TW200908981A - Triazolyl aminopyrimidine compounds - Google Patents
Triazolyl aminopyrimidine compounds Download PDFInfo
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- TW200908981A TW200908981A TW097116886A TW97116886A TW200908981A TW 200908981 A TW200908981 A TW 200908981A TW 097116886 A TW097116886 A TW 097116886A TW 97116886 A TW97116886 A TW 97116886A TW 200908981 A TW200908981 A TW 200908981A
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- Prior art keywords
- ethyl
- group
- amino
- amine
- fluoro
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- -1 Triazolyl aminopyrimidine compounds Chemical class 0.000 title claims abstract description 113
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 201000011510 cancer Diseases 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 124
- 238000002360 preparation method Methods 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000003277 amino group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000011737 fluorine Chemical group 0.000 claims description 21
- 229910052731 fluorine Chemical group 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 5
- 206010031096 Oropharyngeal cancer Diseases 0.000 claims description 5
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- 238000009833 condensation Methods 0.000 claims description 5
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- 206010014733 Endometrial cancer Diseases 0.000 claims description 4
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 4
- 208000032612 Glial tumor Diseases 0.000 claims description 4
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- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 4
- 201000010881 cervical cancer Diseases 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- DXVWRJRZCMCNEU-UHFFFAOYSA-N dimercaptoamine Chemical group SNS DXVWRJRZCMCNEU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
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- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
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- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 7
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- IRTLROCMFSDSNF-UHFFFAOYSA-N 2-phenyl-1h-pyrrole Chemical compound C1=CNC(C=2C=CC=CC=2)=C1 IRTLROCMFSDSNF-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 claims 1
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- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
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- 230000008774 maternal effect Effects 0.000 claims 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
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- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000008600 mitotic progression Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- RDNMOYZEMHOLIF-UHFFFAOYSA-N n,n-di(propan-2-yl)decan-1-amine Chemical group CCCCCCCCCCN(C(C)C)C(C)C RDNMOYZEMHOLIF-UHFFFAOYSA-N 0.000 description 1
- GASFVSRUEBGMDI-UHFFFAOYSA-N n-aminohydroxylamine Chemical group NNO GASFVSRUEBGMDI-UHFFFAOYSA-N 0.000 description 1
- 229940086322 navelbine Drugs 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 150000004689 octahydrates Chemical class 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 238000009521 phase II clinical trial Methods 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 229940080469 phosphocellulose Drugs 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- GMSYQCGRYWQGHA-UHFFFAOYSA-N prop-1-ene-2-thiol Chemical compound CC(S)=C GMSYQCGRYWQGHA-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000022983 regulation of cell cycle Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- HHOPPKOLHCBNJI-UHFFFAOYSA-N tert-butyl 2-(2-bromo-4-fluorophenyl)aziridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC1C1=CC=C(F)C=C1Br HHOPPKOLHCBNJI-UHFFFAOYSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
