FI87782B - Foerfarande foer framstaellning av terapeutiskt anvaendbara kondenserade bens(tio)amider - Google Patents

Foerfarande foer framstaellning av terapeutiskt anvaendbara kondenserade bens(tio)amider Download PDF

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FI87782B
FI87782B FI853178A FI853178A FI87782B FI 87782 B FI87782 B FI 87782B FI 853178 A FI853178 A FI 853178A FI 853178 A FI853178 A FI 853178A FI 87782 B FI87782 B FI 87782B
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group
atom
carbon atoms
straight
general formula
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FI853178A
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FI853178L (fi
FI853178A0 (fi
FI87782C (sv
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Masaaki Toda
Tumoru Miyamoto
Yoshinobu Arai
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Ono Pharmaceutical Co
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Priority claimed from JP59172570A external-priority patent/JPS6150977A/ja
Priority claimed from JP59243412A external-priority patent/JPS61143371A/ja
Priority claimed from JP59246363A external-priority patent/JPS61126061A/ja
Application filed by Ono Pharmaceutical Co filed Critical Ono Pharmaceutical Co
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    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/29—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/56—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/64—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/51—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (7)

1. Förfarande för framställning av terapeutlskt användbara kondenserade bens(tlo)amlder med den allmänna 5 formeln R1-A r2 IBJ (I) 10 \ 4 där symbolen A betecknar en enkel blndnlng eller gruppen metylen, etylen, trimetylen, tetrametylen, vinylen, prope- 15 nyIen, butenylen, butadienylen eller etinyliden, vilka valfritt som substituent innehäller en, tvä eller tre rak-kedjade eller förgrenade alkylgrupper med 1-10 kolatomer och/eller fenylgrupper, symbolen B betecknar 20 en karbocyklisk ring, som innehäller 4-8 medlem- mar, vilka icke bar ersatts, eller en, tvä eller tre val-fria kolatomer är ersatta med en syre-, kväve- och/eller svavelatom (atomer), varvid ringen valfritt som substituent kan innehälla en oxo-, tioxo- och/eller hydroxigrupp 25 (grupper), symbolen T betecknar en syreatom eller en svavelatom, R1 betecknar en grupp med den allmänna formeln 30 (i) Rs/ 35 iw 87782 (ii) eller 5 (iii) »·» 10 (iv) en rakkedjad eller förgrenad alkyl-, alkenyl- eller alklnylgrupp med 1-20 kolatomer, varvid R5 och R6 obe-roende av varandra betecknar en väteatom eller en halogen-atom eller en rakkedjad eller förgrenad alkyl-, alkenyl-eller alklnylgrupp, som lnnhdller 1-20 kolatomer, vllka 15 leke har ersatts, eller en, tvd, tre, fyra eller fem val-frla kolatomer är ersatta med en syreatom (atomer), en svavelatom (atomer), en halogenatom (atomer), en kväveatom (atomer), en bensenring (rlngar), en tlofenring (rlngar), en naftalenring (rlngar), en karbocykllsk ring (rlngar), 20 en naftalenring (rlngar), en karbocykllsk ring (rlngar) med 4-7 kolatomer, en karbonylgrupp (grupper), en karbo-nyloxlgrupp (grupper), en hydroxlgrupp (grupper), en kar-boxlgrupp (grupper), en azidogrupp (grupper) och/eller en nltrogrupp (grupper),
25 R2 betecknar en väteatom eller en rakkedjad eller förgrenad alkylgrupp med 1-6 kolatomer, R3 betecknar en väteatom, en halogenatom, en hydroxlgrupp, en nltrogrupp, en grupp med den allmänna formeln -C00R7, där R7 betecknar en väteatom eller en rakkedjad eller för-30 grenad alkylgrupp med 1-6 kolatomer eller en rakkedjad eller förgrenad alkyl-, alkoxl- eller alkyltlogrupp med 1-6 kolatomer, R4 betecknar en grupp med formeln 1 151 8 7 7 8
2 -U-(CH-) -COOR8 1 n N—N -u-(CH7) -V || m \n_m H 5 -(CH,) -COOR8 ^ p eller N—N -<ch2' Λ * * q N—N
10 H där symbolen U betecknar en syreatom eller en svavelatom, R8 betecknar en väteatom eller en rakkedjad eller förgrenad alkylgrupp med 1-6 kolatomer, n och m betecknar ett hel-tal 1 - 10, och p och q betceknar noil eller ett heltal 15 1 - 10, kännetecknat därav, att (1) en syra med den allmänna formeln R1-A-COOH (II) 20 där alla symboler betecknar samma som ovan anförts, eller motsvarande ditiosyra och en förening, som har den allmänna formeln „3 1 2 3 4 5 6 35 JO I (III) 2 HN 3 '2 (B . 4 R 5 där alla symboler betecknar samma som ovan anförts, om- 6 sätts med varandra, varvid blldas en amidbindning; och ytterligare, om sä önskas, utförs förtvälning och/eller esteriflerlng, eller (2) för framställning av sädana kondenserade bens(tio)ami-der med formeln (I), som har den allmänna formeln 152 87782
3 Τ (^Λ\ (Ia) c * 2 V ^
4. Förfarande enligt alternativet (b) i patentkravet 1, kännetecknat därav, att reaktionen 35 utförs vid en temperatur av 0 - 40eC. 154 8 7 7 8 2
5. Förfarande enligt alternativet (c) i patentkra-vet 2, kännetecknat därav, att reaktionen utförs vid en temperatur av 0 - 40eC.
5 H 1 OH där alla symboler betecknar samma som definierats 1 sam-band med formeln (I), och en förenlng, som har den allmän-10 na formeln (VI) ,10-^20.0001,.50 (V1) X20 15 eller x COOR υ (VII) 20 där X10 och X20 betecknar halogenatomer, R50 betecknar en rakkedjad eller förgrenad alkylgrupp med 1-6 kolatomer och R20 betecknar en metylengrupp eller en enkel bindning, med varandra, och ytterligare, om sä önskas, utförs för-tvälning och/eller esterlflerlng. 25 2. Förfarande enligt förfarandealternativet (1) i patentkravet 1, kännetecknat där av, att reak-tionen för blldnlng av amidbindningen utförs genom att använda (a) en bland-syraanhydrid, (b) en syrahalogenid eller (c) dicyklohexylkarbodiimid (DCC). 30 3. Förfarande enligt alternativet (a) i patentkra vet 2, kännetecknat därav, att reaktionen utförs vid en temperatur av 0 - 40eC.
5. Vjx . N —N Xr20_ ^N_N H där R20 betecknar en metylengrupp eller en enkel bindnlng och de övrlga symbolerna betecknar saitana som definierats 1 10 samband med formeln (I), omsätts en förening, som har den ällinänne formeln R3
15. JL loi <iv> R -A 12 R ^Nr^-cn 20 där R20 betecknar samma som ovan och de övrlga symbolerna betecknar samma som definierats 1 samband med formeln (I), och en azid med varandra, eller (3) för framställning av sÄdana kondenserade bens(tio)ami-der, som har den allmänna formeln
25 R3 H 1 I O>N^\_20 55
30 NR -C00R där R20 betecknar en metylengrupp eller en enkel bindnlng, R55 betecknar en väteatom eller en rakkedjad eller förgre-nad alkylgrupp med 1-6 kolatomer och de övrlga symboler-35 na betecknar samma som definierats 1 samband med formeln (I), omsätts en förening, som har formeln 87782 153 R3 ^-Α^Ν'^ΟΗ (V)
6. Förfarande enligt förfarandealternativet (2) i 5 patentkravet 1, kännetecknat därav, att reaktionen utförs under vattenfria förh&llanden medelst an-vändning av t.ex. natrium-, litium- eller kaliumazid i närvaro av en svag syra, säsom pyridiniumklorid, ammonium-klorid eller dimetylanilinhydroklorid i ett inert orga- 10 niskt lösningsmedel, säsom dimetylformamid eller N-metyl-pyrrolidon, under upphettning.
7. Förfarande enligt förfarandealternativet (3) i patentkravet 1, kännetecknat därav, att reaktionen utförs under vattenfria förhällanden i närvaro av 15 ett kondenserande medel, säsom kaliumkarbonat eller nat-riumkarbonat, i ett inert organlskt lösningsmedel, säsom aceton, metyletylketon eller dioxan, under upphettning.
FI853178A 1984-08-20 1985-08-19 Förfarande för framställning av terapeutiskt användbara kondenserade b ens(tio)amider FI87782C (sv)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP17257084 1984-08-20
JP59172570A JPS6150977A (ja) 1984-08-20 1984-08-20 新規な縮合ベンズ（チオ）アミド、それらの製造方法およびそれらを有効成分として含有する薬剤
JP24341284 1984-11-20
JP59243412A JPS61143371A (ja) 1984-11-20 1984-11-20 新規な縮合ベンズ（チオ）アミド
JP59246363A JPS61126061A (ja) 1984-11-22 1984-11-22 アリールカルバモイル化合物
JP24636384 1984-11-22

