IL47338A - Acylated derivatives of pyrazofurin and process for their preparation - Google Patents

Acylated derivatives of pyrazofurin and process for their preparation

Info

Publication number: IL47338A
Authority: IL; Israel
Prior art keywords: alkanoyl; hydroxy; tri; carboxamide; compound
Prior art date: 1974-07-22

Application number

IL47338A

Other languages

English (en)

Other versions

IL47338A0 (en

Original Assignee

Lilly Co Eli

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.)

1974-07-22

Filing date

1975-05-22

Publication date

1977-11-30

1975-05-22 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1975-07-28 Publication of IL47338A0 publication Critical patent/IL47338A0/xx

1977-11-30 Publication of IL47338A publication Critical patent/IL47338A/en

Links

XESARGFCSKSFID-FLLFQEBCSA-N pirazofurin Chemical class OC1=C(C(=O)N)NN=C1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 XESARGFCSKSFID-FLLFQEBCSA-N 0.000 title claims description 77
238000000034 method Methods 0.000 title claims description 35
238000002360 preparation method Methods 0.000 title claims description 12
XESARGFCSKSFID-UHFFFAOYSA-N Pyrazofurin Natural products OC1=C(C(=O)N)NN=C1C1C(O)C(O)C(CO)O1 XESARGFCSKSFID-UHFFFAOYSA-N 0.000 claims description 63
239000003795 chemical substances by application Substances 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 40
238000005917 acylation reaction Methods 0.000 claims description 30
239000000243 solution Substances 0.000 claims description 30
125000001589 carboacyl group Chemical group 0.000 claims description 28
230000010933 acylation Effects 0.000 claims description 22
125000002252 acyl group Chemical group 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 14
-1 butyrylribofuranosyl Chemical group 0.000 claims description 13
BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
238000003797 solvolysis reaction Methods 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
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 claims description 5
239000002775 capsule Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
239000002674 ointment Substances 0.000 claims description 3
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 2
239000000470 constituent Substances 0.000 claims description 2
239000006071 cream Substances 0.000 claims description 2
238000007911 parenteral administration Methods 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
125000003843 furanosyl group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000003826 tablet Substances 0.000 claims 1
CXBMCYHAMVGWJQ-UHFFFAOYSA-N tetramethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-UHFFFAOYSA-N 0.000 claims 1
238000011200 topical administration Methods 0.000 claims 1
239000002904 solvent Substances 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000002585 base Substances 0.000 description 41
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 16
239000000047 product Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000003586 protic polar solvent Substances 0.000 description 11
150000008065 acid anhydrides Chemical class 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000000746 purification Methods 0.000 description 9
101150041968 CDC13 gene Proteins 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 8
239000003085 diluting agent Substances 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
238000003756 stirring Methods 0.000 description 7
229940086542 triethylamine Drugs 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 6
150000004820 halides Chemical class 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
230000000259 anti-tumor effect Effects 0.000 description 5
239000002777 nucleoside Substances 0.000 description 5
125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 5
229960001407 sodium bicarbonate Drugs 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002246 antineoplastic agent Substances 0.000 description 4
239000006184 cosolvent Substances 0.000 description 4
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 4
239000010410 layer Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WYXSYVWAUAUWLD-SHUUEZRQSA-N 6-azauridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=N1 WYXSYVWAUAUWLD-SHUUEZRQSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
201000004681 Psoriasis Diseases 0.000 description 3
241000700605 Viruses Species 0.000 description 3
230000002682 anti-psoriatic effect Effects 0.000 description 3
230000000840 anti-viral effect Effects 0.000 description 3
239000003443 antiviral agent Substances 0.000 description 3
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000003226 pyrazolyl group Chemical group 0.000 description 3
239000007787 solid Substances 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-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
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QQOBRRFOVWGIMD-OJAKKHQRSA-N azaribine Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1N1C(=O)NC(=O)C=N1 QQOBRRFOVWGIMD-OJAKKHQRSA-N 0.000 description 2
229950010054 azaribine Drugs 0.000 description 2
FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 2
230000036765 blood level Effects 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
150000002561 ketenes Chemical class 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003791 organic solvent mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FGQLGYBGTRHODR-UHFFFAOYSA-N 2,2-diethoxypropane Chemical compound CCOC(C)(C)OCC FGQLGYBGTRHODR-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
OXCVCJVUOYADBS-UHFFFAOYSA-N 3-methylbut-1-en-1-one Chemical compound CC(C)C=C=O OXCVCJVUOYADBS-UHFFFAOYSA-N 0.000 description 1
OGMHLZVDKIJTMN-UHFFFAOYSA-N 3-methylpentanoyl chloride Chemical compound CCC(C)CC(Cl)=O OGMHLZVDKIJTMN-UHFFFAOYSA-N 0.000 description 1
QZRQTSIXJZDADO-UHFFFAOYSA-N 4-methylpent-1-en-1-one Chemical compound CC(C)CC=C=O QZRQTSIXJZDADO-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010000830 Acute leukaemia Diseases 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
241000709661 Enterovirus Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
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 1
239000004166 Lanolin Substances 0.000 description 1
OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 description 1
241000283956 Manis Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
201000005505 Measles Diseases 0.000 description 1
241000712079 Measles morbillivirus Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000700584 Simplexvirus Species 0.000 description 1
241000958233 Streptomyces candidus Species 0.000 description 1
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 1
229930006000 Sucrose Natural products 0.000 description 1
241000700618 Vaccinia virus Species 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
NGXUUAFYUCOICP-UHFFFAOYSA-N aminometradine Chemical group CCN1C(=O)C=C(N)N(CC=C)C1=O NGXUUAFYUCOICP-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
JSEMCPMTAXQTJN-UHFFFAOYSA-N but-1-en-1-one Chemical compound CCC=C=O JSEMCPMTAXQTJN-UHFFFAOYSA-N 0.000 description 1
QAWBXZYPFCFQLA-UHFFFAOYSA-N butanoyl bromide Chemical compound CCCC(Br)=O QAWBXZYPFCFQLA-UHFFFAOYSA-N 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000005676 cyclic carbonates Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
238000011161 development Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940116333 ethyl lactate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000003827 glycol group Chemical group 0.000 description 1
ZMFNQNZKRXIAGJ-UHFFFAOYSA-N hex-1-en-1-one Chemical compound CCCCC=C=O ZMFNQNZKRXIAGJ-UHFFFAOYSA-N 0.000 description 1
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
244000000056 intracellular parasite Species 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
230000007775 late Effects 0.000 description 1
OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 description 1
229960005287 lincomycin Drugs 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
208000010555 moderate anemia Diseases 0.000 description 1
GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
CSIJVUYEABVULE-UHFFFAOYSA-N pent-1-en-1-one Chemical compound CCCC=C=O CSIJVUYEABVULE-UHFFFAOYSA-N 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
231100000057 systemic toxicity Toxicity 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

