FI109534B - Förfarande för framställning av farmakologiskt aktiva pyrimidinderivat - Google Patents

Förfarande för framställning av farmakologiskt aktiva pyrimidinderivat Download PDF

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FI109534B
FI109534B FI931458A FI931458A FI109534B FI 109534 B FI109534 B FI 109534B FI 931458 A FI931458 A FI 931458A FI 931458 A FI931458 A FI 931458A FI 109534 B FI109534 B FI 109534B
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pyridyl
pyrimidinamine
formula
compound
hydrogen
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FI931458A
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FI931458A (fi
FI931458A0 (fi
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Juerg Zimmermann
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Novartis Ag
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    • 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D401/14—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 three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (12)

1. Förfarande för framställning av ett farmakologiskt /•j aktivt N-fenyl-2-pyrimidinaminderivat med formeln I • · » 9 .**, 30 R7 R6 Rt ReH^~\—r5 • ^ aK oo R2_f V-V R4 " 35 >=/ 'H R3 109534 54 väri Rj betecknar en frän en ringkolatom bunden pyridyl, vars kväveatom är osubstituerad eller substituerad med syre, R2 och R3 betecknar vardera väte, R„ betecknar väte eller en lägalkyl, R5 betecknar väte, en lägalkyl eller 5 trifluormetyl, R6 betecknar väte, R7 betecknar nitro, fluor-substituerad lägalkoxi eller en rest med formeln II/ -N(R9)-C(=X)-(Y)n-R10 (II) 10 väri R9 betecknar väte, X betecknar oxo, n är 0 och R10 betecknar en alkylrest med 5-10 C-atomer, en fenylrest, som är osubstituerad eller substituerad med cyano, lägalkyl, (4-metylpiperazinyl)-lägalkyl, lägalkoxi, halogen 15 eller karboxi, en cykloalkylrest med högst 10 C-atomer, tienyl, naftyl eller frän en kolatom bunden pyridyl och R8 betecknar väte, eller för framställning av ett farma-ceutiskt användbart sait av en dylik förening, som inne-häller minst en saltbildande grupp, kännetecknat därav, 2. att ;·: : a) en förening med formeln III ·:*··: Ri |'V 25 V=0 ;*·*· R2—^ (UI) Vn'R" / \ r3 R12 30 väri Ru och R12 betecknar oberoende av varandra vardera en *.**: lägalkyl och R17 R2 ja R3 betecknar detsamma som ovan, varvid de i föreningen med formeln III förekommande funk-tionella grupperna, med undantag av de grupper som delta-.···, gar i reaktionen, vid behov är i skyddad form, eller ett 35 sait av en dylik förening omsätts med en förening med formeln IV - 55 109534 r7 Re
5 Re \ / Rs NH \-f (IV) )_/>. nh2 h 10 vari substituenterna betecknar detsamma som ovan, varvid de i formeln IV förekommande funktionella grupperna med undantag av guanidinogruppen, som deltagar i reaktionen, vid behov är i skyddad form, eller med ett salt av en dylik förening, och de förekommande skyddsgrupperna ut-15 bryts, eller b) för framställning av en förening med formeln I, vari substituenterna betecknar detsamma som ovan, med undantag av nitro och en fluor-substituerad lägalkoxi R7, en fö- ^ 20 rening med formeln V * * • « '‘V Rie Ris R, R17y-R14 - ” r3 * * · 30 väri R13 betecknar väte eller en lägalkyl, R14 betecknar ’· väte, en lägalkyl eller trifluormetyl, R15 och R17 beteck- » * · ·,,,· nar väte, R16 betecknar amino och de andra substituenterna betecknar detsamma som ovan, varvid de i föreningen med ,···, formeln V förekommande funktionella grupperna, med undan- 35 tag av