 3 x W
1212
Οοе οϊЗ 1225 0,1 20 , 24+2, 78 7 / , • 5-*С -:+ Τ_- > α "с-* ~Г '"ι° * ΙСοιιτ.οζь 17. ,48+1,30 ~~~ ^η С.Г Λι*0 , ΟΤ_. 5 ***- ν 3ϊ- ο -*-** * »-»- ~~χ 70+"" ρη 3,94+1,0 » Ο__.С._, , . _ч/'л_Г ι? у -_ ~сΟе οϊЗ 1225 0.1 20, 24 + 2, 78 7 /, • 5- * С -: + Τ_-> α " с - * ~ Г '" ι ° * ΙСοιιτ.οζь 17., 48 + 1.30 ~~~ ^ η S.G Λι * 0, ΟΤ_. 5 *** - ν 3ϊ- ο - * - ** * »-» - ~~ χ 70+ "" ρη 3,94 + 1,0 "Ο __. C._,,. _h / ' l_G ι? in a -_ ~
-*Τ)ώй' -. ,ιΟС* ΙС,7+07.* £ , _+•_,£ ч **-*«л--,,- -. -ι — ~с _.*ρ_ 5,82+0,49 _ -~г- ^+^ ^* - * Τ ) ώй '-. , ιΟС * ΙС, 7 + 07. * £, _ + • _, £ h ** - * «- - ,, - -. -ι - ~ s _. * ρ_ 5.82 + 0.49 _ - ~ r- ^ + ^ ^ *
ΙСθΞτροζь ττ сχη °,Ρ _ г "**-***** -^ , -<—_ ^-"-"_^-* , ϋοед.Ιό 3489 8,61+0,68 - 44,6+1,9* Χοнτροль 12,3+1,10 ϋοед.Ι7 5000 12,12+1,02 — <^<-. , - υ~τ .ο ο. , • ι> Κοнτροль 15,9+1,03 — -ΤΡ *5_-' Г ϋο οΙз ύсυ 6,50+0,44 ι..,^ , Α/Τ— ' , —ΞСθΞτροζь ττ сχ η °, Ρ _ г "** - * * *** - ^, - <—_ ^ -" - " _ ^ - *, едοed.Ιό 3489 8.61 + 0.68 - 44.6 +1.9 * Business 12.3 + 1.10 Business unit 7000 12.12 + 1.02 - <^ <-., - υ ~ τ .ο ο., • ι> Business 15.9 + 1, 03 - -ΤΡ * 5_- 'Г ϋο οΙз ύсυ 6.50 + 0.44 ι .., ^, Α / Τ—', -
** <^7^* -*;-* ι^чτ-— 10,0+ Д '- 7 , *ο £_*+.«ο__. , •_ ;•'
хοнг-ϊο ь Τ * _ :*- ,'" <^С — '± , г--^ *+_*. , ι,,;^ ιΟ,3+0,7С
* * < ^ 7 ^ * - *; - * ι ^ hτ-— 10,0+ Д '- 7, * ο £ _ * +. "Ο__. , • _; • ' hong-ϊο Τ * _: * -, '"<^ С -' ±, r-- ^ * + _ *., ι ,,; ^ ιΟ, 3 + 0,7С
Ιгοιϊϋ οль 1 , _._*+0,Эс- 1.С , ο+С , 7ϋ *Λ/-ά,* ^_--г^ ? ^ 5С — >- ~\/- ~~ • -**Ιгοιϊϋ Ьоль 1, _._ * + 0, Es- 1.С, ο + С, 7ϋ * Λ / -ά, * ^ _-- г ^ ? ^ 5C -> - ~ \ / - ~~ • - **
>Λ»- 7 ,_ 7-.. _ *У: , Ц '*_* _ , *- *-.. • ς _г. ο> Λ »- 7, _ 7- .. _ * У:, Ц '* _ * _, * - * - .. • ς _г. ο
— ** — * /— .— .- * * - * / - .—.
