CA1230876A - Derives de thiodeazapurine - Google Patents

Derives de thiodeazapurine

Info

Publication number: CA1230876A
Authority: CA; Canada
Prior art keywords: group; compound; carbon atoms; formula; alpha
Prior art date: 1983-03-17
Legal status (The legal status 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 status listed.): Expired

Application number

CA000519122A

Other languages

English (en)

Inventor

Susumu Nishimura

Hiroaki Nomura

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

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.)

1983-03-17

Filing date

1986-09-25

Publication date

1987-12-29

1983-03-17 Priority claimed from JP58045725A external-priority patent/JPS59170091A/ja

1984-02-10 Priority claimed from JP2353984A external-priority patent/JPS60166682A/ja

1984-03-16 Priority claimed from CA000449759A external-priority patent/CA1233464A/fr

1986-09-25 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1986-09-25 Priority to CA000519122A priority Critical patent/CA1230876A/fr

1987-12-29 Application granted granted Critical

1987-12-29 Publication of CA1230876A publication Critical patent/CA1230876A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 88
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 18
125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
125000004122 cyclic group Chemical group 0.000 claims abstract description 14
125000003277 amino group Chemical group 0.000 claims abstract description 12
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
125000002252 acyl group Chemical group 0.000 claims abstract description 7
150000001412 amines Chemical class 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 6
125000000217 alkyl group Chemical group 0.000 claims abstract 5
238000006683 Mannich reaction Methods 0.000 claims abstract 3
-1 n-octanoyl Chemical group 0.000 claims description 51
150000003839 salts Chemical class 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000002905 alkanoylamido group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
125000003435 aroyl group Chemical group 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
239000002246 antineoplastic agent Substances 0.000 abstract description 3
239000000645 desinfectant Substances 0.000 abstract description 3
230000003641 microbiacidal effect Effects 0.000 abstract description 2
229940124561 microbicide Drugs 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
229920000180 alkyd Polymers 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 10
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WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 7
239000000243 solution Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
MGAXHFMCFLLMNG-UHFFFAOYSA-N 1h-pyrimidine-6-thione Chemical compound SC1=CC=NC=N1 MGAXHFMCFLLMNG-UHFFFAOYSA-N 0.000 description 5
241000208422 Rhododendron Species 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
230000008030 elimination Effects 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
229960004279 formaldehyde Drugs 0.000 description 4
235000019256 formaldehyde Nutrition 0.000 description 4
125000001183 hydrocarbyl group Chemical group 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
WYROLENTHWJFLR-ACLDMZEESA-N queuine Chemical compound C1=2C(=O)NC(N)=NC=2NC=C1CN[C@H]1C=C[C@H](O)[C@@H]1O WYROLENTHWJFLR-ACLDMZEESA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
241000282320 Panthera leo Species 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
108020004566 Transfer RNA Proteins 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
229910001863 barium hydroxide Inorganic materials 0.000 description 3
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
239000004327 boric acid Substances 0.000 description 3
125000000392 cycloalkenyl group Chemical group 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
239000000499 gel Substances 0.000 description 3
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
238000000746 purification Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
108020005098 Anticodon Proteins 0.000 description 2
240000002132 Beaucarnea recurvata Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
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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
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
240000002989 Euphorbia neriifolia Species 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
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241000699666 Mus <mouse, genus> Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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241000700159 Rattus Species 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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125000003545 alkoxy group Chemical group 0.000 description 2
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230000000259 anti-tumor effect Effects 0.000 description 2
238000003556 assay Methods 0.000 description 2
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ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 2
230000002950 deficient Effects 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
230000012010 growth Effects 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
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238000006460 hydrolysis reaction Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
238000002955 isolation Methods 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 2
229940102396 methyl bromide Drugs 0.000 description 2
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000002265 prevention Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
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239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
SMOWDHJUHLOVAM-UHFFFAOYSA-N tert-butyl 2-[(2-amino-6-methyl-4-sulfanylidenepyrrolo[2,3-d]pyrimidin-5-yl)amino]acetate Chemical compound NC1=NC(=S)C2=C(NCC(=O)OC(C)(C)C)C(C)=NC2=N1 SMOWDHJUHLOVAM-UHFFFAOYSA-N 0.000 description 1
125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
238000007280 thionation reaction Methods 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000014616 translation Effects 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000519122A 1983-03-17 1986-09-25 Derives de thiodeazapurine Expired CA1230876A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000519122A CA1230876A (fr)	1983-03-17	1986-09-25	Derives de thiodeazapurine

