DE3006097C2 - - Google Patents
Info
- Publication number
- DE3006097C2 DE3006097C2 DE3006097A DE3006097A DE3006097C2 DE 3006097 C2 DE3006097 C2 DE 3006097C2 DE 3006097 A DE3006097 A DE 3006097A DE 3006097 A DE3006097 A DE 3006097A DE 3006097 C2 DE3006097 C2 DE 3006097C2
- Authority
- DE
- Germany
- Prior art keywords
- geldanamycin
- group
- formula
- chloroform
- mixture
- Prior art date
- 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 - Fee Related
Links
- QTQAWLPCGQOSGP-GBTDJJJQSA-N geldanamycin Chemical class N1C(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@@H](O)[C@H](OC)C[C@@H](C)CC2=C(OC)C(=O)C=C1C2=O QTQAWLPCGQOSGP-GBTDJJJQSA-N 0.000 claims description 23
- -1 hydroxy, adamantyl Chemical group 0.000 claims description 13
- 239000002246 antineoplastic agent Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- JRZJKWGQFNTSRN-UHFFFAOYSA-N Geldanamycin Natural products C1C(C)CC(OC)C(O)C(C)C=C(C)C(OC(N)=O)C(OC)CCC=C(C)C(=O)NC2=CC(=O)C(OC)=C1C2=O JRZJKWGQFNTSRN-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910001923 silver oxide Inorganic materials 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- FSJSYDFBTIVUFD-XHTSQIMGSA-N (e)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C/C(C)=O.C\C(O)=C/C(C)=O FSJSYDFBTIVUFD-XHTSQIMGSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 235000001465 calcium Nutrition 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- BMNDNPMJFWNHCX-UHFFFAOYSA-N 2-(2-iminoethoxy)ethanimine Chemical compound N=CCOCC=N BMNDNPMJFWNHCX-UHFFFAOYSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- WYFYMWZHGYHGAR-CTPSMGKJSA-N [(6s,7r,8e,12z,14e)-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(propylamino)-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate Chemical compound C1C(C)CC(OC)[C@@H](O)[C@H](C)\C=C(C)\C(OC(N)=O)C(OC)\C=C/C=C(C)/C(=O)NC2=CC(=O)C(NCCC)=C1C2=O WYFYMWZHGYHGAR-CTPSMGKJSA-N 0.000 description 1
- DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000842 anti-protozoal effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003904 antiprotozoal agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 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 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- NSYZCCDSJNWWJL-YXOIYICCSA-N erythromycin ethylsuccinate Chemical class O1[C@H](C)C[C@H](N(C)C)[C@@H](OC(=O)CCC(=O)OCC)[C@@H]1O[C@H]1[C@@](O)(C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(OC)C2)[C@@H]1C NSYZCCDSJNWWJL-YXOIYICCSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 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
- 230000009036 growth inhibition Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ZWWPJQTUGCPRMO-UHFFFAOYSA-N methanimidoyl methanimidate Chemical compound N=COC=N ZWWPJQTUGCPRMO-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D225/06—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1721979A JPS55111470A (en) | 1979-02-19 | 1979-02-19 | Geldanamycin derivative, its preparation, antitumor drug comprising it as active ingredient |
| JP1721879A JPS55111469A (en) | 1979-02-19 | 1979-02-19 | Novel geldanamycin derivative, its preparation, and antitumor drug comprising it as active ingredient |
| JP1786879A JPS55111485A (en) | 1979-02-20 | 1979-02-20 | Novel geldanamycin derivative, its preparation, and antitumor drug comprising it as active ingredient |
| JP2138079A JPS55113767A (en) | 1979-02-27 | 1979-02-27 | Novel geldanamycin derivative, its preparation and antitumorigenic agent containing the same as effective component |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3006097A1 DE3006097A1 (de) | 1980-08-28 |
