FI107608B - Förfarande för framställning av en antifungal förening samt i förfarandet användbara mellanprodukter - Google Patents

Förfarande för framställning av en antifungal förening samt i förfarandet användbara mellanprodukter Download PDF

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Publication number
FI107608B
FI107608B FI910508A FI910508A FI107608B FI 107608 B FI107608 B FI 107608B FI 910508 A FI910508 A FI 910508A FI 910508 A FI910508 A FI 910508A FI 107608 B FI107608 B FI 107608B
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compound
formula
process according
reduction
triazol
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FI910508A
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English (en)
Finnish (fi)
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FI910508A0 (fi
FI910508A (fi
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Kenneth Richardson
Stephen James Ray
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Pfizer
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    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D213/60—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 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (16)

1. Förfarande för framställning av en antifungal förening med formeln
5 R1 R2 01j\/ ΛΎν1'! R y 10 väri R är fenyl, som substituerats med en tili tre substi-tuenter, av vilka var och en oberoende av varandra väljs frän gruppen halogen och -CF3; R1 är Ci-C^-alkyl; R2 är H eller C^Q-alkyl; X är CH eller N; och Y är F eller Cl, eller för framställning av dess farma-15 ceutiskt godtagbara sait, kännetecknat av att i förfarandet a) fas av en förening med formeln R1 ,n 0 Js. UI) 20 Y väri R1, R2, X och Y är säsom ovan definierats, en l'-dep-rotonerad form att reagera med en förening med formeln • · ;···; 25 7: Ύ (III) N K väri R är säsom ovan definierats; eller • · · ’ • ♦ · *·1 3 0 b) fäs en förening med formeln . · R1 R2 ? R2 y — W, • · · In. m ’ « · (IV) (VI) « · • · · • · · ♦ ·· · · • · · • · · • · 107608 väri R, R1, R2, X och Y är säsora ovan definierats och Z är en avgäende grupp, att reagera antingen med ett bassalt av 1H-1,2,4-triazol eller med lH-l,2,4-triazol i närvaro av en tillsatt bas; eller 5 c) för framställning av en förening enligt formeln I, väri X är N, reduceras en förening med formeln: R1 R2 - Λ OH y , ^ \ . N^-2 reducer ing förening enligt N N μ _x 10. jlj formel (I) , där R X är N z2 (XI) väri R, R1, R2 och Y är säsom ovan definierats och Z2 och Z3 15 väljs oberoende av varandra frän H och en grupp, som kan avlägsnas selektivt genom reducering, förutsatt att Z2 och Z3 inte bäda kan vara H; och om sä önskas omvandlas den erhällna föreningen enligt formel (I) tili sitt farma-ceutiskt godtagbara sait. 20 2. Förfarande enligt patentkrav 1, k ä n n e - tecknat av att den i förfarandealternativ a) nämnda deprotonerade formen är litium-, natrium- eller kaliumsalt av föreningen enligt formel (II).
3. Förfarande enligt patentkrav 1, k ä n n e -25 tecknat av att i förfarandealternativ b) är Z klor, • · · | brom eller C^-C^-alkansulfonyloxi . • 1 · · .···. 4. Förfarande enligt patentkrav 1, k ä n n e - • · tecknat av att i förfarandealternativ b) används • · ... föreningen enligt formel IV. * « » ' 30 5. Förfarande enligt nägot av patentkraven 1, 3 eller 4, kännetecknat av att det i förfaran- * : dealternativ b) nämnda bassaltet av 1H-1,2,4-triazol är « « · *...· antingen natrium-, kalium- eller tetra-n-butylammonium- : .·. sait. ♦ 1 1 .···. 35 6. Förfarande enligt nägot av patentkraven 1, 3 • · *11 eller 4, kännetecknat av att den i förfaran- • · • · 1 • · · ·♦· · · • · · • ·· • · 107608 dealternativ b) nämnda tillsatta basen är natrium- eller kaliumkarbonat.
7. Förfarande enligt patentkrav 1, kanne-tecknat av att i förfarandealternativ c) är Z2 en 5 grupp, som selektivt kan avlägsnas genom reducering, och Z3 är H.
