SI9700176A - Novi derivati kumarina, postopki za njihovo pripravo in njihova uporaba - Google Patents

Novi derivati kumarina, postopki za njihovo pripravo in njihova uporaba Download PDF

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SI9700176A
SI9700176A SI9700176A SI9700176A SI9700176A SI 9700176 A SI9700176 A SI 9700176A SI 9700176 A SI9700176 A SI 9700176A SI 9700176 A SI9700176 A SI 9700176A SI 9700176 A SI9700176 A SI 9700176A
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nhch
formula
coumarin
coumarin derivatives
co2c
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Mladen Trkovnik
Zrinka Ivezi
Ljerka Polak
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PLIVA, farmaceutska, kemijska, prehrambena i kozmeti�ka
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    • 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
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
    • 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
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
    • 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
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Opisani izum se nanaša na nove derivate kumarina s splošno formulo I , kjer je R1=NH2 ali -NHCH=C(CO2C2H5)2, R2=R3=R4=H,R5=F; R1=R3=NHCH= C(CO2C2H5 )2, R2=R4=R5=H; R1=H ali OH, R3=NHCH=C(CO2C2H5) 2, R2=R4=R5=H; R1=OH, R2=R3=R4=H, R5=-NHCH=C(CO 2C2H5)2; R1=R3=R5=H, R2=CH3 ali CF3, R4=-NHCH=C(CO2C2H5)2 in postopke za njihovo pripravo ter njihovo uporabo kot intermediatov za sintezo novih derivatov kumarina s potencialnim biološkim delovanjem.ŕ

