CA2360353A1 - 2-amino-6-anilino-purines and their use as medicaments - Google Patents
2-amino-6-anilino-purines and their use as medicaments Download PDFInfo
- Publication number
- CA2360353A1 CA2360353A1 CA002360353A CA2360353A CA2360353A1 CA 2360353 A1 CA2360353 A1 CA 2360353A1 CA 002360353 A CA002360353 A CA 002360353A CA 2360353 A CA2360353 A CA 2360353A CA 2360353 A1 CA2360353 A1 CA 2360353A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- phenyl
- ethyl
- hydroxy
- purin
- 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
- AWRCGEJILTVONY-UHFFFAOYSA-N 6-n-phenyl-7h-purine-2,6-diamine Chemical class C=12NC=NC2=NC(N)=NC=1NC1=CC=CC=C1 AWRCGEJILTVONY-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000003814 drug Substances 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 183
- 150000001875 compounds Chemical class 0.000 claims abstract description 137
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 67
- 238000011282 treatment Methods 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 7
- -1 alkenylene radical Chemical class 0.000 claims description 733
- 125000004432 carbon atom Chemical group C* 0.000 claims description 144
- 125000003282 alkyl amino group Chemical group 0.000 claims description 139
- 150000003254 radicals Chemical class 0.000 claims description 125
- 125000003545 alkoxy group Chemical group 0.000 claims description 122
- 239000001257 hydrogen Substances 0.000 claims description 115
- 229910052739 hydrogen Inorganic materials 0.000 claims description 115
- 229910052736 halogen Inorganic materials 0.000 claims description 108
- 150000002367 halogens Chemical group 0.000 claims description 108
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 64
- 150000002431 hydrogen Chemical group 0.000 claims description 54
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 43
- 239000001301 oxygen Substances 0.000 claims description 43
- 125000002837 carbocyclic group Chemical group 0.000 claims description 41
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 39
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 125000006239 protecting group Chemical group 0.000 claims description 34
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 32
- 239000011593 sulfur Substances 0.000 claims description 32
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 125000001931 aliphatic group Chemical group 0.000 claims description 30
- 125000000524 functional group Chemical group 0.000 claims description 30
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 241001465754 Metazoa Species 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000002757 morpholinyl group Chemical group 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 8
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 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 description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- VGHLDDJBYCJADF-UHFFFAOYSA-N 3-imidazol-1-ylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(N2C=NC=C2)=C1 VGHLDDJBYCJADF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- OQFFETNLCFWASU-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[3-[[2-[(4-hydroxycyclohexyl)amino]-9-propan-2-ylpurin-6-yl]amino]phenyl]prop-2-ynamide Chemical compound N1=C(NC2CCC(O)CC2)N=C2N(C(C)C)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=C(Cl)C=C1 OQFFETNLCFWASU-UHFFFAOYSA-N 0.000 claims 1
- KWGZFEMFDMJZMV-AFARHQOCSA-N C1=CC(C(=O)OCCC)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC Chemical compound C1=CC(C(=O)OCCC)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC KWGZFEMFDMJZMV-AFARHQOCSA-N 0.000 claims 1
- IWUAVZILMFRURF-WGSAOQKQSA-N C1=CC(S(=O)(=O)N(C)CCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC Chemical compound C1=CC(S(=O)(=O)N(C)CCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC IWUAVZILMFRURF-WGSAOQKQSA-N 0.000 claims 1
