IL200603A - Hedgehog path inhibitors - Google Patents
Hedgehog path inhibitorsInfo
- Publication number
- IL200603A IL200603A IL200603A IL20060309A IL200603A IL 200603 A IL200603 A IL 200603A IL 200603 A IL200603 A IL 200603A IL 20060309 A IL20060309 A IL 20060309A IL 200603 A IL200603 A IL 200603A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- alkyl
- optionally
- solvate
- Prior art date
Links
- 230000037361 pathway Effects 0.000 title claims description 26
- 239000003112 inhibitor Substances 0.000 title description 4
- 241000289669 Erinaceus europaeus Species 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 778
- 125000000217 alkyl group Chemical group 0.000 claims description 537
- -1 -NR23C(0)R23a Chemical group 0.000 claims description 315
- 229910052739 hydrogen Inorganic materials 0.000 claims description 298
- 239000001257 hydrogen Substances 0.000 claims description 294
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 247
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 206
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 203
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 162
- 125000001072 heteroaryl group Chemical group 0.000 claims description 161
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 142
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 128
- 150000003839 salts Chemical class 0.000 claims description 109
- 239000012453 solvate Substances 0.000 claims description 91
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 80
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 73
- 125000003545 alkoxy group Chemical group 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 68
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 65
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 61
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 57
- 206010028980 Neoplasm Diseases 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 50
- 125000001188 haloalkyl group Chemical group 0.000 claims description 46
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 43
- 125000003282 alkyl amino group Chemical group 0.000 claims description 39
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 39
- 201000011510 cancer Diseases 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 32
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 32
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 32
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 30
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 29
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 25
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 24
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 17
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 17
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 16
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 12
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 11
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 208000034578 Multiple myelomas Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 102000004169 proteins and genes Human genes 0.000 claims description 6
- 206010004146 Basal cell carcinoma Diseases 0.000 claims description 5
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- 239000003814 drug Substances 0.000 claims description 5
- 206010027191 meningioma Diseases 0.000 claims description 5
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- 208000000172 Medulloblastoma Diseases 0.000 claims description 4
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- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 4
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 4
- 201000004101 esophageal cancer Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 208000020790 biliary tract neoplasm Diseases 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 3
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 3
- 206010017758 gastric cancer Diseases 0.000 claims description 3
- 208000005017 glioblastoma Diseases 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 210000004498 neuroglial cell Anatomy 0.000 claims description 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
- 201000011549 stomach cancer Diseases 0.000 claims description 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
- BDBSUESQZJUWIW-UHFFFAOYSA-N 4-[(4-cyclopropylquinazolin-2-yl)amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C2CC2)=C(C=CC=C2)C2=N1 BDBSUESQZJUWIW-UHFFFAOYSA-N 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 230000002062 proliferating effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- LIBYVTUKKMUDQG-UHFFFAOYSA-N 4-[(4-cyclohexylquinazolin-2-yl)amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C2CCCCC2)=C(C=CC=C2)C2=N1 LIBYVTUKKMUDQG-UHFFFAOYSA-N 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 241000027355 Ferocactus setispinus Species 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 201000009036 biliary tract cancer Diseases 0.000 claims 1
- 201000008275 breast carcinoma Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- NNUMAPVWRCYJDV-UHFFFAOYSA-N n-[3-[(dimethylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC1=CC=CC(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 NNUMAPVWRCYJDV-UHFFFAOYSA-N 0.000 claims 1
- MXCYPBOMBCPTNK-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 MXCYPBOMBCPTNK-UHFFFAOYSA-N 0.000 claims 1
- WJVKMAVLTKOVCZ-UHFFFAOYSA-N n-[5-[[2-(dimethylamino)acetyl]amino]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC(=O)NC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 WJVKMAVLTKOVCZ-UHFFFAOYSA-N 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 281
