CS172591A3 - Radicicol derivatives, process of their preparation and use - Google Patents

Radicicol derivatives, process of their preparation and use Download PDF

Info

Publication number: CS172591A3
Authority: CS; Czechoslovakia
Prior art keywords: groups; substituted; carbon atoms; group; substituents
Prior art date: 1990-06-06

Application number

CS911725A

Other languages

Czech (cs)

English (en)

Inventor

Yukio Sugimura

Kimio Iino

Yoshio Tsujita

Yoko Shimada

Tomowo Kobayashi

Takeshi Kagasaki

Original Assignee

Sankyo Co

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.)

1990-06-06

Filing date

1991-06-06

Publication date

1992-04-15

1991-06-06 Application filed by Sankyo Co filed Critical Sankyo Co

1992-04-15 Publication of CS172591A3 publication Critical patent/CS172591A3/cs

Links

AECPBJMOGBFQDN-YMYQVXQQSA-N radicicol Chemical class C1CCCC(=O)C[C@H]2[C@H](Cl)C(=O)CC(=O)[C@H]2C(=O)O[C@H](C)C[C@H]2O[C@@H]21 AECPBJMOGBFQDN-YMYQVXQQSA-N 0.000 title claims abstract description 75
238000000034 method Methods 0.000 title claims description 69
238000002360 preparation method Methods 0.000 title claims description 8
230000008569 process Effects 0.000 title description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
239000000126 substance Substances 0.000 claims abstract description 17
-1 carbamoyloxy Chemical group 0.000 claims description 495
125000004432 carbon atom Chemical group C* 0.000 claims description 277
125000001424 substituent group Chemical group 0.000 claims description 255
150000001875 compounds Chemical class 0.000 claims description 175
125000003118 aryl group Chemical group 0.000 claims description 155
239000000460 chlorine Substances 0.000 claims description 94
239000002904 solvent Substances 0.000 claims description 87
125000000217 alkyl group Chemical group 0.000 claims description 75
VYGYNVZNSSTDLJ-HKCOAVLJSA-N monorden Natural products CC1CC2OC2C=C/C=C/C(=O)CC3C(C(=CC(=C3Cl)O)O)C(=O)O1 VYGYNVZNSSTDLJ-HKCOAVLJSA-N 0.000 claims description 66
229930192524 radicicol Natural products 0.000 claims description 64
125000001931 aliphatic group Chemical group 0.000 claims description 39
125000006413 ring segment Chemical group 0.000 claims description 38
125000003545 alkoxy group Chemical group 0.000 claims description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
125000000623 heterocyclic group Chemical group 0.000 claims description 33
125000004414 alkyl thio group Chemical group 0.000 claims description 28
125000002252 acyl group Chemical group 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
125000001589 carboacyl group Chemical group 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 21
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000001301 oxygen Substances 0.000 claims description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
206010028980 Neoplasm Diseases 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 16
125000004429 atom Chemical group 0.000 claims description 15
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 12
125000005110 aryl thio group Chemical group 0.000 claims description 12
125000004104 aryloxy group Chemical group 0.000 claims description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
150000001721 carbon Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 11
125000005017 substituted alkenyl group Chemical group 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
125000004423 acyloxy group Chemical group 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 9
125000000547 substituted alkyl group Chemical group 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000004426 substituted alkynyl group Chemical group 0.000 claims description 8
125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 7
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
125000005035 acylthio group Chemical group 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
WKVZMKDXJFCMMD-UVWUDEKDSA-L (5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one;azanide;n,3-bis(2-chloroethyl)-2-ox Chemical compound [NH2-].[NH2-].Cl[Pt+2]Cl.ClCCNP1(=O)OCCCN1CCCl.COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3C(O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 WKVZMKDXJFCMMD-UVWUDEKDSA-L 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
230000000259 anti-tumor effect Effects 0.000 abstract description 8
239000000543 intermediate Substances 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 description 162
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 76
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
238000000862 absorption spectrum Methods 0.000 description 60
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 60
230000003197 catalytic effect Effects 0.000 description 53
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
239000000203 mixture Substances 0.000 description 40
229940093499 ethyl acetate Drugs 0.000 description 39
235000019439 ethyl acetate Nutrition 0.000 description 39
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 38
239000000376 reactant Substances 0.000 description 36
239000002253 acid Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000003153 chemical reaction reagent Substances 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
238000004458 analytical method Methods 0.000 description 24
239000003795 chemical substances by application Substances 0.000 description 22
239000000243 solution Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
150000002170 ethers Chemical class 0.000 description 18
238000001228 spectrum Methods 0.000 description 18
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
238000000921 elemental analysis Methods 0.000 description 17
230000035484 reaction time Effects 0.000 description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001298 alcohols Chemical class 0.000 description 12
239000011777 magnesium Substances 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000000047 product Substances 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
239000003480 eluent Substances 0.000 description 11
241000699670 Mus sp. Species 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
239000007858 starting material Substances 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000007086 side reaction Methods 0.000 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
125000003710 aryl alkyl group Chemical group 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
239000013078 crystal Substances 0.000 description 7
230000001627 detrimental effect Effects 0.000 description 7
230000009931 harmful effect Effects 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004849 alkoxymethyl group Chemical group 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000010531 catalytic reduction reaction Methods 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
229910000288 alkali metal carbonate Inorganic materials 0.000 description 5
150000008041 alkali metal carbonates Chemical class 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
238000004821 distillation Methods 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
231100000989 no adverse effect Toxicity 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
125000004448 alkyl carbonyl group Chemical group 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
229910052697 platinum Inorganic materials 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000002271 resection Methods 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 3
125000005103 alkyl silyl group Chemical group 0.000 description 3
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
230000002939 deleterious effect Effects 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
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XIKYYQJBTPYKSG-UHFFFAOYSA-N nickel Chemical group [Ni].[Ni] XIKYYQJBTPYKSG-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
KPMKNHGAPDCYLP-UHFFFAOYSA-N nimustine hydrochloride Chemical compound Cl.CC1=NC=C(CNC(=O)N(CCCl)N=O)C(N)=N1 KPMKNHGAPDCYLP-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
125000004971 nitroalkyl group Chemical group 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
125000002811 oleoyl 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])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([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
125000002958 pentadecyl 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])[H] 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000005494 pyridonyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229930002330 retinoic acid Natural products 0.000 description 1
125000001444 retinoyl group Chemical group O=C([*])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
UOSKWYONTYQYHE-UHFFFAOYSA-J sodium trichloroalumane iodide Chemical compound [Na+].[I-].Cl[Al](Cl)Cl UOSKWYONTYQYHE-UHFFFAOYSA-J 0.000 description 1
239000003381 stabilizer Substances 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
230000000707 stereoselective effect Effects 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WAOWQLJJQBDGQC-UHFFFAOYSA-N tetraazanium;tetrafluoride Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[F-].[F-].[F-].[F-] WAOWQLJJQBDGQC-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
229960001727 tretinoin Drugs 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000002889 tridecyl 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])[H] 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
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
210000004881 tumor cell Anatomy 0.000 description 1
MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-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
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 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
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CS911725A 1990-06-06 1991-06-06 Radicicol derivatives, process of their preparation and use CS172591A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP14629990		1990-06-06

