NO311252B1 - Forbindelser med colchicinstruktur, deres anvendelse, fremstilling av legemidler og blandinger som inneholder dem - Google Patents
Forbindelser med colchicinstruktur, deres anvendelse, fremstilling av legemidler og blandinger som inneholder dem Download PDFInfo
- Publication number
- NO311252B1 NO311252B1 NO19985676A NO985676A NO311252B1 NO 311252 B1 NO311252 B1 NO 311252B1 NO 19985676 A NO19985676 A NO 19985676A NO 985676 A NO985676 A NO 985676A NO 311252 B1 NO311252 B1 NO 311252B1
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- NO
- Norway
- Prior art keywords
- compound according
- compounds
- preparation
- compound
- mixture
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- 239000000203 mixture Substances 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 11
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical group C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 title abstract description 18
- 229940079593 drug Drugs 0.000 title description 5
- 239000003814 drug Substances 0.000 title description 5
- NUNCOHUMTCDISK-AWEZNQCLSA-N (7s)-7-amino-1,2,3-trimethoxy-10-methylsulfanyl-6,7-dihydro-5h-benzo[a]heptalen-9-one Chemical compound C1([C@@H](N)CC2)=CC(=O)C(SC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC NUNCOHUMTCDISK-AWEZNQCLSA-N 0.000 claims description 6
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- HFPMXDMZJUJZBX-AWEZNQCLSA-N Deacetylcolchicine Chemical compound C1([C@@H](N)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC HFPMXDMZJUJZBX-AWEZNQCLSA-N 0.000 claims description 4
- HFPMXDMZJUJZBX-UHFFFAOYSA-N N-deacetylcolchicine Natural products C1CC(N)C2=CC(=O)C(OC)=CC=C2C2=C1C=C(OC)C(OC)=C2OC HFPMXDMZJUJZBX-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- NOUZOVBGCDDMSX-UHFFFAOYSA-N 3,5-ditert-butylcyclohexa-3,5-diene-1,2-dione Chemical compound CC(C)(C)C1=CC(=O)C(=O)C(C(C)(C)C)=C1 NOUZOVBGCDDMSX-UHFFFAOYSA-N 0.000 claims description 3
- DRNGPPYFUCOXLW-UHFFFAOYSA-M 4-methylbenzenesulfonate;1-methylpyridin-1-ium-4-carbaldehyde Chemical compound C[N+]1=CC=C(C=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 DRNGPPYFUCOXLW-UHFFFAOYSA-M 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 2
- 230000002456 anti-arthritic effect Effects 0.000 claims description 2
- 230000001028 anti-proliverative effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000008389 polyethoxylated castor oil Substances 0.000 claims description 2
- 229920000136 polysorbate Polymers 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 1
- 229950008882 polysorbate Drugs 0.000 claims 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 229960001338 colchicine Drugs 0.000 abstract description 6
- CMEGANPVAXDBPL-INIZCTEOSA-N n-[(7s)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical class C1([C@@H](NC(C)=O)CC2)=CC(=O)C(SC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC CMEGANPVAXDBPL-INIZCTEOSA-N 0.000 abstract description 5
- 206010028980 Neoplasm Diseases 0.000 abstract description 2
- 230000002634 anti-blastic effect Effects 0.000 abstract description 2
- 201000011510 cancer Diseases 0.000 abstract description 2
- 238000007306 functionalization reaction Methods 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229940045695 antineooplastic colchicine derivative Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 thiocolchicoside Chemical class 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
