FI120646B - Kinazolinderivat - Google Patents
Kinazolinderivat Download PDFInfo
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- FI120646B FI120646B FI973832A FI973832A FI120646B FI 120646 B FI120646 B FI 120646B FI 973832 A FI973832 A FI 973832A FI 973832 A FI973832 A FI 973832A FI 120646 B FI120646 B FI 120646B
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- alkyl
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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
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Chemical & Material Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (19)
1. Förening med formein ( R ^ ) n R2 / (R1 > 5 ^ och farmäpeutiskt godtagbara salter därav, där m är 1, 2 eller 3; varje R1 väljs självständigt ur en grupp, sora ut-10 gors av väte, halogen, hydroxi, amino, hydroxiamino, kar- | boxi, Ci-4-alkoxikarbonyl, nitro, guanidino, ureido, karba- j moyl, cyan, trifluormetyl, (R6) jN-karbonyl ooh fenyl-W- | alkyl, där W väljs ur en grupp, som utgörs ay en enkelbind- j ning, O, S och NH; 15 eller varje R1 väljs självständigt ur en grupp, som utgörs av cyan-Ci-4-alkyl ooh R9, där R9 väljs ur en grupp, som be star av R5, RsO, (Rfj 2N, R'C (=0) , RfiONH, A och R5Y; där R5 är Gi-i-alkyl; Rb är väte eller R5, där R5 är lika eller oli ka; R7 är R5, R50 eller (R6)2N; A väljs ur en grupp, som j i 20 utgörs av piperidino, morfolino, pyrrolidino och 4-R5- j piperazIn-1-yl, imidasol-I-yl, 4-pyridon*-l-yl, ikarbdxi-C.1,4-* I alkyl, fenoxi, fenyl, fenylsuifany], C3-4-alkenyl, (R6)2-N- J karbQnyl-Ci-4-alkyl; och Y väljs ur en grupp, som utgörs av j S, SO, SOsi alkylgrupperna i (R6}2H Sr eventuellt substitue- j 25 rade; med halogen eller Ra, där R9 Sr definierad sasom ovan, I och alkylgrupperna i R5 oeh RsO är eventuellt subst-ituerade I med halogen, R60 eller R9, där R9 och R6 är definierade sä- ] som ovan, och där de resulterande grupperna är eventuellt j substituerade med halogen eller R9, förutsatt att kväve-, j 30 syre- eller svavelatomen och en annan heteroatom ej kan I \ vara bundna till saroma kolatom, och förutsatt att, högst tre "R9"“-enheter kan gmfatta R'1'; eller varje R1 väljs självständigt ur en grupp, som utgörs av R5-sulfonylamino, ffealimido-Ci-i-alkylsulfonylami-5 no, bensamido, bensensulfonylamino, 3-fenylureido, 2-oxo-pyrrolid.in-1-yl, 2,S-dloxopyrrolidin-l-yl och RX0-C2-,i-alka- noylamlno, där R10 väljs ur en grupp, som utgörs av halogen, R°0, C2-4-alkanoyloxi, R7C (=0) och (R6) 2N; och där i namnda bensamido- eller bensensulfonylamino- eller fenyl- eller 10 fenoxi- eller anilino- eller fenylsulfanylsubstituenten R1 kan eventuellt vara en eller tva halogener, C] ..4-alkyl-, cyan-, metansulfonyl- eller Cj^-alkoxisubstituenter; eller vilka som heist tvä R1 fgrenade med koiet, till vilket de är bundna, omfattar en en 5 - 8- ledad IS ring, som omfattar minst en eller tvä heteroatomer, som \ väljs bland syre, svavel eller kväve; och där alkylgrup- { perna och alkyldelarna i alkoxi- eller alkylaminogrupperna | kan vara rakkedjade eller, da de bestar av minst tre kola-tome f, förgrenade eller cykliska;
20 R2 väljs bland väte eller Ci-g-alkyl; n är 1 eller 2 och varje R3 väljs självständigt | bland väte, Ci_6-a.lkyl, amino, halogen och hydroxi; R4 är azido eller Rn-etynyl, där R11 väljs bland väte, eventuellt substituerad CT-g—alkyl, där substituenterna 25 är valda bland väte, amino, hydroxi, R50, R5NH och (R3) ;>N.