Publications (1)

Publication Number	Publication Date
CS172591A3 true CS172591A3 (en)	1992-04-15

Family

ID=15404539

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911725A CS172591A3 (en)	1990-06-06	1991-06-06	Radicicol derivatives, process of their preparation and use

Country Status (12)

Country	Link
US (1)	US5597846A (de)
EP (1)	EP0460950B1 (de)
KR (1)	KR920000763A (de)
CN (1)	CN1035381C (de)
AT (1)	ATE149498T1 (de)
CA (1)	CA2044018A1 (de)
CS (1)	CS172591A3 (de)
DE (1)	DE69124844D1 (de)
HU (1)	HUT60743A (de)
IE (1)	IE911915A1 (de)
PT (1)	PT97884B (de)
WO (1)	WO1991018905A1 (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
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US5731343A (en) *	1995-02-24	1998-03-24	The Scripps Research Institute	Method of use of radicicol for treatment of immunopathological disorders
ES2149468T3 (es) *	1995-04-26	2000-11-01	Kyowa Hakko Kogyo Kk	Derivados de radicicol.
ATE266017T1 (de)	1996-10-25	2004-05-15	Kyowa Hakko Kogyo Kk	Radicicolderivate
JP2002533389A (ja) *	1998-12-24	2002-10-08	ノーベーションファーマシューティカルズインコーポレーテッド	ｍＲＮＡ安定性に影響する化合物およびそのための使用
ATE526019T1 (de) *	2000-07-28	2011-10-15	Sloan Kettering Inst Cancer	Verfahren zur behandlung von zellproliferationen störungen und virusinfektionen
EP1315732B1 (de)	2000-08-25	2006-06-07	Sloan-Kettering Institute For Cancer Research	Radicicol und monocillin und ihre analogen und ihre anwendungen
JP2004529188A (ja) *	2001-05-23	2004-09-24	スローン − ケッタリングインスティチュートフォーキャンサーリサーチ	上昇に関連した癌の治療法
US20080108694A1 (en) *	2003-12-19	2008-05-08	Samuel J Danishefsky	Novel Macrocycles and Uses Thereof
EP2136799B1 (de) *	2006-08-11	2017-10-04	Universite De Strasbourg	Makrocyclische verbindungen als hemmer von kinase und hsp90
WO2009105755A2 (en)	2008-02-21	2009-08-27	Nexgenix Pharmaceuticals	Macrocyclic prodrug compounds useful as therapeutics
US20110190237A1 (en) *	2008-01-15	2011-08-04	Nexgenix Pharmaceuticals	Macrocyclic Prodrug Compounds Useful as Therapeutics
WO2009132010A1 (en) *	2008-04-21	2009-10-29	Chevron Phillips Chemical Company Lp	Methods and systems for making thiol compounds from terminal olefinic compounds

