BRPI0906359A2 - derivados de diazepinopirimidona heteroarilamida substituída - Google Patents
derivados de diazepinopirimidona heteroarilamida substituída Download PDFInfo
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- BRPI0906359A2 BRPI0906359A2 BRPI0906359A BRPI0906359A BRPI0906359A2 BR PI0906359 A2 BRPI0906359 A2 BR PI0906359A2 BR PI0906359 A BRPI0906359 A BR PI0906359A BR PI0906359 A BRPI0906359 A BR PI0906359A BR PI0906359 A2 BRPI0906359 A2 BR PI0906359A2
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- Brazil
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- oxo
- hexahydro
- triaza
- pyrimidin
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- XQSNXLDLKOJJOU-UHFFFAOYSA-N pyrimido[5,4-c]diazepin-3-one Chemical class N1=NC(=O)C=CC2=NC=NC=C21 XQSNXLDLKOJJOU-UHFFFAOYSA-N 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000008318 pyrimidones Chemical class 0.000 claims abstract description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000003112 inhibitor Substances 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 15
- 239000012453 solvate Substances 0.000 claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 4
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 49
- -1 [1,5] naphthyridine-2-carbonyl Chemical group 0.000 claims description 16
- 230000003449 preventive effect Effects 0.000 claims description 9
- 125000004494 ethyl ester group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- VVXJWAJHMIUWKJ-UHFFFAOYSA-N 10-amino-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-d][1,4]diazepin-4-one Chemical compound NC1CNCCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 VVXJWAJHMIUWKJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
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- 239000000126 substance Substances 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000014674 injury Diseases 0.000 claims 3
- MGWVZYUSEMDHFJ-UHFFFAOYSA-N 10-amino-2-pyridin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-d][1,4]diazepin-4-one Chemical compound NC1CNCCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 MGWVZYUSEMDHFJ-UHFFFAOYSA-N 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004754 (C2-C12) dialkylamino group Chemical group 0.000 claims 1
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical group C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- MQXQLPMYDXMFQO-UHFFFAOYSA-N 10-amino-8-methyl-2-pyrimidin-4-yl-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepin-4-one Chemical compound NC1CN(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 MQXQLPMYDXMFQO-UHFFFAOYSA-N 0.000 claims 1
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
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- 210000004556 brain Anatomy 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
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- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 claims 1
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- 201000004792 malaria Diseases 0.000 claims 1
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- 201000000585 muscular atrophy Diseases 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
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- 235000020824 obesity Nutrition 0.000 claims 1
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 1
- 208000027232 peripheral nervous system disease Diseases 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 210000000278 spinal cord Anatomy 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 230000008736 traumatic injury Effects 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 description 12
- 102100038104 Glycogen synthase kinase-3 beta Human genes 0.000 description 12
- 239000012458 free base Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000026731 phosphorylation Effects 0.000 description 3
- 238000006366 phosphorylation reaction Methods 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 229910052801 chlorine Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007901 soft capsule Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 102000013498 tau Proteins Human genes 0.000 description 2
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- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 150000002367 halogens Chemical class 0.000 description 1
- 230000006951 hyperphosphorylation Effects 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
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- 229940080428 lactose 200 mg Drugs 0.000 description 1
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- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
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- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08290076A EP2090579A1 (en) | 2008-01-29 | 2008-01-29 | Substituted heteroarylamide diazepinopyrimidone derivatives |
| PCT/IB2009/000397 WO2009095792A2 (en) | 2008-01-29 | 2009-01-27 | Substituted heteroarylamide diazepinopyrimidone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0906359A2 true BRPI0906359A2 (pt) | 2019-08-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0906359A BRPI0906359A2 (pt) | 2008-01-29 | 2009-01-27 | derivados de diazepinopirimidona heteroarilamida substituída |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8507475B2 (enExample) |
