CA1055012A - Derivatives of desglucohellebrin and a process for their production - Google Patents

Derivatives of desglucohellebrin and a process for their production

Info

Publication number: CA1055012A
Authority: CA; Canada
Prior art keywords: beta; oxo; bufa; dienolide; dihydroxy
Prior art date: 1974-01-15
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

CA223,815A

Other languages

English (en)

French (fr)

Other versions

CA223815S (en

Inventor

Otto Isaac

Horst Uthemann

Klaus Posselt

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.)

Evonik Operations GmbH

Original Assignee

Deutsche Gold und Silber Scheideanstalt

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.)

1974-01-15

Filing date

1975-04-03

Publication date

1979-05-22

1974-01-15 Priority claimed from AT30174A external-priority patent/AT325954B/de

1974-04-03 Priority claimed from AT279574A external-priority patent/AT331423B/de

1975-04-03 Application filed by Deutsche Gold und Silber Scheideanstalt filed Critical Deutsche Gold und Silber Scheideanstalt

1979-05-22 Application granted granted Critical

1979-05-22 Publication of CA1055012A publication Critical patent/CA1055012A/en

Status Expired legal-status Critical Current

Links

HNNFRQFXBWSJBX-UHFFFAOYSA-N 5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde Chemical class OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C5=COC(=O)C=C5)C4(C)CCC3C2(C=O)CC1 HNNFRQFXBWSJBX-UHFFFAOYSA-N 0.000 title claims abstract description 38
238000000034 method Methods 0.000 title claims description 25
238000004519 manufacturing process Methods 0.000 title description 4
-1 alkyl radical Chemical class 0.000 claims abstract description 41
150000001875 compounds Chemical class 0.000 claims abstract description 33
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
150000003254 radicals Chemical class 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims abstract description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract description 4
125000002252 acyl group Chemical group 0.000 claims abstract 3
CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims abstract 3
239000000126 substance Substances 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 14
239000000047 product Substances 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 5
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
ZUMISMXLQDKQDS-QPJJXVBHSA-N (e)-1,1-diethoxybut-2-ene Chemical compound CCOC(OCC)\C=C\C ZUMISMXLQDKQDS-QPJJXVBHSA-N 0.000 claims description 3
LGICWIVABSMSDK-UHFFFAOYSA-N 1,1,3-triethoxypropane Chemical compound CCOCCC(OCC)OCC LGICWIVABSMSDK-UHFFFAOYSA-N 0.000 claims description 3
OMAKZNALRADTRX-UHFFFAOYSA-N 1,1,3-trimethoxybutane Chemical compound COC(C)CC(OC)OC OMAKZNALRADTRX-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
SXDCKSSXFPOLRX-UHFFFAOYSA-N 3,3-dimethoxybutanal Chemical compound COC(C)(OC)CC=O SXDCKSSXFPOLRX-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
230000001534 intropic effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
239000000741 silica gel Substances 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
239000002904 solvent Substances 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
239000013543 active substance Substances 0.000 description 8
239000012043 crude product Substances 0.000 description 8
239000003814 drug Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
229940079593 drug Drugs 0.000 description 7
238000010828 elution Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
230000002349 favourable effect Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000945 filler Substances 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
150000005826 halohydrocarbons Chemical class 0.000 description 3
235000010445 lecithin Nutrition 0.000 description 3
239000000787 lecithin Substances 0.000 description 3
229940067606 lecithin Drugs 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
239000011732 tocopherol Substances 0.000 description 3
229930003799 tocopherol Natural products 0.000 description 3
235000019149 tocopherols Nutrition 0.000 description 3
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
235000010323 ascorbic acid Nutrition 0.000 description 2
239000011668 ascorbic acid Substances 0.000 description 2
229960005070 ascorbic acid Drugs 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 2
239000000872 buffer Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
235000005687 corn oil Nutrition 0.000 description 2
239000002285 corn oil Substances 0.000 description 2
239000002385 cottonseed oil Substances 0.000 description 2
235000012343 cottonseed oil Nutrition 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000004006 olive oil Substances 0.000 description 2
235000008390 olive oil Nutrition 0.000 description 2
150000007530 organic bases Chemical group 0.000 description 2
239000000312 peanut oil Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
235000003441 saturated fatty acids Nutrition 0.000 description 2
239000008159 sesame oil Substances 0.000 description 2
235000011803 sesame oil Nutrition 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