- AUEGGHBBWKGFRH-UHFFFAOYSA-N tert-butyl n-[1-(2-bromo-4-fluorophenyl)cyclobutyl]carbamate Chemical compound C=1C=C(F)C=C(Br)C=1C1(NC(=O)OC(C)(C)C)CCC1 AUEGGHBBWKGFRH-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- MUQNAPSBHXFMHT-UHFFFAOYSA-N tert-butylhydrazine Chemical compound CC(C)(C)NN MUQNAPSBHXFMHT-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- PYHOFAHZHOBVGV-UHFFFAOYSA-N triazane Chemical compound NNN PYHOFAHZHOBVGV-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MPMSZXWCZKCHLQ-UHFFFAOYSA-N trihydridoiodine Chemical compound [H]I([H])[H] MPMSZXWCZKCHLQ-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229940099039 velcade Drugs 0.000 description 1
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000010792 warming Methods 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- A61K31/495—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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93834707P | 2007-05-16 | 2007-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200908981A true TW200908981A (en) | 2009-03-01 |
Family
ID=39951591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097116886A TW200908981A (en) | 2007-05-16 | 2008-05-07 | Triazolyl aminopyrimidine compounds |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8063035B2 (enExample) |
| EP (1) | EP2155734A2 (enExample) |
| JP (1) | JP5248600B2 (enExample) |
| KR (1) | KR101131261B1 (enExample) |
| CN (1) | CN101679395B (enExample) |
| AR (1) | AR066473A1 (enExample) |
| AU (1) | AU2008254319B2 (enExample) |
| BR (1) | BRPI0811433A2 (enExample) |
| CA (1) | CA2691997A1 (enExample) |
| CL (1) | CL2008001323A1 (enExample) |
| EA (1) | EA016781B1 (enExample) |
| MX (1) | MX2009012228A (enExample) |
| PE (1) | PE20090216A1 (enExample) |
| TW (1) | TW200908981A (enExample) |
| WO (1) | WO2008144223A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7964729B2 (en) | 2006-08-28 | 2011-06-21 | Massachusetts Institute Of Technology | Sox-based kinase sensor |
| CA2671738A1 (en) | 2006-12-21 | 2008-06-26 | Eli Lilly And Company | Imidazolidinonyl aminopyrimidine compounds for the treatment of cancer |
| RS51526B (sr) | 2006-12-21 | 2011-06-30 | Eli Lilly & Company | Jedinjenja imidazolidinonil aminopirimidina za lečenje kancera |
| US8440835B2 (en) | 2007-02-26 | 2013-05-14 | Massachusetts Institute Of Technology | Environmentally sensitive fluorophores |
| CA2691997A1 (en) | 2007-05-16 | 2008-11-27 | Eli Lilly And Company | Triazolyl aminopyrimidine compounds |
| MX2009012233A (es) * | 2007-05-16 | 2009-12-01 | Lilly Co Eli | Compuestos de triazolil aminopirimidina. |
| KR101123178B1 (ko) * | 2009-04-09 | 2012-06-13 | (주)에스메디 | 2-아릴벤조싸이오펜 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 퇴행성 뇌질환의 진단 또는 치료용 약학적 조성물 |
| JP2013502901A (ja) * | 2009-08-25 | 2013-01-31 | オンコセラピー・サイエンス株式会社 | がんの治療および診断の標的遺伝子としてのｅｒｃｃ６ｌ |
| WO2011025546A1 (en) * | 2009-08-31 | 2011-03-03 | Massachusetts Institute Of Technology | 1, 2, 3-triazole containing protein kinase sensors |
| UA119247C2 (uk) | 2013-09-06 | 2019-05-27 | РОЙВЕНТ САЙЕНСИЗ ҐмбГ | Спіроциклічні сполуки як інгібітори триптофангідроксилази |
| US9611201B2 (en) * | 2015-03-05 | 2017-04-04 | Karos Pharmaceuticals, Inc. | Processes for preparing (R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanol and 1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanone |
| EP3475280B1 (en) * | 2016-06-23 | 2020-04-08 | H. Hoffnabb-La Roche Ag | Novel [1,2,3]triazolo[4,5-d]pyrimidine derivatives |