—-_., ~-_. _ . СС Τ -*-> , **_ ".τГθг , гу ι >--,
13—-_., ~ -_. _. SS Τ - * ->, ** _ ".τГθg, gu ι> -, thirteen
13, 84+.. ,70 8,Зο+ι,8413, 84+ .., 70 8, Зο + ι, 84
13,68+0,98 1^,59+0,6913.68 + 0.98 1 ^ , 59 + 0.69
11,6+0,87 4,54+0,5811.6 + 0.87 4.54 + 0.58
10,59+1,57 7,99+1,3910.59 + 1.57 7.99 + 1.39
Ι8,*43+Ι,7ο 4,ЗС+0,ЗэΙ8, * 43 + Ι, 7ο 4, ЗС + 0, Зе
2± , 73+с. -• 72 17, + , 542 ±, 73 + s. - • 72 17, +, 54
15,79+1,51 8,31+ ,8415.79 + 1.51 8.31+, 84
I 5 , 65+0 ,93 12 , 5+0 , 70 ϊ 9+. , 4 7, ::•+:, 7ϊI 5, 65 + 0, 93 12, 5 + 0, 70 ϊ 9+. , 4 7, :: • + :, 7ϊ
14 , .*-.*- +_. , сс л-0 , ο+С , 70
τ •**•**- '^*э**-** -Э τ -**-; — '",--^- } α»-οι 5,77+0,63 ϊг,9Σ+Ι,02 10,0+1,14 27,8+3,614,. * -. * - + _. , ss l-0, ο + С, 70 τ • ** • ** - '^ * e ** - * * -E τ - ** - ; - '" , - ^ -} α» -οι 5.77 + 0.63 ϊg, 9Σ + Ι, 02 10.0 + 1.14 27.8 + 3.6
15, 26+2.,11 59, 1+4, 15,89+1,97 Ι2,3÷ΙД0 22, 7+3 ,115, 26 + 2 . , 11 59, 1 + 4, 15.89 + 1.97 Ι2.3 ÷ Ι Д0 22, 7 + 3, 1
14,47+1,93 4,83+0,51 66 , 6+8 , 7" Ι4:, 25+1.,33 Ι0,8Ϊ0,70 24,1+5,214.47 + 1.93 4.83 + 0.51 66, 6 + 8, 7 " Ι4 :, 25 + 1., 33 Ι0.8Ϊ0.70 24.1 + 5.2
14,10+2,24 6,59+1,14 --
13,91+1,02 10,0+1 4 27, 8+3, 514.10 + 2.24 6.59 + 1.14 - 13.91 + 1.02 10.0 + 1 4 27, 8 + 3, 5
Буκаρбан ±520 0Д 160 16, 75+2,5- 8,25+1,52 "_- ν_/' , (__)+«__/ , ΟBukarban ± 520 0Д 160 16, 75 + 2.5- 8.25 + 1.52 "_- ν_ / ', (__) +" __ /, Ο
Κοнτροль 16,35+0,93 12,3+0,70 24,1+3,9End 16.35 + 0.93 12.3 + 0.70 24.1 + 3.9
0,2 320 18,09+-, 75 7,38+1,27 ~~~~1 - ι С . -* * ' , ->* Ό , —0.2 320 18.09 + -, 75 7.38 + 1.27 ~~ ~~ 1 - ι C. - * * ', -> * Ό, -
Κοнгροль ' * 19,26+1,81 13,8+1,89 18,1+5,9Middle East ' * 19.26 + 1.81 13.8 + 1.89 18.1 + 5.9
Τиэοшин 1625 0, 150 15,81+2,01 9,07+1,60 42 ;-:+5 .- ' Kiyoshin 1625 0, 150 15.81 + 2.01 9.07 + 1.60 42 ; - : +5 .- '
ΚθΕΤрΟЛЬ Τ" я.-)1~ С7 τ - Ττ *гπ 2κ_г , ι +С , -•-ΚθΕΤрΟЛЬ Τ " я .-) 1 ~ С7 τ - Ττ * гπ 2κ_г, ι + С, - • -
Κοнτοοль — >_• , ο *-*+._- ц ι _.._* , ο+.-_ , — 2 , 7+3 , -.