150000003626 triacylglycerols Chemical class 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
DCSLTSSPIJWEJN-UHFFFAOYSA-N (3beta,5beta)-3-[(6-deoxy-4-O-beta-D-glucopyranosyl-alpha-L-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxo-bufa-20,22-dienolide Natural products OC1C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(C)OC1OC(CC1(O)CCC2C3(O)CC4)CCC1(C=O)C2CCC3(C)C4C=1C=CC(=O)OC=1 DCSLTSSPIJWEJN-UHFFFAOYSA-N 0.000 description 1
DCSLTSSPIJWEJN-YRFFWODSSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,3r,4s,5r,6s)-3,4-dihydroxy-6-methyl-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[ Chemical compound C=1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C=O)CC[C@@H](C[C@@]5(O)CC[C@H]4[C@@]3(O)CC2)O[C@@H]2O[C@H]([C@@H]([C@@H](O)[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C)C=CC(=O)OC=1 DCSLTSSPIJWEJN-YRFFWODSSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
PCYADPMXIILFTP-UHFFFAOYSA-N 1,1-diethoxy-2-methoxyethane Chemical compound CCOC(COC)OCC PCYADPMXIILFTP-UHFFFAOYSA-N 0.000 description 1
BWZAUXRKSMJLMH-UHFFFAOYSA-N 1,1-diethoxyethylbenzene Chemical compound CCOC(C)(OCC)C1=CC=CC=C1 BWZAUXRKSMJLMH-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Polymers FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
ULVSHNOGEVXRDR-UHFFFAOYSA-N 1,1-dimethoxypropan-2-one Chemical compound COC(OC)C(C)=O ULVSHNOGEVXRDR-UHFFFAOYSA-N 0.000 description 1
GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-N 0.000 description 1
IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
NBDTZVVEDLDLSG-UHFFFAOYSA-N 4,6,6-trimethylheptan-2-yl acetate Chemical compound CC(C)(C)CC(C)CC(C)OC(C)=O NBDTZVVEDLDLSG-UHFFFAOYSA-N 0.000 description 1
DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 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
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
FUTYDOSGHYCQGU-UHFFFAOYSA-N Hellebrin Natural products CC1OC(OC2CCC3(C=O)C4CCC5(C)C(CCC5(O)C4CCC3(O)C2)C6=COC(=O)C=C6)C(OC7OC(CO)C(O)C(O)C7O)C(O)C1O FUTYDOSGHYCQGU-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 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
239000002841 Lewis acid Substances 0.000 description 1
241000195947 Lycopodium Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 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
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000003568 Sodium, potassium and calcium salts of fatty acids Substances 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
229920002472 Starch Polymers 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
235000019486 Sunflower oil Nutrition 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229910000091 aluminium hydride Inorganic materials 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
229960001950 benzethonium chloride Drugs 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
KPKQMJOJYKWXBX-UHFFFAOYSA-N butan-1-ol;tetrachloromethane Chemical compound CCCCO.ClC(Cl)(Cl)Cl KPKQMJOJYKWXBX-UHFFFAOYSA-N 0.000 description 1
CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
235000013969 calcium salts of fatty acid Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
239000003026 cod liver oil Substances 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
229940013361 cresol Drugs 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
MAQMEXSLUSZDQM-UHFFFAOYSA-N diethoxymethylbenzene Chemical compound CCOC(OCC)C1=CC=CC=C1 MAQMEXSLUSZDQM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
150000004862 dioxolanes Chemical class 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
125000005912 ethyl carbonate group Chemical class 0.000 description 1
239000003925 fat Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
235000004515 gallic acid Nutrition 0.000 description 1
229940074391 gallic acid Drugs 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
125000005456 glyceride group Chemical group 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N iso-butyl alcohol Natural products CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical class CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000010933 magnesium salts of fatty acid Nutrition 0.000 description 1
239000001778 magnesium salts of fatty acids Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229960003746 metildigoxin Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
235000014593 oils and fats Nutrition 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
210000003540 papillary muscle Anatomy 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
229960004838 phosphoric acid Drugs 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000010497 wheat germ oil Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA223,815A 1974-01-15 1975-04-03 Derivatives of desglucohellebrin and a process for their production Expired CA1055012A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AT30174A AT325954B (de)	1973-01-16	1974-01-15	Kreiselpumpe vertikaler bauart
AT279574A AT331423B (de)	1974-04-03	1974-04-03	Verfahren zur herstellung von neuen desglucohellebrin-derivaten