| EP (2) | EP2090579A1 (enExample) |
| JP (1) | JP5611837B2 (enExample) |
| KR (1) | KR20100117583A (enExample) |
| CN (1) | CN101986782A (enExample) |
| AR (1) | AR070273A1 (enExample) |
| AU (1) | AU2009208731A1 (enExample) |
| BR (1) | BRPI0906359A2 (enExample) |
| CA (1) | CA2713289A1 (enExample) |
| EA (1) | EA201070891A1 (enExample) |
| IL (1) | IL207192A0 (enExample) |
| MX (1) | MX2010008362A (enExample) |
| NZ (1) | NZ587068A (enExample) |
| TW (1) | TW200936588A (enExample) |
| WO (1) | WO2009095792A2 (enExample) |
| ZA (1) | ZA201005382B (enExample) |
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| EP2085399A1 (en) * | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | substituted arylamide oxazepinopyrimidone derivatives |
| EP2085400A1 (en) * | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | Substituted heteroarylamide oxazepinopyrimidone derivatives |
| EP2090578A1 (en) * | 2008-01-29 | 2009-08-19 | Sanofi-Aventis | Substituted arylamide diazepinopyrimidone derivatives for the treatment of neurodegenerative diseases caused by abnormal activity of GSK3-beta |
| EP2138494A1 (en) * | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted alkyl pyrimidin-4-one derivatives |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| PE20181893A1 (es) * | 2016-02-15 | 2018-12-11 | Sanofi Sa | Nuevos compuestos de 6,7-dihidro-5h-benzo[7]anuleno sustituidos, procesos para su preparacion y usos terapeuticos de los mismos |
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| EG13192A (en) | 1976-02-10 | 1982-12-31 | Rhone Poulenc Ind | Nouveaux derives du dithiole-1,2 leur preparation et les compositions qui les contiennent |
| US5629322A (en) | 1994-11-15 | 1997-05-13 | Merck & Co., Inc. | Cyclic amidine analogs as inhibitors of nitric oxide synthase |
| JP3188715B2 (ja) | 1995-11-01 | 2001-07-16 | メルク エンド カンパニー インコーポレーテッド | 一酸化窒素シンターゼの阻害物質としてのヘキサヒドロ−５−イミノ−１，４−ヘテロアゼピン誘導体 |
| US20030096813A1 (en) * | 2001-04-20 | 2003-05-22 | Jingrong Cao | Compositions useful as inhibitors of GSK-3 |
| CN1247586C (zh) * | 2001-09-21 | 2006-03-29 | 赛诺菲安万特 | 治疗神经退化性疾病的取代的2－嘧啶基－6,7,8,9－四氢嘧啶并[1,2－a]嘧啶－4－酮及7－嘧啶基－2,3－二氢咪唑并[1,2－a]嘧啶－5(1h)酮衍生物 |
| EP1557417B1 (en) * | 2003-12-19 | 2007-03-07 | Sanofi-Aventis | Substituted 8'-pyri(mi)dinyl-dihydrospiro-[cycloalkylamine]-pyrimido[1,2-a] pyrimidin-6-one derivatives |
| EP1790649A1 (en) * | 2005-11-21 | 2007-05-30 | Sanofi-Aventis | Substituted bicyclic pyrimidone derivatives |
| EP2085399A1 (en) * | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | substituted arylamide oxazepinopyrimidone derivatives |
| EP2085400A1 (en) * | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | Substituted heteroarylamide oxazepinopyrimidone derivatives |
| EP2090578A1 (en) * | 2008-01-29 | 2009-08-19 | Sanofi-Aventis | Substituted arylamide diazepinopyrimidone derivatives for the treatment of neurodegenerative diseases caused by abnormal activity of GSK3-beta |
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2008
- 2008-01-29 EP EP08290076A patent/EP2090579A1/en not_active Withdrawn
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2009
- 2009-01-23 TW TW098103040A patent/TW200936588A/zh unknown
- 2009-01-27 EA EA201070891A patent/EA201070891A1/ru unknown
- 2009-01-27 EP EP09705869.7A patent/EP2238140B1/en active Active
- 2009-01-27 MX MX2010008362A patent/MX2010008362A/es not_active Application Discontinuation
- 2009-01-27 JP JP2010544816A patent/JP5611837B2/ja not_active Expired - Fee Related
- 2009-01-27 KR KR1020107016905A patent/KR20100117583A/ko not_active Withdrawn
- 2009-01-27 WO PCT/IB2009/000397 patent/WO2009095792A2/en not_active Ceased
- 2009-01-27 CN CN2009801106975A patent/CN101986782A/zh active Pending
- 2009-01-27 AU AU2009208731A patent/AU2009208731A1/en not_active Abandoned
- 2009-01-27 CA CA2713289A patent/CA2713289A1/en not_active Abandoned
- 2009-01-27 BR BRPI0906359A patent/BRPI0906359A2/pt not_active IP Right Cessation
- 2009-01-27 NZ NZ587068A patent/NZ587068A/en not_active IP Right Cessation
- 2009-01-28 AR ARP090100256A patent/AR070273A1/es unknown
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2010
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- 2010-07-27 US US12/844,273 patent/US8507475B2/en not_active Expired - Fee Related
- 2010-07-28 ZA ZA2010/05382A patent/ZA201005382B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR070273A1 (es) | 2010-03-25 |
| AU2009208731A1 (en) | 2009-08-06 |
| KR20100117583A (ko) | 2010-11-03 |
| CA2713289A1 (en) | 2009-08-06 |
| WO2009095792A3 (en) | 2009-10-08 |
| IL207192A0 (en) | 2010-12-30 |
| EP2238140A2 (en) | 2010-10-13 |
| EP2090579A1 (en) | 2009-08-19 |
| JP2011510972A (ja) | 2011-04-07 |
| NZ587068A (en) | 2011-12-22 |
| EP2238140B1 (en) | 2013-07-17 |
| TW200936588A (en) | 2009-09-01 |
| US20110015187A1 (en) | 2011-01-20 |
| CN101986782A (zh) | 2011-03-16 |
| ZA201005382B (en) | 2011-10-26 |
| EA201070891A1 (ru) | 2011-02-28 |
| JP5611837B2 (ja) | 2014-10-22 |
| WO2009095792A2 (en) | 2009-08-06 |
| US8507475B2 (en) | 2013-08-13 |
| MX2010008362A (es) | 2010-08-30 |
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