- LMBIHYWAZRMYEM-UHFFFAOYSA-N 1,2,3-trimethoxy-10-methylsulfanyl-5,6-dihydrobenzo[a]heptalene-7,9-dione Chemical compound C1CC(=O)C2=CC(=O)C(SC)=CC=C2C2=C1C=C(OC)C(OC)=C2OC LMBIHYWAZRMYEM-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- NNJPGOLRFBJNIW-UHFFFAOYSA-N Demecolcine Natural products C1=C(OC)C(=O)C=C2C(NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-UHFFFAOYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- LEQAKWQJCITZNK-AXHKHJLKSA-N N-[(7S)-1,2-dimethoxy-10-(methylthio)-9-oxo-3-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CCC2=C3)=CC(=O)C(SC)=CC=C1C2=C(OC)C(OC)=C3O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LEQAKWQJCITZNK-AXHKHJLKSA-N 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 208000006111 contracture Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 229960005052 demecolcine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 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
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930001910 pseudoalkaloid Natural products 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960000287 thiocolchicoside Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
-
- 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
- A61K31/12—Ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
-
- 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
- C07H15/24—Condensed ring systems having three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/34—Benzoheptalenes; Hydrogenated benzoheptalenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Physical Education & Sports Medicine (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (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 Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI001168A IT1283110B1 (it) | 1996-06-07 | 1996-06-07 | Composti a scheletro colchicinico,loro uso come farmaci e composizioni che li contengono |
| PCT/EP1997/002577 WO1997047577A1 (fr) | 1996-06-07 | 1997-05-21 | Composes a squelette de colchicine, leur utilisation comme medicaments et compositions les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO985676D0 NO985676D0 (no) | 1998-12-04 |
| NO985676L NO985676L (no) | 1998-12-04 |
| NO311252B1 true NO311252B1 (no) | 2001-11-05 |
Family
ID=11374396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19985676A NO311252B1 (no) | 1996-06-07 | 1998-12-04 | Forbindelser med colchicinstruktur, deres anvendelse, fremstilling av legemidler og blandinger som inneholder dem |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6080739A (fr) |
| EP (1) | EP0906262B1 (fr) |
| JP (1) | JP3285361B2 (fr) |
| KR (1) | KR100306430B1 (fr) |
| CN (1) | CN1122657C (fr) |
| AT (1) | ATE222228T1 (fr) |
| AU (1) | AU723752B2 (fr) |
| CZ (1) | CZ294365B6 (fr) |
| DE (1) | DE69714735T2 (fr) |
| DK (1) | DK0906262T3 (fr) |
| ES (1) | ES2182084T3 (fr) |
| HK (1) | HK1019587A1 (fr) |
| HU (1) | HUP0001827A3 (fr) |
| IT (1) | IT1283110B1 (fr) |
| NO (1) | NO311252B1 (fr) |
| PL (1) | PL187528B1 (fr) |
| PT (1) | PT906262E (fr) |
| RU (1) | RU2181354C2 (fr) |
| SK (2) | SK283736B6 (fr) |
| WO (1) | WO1997047577A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9714249D0 (en) * | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| FR2774290B1 (fr) * | 1998-02-05 | 2000-06-16 | Synthelabo | Composition pharmaceutique pour l'administration par voie nasale de thiocolchicoside |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| IT1318401B1 (it) * | 2000-03-17 | 2003-08-25 | Indena Spa | Derivati di n-desacetiltiocolchicina e composizioni farmaceutiche cheli contengono. |
| US6720323B2 (en) | 2000-07-07 | 2004-04-13 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| US6825236B2 (en) | 2003-04-14 | 2004-11-30 | California Pacific Medical Center | Colchicine derivatives |
| ITMI20040164A1 (it) * | 2004-02-03 | 2004-05-03 | Indena Spa | Derivati di n.deacetiltiocolchicina loro uso e formulazioni farmaceutiche che li contengono |
| WO2006066419A1 (fr) * | 2004-12-22 | 2006-06-29 | Mestex Ag | Melange contenant un agoniste des recepteurs vanilloides et une substance inhibant la regeneration des nerfs, utilisation de ce melange pour produire un analgesique et procede d'application de cet analgesique |
| ITRM20070088A1 (it) | 2007-02-19 | 2008-08-20 | Francesco Fringuelli | Composti derivati della colchicina, procedimento per la loro preparazione e usi in campo medico. |