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP45725/1983		1983-03-17
JP58045725A JPS59170091A (ja)	1983-03-17	1983-03-17	６−チオ−７−デアザプリン誘導体およびその製造法
JP23539/1984		1984-02-10
JP2353984A JPS60166682A (ja)	1984-02-10	1984-02-10	７−デアザプリン誘導体およびその製造法
CA000449759A CA1233464A (fr)	1983-03-17	1984-03-16	Derives de thiodeazapurine
CA000519122A CA1230876A (fr)	1983-03-17	1986-09-25	Derives de thiodeazapurine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000449759A Division CA1233464A (fr)	1983-03-17	1984-03-16	Derives de thiodeazapurine

Publications (1)

Publication Number	Publication Date
CA1230876A true CA1230876A (fr)	1987-12-29

Family

ID=27167427

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000519122A Expired CA1230876A (fr)	1983-03-17	1986-09-25	Derives de thiodeazapurine

Country Status (1)

Country	Link
CA (1)	CA1230876A (fr)

1986
- 1986-09-25 CA CA000519122A patent/CA1230876A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-12-29	MKEX	Expiry

Publication	Publication Date	Title
US7662809B2 (en)	2010-02-16	Tetracyclic indole derivatives as antiviral agents
US4323570A (en)	1982-04-06	Substituted aminopyrimidines
CA2621841A1 (fr)	2007-03-15	Derives d'indole tetracycliques utilises comme agents antiviraux
JPS62142178A (ja)	1987-06-25	キシロフラノシルプリンの抗ウイルス性炭素環式類似体
Montgomery et al.	1966	Further Studies on the Alkylation of Purines1
GB2121796A (en)	1984-01-04	Amidines
US4571423A (en)	1986-02-18	Substituted 5-aminomethyl-2-acylaminopyrrolo[2,3-d]pyrimidin-4-ones
CA1224460A (fr)	1987-07-21	.beta.-GLYCOSYL C-NUCLEOSIDES ANTI-LEUCEMIQUES
US7795247B2 (en)	2010-09-14	Tetracyclic indole derivatives as antiviral agents
EP0119591B1 (fr)	1988-06-22	Dérivés de la thiodeazapurine
CA1230876A (fr)	1987-12-29	Derives de thiodeazapurine
US4595530A (en)	1986-06-17	Thiodeazapurine derivatives
CZ299816B6 (cs)	2008-12-03	Isonitrilové slouceniny pro výrobu polymeru, které obsahují nukleové báze jako postranní skupiny
CA1233464A (fr)	1988-03-01	Derives de thiodeazapurine
JPH0417195B2 (fr)	1992-03-25
US4617389A (en)	1986-10-14	Mitomycin analogs
CA2463507A1 (fr)	2003-04-17	Methodes de synthese de purines substituees
US4650868A (en)	1987-03-17	7-deazapurine derivatives useful as antitumor agents
US4587052A (en)	1986-05-06	1H-pyrrolo-[2,1-C][1,4]benzodiazepine-2-acrylamide compounds having antitumor activity
JPH0438757B2 (fr)	1992-06-25
US4049812A (en)	1977-09-20	Benzodiazepine carboxamides and pharmaceutical compositions with central nervous system activity
Alves et al.	1999	Synthesis and mechanism of formation of novel 2, 5‐dihydro‐2, 5‐diimino‐3, 4‐di [(N, N‐dimethylamino) methylideneamino] pyrroles and 5‐amino‐3, 4‐di [(N, N‐dimethylamino) methylideneamino]‐2H‐2‐iminopyrroles
FI94344C (fi)	1995-08-25	Menetelmä uusien terapeuttisesti käyttökelpoisten triatsolopyrimidiinijohdannaisten valmistamiseksi
Itaya et al.	1996	Purines. LXXI. Preparation and alkylation of 7-alkyladenine 1-oxides: A general synthesis of 1-alkoxy-7-alkyladenines
KR850000262B1 (ko)	1985-03-14	벤즈 아체핀 유도체의 제조방법