CS264290B2 - Process for preparing carbocyclic nucleosides of purine - Google Patents

Process for preparing carbocyclic nucleosides of purine Download PDF

Info

Publication number: CS264290B2
Authority: CS; Czechoslovakia
Prior art keywords: compound; mmol; dissolved; formula; added
Prior art date: 1986-03-06

Application number

CS871517A

Other languages

Czech (cs)

English (en)

Other versions

CS151787A2 (en

Inventor

Yoshio Taniyama

Takumi Hamana

Ryuji Marumoto

Naoki Yamamoto

Original Assignee

Takeda Chemical Industries Ltd

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

1989-06-13

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

1988-09-16 Publication of CS151787A2 publication Critical patent/CS151787A2/cs

1989-06-13 Publication of CS264290B2 publication Critical patent/CS264290B2/cs

Links

KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 3
239000002777 nucleoside Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 58
238000000034 method Methods 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
-1 dimethoxytrityl group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
125000000848 adenin-9-yl group Chemical group [H]N([H])C1=C2N=C([H])N(*)C2=NC([H])=N1 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000002212 purine nucleoside Substances 0.000 claims description 6
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 6
125000002837 carbocyclic group Chemical group 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
125000003738 guanin-9-yl group Chemical group O=C1N([H])C(N([H])[H])=NC2=C1N=C([H])N2[*] 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
239000000243 solution Substances 0.000 description 28
239000000203 mixture Substances 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
229910001868 water Inorganic materials 0.000 description 24
239000002904 solvent Substances 0.000 description 22
230000000052 comparative effect Effects 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
210000004027 cell Anatomy 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
238000004587 chromatography analysis Methods 0.000 description 13
239000000047 product Substances 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 12
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 12
239000000843 powder Substances 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
238000000921 elemental analysis Methods 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000126 substance Substances 0.000 description 8
241000700605 Viruses Species 0.000 description 7
239000013078 crystal Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000006188 syrup Substances 0.000 description 7
235000020357 syrup Nutrition 0.000 description 7
UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
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
235000011054 acetic acid Nutrition 0.000 description 5
AFQIYTIJXGTIEY-UHFFFAOYSA-N hydrogen carbonate;triethylazanium Chemical compound OC(O)=O.CCN(CC)CC AFQIYTIJXGTIEY-UHFFFAOYSA-N 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
208000036142 Viral infection Diseases 0.000 description 4
239000003443 antiviral agent Substances 0.000 description 4
239000000872 buffer Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
VWCUMTCXBIRRSG-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2-methoxybenzene Chemical compound COC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 VWCUMTCXBIRRSG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
108020004414 DNA Proteins 0.000 description 3
102000053602 DNA Human genes 0.000 description 3
241000598436 Human T-cell lymphotropic virus Species 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000000840 anti-viral effect Effects 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000007853 buffer solution Substances 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
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
241001493065 dsRNA viruses Species 0.000 description 3
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000001308 synthesis method Methods 0.000 description 3
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
230000003612 virological effect Effects 0.000 description 3
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 description 2
241000220479 Acacia Species 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241000450599 DNA viruses Species 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical class O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
RBHODKISOUZAKB-UHFFFAOYSA-N [methylperoxy(diphenyl)methyl]benzene Chemical group C=1C=CC=CC=1C(C=1C=CC=CC=1)(OOC)C1=CC=CC=C1 RBHODKISOUZAKB-UHFFFAOYSA-N 0.000 description 2
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125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
230000000120 cytopathologic effect Effects 0.000 description 2
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
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125000003147 glycosyl group Chemical group 0.000 description 2
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125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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239000007937 lozenge Substances 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
239000011976 maleic acid Substances 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 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
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PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
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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
239000002689 soil Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
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229960005322 streptomycin Drugs 0.000 description 1
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DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
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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)

CS871517A 1986-03-06 1987-03-06 Process for preparing carbocyclic nucleosides of purine CS264290B2 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
CS151787A2 CS151787A2 (en)	1988-09-16
CS264290B2 true CS264290B2 (en)	1989-06-13

Family

ID=12829840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS871517A CS264290B2 (en)	1986-03-06	1987-03-06	Process for preparing carbocyclic nucleosides of purine

Country Status (5)