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FI853178A0 FI853178A0 (fi) 1985-08-19
FI853178L FI853178L (fi) 1986-02-21
FI87782B true FI87782B (fi) 1992-11-13
FI87782C FI87782C (sv) 1993-02-25

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US (5) US4780469A (sv)
EP (2) EP0463638B1 (sv)
KR (1) KR920006237B1 (sv)
AT (2) ATE97897T1 (sv)
AU (1) AU579398B2 (sv)
CA (1) CA1261835A (sv)
DE (2) DE3588025T2 (sv)
DK (1) DK174022B1 (sv)
ES (4) ES8609217A1 (sv)
FI (1) FI87782C (sv)
GR (1) GR852014B (sv)
HU (1) HU208133B (sv)
IE (1) IE64552B1 (sv)
NO (1) NO159447C (sv)
PT (1) PT80986B (sv)
YU (4) YU45002B (sv)

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EP0463638B1 (en) 1995-05-24
EP0173516A3 (en) 1986-12-30
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AU579398B2 (en) 1988-11-24
NO159447C (no) 1988-12-28
HU208133B (en) 1993-08-30
EP0173516B1 (en) 1993-12-01
US5459134A (en) 1995-10-17
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DE3587671D1 (de) 1994-01-13
NO159447B (no) 1988-09-19
KR870002129A (ko) 1987-03-30
DK375385A (da) 1986-02-21
DE3588025D1 (de) 1995-06-29
US4939141A (en) 1990-07-03
YU144887A (en) 1988-02-29
ATE97897T1 (de) 1993-12-15
ES552747A0 (es) 1987-04-01
NO853261L (no) 1986-02-21
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ATE123019T1 (de) 1995-06-15
FI853178L (fi) 1986-02-21
ES8609217A1 (es) 1986-09-01
DE3588025T2 (de) 1995-10-19
PT80986B (pt) 1988-01-22
DK375385D0 (da) 1985-08-19
IE64552B1 (en) 1995-08-23
DE3587671T2 (de) 1994-04-21
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EP0463638A1 (en) 1992-01-02
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AU4646285A (en) 1986-03-27
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US4847275A (en) 1989-07-11
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