CA1233464A - Derives de thiodeazapurine - Google Patents

Derives de thiodeazapurine

Info

Publication number: CA1233464A
Authority: CA; Canada
Prior art keywords: group; carbon atoms; amino; formula; thione
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

CA000449759A

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

1984-03-16

Publication date

1988-03-01

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 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

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

1988-03-01 Application granted granted Critical

1988-03-01 Publication of CA1233464A publication Critical patent/CA1233464A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 89
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
125000002252 acyl group Chemical group 0.000 claims abstract description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
125000001424 substituent group Chemical group 0.000 claims abstract description 20
125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 18
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 17
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
125000004122 cyclic group Chemical group 0.000 claims abstract description 15
125000003277 amino group Chemical group 0.000 claims abstract description 13
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
125000004432 carbon atom Chemical group C* 0.000 claims description 63
-1 di-carboxymethyl-substituted amino Chemical group 0.000 claims description 52
150000003839 salts Chemical class 0.000 claims description 48
238000000034 method Methods 0.000 claims description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
239000000047 product Substances 0.000 claims description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
238000006467 substitution reaction Methods 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
238000007792 addition Methods 0.000 claims description 13
125000003710 aryl alkyl group Chemical group 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
MGAXHFMCFLLMNG-UHFFFAOYSA-N 1h-pyrimidine-6-thione Chemical compound SC1=CC=NC=N1 MGAXHFMCFLLMNG-UHFFFAOYSA-N 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
239000007795 chemical reaction product Substances 0.000 claims description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
238000006683 Mannich reaction Methods 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
125000003435 aroyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
HHIDBQCPVZHDOM-UHFFFAOYSA-N 2-amino-5-(aminomethyl)pyrrolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CC(CN)=C2C1=NC(N)=NC2=S HHIDBQCPVZHDOM-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000002905 alkanoylamido group Chemical group 0.000 claims description 3
238000005947 deacylation reaction Methods 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 3
HTDPDLVWFWOIBZ-UHFFFAOYSA-N 1,7-dihydropyrrolo[2,3-d]pyrimidine-4-thione Chemical compound SC1=NC=NC2=C1C=CN2 HTDPDLVWFWOIBZ-UHFFFAOYSA-N 0.000 claims description 2
CHWLZAYUZFDJLF-UHFFFAOYSA-N 2-amino-5-(piperidin-1-ylmethyl)pyrrolo[2,3-d]pyrimidine-4-thione Chemical compound C1=NC2=NC(N)=NC(=S)C2=C1CN1CCCCC1 CHWLZAYUZFDJLF-UHFFFAOYSA-N 0.000 claims description 2
KTULDXXGBNXMRA-UHFFFAOYSA-N 2-amino-5-[(3-methylbutylamino)methyl]pyrrolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CC(CNCCC(C)C)=C2C1=NC(N)=NC2=S KTULDXXGBNXMRA-UHFFFAOYSA-N 0.000 claims description 2
MLVFWLMLLUZNSD-UHFFFAOYSA-N 2-amino-5-[[2-(2-hydroxyethoxy)ethylamino]methyl]pyrrolo[2,3-d]pyrimidine-4-thione Chemical compound NC1=NC(=S)C2=C(CNCCOCCO)C=NC2=N1 MLVFWLMLLUZNSD-UHFFFAOYSA-N 0.000 claims description 2
OJFZLBZJMQCWFP-UHFFFAOYSA-N 4-(piperidin-1-ylmethyl)isoindole-1,3-dione Chemical compound O=C1NC(=O)C2=C1C=CC=C2CN1CCCCC1 OJFZLBZJMQCWFP-UHFFFAOYSA-N 0.000 claims description 2
229930040373 Paraformaldehyde Natural products 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000002393 azetidinyl group Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
239000004312 hexamethylene tetramine Substances 0.000 claims description 2
235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
125000002636 imidazolinyl group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
229920002866 paraformaldehyde Polymers 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 13
239000001257 hydrogen Substances 0.000 claims 13
239000012458 free base Substances 0.000 claims 3
KPRZOPQOBJRYSW-UHFFFAOYSA-N 2-(aminomethyl)phenol Chemical compound NCC1=CC=CC=C1O KPRZOPQOBJRYSW-UHFFFAOYSA-N 0.000 claims 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 2
125000001485 cycloalkadienyl group Chemical group 0.000 claims 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 2
125000003884 phenylalkyl group Chemical group 0.000 claims 2
GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims 1
PTTQLCQHTYSXBH-UHFFFAOYSA-N 2-amino-5-[(2-hydroxyanilino)methyl]pyrrolo[2,3-d]pyrimidine-4-thione Chemical compound C1=NC2=NC(N)=NC(=S)C2=C1CNC1=CC=CC=C1O PTTQLCQHTYSXBH-UHFFFAOYSA-N 0.000 claims 1
OYIMVVOJCJHPPI-UHFFFAOYSA-N 2-amino-5-[(cyclopentylamino)methyl]pyrrolo[2,3-d]pyrimidine-4-thione Chemical compound C1=NC2=NC(N)=NC(=S)C2=C1CNC1CCCC1 OYIMVVOJCJHPPI-UHFFFAOYSA-N 0.000 claims 1
IREISFRGUURFQA-UHFFFAOYSA-N 2-amino-5-[[(2-hydroxyphenyl)methylamino]methyl]pyrrolo[2,3-d]pyrimidine-4-thione Chemical compound C1=NC2=NC(N)=NC(=S)C2=C1CNCC1=CC=CC=C1O IREISFRGUURFQA-UHFFFAOYSA-N 0.000 claims 1
ZXJLDZPXGKGPPX-ACLDMZEESA-N 2-amino-5-[[[(1s,4s,5r)-4,5-dihydroxycyclopent-2-en-1-yl]amino]methyl]pyrrolo[2,3-d]pyrimidine-4-thione Chemical compound C1=NC2=NC(N)=NC(=S)C2=C1CN[C@H]1C=C[C@H](O)[C@@H]1O ZXJLDZPXGKGPPX-ACLDMZEESA-N 0.000 claims 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
239000002798 polar solvent 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
239000002855 microbicide agent Substances 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
108020004566 Transfer RNA Proteins 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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 11
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
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
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
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-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
239000007864 aqueous solution Substances 0.000 description 4
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 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
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
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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
201000011510 cancer Diseases 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
238000001914 filtration Methods 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
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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
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SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
229930027917 kanamycin Natural products 0.000 description 1
229960000318 kanamycin Drugs 0.000 description 1
229930182823 kanamycin A Natural products 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
125000000628 margaroyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108020004999 messenger RNA Proteins 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000001419 myristoyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
YKLILOQNYBYBIC-UHFFFAOYSA-N n-(4-sulfanylidenepyrrolo[2,3-d]pyrimidin-2-yl)octanamide Chemical compound CCCCCCCC(=O)NC1=NC(=S)C2=CC=NC2=N1 YKLILOQNYBYBIC-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
125000001402 nonanoyl 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])[H] 0.000 description 1
REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001312 palmitoyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
229960002816 potassium chloride Drugs 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
102000005499 queuine tRNA-ribosyltransferase Human genes 0.000 description 1
108010061997 queuine tRNA-ribosyltransferase Proteins 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000003696 stearoyl 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])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
125000004079 stearyl 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])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
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000004149 thio group Chemical group *S* 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
238000002054 transplantation Methods 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
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013311 vegetables Nutrition 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)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA000449759A 1983-03-17 1984-03-16 Derives de thiodeazapurine Expired CA1233464A (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 (4)

