LV10100B - Inhibitors of purine nucleoside phosphorylase - Google Patents
Inhibitors of purine nucleoside phosphorylase Download PDFInfo
- Publication number
- LV10100B LV10100B LVP-93-342A LV930342A LV10100B LV 10100 B LV10100 B LV 10100B LV 930342 A LV930342 A LV 930342A LV 10100 B LV10100 B LV 10100B
- Authority
- LV
- Latvia
- Prior art keywords
- compound
- cyclo
- ethyl
- substituted
- amino
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (16)
- LV 10100 Patentformulas punkti 1. Savienojums 2-amino-7-(R)-3H,5H-pirolo[3,2-d]pirimidīn-4-ons, kurā R ir cikloheksenilgrupa, cikloheksilgrupa vai grupa -CH^-R* (kur R* ir neobligāti nenoteikti aizvietota alicikliska, he-teroalicikliska grupa vai piridinilgrupai). 1 1
- 2. Savienojums pēc punkta 1, kurā R ir grupa -CH^-R un R ir nenoteikti aizvietota 2-, 3- vai 4-piperidinilgrupa, 2- vai 3-tetra-hidrofuranilgrupa, 2- vai 3-tetrahidrotienilgrupa, 2- vai 3-pirolidi-nilgrupa, 2-, 3- vai 4-tetrahidropiranilgrupa, 2-, 3- vai 4-piridi-nilgrupa.
- 3. Savienojums pec punkta 1, kura R ir nenoteikti aizvietota cikloheksilgrupa vai 1^, 2- vai 3-cikloheksenilgrupa. 11
- 4. Savienojums pēc punkta 1, kura R ir grupa -CH^-R un R . ir neobligāti aizvietota ciklopentilgrupa, cikloheksilgrupa, ciklohep-tilgrupa, 1- vai 2-adamantilgrupa, 1- vai 2-noradamantilgrupa, 1-nor-bornanilgrupa, 2-ekso-norbornanilgrupa, 1- vai 2-biciklo^.2.2Jokta- nilgrupa, 1-, 2-, 3-, 6- vai 8-biciklo[3.2. ljoktanilgrupa, 1-, 2-, 3-vai 9-biciklo[3.3.1]nonanilgrupa, 1- vai 2-norbornenilgrupa.
- 5. Savienojums ar formulu (I)kura: R1 ir H, NH2 vai 0CH3; 2 R ir neobligāti aizvietota cikliska grupa ar 5 - 7 oglekļa atomiem, kas neobligāti satur vienu vai vairākus heteroatomus; 3 4 R un R neatkarīgi viens no otra ir ūdeņraža atoms vai C^_^-al-kilgrupa; m ir 0 - 4; n ir 0 - 6; p ir 0 - 1; X ir CN, CSNH2,P0(0H)2, COOH, SC>2NH2, NH2> OH, C(=NH)NH2, tetr- azolilgrupa, triazolilgrupa, grupa COR^, kurā s R ir C^^-alkilgrupa, CF^, NH2» OC^-alkilgrupa; Y ir 0 vai NH. LV 10100 1 3 4
- 6. Savienojums pēc punkta 5, kura R ir NH^, R un R ir H, Jv m ir 0 unMr 1. 2
- 7. Savienojums pēc punkta 5, kurā R ir fenilgrupa.
- 8. Savienojums pēc punkta 5, kurā X ir CN, C00H vai C0NH2. 2
- 9. Savienojums pec punkta 5, kurā R ir nenoteikti aizvietota 5- vai 6-locekļu aromātiska vai heteroaromātiska grupa, vai nenoteikti aizvietota alicikliska grupa vai heteroalicikliska grupa ar 5 - 9 atomiem ciklā.
- 10. selektīvai T-limfocītu funkciju pavājināšanai zīdītāju organismā bez humorālās imunitātes pavājināšanas, kas atšķiras ar to, ka zīdītājam ievada savienojumu pēc jebkura no punktiem 1-9, kas inhibē purinu nukleozīdfosforilāzi un līdz ar to T-limfocītu veidošanos.
