JPH0326194B2 - - Google Patents

Info

Publication number: JPH0326194B2
Authority: JP; Japan
Prior art keywords: carboxamide; ribofuranosyl; selenazole; acyl; compound
Prior art date: 1982-03-23
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

JP4781383A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58213765A (ja

Inventor

Kenisu Robinsu Roorando

Chandora Suriuasutoa Puremu

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.)

Brigham Young University

Original Assignee

Brigham Young University

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.)

1982-03-23

Filing date

1983-03-22

Publication date

1991-04-10

1983-03-22 Application filed by Brigham Young University filed Critical Brigham Young University

1983-12-12 Publication of JPS58213765A publication Critical patent/JPS58213765A/ja

1991-04-10 Publication of JPH0326194B2 publication Critical patent/JPH0326194B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 38
UTYRGKYRIQSXEP-UHFFFAOYSA-N 1,3-selenazole-4-carboxamide Chemical compound NC(=O)C1=C[se]C=N1 UTYRGKYRIQSXEP-UHFFFAOYSA-N 0.000 claims description 24
125000002252 acyl group Chemical group 0.000 claims description 22
-1 R 3 is H Chemical group 0.000 claims description 14
150000003857 carboxamides Chemical class 0.000 claims description 10
229910019142 PO4 Inorganic materials 0.000 claims description 8
239000010452 phosphate Substances 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical class CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 5
NAIAADQZBCOAGC-FNCVBFRFSA-N [(2r,3s,4r,5r)-5-(4-carbamoyl-1,3-selenazol-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl acetate Chemical compound O[C@@H]1[C@H](O)[C@@H](COC(=O)C)O[C@H]1C1=NC(C(N)=O)=C[se]1 NAIAADQZBCOAGC-FNCVBFRFSA-N 0.000 claims description 4
WRHDEUYMOACEPD-FNCVBFRFSA-N [(2r,3s,4r,5r)-5-(4-carbamoyl-1,3-selenazol-2-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] acetate Chemical compound O[C@@H]1[C@H](OC(=O)C)[C@@H](CO)O[C@H]1C1=NC(C(N)=O)=C[se]1 WRHDEUYMOACEPD-FNCVBFRFSA-N 0.000 claims description 4
CXWUTSUCILFRHS-QCNRFFRDSA-N [(2r,3s,4r,5r)-5-(4-carbamoyl-1,3-selenazol-2-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] butanoate Chemical compound O[C@@H]1[C@H](OC(=O)CCC)[C@@H](CO)O[C@H]1C1=NC(C(N)=O)=C[se]1 CXWUTSUCILFRHS-QCNRFFRDSA-N 0.000 claims description 4
KEGKJQRWFNSGII-FNCVBFRFSA-N [(2r,3r,4r,5r)-2-(4-carbamoyl-1,3-selenazol-2-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1C1=NC(C(N)=O)=C[se]1 KEGKJQRWFNSGII-FNCVBFRFSA-N 0.000 claims description 3
MPCXJTZUURFVQO-QCNRFFRDSA-N [(2r,3r,4r,5r)-2-(4-carbamoyl-1,3-selenazol-2-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] butanoate Chemical compound CCCC(=O)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1C1=NC(C(N)=O)=C[se]1 MPCXJTZUURFVQO-QCNRFFRDSA-N 0.000 claims description 3
MEUDTDPOLBQTGP-QCNRFFRDSA-N [(2r,3s,4r,5r)-5-(4-carbamoyl-1,3-selenazol-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl butanoate Chemical compound O[C@@H]1[C@H](O)[C@@H](COC(=O)CCC)O[C@H]1C1=NC(C(N)=O)=C[se]1 MEUDTDPOLBQTGP-QCNRFFRDSA-N 0.000 claims description 3
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 3
239000003443 antiviral agent Substances 0.000 claims description 2
229940125904 compound 1 Drugs 0.000 description 43
239000000203 mixture Substances 0.000 description 32
241001465754 Metazoa Species 0.000 description 31
239000000047 product Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
206010028980 Neoplasm Diseases 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
229940125782 compound 2 Drugs 0.000 description 15
239000000243 solution Substances 0.000 description 15
238000012360 testing method Methods 0.000 description 14
CKMBACZHCFMPLQ-DBRKOABJSA-N 2-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-selenazole-4-carboxamide Chemical class NC(=O)C1=C[se]C([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)=N1 CKMBACZHCFMPLQ-DBRKOABJSA-N 0.000 description 13