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

Related Child Applications (1)

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

Publications (1)

Publication Number	Publication Date
CA1233464A true CA1233464A (fr)	1988-03-01

Family

ID=26360912

Family Applications (1)

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

Country Status (1)

Country	Link
CA (1)	CA1233464A (fr)

1984
- 1984-03-16 CA CA000449759A patent/CA1233464A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-03-01	MKEX	Expiry

Publication	Publication Date	Title
US4323570A (en)	1982-04-06	Substituted aminopyrimidines
US5496946A (en)	1996-03-05	Production of pyrrolopyrimidines and intermediates therefor
NZ204352A (en)	1987-07-31	Mitomycin analogs carrying one or more guanidino substituents in the 7- and/or 10-positions
CA1181399A (fr)	1985-01-22	Derives de deazapurine
JPH0249313B2 (fr)	1990-10-29
US4595530A (en)	1986-06-17	Thiodeazapurine derivatives
CA1233464A (fr)	1988-03-01	Derives de thiodeazapurine
EP0119591B1 (fr)	1988-06-22	Dérivés de la thiodeazapurine
Komkov et al.	1995	5-Acetyl-6-amino-4-methylthio-2-phenylpyrimidine and its use in the synthesis of functionalized pyrido [2, 3-d] pyrimidines and pyrimido-[4, 5-d] pyrimidines
FR2461705A1 (fr)	1981-02-06	Nouveaux derives de 1-(4-aminobenzyl)-2,3-dioxopiperazine et leurs sels d'addition d'acides, a action carcinostatique, et procedes pour les preparer
JPH0417195B2 (fr)	1992-03-25
CA1230876A (fr)	1987-12-29	Derives de thiodeazapurine
Salimov et al.	2005	Synthesis and Antimicrobial Activity of 2-Bromo-7-methyl-5-oxo-5H-1, 3, 4-thiadiazolo [3, 2-a] pyrimidine
US2963480A (en)	1960-12-06	6-pteridinehydrazine and amidrazone derivatives
US3505331A (en)	1970-04-07	Process for preparing 2,4-diamino-7-chloropyrido(2,3-d)pyrimidines
US3320256A (en)	1967-05-16	Fluorinated imidazoo[1, 2-c]pyrimidines and pyrimido[1, 2-c]pyrimidines
US4650868A (en)	1987-03-17	7-deazapurine derivatives useful as antitumor agents
Shutske et al.	1993	Synthesis of Some amino‐4, 5‐dihydropyrazolo [3, 4‐a] acridines as potential cholinesterase inhibitors
JP3376479B2 (ja)	2003-02-10	縮合ピリミジン誘導体、その製造法および用途
JPH0438757B2 (fr)	1992-06-25
US4587052A (en)	1986-05-06	1H-pyrrolo-[2,1-C][1,4]benzodiazepine-2-acrylamide compounds having antitumor activity
EP0431953A2 (fr)	1991-06-12	Dérivés de pyrrolopyrimidine, leur préparation et utilisation
Swistun et al.	1981	On the reaction of 5‐aminopyrimidine with diazonium salts
GB1596376A (en)	1981-08-26	4,5-disubstituted imidazole-2-thiones processes for their preparation and their use as intermediates
CA1117535A (fr)	1982-02-02	Anthracene-9,10-bis-carbonyl-hydrazones