| DE3006097C2 true DE3006097C2 (enExample) | 1991-11-07 |
Family
ID=27456741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803006097 Granted DE3006097A1 (de) | 1979-02-19 | 1980-02-19 | Geldanamycinderivate und antitumormittel mit einem gehalt derselben |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4261989A (enExample) |
| AU (1) | AU532333B2 (enExample) |
| CA (1) | CA1113935A (enExample) |
| DE (1) | DE3006097A1 (enExample) |
| FR (1) | FR2449084A1 (enExample) |
| GB (1) | GB2042523B (enExample) |
| IT (1) | IT1147315B (enExample) |
| NL (1) | NL8000857A (enExample) |
Families Citing this family (150)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3234203A1 (de) * | 1981-09-17 | 1983-07-07 | Takeda Chemical Industries, Ltd., Osaka | Macbecin-derivate und deren herstellung |
| US4578391A (en) * | 1982-01-20 | 1986-03-25 | Yamanouchi Pharmaceutical Co., Ltd. | Oily compositions of antitumor drugs |
| JPS59102398A (ja) * | 1982-12-03 | 1984-06-13 | Takeda Chem Ind Ltd | 新規抗生物質およびその製造法 |
| JPH08502488A (ja) * | 1992-10-14 | 1996-03-19 | アメリカ合衆国 | 前立腺癌および初期神経悪性疾患に対するベンゾキノイドアンサマイシンの殺腫瘍活性 |
| US5387584A (en) * | 1993-04-07 | 1995-02-07 | Pfizer Inc. | Bicyclic ansamycins |
| JP2794342B2 (ja) * | 1993-06-29 | 1998-09-03 | ファイザー・インク． | 抗癌遺伝子剤および抗癌剤としてのアンサマイシン誘導体 |
| US5932566A (en) * | 1994-06-16 | 1999-08-03 | Pfizer Inc. | Ansamycin derivatives as antioncogene and anticancer agents |
| CA2218523A1 (en) * | 1995-05-02 | 1996-11-07 | William J. Welch | Inducement of thermotolerance with benzoquinonoid ansamycins |
| WO1998051702A1 (en) | 1997-05-14 | 1998-11-19 | Sloan-Kettering Institute For Cancer Research | Methods and compositions for destruction of selected proteins |
| US6852496B1 (en) | 1997-08-12 | 2005-02-08 | Oregon Health And Science University | Methods of screening for agents that promote nerve cell growth |
| US6747055B1 (en) | 1998-07-17 | 2004-06-08 | The United States Of America As Represented By The Department Of Health And Human Services | Water-soluble drugs and methods for their production |
| EP1098666B1 (en) | 1998-07-17 | 2013-01-16 | The United States of America, represented by the Secretary, Department of Health and Human Services | Water-soluble drugs and methods for their production |
| MXPA01005545A (es) * | 1998-12-07 | 2003-07-14 | Ecosmart Technologies Inc | Composicion y metodo para tratamiento de cancer que usan moduladores de transduccion de senales y aceites esenciales vegetales naturales. |
| US6174875B1 (en) * | 1999-04-01 | 2001-01-16 | University Of Pittsburgh | Benzoquinoid ansamycins for the treatment of cardiac arrest and stroke |
| AU769235B2 (en) | 1999-04-09 | 2004-01-22 | Sloan-Kettering Institute For Cancer Research | Methods and compositions for degradation and/or inhibition of her-family tyrosine kinases |
| US7238682B1 (en) | 1999-04-09 | 2007-07-03 | Sloan-Kettering Institute For Cancer Research | Methods and compositions for degradation and/or inhibition of HER-family tyrosine kinases |
| US6979574B1 (en) * | 1999-08-06 | 2005-12-27 | Institut Fuer Diagnostik Forshung Gmbh | Process for detecting binding reactions with use of the measurement of the relaxation of the double refraction of magnetic particles |
| US6887853B2 (en) * | 2000-06-29 | 2005-05-03 | The Trustees Of Boston University | Use of geldanamycin and related compounds for treatment of fibrogenic disorders |
| US6946456B2 (en) * | 2000-07-28 | 2005-09-20 | Sloan-Kettering Institute For Cancer Research | Methods for treating cell proliferative disorders and viral infections |
