DD255351A5 - Verfahren zur herstellung von carbocyclischen purinnucleosiden - Google Patents

Verfahren zur herstellung von carbocyclischen purinnucleosiden Download PDF

Info

Publication number: DD255351A5
Authority: DD; German Democratic Republic
Prior art keywords: compound; formula; hydroxyl group; preparation; acid
Prior art date: 1986-03-06

Application number

DD87300535A

Other languages

German (de)

English (en)

Inventor

Yoshio Taniyama

Takumi Hamana

Ryuji Marumoto

Naoki Yamamoto

Original Assignee

Takeda Chemical Industries Ltd,Jp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-03-06

Filing date

1987-03-06

Publication date

1988-03-30

1987-03-06 Application filed by Takeda Chemical Industries Ltd,Jp filed Critical Takeda Chemical Industries Ltd,Jp

1988-03-30 Publication of DD255351A5 publication Critical patent/DD255351A5/de

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 18
239000002777 nucleoside Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 68
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 5
-1 hypoxanthine-9-yl Chemical group 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 12
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 8
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 6
UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
238000006722 reduction reaction Methods 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
UXRSUBXVCCYDKK-UHFFFAOYSA-N 1-(7h-purin-2-yl)ethanone Chemical compound CC(=O)C1=NC=C2NC=NC2=N1 UXRSUBXVCCYDKK-UHFFFAOYSA-N 0.000 claims 1
PMPFSQREEWMOPZ-RQJHMYQMSA-N 2-amino-9-[(1s,3r)-3-(hydroxymethyl)cyclopentyl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1CC[C@@H](CO)C1 PMPFSQREEWMOPZ-RQJHMYQMSA-N 0.000 claims 1
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 1
229910000083 tin tetrahydride Inorganic materials 0.000 claims 1
SKLQBHROODDCHR-UHFFFAOYSA-N trityltin Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([Sn])C1=CC=CC=C1 SKLQBHROODDCHR-UHFFFAOYSA-N 0.000 claims 1
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UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 13
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125000002103 4,4'-dimethoxytriphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)(C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 5
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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238000004458 analytical method Methods 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
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238000006243 chemical reaction Methods 0.000 description 3
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 3
239000008187 granular material Substances 0.000 description 3
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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239000002609 medium Substances 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
XUGWUUDOWNZAGW-UHFFFAOYSA-N neplanocin A Natural products C1=NC=2C(N)=NC=NC=2N1C1C=C(CO)C(O)C1O XUGWUUDOWNZAGW-UHFFFAOYSA-N 0.000 description 1
208000020470 nervous system symptom Diseases 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
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239000006072 paste Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000003834 purine nucleoside derivatives Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000000527 sonication Methods 0.000 description 1
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239000007921 spray Substances 0.000 description 1
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239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical class [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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230000003612 virological effect Effects 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
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229940075420 xanthine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DD87300535A 1986-03-06 1987-03-06 Verfahren zur herstellung von carbocyclischen purinnucleosiden DD255351A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4939586		1986-03-06

Publications (1)

Publication Number	Publication Date
DD255351A5 true DD255351A5 (de)	1988-03-30

Family

ID=12829840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87300535A DD255351A5 (de)	1986-03-06	1987-03-06	Verfahren zur herstellung von carbocyclischen purinnucleosiden

Country Status (5)

Country	Link
JP (1)	JPS6310787A (cs)
KR (1)	KR870008911A (cs)
CS (1)	CS264290B2 (cs)
DD (1)	DD255351A5 (cs)
SU (1)	SU1561826A3 (cs)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2004270201A1 (en)	2003-09-05	2005-03-17	3M Innovative Properties Company	Treatment for CD5+ B cell lymphoma
US7544697B2 (en)	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
AR046046A1 (es)	2003-10-03	2005-11-23	3M Innovative Properties Co	Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas.
CA2547020C (en)	2003-11-25	2014-03-25	3M Innovative Properties Company	1h-imidazo[4,5-c]pyridine-4-amine derivatives as immune response modifier
US8017779B2 (en)	2004-06-15	2011-09-13	3M Innovative Properties Company	Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
WO2006065280A2 (en)	2004-06-18	2006-06-22	3M Innovative Properties Company	Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods
WO2006038923A2 (en)	2004-06-18	2006-04-13	3M Innovative Properties Company	Aryl substituted imidazonaphthyridines
US8026366B2 (en)	2004-06-18	2011-09-27	3M Innovative Properties Company	Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines
JP5543068B2 (ja)	2004-12-30	2014-07-09	スリーエムイノベイティブプロパティズカンパニー	キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物
EP1831221B1 (en)	2004-12-30	2012-08-08	3M Innovative Properties Company	Substituted chiral fused 1,2 imidazo 4,5-c ring compounds
AU2006210392A1 (en)	2005-02-04	2006-08-10	Coley Pharmaceutical Group, Inc.	Aqueous gel formulations containing immune response modifiers
AU2006213746A1 (en)	2005-02-11	2006-08-17	Coley Pharmaceutical Group, Inc.	Oxime and hydroxylamine substituted imidazo(4,5-c) ring compounds and methods
EP1869043A2 (en)	2005-04-01	2007-12-26	Coley Pharmaceutical Group, Inc.	Pyrazolopyridine-1,4-diamines and analogs thereof
AU2006232375A1 (en)	2005-04-01	2006-10-12	Coley Pharmaceutical Group, Inc.	1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases
US7906506B2 (en)	2006-07-12	2011-03-15	3M Innovative Properties Company	Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods

