ES2565238T3 - Inhibidores de la c-fms quinasa - Google Patents
Inhibidores de la c-fms quinasa Download PDFInfo
- Publication number
- ES2565238T3 ES2565238T3 ES07760840.4T ES07760840T ES2565238T3 ES 2565238 T3 ES2565238 T3 ES 2565238T3 ES 07760840 T ES07760840 T ES 07760840T ES 2565238 T3 ES2565238 T3 ES 2565238T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- phenyl
- amide
- cyano
- formula
- 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.)
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- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 239000012453 solvate Substances 0.000 claims abstract description 4
- 150000004677 hydrates Chemical class 0.000 claims description 3
- -1 oxadiazol-5-onyl Chemical group 0.000 abstract description 60
- 125000000217 alkyl group Chemical group 0.000 abstract description 28
- 229910052799 carbon Inorganic materials 0.000 abstract description 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
- 125000003386 piperidinyl group Chemical class 0.000 abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 239000000460 chlorine Substances 0.000 abstract description 3
- 125000000392 cycloalkenyl group Chemical class 0.000 abstract description 3
- 125000003831 tetrazolyl group Chemical group 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 241000689227 Cora <basidiomycete fungus> Species 0.000 abstract description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract description 2
- 125000003226 pyrazolyl group Chemical group 0.000 abstract description 2
- 125000004076 pyridyl group Chemical group 0.000 abstract description 2
- 125000000335 thiazolyl group Chemical group 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 13
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- XTDRPNJABDWQFI-UHFFFAOYSA-N 5-cyano-1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC(C#N)=CN1 XTDRPNJABDWQFI-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 210000002540 macrophage Anatomy 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BTQLZARELGWHGD-UHFFFAOYSA-N 4-[5-amino-6-(4,4-dimethylcyclohexen-1-yl)pyridin-2-yl]oxan-4-ol Chemical compound C1C(C)(C)CCC(C=2C(=CC=C(N=2)C2(O)CCOCC2)N)=C1 BTQLZARELGWHGD-UHFFFAOYSA-N 0.000 description 2
- WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 102000007651 Macrophage Colony-Stimulating Factor Human genes 0.000 description 2
- 108010046938 Macrophage Colony-Stimulating Factor Proteins 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 2
- SLPWXZZHNSOZPX-UHFFFAOYSA-N imidazole-1-carbonitrile Chemical compound N#CN1C=CN=C1 SLPWXZZHNSOZPX-UHFFFAOYSA-N 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- COSHJOZVKGAYBP-UHFFFAOYSA-N 1,2,6-trimethylpiperidine Chemical compound CC1CCCC(C)N1C COSHJOZVKGAYBP-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- NWVGXXPWOYZODV-UHFFFAOYSA-N 1h-imidazole-5-carbonitrile Chemical compound N#CC1=CN=CN1 NWVGXXPWOYZODV-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- NHGHQAPADCDVRA-UHFFFAOYSA-N 4-(4-nitrophenyl)oxane-4-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1(C#N)CCOCC1 NHGHQAPADCDVRA-UHFFFAOYSA-N 0.000 description 1