2. Förening enligt patentkrav 1, där R2 är väte och R4 är R11-etynyl, där R11 väljs bland väte, eventuellt substituerad Ci-6-alkyl, där substituenterna är valda bland väte, amino, hydroxi, R50, R5KH och (R5} ->N. 30 :3. Förening enligt patentkrav 2, där m ar 1 eller 2, varje R1 väljs självständigt bland väte, hydroxi, amino, hydroxiamino, karboxi, nitro, karbamoyl, ureido, R5, som eventuellt är substituerad med halogen, R°0, HOC(=0), (R6)2NC{=0), A och R6)2N;
35 R50 eventuellt substituerad med halogen, ReO, C2-4- I alkanoyloxi, HOC(=Q), (R*j 2$,. &, fenyl; ] R5NH, (R5)2N, R-'MH2f (R")2NH, R5NHC (=0} , (R5)2NC<=0), R’S, fenyl-C2_4-alkoxi, R120, dar P.'?; Sr HK och K Sr C2-4-alkyl, eventuellt substituerad med halogen, R60, C2-4'-alkanoyloxi/ HOC(-=0) , 1 ja (R6) 2'£?r R6OKO, R6OENH, CN och fenyl; R5NH even-5 tuellt substituerad med halogen, C2_:i-alkanoyloxi, RB0, R7C(=0), {Rs)2N, A, R60K0, R60KNH, C5H5Y, CN; (Rb) 2N€=0) , Rs0NH, RsS, Ch-4-alkylsulf onylamino, fta-limido-Ci-4-alkylsulf onylamino, 3-fenylureido, 2-oxopyrroli-din-l-yl, 2,S-dioxopyrrolidin-l-yl, halogen-C2-4~alkanQyl“ 10 amino, hydroxi-^b-t-alkanoylamino, C2_4-alkanoyloxi~C2-4-alka- ndylamino, Ci-4-alkoxi-C2-a-alkanoylamino, karboxi-C2-4~alka-noylamino, Ci-4-alkoxikarbonyl-C2-4”alkanoylamino, karbamoyl-Cs-^-alkanoylamino, NHC^-alkyikarbamoyi-Ci^-alkanoylamino, N, N“di-lCi_4-alkyI] karbamoyl“C2-4“arkanoylamino, amino-C2-4- j 15 alkanpylainino, Ci^j-alkylaminQ-Ca-i-älkanoylamino, di-C;_,s- j alkylamino-C2~4_alkanoyiamino, och där i nämnda fenyl eller | fenoksi eller anilinosubstituenten R1 kan eventuellt vara j en eller tv a halogen-, Cj.-4-alkyl- eller Ci-q-alkoxi- j substituenter; eller vilka som heist tva R1 förenade med J 20 kolen, till vilka de Sr bundna, bildax en 5 - 8-iedad ring, I som: omfattar minst en eller tvä heteroatomer, som välj s \ bland syre, svavel och kväve; och dax alkylgrupperna och | alkyldelafna i. alkoxi- eller alkylaminogrupperna kan vara | oförgrenade eller, da de bestar av minst tre koi, förgrena- \ 25 de eller cykliska; j varje R3 väljs sjäivstandigt bland väte, metyl, j etyl, amino, halogen och hydroxi; | R4 Sr RI1-etynyl, där Ru äx väte, j
4. Förening enligt patehtkrav 3, där varje R1 väljs j 30 sjSlvstadigt bland väte, hydroxi, amino, hydroxiamino, ni- J tro, karbamoyl, uxeido, R5, som: eventuellt är substituerad \ med halogen, R60, HOC;(=Q) , (R6)2NC(=0) ; j R50 eventuellt substituerad med halogen, R°0, C2-4- j alkanoyloxi, HOC (=0) , (R6) 2N, A, fenyyii; j
35 R5NH, (R5)2N, R5NH2, (R5)2NH, R5NHC(=0), (R5)2NC(=0) , j RsS, fenyyli-C2-.j-alkoxi, och där i nämnda fenyl substituent j R1 ka n eventuelit vara en eller tvä halogen-, Rs- eller R50-subStituerrter;. eller vilka sora heist tvä R1 förenade med koien, tili vilka de är bundna, bildar en 5 - 8—ledad ring, som omfat car minät; en eller tvä heteroatomer, som väljs 5 bland syre, svavei eller kväve; ooh dar alkylgrupperna och alkyldelarna i alkoxi- eller alkylaminogrupperna ka n vara oförgrenade eller, da de bestär av minst tre koi, förgrena-de eller cykliska.
