NO310875B1 - Kolkisinderivater, anvendelse derav og sammensetninger inneholdende slike - Google Patents

Kolkisinderivater, anvendelse derav og sammensetninger inneholdende slike Download PDF

Info

Publication number: NO310875B1
Authority: NO; Norway
Prior art keywords: deacetyl; thiocolchicine; colchicine; pentafluoro; propionyl
Prior art date: 1995-06-27

Application number

NO19976001A

Other languages

English (en)

Norwegian (no)

Other versions

NO976001L (no

NO976001D0 (no

Inventor

Ezio Bombardelli

Bruno Gabetta

Original Assignee

Indena Spa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-06-27

Filing date

1997-12-19

Publication date

2001-09-10

1997-12-19 Application filed by Indena Spa filed Critical Indena Spa

1997-12-19 Publication of NO976001L publication Critical patent/NO976001L/no

1997-12-19 Publication of NO976001D0 publication Critical patent/NO976001D0/no

2001-09-10 Publication of NO310875B1 publication Critical patent/NO310875B1/no

Links

239000000203 mixture Substances 0.000 title claims description 10
IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical class 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 19
229940045695 antineooplastic colchicine derivative Drugs 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 13
230000000118 anti-neoplastic effect Effects 0.000 claims abstract description 6
230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 4
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
230000001028 anti-proliverative effect Effects 0.000 claims abstract description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 3
241000972773 Aulopiformes Species 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000003158 myorelaxant agent Substances 0.000 claims description 2
239000003921 oil Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229920000136 polysorbate Polymers 0.000 claims description 2
229940068965 polysorbates Drugs 0.000 claims description 2
235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 2
235000019515 salmon Nutrition 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 2
239000000969 carrier Substances 0.000 claims 1
239000002502 liposome Substances 0.000 claims 1
229960001338 colchicine Drugs 0.000 abstract description 8
-1 colchicine nitrogen amides Chemical class 0.000 abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
230000003013 cytotoxicity Effects 0.000 abstract description 3
231100000135 cytotoxicity Toxicity 0.000 abstract description 3
238000001990 intravenous administration Methods 0.000 abstract description 3
125000003118 aryl group Chemical group 0.000 abstract description 2
239000003795 chemical substances by application Substances 0.000 abstract description 2
210000003205 muscle Anatomy 0.000 abstract description 2
230000002040 relaxant effect Effects 0.000 abstract description 2
210000004027 cell Anatomy 0.000 abstract 1
238000001212 derivatisation Methods 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
238000011200 topical administration Methods 0.000 abstract 1
MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical group OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 abstract 1
210000004881 tumor cell Anatomy 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
239000002253 acid Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XETRHNFRKCNWAJ-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropanoate Chemical compound FC(F)(F)C(F)(F)C(=O)OC(=O)C(F)(F)C(F)(F)F XETRHNFRKCNWAJ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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 3
238000006243 chemical reaction Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
CMEGANPVAXDBPL-INIZCTEOSA-N n-[(7s)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(SC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC CMEGANPVAXDBPL-INIZCTEOSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
229960000287 thiocolchicoside Drugs 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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 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
150000007513 acids Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
230000002634 anti-blastic effect Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000000034 method Methods 0.000 description 2
229930014626 natural product Natural products 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
230000007170 pathology Effects 0.000 description 2
150000003904 phospholipids Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 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
125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
XNHUZSZMXSLTQL-UHFFFAOYSA-N 1-bromocyclopentene Chemical compound BrC1=CCCC1 XNHUZSZMXSLTQL-UHFFFAOYSA-N 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 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
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000002927 anti-mitotic effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000032823 cell division Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
208000006111 contracture Diseases 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
229960005052 demecolcine Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000006343 heptafluoro propyl group Chemical group 0.000 description 1
UFFSXJKVKBQEHC-UHFFFAOYSA-N heptafluorobutyric anhydride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(=O)OC(=O)C(F)(F)C(F)(F)C(F)(F)F UFFSXJKVKBQEHC-UHFFFAOYSA-N 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
230000003463 hyperproliferative effect Effects 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000000394 mitotic effect Effects 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
229930001910 pseudoalkaloid Natural products 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
210000002027 skeletal muscle Anatomy 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
231100001274 therapeutic index Toxicity 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RQIDQEBURXNDKG-MDZDMXLPSA-N ximenic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCCCCCC(O)=O RQIDQEBURXNDKG-MDZDMXLPSA-N 0.000 description 1