- 11. ķīmiskā savienojuma iegūšanai, kas atšķiras ar to, ka veic: a) nenoteikti aizvietota cikliskā aldehīda reakciju ar ciān-etiķskābi amonija acetāta klātienē, iegūstot 3-cikloaizvietotu pentāndinitrilu; b) 3-cikloaizvietota pentāndinitrila reakciju ar alkilformiātu bāzes klātienē, iegūstot 3-cikloaizvietotu-2-formilpentāndinitrilu; c) 3-cikloaizvietota-2-formilpentāndinitrila reakciju ar gli-cīna metilestera hidrogenhlorīdu un nātrija vai amonija acetātu, ie- gūstot N-[(3-cikloaizvietotu-2,4-diciān)-2-butenil]glicīna metil-esteri; d) N-[(3-cikloaizvietota-2,4-diciān)-2-butenil]glicīna m$til-estera reakciju ar hlorskudrskābes alkilesteri DBN vai DBU klātienē, iegūstot 3-amino-4-(2-ciān-l-cikloaizvietotu-etil)-l-etil-lH-plrol- 1.2- dikarbonskābes metilesteri; e) 3-amino-4-(2-ciān-l-cikloaizvietota-etil)-l-etil-lH-pirol- 1.2- dikarbonskābes metilestera reakciju ar bāzi, iegūstot 3-amino-4-(2-ciān-l-cikloaizvietotu-etil)-l-etil-lH-pirol-2-karbonskābes metilesteri.
- 12. Pēc punkta 11, kas atšķiras ar to, ka veic šādas papildreakcijas: f) 3-amino-4- (2-ciān-l-cikloaizvietota-etil)-l-etil-lH-pirol- 2-karbonskābes metilestera reakciju ar benzoilizotiocianātu, iegūstot N-benzoil-N’ -[4-(2-ciān-l-cikloaizvietotu-etil)-2-metoksi-karbonil-lH-pirol-3-il] tiourīnvielu; g) N-benzoil-N’-[4-(2-ciān-l-cikloaizvietotas-etil)-2-metoksi-karbonil-lH-pirol-3-il]tiourīnvielas reakciju ar alkilhalogenīdu, iegūstot N-benzoil-N’ -[4-(2-ciān-l-cikloaizvietotu-etil)-2-metoksikar-bonil-lH-pirol-3-il]-S-alkil tiourīnvielu; h) N-benzoil-N’-[4-(2-cian-l-cikloaizvietotas-etil)-2-metoksi-karbonil-lH-pirol-3-il]-S-alkiltiourīnvielas reakciju ar amonjaka šķīdumu metanolā vai etanolā, iegūstot 3-cikloaizvietota-3-(2-amino-4-okso-3H,5H-pirolo[3,2-d]pirimidin-7-il)propānnitrila un 3-cikloaiz-vietota-3-(2-metilmerkapto-4-okso-3H, 5H-pirolo[3,2-d]pirimidin-7-il)-propānnitrila maisījumu.
- 13. Panemiens pēc punkta 12, kas atšķiras ar to, ka veic šādas papildreakcijas: i) 3-cikloaiZ/'Vietota-3-(2-metilmerkapto-4-okso-3H, 5H-pirolo-[3,2-d]pirimidin-7-il)propānnitrila reakciju ar oksidētāju, iegūstot 3-cikloaizvietotu-3-(2-metilsulfonil-4-okso-3H,5H-pirolo [3,2-dlpiri-midin-7-il)propānnitrilu; j) 3-cikloaizvietota-3-(2-metilsulfonil-4-okso-3H,5H-pirolo-[3,2-d]pirimidin-7-il)propānnitrila reakciju ar nātrija alkoksīdu, iegūstot 3-cikloaizvietotu-3-(2-metoksi-4-okso-3H,5H-pirolo[3,2-d]-pirimidin-7-il)propānnitrilu.
- 14. Paņēmiens pēc punkta 11, kas atšķiras ar to, ka veic šādas papildreakcijas: f) 3-amino-4- (2-ciān-l-cikloaizvietota-etil)-l-etil-lH-pirol- 2-karbonskābes metilestera reakciju ar dimētilformamīda dimēti lace tālu, iegūstot 4-(2-ciān-l-cikloaizvietotu-etil)-3-[N-(dimetil-aminometi 1 ēn)amino]-1 H-pirο 1 -2-karbonskābes metilesteri; g) 4-(2-ciān-l-cikloaizvietota-etil)-3-[N-(dimetil-aminometi-lēn)amino]-lH-pirol-2-karbonskābes metilestera reakciju ar amonjaka šķīdumu metanolā, iegūstot 3-cikloaizvietotu-3-(4-okso-3H,5H-pirolo-[3,2-d]pirimidin-7-il )propānnitrilu.