5. Förening enligt patent kr av 1, där R'· är väte ooh
10 R* är azido.
6. Förening enligt patentkrav 5, där m är 1 eller 2, varje R1 väljs självständigt bland väte, hydroxi, amino, hydroxiamino, karboxi, nitro, karbamoyl, ureido, R5, som eventuelit är substituerad med halogen, RbO, ROC(=0), 15 (R6)2NC{=Ö), Λ och (R6)2N; R120, där R12 är HK: och K är Ga-g-alkyl, eventuelit substituerad med halogen, R£0, C?_4~al kanoyloxl, HOC (=0) , A och (R6)2N, R6DK0, R60KNH, CN och fenyl; R5NH eventuelit sub- [ stituerad med halogen, C2-4-alkanoyloxi, R60, R'C(-0), j 20 (R6)2N, A, Rs0K0,: R60KNH, :C6H:5Y, CN; ] (R6) 2KC=0) , R50NH, R"S, Ci _ 4 - a 1 ky 1 s a 1föny1amino, fta- | limido-Ci-i-alkylsulfonylamino, 3-fenylureido, 2-oxöpyrröli- j din-l-yl, :2, S-dloxopyrrolidln-l-yl, halogen-Cs-e-alkanoyl- I amino, hydroxi-C2-4:-alkanoylamino, Cs-a-al kanoyloxi-C2-4~alka- :j 25 noylamino, :Cr-4-aikpxi“C2-4“-al:kanoylamino·, karboxi-C2-4-alka- j noylamino, Ci-4-älkoxikarbonyl-C2-4-alkanoylamino, karbamoyl- 1 Ca-i-alkanoylamino, N-Ci-4-alkyl karbamoyl-Cs-d-alkanoylaminQ, j N, N-d.i- [Ci-4-alkyl] karbamoyl-Cs-i-alkanoylamino, amino-Ca.-4~ 1 alkanoylamino, Gi-4-alkylaminö-C2-4-alkanöyIamihö/: öi-Ci-4- j 30 alkylamino-Cs-ii-alkanoylamino, och där i nämnda fenyl- eller | fenoxi- eller anilinosubstituent R1 kan eventuelit vara en j eller tvä halogen-, Ci-4-alkyl- eller Ct-4-alkoxi subs- 1 titu.ent.er; eller vilka som heist tvä R1 förenade med kolen, | tili vilka de är bundna, bildar en 5 - 8— ledad ring, som ] 35 omfattar minst en eller tvä heteroatomer, som väljs bland 1 syre, svavei eller kväve; och där alkylgrupperna och alkyl- j delafha i alkoxi- och alkylaminogrupperna kan vara oförgre-nade eller, dä de bestar av minst tre koi, förgrenade eller cykliska; och varje R3 väljs s jälvständigt bland väte, xnetyl, 5 etyl, amino, halogen och hydroxi,
7. Förening enligt patentkrav 6, där varje R1 väljs självstädigt bland väte, hydroxi, amino, hydroxiamino, nitro, karbamoyl, ureido, R5, som eventuellt är substituerad med halogen, RsO, H0C(=0), Η2Ν€ (=0};
10 R5ö eventuellt substituerad med halogen, R60, C2-4- alkanoyloxi, HOC (=0) , (R6) 2N, A, fenyl; R5NH, (E5).!*!, R5NH2, (Rs}2MH, R5NHC(=0), (R5)2NC (=0:) , I R5S, fenyl-C2-4-alkoxi, och där 1 nämnda fenylsubstituent R1 \ kan eventuellt vara en eller tvä halogen-, R5- tai R50-15 substitneuter; eller vilka som heist tvä R1 förenade med kolen, till vilka de är bundna, bildar en 5 - 8~iedad ring, som omfattar minst en eller tvä heteroatomer, som väljs bland syre, svavel eller kväve; och där alkylgrupperna och alkyldelarna i alkoxi- eller alkylaminogrupperna kan vara 20 oforgrenade eller, dä de bestar av minst tre koi, förgrena- j de eller cykliska. | 8,,: Förening enligt patentkrav 7, där R är halogen | och R1 är väre eller R50. ]
9. Förening enligt patentkrav 8, där R5 är metyl. I 25 10, Förening enligt patentkrav 1, som väljs ur en j grupp, som bestar av foljande | (6,7~:(dipropQxikxnazolin~4-yl) - (3-etynylfenyljsrnin; I J (6,7-(dietoxikinazolin-4-yl}-(3-etynyl-5-fluor- | fenyl)amin; 1 30 (6.., 7- (dleto^ikinazolin-4-yl} - (3~etynyl-4-fluor- j fenyl·}amin; 1 j (6, 7- (dietox;ikinazdlin-4-yl) - (5-etynyl-2-metyl- j fenyl)amin; j (6,7-(dietoxikinazolin-4-yl)- (3-etynyl~4-metyl- j 35 fenyl)amin; j \ j (6-:am;inQmetyi~7-inetoxikinazo'lin^4“yi.