FI85373B - Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara pyridazinaminderivat. - Google Patents

Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara pyridazinaminderivat. Download PDF

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FI85373B
FI85373B FI851177A FI851177A FI85373B FI 85373 B FI85373 B FI 85373B FI 851177 A FI851177 A FI 851177A FI 851177 A FI851177 A FI 851177A FI 85373 B FI85373 B FI 85373B
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formula
parts
aryl
lower alkyl
hydrogen
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FI851177A
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FI85373C (sv
FI851177A0 (fi
FI851177L (fi
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Raymond Antoine Stokbroekx
Der Aa Marcel Jozef Maria Van
Joannes Josephus Maria Willems
Marcel Gerebernus Maria Luyckx
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Janssen Pharmaceutica Nv
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    • 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
    • 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
    • A61P31/12—Antivirals
    • 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
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
    • C07D237/22—Nitrogen and oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
    • C07D237/24—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
    • 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
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Virology (AREA)
  • Communicable Diseases (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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicinal Preparation (AREA)

Claims (8)

1. Analogiförfarande för framställning av terapeu-tiskt användbara pyridazinaminderivat med formeln I 5 N—N R1—(I) R2 R3 10 och/eller farmaceutiskt godtagbara syraadditionssalter och/eller möjliga stereokemiskt isomera former och/eller möjliga tautomera former därav, i vilken formeln
15 R1 är väte, halogen, lH-imidazol-l-yl, lägre aryl- oxi, aryloxi, aryllägre alkyloxi, lägre alkyltio, aryltio, hydroxi, merkapto, amino, lägre alkylsulfinyl, lägre alk-ylsulfonyl, cyano, lägre alkyloxikarbonyl, lägre alkyl-karbonyl eller lägre alkyl;
20 R2 och R3 är oberoende av varandra väte eller lägre alkyl, eller R2 och R3 tillsammans kan bilda en bivalent radikal med formeln -CH=CH-CH=CH-; A är en bivalent radikal med formeln
25 -CH=N-CH=CH- (a), R4 -C.H2l.-N-CnH2n- (b),
30 R5 R6 -C„H2lll-C-CnH2n- (c) eller R7 R® -CWW^-C =C-CnH2n- (d), 74 8 5373 väri nägon av väteatomerna i gruppen CmH2m, Cm.1H2(B.1) eller CnH2n kan vara ersatt av lägre alkyl eller aryl; m och n är oberoende av varandra heltal 1-4, var-vid summan av m och n är 3, 4 eller 5;
2. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att A är en bivalent radikal med 30 formeln b, väri R4 är aryl, pyridinyl, pyrimidinyl, lägre alkoxikarbonyl, aryllägre alkyl, diaryllägre alkyl eller kinolinyl; eller A är en bivalent radikal med formeln c, väri R5 är väte, aryl, arylamino, (aryl)(lägre alkyl)amino, hydroxi eller indolyl och R6 är väte, aryl, arylkarbonyl 35 eller (arylkarbonyl)lägre alkyl; eller A är en bivalent radikal med formeln d. 77 ö 5 3 7 3
3. Förfarande enligt patentkravet 2, känne-t e c k n a t därav, att R2 och R3 vardera är väte.
4. Förfarande enligt patentkravet 3, känne-t e c k n a t därav, att i den bivalenta radikalen A med 5 formeln b är m heltalet 2 eller 3 och n är 2; i radikalen A med formeln c är m heltalet 1 eller 2 och n är heltalet 2; och i radikalen A med formeln d är m heltalet 1 eller 2 och n är heltalet 2.
5. Förfarande enligt patentkravet 4, känne- 10 tecknat därav, att R1 är halogen, lägre alkoxi, aryloxi, lägre alkyltio, aryltio eller cyan.