8. Förfarande enligt patentkrav 1 eller 7, k ä n -netecknat av att den i förfarandealternativ c) nämnda gruppen, som selektivt kan avlägsnas genom reduce- 10 ring, är halogen, företrädesvis klor.
9. Förfarande enligt nägot av patentkraven 1, 7 eller 8, kännetecknat av att den i förfarandealternativ c) nämnda reduceringen förverkligas med hyd-rogenolys genom användning av palladium i kol som kataly- 15 sator.
10. Förfarande enligt patentkrav 9, kännetecknat av att även natriumacetat är närvarande.
11. Förfarande enligt nägot av de föregäende patentkraven, kännetecknat av att R är fenyl, 20 som substituerats med en eller tvä halogensubstituenter, företrädesvis oberoende av varandra med en eller tvä fluor- och/eller klorsubstituenter.
12. Förfarande enligt patentkrav 11, k ä n n e - .V: t e c k n a t av att R är 2 - f luorf enyl, 4 - f luorf enyl, • · 25 2,4-difluorfenyl, 2-klorfenyl eller 2,4-diklorfenyl; • · · : R1 är metyl; och • · · ♦·· · 0 .···. R2 är H. • ·
13. Förfarande enligt patentkrav 12, k ä n n e - • · ... t e c k n a t av att R är 2-f luorf enyl, 2,4-dif luorfenyl, i « I *** 30 2-klorfenyl eller 2,4-diklorfenyl; R1 är metyl; ’***· R2 är H; och O Y är F. : .·. 14. Förfarande enligt nägot av de föregäende pa- • · · ^.1/ 35 tentkraven, vilket används för f ramställning av en fö- • · *:1 rening enligt formel (I), kännetecknat av att • · • · · * · · • · · · · • · · • ·· • · 107608 R2 är H och att föreningen har en 2R, 3S-konf iguration, dvs. : R1 .H
5 I Wii K
15. Förfarande enligt patentkrav 14, kanne-tecknat av att det används för f ramställning av 10 2R,3S-2- (2,4-difluorfenyl) -3- (3-fluorpyridin-4-yl) -1- (1H- 1.2.4- triazol-l-yl)butan-2-ol, 2R,3S-2-(2-klorfenyl)-3-(3-f luorpyridin-4-yl) -1- (1H-1,2,4- triazol-l-yl) but an-2 -oi, 2R,3S-2-(2-fluorfenyl)-3-(3 -fluorpyridin-4-yl)-1-(1H- 1.2.4- triazol-l-yl) butan-2-ol, 2R,3S-2-(2,4-difluorfenyl)- 15 3-{5-fluorpyrimidin-4-yl)-1-(1H-1,2,4-triazol-l-yl)butan- 2-ol eller 2R,3S-2-(2,4-diklorfenyl)-3-(5-fluorpyrimidin-4-yl)-1-(1H-1,2,4-triazol-l-yl)butan-2-ol; eller ett far-maceutiskt godtagbart sait av dessa.
16. Förening med formeln 20 . 2 K1· R1 L y \ / Z K IC TV-1 k vV r k • · Y x/ ··2: 25 • · · dv) (vi) M» * « • · väri R, R1, R2, X och Y är säsom definierats i patentkrav • · ... 1 och Z är en avgäende grupp. * 30 17. Förening enligt patentkrav 16 med formeln VI, kännetecknad av att Z är klor, brom eller C]_- * 1 C4-alkansulfonyloxi. , · · · «1 · * · · • · • · · 7 · · • · · I • · · • · • · • · · . • · • · · • · · (·· · · 2 • · · ♦ M • · 107608
18. Förening med formeln R1 R2 OH V n γ3 <xi) 5 w 1 XJ R y z2 väri R, R1, R2, X och Y är säsom definierats i patentkrav 1 och Z2 och Z3 väljs oberoende av varandra frän H och en 10 grupp, som selektivt kan avlägsnas genom reducering, fö-rutsatt att och Z2 och Z3 inte bägge kan vara H.
19. Förening enligt patentkrav 18, kanne-tecknad av att gruppen, som selektivt kan avlägsnas genom reducering, är halogen. 15 20. Förening enligt patentkrav 19, k ä n n e - tecknad av att Z2 är klor och Z3 är H. 21. 4-etyl-5-fluorpyrimidin eller 4-klor-6-etyl-5-fluorpyrimidin. • · • · • · · • · • · · • · • » ··· • · • · t • · · • ·· « • · · • · t · • · · • · • t« • · · • · · • · • · 1 • · · 1 • · • · « • · · • · · · • ·1 • · • · »M • · • · · ft ft ft ··« · • · · • · · • ft
FI910508A 1990-02-02 1991-02-01 Förfarande för framställning av en antifungal förening samt i förfarandet användbara mellanprodukter FI107608B (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI971238A FI971238A (sv) 1990-02-02 1997-03-25 Triazol antifungala ämnen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB909002375A GB9002375D0 (en) 1990-02-02 1990-02-02 Triazole antifungal agents
GB9002375 1990-02-02

