AU2009276420A1 - Piperidine derivatives as JAK3 inhibitors - Google Patents
Piperidine derivatives as JAK3 inhibitors Download PDFInfo
- Publication number
- AU2009276420A1 AU2009276420A1 AU2009276420A AU2009276420A AU2009276420A1 AU 2009276420 A1 AU2009276420 A1 AU 2009276420A1 AU 2009276420 A AU2009276420 A AU 2009276420A AU 2009276420 A AU2009276420 A AU 2009276420A AU 2009276420 A1 AU2009276420 A1 AU 2009276420A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- formula
- heteroaryl
- aryl
- mmol
- 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
- 229940123241 Janus kinase 3 inhibitor Drugs 0.000 title 1
- 150000003053 piperidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 135
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 230000004913 activation Effects 0.000 claims description 11
- 230000001575 pathological effect Effects 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000000069 prophylactic effect Effects 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 230000002489 hematologic effect Effects 0.000 claims description 2
- 230000036210 malignancy Effects 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
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- 101100001671 Emericella variicolor andF gene Proteins 0.000 claims 1
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- 230000001629 suppression Effects 0.000 claims 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 238000001914 filtration Methods 0.000 description 19
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- 238000004128 high performance liquid chromatography Methods 0.000 description 18
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
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- 239000000725 suspension Substances 0.000 description 12
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- OZLIBRFWDOSHRS-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-cyanoacetate Chemical compound N#CCC(=O)ON1C(=O)CCC1=O OZLIBRFWDOSHRS-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 10
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- 239000007821 HATU Substances 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- XRIARWQZLGCQDM-KOLCDFICSA-N n-methyl-n-[(3r,4r)-4-methylpiperidin-3-yl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C[C@@H]1CCNC[C@@H]1N(C)C1=NC=NC2=C1C=CN2 XRIARWQZLGCQDM-KOLCDFICSA-N 0.000 description 8
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- ONTLBVKRDUFQFP-UHFFFAOYSA-N 4-chloropyrrolo[2,1-f][1,2,4]triazine Chemical compound ClC1=NC=NN2C=CC=C12 ONTLBVKRDUFQFP-UHFFFAOYSA-N 0.000 description 7
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- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- JKTHBYNKZDJPQV-OLZOCXBDSA-N tert-butyl (3r,4r)-4-methyl-3-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]piperidine-1-carboxylate Chemical compound C[C@@H]1CCN(C(=O)OC(C)(C)C)C[C@@H]1N(C)C(=O)OC(C)(C)C JKTHBYNKZDJPQV-OLZOCXBDSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
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- NVKDDQBZODSEIN-UHFFFAOYSA-N 1-benzyl-n,4-dimethylpiperidin-3-amine Chemical compound C1CC(C)C(NC)CN1CC1=CC=CC=C1 NVKDDQBZODSEIN-UHFFFAOYSA-N 0.000 description 4
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- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
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- 229940075582 sorbic acid Drugs 0.000 description 1
- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
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- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
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- 235000012431 wafers Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8570508P | 2008-08-01 | 2008-08-01 | |
| US61/085,705 | 2008-08-01 | ||
| US9856208P | 2008-09-19 | 2008-09-19 | |
| US61/098,562 | 2008-09-19 | ||
| PCT/US2009/052449 WO2010014930A2 (en) | 2008-08-01 | 2009-07-31 | Therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2009276420A1 true AU2009276420A1 (en) | 2010-02-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009276420A Abandoned AU2009276420A1 (en) | 2008-08-01 | 2009-07-31 | Piperidine derivatives as JAK3 inhibitors |
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| Country | Link |
|---|---|
| US (1) | US20110165183A1 (enExample) |
| EP (1) | EP2324020A2 (enExample) |
| JP (1) | JP2011529918A (enExample) |
| KR (1) | KR20110050654A (enExample) |
| CN (1) | CN102171211A (enExample) |
| AU (1) | AU2009276420A1 (enExample) |
| BR (1) | BRPI0916931A2 (enExample) |
| CA (1) | CA2732628A1 (enExample) |
| IL (1) | IL210990A0 (enExample) |
| MX (1) | MX2011001259A (enExample) |
| NZ (1) | NZ590922A (enExample) |
| RU (1) | RU2011105768A (enExample) |
| WO (1) | WO2010014930A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2459562A1 (en) | 2009-07-31 | 2012-06-06 | Biocryst Pharmaceuticals, Inc. | Pyrrolo [1, 2-b]pyridazine derivatives as janus kinase inhibitors |