5 R4 är aryl; tiazolyl; pyrimidinyl; kinolinyl; lägre alkylkarbonyl; lägre alkyloxikarbonyl; aryllägre alkyl; diaryllägre alkyl; fenyl som substituerats med arylkarbo-nyl; pyridinyl som eventuellt substituerats med cyan eller lägre alkyl; cyklohexyl eller cyklohexenyl, vilka vardera 10 eventuellt substituerats med upp tili tvä substituenter, vilka självständigt är cyan eller aryl; R5 är väte; lägre alkyl; aryl; hydroxi; lägre alkyl-oxi; aryloxi; lägre alkyloxi som substituerats med morfo-lin, pyrrolidin eller piperidin; amino; (lägre alkyloxi-15 karbonyl)amino; arylamino; (aryl) (lägre alkyl)amino; (aryllägre alkyl)amino; (aryllägre alkenyl)amino; (aryllägre alkenyl)(lägre alkyl)amino; eller arylkarbonyloxi; R6 är väte; aryl; lägre alkyl; (lägre alkylkarbonyl-amino)lägre alkyl; aryllägre alkyl; arylkarbonyllägre alk-20 yl; aminokarbonyl; arylkarbonyl; arylaminokarbonyl; (aryl lägre alkyl)karbonyl; lägre alkyloxikarbonyl; indolyl; eller pyridinyl; R7 och R8 är oberoende av varandra väte; lägre alkyl; aryl; aryllägre alkyl; eller pyridinyl; 25 varvid aryl är fenyl som, eventuellt substituerats med upp tili 3 substituenter, vilka självständigt är halogen, lägre alkyl, trifluormetyl, nitro, amino, lägre alkyloxi, hydroxi eller lägre alkyloxikarbonyl; tienyl; eller naftalenyl; med villkor att 30 i) dä A är en radikal med formeln c och R6 är väte, mäste R5 vara annat än väte, hydroxi eller lägre alkyl; ii) dä R2 och R3 är väte och A är en radikal med formeln b, mäste R4 vara annat än 3,3-difenylpropyl; iii) dä R2 och R3 är väte och A är en radikal med 35 formeln a, mäste R1 vara annat än halogen; l: 75 85373 iv) dä R1 är klor, R2 och R3 är väte och A är en radikal med formeln b, mäste R4 vara annat än 2-metoxife-nyl; v) dä R1 är klor och A är en bivalent radikal med 5 formeln b, mäste R4 vara annat än (dimetoxifenyl)metyl, (dimetoxifenyl)etyl, a-metylfenetyl eller (2-metylfenyl)-metyl; vi) d£ R1 är metoxi och A är en bivalent radikal med formeln b, mäste R4 vara annat än (dimetoxifenyl)etyl eller 10 (dimetoxifenyl)metyl; kännetecknat därav, att man a) alkylerar en amin med formeln II πίΓΛ (II) 15 med ett pyridazin med formeln III N-N 20 r1 %—w ,)=\ , (HD R RJ väri W betecknar en reaktiv, avgäende grupp, ifall önsk-25 värt, i ett reaktionsinert lösningsmedel, eventuellt i närvaro av en bas; b) alkylerar en pyridazinamin med formeln I-a N—N c Ri—/ V f m 2n^
30. V / N NH <I-a) R r3 med en reaktant med formeln IV 35 W-R4 (IV) 76 ö 5 6 Ί 6 ifali önskvärt, i ett reaktionsinert lösningsmedel, even-tuellt i närvaro av en bas, varvid erhälls en förening med formeln I-b 5 , /N_N^ H, 2 x \ 3 n 2n^ R rj 10 eller c) reduktivt N-alkylerar en pyridazinamin med formeln I-a med en karbony1förening med formeln 15 (1^-^)=0=0 väri föreningen (1^-^)=0=0 är en förening med formeln R4"b-H, väri en -CH2- radikal oxideras tili en karbonyl-grupp, och väri R4"b är aryllägre alkyl, diaryllägre alkyl, 20 cyklohexyl eller cyklohexenyl, i ett reaktionsinert lös ningsmedel, varvid erhälls en förening med formeln I-b; och ifall önskvärt, omvandlar de sälunda erhällna föreningarna med formeln I i terapeutiskt aktiv, giftfri syraadditionssaltform genom behandling med en lämplig sy-25 ra, eller omvänt, omvandlar syraadditionssaltet i den fria basformen med alkali; och/eller framställer stereokemiskt isomera former därav.
6. Förfarande enligt patentkravet 4, känne-tecknat därav, att R1 är halogen.
7. Förfarande enligt patentkravet 1, känne- 15 tecknat därav, att föreningen med formeln I är 3-brom-6-[4—(3-metylfenyl)-l-piperazinyl]pyridazin eller ett farmaceutiskt godtagbart syraadditionssalt därav.
8. Förfarande enligt patentkravet 1, känne-tecknat därav, att föreningen med formeln I är 20 3-klor-6-[3,6-dihydro-4-(3-metylfenyl)-1 ( 2H)-pyridinyl]py- ridazin eller ett farmaceutiskt godtagbart syradditions-salt därav.
FI851177A 1984-03-26 1985-03-25 Analogiförfarande för framställning av terapeutiskt användbara pyridaz inaminderivat FI85373C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US59344484A 1984-03-26 1984-03-26
US59344484 1984-03-26
US06/702,772 US5001125A (en) 1984-03-26 1985-02-15 Anti-virally active pyridazinamines
US70277285 1985-02-15