Description

PLIVA, farmaceutska, kemijska, prehrambena i kozmetička industrija, dioničko društvo
Novi derivati kumarina, postopki za njihovo pripravo in njihova uporaba
Področje tehnike, v katero spada izum: MPK CO7D311.
Predloženi izum se nanaša na nove derivate kumarina s splošno formulo I
kjer je
R' = NH2 ali -NHCH=C(CO3C2Hs)2, R2 = R3 = R4 - H, R5 = F
R1 = R3 = NHCH=C(CO2C2H5)2, R2 = R4 = R5 = H
R' = H ali OH, R3 = NHCH=C(CO2C2H5)2, R2 = R4 = R5 = H
R1 = OH, R2 = R3 = R4 = H, R5 = -NHCH=C(CO,C2H-),
Ri = R' = rs = H, R2 = CH, ali CF3, R4 = -NHCH=C(CO,C2H5)2.
V skladu s predloženim izumom nove derivate kumarina s splošno formulo 1 pripravimo iz substituiranih kumarinov s formulo II
II kjer je
R1 = R3 = R4 = R5 = H R2 = Nn2
R1 = R3 = NH2, R2 = R4 = R5 = H
R' = OH, R2 = R4 = Rs = H, R3 = NH2
R1 = OH, R2 = R3 = R4 = H, R5 = NH2
R1 = NH2, R2 = R3 = R4 = H, R5 = F
Ri = R3 = r5 = h, R2 = CH3 ali CF3, R4 = NH2, z reakcijo z dietil-etoksimetilen malonatom s formulo III
C2H5OCH=C(CO2C2H5)2
III pri temperaturi 120°C v času od 10 minut do 27 ur, pri čemer dobimo malonatne estre kumarina s splošno formulo I s substituenti, označenimi pred tem.
Izhodni substituirani amino kumarini s splošno formulo II, razen spojine, označene s tem, da je R1 = NH2, R2 = R3 = R4 = H, R^ = F. so že opisani v literaturi: F. W. Linch, J. Chem. Soc. 101 (1912) 1758; G. T. Morgan. F. M. G. Micklethvvait, J. Chem. Soc. 85 (1904) 1230; G. Kokotos, C. Tzougraki. J. Heterocyclic Chem. 23 (1986) 87; I. C. Ivanov. S. K. Karagiosov, I. Manolov, Arch. Pharm. (Weinheim) 324 (1991) 61.
Novi derivati kumarina s splošno formulo I so uporabni intermediati za sintezo novih derivatov kumarina s potencialnim biološkim delovanjem, kot je antimikrobno. antitumorsko in antivirusno delovanje.
Postopek je ponazorjen z naslednjimi primeri, ki na noben način ne omejujejo obsega izuma.
PRIMER 1
3-amino-8-fluorkumarin
IV
Raztopino 3-acetilamino-8-fluorkumarina (3,00 g; 0,014 mol) v koncentrirani žveplovi kislini (2,65 g, 0,027 mol) segrevamo 1 uro pri 75-80°C. Ohlajeno raztopino zlijemo ob mešanju na zmes ledu in vode in jo naalkalimo z nasičeno vodno raztopino NaHCO3 do pH = 6, nato pa pustimo, da se obori pri +4°C. Dobljeni 3-amino-8-fluorkumarin prekristaliziramo iz 50% etanola (1,63 g; 67%). Tal.: 173174°C.
Analiza:
izračunano za C9H6F3NO2: C = 60,34; H = 3,38; N = 7,82.
ugotovoljeno: C = 59,97; H = 3,22: N = 7,72.
‘H-NMR (DMSO-d6). S/ppm: 5,9 (s, NH2), 6,7 (s, H4); 7.1 - 7,2 (m, H5 - H7). m/z: 178 (M'), 151,141,134,127.
PRIMER 2
Dietil-{[(2-okso-2H-[l]-benzopirano-6-il)amino]metilen} malonat
H5C2OOC
H5C2OOC
V
Raztopino 6-aminokumarina (2,00 g; 0,012 mol) v dietil-etoksimetilen malonatu (3,03 g: 0,014 mol) segrevamo 10 minut pri I2O°C, pri čemer se reakcijska zmes strdi. Nastalo svetlo rjavo oborino dietil -{[(2-okso-2H-[l]-benzopirano-6-il)aminoj metilen} malonata (3,95 g; 96%) prekristaliziramo iz etanola. Tak: 141 -142°C.
Analiza:
izračunano za C1?H17NO6: C = 61,62; H = 5,17; N = 4,23.
ugotovljeno: C = 61,87; H = 4,99; N = 4,17.
‘H-NMR (DMSO-d6). δ/ppm: 1,3 (t, CH3), 4,3 (q, CH,): 6,6 (d; H3); 7,7 (d, H8); 7,9 (d, H7). 8,5 (d; H5); 10.0 (d; H4); 12,4 (bs, NH).
PRIMER 3
Tetraetil-{[(2-okso-2H-[l]-benzopirano-3,6-diil)diamino]dimetilen} malonat
HsCsOOCH5C2OOC
C=C — / H
Pripravljen po postopku, opisanem v primeru 2, izhajajoč iz 3,6-diaminokumarina (1,00 g; 5,676 mmol) in dietil-etoksimetilen malonata (2,81 g; 0,013 mol). Trajanje reakcije: 6 ur. S prekristalizacijo iz etanola dobimo rumeno zelene kristale tetraetil{[(2-okso-2H-[l]-benzopirano-3,6-diil)diamino]dimetilen} malonata (2,55 g; 87%). Tak: 131-134°C.