| KR20130083389A (ko) * | 2010-05-28 | 2013-07-22 | 바이오크리스트파마슈티컬즈,인코포레이티드 | 야누스 키나아제 억제제로서 헤테로사이클릭 화합물 |
| AU2012255792A1 (en) * | 2011-05-17 | 2013-11-07 | Principia Biopharma Inc. | Azaindole derivatives as tyrosine kinase inhibitors |
| JP2015512891A (ja) | 2012-03-13 | 2015-04-30 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 殺菌性ピリミジン化合物 |
| AU2013312296B2 (en) | 2012-09-10 | 2017-06-22 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
| US9550785B2 (en) * | 2012-11-20 | 2017-01-24 | Glaxosmithkline Llc | Pyrrolopyrimidines as therapeutic agents for the treatment of diseases |
| US9481679B2 (en) * | 2012-12-17 | 2016-11-01 | Sun Pharmaceutical Industries Limited | Process for the preparation of tofacitinib and intermediates thereof |
| US9670160B2 (en) | 2012-12-28 | 2017-06-06 | Glenmark Pharmaceuticals Limited | Process for the preparation of tofacitinib and intermediates thereof |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| EP3046915A1 (en) | 2013-09-16 | 2016-07-27 | Basf Se | Fungicidal pyrimidine compounds |
| KR20160092991A (ko) * | 2013-09-27 | 2016-08-05 | 님버스 아이리스 인코포레이티드 | Irak 억제제 및 이의 용도 |
| US9951012B2 (en) * | 2013-12-09 | 2018-04-24 | Unichem Laboratories Limited | Process for the preparation of (3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine |
| KR20160117614A (ko) | 2014-02-21 | 2016-10-10 | 프린시피아 바이오파마, 인코퍼레이티드 | Btk 억제제의 염 및 고체 형태 |
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| GB201617758D0 (en) | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| JP7710223B2 (ja) | 2018-04-16 | 2025-07-18 | 深▲チェン▼市塔吉瑞生物医薬有限公司 | 置換ピロロトリアジン系化合物およびその医薬組成物並びにそれらの使用 |
| EP4045051A1 (en) | 2019-10-14 | 2022-08-24 | Principia Biopharma Inc. | Methods for treating immune thrombocytopenia by administering (r)-2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| PH12022551787A1 (en) | 2020-01-22 | 2024-02-12 | Principia Biopharma Inc | Crystalline forms of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)-1h-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
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| TW505646B (en) * | 1998-06-19 | 2002-10-11 | Pfizer Prod Inc | Pyrrolo [2,3-d] pyrimidine compounds |
| PT1382339E (pt) * | 1999-12-10 | 2008-02-06 | Pfizer Prod Inc | Composições que contêm derivados de pirrolo[2,3-d]- pirimidina |
| PL359563A1 (pl) * | 2000-06-26 | 2004-08-23 | Pfizer Products Inc. | Związki pirolo [2,3-d] pirymidynowe jako środki immunosupresyjne |
| US7301023B2 (en) * | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| WO2004047843A1 (en) * | 2002-11-26 | 2004-06-10 | Pfizer Products Inc. | Method of treatment of transplant rejection |
| EP1620437B1 (en) * | 2003-04-29 | 2009-06-17 | Pfizer Limited | 5,7-diaminopyrazolo¬4,3-d pyrimidines useful in the traetment of hypertension |
| CA2545192A1 (en) * | 2003-11-25 | 2005-06-09 | Pfizer Products Inc. | Method of treatment of atherosclerosis |
| AR054416A1 (es) * | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| KR20080026654A (ko) * | 2005-07-14 | 2008-03-25 | 아스텔라스세이야쿠 가부시키가이샤 | 헤테로시클릭 야누스 키나제 3 억제제 |
| NL2000291C2 (nl) * | 2005-11-10 | 2009-02-17 | Pfizer Prod Inc | 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H- pyrazool(4,3-d)pyrimidine-5-yl)piperidine-4-carbonzuur en zouten daarvan. |
| TW201111385A (en) * | 2009-08-27 | 2011-04-01 | Biocryst Pharm Inc | Heterocyclic compounds as janus kinase inhibitors |
| BR112013008240A2 (pt) * | 2010-10-08 | 2017-12-12 | Abbvie Inc | compostos de furo [3-2-d] pirimidina |
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- 2009-07-31 AU AU2009276420A patent/AU2009276420A1/en not_active Abandoned
- 2009-07-31 BR BRPI0916931A patent/BRPI0916931A2/pt not_active IP Right Cessation
- 2009-07-31 JP JP2011521361A patent/JP2011529918A/ja active Pending
- 2009-07-31 RU RU2011105768/04A patent/RU2011105768A/ru not_active Application Discontinuation
- 2009-07-31 CA CA2732628A patent/CA2732628A1/en not_active Abandoned
- 2009-07-31 MX MX2011001259A patent/MX2011001259A/es unknown
- 2009-07-31 KR KR1020117004724A patent/KR20110050654A/ko not_active Withdrawn
- 2009-07-31 WO PCT/US2009/052449 patent/WO2010014930A2/en not_active Ceased
- 2009-07-31 EP EP09791064A patent/EP2324020A2/en not_active Withdrawn
- 2009-07-31 US US13/057,100 patent/US20110165183A1/en not_active Abandoned
- 2009-07-31 NZ NZ590922A patent/NZ590922A/xx not_active IP Right Cessation
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2011
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| MX2011001259A (es) | 2011-03-15 |
| EP2324020A2 (en) | 2011-05-25 |
| RU2011105768A (ru) | 2012-09-10 |
| CA2732628A1 (en) | 2010-02-04 |
| CN102171211A (zh) | 2011-08-31 |
| KR20110050654A (ko) | 2011-05-16 |
| WO2010014930A2 (en) | 2010-02-04 |
| WO2010014930A3 (en) | 2010-07-29 |
| BRPI0916931A2 (pt) | 2015-11-24 |
| NZ590922A (en) | 2012-09-28 |
| IL210990A0 (en) | 2011-04-28 |
| JP2011529918A (ja) | 2011-12-15 |
| US20110165183A1 (en) | 2011-07-07 |
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