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FI95566B - Förfarande för framställning av terapeutiskt aktiva fenylguanidinderivat - Google Patents

Förfarande för framställning av terapeutiskt aktiva fenylguanidinderivat Download PDF

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Publication number
FI95566B
FI95566B FI925871A FI925871A FI95566B FI 95566 B FI95566 B FI 95566B FI 925871 A FI925871 A FI 925871A FI 925871 A FI925871 A FI 925871A FI 95566 B FI95566 B FI 95566B
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formula
group
carbon atoms
biphenylyl
give
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FI925871A
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Finnish (fi)
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FI925871A (sv
FI925871A0 (sv
FI95566C (sv
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Balasubramanian Gopalan
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Boots Co Plc
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Publication of FI925871A0 publication Critical patent/FI925871A0/sv
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/16—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C261/00—Derivatives of cyanic acid
    • C07C261/04—Cyanamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/42—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms

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Claims (2)

1. Förfarande för framställning av terapeutiskt aktiva fenylguanidinderivat med formeln I -rOC ,"2 u) N=C B % 10 och deras farmaceutiskt godtagbara salter, i vilken formel Rx är fenyl, som eventuellt är substltuerad med halogen, alkyl med 1-3 kolatomer, alkoxl med 1-3 kolatomer, alkanoyl med 2-4 kolatomer, 3-metansulfonyl, 4-metansul-15 fonyl eller med en grupp med formeln S(0)nRe, väri n är O eller 1 och R8 är en alkylgrupp med 1-3 kolatomer; R2 är en grupp med formeln II Rs • ö (II) —N
20 R7 väri R6 och R7, vilka är samma eller olika, är H eller en alkylgrupp med 1-4 kolatomer; R3 är H eller en oförgrenad eller förgrenad alifatisk grupp 25 med 1-4 kolatomer; R4 är (a) H, (b) en oförgrenad eller förgrenad alifatisk grupp med 1-6 kolatomer och eventuellt substltuerad med hydroxi eller ett acylerat derivat därav, med en alkoxi-grupp med 1-3 kolatomer, med en alkyltiogrupp med 1-3 30 kolatomer, med en eventuellt alkylerad aminogrupp, med en : karbocyklisk grupp med 3-7 kolatomer, med pyridyl eller med cyan, (c) en karbocyklisk grupp med 3-7 kolatomer och eventuellt substltuerad med hydroxi, under förutsätt-ning, att R3, R4, R6 och R7 icke samtliga är metylgrupper, 35 när R7 är fenyl; ai r - a«:t 11« 1.1 l m . : 95566 eller gruppen R2 och gruppen R3 bildar tillsammans med kol-och kväveatomerna, vid vilka de är bundna, en heterocyk-lisk ring med formeln IV Rn 5 |n /»“Λ =C E UV) 10 * väri R4 är säsom ovan definierats förutom att R4 icke kan vara H, och väri Rn är H eller en alkylgrupp med 1 eller 2 kolatomer, och E är en alkylengrupp med 2-4 kolatomer och eventuellt substituerad med en eller flera alkylgrup-15 per med 1-3 kolatomer; eller R3 och R4 bildar tillsammans med kväveatomen, vid vilken de är bundna, en heterocyklisk ring med formeln V 20 (V) väri G är en alkylengrupp med 4-6 kolatomer, eventuellt avbruten av syre, svavel, sulfinyl, sulfonyl, eller kväve som eventuellt är substituerad med (a) en karbocyklisk . 25 grupp med 3-7 kolatomer, (b) en metylsulfonylgrupp eller (c) en alkylgrupp med 1-3 kolatomer och eventuellt substituerad med hydroxi eller en alkoxigrupp med 1-3 kolatomer, varvid nämnda alkylengrupp eventuellt substi-tuerats med (a) en eller flera alkylgrupper med 1-3 kol-30 atomer och eventuellt substituerade med hydroxi, (b) en : eller flera hydroxigrupper eller en ester därav, (c) en eller flera alkoxigrupper, (d) oxo eller ett derivat därav (t. ex. en oxim eller oximeter) eller (e) en eller flera grupper med formeln S(0)BR8, väri m = 0 eller 1 och Re är en 54 95566 alkylgrupp med 1-3 kolatomer, eller G är en grupp -CH2-CH=CH-(CH2)2- eller -(CH2)2CH[CON(CH3)2] (CH2)2-, och R5 är H eller en eller flera eventuella substltuenter ur gruppen halogen, en alkylgrupp med 1-4 kolatomer, en 5 alkoxigrupp med 1-3 kolatomer, trlfluormetyl och grupper med formeln S(0)BR8, väri m är 0, 1 eller 2 och Re är en alkylgrupp med 1-3 kolatomer; kännetecknat därav, att det omfattar ett steg, vid vilket man
10 A) omsätter en aminofenylförening med £ormeln VI Rs_0C <vi> ^Nih2 15 med en amid eller urea med formeln R2.CO.NR3R4 i närvaro av ett kondenseringsmedel, B) omsätter en förening med formeln XII Rs-|JjC ,SMe (XII. • ^^N=CwR,4 R15 , 25 väri R14 och R15 är H (eventuellt i form av ett sait), med en diamin med formeln R11NHENHR4, för erhällande av en förening med formeln I, väri R2 och R3 bildar tillsammans med koi- och kväveatomerna, vid vilka de är bundna, en ring med formeln IV,
30 C) omsätter en aminofenylförening med formeln VI ’ (eventuellt i form av ett sait) med en cyanförening med formeln R2CN för erhällande av en förening med formeln I, * väri NR3R4 är NH2, D) omsätter en aminofenylförening med formeln VI 35 (eventuellt i form av ett sait) med en cyanamidförening il tt'> lltfl hii ! 55 9 5 5 6 6 med formeln R3R4NCN för erhällande av en förening med for-meln I, väri R2 är NH2, E) omsätter en förening med formeln XIV 5 r^r.Rl Rs-ί— Il (XIV) l^NHCN med ett amin med formeln NHR3R4 för erhällande av en före-10 ning med formeln I, väri R2 är NH2, eller F) för erhällande av en förening med formeln I, väri R6 är alkyl, omsätter en förening med formeln XII
15 R5 /SMe (XII) N'r R15 väri R14 är gruppen R6 och R15 är gruppen R7, med en amin 20 med formeln NHR3R4 för erhällande av en förening med formeln I, väri R2 är gruppen NR6R7.
2. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer N-( 2-bifenyly- 1)-4-hydroxipiperidin-l-karboxiamidin,N-(4'-fluor-2-bife-25 nylyl)-4-hydroxipiperidin-l-karboxiamidin eller N-(5-fluor-2-bifenylyl)-4-hydroxipiperidin-l-karboxiamidin. -«
FI925871A 1990-05-17 1992-12-23 Förfarande för framställning av terapeutiskt aktiva fenylguanidinderivat FI95566C (sv)

