CA2884102A1 - Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzimidazole, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met - Google Patents
Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzimidazole, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met Download PDFInfo
- Publication number
- CA2884102A1 CA2884102A1 CA2884102A CA2884102A CA2884102A1 CA 2884102 A1 CA2884102 A1 CA 2884102A1 CA 2884102 A CA2884102 A CA 2884102A CA 2884102 A CA2884102 A CA 2884102A CA 2884102 A1 CA2884102 A1 CA 2884102A1
- Authority
- CA
- Canada
- Prior art keywords
- radical
- benzothiazol
- triazolo
- phenyl
- pyridazin
- 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.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title abstract description 23
- 239000003112 inhibitor Substances 0.000 title abstract description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 23
- 239000008194 pharmaceutical composition Substances 0.000 title description 11
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
- -1 O-cycloalkyl Chemical group 0.000 claims abstract description 348
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 79
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 75
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 58
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 150000003254 radicals Chemical class 0.000 claims description 166
- 150000001875 compounds Chemical class 0.000 claims description 111
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
- 125000005843 halogen group Chemical group 0.000 claims description 37
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 19
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
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- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
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- 239000001301 oxygen Substances 0.000 claims description 3
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- 125000004122 cyclic group Chemical group 0.000 abstract 1
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- 238000001819 mass spectrum Methods 0.000 description 121
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- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 40
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- 125000001424 substituent group Chemical group 0.000 description 32
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- 150000007522 mineralic acids Chemical class 0.000 description 29
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- 238000002360 preparation method Methods 0.000 description 29
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 26
- 229940093915 gynecological organic acid Drugs 0.000 description 25
- 235000005985 organic acids Nutrition 0.000 description 25
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 25
- 210000004027 cell Anatomy 0.000 description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
- 238000011282 treatment Methods 0.000 description 24
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- 230000006870 function Effects 0.000 description 22
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- 206010028980 Neoplasm Diseases 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 19
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- FVNSRFMQXKMHTQ-UHFFFAOYSA-N (2-amino-1,3-benzothiazol-6-yl) thiocyanate Chemical compound C1=C(SC#N)C=C2SC(N)=NC2=C1 FVNSRFMQXKMHTQ-UHFFFAOYSA-N 0.000 description 17
- 238000004587 chromatography analysis Methods 0.000 description 17
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 16
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- UFYSEIRQWVNZCO-UHFFFAOYSA-N 3-chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1=CC(F)=CC=C1C1=NN2C(Cl)=NN=C2C=C1 UFYSEIRQWVNZCO-UHFFFAOYSA-N 0.000 description 14
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- ZKBFVQGSCTZQMY-UHFFFAOYSA-N phenyl n-(6-thiocyanato-1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C2=CC=C(SC#N)C=C2SC=1NC(=O)OC1=CC=CC=C1 ZKBFVQGSCTZQMY-UHFFFAOYSA-N 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- TVPRCLHSULCNLV-UHFFFAOYSA-N pyridazin-3-one Chemical compound O=C1C=CC=N[N]1 TVPRCLHSULCNLV-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-N sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonic acid Chemical class [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- PHPTXKAAGSHXDV-UHFFFAOYSA-N tert-butyl n-(6-thiocyanato-1,3-benzothiazol-2-yl)carbamate Chemical compound C1=C(SC#N)C=C2SC(NC(=O)OC(C)(C)C)=NC2=C1 PHPTXKAAGSHXDV-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
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Classifications
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- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Emergency Medicine (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0705789A FR2919870B1 (fr) | 2007-08-09 | 2007-08-09 | Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzothiazole et benzimidazole, procede, compositions pharmaceutiques et nouvelle utilisation comme inhibiteurs de cmet |
| FR0705789 | 2007-08-09 | ||
| FR0801819 | 2008-04-02 | ||
| FR0801819A FR2929613B1 (fr) | 2008-04-02 | 2008-04-02 | Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzimidazole,leur preparation,comme medicaments et utilisation notamment comme inhibiteurs de met |