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DE903997C (de) *	1934-12-08	1954-02-15	Aeg	Einrichtung zur UEberwachung von zeitlich in veraenderlicher Staerke geleisteter Arbeit
CH441623A (de) *	1964-05-20	1967-08-15	Sandoz Ag	Verfahren zur Herstellung neuer Antibiotica
GB2013672B (en) *	1978-02-01	1982-06-09	Grace W R & Co	Process for the production of monorden and derivatives thereof
US4166764A (en) *	1978-02-01	1979-09-04	W. R. Grace & Co.	Production of monorden
US4228079A (en) *	1978-10-30	1980-10-14	W. R. Grace & Co.	Dialkoxy monorden derivatives

1991
- 1991-06-05 IE IE191591A patent/IE911915A1/en unknown
- 1991-06-05 KR KR1019910009445A patent/KR920000763A/ko not_active Ceased
- 1991-06-06 PT PT97884A patent/PT97884B/pt not_active IP Right Cessation
- 1991-06-06 CN CN91104853A patent/CN1035381C/zh not_active Expired - Fee Related
- 1991-06-06 HU HU911893A patent/HUT60743A/hu unknown
- 1991-06-06 CA CA002044018A patent/CA2044018A1/en not_active Abandoned
- 1991-06-06 AT AT91305111T patent/ATE149498T1/de active
- 1991-06-06 WO PCT/GB1991/000909 patent/WO1991018905A1/en not_active Ceased
- 1991-06-06 DE DE69124844T patent/DE69124844D1/de not_active Expired - Lifetime
- 1991-06-06 CS CS911725A patent/CS172591A3/cs unknown
- 1991-06-06 EP EP91305111A patent/EP0460950B1/de not_active Expired - Lifetime
1994
- 1994-09-23 US US08/311,518 patent/US5597846A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HU911893D0 (en)	1991-12-30
IE911915A1 (en)	1991-12-18
WO1991018905A1 (en)	1991-12-12
US5597846A (en)	1997-01-28
EP0460950B1 (de)	1997-03-05
EP0460950A1 (de)	1991-12-11
KR920000763A (ko)	1992-01-29
ATE149498T1 (de)	1997-03-15
CN1035381C (zh)	1997-07-09
CA2044018A1 (en)	1991-12-07
PT97884A (pt)	1992-03-31
PT97884B (pt)	1998-10-30
DE69124844D1 (de)	1997-04-10
HUT60743A (en)	1992-10-28
CN1059720A (zh)	1992-03-25

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DD297561A5 (de)	1992-01-16	Verwendung von phospholipid-derivaten als antivirale arzneimittel und neue phospholipide
DE69004143T2 (de)	1994-03-03	6-Fluorshikiminsäurederivate.
DE3107743A1 (de)	1981-12-03	Neue klasse von acylderivaten des carnitins, verfahren zu deren herstellung sowie ihre therapeutische verwendung
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DE69107431T2 (de)	1995-06-14	Deacetylcolchicinderivate.
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DE60002891T2 (de)	2004-03-11	Streptograminderivate, ihre herstellung und sie enthaltende zubereitungen
DD241600A5 (de)	1986-12-17	Verfahren zur herstellung von 4,4-dialkyl-2-azetidinon-verbindungen
DE69117578T2 (de)	1996-07-18	Delta-2-Cephemsulfone