IL47338A 1974-07-22 1975-05-22 Acylated derivatives of pyrazofurin and process for their preparation IL47338A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/490,627 US3960836A (en)	1974-07-22	1974-07-22	Acylated derivatives of pyrazofurin and process for their preparation

Publications (2)

Publication Number	Publication Date
IL47338A0 IL47338A0 (en)	1975-07-28
IL47338A true IL47338A (en)	1977-11-30

Family

ID=23948851

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL47338A IL47338A (en)	1974-07-22	1975-05-22	Acylated derivatives of pyrazofurin and process for their preparation

Country Status (10)

Country	Link
US (1)	US3960836A (fr)
JP (1)	JPS5116665A (fr)
BE (1)	BE831568A (fr)
CA (1)	CA1041493A (fr)
DE (1)	DE2532069A1 (fr)
FR (1)	FR2279410A1 (fr)
GB (1)	GB1516174A (fr)
IE (1)	IE41067B1 (fr)
IL (1)	IL47338A (fr)
NL (1)	NL7508706A (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PH15570A (en) *	1976-05-14	1983-02-17	Upjohn Co	Pyrazole amides and thioamides
DK553781A (da) *	1980-12-15	1982-06-16	Vira Tek Inc	Fremgangsmaade til fremstilling af 2-beta-d-ribofuranosulthiazol-4-carboxid-estere
US5102883A (en) *	1989-10-31	1992-04-07	Du Pont Merck Pharmaceutical Company	Pyrimidine biosynthesis inhibitors useful as immunosuppressive agents
JPH0649650B2 (ja) *	1990-05-17	1994-06-29	旭化成工業株式会社	４―カルバモイル―１―β―Ｄ―リボフラノシル―イミダゾリウム―５―オレイトを有効成分とする用途
GB9307043D0 (en) *	1993-04-05	1993-05-26	Norsk Hydro As	Chemical compounds
GB0016787D0 (en)	2000-07-07	2000-08-30	Pfizer Ltd	Compounds useful in therapy
WO2004084796A2 (fr) *	2003-03-28	2004-10-07	Pharmasset Ltd.	Composes permettant de traiter les infections par flavivirus
CN106588891A (zh) *	2016-10-26	2017-04-26	郑州大学	一种吡唑呋喃菌素的c‑核苷类似物及其合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3674774A (en) *	1969-04-23	1972-07-04	Lilly Co Eli	Pyrazomycin and process for production thereof
US3798209A (en) *	1971-06-01	1974-03-19	Icn Pharmaceuticals	1,2,4-triazole nucleosides

