LV10100B - Inhibitors of purine nucleoside phosphorylase - Google Patents

Inhibitors of purine nucleoside phosphorylase Download PDF

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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
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LV
Latvia
Prior art keywords
compound
cyclo
ethyl
substituted
amino
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LVP-93-342A
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English (en)
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LV10100A (lv
Inventor
Secrist John A Iii
Erion Mark David
John A Montgomery
Steven E Ealick
Wayne C Guida
Niwas Shri
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Biocryst Pharm Inc
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Priority claimed from US07/429,098 external-priority patent/US4985434A/en
Priority claimed from US07/429,097 external-priority patent/US5008270A/en
Priority claimed from US07/429,100 external-priority patent/US4985433A/en
Priority claimed from US07/429,099 external-priority patent/US5008265A/en
Application filed by Biocryst Pharm Inc filed Critical Biocryst Pharm Inc
Publication of LV10100A publication Critical patent/LV10100A/lv
Publication of LV10100B publication Critical patent/LV10100B/en

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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

Claims (16)

  1. 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. 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. 3. Savienojums pec punkta 1, kura R ir nenoteikti aizvietota cikloheksilgrupa vai 1^, 2- vai 3-cikloheksenilgrupa. 11
  4. 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. 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. 6. Savienojums pēc punkta 5, kura R ir NH^, R un R ir H, Jv m ir 0 unMr 1. 2
  7. 7. Savienojums pēc punkta 5, kurā R ir fenilgrupa.
  8. 8. Savienojums pēc punkta 5, kurā X ir CN, C00H vai C0NH2. 2
  9. 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. 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. 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. 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. 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. 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. 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. 16. Savienojumi, kuros R 1 un R nozīmes atbilst punkta 5 dotām: R2 :nr* CN HO
    CN LV 10100
    Me
LVP-93-342A 1989-10-31 1993-05-14 Inhibitors of purine nucleoside phosphorylase LV10100B (en)

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
US07/429,100 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
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
US44279889A 1989-11-29 1989-11-29
PCT/US1990/005756 WO1991006548A1 (en) 1989-10-31 1990-10-12 Inhibitors of purine nucleoside phosphorylase

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LV10100A LV10100A (lv) 1994-05-10
LV10100B true LV10100B (en) 1995-08-20

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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)

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* Cited by examiner, † Cited by third party
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
CA2133346A1 (en) * 1992-04-21 1993-10-28 Shri Niwas 7-disubstituted-methyl-4-oxo-3h,5h-pyrrolo[3,2-d]pyrimidine and pharmaceutical uses and compositions containing the same
AU695032B2 (en) * 1994-10-05 1998-08-06 Darwin Discovery Limited Purine and guanine compounds as inhibitors of PNP
GB9520364D0 (en) * 1995-10-05 1995-12-06 Chiroscience Ltd Compouundds
GB9520363D0 (en) * 1995-10-05 1995-12-06 Chiroscience Ltd Compounds
EP0986563A1 (en) * 1997-05-29 2000-03-22 Novartis AG 2-amino-7-(1-substituted-2-hydroxyethyl)-3,5-dihydro-pyrrolo 3,2-d]pyrimidin-4-ones
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
EP2225226B1 (en) 2007-12-26 2016-08-17 Critical Outcome Technologies, Inc. Compounds and their use in a method for treatment of cancer
CA2730890C (en) 2008-07-17 2018-05-15 Critical Outcome Technologies Inc. Thiosemicarbazone inhibitor compounds and cancer treatment methods
EP3235818A3 (en) 2010-04-01 2018-03-14 Critical Outcome Technologies, Inc. Compounds for the treatment of hiv

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* Cited by examiner, † Cited by third party
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
CA1293727C (en) * 1986-08-26 1991-12-31 Catherine Rose Kostlan 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
EP0460116B1 (en) * 1989-02-27 1997-08-27 Biocryst Pharmaceuticals Inc. 9-substituted-8-unsubstituted-9-deazaguanines
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
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

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LV10100A (lv) 1994-05-10
NO921679D0 (no) 1992-04-29
JPH05504551A (ja) 1993-07-15
NO301423B1 (no) 1997-10-27
FI921900A (fi) 1992-04-28
EP0500653A4 (en) 1995-08-23
CA2072123C (en) 2001-06-12
NO921679L (no) 1992-06-17
HU9201450D0 (en) 1992-09-28
FI103972B1 (fi) 1999-10-29
AU654264B2 (en) 1994-11-03
JP2866478B2 (ja) 1999-03-08
WO1991006548A1 (en) 1991-05-16
HUT61765A (en) 1993-03-01
FI921900A0 (fi) 1992-04-28
AU6712590A (en) 1991-05-31
EP0500653A1 (en) 1992-09-02
CA2072123A1 (en) 1991-05-01
FI103972B (fi) 1999-10-29

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