Publications (1)

Publication Number	Publication Date
CA1055012A true CA1055012A (en)	1979-05-22

Family

ID=25592242

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA223,815A Expired CA1055012A (en)	1974-01-15	1975-04-03	Derivatives of desglucohellebrin and a process for their production

Country Status (2)

Country	Link
CA (1)	CA1055012A (de)
HU (1)	HU170397B (de)

1975
- 1975-04-02 HU HUDE000887 patent/HU170397B/hu unknown
- 1975-04-03 CA CA223,815A patent/CA1055012A/en not_active Expired

Also Published As

Publication number	Publication date
HU170397B (de)	1977-06-28

Publication	Publication Date	Title
DE69125099T2 (de)	1997-06-19	Indolderivate
Clarkson et al.	2003	Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity
Su et al.	2008	Total synthesis of phenanthroindolizidine alkaloids (±)-antofine,(±)-deoxypergularinine, and their dehydro congeners and evaluation of their cytotoxic activity
EP3847183A1 (de)	2021-07-14	C19-gerüste und steroide und verfahren zur verwendung und herstellung davon
Cedrón et al.	2013	Preparation and antimalarial activity of semisynthetic lycorenine derivatives
US3987049A (en)	1976-10-19	Esters of dihydroapovincaminic acid
KR20080083044A (ko)	2008-09-12	트리테르펜퀴논 및 트리테르펜페놀 유도체와, 종양 및기생충성 질환의 치료를 위한 그 용도
JPS6237621B2 (de)	1987-08-13
AU3159293A (en)	1993-07-19	New BHT ether compounds and their use as hypolipidemic and antiatherosclerotic drugs
Barros et al.	2000	Fast galloylation of a sugar moiety: preparation of three monogalloylsucroses as references for antioxidant activity. A method for the selective deprotection of tert-butyldiphenylsilyl ethers
CA1055012A (en)	1979-05-22	Derivatives of desglucohellebrin and a process for their production
Mineno et al.	2014	Reductive coupling reaction of aldehydes using indium (III) triflate as the catalyst
Stamatov et al.	2005	Regioselective opening of an oxirane system with trifluoroacetic anhydride. A general method for the synthesis of 2-monoacyl-and 1, 3-symmetrical triacylglycerols
Tauber et al.	2015	Synthetic Approaches to Anti‐Inflammatory Macrolactones of the Oxacyclododecindione Type
Rodrıguez et al.	1998	Unusual Terpenes with Novel Carbon Skeletons from the West Indian Sea Whip Pseudopterogorgia elisabethae (Octocorallia)
Khersonsky et al.	2002	(±)-1, 2: 5, 6-Di-O-isopropylidene-myo-inositol and (±)-6-O-benzoyl-1, 2: 4, 5-di-O-isopropylidene-myo-inositol: a practical preparation of key intermediates for myo-inositol phosphates
Yoshida et al.	1988	Synthetic approaches toward mitomycins: construction of p-quinone moiety on 1-benzazocine derivative
Haberlin et al.	2014	Asymmetric synthesis and biological evaluation of 1, 3-and 1, 4-disubstituted benzo-type lipoxin A4 analogues
Neogi et al.	2005	Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives
US4038386A (en)	1977-07-26	Derivative of desglucohellebrin and therapeutic use
CN116925055B (zh)	2025-01-28	香豆素-哌嗪-呋喃酮杂化物及其制备方法和应用
KR101554562B1 (ko)	2015-09-21	마크로스펠라이드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 암 질환의 예방 또는 치료용 약학적 조성물
Stanoeva et al.	2004	Synthesis of 1-substituted 2, 9, 10-trioxatricyclo [4.3. 1.03, 8] decanes
ITOKAWA et al.	1985	Constituents of Torilis scabra DC II
Vadhadiya et al.	2014	Total synthesis of mangiferaelactone