| JP2004512381A (ja) | 2000-11-02 | 2004-04-22 | スローン−ケッタリング・インスティテュート・フォー・キャンサー・リサーチ | Ｈｓｐ９０インヒビターの使用により細胞毒性剤の効力を増強させる方法 |
| US20060079493A1 (en) * | 2001-03-01 | 2006-04-13 | Lawrence Fritz | Methods for treating genetically- defined proliferative disorders with hsp90 inhibitors |
| KR100831133B1 (ko) * | 2001-03-30 | 2008-05-20 | 더 가브먼트 오브 더 유나이티드 스테이츠 오브 아메리카, 리프리젠티드 바이 더 세크러테리, 디파트먼트 오브 헬쓰 앤드 휴먼 서비씨즈 | 겔다나마이신 유도체 및 그를 사용하는 암 치료 방법 |
| WO2002094196A2 (en) * | 2001-05-23 | 2002-11-28 | Sloan Kettering Institute For Cancer Research | Method of treatment for cancers associated with elevated |
| US20090197852A9 (en) * | 2001-08-06 | 2009-08-06 | Johnson Robert G Jr | Method of treating breast cancer using 17-AAG or 17-AG or a prodrug of either in combination with a HER2 inhibitor |
| WO2003013430A2 (en) * | 2001-08-06 | 2003-02-20 | Kosan Biosciences, Inc. | Benzoquinone ansamycins |
| US6872715B2 (en) | 2001-08-06 | 2005-03-29 | Kosan Biosciences, Inc. | Benzoquinone ansamycins |
| EP1923061A1 (en) | 2001-09-24 | 2008-05-21 | Conforma Therapeutic Corporation | Process for preparing 17-Allyl amino geldanamycin (17-AAG) and other ansamycins |
| WO2003026571A2 (en) * | 2001-09-24 | 2003-04-03 | Conforma Therapeutics Corporation | Process for preparing 17-allyl amino geldanamycin (17-aag) and other ansamycins |
| US7465718B2 (en) * | 2002-02-08 | 2008-12-16 | Conforma Therapeutics Corporation | Ansamycins having improved pharmacological and biological properties |
| AU2003226285B2 (en) * | 2002-04-10 | 2008-01-03 | Conforma Therapeutics Corporation | Ansamycin formulations and methods for producing and using same |
| US20060148776A1 (en) * | 2003-03-13 | 2006-07-06 | Conforma Therapeutics Corporation | Drug formulations having long and medium chain triglycerides |
| US20050020534A1 (en) * | 2003-05-30 | 2005-01-27 | Kosan Biosciences, Inc. | Method for treating diseases using HSP90-inhibiting agents in combination with antimetabolites |
| US20050054625A1 (en) * | 2003-05-30 | 2005-03-10 | Kosan Biosciences, Inc. | Method for treating diseases using HSP90-inhibiting agents in combination with nuclear export inhibitors |
| US20050020556A1 (en) * | 2003-05-30 | 2005-01-27 | Kosan Biosciences, Inc. | Method for treating diseases using HSP90-inhibiting agents in combination with platinum coordination complexes |
| US20050020557A1 (en) * | 2003-05-30 | 2005-01-27 | Kosan Biosciences, Inc. | Method for treating diseases using HSP90-inhibiting agents in combination with enzyme inhibitors |
| US20050054589A1 (en) * | 2003-05-30 | 2005-03-10 | Kosan Biosciences, Inc. | Method for treating diseases using HSP90-inhibiting agents in combination with antibiotics |
| US7691838B2 (en) * | 2003-05-30 | 2010-04-06 | Kosan Biosciences Incorporated | Method for treating diseases using HSP90-inhibiting agents in combination with antimitotics |
| US20050026893A1 (en) * | 2003-05-30 | 2005-02-03 | Kosan Biosciences, Inc. | Method for treating diseases using HSP90-inhibiting agents in combination with immunosuppressants |
| US7241754B2 (en) * | 2003-06-13 | 2007-07-10 | Kosan Biosciences, Inc. | 2-Desmethyl ansamycin compounds |
| US6855705B1 (en) | 2003-11-12 | 2005-02-15 | Kosan Biosciences, Inc. | 11-O-methylgeldanamycin compounds |
| WO2005056531A1 (en) | 2003-11-12 | 2005-06-23 | Kosan Biosciences, Inc. | 11-o-methylgeldanamycin compounds |
| US6875863B1 (en) | 2003-11-12 | 2005-04-05 | Kosan Biosciences, Inc. | 11-O-methylgeldanamycin compounds |
| US6887993B1 (en) | 2003-11-12 | 2005-05-03 | Kosan Biosciences, Inc. | 11-O-methylgeldanamycin compounds |