- QDVSUOHUSJPSDM-UHFFFAOYSA-N 4-[4-amino-3-(4,4-dimethylcyclohexen-1-yl)phenyl]oxan-4-ol Chemical compound C1C(C)(C)CCC(C=2C(=CC=C(C=2)C2(O)CCOCC2)N)=C1 QDVSUOHUSJPSDM-UHFFFAOYSA-N 0.000 description 1
- BHPHLSPVDNUCLJ-UHFFFAOYSA-N 4-cyano-n-[2-(4,4-dimethylcyclohexen-1-yl)-4-[4-(2-methoxyethylamino)oxan-4-yl]phenyl]-1h-pyrrole-2-carboxamide Chemical compound C=1C=C(NC(=O)C=2NC=C(C=2)C#N)C(C=2CCC(C)(C)CC=2)=CC=1C1(NCCOC)CCOCC1 BHPHLSPVDNUCLJ-UHFFFAOYSA-N 0.000 description 1
- QPKAOOFTYWSSPA-UHFFFAOYSA-N 4-cyano-n-[4-[4-[2-(dimethylamino)ethoxy]oxan-4-yl]-2-(4,4-dimethylcyclohexen-1-yl)phenyl]-1h-pyrrole-2-carboxamide Chemical compound C=1C=C(NC(=O)C=2NC=C(C=2)C#N)C(C=2CCC(C)(C)CC=2)=CC=1C1(OCCN(C)C)CCOCC1 QPKAOOFTYWSSPA-UHFFFAOYSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 description 1
- MGPMHKNMXXADPK-UHFFFAOYSA-N 5-cyano-n-[2-(4,4-dimethylcyclohexen-1-yl)-4-(4-hydroxythian-4-yl)phenyl]-1h-imidazole-2-carboxamide Chemical compound C1C(C)(C)CCC(C=2C(=CC=C(C=2)C2(O)CCSCC2)NC(=O)C=2NC=C(N=2)C#N)=C1 MGPMHKNMXXADPK-UHFFFAOYSA-N 0.000 description 1
- VLNIEYNECZYJGW-UHFFFAOYSA-N 5-cyano-n-[2-(4,4-dimethylcyclohexen-1-yl)-4-(4-piperazin-1-yloxan-4-yl)phenyl]-1h-imidazole-2-carboxamide Chemical compound C1C(C)(C)CCC(C=2C(=CC=C(C=2)C2(CCOCC2)N2CCNCC2)NC(=O)C=2NC(=CN=2)C#N)=C1 VLNIEYNECZYJGW-UHFFFAOYSA-N 0.000 description 1
- HVHBKILSSHPQSR-UHFFFAOYSA-N 5-cyano-n-[2-(4-methylpiperidin-1-yl)-4-[4-(2-pyrrolidin-1-ylethylamino)oxan-4-yl]phenyl]-1h-imidazole-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(C2(CCOCC2)NCCN2CCCC2)=CC=C1NC(=O)C1=NC=C(C#N)N1 HVHBKILSSHPQSR-UHFFFAOYSA-N 0.000 description 1
- RWZUQJAWYZZOSM-UHFFFAOYSA-N 5-cyano-n-[4-[4-(dimethylamino)oxan-4-yl]-2-(4,4-dimethylcyclohexen-1-yl)phenyl]-1h-imidazole-2-carboxamide Chemical compound C=1C=C(NC(=O)C=2NC(=CN=2)C#N)C(C=2CCC(C)(C)CC=2)=CC=1C1(N(C)C)CCOCC1 RWZUQJAWYZZOSM-UHFFFAOYSA-N 0.000 description 1
- GBFSCCJDHRIXKM-UHFFFAOYSA-N 5-cyano-n-[4-[4-[2-(dimethylamino)ethoxy]oxan-4-yl]-2-(4-methylpiperidin-1-yl)phenyl]-1h-imidazole-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(C2(CCOCC2)OCCN(C)C)=CC=C1NC(=O)C1=NC=C(C#N)N1 GBFSCCJDHRIXKM-UHFFFAOYSA-N 0.000 description 1
- GPASEBZMAVEREE-UHFFFAOYSA-N 6-bromo-2-(4,4-dimethylcyclohexen-1-yl)pyridin-3-amine Chemical compound C1C(C)(C)CCC(C=2C(=CC=C(Br)N=2)N)=C1 GPASEBZMAVEREE-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WOVKYSAHUYNSMH-UHFFFAOYSA-N BROMODEOXYURIDINE Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-UHFFFAOYSA-N 0.000 description 1
- DSZYYKWWZGGNEA-UHFFFAOYSA-N C1CC(C)CCN1C1=CC(C2(CN3CCCC3)CCOCC2)=CC=C1N Chemical compound C1CC(C)CCN1C1=CC(C2(CN3CCCC3)CCOCC2)=CC=C1N DSZYYKWWZGGNEA-UHFFFAOYSA-N 0.000 description 1
- TYIXAYWBOBTRSU-UHFFFAOYSA-N CC1(CCC(=CC1)C2=C(C=CC(=N2)C3(CCOCC3)N4CCN(CC4)C)N5C=C(N=C5C(=O)N)C#N)C Chemical compound CC1(CCC(=CC1)C2=C(C=CC(=N2)C3(CCOCC3)N4CCN(CC4)C)N5C=C(N=C5C(=O)N)C#N)C TYIXAYWBOBTRSU-UHFFFAOYSA-N 0.000 description 1