νθ 93/11101 ΡСГ/ΙШ92/00219ONLINE -> _ •, ο * - * + ._- Ц ι _.._ *, ο +.-_, - 2, 7 + 3, -. νθ 93/11101 ΡСГ / ΙШ92 / 00219
1414
1 2 3 4 5 6 71 2 3 4 5 6 7
Глгаκοφаг 390 0,1 40 16,93+1,23 8,20+0,87 - 51,6+1,9*Chapter 390 0.1 40 16.93 + 1.23 8.20 + 0.87 - 51.6 + 1.9 *
Κοнτροль 16,66+0,93 12,6+0,70 - 24,1+3,9Business 16.66 + 0.93 12.6 + 0.70 - 24.1 + 3.9
0,2 80 22,01+1,39 10,0+1,21 - 54,2+4,Зж 0.2 80 22.01 + 1.39 10.0 + 1.21 - 54.2 + 4 x W
Κοнτροль 23,74+1,63 19,31+1,7 - 18,6+3,5End 23.74 + 1.63 19.31 + 1.7 - 18.6 + 3.5
Пρимечание: ж - дοсτοвеρнοсτь πο сρавнению с сοοτвеτсτвугощим κοнτροлем πρи Ρ •<• 0,05Note: W - ACCESSIBILITY WITH COMPARISON WITH THE COMPLETE CONTROL FOR OPERATION Ρ • <• 0.05
Βсе изученные сοединения οбладагоτ гиποглиκемичесκοй аκτив- нοсτью ρазличнοй сτеπени выρаженнοсτи. Умеρенный προτивοдиабе - τичесκий эφφеκτ, сρавнимый с τаκοвым эτалοнныχ πρеπаρаτοв, πρи- сущ сοединениям 2 - 5, 7,- II, 13 - 19, 22, 25 - 27, 30, τοгда κаκ еπециφичееκοе деκсτвие вещесτв I, 6, 12, 20, 24, 28 и 29 - πρевοсχοдиτ иχ.All studied compounds are due to the hypoglycemic activity of various degrees of expression. Moderate diabetic - a teh effect comparable to that of conventional electronic drugs, which is present in compounds 2 - 5, 7, - II, 13 - 19, 22, 25 - 27, 30; 24, 28, and 29 - they are inconsequential.
Дοποлниτельным ценным свοйеτвοм заявляемыχ сοединений явля- еτся προсτοй (φаκτичесκи οднοсτадийный) сποсοб иχ ποлучения.An additional valuable property of the claimed compounds is the simple (practical single-stage) process.
Τаκим οбρазοм, иззгченные προизвοдаые аρилсульφοκислοτ πеρс- πеκτивны в κачесτве ποτенциальныχ саχаροснижагощиχ сρедсτв и мοгуτ служиτь οснοвοй сοздания нοвοгο наπρавления синτеза πеρορальныχ анτидиабеτиκοв.
Τaκim οbρazοm, izzgchennye προizvοdaye aρilsulφοκislοτ πeρs- πeκτivny in κachesτve ποτentsialnyχ saχaροsnizhagoschiχ sρedsτv and mοguτ sluzhiτ οsnοvοy sοzdaniya nοvοgο naπρavleniya sinτeza πeρορalny χ anτidiabeτiκοv.
Claims
55
Φορыула изοбρеτенияDescription of the invention
Пροизвοдные аρилсульφοκислοτ οбшей φορмулы:Derived aromatic sulfate of general formula:
где Κ1 = Η, СΗ3, СΙ, Ы02; З?2 = Η, 0Η, С00Κ;where Κ 1 = Η, СΗ 3 , СΙ, Ы0 2 ; H? 2 = Η, 0Η, С00Κ;
Κ3 = Η, СΗ3, СΙ, 0Η, ЫΗСС0СΗ3,ЫΚ2; Κ4 = Κ, СΟΟΗ, Ы02; Κ^Κ5 = -(Ш)4-; Η5 = Η; κ° = ыκ2-сн2- ' ΝΗ(СπΗ2π+Ι* 2. ы(СπΗ2π+Ι>3, где π=2-Κ 3 = Η, СΗ 3 , СΙ, 0Η, ΗΗСС0СΗ 3 , ΚΚ 2 ; Κ 4 = Κ, СΟΟΗ, Ы0 2 ; Κ ^ Κ 5 = - (Ш) 4 -; Η 5 = Η; κ ° = yκ 2 -sn 2 - ' ΝΗ (С π Η 2π + Ι * 2. s (С π Η 2π + Ι> 3, where π = 2-
ш2?сн-φ^δ ΝС 2' ΝΗ2- <2> - 02ΝΗ-ρ-ΝΚ2; сн2οн ΝΗw 2? sn-φ ^ δ ΝC 2 'ΝΗ 2 - <2> - 0 2 ΝΗ-ρ-ΝΚ 2 ; sun 2 on ΝΗ
ΗΝч | , где π =1-3; ЫΗ2(СΗ2)ПС00Η, где π =3-5,ΗΝh | where π = 1-3; ΗΗ 2 (СΗ 2 ) П С00Η, where π = 3-5,
00
а τаκже гуанидиκ; мοчевина; τиοмοчевина^ προявлягощие гиποглиκе- мичесκую аκτивнοсτь.