| PT1716119E (pt) | 2003-12-23 | 2013-06-04 | Infinity Discovery Inc | Análogos de ansamicinas contendo benzoquinona para o tratamento do cancro |
| US20060019941A1 (en) * | 2003-12-23 | 2006-01-26 | Infinity Pharmaceuticals, Inc. | Analogs of benzoquinone-containing ansamycins and methods of use thereof |
| WO2005072766A2 (en) * | 2004-01-27 | 2005-08-11 | Boys Town National Research Hospital | Peptides that bind to hsp90 proteins |
| DK2295056T5 (en) | 2004-03-15 | 2016-11-28 | Sunesis Pharmaceuticals Inc | Use of SNS-595 to treat leukemia |
| WO2005105077A1 (en) * | 2004-04-28 | 2005-11-10 | Massachusetts Eye & Ear Infirmary | Inflammatory eye disease |
| US20050256097A1 (en) * | 2004-05-11 | 2005-11-17 | Kosan Biosciences, Inc. | Pharmaceutical solution formulations containing 17-AAG |
| US7259156B2 (en) | 2004-05-20 | 2007-08-21 | Kosan Biosciences Incorporated | Geldanamycin compounds and method of use |
| US20080171687A1 (en) * | 2004-09-16 | 2008-07-17 | Abraxis Bioscience, Inc. | Compositions And Methods For The Preparation And Administration Of Poorly Water Soluble Drugs |
| US20060067953A1 (en) * | 2004-09-29 | 2006-03-30 | Conforma Therapeutics Corporation | Oral pharmaceutical formulations and methods for producing and using same |
| EP1861070B1 (en) * | 2005-02-18 | 2018-01-17 | Abraxis BioScience, LLC | Drugs with improved hydrophobicity for incorporation in medical devices |
| NZ561939A (en) | 2005-03-30 | 2011-03-31 | Conforma Therapeutics Corp | Alkynyl pyrrolopyrimidines and related analogs as HSP90-inhibitors |
| CN101189006A (zh) * | 2005-04-07 | 2008-05-28 | 康福玛医药公司 | 基于磷脂的药物制剂及其生产和使用方法 |
| EP1871343A2 (en) | 2005-04-12 | 2008-01-02 | Wisconsin Alumni Research Foundation | Micelle composition of polymer and passenger drug |
| US7691392B2 (en) * | 2005-04-29 | 2010-04-06 | Kosan Biosciences Incorporated | Method of treating multiple myeloma using 17-AAG or 17-AG or a prodrug of either |
| WO2006119032A1 (en) * | 2005-04-29 | 2006-11-09 | Kosan Biosciences Incorporated | Method of treating multiple myeloma using 17-aag or 17-ag or a prodrug of either in combination with a proteasome inhibitor |
| US20080032719A1 (en) * | 2005-10-01 | 2008-02-07 | Outland Research, Llc | Centralized establishment-based tracking and messaging service |
| WO2007002093A2 (en) * | 2005-06-21 | 2007-01-04 | Infinity Discovery, Inc. | Ansamycin formulations and methods of use thereof |
| US8580814B2 (en) * | 2006-04-03 | 2013-11-12 | Sunesis Pharmaceuticals, Inc. | Methods of using (+)-1,4-dihydro-7-[(3S,4S)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4- oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid for treatment of cancer |
| EP1937258A2 (en) * | 2005-09-23 | 2008-07-02 | Conforma Therapeutics Corporation | Anti-tumor methods using multi drug resistance independent synthetic hsp90 inhibitors |
| US20090042847A1 (en) * | 2005-11-23 | 2009-02-12 | Kosan Biosciences Incorporated | 17-allylamino-17-demethoxygeldanamycin polymorphs and formulations |
| US7648976B2 (en) * | 2005-11-23 | 2010-01-19 | Bristol-Myers Squibb Company | 17-allylamino-17-demethoxygeldanamycin polymorphs and formulations |
| EP1954265A2 (en) * | 2005-12-01 | 2008-08-13 | Conforma Therapeutics Corporation | Compositions containing ansamycin |
| US20070167422A1 (en) * | 2006-01-18 | 2007-07-19 | Yu Kwok S | Pharmaceutical compositions comprising 17-allylamino-17-demethoxygeldanamycin |
| WO2007097839A2 (en) * | 2006-02-16 | 2007-08-30 | Massachusetts Eye And Ear Infirmary | Ansamycin analogs or heat shock 90 inhibitors in combination with pdt treatin conditions of the eye |
| KR20090021215A (ko) | 2006-06-12 | 2009-02-27 | 선에시스 파마슈티컬스 인코포레이티드 | 암의 치료를 위한 화합물 및 조성물 |