1974
- 1974-07-22 US US05/490,627 patent/US3960836A/en not_active Expired - Lifetime
1975
- 1975-05-15 CA CA227,019A patent/CA1041493A/fr not_active Expired
- 1975-05-16 IE IE1108/75A patent/IE41067B1/xx unknown
- 1975-05-22 IL IL47338A patent/IL47338A/en unknown
- 1975-06-09 JP JP50069461A patent/JPS5116665A/ja active Pending
- 1975-07-15 GB GB29531/75A patent/GB1516174A/en not_active Expired
- 1975-07-17 DE DE19752532069 patent/DE2532069A1/de not_active Withdrawn
- 1975-07-18 FR FR7522550A patent/FR2279410A1/fr not_active Withdrawn
- 1975-07-21 NL NL7508706A patent/NL7508706A/xx not_active Application Discontinuation
- 1975-07-22 BE BE1006793A patent/BE831568A/fr unknown

Also Published As

Publication number	Publication date
US3960836A (en)	1976-06-01
NL7508706A (nl)	1976-01-26
CA1041493A (fr)	1978-10-31
FR2279410A1 (fr)	1976-02-20
GB1516174A (en)	1978-06-28
BE831568A (fr)	1976-01-22
IE41067L (en)	1976-01-22
IE41067B1 (en)	1979-10-10
JPS5116665A (en)	1976-02-10
IL47338A0 (en)	1975-07-28
DE2532069A1 (de)	1976-02-05

Publication	Publication Date	Title
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EP0260979B1 (fr)	1991-05-15	Dérivés du sucrose
US5283327A (en)	1994-02-01	Tri-O-acetyl-2-alkynyladenosines
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Lemieux et al.	1956	The Preparation and Properties of α-D-Glucopyranose 1, 2-(Ethyl Orthoacetate) Triacetate
Tsuji et al.	1978	Trichostatin C, a glucopyranosyl hydroxamate
Baker et al.	1957	Synthesis of Potential Anticancer Agents. VIII. 2Nucleosides Derived from L-Rhamnofuranose
Schaumberg et al.	1985	2'-Chloropentostatin, a new inhibitor of adenosine deaminase
US3960836A (en)	1976-06-01	Acylated derivatives of pyrazofurin and process for their preparation
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Pravdic et al.	1967	The formation of acetylated oxazolines through the action of zinc chloride and acetic anhydride on 2-acylamino-2-deoxyaldoses
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GB2055812A (en)	1981-03-11	Method of preparation of esters of antibiotics from the group of polyene macrolides and of n-substituted derivatives thereof
CA1320951C (fr)	1993-08-03	Derives de la disaccharide
EP0789028B1 (fr)	2002-05-02	Procédé pour la glycosidation de dérivés de colchicine et produits obtenus
US4053698A (en)	1977-10-11	Acylation of pyrazofurin
MORI et al.	1974	Thiosugars. XVII. Syntheses of Maltose Derivatives having Sulfur Atom in the Reducing Moiety
Kiss et al.	1976	Synthesis of heparin saccharides—V: Anomeric o-benzyl derivatives of l-idopyranosyluronic acid
Glaudemans et al.	1964	Synthesis of the Two 2-O-Nitro-3, 5-di-Op-nitrobenzoyl-D-arabinofuranosyl Chlorides, an Anomeric Pair of Crystalline Pentofuranosyl Halides Having a Nonparticipating Group at C-2
US4764605A (en)	1988-08-16	Process for selectively deacetylating acetyl derivatives of saccharides
US3950324A (en)	1976-04-13	D-glucose-1-0-nicotinoyl-2-deoxy-2-nictinamido derivatives
Backinowsky et al.	1981	Reactions of sugar thio-orthoesters: Nucleophilic substitution of an arylthio group during zemplén deacylation
Tsuchiya et al.	1970	Studies on Aminosugars. XXIV. The Facile Elimination of the Derivatives of a Pyranosid-4-ulose
Rosenthal et al.	1980	Synthesis of an analog of the nucleoside moiety of the polyoxins