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

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.
MXPA06005910A (es)	2003-11-25	2006-08-23	3M Innovative Properties Co	Sistemas de anillo imidazo sustituido y metodos.
WO2005123080A2 (en)	2004-06-15	2005-12-29	3M Innovative Properties Company	Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
US7897609B2 (en)	2004-06-18	2011-03-01	3M Innovative Properties Company	Aryl substituted imidazonaphthyridines
WO2006065280A2 (en)	2004-06-18	2006-06-22	3M Innovative Properties Company	Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods
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
ES2392648T3 (es)	2004-12-30	2012-12-12	3M Innovative Properties Company	Compuestos quirales sustituidos que contienen un núcleo 1,2-imidazo-4,5-c condensado
CA2597092A1 (en)	2005-02-04	2006-08-10	Coley Pharmaceutical Group, Inc.	Aqueous gel formulations containing immune reponse modifiers
CA2597587A1 (en)	2005-02-11	2006-08-17	Coley Pharmaceutical Group, Inc.	Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods
JP2008538550A (ja)	2005-04-01	2008-10-30	コーリーファーマシューティカルグループ，インコーポレイテッド	ウイルス感染および腫瘍性疾患を処置するためのサイトカイン生合成の調節因子としての１−置換ピラゾロ（３，４−ｃ）環状化合物
US7943610B2 (en)	2005-04-01	2011-05-17	3M Innovative Properties Company	Pyrazolopyridine-1,4-diamines and analogs thereof
WO2008008432A2 (en)	2006-07-12	2008-01-17	Coley Pharmaceutical Group, Inc.	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 CS CS871517A patent/CS264290B2/cs unknown
- 1987-03-06 KR KR870002029A patent/KR870008911A/ko not_active Withdrawn
- 1987-03-06 DD DD87300535A patent/DD255351A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR870008911A (ko)	1987-10-22
JPS6310787A (ja)	1988-01-18
DD255351A5 (de)	1988-03-30
CS151787A2 (en)	1988-09-16
SU1561826A3 (ru)	1990-04-30

Publication	Publication Date	Title
AU596400B2 (en)	1990-05-03	Carbocyclic purine nucleosides, their production and use
FI89713C (fi)	1993-11-10	Foerfarande foer framstaellning av terapeutiskt aktivt 2-(2-amino-1,6-dihydro-6-oxo-9h(purin-9-yl)metoxi)etyl-l-valinat eller l-isoleucinat eller deras salt
DK167377B1 (da)	1993-10-25	3'-azidopyrimidinnucleosider eller farmaceutisk acceptable salte eller estere deraf til anvendelse ved behandling af eller profylakse for en human retrovirusinfektion
US4957924A (en)	1990-09-18	Therapeutic valine esters of acyclovir and pharmaceutically acceptable salts thereof
FI106461B (fi)	2001-02-15	Menetelmä terapeuttisesti käyttökelpoisten enantiomeeristen yhdisteiden valmistamiseksi sekä menetelmässä käyttökelpoinen välituote
EP0357571B1 (de)	1996-04-03	Pyrimidin-Nukleoside
EP0199451B1 (de)	1996-03-06	Therapeutische Nukleoside
FI90422B (fi)	1993-10-29	Menetelmä uusien terapeuttisesti käyttökelpoisten purinyyli- ja pyrimidinyylisyklobutaanijohdannaisten valmistamiseksi
CS264290B2 (en)	1989-06-13	Process for preparing carbocyclic nucleosides of purine
JPH08501071A (ja)	1996-02-06	１，５−アンヒドロヘキシトールヌクレオシド類似体および該類似体の医薬としての使用
US8227594B2 (en)	2012-07-24	Antiviral nucleosides
JPH10507772A (ja)	1998-07-28	Ｌ−リボフラノシルヌクレオシド
EP0286425B1 (de)	1995-01-11	Therapeutische Nukleoside
EP0099493A1 (de)	1984-02-01	9-(2-Hydroxyethoxymethyl)guanin-Derivate
JPS5989682A (ja)	1984-05-23	プリン誘導体
EP0285432A2 (de)	1988-10-05	Therapeutische Nukleoside
EP0421819A1 (de)	1991-04-10	Therapeutische Nucleoside
US5061708A (en)	1991-10-29	Therapeutic guanine esters
EP0219838A2 (de)	1987-04-29	Carbocyclische Purin-Nukleoside, ihre Herstellung und Verwendung
EP0625158B1 (de)	1999-03-31	Therapeutische nukleoside der 2',3'-dideoxy-3'-fluor -purin reihe
EP0366385B1 (de)	1993-06-09	Guaninderivate mit antiviraler Wirkung und deren pharmazeutisch verträgliche Salze
JPS6222994B2 (de)	1987-05-20
EP0287215B1 (de)	1992-06-17	Therapeutische Nucleoside
EP0340778A2 (de)	1989-11-08	Prodrugs von 2',3'-Didehydro-2',3'-Dideoxynukleosiden
CA1278517C (en)	1991-01-02	Antiviral composition