aminogruppen som deltagar i reaktionen, vid behov i ! är i skyddad form, omsätts med en förening med formeln VI 109534 56 HO-C(=X)-(Y)n-R10 (VI) väri substituenterna och symbolerna betecknar detsamma som ovan, varvid de i en förening med formeln VI före-5 kommande funktionella grupperna, med undantag av gruppen HO-C(=X)- som deltagar i reaktionen, vid behov är i skyddad form, eller med ett reaktivt derivat av en förening med formeln VI och de förekommande skyddsgrupperna utbryts, eller 10 c) för framställning av en förening med formeln I, väri Rx betecknar en frän en ringkolatom bunden pyridyl, vars kväveatom är substituerad med syre, och väri de andra substituenterna och symbolerna betecknar detsamma som 15 ovan, en förening med formeln I, väri R3 betecknar en frän en ringkolatom förbunden pyridyl, omvandlas tili en N-oxidoförening med ett lämpligt oxidationsmedel, och en med nägot av förfarandena a) - c) erhällen fö-. . 20 rening med formeln I omvandlas, om sä önskas, tili sitt | farmaceutiskt användbara sait eller ett erhället sait av ··* ·’ föreningen med formeln I omvandlas tili en fri förening ···: eller tili ett farmaceutiskt användbart sait. » * « • 25 2. Förfarande enligt patentkravet 1, kännetecknat därav, : : : att utgängsämnen väljs sä, att man erhäller en förening med formeln I, väri Rj betecknar en frän en kolatom f ©Γι’. bunden pyridyl eller en N-oxido-pyridyl, R2 och R3 beteck- • · nar vardera väte, R4 betecknar väte eller en lägalkyl, R5 ·’ 30 betecknar väte, en lägalkyl eller trifluormetyl, R6 be- '· *·’ tecknar väte, R7 betecknar nitro, en fluor-substituerad lägalkoxi eller en rest med formeln II, väri R9 betecknar väte, X betecknar oxo, n är 0 och R10 betecknar en frän en ,···. kolatom förbunden pyridyl, en osubstituerad eller med ha- 35 logen, cyano, lägalkoxi, karboxi, lägalkyl eller 4-metyl-piperazinylmetyl substituerad fenyl, C5-C7-alkyl, tienyl, 2-naftyl eller cyklohexyl, och R8 betecknar väte, eller 57 109504 ett farmaceutiskt användbart sait av en dylik förening, soin innehäller minst en saltbildande grupp.
3. Förfarande enligt patentkravet 1 eller 2, kännetecknat 5 därav, att utgängsämnena väljs sä, att man erhäller en förening med formeln I, väri R4 betecknar väte och de andra resterna betecknar detsamma som i de ovan nämnda kraven, eller ett farmaceutiskt användbart sait av en dylik förening, som innehäller minst en saltbildande 10 grupp.
4. Förfarande enligt patentkravet 1 eller 2, kännetecknat därav, att utgängsämnen väljs sä, att man erhäller en förening med formeln I, väri R4 betecknar en lägalkyl och 15 de andra resterna betecknar detsamma som i de ovan nämnda kraven, eller ett farmaceutiskt användbart sait av en dylik förening, som innehäller minst en saltbildande grupp. • f. 20 5. Förfarande enligt patentkravet 1, kännetecknat därav, I att utgängsämnena väljs sä, att man erhäller en förening • · · **·'/ med formeln I, väri Rx betecknar frän en kolatom bunden ♦ · 0 ··<· pyridyl, R2, R3, R4, Rs, R6 och R8 betecknar vardera väte ' : och R7 betecknar nitro eller en rest med formeln II, väri * * · : V 25 R9 betecknar väte, X betecknar oxo, n är 0 och R10 be- .* tecknar f ran en kolatom bunden pyridyl, en osubstituerad eller med fluor, klor, cyano, lägalkoxi, karboxi, lägal- kyl eller 4-metylpiperazinylmetyl substituerad fenyl, eller det betecknar en C5-C7-alkyl, tienyl eller cyklo- * 30 hexyl, eller ett farmaceutiskt användbart sait av en * » . dylik förening, som innehäller minst en saltbildande :' grupp.