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FI910508A0 FI910508A0 (fi) 1991-02-01
FI910508A FI910508A (fi) 1991-08-03
FI107608B true FI107608B (sv) 2001-09-14

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ID=10670334

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Application Number Title Priority Date Filing Date
FI910508A FI107608B (sv) 1990-02-02 1991-02-01 Förfarande för framställning av en antifungal förening samt i förfarandet användbara mellanprodukter
FI971238A FI971238A (sv) 1990-02-02 1997-03-25 Triazol antifungala ämnen
FI20000084A FI20000084A (sv) 1990-02-02 2000-01-17 Förfarande för framställning av en antifungal farmaceutisk komposition

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FI971238A FI971238A (sv) 1990-02-02 1997-03-25 Triazol antifungala ämnen
FI20000084A FI20000084A (sv) 1990-02-02 2000-01-17 Förfarande för framställning av en antifungal farmaceutisk komposition

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US (2) US5567817A (sv)
EP (1) EP0440372B1 (sv)
JP (2) JP2625584B2 (sv)
KR (1) KR930011039B1 (sv)
CN (2) CN1026788C (sv)
AP (2) AP9000237A0 (sv)
AT (1) ATE90090T1 (sv)
AU (1) AU625188B2 (sv)
BA (1) BA97298A (sv)
BG (1) BG60032A3 (sv)
BR (1) BR9100435A (sv)
CA (2) CA2035314C (sv)
CZ (1) CZ279339B6 (sv)
DE (2) DE10299035I2 (sv)
DK (1) DK0440372T3 (sv)
EG (1) EG19750A (sv)
ES (1) ES2055523T4 (sv)
FI (3) FI107608B (sv)
GB (1) GB9002375D0 (sv)
HK (1) HK219396A (sv)
HU (2) HU205351B (sv)
IE (1) IE64774B1 (sv)
IL (2) IL110322A (sv)
IN (1) IN176148B (sv)
IS (1) IS1629B (sv)
LU (1) LU90960I2 (sv)
LV (1) LV10615B (sv)
MA (1) MA22054A1 (sv)
MX (1) MX24363A (sv)
MY (1) MY105494A (sv)
NL (1) NL300100I2 (sv)
NO (2) NO176796C (sv)
NZ (1) NZ247205A (sv)
OA (1) OA09480A (sv)
PE (1) PE31691A1 (sv)
PL (3) PL169307B1 (sv)
PT (1) PT96617B (sv)
RO (1) RO109648B1 (sv)
RU (2) RU2114838C1 (sv)
SK (1) SK278215B6 (sv)
YU (1) YU48105B (sv)
ZA (1) ZA91761B (sv)

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