UA61054C2 - Cytoctatics modified by carbohydrates - Google Patents
Cytoctatics modified by carbohydrates Download PDFInfo
- Publication number
- UA61054C2 UA61054C2 UA97115364A UA97115364A UA61054C2 UA 61054 C2 UA61054 C2 UA 61054C2 UA 97115364 A UA97115364 A UA 97115364A UA 97115364 A UA97115364 A UA 97115364A UA 61054 C2 UA61054 C2 UA 61054C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methanol
- dichloromethane
- mmol
- batracillin
- lysyl
- Prior art date
Links
- 150000001720 carbohydrates Chemical class 0.000 title description 108
- 235000014633 carbohydrates Nutrition 0.000 title description 108
- 239000000824 cytostatic agent Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 156
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000004472 Lysine Substances 0.000 claims description 15
- 125000000539 amino acid group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- -1 batracillin Chemical compound 0.000 claims description 7
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 235000018977 lysine Nutrition 0.000 claims description 6
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 4
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 4
- 235000004279 alanine Nutrition 0.000 claims description 4
- 229960003104 ornithine Drugs 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 230000001472 cytotoxic effect Effects 0.000 claims description 3
- PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 claims description 2
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- 229940127093 camptothecin Drugs 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 231100000433 cytotoxic Toxicity 0.000 claims description 2
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 2
- 229960004679 doxorubicin Drugs 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 2
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 2
- 229960001924 melphalan Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
- 235000014393 valine Nutrition 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000004471 Glycine Substances 0.000 claims 2
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 claims 1
- 125000000837 carbohydrate group Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 29
- 230000001085 cytostatic effect Effects 0.000 abstract description 5
- 235000000346 sugar Nutrition 0.000 abstract description 2
- 230000003834 intracellular effect Effects 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 125000006850 spacer group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1528
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1291
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 595
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 546
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 307
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 283
- 239000013078 crystal Substances 0.000 description 240
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 200
- 239000000203 mixture Substances 0.000 description 188
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 177
- 229910001868 water Inorganic materials 0.000 description 176
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 174
- 238000004809 thin layer chromatography Methods 0.000 description 173
- 238000000746 purification Methods 0.000 description 162
- 229910021529 ammonia Inorganic materials 0.000 description 153
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 121
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 120
- 239000000243 solution Substances 0.000 description 115
- 239000003208 petroleum Substances 0.000 description 98
- 239000000863 peptide conjugate Substances 0.000 description 97
- 239000000047 product Substances 0.000 description 91
- 229960000583 acetic acid Drugs 0.000 description 88
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- 238000001556 precipitation Methods 0.000 description 69
- 239000012362 glacial acetic acid Substances 0.000 description 63
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 54
- 238000003756 stirring Methods 0.000 description 49
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 43