201000011510 cancer Diseases 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000003814 drug Substances 0.000 description 12
229940079593 drug Drugs 0.000 description 12
208000006552 Lewis Lung Carcinoma Diseases 0.000 description 11
230000000840 anti-viral effect Effects 0.000 description 11
239000002904 solvent Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
238000011282 treatment Methods 0.000 description 10
239000002253 acid Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000006188 syrup Substances 0.000 description 9
235000020357 syrup Nutrition 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000002246 antineoplastic agent Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000009472 formulation Methods 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
206010027476 Metastases Diseases 0.000 description 5
241000700605 Viruses Species 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
238000004113 cell culture Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
230000004083 survival effect Effects 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
230000000259 anti-tumor effect Effects 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000006642 detritylation reaction Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000002609 medium Substances 0.000 description 4
230000009401 metastasis Effects 0.000 description 4
125000003729 nucleotide group Chemical group 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
SPVXKVOXSXTJOY-UHFFFAOYSA-N selane Chemical compound [SeH2] SPVXKVOXSXTJOY-UHFFFAOYSA-N 0.000 description 4
229910000058 selane Inorganic materials 0.000 description 4
239000000829 suppository Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000701242 Adenoviridae Species 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
239000004353 Polyethylene glycol 8000 Substances 0.000 description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
108700010877 adenoviridae proteins Proteins 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000011097 chromatography purification Methods 0.000 description 3
229940127089 cytotoxic agent Drugs 0.000 description 3
230000034994 death Effects 0.000 description 3
231100000517 death Toxicity 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 3
239000008101 lactose Substances 0.000 description 3
210000004072 lung Anatomy 0.000 description 3
239000002773 nucleotide Substances 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
235000019446 polyethylene glycol 8000 Nutrition 0.000 description 3
229940085678 polyethylene glycol 8000 Drugs 0.000 description 3
239000008213 purified water Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 3
230000003612 virological effect Effects 0.000 description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 2
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
241000450599 DNA viruses Species 0.000 description 2
208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 2
241000700586 Herpesviridae Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
241001529936 Murinae Species 0.000 description 2
241000711504 Paramyxoviridae Species 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
241000702247 Reoviridae Species 0.000 description 2
241000711931 Rhabdoviridae Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
206010070863 Toxicity to various agents Diseases 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
206010046865 Vaccinia virus infection Diseases 0.000 description 2
208000036142 Viral infection Diseases 0.000 description 2
KITFBOYQBYHZMJ-QCNRFFRDSA-N [(2r,3r,4r,5r)-2-(4-carbamoyl-1,3-selenazol-2-yl)-4-hydroxy-5-(phosphonooxymethyl)oxolan-3-yl] butanoate Chemical compound CCCC(=O)O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1C1=NC(C(N)=O)=C[se]1 KITFBOYQBYHZMJ-QCNRFFRDSA-N 0.000 description 2