| CA2695628A CA2695628C (fr) | 2007-08-09 | 2008-08-06 | Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzimidazole, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2695628A Division CA2695628C (fr) | 2007-08-09 | 2008-08-06 | Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzimidazole, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2884102A1 true CA2884102A1 (fr) | 2009-05-07 |
Family
ID=40524792
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2884102A Abandoned CA2884102A1 (fr) | 2007-08-09 | 2008-08-06 | Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzimidazole, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
| CA2695628A Expired - Fee Related CA2695628C (fr) | 2007-08-09 | 2008-08-06 | Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzimidazole, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2695628A Expired - Fee Related CA2695628C (fr) | 2007-08-09 | 2008-08-06 | Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzimidazole, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
Country Status (41)
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PA8792501A1 (es) | 2007-08-09 | 2009-04-23 | Sanofi Aventis | Nuevos derivados de 6-triazolopiridacina-sulfanil benzotiazol y bencimidazol,su procedimiento de preparación,su aplicación como medicamentos,composiciones farmacéuticas y nueva utilización principalmente como inhibidores de met. |
| FR2945806B1 (fr) * | 2009-05-19 | 2013-04-05 | Sanofi Aventis | Nouveaux derives imidazo[1,2-a]pyridine,procede de preparation,medicaments,compositions pharmaceutiques et utilisation notamment comme inhibiteurs de met |
| FR2941229B1 (fr) * | 2009-01-21 | 2012-11-30 | Sanofi Aventis | Nouveaux derives triazolo°4,3-a!pyridine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
| AU2009272517A1 (en) * | 2008-07-18 | 2010-01-21 | Sanofi-Aventis | Novel imidazo[1,2-a]pyridine derivatives, method for the preparation thereof, use thereof as medicaments, pharmaceutical compositions and novel use in particular as MET inhibitors |
| WO2010007316A2 (fr) * | 2008-07-18 | 2010-01-21 | Sanofi-Aventis | NOUVEAUX DERIVES TRIAZOLO(4,3-a)PYRIDINE,LEUR PROCEDE DE PREPARATION,LEUR APPLICATION A TITRE DE MEDICAMENTS,COMPOSITIONS PHARMACEUTIQUES ET NOUVELLE UTILISATION NOTAMMENT COMME INHIBITEURS DE MET |
| UY32049A (es) | 2008-08-14 | 2010-03-26 | Takeda Pharmaceutical | Inhibidores de cmet |
| FR2941949B1 (fr) * | 2009-02-06 | 2011-04-01 | Sanofi Aventis | Derives de 6-(6-o-cycloalkyl ou 6-nh-cycloalkyl- triazolopyridazine-sulfanyl)benzothiazoles et benzimidazoles preparation, application comme medicaments et utilisation comme inhibiteurs de met. |
| FR2941950B1 (fr) * | 2009-02-06 | 2011-04-01 | Sanofi Aventis | Derives de 6-(6-o-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met. |
| FR2941951B1 (fr) * | 2009-02-06 | 2011-04-01 | Sanofi Aventis | Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met. |
| FR2941952B1 (fr) * | 2009-02-06 | 2011-04-01 | Sanofi Aventis | Derives de 6-(6-substitue-triazolopyridazine-sulfanyl) 5-fluoro-benzothiazoles et 5-fluoro-benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met. |
| EP2396333B1 (en) * | 2009-02-10 | 2013-07-03 | AstraZeneca AB | Triazolo[4,3-b]pyridazine derivatives and their uses for prostate cancer |
| UY32623A (es) * | 2009-05-11 | 2010-12-31 | Astrazeneca Ab | Derivados bicíclicos para afecciones asociadas al receptor de andrógenos |
| MX336996B (es) | 2009-12-31 | 2016-02-09 | Hutchison Medipharma Ltd | Ciertas triazolopiridinas y triazolopirazinas, composiciones de estas y sus metodos de uso. |
| FR2958292A1 (fr) * | 2010-03-30 | 2011-10-07 | Sanofi Aventis | Derives de 6-(alkyl- ou cycloalkyl-triazolopyridazine-sulfanyl) benzothiazoles: preparation, application comme medicaments et utilisation comme inhibiteurs de met |
| TW201202242A (en) | 2010-03-30 | 2012-01-16 | Sanofi Aventis | 6-(alkyl-or cycloalkyl-triazolopyridazine-sulfanyl)benzo-thiazole derivatives: preparation, and use as medicaments and as MET inhibitors |
| FR2966151B1 (fr) * | 2010-10-14 | 2012-11-09 | Sanofi Aventis | Derives de 6-(alkyl- ou cycloalkyl-triazolopyridazine-sulfanyl) benzothiazoles: preparation, application comme medicaments et utilisation comme inhibiteurs de met |
| US20130315895A1 (en) | 2010-07-01 | 2013-11-28 | Takeda Pharmaceutical Company Limited | COMBINATION OF A cMET INHIBITOR AND AN ANTIBODY TO HGF AND/OR cMET |
| AR085183A1 (es) | 2010-07-30 | 2013-09-18 | Lilly Co Eli | Compuesto 6-(1-metil-1h-pirazol-4-il)-3-(2-metil-2h-indazol-5-iltio)-[1,2,4]triazol[4,3-b]piridazina, composicion farmaceutica que lo comprende y uso para preparar un medicamento util para tratar cancer |
| UA117092C2 (uk) | 2011-09-06 | 2018-06-25 | Байєр Інтеллектуал Проперті Гмбх | Амінозаміщені імідазопіридазини |
| JP5957526B2 (ja) | 2011-09-15 | 2016-07-27 | ノバルティス アーゲー | チロシンキナーゼとしての６−置換３−（キノリン−６−イルチオ）−［１，２，４］トリアゾロ［４，３−ａ］ピラジン |
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| FR2499995A1 (fr) | 1981-02-13 | 1982-08-20 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkylthiomethyl 7-amino thiazolylacetamido cephalosporanique, leur preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. |
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| PA8792501A1 (es) | 2007-08-09 | 2009-04-23 | Sanofi Aventis | Nuevos derivados de 6-triazolopiridacina-sulfanil benzotiazol y bencimidazol,su procedimiento de preparación,su aplicación como medicamentos,composiciones farmacéuticas y nueva utilización principalmente como inhibidores de met. |
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