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 42
- 239000000562 conjugate Substances 0.000 description 40
- 159000000000 sodium salts Chemical class 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000000706 filtrate Substances 0.000 description 30
- 239000000126 substance Substances 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- 230000008719 thickening Effects 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 235000011121 sodium hydroxide Nutrition 0.000 description 26
- 239000006260 foam Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- 239000000725 suspension Substances 0.000 description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 21
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- 238000007710 freezing Methods 0.000 description 21
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
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- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
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- 238000004108 freeze drying Methods 0.000 description 12
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- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 201000009546 lung large cell carcinoma Diseases 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 101150064967 pef-1 gene Proteins 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000011935 selective methylation Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/02—Halogenated hydrocarbons
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19512484A DE19512484A1 (de) | 1995-04-04 | 1995-04-04 | Kohlenhydratmodifizierte Cytostatika |
| PCT/EP1996/001279 WO1996031532A1 (de) | 1995-04-04 | 1996-03-22 | Kohlenhydratmodifizierte cytostatika |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA61054C2 true UA61054C2 (en) | 2003-11-17 |
Family
ID=7758679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA97115364A UA61054C2 (en) | 1995-04-04 | 1996-03-22 | Cytoctatics modified by carbohydrates |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6271342B1 (cs) |
| EP (1) | EP0819135B1 (cs) |
| JP (1) | JPH11502860A (cs) |
| KR (1) | KR19980703591A (cs) |
| CN (1) | CN1185786A (cs) |
| AT (1) | ATE186738T1 (cs) |
| AU (1) | AU713466B2 (cs) |
| BG (1) | BG63048B1 (cs) |
| BR (1) | BR9604825A (cs) |
| CA (1) | CA2217164A1 (cs) |
| CZ (1) | CZ291098B6 (cs) |
| DE (2) | DE19512484A1 (cs) |
| DK (1) | DK0819135T3 (cs) |
| EE (1) | EE03619B1 (cs) |
| ES (1) | ES2140078T3 (cs) |
| GR (1) | GR3032605T3 (cs) |
| HU (1) | HUP9800513A3 (cs) |
| IS (1) | IS1822B (cs) |
| MX (1) | MX9707613A (cs) |
| NO (1) | NO974564L (cs) |
| NZ (1) | NZ305855A (cs) |
| PL (1) | PL183574B1 (cs) |
| RU (1) | RU2170234C2 (cs) |
| SK (1) | SK281785B6 (cs) |
| TW (1) | TW384290B (cs) |
| UA (1) | UA61054C2 (cs) |
| WO (1) | WO1996031532A1 (cs) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4459297A (en) * | 1996-09-30 | 1998-04-24 | Bayer Aktiengesellschaft | Glycoconjugates from modified camptothecin derivates (20-o-linkage) |
| DE19640970A1 (de) * | 1996-10-04 | 1998-04-16 | Bayer Ag | Modifizierte Cytostatika |
| JP3101710B2 (ja) | 1997-02-28 | 2000-10-23 | 工業技術院長 | 硫酸化オリゴ糖化合物 |
| ID23424A (id) * | 1997-05-14 | 2000-04-20 | Bayer Ag | Glikokonjugat dari 20(s)-kamptotesin |
| ATE423776T1 (de) | 1997-09-15 | 2009-03-15 | Procter & Gamble | Antimikrobielle chinolone, ihre zusammensetzungen und ihre verwendungen |
| US6387928B1 (en) | 1997-09-15 | 2002-05-14 | The Procter & Gamble Co. | Antimicrobial quinolones, their compositions and uses |
| US6613879B1 (en) * | 1999-05-14 | 2003-09-02 | Boehringer Ingelheim Pharma Kg | FAP-activated anti-tumour compounds |
| DE10005275A1 (de) * | 2000-02-07 | 2001-08-09 | Bayer Ag | Neuartige Glycokonjugate |
| US7220824B1 (en) * | 2000-08-28 | 2007-05-22 | Bayer Aktiengesellschaft | Integrin-mediated drug targeting |
| EP1219634A1 (en) * | 2000-12-27 | 2002-07-03 | Bayer Aktiengesellschaft | Cytostatic-glycoconjugates having specifically cleavable peptidic linking units |
| EP1238678A1 (en) * | 2001-03-08 | 2002-09-11 | Bayer Aktiengesellschaft | Enzyme-activated cytostatic conjugates with integrin ligands |