| DK2049109T3 (en) * | 2006-08-02 | 2016-01-11 | Sunesis Pharmaceuticals Inc | Combined use of (+) - 1,4-dihydro-7 - [(3S, 4S) -3-methoxy-4- (methylamino) -1-pyrrolidinyl] -4-oxo-1- (2-thiazolyl) -1,8-naphthyridine-3-carboxylic acid and cytarabine (Ara-C) for the treatment of leukemia |
| PE20081506A1 (es) * | 2006-12-12 | 2008-12-09 | Infinity Discovery Inc | Formulaciones de ansamicina |
| WO2008094438A1 (en) | 2007-01-26 | 2008-08-07 | Kosan Biosciences Incorporated | Macrolactams by engineered biosynthesis |
| US8303960B2 (en) * | 2007-02-27 | 2012-11-06 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Radiolabeled affibody molecules |
| BRPI0810835A2 (pt) * | 2007-04-12 | 2015-06-16 | Infinity Discovery Inc | Formulações de hidroquinona ansamicina |
| EP2079309B1 (en) * | 2007-04-12 | 2015-11-11 | Joyant Pharmaceuticals Inc | SMAC MIMEE DIMERS AND TRIMERS USEFUL AS ANTICANCER AGENTS |
| EP2180880A2 (en) * | 2007-07-09 | 2010-05-05 | Glen S. Kwon | Micelle encapsulation of therapeutic agents |
| WO2009026548A1 (en) * | 2007-08-23 | 2009-02-26 | The Regents Of The University Of Colorado | Hsp90 inhibitors with modified toxicity |
| JP2011501731A (ja) * | 2007-09-10 | 2011-01-13 | ユニバーシティ オブ マサチューセッツ | ミトコンドリア標的化抗腫瘍剤 |
| EP3141250A1 (en) * | 2007-10-22 | 2017-03-15 | Sunesis Pharmaceuticals, Inc. | Methods of using (+)-1,4-dihydro-7-[(3s,4s)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid in combination therapy |
| US7960420B2 (en) * | 2007-12-21 | 2011-06-14 | Joyant Pharmaceuticals, Inc | Diazonamide analogs with improved solubility |
| CN101220068B (zh) * | 2008-01-18 | 2012-06-13 | 中国医学科学院医药生物技术研究所 | 一组格尔德霉素衍生物及其制备方法 |
| US20090258869A1 (en) * | 2008-02-08 | 2009-10-15 | The Regents Of The University Of California | Methods and compounds for treatment or prevention of substance-related disorders |
| US7989482B2 (en) * | 2008-04-29 | 2011-08-02 | Joyant Pharmaceuticals, Inc. | Indoline anti-cancer agents |
| WO2009143485A1 (en) * | 2008-05-22 | 2009-11-26 | Joyant Pharmaceuticals, Inc. | Diazonamide analogs |
| WO2010045442A1 (en) * | 2008-10-15 | 2010-04-22 | Infinity Discovery, Inc. | Ansamycin hydroquinone compositions |
| DE102008060549A1 (de) | 2008-12-04 | 2010-06-10 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Wirkstoff-Peptid-Konstrukt zur extrazellulären Anreicherung |
| US8236329B2 (en) | 2009-09-25 | 2012-08-07 | Wisconsin Alumni Research Foundation | Micelle encapsulation of therapeutic agents |
| JPWO2011040421A1 (ja) | 2009-09-29 | 2013-02-28 | 武田薬品工業株式会社 | スクリーニング方法 |
| EP2493879B1 (en) | 2009-10-28 | 2014-05-14 | Joyant Pharmaceuticals, Inc. | Dimeric smac mimetics |
| CN102603635B (zh) * | 2011-01-21 | 2016-08-03 | 杭州华东医药集团生物工程研究所有限公司 | 格尔德霉素衍生物及其制备方法和用途 |
| HUE037730T2 (hu) | 2011-04-22 | 2018-09-28 | Joyant Pharmaceuticals Inc | Diazonamid analógok |
| US8945627B2 (en) | 2011-05-05 | 2015-02-03 | Wisconsin Alumni Research Foundation | Micelles for the solubilization of gossypol |
| CN103857392A (zh) | 2011-10-14 | 2014-06-11 | 诺华股份有限公司 | 用于治疗增生性疾病的2-甲酰胺环氨基尿素衍生物与Hsp90抑制剂的组合 |
| US9603829B2 (en) | 2011-11-14 | 2017-03-28 | The Regents Of The University Of Colorado, A Body Corporate | HSP90 inhibitors with modified toxicity |
| US10023862B2 (en) | 2012-01-09 | 2018-07-17 | Arrowhead Pharmaceuticals, Inc. | Organic compositions to treat beta-catenin-related diseases |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| EP2904119B1 (en) | 2012-10-02 | 2020-06-17 | The General Hospital Corporation d/b/a Massachusetts General Hospital | Methods relating to dna-sensing pathway related conditions |