- 15. Paņēmiens pēc punkta 11, kas atšķiras ar to, ka cikliskais aizvietotājs ir fenilgrupa, 2- vai 3- tienilgrupa, 2- vai 3-furanilgrupa, 2-, 3- vai 4-piridinilgrupa, 2- vai 3-pirolilgrupa, 2-, 4- vai 5-tiazolilgrupa, 2- vai 3-pirazinilgru'pa, 3- vai 4-pirid-azinilgrupa, 3-, 4- vai pirazolilgrupa, 1- vai 2-adamantilgrupa, cik- lopentilg'rupa, cikloheksilgrupa, cikloheptilgrupa vai morfolinilgrupa.
- 16. Savienojumi, kuros R 1 un R nozīmes atbilst punkta 5 dotām: R2 :nr* CN HOCN LV 10100Me
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/429,098 US4985434A (en) | 1989-10-31 | 1989-10-31 | 7-substituted derivatives of 2-amino-3H,5H-pyrrolo(3,2-d)pyrimidin-4-ones and pharamceutical uses and compositions containing the same |
US07/429,097 US5008270A (en) | 1989-10-31 | 1989-10-31 | 2-amino-7-(heterocyclomethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same |
US07/429,099 US5008265A (en) | 1989-10-31 | 1989-10-31 | 2-amino-7-(alicyclomethyl)-3H,5H,-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same |
US07/429,100 US4985433A (en) | 1989-10-31 | 1989-10-31 | 2-amino-7-(pyridinylmethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same |
US44279889A | 1989-11-29 | 1989-11-29 | |
PCT/US1990/005756 WO1991006548A1 (en) | 1989-10-31 | 1990-10-12 | Inhibitors of purine nucleoside phosphorylase |
Publications (2)
Publication Number | Publication Date |
---|---|
LV10100A LV10100A (lv) | 1994-05-10 |
LV10100B true LV10100B (en) | 1995-08-20 |
Family
ID=27541578
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LVP-93-342A LV10100B (en) | 1989-10-31 | 1993-05-14 | Inhibitors of purine nucleoside phosphorylase |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0500653A4 (lv) |
JP (1) | JP2866478B2 (lv) |
AU (1) | AU654264B2 (lv) |
CA (1) | CA2072123C (lv) |
FI (1) | FI103972B (lv) |
HU (1) | HUT61765A (lv) |
LV (1) | LV10100B (lv) |
NO (1) | NO301423B1 (lv) |
WO (1) | WO1991006548A1 (lv) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5726311A (en) * | 1989-11-29 | 1998-03-10 | Biocryst Pharmaceuticals, Inc. | 7-disubstituted-methyl-4-oxo-3H,5H-pyrrolo 3,2-d!pyrimidine and pharmaceutical uses and compositions containing the same |
US5236926A (en) * | 1992-02-03 | 1993-08-17 | Warner-Lambert Company | 9-substituted-8-halo or -8-hydroxy-9-deazaguanines as inhibitors or PNP for pharmaceutical compositions |
HUT71559A (en) * | 1992-04-21 | 1995-12-28 | Biocryst Pharm Inc | 4-oxo-3h,5h-pyrrolo[3,2-d]pyrimidine and pharmaceutical compositions containing them |
HUT77436A (hu) * | 1994-10-05 | 1998-04-28 | Darwin Discovery Limited | Purin- és guaninszármazékok, eljárás előállításukra, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk gyógyszerkészítmények előállítására |
GB9520364D0 (en) * | 1995-10-05 | 1995-12-06 | Chiroscience Ltd | Compouundds |
GB9520363D0 (en) * | 1995-10-05 | 1995-12-06 | Chiroscience Ltd | Compounds |
JP2002500658A (ja) * | 1997-05-29 | 2002-01-08 | ノバルティス アクチエンゲゼルシャフト | 2−アミノ−7−(1−置換−2−ヒドロキシエチル)−3,5−ジヒドロピロロ[3,2−d]ピリミジン−4−オン |
US6174888B1 (en) | 1998-05-28 | 2001-01-16 | Novartis Ag | 2-amino-7-(1-substituted-2-hydroxyethyl)-3,5-dihydropyrrolo[3,2-D]pyrimidin-4-ones |
JP4496586B2 (ja) * | 2000-01-24 | 2010-07-07 | 日産化学工業株式会社 | キノリルアクリロニトリルの製造法及びその中間体 |