| US20050037423A1 (en) * | 2001-11-09 | 2005-02-17 | Bayer Healthcare Ag | Isotopycally coded affinity marker 2 |
| US7199149B2 (en) * | 2003-10-01 | 2007-04-03 | Bristol Myers Squibb Company | Monocyclic and bicyclic lactams as factor Xa inhibitors |
| KR100956913B1 (ko) | 2003-12-19 | 2010-05-11 | 제넨테크, 인크. | 치료제로서 유용한 일가 항체 단편 |
| PT2001862E (pt) | 2006-03-28 | 2011-07-20 | Warner Chilcott Co Llc | Sais de malato e polimorfos do ácido (3s,5s)-7-[3- amino-5-metil-piperidinil]-1-ciclopropil-1,4-dihidro- 8-metoxi-4-oxo-3-quinolinocarboxílico |
| WO2007110836A1 (en) | 2006-03-28 | 2007-10-04 | The Procter & Gamble Company | A hydride reduction process for preparing quinolone intermediates |
| BRPI0709220A2 (pt) | 2006-03-28 | 2011-07-12 | Procter & Gamble | processo de acoplamento para preparo de intermediários de quinolona |
| WO2016109880A1 (en) | 2015-01-06 | 2016-07-14 | Immunovaccine Technologies Inc. | Lipid a mimics, methods of preparation, and uses thereof |
| EP3380126A4 (en) * | 2015-11-25 | 2019-07-24 | LegoChem Biosciences, Inc. | ANTIBODY-ACTIVE CONJUGATES WITH BRANCHED LINKERS AND ASSOCIATED METHODS |
| CA3006242A1 (en) | 2015-11-25 | 2017-06-01 | Legochem Biosciences, Inc. | Conjugates comprising self-immolative groups and methods related thereto |
| AU2018246806B2 (en) | 2017-03-29 | 2022-05-12 | Ligachem Biosciences Inc. | Pyrrolobenzodiazepine dimer precursor and ligand-linker conjugate compound thereof |
| CA3099680A1 (en) | 2018-05-09 | 2019-11-14 | Legochem Biosciences, Inc. | Compositions and methods related to anti-cd19 antibody drug conjugates |
| KR20210028544A (ko) | 2019-09-04 | 2021-03-12 | 주식회사 레고켐 바이오사이언스 | 인간 ror1에 대한 항체를 포함하는 항체 약물 접합체 및 이의 용도 |
| JP7820508B2 (ja) * | 2021-10-06 | 2026-02-25 | サムヤン コーポレイション | 飽和フロジオキシン誘導体化合物及びその二次電池用添加剤としての使用 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5977356A (ja) * | 1982-06-30 | 1984-05-02 | Fuji Photo Film Co Ltd | 螢光アツセイ用多層分析要素およびそれを用いる螢光アツセイ法 |
| DE3611194A1 (de) | 1986-04-04 | 1987-10-08 | Bayer Ag | Cancerostatisches mittel |
| EP0284071B1 (en) * | 1987-03-26 | 1994-06-08 | Neorx Corporation | Metal-radionuclide-labeled proteins and glycoproteins for diagnosis and therapy |
| US4975278A (en) | 1988-02-26 | 1990-12-04 | Bristol-Myers Company | Antibody-enzyme conjugates in combination with prodrugs for the delivery of cytotoxic agents to tumor cells |
| US4980343A (en) * | 1988-10-27 | 1990-12-25 | Bayer Aktiengesellschaft | Aminooxodihydroisoindoloquinazoline carcinostatic agents |
| DE3837825A1 (de) | 1988-11-08 | 1990-05-10 | Hoechst Ag | Neue insulinderivate, ihre verwendung und eine sie enthaltende pharmazeutische zubereitung |
| CA2031803C (en) * | 1989-12-13 | 2001-05-29 | Ramakrishnan Nagarajan | Improvements in or relating to glycopeptide deriveratives |
| US5160727A (en) * | 1990-02-13 | 1992-11-03 | Warner-Lambert Company | Tumor cell sensitization method using quinazolinedione derivatives |
| US5965695A (en) | 1990-05-15 | 1999-10-12 | Chiron Corporation | Modified peptide and peptide libraries with protease resistance, derivatives thereof and methods of producing and screening such |
| US5420297A (en) | 1990-10-24 | 1995-05-30 | Fujisawa Pharmaceutical Co., Ltd. | Peptides having substance P antagonistic activity |
| US5399363A (en) * | 1991-01-25 | 1995-03-21 | Eastman Kodak Company | Surface modified anticancer nanoparticles |
| DE4106101A1 (de) * | 1991-02-27 | 1992-09-03 | Bayer Ag | Fucose-markierte cytostatika |
| US5595732A (en) * | 1991-03-25 | 1997-01-21 | Hoffmann-La Roche Inc. | Polyethylene-protein conjugates |
| FR2676058B1 (fr) | 1991-04-30 | 1994-02-25 | Hoechst Lab | Prodrogues glycosylees, leur procede de preparation et leur utilisation dans le traitement des cancers. |
| DE4120646A1 (de) | 1991-06-22 | 1992-12-24 | Bayer Ag | 7-isoindolinyl-chinolon- und naphthyridoncarbonsaeure-derivate |
| DE59209745D1 (de) | 1991-11-29 | 1999-10-21 | Hoechst Ag | Peptide mit insulinartiger Wirkung |
| SE9103612D0 (sv) | 1991-12-04 | 1991-12-04 | Astra Ab | New peptide derivatives |