Classifications

- 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
- C07H15/248—Colchicine radicals, e.g. colchicosides
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/32—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
- 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
- C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
- 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)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Pain & Pain Management (AREA)
Biochemistry (AREA)
Physical Education & Sports Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Neurology (AREA)
Epidemiology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO19976001A 1995-06-27 1997-12-19 Kolkisinderivater, anvendelse derav og sammensetninger inneholdende slike NO310875B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT95MI001367A IT1276996B1 (it)	1995-06-27	1995-06-27	Derivati della colchicina, loro uso e formulazioni che li contengono
PCT/EP1996/002718 WO1997001570A1 (fr)	1995-06-27	1996-06-21	Derives de colchicine, leur utilisation et formulations contenant ces derives

Publications (3)

Publication Number	Publication Date
NO976001L NO976001L (no)	1997-12-19
NO976001D0 NO976001D0 (no)	1997-12-19
NO310875B1 true NO310875B1 (no)	2001-09-10

Family

ID=11371873

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19976001A NO310875B1 (no)	1995-06-27	1997-12-19	Kolkisinderivater, anvendelse derav og sammensetninger inneholdende slike

Country Status (18)

Country	Link
US (1)	US5880160A (fr)
EP (1)	EP0840738B1 (fr)
JP (1)	JP3130050B2 (fr)
KR (1)	KR100379991B1 (fr)
CN (1)	CN1091446C (fr)
AT (1)	ATE212033T1 (fr)
AU (1)	AU717082B2 (fr)
CA (1)	CA2225284C (fr)
DE (1)	DE69618600T2 (fr)
DK (1)	DK0840738T3 (fr)
ES (1)	ES2171691T3 (fr)
HU (1)	HU223103B1 (fr)
IT (1)	IT1276996B1 (fr)
NO (1)	NO310875B1 (fr)
PL (1)	PL186770B1 (fr)
PT (1)	PT840738E (fr)
RU (1)	RU2163241C2 (fr)
WO (1)	WO1997001570A1 (fr)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2759587B1 (fr) *	1997-02-20	1999-03-19	Synthelabo	Composition pharmaceutique pour l'administration buccale de thiocolchicoside
IT1291550B1 (it) *	1997-04-11	1999-01-11	Indena Spa	Derivati della colchicina e della tiocolchicina ad attivita' antinfiammatoria e miorilassante
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
US6399093B1 (en)	1999-05-19	2002-06-04	Advanced Medical Instruments	Method and composition to treat musculoskeletal disorders
IT1318401B1 (it) *	2000-03-17	2003-08-25	Indena Spa	Derivati di n-desacetiltiocolchicina e composizioni farmaceutiche cheli contengono.
JP2004502766A (ja) *	2000-07-07	2004-01-29	アンギオジェン・ファーマシューティカルズ・リミテッド	血管損傷剤としてのコルヒノール誘導体
US6624317B1 (en)	2000-09-25	2003-09-23	The University Of North Carolina At Chapel Hill	Taxoid conjugates as antimitotic and antitumor agents
US7119229B2 (en) *	2001-05-28	2006-10-10	Chemtech Research Incorporation	Alkaloid derivative and a pharmaceutical composition containing the same
US6825236B2 (en) *	2003-04-14	2004-11-30	California Pacific Medical Center	Colchicine derivatives
ITMI20031144A1 (it) *	2003-06-06	2004-12-07	Indena Spa	Analoghi del colchicoside.
ES2358801T3 (es) *	2003-06-25	2011-05-13	Je Il Pharmaceutical Co., Ltd.	Derivados tricíclicos o sales farmacéuticamente aceptables de los mismos, sus preparaciones y composiciones farmacéuticas que los contienen.
CN100341422C (zh) *	2003-11-03	2007-10-10	李精华	降低鲜黄花菜中秋水仙碱含量的方法
ITMI20040164A1 (it) *	2004-02-03	2004-05-03	Indena Spa	Derivati di n.deacetiltiocolchicina loro uso e formulazioni farmaceutiche che li contengono
TR200708925A1 (tr) *	2007-12-26	2009-07-21	Sanovel İlaç Sanayi̇ Ve Ti̇caret Anoni̇m Şi̇rketi̇	Kontrollü salım sağlayan flurbiprofen ve kas gevşetici kombinasyonları
WO2010138670A2 (fr) *	2009-05-27	2010-12-02	Mutual Pharmaceutical Company, Inc.	Dérivés de la thiocolchicine, leur procédé de fabrication et leurs procédés d'utilisation
CA2808277C (fr)	2009-08-26	2018-01-16	National Research Council Of Canada	Nouveaux derives de colchicine, leurs procedes et utilisations
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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
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US5426224A (en) *	1993-03-18	1995-06-20	The University Of North Carolina At Chapel Hill	Mammalian DNA topoisomerase II inhibitor and method