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IN126BO1990 1990-05-17
IN126BO1990 IN172842B (sv) 1990-05-17 1990-05-17
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GB909014456A GB9014456D0 (en) 1990-06-28 1990-06-28 Therapeutic agents
EP9100911 1991-05-15
PCT/EP1991/000911 WO1992000273A1 (en) 1990-05-17 1991-05-15 Orthosubstituted biphenyl amidine and biphenyl guanidine derivatives and antidiabetic or hypoglycaemic agents containing them

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JPH089589B2 (ja) 1996-01-31
CZ280182B6 (cs) 1995-11-15
CA2041846A1 (en) 1991-11-18
NO924783L (no) 1993-02-23
MX25770A (es) 1994-03-31
PT97700A (pt) 1992-02-28
NZ238119A (en) 1993-07-27
AU7639491A (en) 1991-11-21
PL167657B1 (pl) 1995-10-31
HRP930699A2 (en) 1995-06-30
FI925871A (sv) 1992-12-23
HUT57710A (en) 1991-12-30
DE69104041T4 (de) 1995-07-27
IE64485B1 (en) 1995-08-09
BG61260B1 (en) 1997-04-30
WO1992000273A1 (en) 1992-01-09
DE69104041D1 (de) 1994-10-20
ATE111445T1 (de) 1994-09-15
JPH05507686A (ja) 1993-11-04
ES2064103T3 (es) 1995-01-16
FI925871A0 (sv) 1992-12-23
GB2244486B (en) 1994-01-26
GB9110306D0 (en) 1991-07-03
EP0536151B1 (en) 1994-09-14
RU2099323C1 (ru) 1997-12-20
NO179204C (no) 1996-08-28
IL98029A (en) 1995-10-31
CN1072173A (zh) 1993-05-19
FI95566C (sv) 1996-02-26
AU637695B2 (en) 1993-06-03
US5302720A (en) 1994-04-12
DE69104041T2 (de) 1995-02-02
HU911650D0 (en) 1991-11-28
HU210200B (en) 1995-02-28
IE911439A1 (en) 1991-11-20
GB2244486A (en) 1991-12-04
NO179204B (no) 1996-05-20
CS133491A3 (en) 1992-02-19
EP0536151A1 (en) 1993-04-14
IN172842B (sv) 1993-12-11
NO924783D0 (no) 1992-12-10
PL297374A1 (sv) 1992-07-13
BG97221A (bg) 1993-12-24
CN1028521C (zh) 1995-05-24
PT97700B (pt) 1998-08-31
KR920005714A (ko) 1992-04-03
DK0536151T3 (da) 1995-02-20

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