| AU662434B2 (en) | 1992-08-07 | 1995-08-31 | Sankyo Company Limited | Peptides capable of inhibiting the activity of HIV protease, their preparation and their use |
| US5872207A (en) | 1992-09-04 | 1999-02-16 | Sanofi Pharmaceuticals, Inc. | N-terminal-marked peptides immobilized on glass beads and method of preparation and method of use thereof |
| IL106998A0 (en) | 1992-09-17 | 1993-12-28 | Univ Florida | Brain-enhanced delivery of neuroactive peptides by sequential metabolism |
| DE4236237A1 (de) * | 1992-10-27 | 1994-04-28 | Behringwerke Ag | Prodrugs, ihre Herstellung und Verwendung als Arzneimittel |
| US5576298A (en) | 1992-11-30 | 1996-11-19 | Research And Development Institute, Inc. At Montana State University | Peptides from pseudomonas syringae possessing broad-spectrum antibiotic activity |
| SE9300012D0 (sv) | 1993-01-05 | 1993-01-05 | Astra Ab | New peptides |
| US5750648A (en) | 1993-08-20 | 1998-05-12 | G.D. Searle & Co. | Retroviral protease inhibitors and combinations thereof |
| EP0647450A1 (en) | 1993-09-09 | 1995-04-12 | BEHRINGWERKE Aktiengesellschaft | Improved prodrugs for enzyme mediated activation |
| GB9320781D0 (en) | 1993-10-08 | 1993-12-01 | Erba Carlo Spa | Polymer-bound camptothecin derivatives |
| CA2173990A1 (en) * | 1993-10-12 | 1995-04-20 | Narasinga Rao | A library of glyco-peptides useful for identification of cell adhesion inhibitors |
| US5610145A (en) | 1994-04-15 | 1997-03-11 | Warner-Lambert Company | Tachykinin antagonists |
| US5780589A (en) | 1994-11-30 | 1998-07-14 | The United States Of America As Represented By The Department Of Health And Human Services | Ultraselective opioidmimetic peptides and pharmacological and therapeutic uses thereof |
| FR2729668A1 (fr) | 1995-01-23 | 1996-07-26 | Adir | Nouveaux derives de mercaptoalcanoyldipeptides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5677286A (en) * | 1995-04-27 | 1997-10-14 | The University Of Michigan | Glycosylated analogs of camptothecin |
| US6143931A (en) | 1997-04-16 | 2000-11-07 | Arqule, Inc. | Synthesis and use of α-ketoamide derivatives and arrays |
-
1995
- 1995-04-04 DE DE19512484A patent/DE19512484A1/de not_active Withdrawn
-
1996
- 1996-03-22 DE DE59603678T patent/DE59603678D1/de not_active Expired - Fee Related
- 1996-03-22 BR BR9604825A patent/BR9604825A/pt not_active IP Right Cessation
- 1996-03-22 CA CA002217164A patent/CA2217164A1/en not_active Abandoned
- 1996-03-22 RU RU97118421/04A patent/RU2170234C2/ru not_active IP Right Cessation
- 1996-03-22 US US08/930,546 patent/US6271342B1/en not_active Expired - Fee Related
- 1996-03-22 JP JP8529934A patent/JPH11502860A/ja not_active Ceased
- 1996-03-22 PL PL96322681A patent/PL183574B1/pl unknown
- 1996-03-22 CZ CZ19973143A patent/CZ291098B6/cs not_active IP Right Cessation
- 1996-03-22 MX MX9707613A patent/MX9707613A/es unknown
- 1996-03-22 AU AU53976/96A patent/AU713466B2/en not_active Ceased
- 1996-03-22 EE EE9700258A patent/EE03619B1/xx not_active IP Right Cessation
- 1996-03-22 UA UA97115364A patent/UA61054C2/uk unknown
- 1996-03-22 HU HU9800513A patent/HUP9800513A3/hu unknown
- 1996-03-22 NZ NZ305855A patent/NZ305855A/xx unknown
- 1996-03-22 KR KR1019970706996A patent/KR19980703591A/ko not_active Abandoned
- 1996-03-22 EP EP96910926A patent/EP0819135B1/de not_active Expired - Lifetime
- 1996-03-22 SK SK1345-97A patent/SK281785B6/sk unknown
- 1996-03-22 CN CN96194180A patent/CN1185786A/zh active Pending
- 1996-03-22 WO PCT/EP1996/001279 patent/WO1996031532A1/de not_active Ceased
- 1996-03-22 ES ES96910926T patent/ES2140078T3/es not_active Expired - Lifetime
- 1996-03-22 DK DK96910926T patent/DK0819135T3/da active
- 1996-03-22 AT AT96910926T patent/ATE186738T1/de not_active IP Right Cessation
- 1996-10-01 TW TW085111956A patent/TW384290B/zh not_active IP Right Cessation
-
1997
- 1997-09-16 BG BG101892A patent/BG63048B1/bg unknown
- 1997-09-18 IS IS4562A patent/IS1822B/is unknown
- 1997-10-02 NO NO974564A patent/NO974564L/no not_active Application Discontinuation
-
2000
- 2000-02-09 GR GR20000400304T patent/GR3032605T3/el not_active IP Right Cessation
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