and also guanidice; urea; Thiourea is a potent hypo-glycemic activity.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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RU5018466/04911127 | 1991-11-27 | ||
SU5018466/04A RU1838296C (en) | 1991-11-27 | 1991-11-27 | Derivatives of aryl sulfo acids having hypoglycemia activity |
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WO1993011101A1 true WO1993011101A1 (en) | 1993-06-10 |
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PCT/RU1992/000219 WO1993011101A1 (en) | 1991-11-27 | 1992-11-27 | Derivatives of arylsulphoacids having hypoglycemic activity |
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WO (1) | WO1993011101A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2870742A1 (en) * | 2004-05-28 | 2005-12-02 | Expanscience Laboratoires Sa | USE OF ALKYL FURANS FOR THE PREPARATION OF A MEDICAMENT FOR THE TREATMENT OF DIABETES, OBESITY AND FOR THE COSMETIC TREATMENT OF CELLULITE AND OVERLOAD |
WO2007076875A3 (en) * | 2006-01-06 | 2007-11-15 | Univ Aarhus | Compounds acting on the serotonin transporter |
CN107793334A (en) * | 2017-09-27 | 2018-03-13 | 九江善水科技股份有限公司 | Aryl sulfonic acid ammonium salt compound, its preparation method and application |
Citations (3)
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SU530879A1 (en) * | 1975-03-10 | 1976-10-05 | Московский Ордена Ленина И Ордена Трудового Красного Знамени Государственный Университет Имени М.В.Ломоносова | Potassium sec-alkyl sulphonates as surfactants |
SU740757A1 (en) * | 1978-04-17 | 1980-06-15 | Институт Ботаники Ан Литовской Сср | 1-(2-chloroethoxycarbonylmethyl)-naphthalenesulfoacid calcium salt as control agent for potato nodule growth and formation |
SU1293175A1 (en) * | 1984-10-17 | 1987-02-28 | Калининский Государственный Университет | P-toluenesulfonates 2-(alkanoyloxy)-ethyldimethylammonium as antistatic agent |
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1991
- 1991-11-27 RU SU5018466/04A patent/RU1838296C/en active
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1992
- 1992-11-27 WO PCT/RU1992/000219 patent/WO1993011101A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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SU530879A1 (en) * | 1975-03-10 | 1976-10-05 | Московский Ордена Ленина И Ордена Трудового Красного Знамени Государственный Университет Имени М.В.Ломоносова | Potassium sec-alkyl sulphonates as surfactants |
SU740757A1 (en) * | 1978-04-17 | 1980-06-15 | Институт Ботаники Ан Литовской Сср | 1-(2-chloroethoxycarbonylmethyl)-naphthalenesulfoacid calcium salt as control agent for potato nodule growth and formation |
SU1293175A1 (en) * | 1984-10-17 | 1987-02-28 | Калининский Государственный Университет | P-toluenesulfonates 2-(alkanoyloxy)-ethyldimethylammonium as antistatic agent |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2870742A1 (en) * | 2004-05-28 | 2005-12-02 | Expanscience Laboratoires Sa | USE OF ALKYL FURANS FOR THE PREPARATION OF A MEDICAMENT FOR THE TREATMENT OF DIABETES, OBESITY AND FOR THE COSMETIC TREATMENT OF CELLULITE AND OVERLOAD |
WO2005117856A1 (en) * | 2004-05-28 | 2005-12-15 | Laboratoires Expanscience | Use of furan alkyl for preparing an antidiabetic drug |
CN1960722B (en) * | 2004-05-28 | 2010-09-08 | 科学发展实验室 | Use of furan alkyl for preparing an antidiabetic drug |
WO2007076875A3 (en) * | 2006-01-06 | 2007-11-15 | Univ Aarhus | Compounds acting on the serotonin transporter |
CN107793334A (en) * | 2017-09-27 | 2018-03-13 | 九江善水科技股份有限公司 | Aryl sulfonic acid ammonium salt compound, its preparation method and application |
Also Published As
Publication number | Publication date |
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RU1838296C (en) | 1995-12-20 |
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