·) ~ (3-eLyny.l-fsnyl) amiή; (6-ami:nometyl-7-metoxikina2olin-4:-yl} - (3-etynyl-f enyl)amin; 5 { 6-:aminokarfoonylmetyl-7-ineto.xikinazolin-4-yl) - (3- etynylfenyl}amin; {6-aminokarbonyletyl-7-metoxikina2olin-4-yl)- (3-e tynyl£enyl}ami n; (6-aminokarbönylmetyl-7-etöx:ikinazoli;n-4~yl) - (ΒΙΟ etynylfenyl)amin; (6-aminokarbonyletyl-7~etGxikinazQlin-4-yl)- (3-etynylfenyl)amin; (6-aminokarbonylmetyl-7-isopropoxikinazolin-4-yl)-(3-etynyIfenyl)amin; 15 (6-aminGkarbonyimetyl-7-propoxikinazoliri“4-yi) - (3- etynylfenyl)amin; (6~a:minokarbonylmetyl-7-metoxikinazolin-4 -yl) - :(,3- | etynylfenyl)amin; \ (6- amino kanbo ny1e t y1-7 -i sopropoxi kin a z olin-4-y 1) - { 20 (3“et:ynyl£enyl):amin; och ! {6-aminö:karbQnyletyl-7-propoxikinäzGlin-4-yl) - (3·« :j :j etynylfenyl)amin. |
11, Forening enligt. patentkrav 1, k ä n n e t e c k - | n a cl av att den Sr ( 6, 7-bis (2-metoxietpxi) kinazolin-4-yl] - j 25 3^etynylfenyl)-amin-hydroklorid. ] 12. .Förfarande för framstälining av en förening | rned f o me In | R2 / 1 R4 I 30 där I m är ij 2 eiler 3; f i ] varje, R1 väljs självständigt ur en grupp, som ut-gors av väte, halogen, hydroxi, amino, hydroxiamino, kar~ boxi, Ci_4-alkoxikarbonyl, nitro, guanidino, are i do, karba-moyl, cyan, trifluormetyl, (R6) aN-karbonyi och fenyi-W-5 alkyl, där W väljs ur en grupp, som utgors av en enkelbind-ning, 0, S och NM; eller varje R1 väljs självständigt ur en grupp, som utgors av cyan-Ci-4-alkyl och R9, där R9 väljs ur en grupp, sora bestär av K5, R50, {R6}^, R7C(-Q), R50NK, A och R5Y; där
10 R5 är C1-4-alkyl; Re är väte eller R', där R3 är lika eller oli ka; R7 är R5, Rs0 eller (Rb)2N; A väljs ur en grupp, som utgörs av piperidino, morfoiino, pyrrolidino och 4-Rb-piperazin-l-yl, imidazol-l-yl, 4-pyridon-l-yl, karboxi-Ci-4” alkyl, fenoxi, fenyl, fenylsulfanyl, C2-a-alkenyl, (Rbj2-N-15 harbonyl-Ci^-aikyl; och Y väljs ur en grupp, som utgörs av Sf SO, S0:3; alkylgrupperna i (R6:)2.N är eventuelit substitue-rade med halogen eller R9, där R9 är definierad säsom ©van, och alkylgrupperna i R' och R50 är eventuelit substi tuerade med halogen, Rfi0 eller R9, där R9 och Rb är definierade sä-20 som ovarj, och där de resulterande gruppernä är substituera- f de med halogen eller R9, förutsatt att kväve-, syre- eller ] svavelatomen och en annan heteroatom ej kan vara bundna j tili gamma kolatom, och förutsatt att, högst tre "R9"- | enheter kan omfatta R1; . I 25 eller varje R1 väljs självständigt ur en grupp, som I utgörs av R^-sulfonylamino, ftalimido-Ci-4-alkylsulfonylami- \ no, bensamido, b e n s en s u1f ony1ami no, 3-fenylureido, 2-oxo- | pyrrolidin-l-yi, 2, 5-dioxopyrrolidin—1—yl och R1Q-C2_4-alka- | noylamino, där R10 väljs ur en grupp, som utgörs av halogen, 1
30 R°Ö, C2-4“Silkanoylöxi, R70(=0} och (Re}2N; och där i näranda j bensamido- eller bensensulfonylami.no- eller fenyl- eller j fenoxi- eller anilino- eller fenylsulfanylsubstituenten R1 j \ kan eventuelit vara en eller tvä halogener, Ci-4-alkyl-, cy- S an-, metansulfonyl- eller C1.. λ - a 1 kox .i s ubs t i t ue n t e r ; 35 eller vilka som heist tvä R1 förenade med kolet, tili vilket de är bundna, omfattar en en 5-8- ledad 1 ring, som omiattar mxnst en eller evä beteroatomer, sen väljs bland syre, svavel eller kväve; ooh, där alkylgrup-perna deb alkyldelarna i alkoxi- eller alkylaminogruppefna kan vara rakkedjade eller, dä de bestär av irtinst tre kola-5 t outer, för grenade eller cykliska; R2 väljs bland väte eller Gi-g-alkyl; n är 1 eller 2 och varje R3 väljs självständigt bland väte, Ci-6-alkyl, amino, halögen och hydroxi; R'3 är azido eller R11-etynyl, där R11 väljs bland vä-1Θ te, eventuellt substituerad