- TVNATASXJLXAGU-UHFFFAOYSA-N CC1CC(O)(CC(C)S1)c1ccc(N)c(c1)C1=CCC(C)(C)CC1 Chemical compound CC1CC(O)(CC(C)S1)c1ccc(N)c(c1)C1=CCC(C)(C)CC1 TVNATASXJLXAGU-UHFFFAOYSA-N 0.000 description 1
- OAALXXSUFXDJEM-UHFFFAOYSA-N CC1CCN(CC1)c1cc(ccc1N)C1(CCOCC1)N1CCCC1 Chemical compound CC1CCN(CC1)c1cc(ccc1N)C1(CCOCC1)N1CCCC1 OAALXXSUFXDJEM-UHFFFAOYSA-N 0.000 description 1
- FTTKEEUSQVJRLM-UHFFFAOYSA-N CC1CCN(CC1)c1cc(ccc1N)C1(CCOCC1)NCCN(C)C Chemical compound CC1CCN(CC1)c1cc(ccc1N)C1(CCOCC1)NCCN(C)C FTTKEEUSQVJRLM-UHFFFAOYSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 108010058398 Macrophage Colony-Stimulating Factor Receptor Proteins 0.000 description 1
- 101000916629 Mus musculus Macrophage colony-stimulating factor 1 Proteins 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229950004398 broxuridine Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- RGICCWARFGRNII-UHFFFAOYSA-N n-[4-[1-acetyl-4-(methylaminomethyl)piperidin-4-yl]-2-(4,4-diethylcyclohexen-1-yl)phenyl]-4-cyano-1h-pyrrole-2-carboxamide Chemical compound C1C(CC)(CC)CCC(C=2C(=CC=C(C=2)C2(CNC)CCN(CC2)C(C)=O)NC(=O)C=2NC=C(C=2)C#N)=C1 RGICCWARFGRNII-UHFFFAOYSA-N 0.000 description 1
- VJRYLBDDYOIQEY-UHFFFAOYSA-N n-[4-[4-(aminomethyl)oxan-4-yl]-2-(4,4-dimethylcyclohexen-1-yl)phenyl]-5-cyano-1h-imidazole-2-carboxamide Chemical compound C1C(C)(C)CCC(C=2C(=CC=C(C=2)C2(CN)CCOCC2)NC(=O)C=2NC=C(N=2)C#N)=C1 VJRYLBDDYOIQEY-UHFFFAOYSA-N 0.000 description 1
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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| US10106798B2 (en) | 2010-01-05 | 2018-10-23 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | FLT3 receptor antagonists for the treatment or the prevention of pain disorders |
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| EA023999B1 (ru) | 2011-05-05 | 2016-08-31 | Новартис Аг | Ингибиторы csf-1r для лечения опухолей головного мозга |
| US8940742B2 (en) * | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| JOP20180012A1 (ar) | 2012-08-07 | 2019-01-30 | Janssen Pharmaceutica Nv | عملية السلفنة باستخدام نونافلوروبوتانيسولفونيل فلوريد |
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| PH12016500582B1 (en) | 2013-10-04 | 2023-06-30 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
| SI3102576T1 (sl) * | 2014-02-03 | 2019-08-30 | Vitae Pharmaceuticals, Llc | Inhibitorji dihidropirolopiridina ROR-gama |
| JP6701088B2 (ja) | 2014-03-19 | 2020-05-27 | インフィニティー ファーマシューティカルズ, インコーポレイテッド | Pi3k−ガンマ媒介障害の治療で使用するための複素環式化合物 |
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| AU2016322552B2 (en) | 2015-09-14 | 2021-03-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
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| WO2021144360A1 (en) | 2020-01-17 | 2021-07-22 | F. Hoffmann-La Roche Ag | Small molecule csf-1r inhibitors in therapeutic and cosmetic uses |
| CN112441941B (zh) * | 2020-12-03 | 2022-08-02 | 浙江荣耀生物科技股份有限公司 | 一种1-(4-氨基苯基)环戊基甲腈的制备方法 |
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