| RU2015121424A (ru) | 2012-11-07 | 2016-12-27 | Новартис Аг | Комбинированная терапия |
| LT2958907T (lt) | 2013-02-19 | 2018-04-25 | Novartis Ag | Benzotiofeno dariniai ir jų kompozicijos, kaip selektyvūs estrogeno receptorių degradavimo agentai |
| CN103360312B (zh) * | 2013-07-22 | 2015-06-03 | 山东大学 | 一组格尔德霉素衍生物及其应用 |
| CN105764502A (zh) | 2013-07-26 | 2016-07-13 | 现代化制药公司 | 改善比生群及其类似物及衍生物的治疗益处的组合方法 |
| WO2015092634A1 (en) | 2013-12-16 | 2015-06-25 | Novartis Ag | 1,2,3,4-tetrahydroisoquinoline compounds and compositions as selective estrogen receptor antagonists and degraders |
| JO3517B1 (ar) | 2014-01-17 | 2020-07-05 | Novartis Ag | ان-ازاسبيرو الكان حلقي كبديل مركبات اريل-ان مغايرة وتركيبات لتثبيط نشاط shp2 |
| CN105899493B (zh) | 2014-01-17 | 2019-03-29 | 诺华股份有限公司 | 用于抑制shp2活性的1-(三嗪-3-基/哒嗪-3-基)-哌(-嗪)啶衍生物及其组合物 |
| CN105899491B (zh) | 2014-01-17 | 2019-04-02 | 诺华股份有限公司 | 用于抑制shp2活性的1-哒嗪-/三嗪-3-基-哌(-嗪)/啶/吡咯烷衍生物及其组合物 |
| US10189813B2 (en) | 2015-03-25 | 2019-01-29 | Novartis Ag | Formylated N-heterocyclic derivatives as FGFR4 inhibitors |
| CN108024989B (zh) | 2015-06-12 | 2021-08-03 | 威斯康星校友研究基金会 | 用作强效放射敏化剂的多药组合 |
| ES2741746T3 (es) | 2015-06-19 | 2020-02-12 | Novartis Ag | Compuestos y composiciones para inhibir la actividad de SHP2 |
| JP6718889B2 (ja) | 2015-06-19 | 2020-07-08 | ノバルティス アーゲー | Ｓｈｐ２の活性を阻害するための化合物および組成物 |
| CN107787323B (zh) | 2015-06-19 | 2020-09-01 | 诺华股份有限公司 | 用于抑制shp2活性的化合物和组合物 |
| MA44334A (fr) | 2015-10-29 | 2018-09-05 | Novartis Ag | Conjugués d'anticorps comprenant un agoniste du récepteur de type toll |
| DK3452465T3 (da) | 2016-05-04 | 2021-02-08 | Genoscience Pharma | Substituerede 2,4-diaminoquinolinderivater til anvendelse til behandling af proliferative sygdomme |
| MX383856B (es) | 2016-06-14 | 2025-03-14 | Novartis Ag | Compuestos y composiciones para inhibir la actividad de shp2. |
| AR111651A1 (es) | 2017-04-28 | 2019-08-07 | Novartis Ag | Conjugados de anticuerpos que comprenden agonistas del receptor de tipo toll y terapias de combinación |
| CA3074304A1 (en) | 2017-09-11 | 2019-03-14 | Krouzon Pharmaceuticals, Inc. | Octahydrocyclopenta[c]pyrrole allosteric inhibitors of shp2 |
| AR116109A1 (es) | 2018-07-10 | 2021-03-31 | Novartis Ag | Derivados de 3-(5-amino-1-oxoisoindolin-2-il)piperidina-2,6-diona y usos de los mismos |
| EP4640241A3 (en) | 2018-07-25 | 2025-12-10 | Advanced Accelerator Applications S.A. | Stable, concentrated radionuclide complex solutions |
| WO2020021465A1 (en) | 2018-07-25 | 2020-01-30 | Advanced Accelerator Applications (Italy) S.R.L. | Method of treatment of neuroendocrine tumors |
| CR20210175A (es) | 2018-09-18 | 2021-06-01 | Nikang Therapeutics Inc | Derivados de anillo tricíclico condensado como inhibidores de la fosfatasa de homología a src 2 (shp2) |
| EP3856349A1 (en) | 2018-09-25 | 2021-08-04 | Black Diamond Therapeutics, Inc. | Tyrosine kinase inhibitor compositions, methods of making and methods of use |
| BR112021005513A2 (pt) | 2018-09-25 | 2021-06-22 | Black Diamond Therapeutics, Inc. | derivados de quinazolina como inibidor de tirosina quinase, composições, métodos de fabricação e uso dos mesmos |
| WO2020064693A1 (en) | 2018-09-25 | 2020-04-02 | Advanced Accelerator Applications (Italy) Srl | Combination therapy |
| JP2022502385A (ja) | 2018-09-29 | 2022-01-11 | ノバルティス アーゲー | Ｓｈｐ２の活性を阻害するための化合物の製造方法 |
| CN113271945A (zh) | 2018-12-20 | 2021-08-17 | 诺华股份有限公司 | 包含3-(1-氧代异吲哚啉-2-基)哌啶-2,6-二酮衍生物的给药方案和药物组合 |
| EP3924055B1 (en) | 2019-02-15 | 2024-04-03 | Novartis AG | Substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