Ct-6-alkyl, där substituenterna är valda bland väte, amino, hydroxi, R5Ö, och {]Ra) 2N, vilket förfarande omfattar steg, där a) en förening med formeIn OH 0 j j i 15 där R1 ooh m är sä söm -ovan definieras, behandlas | med CClή, och eventuellt med en substituerad trlarylfösfin, \ som eventuellt föreligger pä en inert bärarpoiymer och som \ bar formeIn Ar-jP, där varje Ar är en eventuellt substitue- I rad Cg-io-ärylgrupp Ooh var och en av substituenterna Sr ] 2Ö sjäivständigt valda bland Ci-g-alkyl; och 1 :jj b) produkten enligt punkt ä) behandlas med en. fore- ij ning med formeIn j * /m* I hn—/f sys I j I $ $ 2.5 där R2, R3 och n är som ovan definieras, och J är Y j eller R4, där R4 är som ovan definieras, förutsatt aft, dä :J j är Y, sa mäste produkten enligt punkt b) behandlas ytterli-gare med en alkyn.
13. Förfarande. enligt patentkrav 12, där var j e fe-nylgrupp väljs bland fenyl, naft-l-yl Ooh naft-2-yl. 5 14. Förfarande enligt patentkrav 13, där varje few nylgrupp är självständigt substi tuerad med en frän noll tili ett maximum an tai Cx-s-alkylgrupper.
15. Förfarande enligt patentkrav 13, där varje Är är fenyl. 10 16. Förfarande enligt patenfekrav 12, där nämnda triafylfostin föreligger pä en inert bärarpolymer.
17. Förfarande enligt patentkrav 16, där nämnda po- ; lymer är en divinylbensen-tvärbunden polymer av styren.
18. Farmaceutisfc komposition för behandlir.g av hy-15 perproliferativa sjukdomar i däggdjur, vilken komposition omfattar en terapeutiskt effektlv mängd av en förening en- ^ li.gt patentkrav 1 ooh en farmaceutiskt godtagbar bärare. | :ί | $ j
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US41330095A | 1995-03-30 | 1995-03-30 | |
US41330095 | 1995-03-30 | ||
IB9500436 | 1995-06-06 | ||
PCT/IB1995/000436 WO1996030347A1 (en) | 1995-03-30 | 1995-06-06 | Quinazoline derivatives |
Publications (3)
Publication Number | Publication Date |
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FI973832A FI973832A (sv) | 1997-09-29 |
FI973832A0 FI973832A0 (sv) | 1997-09-29 |
FI120646B true FI120646B (sv) | 2010-01-15 |
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ID=23636708
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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FI973832A FI120646B (sv) | 1995-03-30 | 1997-09-29 | Kinazolinderivat |
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Families Citing this family (515)
Publication number | Priority date | Publication date | Assignee | Title |
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US6811779B2 (en) | 1994-02-10 | 2004-11-02 | Imclone Systems Incorporated | Methods for reducing tumor growth with VEGF receptor antibody combined with radiation and chemotherapy |
TW321649B (sv) * | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
GB9424233D0 (en) * | 1994-11-30 | 1995-01-18 | Zeneca Ltd | Quinazoline derivatives |
GB9508535D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivative |
DE69613367T2 (de) * | 1995-04-27 | 2002-04-18 | Astrazeneca Ab | Chinazolin derivate |
GB9508537D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
GB9508565D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
GB9508538D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
GB9624482D0 (en) * | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
GB9603095D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
GB9603097D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline compounds |
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