Analiza:
izračunano za C25H28N,O10: C = 58,13; H = 5,46; N = 5,43.
ugotovljeno: C = 57,74; H — 5,19; N = 5,40.
‘H-NMR (DMSO-dJ. δ/ppm: 1,2 (t, CH3), 4,2 (q, CH2); 7.4 (m, C H), 7,6 (s, H5); 7,9 (s: Η4): 8,2-8,5 (m: H7-H8); 10,6-10.8 (m: 2NH).
PRIMER 4
Dietil-T [(3-hidroksi-2-okso-2H-[ l]-benzopirano-6-il)amino]metilen} malonat
H5C2OOC
H5C2OOC
VII
Pripravljen po postopku, opisanem v primeru 2. izhajajoč iz 6-amino-3hidroksikumarina (0,88 g, 4,967 mmol). Trajanje reakcije: 1 uro. Rumeno rjavo oborino dietil-{[(3-hidroksi-2-okso-2H-[l]-benzopirano-6-il)amino]metilen} malonata, nastalo s hlajenjem raztopine, prekristaliziramo iz ledocta (1,52 g; 88%).
Analiza:
izračunano za C17H17NO_: C = 58,79; H = 4,93; N = 4,03.
ugotovljeno: C = 58,64; H = 4,64; N = 4,25.
‘H-NMR (DMSO-d6). S/ppm: 1,3 (t, CH3), 4,2 (q, CH2); 7,1-8,4 (m; Ar H); 10,5 (s:
NH); 10,8 (d; OH).
m/z: 347 (M+), 302,149, 79, 61, 45, 43.
PRIMER 5
Dietil-{[(3-hidroksi-2-okso-2H-[l]-benzopirano-8-il)amino]metilen} malonat
Vlil
Pripravljen po postopku, opisanem v primeru 2. izhajajoč iz S-amino-3hidroksikumarina (1,93 g, 0,011 mol). Trajanje reakcije: 4 ure. S prekristalizacijo iz ledocta se obori dietil-{[(3-hidroksi-2-okso-2H-[ 1 ]-benzopirano-8iljaminojmetilen} malonat, v obliki rjavih sijajnih ploščičastih kristalov (3,37 g; 89%).
Analiza:
izračunano za C[7H17NO7: C = 58,79; H = 4,93: N = 4,03.
ugotovljeno: C = 58,98; H = 4,89; N = 3,91.
*H-NMR (DMSO-dJ. S/ppm: 1,3 (t, CH3), 4,2 (q, CH.): 7,1-8,5 (m; Ar H); 10,7 (s; NH); 11,1 (d; OH).
m/z: 347 (M+), 302, 273,199,177, 70, 61, 47.
PRIMER 6
Dietil-{[(8-lluor-2-okso-2H-[lj-benzopirano-3-il)amino]metilen} malonat .00002H5
\
OOOC2H5 (X
Pripravljen po postopku, opisanem v primeru 2. izhajajoč iz 3-amino-8fluorkumarina (2,00 g, 9,250 mmol). Trajanje reakcije: 5 ur. S hlajenjem raztopine se obori svetlo rumeni dietil-{[(8-fluor-2-okso-2H-[ 1 j-benzopirano-3iljaminojmetilen} malonat, ki ga prekristaliziramo iz etanola (2,76 g; 95%). Tal.: 175-177°C.
Analiza:
izračunano za C,7H., FNO,: ugotovljeno:
C = 58.45; H = 4,62: N = 4,01.
C = 58,38 H = 4,46; N = 3,98.
PRIMER 7
Dietil-{[(4-metil-2-okso-2H-[l]-benzopirano-7-il)amino]metilen}- malonat
Pripravljen po postopku, opisanem v primeru 2, izhajajoč iz 7-amino-4metilkumarina (5,00 g, 0,029 mmol). Trajanje reakcije: 30 minut. Oborjeni dietil{[(4-metil-2-okso-2H-[l]-benzopirano-7-il)amino]metilen} malonat, prekristaliziramo iz etanola (9,70 g; 98%). Tal.: 139-140°C.
Analiza:
izračunano za C18H19NO6: C = 62,60; H = 5,55; N = 4,06.
ugotovljeno: C = 61,97 H = 5,05; N = 4,25.
PRIMER 8
Die til-{[(4-( trifluormetil-2-okso-2H-[l]-benzopirano-7-il)amino]metilen} malonat
XI
Pripravljen po postopku, opisanem v primeru 2. izhajajoč iz 7-amino-4(trifluormetil)kumarina (3,00 g, 0.015 mol). Trajanje reakcije: 27 ur. S hlajenjem se obori rumeni d i e t i 1 - {[ (4-1 r if 1 u o r m e t i I - 2 -o ks o - 2 H - [ 1 ] - b e n z o p i r a n o - 7 il)amino]metilen) malonat, ki ga prekristaliziramo iz etanola (4,83 g; 92%). Tal.: 125-I26°C.
Analiza:
izračunano za ClsH1(F3NO0: C = 54,14; H = 4.04; N = 3,51.
ugotovljeno: C = 54,12 H = 4.17; N = 3,46.
Ή-NMR (DMSO-dj S/ppm: 1,3 (t; CH,); 4,2 (q; CH2); 6,8 (s, H3), 7,4-7,6 (m; H6, H8, C H); 8,4 (d, H5); 10,7 (d; NH).
Za
PLIVA, farmaceutska, kemijska, prehrambena i kozmetička industrija, dioničko društvo