| WO2020068600A1 (en) * | 2018-09-24 | 2020-04-02 | Rapt Therapeutics, Inc. | Ubiquitin-specific-processing protease 7 (usp7) modulators and uses thereof |
| MY205268A (en) * | 2019-09-05 | 2024-10-10 | Univ Melbourne | Nitrification inhibitors |
| CN112341428A (zh) * | 2020-11-04 | 2021-02-09 | 菏泽鸿特药业有限公司 | 一种噻吩-2-乙胺的生产方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4929726A (en) * | 1988-02-09 | 1990-05-29 | Georgia State University Foundation, Inc. | Novel diazines and their method of preparation |
| WO2004063192A1 (en) | 2003-01-10 | 2004-07-29 | Pharmacopeia Drug Discovery, Inc. | Imidazolyl pyrimidine derivatives useful as il-8 receptor modulators |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| EP1651629A1 (en) * | 2003-07-31 | 2006-05-03 | Boehringer Ingelheim Pharmaceuticals Inc. | Substituted benzothiophene compounds and uses thereof |
| JP4932735B2 (ja) | 2004-12-17 | 2012-05-16 | アムジエン・インコーポレーテツド | アミノピリミジン化合物および使用方法 |
| TW200800201A (en) | 2005-11-18 | 2008-01-01 | Lilly Co Eli | Pyrimidinyl benzothiophene compounds |
| WO2007117465A2 (en) | 2006-03-31 | 2007-10-18 | Abbott Laboratories | Indazole compounds |
| RS51526B (sr) * | 2006-12-21 | 2011-06-30 | Eli Lilly & Company | Jedinjenja imidazolidinonil aminopirimidina za lečenje kancera |
| CA2671738A1 (en) | 2006-12-21 | 2008-06-26 | Eli Lilly And Company | Imidazolidinonyl aminopyrimidine compounds for the treatment of cancer |
| CA2691997A1 (en) | 2007-05-16 | 2008-11-27 | Eli Lilly And Company | Triazolyl aminopyrimidine compounds |
| MX2009012233A (es) * | 2007-05-16 | 2009-12-01 | Lilly Co Eli | Compuestos de triazolil aminopirimidina. |
-
2008
- 2008-05-07 CA CA002691997A patent/CA2691997A1/en not_active Abandoned
- 2008-05-07 EP EP08747731A patent/EP2155734A2/en not_active Withdrawn
- 2008-05-07 PE PE2008000798A patent/PE20090216A1/es not_active Application Discontinuation
- 2008-05-07 AU AU2008254319A patent/AU2008254319B2/en not_active Ceased
- 2008-05-07 WO PCT/US2008/062808 patent/WO2008144223A2/en not_active Ceased
- 2008-05-07 BR BRPI0811433A patent/BRPI0811433A2/pt not_active IP Right Cessation
- 2008-05-07 KR KR1020097023340A patent/KR101131261B1/ko not_active Expired - Fee Related
- 2008-05-07 TW TW097116886A patent/TW200908981A/zh unknown
- 2008-05-07 EA EA200971068A patent/EA016781B1/ru not_active IP Right Cessation
- 2008-05-07 JP JP2010508500A patent/JP5248600B2/ja not_active Expired - Fee Related
- 2008-05-07 AR ARP080101932A patent/AR066473A1/es unknown
- 2008-05-07 CL CL2008001323A patent/CL2008001323A1/es unknown
- 2008-05-07 CN CN2008800157689A patent/CN101679395B/zh not_active Expired - Fee Related
- 2008-05-07 US US12/598,926 patent/US8063035B2/en not_active Expired - Fee Related
- 2008-05-07 MX MX2009012228A patent/MX2009012228A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| US20100087431A1 (en) | 2010-04-08 |
| EA200971068A1 (ru) | 2010-04-30 |
| CA2691997A1 (en) | 2008-11-27 |
| CN101679395B (zh) | 2012-06-13 |
| AU2008254319B2 (en) | 2012-04-19 |
| WO2008144223A3 (en) | 2009-02-05 |
| BRPI0811433A2 (pt) | 2016-03-22 |
| KR20090130242A (ko) | 2009-12-21 |
| MX2009012228A (es) | 2009-12-01 |
| EA016781B1 (ru) | 2012-07-30 |
| JP5248600B2 (ja) | 2013-07-31 |
| CL2008001323A1 (es) | 2009-05-29 |
| PE20090216A1 (es) | 2009-02-28 |
| WO2008144223A2 (en) | 2008-11-27 |
| CN101679395A (zh) | 2010-03-24 |
| KR101131261B1 (ko) | 2012-04-24 |
| AU2008254319A1 (en) | 2008-11-27 |
| EP2155734A2 (en) | 2010-02-24 |
| US8063035B2 (en) | 2011-11-22 |
| JP2010527365A (ja) | 2010-08-12 |
| AR066473A1 (es) | 2009-08-19 |
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