| CN113490528B (zh) | 2019-02-15 | 2024-12-03 | 诺华股份有限公司 | 3-(1-氧代-5-(哌啶-4-基)异吲哚啉-2-基)哌啶-2,6-二酮衍生物及其用途 |
| EP4013749A1 (en) | 2019-08-15 | 2022-06-22 | Black Diamond Therapeutics, Inc. | Alkynyl quinazoline compounds |
| CN115175937A (zh) | 2019-12-20 | 2022-10-11 | 诺华股份有限公司 | 用于治疗骨髓纤维化和骨髓增生异常综合征的抗TIM-3抗体MBG453和抗TGF-β抗体NIS793与或不与地西他滨或抗PD-1抗体斯巴达珠单抗的组合 |
| WO2021195206A1 (en) | 2020-03-24 | 2021-09-30 | Black Diamond Therapeutics, Inc. | Polymorphic forms and related uses |
| CN115916199A (zh) | 2020-06-23 | 2023-04-04 | 诺华股份有限公司 | 包含3-(1-氧代异吲哚啉-2-基)哌啶-2,6-二酮衍生物的给药方案 |
| WO2022029573A1 (en) | 2020-08-03 | 2022-02-10 | Novartis Ag | Heteroaryl substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
| EP4204020A1 (en) | 2020-08-31 | 2023-07-05 | Advanced Accelerator Applications International S.A. | Method of treating psma-expressing cancers |
| WO2022043557A1 (en) | 2020-08-31 | 2022-03-03 | Advanced Accelerator Applications International Sa | Method of treating psma-expressing cancers |
| WO2022043556A1 (en) | 2020-08-31 | 2022-03-03 | Novartis Ag | Stable radiopharmaceutical composition |
| US20250018049A1 (en) | 2020-12-22 | 2025-01-16 | Nikang Therapeutics, Inc. | Compounds for degrading cyclin-dependent kinase 2 via ubiquitin proteosome pathway |
| JP2024504932A (ja) | 2021-01-13 | 2024-02-02 | モンテ ローザ セラピューティクス， インコーポレイテッド | イソインドリノン化合物 |
| WO2022170052A1 (en) | 2021-02-05 | 2022-08-11 | Black Diamond Therapeutics, Inc. | Quinazoline derivatives, pyridopyrimidine derivatives, pyrimidopyrimidine derivatives, and uses thereof |
| TW202304979A (zh) | 2021-04-07 | 2023-02-01 | 瑞士商諾華公司 | 抗ＴＧＦβ抗體及其他治療劑用於治療增殖性疾病之用途 |
| EP4323350A1 (en) | 2021-04-14 | 2024-02-21 | Monte Rosa Therapeutics AG | Isoindolinone compounds |
| WO2022219412A1 (en) | 2021-04-14 | 2022-10-20 | Monte Rosa Therapeutics Ag | Isoindolinone amide compounds useful to treat diseases associated with gspt1 |
| AR125874A1 (es) | 2021-05-18 | 2023-08-23 | Novartis Ag | Terapias de combinación |
| TW202317589A (zh) | 2021-07-14 | 2023-05-01 | 美商尼坎醫療公司 | 作為ｋｒａｓ抑制劑的伸烷基衍生物 |
| EP4499634A1 (en) | 2022-03-28 | 2025-02-05 | Nikang Therapeutics, Inc. | Sulfonamido derivatives as cyclin-dependent kinase 2 inhibitors |
| WO2023214325A1 (en) | 2022-05-05 | 2023-11-09 | Novartis Ag | Pyrazolopyrimidine derivatives and uses thereof as tet2 inhibitors |
| CN119790053A (zh) | 2022-06-08 | 2025-04-08 | 霖康疗法公司 | 作为细胞周期蛋白依赖性激酶2抑制剂的磺酰胺衍生物 |
| KR20250103630A (ko) | 2022-11-11 | 2025-07-07 | 니캉 테라퓨틱스 인코포레이티드 | 유비퀴틴 프로테아좀 경로를 통해 사이클린-의존성 키나제 2를 분해하기 위한 2,5-치환된 피리미딘 유도체를 함유하는 이작용성 화합물 |
| WO2025072462A1 (en) | 2023-09-27 | 2025-04-03 | Nikang Therapeutics, Inc. | Sulfonamide derivatives as cyclin-dependent kinase 2 inhibitors |
| WO2025117616A1 (en) | 2023-11-27 | 2025-06-05 | Nikang Therapeutics, Inc. | Bifunctional compounds containing 2,5-substituted pyrimidine derivatives for degrading cyclin-dependent kinase 2 and cyclin-dependent kinase 4 via ubiquitin proteasome pathway |
| WO2025117981A1 (en) | 2023-12-02 | 2025-06-05 | Nikang Therapeutics, Inc. | Bifunctional compounds containing 2,5-substituted pyrimidine derivatives for degrading cyclin-dependent kinase 2 via ubiquitin proteasome pathway |
| WO2025212828A1 (en) | 2024-04-03 | 2025-10-09 | Nikang Therapeutics, Inc. | Bifunctional compounds containing 2,5-substituted pyrimidine derivatives for degrading cyclin-dependent kinase 2 and cyclin-dependent kinase 4 via ubiquitin proteasome pathway |