- 238000005481 NMR spectroscopy Methods 0.000 description 213
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 198
- 239000000543 intermediate Substances 0.000 description 112
- 125000005843 halogen group Chemical group 0.000 description 96
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 56
- 239000002904 solvent Substances 0.000 description 55
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
- 239000007787 solid Substances 0.000 description 42
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- 125000003118 aryl group Chemical group 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- 229910052740 iodine Inorganic materials 0.000 description 25
- 125000004076 pyridyl group Chemical group 0.000 description 25
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 125000004438 haloalkoxy group Chemical group 0.000 description 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 17
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 17
- 230000002829 reductive effect Effects 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US96261707P | 2007-07-30 | 2007-07-30 | |
| PCT/US2008/056883 WO2008112913A1 (en) | 2007-03-14 | 2008-03-13 | Inhibitors of the hedgehog pathway |
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| IL200603A0 IL200603A0 (en) | 2010-05-17 |
| IL200603A true IL200603A (en) | 2014-08-31 |
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| ATE514695T1 (de) * | 2006-09-15 | 2011-07-15 | Pfizer Prod Inc | Pyrido(2,3-d)pyrimidinonverbindungen und ihre verwendung als pi3-inhibitoren |
| TWI433674B (zh) | 2006-12-28 | 2014-04-11 | Infinity Discovery Inc | 環杷明（ｃｙｃｌｏｐａｍｉｎｅ）類似物類 |
| NZ579480A (en) | 2007-03-14 | 2012-03-30 | Exelixis Patent Co Llc | 2-Arylamino-quinazoline derivatives |
| WO2009010455A2 (en) * | 2007-07-13 | 2009-01-22 | Addex Pharma S.A. | Pyrazole derivatives as modulators of metabotropic glutamate receptors |
| JP5639895B2 (ja) | 2007-12-27 | 2014-12-10 | インフィニティ ファーマスーティカルズ、インク． | 立体選択的還元方法 |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| GEP20125664B (en) * | 2008-02-26 | 2012-10-10 | Takeda Pharmaceuticals Co | Condensed heterocyclic derivatives and application thereof |
| US9265734B2 (en) | 2008-09-03 | 2016-02-23 | Biomarin Pharmaceutical Inc. | Compositions including 6-aminohexanoic acid derivatives as HDAC inhibitors |
| WO2010144586A1 (en) * | 2009-06-09 | 2010-12-16 | Abraxis Bioscience, Llc | Isoquinoline, quinoline, and quinazoline derivatives as inhibitors of hedgehog signaling |
| WO2010144909A1 (en) | 2009-06-12 | 2010-12-16 | Novartis Ag | Fused heterocyclic compounds and their uses |
| JP6141015B2 (ja) | 2009-08-05 | 2017-06-07 | インフィニティ ファーマスーティカルズ、インク． | シクロパミン類似体の酵素によるアミノ基転移 |
| ES2577024T3 (es) * | 2009-08-25 | 2016-07-12 | Abraxis Bioscience, Llc | Terapia combinada con composiciones de nanopartículas de taxano e inhibidores de Hedgehog |
| WO2011090738A2 (en) | 2009-12-29 | 2011-07-28 | Dana-Farber Cancer Institute, Inc. | Type ii raf kinase inhibitors |
| ES2593256T3 (es) | 2010-05-21 | 2016-12-07 | Infinity Pharmaceuticals, Inc. | Compuestos químicos, composiciones y métodos para las modulaciones de cinasas |
| CA2801778C (en) * | 2010-06-07 | 2018-06-05 | Novomedix, Llc | Furanyl compounds and the use thereof |
| ES2579942T3 (es) * | 2010-09-01 | 2016-08-17 | Ambit Biosciences Corporation | Pirazolilaminoquinazolina ópticamente activa y composiciones farmacéuticas y métodos de uso de la misma |
| US9394313B2 (en) | 2010-09-14 | 2016-07-19 | Infinity Pharmaceuticals, Inc. | Transfer hydrogenation of cyclopamine analogs |
| AU2011326427B2 (en) | 2010-11-10 | 2016-01-07 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| EP2663309B1 (en) | 2011-01-10 | 2017-03-15 | Infinity Pharmaceuticals, Inc. | Processes for preparing isoquinolinones and solid forms of isoquinolinones |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| ES2712803T3 (es) | 2011-02-28 | 2019-05-14 | Biomarin Pharm Inc | Inhibidores de histona desacetilasa |
| HK1198475A1 (en) | 2011-07-19 | 2015-05-08 | 无限药品股份有限公司 | Heterocyclic compounds and uses thereof |
| EP2734520B1 (en) | 2011-07-19 | 2016-09-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN103974955B (zh) | 2011-08-23 | 2018-06-19 | 阿萨纳生物科技有限责任公司 | 嘧啶并-哒嗪酮化合物及其用途 |
| US8785470B2 (en) | 2011-08-29 | 2014-07-22 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2013043255A1 (en) * | 2011-09-21 | 2013-03-28 | University Of South Alabama | Methods and compositions for the treatment of ovarian cancer |
| US9630979B2 (en) | 2011-09-29 | 2017-04-25 | Infinity Pharmaceuticals, Inc. | Inhibitors of monoacylglycerol lipase and methods of their use |
| EP3569598A1 (en) | 2011-11-17 | 2019-11-20 | Dana Farber Cancer Institute, Inc. | Inhibitors of c-jun-n-terminal kinase (jnk) |
| CA2864085C (en) * | 2012-02-08 | 2021-11-23 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
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| LT2914296T (lt) | 2012-11-01 | 2018-09-25 | Infinity Pharmaceuticals, Inc. | Vėžio gydymas, panaudojant p13 kinazės izoformos moduliatorius |
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| US9844541B2 (en) | 2012-11-29 | 2017-12-19 | Strasspharma, Llc | Methods of modulating follicle stimulating hormone activity |
| CN103040824B (zh) * | 2013-01-17 | 2015-05-27 | 四川大学 | 信号通路抑制剂及其制备方法和用途 |
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| CO6231031A2 (es) | 2010-12-20 |
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| EA018441B1 (ru) | 2013-08-30 |
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