1987
- 1987-02-05 JP JP62025074A patent/JPS6310787A/ja active Pending
- 1987-03-05 SU SU874202204A patent/SU1561826A3/ru active
- 1987-03-06 DD DD87300535A patent/DD255351A5/de not_active IP Right Cessation
- 1987-03-06 CS CS871517A patent/CS264290B2/cs unknown
- 1987-03-06 KR KR870002029A patent/KR870008911A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
KR870008911A (ko)	1987-10-22
CS264290B2 (en)	1989-06-13
JPS6310787A (ja)	1988-01-18
SU1561826A3 (ru)	1990-04-30
CS151787A2 (en)	1988-09-16

Legal Events

Date	Code	Title	Description
1995-08-03	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
AU596400B2 (en)	1990-05-03	Carbocyclic purine nucleosides, their production and use
DE69330274T2 (de)	2001-11-15	Enantiomerisch reine beta-d-dioxolan-nukleoside
DE69034119T2 (de)	2004-08-26	Substituierte-1,3-Oxathiolane mit antiviraler Wirkung
DE69116750T2 (de)	1996-11-14	9-Purinyl-Phosphonsäurederivate
DE3850645T2 (de)	1994-10-27	Puringruppen enthaltende Cyclobutane.
DE68920413T2 (de)	1995-05-11	Carbocyclische Nukleoside und Nukleotide.
DE69425574T2 (de)	2001-01-04	L-2',3'-dideoxy-nukleosidanaloga als anti-hepatitis b-(hbv) und anti-hiv-wirkstoffe
DE69806919T2 (de)	2003-02-27	Antivirale pyrimidin-nukleosid-analogen
AT390000B (de)	1990-02-26	Verwendung von 3'-azido-3'-desoxythymidin oder eines pharmazeutisch annehmbaren derivats hievon zur herstellung von medikamenten
DE69122264T2 (de)	1997-02-06	Substituierte 1,3-oxathiolane mit antiviralen eigenschaften
DE69109482T2 (de)	1996-02-15	Pyrimidinnucleosidderivat.
DD255351A5 (de)	1988-03-30	Verfahren zur herstellung von carbocyclischen purinnucleosiden
EP0626387A1 (de)	1994-11-30	Nukleoside und Oligonukleotide mit 2'-Ethergruppen
WO1993016091A1 (de)	1993-08-19	Neue liponucleotide, deren herstellung sowie deren verwendung als antivirale arzneimittel
EP0286028A2 (de)	1988-10-12	Desaza-purin-nucleosid-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung bei der Nucleinsäure-Sequenzierung sowie als antivirale Mittel
EP0545966A1 (de)	1993-06-16	Neue phospholipid-derivate von nucleosiden, deren herstellung sowie deren verwendung als antivirale arzneimittel.
EP0679657A2 (de)	1995-11-02	Nukleoside und Oligonukleotide mit 2'-Ethergruppen
CH626363A5 (cs)	1981-11-13
DD297650A5 (de)	1992-01-16	Verfahren zur herstellung von fluor-substituierten purin-nucleosiden und sie enthaltender pharmazeutischer zubereitungen
DE2915254A1 (de)	1979-11-15	Neue chemische verbindungen, verfahren zu deren herstellung und deren verwendung als arzneimittel mit antiviraler wirkung
DE3887014T2 (de)	1994-05-19	Nukleoside, ihre Herstellung und pharmazeutische Zusammenstellungen.
DE69430587T2 (de)	2003-01-09	Pyrimidin-acyclonukleosid-derivate
DE68918804T2 (de)	1995-02-23	Acyclische 6-substituierte pyrimidin nukleosid-abkömmlinge und antivirale mittel, die dieselben als aktive mittel enthalten.
EP0219838A2 (en)	1987-04-29	Carbocyclic purine nucleosides, their production and use
DE68927651T2 (de)	1997-06-05	Derivate von Fluorphosphonat-Nukleotiden