| WO2025240536A1 (en) | 2024-05-15 | 2025-11-20 | Nikang Therapeutics, Inc. | Bifunctional compounds containing 2,5-substituted pyrimidine derivatives for degrading cyclin-dependent kinase 2 and/or cyclin-dependent kinase 4 via ubiquitin proteasome pathway |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987035A (en) * | 1974-04-05 | 1976-10-19 | University Of Illinois Foundation | Biologically active compounds |
-
1980
- 1980-01-03 US US06/109,314 patent/US4261989A/en not_active Expired - Lifetime
- 1980-01-08 AU AU54430/80A patent/AU532333B2/en not_active Ceased
- 1980-01-15 GB GB8001321A patent/GB2042523B/en not_active Expired
- 1980-02-06 FR FR8002589A patent/FR2449084A1/fr active Granted
- 1980-02-12 NL NL8000857A patent/NL8000857A/nl not_active Application Discontinuation
- 1980-02-13 CA CA345,489A patent/CA1113935A/en not_active Expired
- 1980-02-19 IT IT20017/80A patent/IT1147315B/it active
- 1980-02-19 DE DE19803006097 patent/DE3006097A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2042523A (en) | 1980-09-24 |
| US4261989A (en) | 1981-04-14 |
| NL8000857A (nl) | 1980-08-21 |
| AU5443080A (en) | 1980-08-28 |
| AU532333B2 (en) | 1983-09-29 |
| FR2449084A1 (fr) | 1980-09-12 |
| IT8020017A0 (it) | 1980-02-19 |
| IT1147315B (it) | 1986-11-19 |
| FR2449084B1 (enExample) | 1983-12-23 |
| DE3006097A1 (de) | 1980-08-28 |
| CA1113935A (en) | 1981-12-08 |
| GB2042523B (en) | 1983-02-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3006097C2 (enExample) | ||
| DE69115570T2 (de) | Ureidoderivate von poly-4-amino-2-carboxy-1-methylverbindungen | |
| EP0134400B1 (de) | Anti-sekretorische, Fluoralkoxy-substituierte Pyridylmethylthio-(oder sulfinyl-)benzimidazole | |
| DE69522490T2 (de) | Platinkomplexe | |
| DE69623745T2 (de) | Derivate von DC 107 | |
| EP0281902B1 (de) | Bis-naphthalimide, ihre Herstellung und Verwendung | |
| DE3010544A1 (de) | 1h-pyrrolo eckige klammer auf 2,1-c eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin- 2-acrylsaeureamid-verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| EP0299470A1 (de) | Imidazo[1,2-a]pyridine | |
| AT394853B (de) | Verfahren zur herstellung von neuen mitosanderivaten | |
| EP0127763A1 (de) | Tricyclische Ether, Verfahren zu ihrer Herstellung, ihre Anwendung und sie enthaltende Arzneimittel | |
| EP0297380B1 (de) | Indolylpropanole, Verfahren zu ihrer Herstellung und ihre Verwendung sowie die Verbindungen enthaltende Zubereitungen | |
| DE2149750A1 (de) | Erythromycin-Derivate | |
| EP0405298B1 (de) | Thienopyran-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1695375C3 (de) | 25-Desacetyl-rifamycin-SV-derivate u. Verfahren zu ihrer Herstellung | |
| DE3788389T2 (de) | Cervinomycinabkömmlinge als antibiotika und deren herstellungsverfahren. | |
| EP0303571A1 (de) | Biphenylyl-Verbindungen | |
| DE60205470T2 (de) | Analoge von 4-beta-1''-[(2''-(substitutierte-benzoyl)anilin]-podophyllotoxin zur verwendung als antikrebs-agentia 4-beta-1"-∫2"-(substituted benzoyl) anilino∫ podophyllotoxin analogues useful as anticancer agents | |
| AT390618B (de) | Verfahren zur herstellung von neuen anthracyclinglykosiden | |
| CH644121A5 (de) | 9h-pyrido(3,4-b)indol-derivate. | |
| DE3871836T2 (de) | Mitomycin-derivate. | |
| EP0088986B1 (de) | Bicyclische Phenolether, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
| EP0180833B1 (de) | 4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel | |
| WO1996002540A1 (de) | Heterocyclyl-1-phenyl substituierte chinoloncarbonsäuren als antivirale mittel | |
| AT390614B (de) | Verfahren zur herstellung von neuen 2-halogen-nicergolinen | |
| EP0020941A1 (de) | Substituierte 3-(1-Pyrrolidinyl)-5-sulfamoyl-benzoesäure-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Zubereitungen, die sie enthalten und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |