NO301423B1 - Analogifremgangsmåte for fremstilling av inhibitorer av purin nukleosid fosforylase - Google Patents
Analogifremgangsmåte for fremstilling av inhibitorer av purin nukleosid fosforylase Download PDFInfo
- Publication number
- NO301423B1 NO301423B1 NO921679A NO921679A NO301423B1 NO 301423 B1 NO301423 B1 NO 301423B1 NO 921679 A NO921679 A NO 921679A NO 921679 A NO921679 A NO 921679A NO 301423 B1 NO301423 B1 NO 301423B1
- Authority
- NO
- Norway
- Prior art keywords
- substituted
- compound
- pyrrole
- amino
- pyrimidin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 13
- 239000000784 purine nucleoside phosphorylase inhibitor Substances 0.000 title claims description 4
- -1 3-substituted propanenitrile Chemical class 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 94
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 42
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 29
- 239000000047 product Substances 0.000 claims description 28
- 239000011734 sodium Substances 0.000 claims description 24
- 150000002081 enamines Chemical class 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 18
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 17
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 claims description 14
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- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 claims description 12
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- 229910021529 ammonia Inorganic materials 0.000 claims description 9
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- 235000019257 ammonium acetate Nutrition 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 150000001350 alkyl halides Chemical class 0.000 claims description 8
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 7
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
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- 229940123827 Purine nucleoside phosphorylase inhibitor Drugs 0.000 claims description 3
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- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 2
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- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
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Classifications
-
- 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
Landscapes
- 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)
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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO921679D0 NO921679D0 (no) | 1992-04-29 |
| NO921679L NO921679L (no) | 1992-06-17 |
| NO301423B1 true NO301423B1 (no) | 1997-10-27 |
Family
ID=27541578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO921679A NO301423B1 (no) | 1989-10-31 | 1992-04-29 | Analogifremgangsmåte for fremstilling av inhibitorer av purin nukleosid fosforylase |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0500653A4 (de) |
| JP (1) | JP2866478B2 (de) |
| AU (1) | AU654264B2 (de) |
| CA (1) | CA2072123C (de) |
| FI (1) | FI103972B (de) |
| HU (1) | HUT61765A (de) |
| LV (1) | LV10100B (de) |
| NO (1) | NO301423B1 (de) |
| WO (1) | WO1991006548A1 (de) |
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 |
| 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 (de) * | 1997-05-29 | 2000-03-22 | Novartis AG | 2-amino-7-(1-substituierte-2-hydroxyethyl)-3,5-dihydroxypyrrolo[3,2-d]pyrimdin-4-one |
| 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 (de) * | 2002-08-21 | 2011-04-13 | Albert Einstein College Of Medicine Of Yeshiva University | Inhibitoren von nukleosidphosphorylasen und nukleosidasen |
| NZ523970A (en) * | 2003-02-04 | 2005-02-25 | Ind Res Ltd | Process for preparing inhibitors of nucleoside phoshorylases and nucleosidases |
| EP2225226B1 (de) | 2007-12-26 | 2016-08-17 | Critical Outcome Technologies, Inc. | Verbindungen und ihre verwending in einem verfahren zur behandlung von krebs |
| CA2730890C (en) | 2008-07-17 | 2018-05-15 | Critical Outcome Technologies Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| EP3235818A3 (de) | 2010-04-01 | 2018-03-14 | Critical Outcome Technologies, Inc. | Verbindungen zur behandlung von 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 |
| 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 (de) * | 1989-02-27 | 1997-08-27 | Biocryst Pharmaceuticals Inc. | 9-substituierte-8-unsubstituierte-9-deazaguanine |
| 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 |
-
1990
- 1990-10-12 HU HU9201450A patent/HUT61765A/hu unknown
- 1990-10-12 JP JP2515550A patent/JP2866478B2/ja not_active Expired - Lifetime
- 1990-10-12 EP EP90916628A patent/EP0500653A4/en not_active Withdrawn
- 1990-10-12 WO PCT/US1990/005756 patent/WO1991006548A1/en not_active Application Discontinuation
- 1990-10-12 CA CA002072123A patent/CA2072123C/en not_active Expired - Fee Related
- 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 |
|---|---|
| LV10100A (lv) | 1994-05-10 |
| NO921679D0 (no) | 1992-04-29 |
| JPH05504551A (ja) | 1993-07-15 |
| 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 |
| LV10100B (en) | 1995-08-20 |
| 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 (de) | 1992-09-02 |
| CA2072123A1 (en) | 1991-05-01 |
| FI103972B (fi) | 1999-10-29 |
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| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN APRIL 2002 |