| US20110178180A1 (en) * | 2010-01-18 | 2011-07-21 | Kurt Nielsen | Deuterium-enriched colchicine, thiocolchicine, and derivatives thereof; methods of preparation; and use thereof |
| US8927760B2 (en) | 2010-02-18 | 2015-01-06 | The Asan Foundation | Colchicine derivatives or pharmaceutically acceptable salts thereof, method for preparing said derivatives, and pharmaceutical composition comprising said derivatives |
| KR101130754B1 (ko) | 2010-06-25 | 2012-03-28 | 제일약품주식회사 | 난용성 트리사이클릭 유도체 화합물의 용해도가 향상된 약학적 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL279678A (fr) * | 1961-06-14 | |||
| FR3032M (fr) * | 1963-06-19 | 1964-12-28 | Roussel Uclaf | Nouveaux médicaments doués notamment d'activité antimitotique. |
| US3442953A (en) * | 1963-06-19 | 1969-05-06 | Roussel Uclaf | Novel 7-oxo-7-desacetylaminocolchicine compounds |
| US4349548A (en) * | 1981-11-20 | 1982-09-14 | Merck & Co., Inc. | Octahydrobenzo[6,7]cyclohept[1,2-b]-1,4-oxazines, compositions and use |
-
1996
- 1996-06-07 IT IT96MI001168A patent/IT1283110B1/it active IP Right Grant
-
1997
- 1997-05-21 WO PCT/EP1997/002577 patent/WO1997047577A1/fr active IP Right Grant
- 1997-05-21 PL PL97330284A patent/PL187528B1/pl not_active IP Right Cessation
- 1997-05-21 RU RU99100326/04A patent/RU2181354C2/ru not_active IP Right Cessation
- 1997-05-21 US US09/180,875 patent/US6080739A/en not_active Expired - Fee Related
- 1997-05-21 PT PT97924965T patent/PT906262E/pt unknown
- 1997-05-21 AT AT97924965T patent/ATE222228T1/de not_active IP Right Cessation
- 1997-05-21 ES ES97924965T patent/ES2182084T3/es not_active Expired - Lifetime
- 1997-05-21 CN CN97194988A patent/CN1122657C/zh not_active Expired - Fee Related
- 1997-05-21 HU HU0001827A patent/HUP0001827A3/hu unknown
- 1997-05-21 EP EP97924965A patent/EP0906262B1/fr not_active Expired - Lifetime
- 1997-05-21 DK DK97924965T patent/DK0906262T3/da active
- 1997-05-21 KR KR1019980709961A patent/KR100306430B1/ko not_active IP Right Cessation
- 1997-05-21 JP JP50110898A patent/JP3285361B2/ja not_active Expired - Fee Related
- 1997-05-21 CZ CZ19984010A patent/CZ294365B6/cs not_active IP Right Cessation
- 1997-05-21 AU AU30278/97A patent/AU723752B2/en not_active Ceased
- 1997-05-21 SK SK1679-98A patent/SK283736B6/sk not_active IP Right Cessation
- 1997-05-21 SK SK41-2003A patent/SK283737B6/sk not_active IP Right Cessation
- 1997-05-21 DE DE69714735T patent/DE69714735T2/de not_active Expired - Lifetime
-
1998
- 1998-12-04 NO NO19985676A patent/NO311252B1/no not_active IP Right Cessation
-
1999
- 1999-10-27 HK HK99104798A patent/HK1019587A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK1019587A1 (en) | 2000-02-18 |
| EP0906262A1 (fr) | 1999-04-07 |
| CZ401098A3 (cs) | 1999-05-12 |
| SK283737B6 (sk) | 2003-12-02 |
| CN1219924A (zh) | 1999-06-16 |
| AU3027897A (en) | 1998-01-07 |
| WO1997047577A1 (fr) | 1997-12-18 |
| NO985676D0 (no) | 1998-12-04 |
| NO985676L (no) | 1998-12-04 |
| DE69714735D1 (de) | 2002-09-19 |
| ITMI961168A0 (it) | 1996-06-07 |
| IT1283110B1 (it) | 1998-04-07 |
| PL330284A1 (en) | 1999-05-10 |
| CZ294365B6 (cs) | 2004-12-15 |
| JP2000503669A (ja) | 2000-03-28 |
| RU2181354C2 (ru) | 2002-04-20 |
| AU723752B2 (en) | 2000-09-07 |
| JP3285361B2 (ja) | 2002-05-27 |
| EP0906262B1 (fr) | 2002-08-14 |
| PL187528B1 (pl) | 2004-07-30 |
| KR100306430B1 (ko) | 2001-11-30 |
| ATE222228T1 (de) | 2002-08-15 |
| ES2182084T3 (es) | 2003-03-01 |
| ITMI961168A1 (it) | 1997-12-07 |
| US6080739A (en) | 2000-06-27 |
| HUP0001827A2 (hu) | 2001-05-28 |
| SK283736B6 (sk) | 2003-12-02 |
| HUP0001827A3 (en) | 2001-07-30 |
| KR20000016387A (ko) | 2000-03-25 |
| CN1122657C (zh) | 2003-10-01 |
| DE69714735T2 (de) | 2003-04-24 |
| SK167998A3 (en) | 1999-07-12 |
| DK0906262T3 (da) | 2002-12-16 |
| PT906262E (pt) | 2002-11-29 |
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