1995
- 1995-06-27 IT IT95MI001367A patent/IT1276996B1/it active IP Right Grant
1996
- 1996-06-21 DE DE69618600T patent/DE69618600T2/de not_active Expired - Fee Related
- 1996-06-21 JP JP09504160A patent/JP3130050B2/ja not_active Expired - Fee Related
- 1996-06-21 EP EP96923889A patent/EP0840738B1/fr not_active Expired - Lifetime
- 1996-06-21 WO PCT/EP1996/002718 patent/WO1997001570A1/fr not_active Ceased
- 1996-06-21 CA CA002225284A patent/CA2225284C/fr not_active Expired - Fee Related
- 1996-06-21 DK DK96923889T patent/DK0840738T3/da active
- 1996-06-21 HU HU9901685A patent/HU223103B1/hu not_active IP Right Cessation
- 1996-06-21 CN CN96194868A patent/CN1091446C/zh not_active Expired - Fee Related
- 1996-06-21 RU RU98101248/04A patent/RU2163241C2/ru not_active IP Right Cessation
- 1996-06-21 AT AT96923889T patent/ATE212033T1/de not_active IP Right Cessation
- 1996-06-21 KR KR1019970709528A patent/KR100379991B1/ko not_active Expired - Fee Related
- 1996-06-21 PL PL96324621A patent/PL186770B1/pl not_active IP Right Cessation
- 1996-06-21 AU AU64146/96A patent/AU717082B2/en not_active Ceased
- 1996-06-21 ES ES96923889T patent/ES2171691T3/es not_active Expired - Lifetime
- 1996-06-21 PT PT96923889T patent/PT840738E/pt unknown
- 1996-06-27 US US08/670,878 patent/US5880160A/en not_active Expired - Fee Related
1997
- 1997-12-19 NO NO19976001A patent/NO310875B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
ITMI951367A0 (it)	1995-06-27
PT840738E (pt)	2002-05-31
US5880160A (en)	1999-03-09
AU6414696A (en)	1997-01-30
ITMI951367A1 (it)	1996-12-27
CN1091446C (zh)	2002-09-25
IT1276996B1 (it)	1997-11-04
DK0840738T3 (da)	2002-05-06
KR100379991B1 (ko)	2003-07-22
RU2163241C2 (ru)	2001-02-20
KR19990028217A (ko)	1999-04-15
PL324621A1 (en)	1998-06-08
PL186770B1 (pl)	2004-02-27
CN1188482A (zh)	1998-07-22
HU223103B1 (hu)	2004-03-29
ATE212033T1 (de)	2002-02-15
WO1997001570A1 (fr)	1997-01-16
NO976001L (no)	1997-12-19
AU717082B2 (en)	2000-03-16
HUP9901685A2 (hu)	1999-09-28
CA2225284A1 (fr)	1997-01-16
DE69618600D1 (de)	2002-02-21
JP3130050B2 (ja)	2001-01-31
EP0840738B1 (fr)	2002-01-16
HUP9901685A3 (en)	2001-07-30
DE69618600T2 (de)	2002-08-08
EP0840738A1 (fr)	1998-05-13
JPH11501324A (ja)	1999-02-02
CA2225284C (fr)	2006-12-12
NO976001D0 (no)	1997-12-19
ES2171691T3 (es)	2002-09-16
HK1009138A1 (en)	1999-05-28

Publication	Publication Date	Title
NO310875B1 (no)	2001-09-10	Kolkisinderivater, anvendelse derav og sammensetninger inneholdende slike
EP0235796A2 (fr)	1987-09-09	Dérivés de dibenzo[b,e]oxépine et agent anti-allergique et anti-inflammatoire
DE69510212T2 (de)	1999-11-11	Colchicin-derivate sowie ihre therapeutische verwendung
WO2007082475A1 (fr)	2007-07-26	Nouveau composé diterpène ent-kaurène et ses dérivés, leur préparation et leur utilisation
EP0580812A1 (fr)	1994-02-02	Agents antitumoraux et antipsoriasiques
NO311252B1 (no)	2001-11-05	Forbindelser med colchicinstruktur, deres anvendelse, fremstilling av legemidler og blandinger som inneholder dem
AU616717B2 (en)	1991-11-07	Epipodophyllotoxin glucoside 4'-acylderivative
EP0356137B1 (fr)	1994-10-26	Carbonates de la 3-deméthylthiocolchicine et des analogues N-acylés
HK1009138B (en)	2002-08-09	Colchicine derivatives, the use thereof and formulations containing them
AU699789B2 (en)	1998-12-17	Colchicine derivatives and the therapeutical use thereof
AU646163C (en)	1994-10-06	Anti-tumor and anti-psoriatic agents
CN1303855A (zh)	2001-07-18	具有抗肿瘤活性的4－β－碳取代－4－脱氧－4'－去甲表鬼臼毒素衍生物及合成方法
EP2493885B1 (fr)	2013-12-18	Molecules polyketides comme agents anticancereux
GB2159518A (en)	1985-12-04	New anthracyclines and process for manufacture
CA2044211A1 (fr)	1992-12-11	Analogues de l'etoposide

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