EP1539783B1 (en) * | 2002-08-21 | 2011-04-13 | Albert Einstein College Of Medicine Of Yeshiva University | Inhibitors of nucleoside phosphorylases and nucleosidases |
NZ523970A (en) * | 2003-02-04 | 2005-02-25 | Ind Res Ltd | Process for preparing inhibitors of nucleoside phoshorylases and nucleosidases |
WO2009079797A1 (en) | 2007-12-26 | 2009-07-02 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
WO2010006438A1 (en) | 2008-07-17 | 2010-01-21 | Critical Outcome Technologies Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
US8987272B2 (en) | 2010-04-01 | 2015-03-24 | Critical Outcome Technologies Inc. | Compounds and method for treatment of HIV |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5988484A (ja) * | 1982-11-09 | 1984-05-22 | Takeda Chem Ind Ltd | 新規7−デアザプリン誘導体 |
IE60433B1 (en) * | 1986-08-26 | 1994-07-13 | Warner Lambert Co | Novel 9-deazaguanines |
CA1294960C (en) * | 1986-10-24 | 1992-01-28 | Thomas C. Malone | 7-deazaguanines as immunomodulators |
US4921858A (en) * | 1986-10-24 | 1990-05-01 | Warner-Lambert Company | 7-deazaguanines as immunomodulators |
DE3726044A1 (de) * | 1987-02-11 | 1988-08-25 | Bayer Ag | Akarizide mittel auf basis von azomethinderivaten und azomethine des 2,3-diaminomaleinsaeurenitrils |
US4927830A (en) * | 1988-04-08 | 1990-05-22 | The Regents Of The University Of Michigan | Acyclic pyrrolo[2,3-D]pyrimidine analogs as antiviral agents |
DK0460116T3 (da) * | 1989-02-27 | 1998-03-30 | Biocryst Pharm Inc | 9-substitueret-8-usubstitueret-9-deazaguaniner |
US4985433A (en) * | 1989-10-31 | 1991-01-15 | Biocryst, Inc. | 2-amino-7-(pyridinylmethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same |
US4985434A (en) * | 1989-10-31 | 1991-01-15 | Biocryst, Inc. | 7-substituted derivatives of 2-amino-3H,5H-pyrrolo(3,2-d)pyrimidin-4-ones and pharamceutical uses and compositions containing the same |
-
1990
- 1990-10-12 CA CA002072123A patent/CA2072123C/en not_active Expired - Fee Related
- 1990-10-12 EP EP90916628A patent/EP0500653A4/en not_active Withdrawn
- 1990-10-12 HU HU9201450A patent/HUT61765A/hu unknown
- 1990-10-12 WO PCT/US1990/005756 patent/WO1991006548A1/en not_active Application Discontinuation
- 1990-10-12 JP JP2515550A patent/JP2866478B2/ja not_active Expired - Lifetime
- 1990-10-12 AU AU67125/90A patent/AU654264B2/en not_active Ceased
-
1992
- 1992-04-28 FI FI921900A patent/FI103972B/fi active
- 1992-04-29 NO NO921679A patent/NO301423B1/no not_active IP Right Cessation
-
1993
- 1993-05-14 LV LVP-93-342A patent/LV10100B/en unknown
Also Published As
Publication number | Publication date |
---|---|
JPH05504551A (ja) | 1993-07-15 |
EP0500653A4 (en) | 1995-08-23 |
CA2072123A1 (en) | 1991-05-01 |
LV10100A (lv) | 1994-05-10 |
WO1991006548A1 (en) | 1991-05-16 |
HU9201450D0 (en) | 1992-09-28 |
JP2866478B2 (ja) | 1999-03-08 |
HUT61765A (en) | 1993-03-01 |
FI103972B1 (fi) | 1999-10-29 |
AU6712590A (en) | 1991-05-31 |
CA2072123C (en) | 2001-06-12 |
EP0500653A1 (en) | 1992-09-02 |
NO921679D0 (no) | 1992-04-29 |
FI103972B (fi) | 1999-10-29 |
AU654264B2 (en) | 1994-11-03 |
FI921900A0 (fi) | 1992-04-28 |
FI921900A (fi) | 1992-04-28 |
NO301423B1 (no) | 1997-10-27 |
NO921679L (no) | 1992-06-17 |
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