6. Förfarande enligt patentkravet 1, kännetecknat därav, > t 35 att utgängsämnena väljs sä, att man erhäller N-(3-nitrofenyl)-4-(3-pyridyl)-2-pyrimidinamin, | | 109534 58 N-[3-(4-klorbensoylamido)fenylJ-4-(3-pyridyl)-2-pyrimidinamin, N-(3-bensoylamidofenyl)-4-(3-pyridyl)-2-pyrimidinamin, N-[3-(2-pyridyl)karboxamidofenyl]-4-(3-pyridyl)-2-pyri-5 midinamin, N-[3-(3-pyridyl)karboxamidofenyl]-4-(3-pyridyl)-2-pyri-midinamin, N-[3-(4-pyridy1)karboxamidofenyl]-4-(3-pyridy1)-2-pyrimidinamin,
10 N-(3-pentafluorbensoylamidofenyl)-4-(3-pyridyl)-2-pyri midinamin, N-[3-(2-karboxibensoylamido)-fenyl]-4-(3-pyridyl)-2-pyrimidinamin, N-(3-n-hexanoylamidofeny1)-4-(3-pyridy1)-2-pyrimidinamin, 15 N-(3-nitrofenyl)-4-(2-pyridyl)-2-pyrimidinamin, N-(3-nitrofenyl)-4-(4-pyridyl)-2-pyrimidinamin, N-[3-(2-metoxibensoylamido)-fenyl]-4-(3-pyridyl)-2-pyrimidinamin, N-[3-(4-fluorbensoylamido)-fenyl]-4-(3-pyridyl)-2-pyri- . . 20 midinamin, • · · ; N-[3-(4-cyanobensoylamido)-fenyl]-4-(3-pyridyl)-2-pyri- • * t ·* · midinamin, ··*· N-[3- (2-tienylkarboxamido) -fenyl]-4-(3-pyridyl) -2-pyri- "· midinamin, • V 25 N-(3-cyklohexylkarboxamidofenyl)-4-(3-pyridyl)-2-pyri- ! : : midinamin, N-[3-(4-metylbensoylamido)-fenyl]-4-(3-pyridyl)-2-pyri- : midinamin, • * ,·*·, N- [3 - (4-klorbensoylamido) -fenyl] -4- (4-pyridyl) -2-pyri- 30 midinamin, • · * * t '· '·* N-{3- [4- (4-metylpiperazinometyl) -bensoylamido] -fenyl}-4- < i · ·...· (3-pyridyl) -2-pyrimidinamin, N-(5-bensoylamido-2-metylfenyl) -4-(3-pyridyl) -2-pyri- ,···. midinamin, * ·
35 N-[5-(4-metylbensoylamido)-2-metylfenyl]-4-(3-pyridyl)-2-pyrimidinamin, 59 105534 N-[5-(2-naftoylamido)-2-metylfenyl]-4-(3-pyridyl)-2-pyrimidinamin, N-[5-(4-klorbensoylamido)-2-metylfenyl]-4-(3-pyridyl)-2-pyrimidinamin,
5 N-[5-(2-metoxibensoylamido)-2-metylfenyl]-4-(3-pyridyl)-2-pyrimidinamin, N-(3-trifluormetoxifenyl)-4-(3-pyridyl)-2-pyrimidinamin, N-(3-[l,l,2,2-tetrafluoretoxi]-fenyl)-4-(3-pyridyl)-2-pyrimidinamin,
10 N-(3-nitro-5-metylfenyl)-4-(3-pyridyl)-2-pyrimidinamin, N-(3-nitro-5-trifluormetylfenyl)-4-(3-pyridyl)-2-pyrimidinamin, N-(3-nitrofenyl)-4-(N-oxido-3-pyridyl)-2-pyrimidinamin eller
15 N-(3-bensoylamido-5-metylfenyl)-4-(N-oxido-3-pyridyl)-2-pyrimidinamin eller ett farmaceutiskt användbart sait av en sadan här fö-rening, som innehäller en saltbildande grupp. • t. 20 7. Förfarande enligt patentkravet 1, kannetecknat därav, * · · .* I att utgängsämnen väljs sä, att man erhäller * · ♦ "·/ N-{5-[4-(4-roetylpiperazinometyl)-bensoylamido]-2-mety1- • · · fenyl}-4-(3-pyridyl)-2-pyrimidinamin eller ett farma-’ * ceutiskt användbart sait av denna förening. r·:* 25 I I »
8. Förfarande enligt patentkravet 1 för framställning av N-{5-[4-(4-metylpiperaz inomety1)-bensoylamido]-2-mety1-fenyl}-4-(3-pyridyl)-2-pyrimidinamin eller ett farma- t · '·, ceutiskt användbart sait därav, kännetecknat därav, att I f ·
30 N-(5-amino-2-metylfenyl)-4-(3-pyridyl)-2-pyrimidinamin » a • ’! omsätts med 4-(4-metylpiperazinomety1)bensoylklorid och, < * · om sä önskas, den erhällna föreningen omvandlas tili ett a farmaceutiskt användbart sait. • » * i · lit • ‘ t It·
FI931458A 1992-04-03 1993-03-31 Förfarande för framställning av farmakologiskt aktiva pyrimidinderivat FI109534B (sv)

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