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FI851177A0 FI851177A0 (fi) 1985-03-25
FI851177L FI851177L (fi) 1985-09-27
FI85373B true FI85373B (fi) 1991-12-31
FI85373C FI85373C (sv) 1992-04-10

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FI851177A FI85373C (sv) 1984-03-26 1985-03-25 Analogiförfarande för framställning av terapeutiskt användbara pyridaz inaminderivat

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US (3) US5001125A (sv)
EP (1) EP0156433B1 (sv)
KR (1) KR870001158B1 (sv)
AT (1) ATE61050T1 (sv)
AU (1) AU576563B2 (sv)
BG (1) BG43690A3 (sv)
CA (1) CA1238321A (sv)
CZ (1) CZ277730B6 (sv)
DE (1) DE3581819D1 (sv)
DK (1) DK166277C (sv)
ES (1) ES8606289A1 (sv)
FI (1) FI85373C (sv)
GR (1) GR850714B (sv)
HU (1) HU198010B (sv)
IL (1) IL74707A (sv)
NO (1) NO161257C (sv)
NZ (1) NZ211494A (sv)
PH (1) PH22495A (sv)
PT (1) PT80157B (sv)
RO (1) RO91197B (sv)
SU (1) SU1384198A3 (sv)
ZW (1) ZW5485A1 (sv)

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EP0156433B1 (en) 1991-02-27
ATE61050T1 (de) 1991-03-15
FI85373C (sv) 1992-04-10
HUT37614A (en) 1986-01-23
CZ277730B6 (en) 1993-04-14
SU1384198A3 (ru) 1988-03-23
DK166277C (da) 1993-08-30
CA1238321A (en) 1988-06-21
US5292738A (en) 1994-03-08
FI851177A0 (fi) 1985-03-25
DK134185D0 (da) 1985-03-25
EP0156433A2 (en) 1985-10-02
ES8606289A1 (es) 1986-04-16
EP0156433A3 (en) 1986-07-23
DE3581819D1 (de) 1991-04-04
PH22495A (en) 1988-09-12
PT80157B (en) 1987-03-20
US5001125A (en) 1991-03-19
GR850714B (sv) 1985-06-14
NO161257C (no) 1989-07-26
AU576563B2 (en) 1988-09-01
FI851177L (fi) 1985-09-27
KR850006401A (ko) 1985-10-05
NO851167L (no) 1985-09-27
US5157035A (en) 1992-10-20
ZW5485A1 (en) 1986-10-22
IL74707A0 (en) 1985-06-30
DK166277B (da) 1993-03-29
BG43690A3 (en) 1988-07-15
PT80157A (en) 1985-04-01
DK134185A (da) 1985-09-27
KR870001158B1 (ko) 1987-06-13
RO91197B (ro) 1987-07-01
ES541521A0 (es) 1986-04-16
IL74707A (en) 1988-05-31
NO161257B (no) 1989-04-17
AU4034885A (en) 1985-10-03
CS195285A3 (en) 1992-11-18
HU198010B (en) 1989-07-28
NZ211494A (en) 1988-05-30
RO91197A (ro) 1987-06-30

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