GXFIQGYGJJDUOA-FDYHWXHSSA-N [(2r,3r,4r,5r)-3,4-diacetyloxy-5-(4-carbamoyl-1,3-selenazol-2-yl)oxolan-2-yl]methyl acetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1C1=NC(C(N)=O)=C[se]1 GXFIQGYGJJDUOA-FDYHWXHSSA-N 0.000 description 2
MERXIJIDHXFRDC-GWOFURMSSA-N [(2r,3r,4r,5r)-4-acetyloxy-5-(4-carbamoyl-1,3-selenazol-2-yl)-2-(phosphonooxymethyl)oxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@@H](COP(O)(O)=O)O[C@H]1C1=NC(C(N)=O)=C[se]1 MERXIJIDHXFRDC-GWOFURMSSA-N 0.000 description 2
HXPXOJBOAOKEIA-JUDXGUMMSA-N [(2r,3r,4r,5r)-4-butanoyloxy-5-(4-carbamoyl-1,3-selenazol-2-yl)-2-(phosphonooxymethyl)oxolan-3-yl] butanoate Chemical compound CCCC(=O)O[C@@H]1[C@H](OC(=O)CCC)[C@@H](COP(O)(O)=O)O[C@H]1C1=NC(C(N)=O)=C[se]1 HXPXOJBOAOKEIA-JUDXGUMMSA-N 0.000 description 2
GCUIHRUSZMITGH-FDYHWXHSSA-N [(2r,3s,4r,5r)-5-(4-carbamoyl-1,3-selenazol-2-yl)-4-hydroxy-2-(phosphonooxymethyl)oxolan-3-yl] benzoate Chemical compound NC(=O)C1=C[se]C([C@H]2[C@@H]([C@H](OC(=O)C=3C=CC=CC=3)[C@@H](COP(O)(O)=O)O2)O)=N1 GCUIHRUSZMITGH-FDYHWXHSSA-N 0.000 description 2
HLUGQLYIPXETOU-QCNRFFRDSA-N [(2r,3s,4r,5r)-5-(4-carbamoyl-1,3-selenazol-2-yl)-4-hydroxy-2-(phosphonooxymethyl)oxolan-3-yl] butanoate Chemical compound O[C@@H]1[C@H](OC(=O)CCC)[C@@H](COP(O)(O)=O)O[C@H]1C1=NC(C(N)=O)=C[se]1 HLUGQLYIPXETOU-QCNRFFRDSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
238000005915 ammonolysis reaction Methods 0.000 description 2
159000000032 aromatic acids Chemical class 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
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GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
239000012351 deprotecting agent Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
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KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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230000003211 malignant effect Effects 0.000 description 2
206010061289 metastatic neoplasm Diseases 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
230000000865 phosphorylative effect Effects 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000005855 radiation Effects 0.000 description 2
238000001959 radiotherapy Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000012216 screening Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 2
208000007089 vaccinia Diseases 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
230000009385 viral infection Effects 0.000 description 2
239000008215 water for injection Substances 0.000 description 2
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125000002221 trityl group Chemical group [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
238000005866 tritylation reaction Methods 0.000 description 1
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230000003253 viricidal effect Effects 0.000 description 1
230000001790 virustatic effect Effects 0.000 description 1

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Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)

JP4781383A 1982-03-23 1983-03-22 新規な２−β−Ｄ−リボフラノシルセレナゾ−ル−４−カルボキサミド化合物およびそれらの製造方法 Granted JPS58213765A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US36096882A	1982-03-23	1982-03-23
US360968		1982-03-23
US465221		1983-02-15

Publications (2)

Publication Number	Publication Date
JPS58213765A JPS58213765A (ja)	1983-12-12
JPH0326194B2 true JPH0326194B2 (da)	1991-04-10

Family

ID=23420119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4781383A Granted JPS58213765A (ja)	1982-03-23	1983-03-22	新規な２−β−Ｄ−リボフラノシルセレナゾ−ル−４−カルボキサミド化合物およびそれらの製造方法

Country Status (2)

Country	Link
JP (1)	JPS58213765A (da)
ZA (1)	ZA832003B (da)

1983
- 1983-03-22 ZA ZA832003A patent/ZA832003B/xx unknown
- 1983-03-22 JP JP4781383A patent/JPS58213765A/ja active Granted

Also Published As

Publication number	Publication date
ZA832003B (en)	1983-11-30
JPS58213765A (ja)	1983-12-12

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