Claims (12)

1. Novi derivati kumarina s splošno formulo I označeni s tem, daje
R1 = NH2 ali -NHCH=C(CO2C2H5)2, R2 = R3 = R4 = H, R5 = F
Ri = r3 = NHCH=C(CO2C2H5)2, R2 = R4 = R5 = H
R1 = H ali OH, R3 = NHCH=C(CO2C2H5)2, R2 = R4 = R5 = H
R1 = OH, R2 = R3 = R4 = H, R5 = -NHCH=C(CO2C2H5)2
R1 = R3 = R5 = H, R2 = CH, ali CF,, R4 = -NHCH=C(CO2C2H5)2.
2. Derivat kumarina s formulo I po zahtevku 1, označen s tem, da je: R1 = NH2, R2 = R3 = R4 = H, R5 = F.
3. Derivat kumarina s formulo I po zahtevku 1, označen s tem, daje: R1 = R2 = R4 = R5 = H, R3 = -NHCH=C(CO2C2H5),.
4. Derivat kumarina s formulo I po zahtevku 1, označen s tem, daje: R2 = R4 = R5 = H, R1 = R3 = -NHCH=C(CO2C2H5)2.
5. Derivat kumarina s formulo I po zahtevku 1, označen s tem, daje: R1 = OH, R3 — -NHCH=C(CO2C2H5)2, R2 = R4 = R5 = H.
6. Derivat kumarina s formulo I po zahtevku 1. označen s tem. daje: R1 — OH, R2 = r’ = r> = h, R5 = -NHCH=C(CO,C1H-)1.
7. Derivat kumarina s formulo I po zahtevku 1. označen s tem, da je: R1 =
-NHCH=C(CO2C2H5)2, R2 = R3 = R4 = H, R5 = F.
8. Derivat kumarina s formulo I po zahtevku 1, označen s tem. daje: R' = R3 = R — H, R2 = CHV R4 = -NHCH=C(CO2C2H5)2.
9. Derivat kumarina s formulo I po zahtevku 1, označen s tem, daje: R1 = R3 = R = H. R2 = CF3, R4 = -NHCH=C(CO2C2H5)2.
1(1. Postopek za pripravo spojin s splošno formulo I po zahtevku 1, označen s tem, da spojine s splošno formulo II kjer je
R1 = R3 = R4 = R5 = H, R2 = NH2
R1 = R3 = NH2, R2 = R4 = R5 = H
R1 = OH, R2 = R4 = R5 = H, R3 = NH2
R1 = OH, R2 = R3 = R4 = H, R5 = NH2
R' = NH2, R2 = R3 = R4 = H, R5 = F
R1 = R3 = R5 = H, R2 = CH3 ali CF3, R4 = NH„ in dietil-etoksimetilen malonat s formulo III
C2H5OCH=C(CO2C2HS)2
III segrevamo pri temperaturi 120°C v času od
10 minut do 27 ur, pri čemer se s hlajenjem oborijo malonatni estri kumarina.
II. Novi derivati kumarina po zahtevku 1, označeni s tem, da so uporabni inter
11 mediati za sintezo novih derivatov kumarina s potencialnim biološkim delovanjem, kot je antimikrobno, antitumorsko in antivirusno.
12. Uporaba novih derivatov kumarina po zahtevku 1, kot uporabnih intermediatov za sintezo novih derivatov kumarina s potencialnim biološkim delovanjem, kot je antimikrobno, antitumorsko in antivirusno.
Za
PLIVA, farmaceutska, kemijska, prehrambena i kozmetička industrija, dioničko društvo:
PATENTNA PISARNA, d.o.o. LJUBLJANA, ČOPOVA 14
25877-v-97-mn
POVZETEK
Novi derivati kumarina, postopki za njihovo pripravo in njihova uporaba
Opisani izum se nanaša na nove derivate kumarina s splošno formulo I
R5 kjer je
R1 = NH2 ali -NHCH=C(CO2C2H5)2, R2 = R3 = R4 = H, R5 = F; R1 = R3 = NHCH=C(CO2C2H5)2, R2 = R4 = R5 = H;
R1 = H ali OH, R3 = NHCH=C(CO2C2H5)2, R2 = R4 = R5 = H;
R1 = OH, R2 = R3 = R4 = H, R5 = -NHCH=C(CO2C2H5)2; r1 = r3 = r5 = H, R2 = CH3 ali CF3, R4 = -NHCH=C(CO,C2H5)2 in postopke za njihovo pripravo ter njihovo uporabo kot intermediatov za sintezo novih derivatov kumarina s potencialnim biološkim delovanjem.
SI9700176A 1996-07-02 1997-07-02 Novi derivati kumarina, postopki za njihovo pripravo in njihova uporaba SI9700176B (sl)

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CZ207397A3 (cs) 1998-01-14
JPH1067768A (ja) 1998-03-10
SK282106B6 (sk) 2001-11-06
EP0816353B1 (en) 2001-12-19
DE69709252D1 (de) 2002-01-31
BA97239A (bs) 2000-11-06
DE69709252T2 (de) 2002-07-25
EP0816353A3 (en) 1998-03-04
BG63045B1 (bg) 2001-02-28
HUP9701134A3 (en) 2001-02-28
US5840922A (en) 1998-11-24
RU2135490C1 (ru) 1999-08-27
HU9701134D0 (en) 1997-08-28
ATE211136T1 (de) 2002-01-15
PL320912A1 (en) 1998-01-05
CN1170722A (zh) 1998-01-21
HUP9701134A2 (hu) 1998-12-28
HRP960308A2 (en) 1998-08-31
CA2209404A1 (en) 1998-01-02

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