- YNWWDOPNYNXVDI-HZCBDIJESA-N C1=CC(S(=O)(=O)N(C)CCCCCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC Chemical compound C1=CC(S(=O)(=O)N(C)CCCCCCC)=CC=C1NC1=NC(N[C@@H]2CC[C@@H](O)CC2)=NC2=C1N=CN2CC YNWWDOPNYNXVDI-HZCBDIJESA-N 0.000 claims 1
- MZJCAFYBUFJTJE-YHBQERECSA-N C=1C=C(NC=2C=3N=CN(CC)C=3N=C(N[C@@H]3CC[C@@H](O)CC3)N=2)C=CC=1S(=O)(=O)N(CC)CC1=CC=CC=C1 Chemical compound C=1C=C(NC=2C=3N=CN(CC)C=3N=C(N[C@@H]3CC[C@@H](O)CC3)N=2)C=CC=1S(=O)(=O)N(CC)CC1=CC=CC=C1 MZJCAFYBUFJTJE-YHBQERECSA-N 0.000 claims 1
- VOFPDTKEQBRCLJ-KESTWPANSA-N N1=C(N[C@@H]2CC[C@@H](N)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(C)C1=CC=CC=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](N)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(C)C1=CC=CC=C1 VOFPDTKEQBRCLJ-KESTWPANSA-N 0.000 claims 1
- CBGRKQBWRIOZRW-IRJFHVNHSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=C(Cl)C=CC=C1Cl Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=C(Cl)C=CC=C1Cl CBGRKQBWRIOZRW-IRJFHVNHSA-N 0.000 claims 1
- XDQRMPMOBUFTCK-RZFKFIIISA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC(C)=CC=C1C Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC(C)=CC=C1C XDQRMPMOBUFTCK-RZFKFIIISA-N 0.000 claims 1
- QPFYQTIUHLNNSI-SAIGFBBZSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=C(C)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=1)=CC=CC=1NC(=O)C#CC1=CC=C(C)C=C1 QPFYQTIUHLNNSI-SAIGFBBZSA-N 0.000 claims 1
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- OWLAEBDRXPOHSH-XUTJKUGGSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(C)C1=CC=C(OC)C=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(C)C1=CC=C(OC)C=C1 OWLAEBDRXPOHSH-XUTJKUGGSA-N 0.000 claims 1
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- UJCLKVQTAVFRCE-DUYHBEBVSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC(C=C1)=CC=C1S(=O)(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 UJCLKVQTAVFRCE-DUYHBEBVSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- 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
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9903762.4 | 1999-02-18 | ||
| GBGB9903762.4A GB9903762D0 (en) | 1999-02-18 | 1999-02-18 | Organic compounds |
| PCT/EP2000/001271 WO2000049018A1 (en) | 1999-02-18 | 2000-02-16 | 2-amino-6-anilino-purines and their use as medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2360353A1 true CA2360353A1 (en) | 2000-08-24 |
Family
ID=10848053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002360353A Abandoned CA2360353A1 (en) | 1999-02-18 | 2000-02-16 | 2-amino-6-anilino-purines and their use as medicaments |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6767906B2 (https=) |
| EP (1) | EP1153024B1 (https=) |
| JP (1) | JP2002537300A (https=) |
| CN (1) | CN1183133C (https=) |
| AT (1) | ATE265456T1 (https=) |
| AU (1) | AU3804500A (https=) |
| BR (1) | BR0008365A (https=) |
| CA (1) | CA2360353A1 (https=) |
| DE (1) | DE60010234T2 (https=) |
| ES (1) | ES2219326T3 (https=) |
| GB (1) | GB9903762D0 (https=) |
| PT (1) | PT1153024E (https=) |
| WO (1) | WO2000049018A1 (https=) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7296896A (en) * | 1995-11-01 | 1997-05-22 | Novartis Ag | Purine derivatives and processes for their preparation |
| US6790958B2 (en) * | 1996-08-02 | 2004-09-14 | Robert T. Lum | Purine inhibitors of cyclin dependent kinase 2 & IKBA |
| WO1998016528A1 (en) * | 1996-10-11 | 1998-04-23 | Chiron Corporation | Purine inhibitors of glycogen synthase kinase 3 (gsk3) |
| US6632820B1 (en) | 1998-08-29 | 2003-10-14 | Astrazeneca Ab | Pyrimidine compounds |
| ATE342892T1 (de) | 1998-08-29 | 2006-11-15 | Astrazeneca Ab | Pyrimidine verbindungen |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| GB9907658D0 (en) | 1999-04-06 | 1999-05-26 | Zeneca Ltd | Chemical compounds |
| FR2793794B1 (fr) * | 1999-05-21 | 2001-07-27 | Hoechst Marion Roussel Inc | Nouveaux derives de la purine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation |
| GB9918035D0 (en) * | 1999-07-30 | 1999-09-29 | Novartis Ag | Organic compounds |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| JP2003531111A (ja) * | 1999-12-17 | 2003-10-21 | アライアッド・ファーマシューティカルズ・インコーポレーテッド | プロトンポンプインヒビター |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004888D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004886D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0007371D0 (en) | 2000-03-28 | 2000-05-17 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0016877D0 (en) | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
| GB0021726D0 (en) | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| FR2818642B1 (fr) | 2000-12-26 | 2005-07-15 | Hoechst Marion Roussel Inc | Nouveaux derives de la purine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilistion |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| GB0113041D0 (en) | 2001-05-30 | 2001-07-18 | Astrazeneca Ab | Chemical compounds |
| GB0127615D0 (en) | 2001-07-09 | 2002-01-09 | Aventis Pharm Prod Inc | Substituted amides, sulfonamides and ureas useful for inhibiting kinase activity |
| DE60206782T2 (de) * | 2001-07-09 | 2006-07-13 | Aventis Pharmaceuticals Inc. | Substituierte amide, sulfonamide und harnstoffe mit kinasehemmender wirkung |
| GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| US7442697B2 (en) | 2002-03-09 | 2008-10-28 | Astrazeneca Ab | 4-imidazolyl substituted pyrimidine derivatives with CDK inhibitory activity |
| GB0205693D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| GB0205688D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| EP1556129A4 (en) * | 2002-10-15 | 2011-02-09 | Irm Llc | COMPOSITIONS AND METHODS OF INDUCING OSTEOGENESIS |
| WO2004054581A2 (en) * | 2002-12-13 | 2004-07-01 | Smithkline Beecham Corporation | Cyclohexyl compounds as ccr5 antagonists |
| US7160834B2 (en) * | 2003-03-18 | 2007-01-09 | Exxonmobil Chemical Patents Inc. | Soluble group-10 α-diimine catalyst precursors, catalysts and methods for dimerizing and oligomerizing olefins |
| GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| US20050065171A1 (en) * | 2003-06-25 | 2005-03-24 | Shakespeare William C. | Substituted purine derivatives |
| MXPA06001758A (es) * | 2003-08-15 | 2006-08-11 | Irm Llc | Anilino purinas sustituidas en la posicion 6 utiles como inhibidores de rtk. |
| WO2005047524A2 (en) * | 2003-11-10 | 2005-05-26 | The Scripps Research Institute | Compositions and methods for inducing cell dedifferentiation |
| TW200528101A (en) | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
| GB0407723D0 (en) * | 2004-04-05 | 2004-05-12 | Novartis Ag | Organic compounds |
| JP5321061B2 (ja) | 2005-08-11 | 2013-10-23 | アリアド・ファーマシューティカルズ・インコーポレイテッド | 不飽和複素環誘導体 |
| AR056556A1 (es) | 2005-09-30 | 2007-10-10 | Astrazeneca Ab | Imidazo(1,2-a)piridina con actividad antiproliferacion celular |
| WO2007070872A1 (en) | 2005-12-15 | 2007-06-21 | Rigel Pharmaceuticals, Inc. | Kinase inhibitors and their uses |
| GB0526246D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| CN101148449B (zh) * | 2006-09-20 | 2010-08-11 | 浙江医药股份有限公司新昌制药厂 | 2-(6-喹啉氨基)-6-环丙氨基-9h-嘌呤成盐的方法 |
| EP2330908A4 (en) * | 2008-08-15 | 2011-11-23 | Univ Georgetown | FLUORESCENT CDK INHIBITORS FOR CANCER TREATMENT |
| CA2743449C (en) | 2008-11-12 | 2016-10-18 | Ariad Pharmaceuticals, Inc. | Pyrazinopyrazines and derivatives as kinase inhibitors |
| WO2011090738A2 (en) | 2009-12-29 | 2011-07-28 | Dana-Farber Cancer Institute, Inc. | Type ii raf kinase inhibitors |
| WO2012115575A1 (en) * | 2011-02-21 | 2012-08-30 | Biomatcell Ab | Derivatives for inducing osteogenic differentiation |
| US9382239B2 (en) | 2011-11-17 | 2016-07-05 | Dana-Farber Cancer Institute, Inc. | Inhibitors of c-Jun-N-terminal kinase (JNK) |
| EP2953470B1 (en) | 2013-02-07 | 2020-01-22 | Merck Sharp & Dohme Corp. | 2,6,7 substituted purines as hdm2 inhibitors |
| CN104447746A (zh) * | 2013-09-18 | 2015-03-25 | 华安医学股份有限公司 | 一种活化ampk的化合物及其用途 |
| KR101879422B1 (ko) * | 2013-09-18 | 2018-07-17 | 베이징 한미 파마슈티컬 컴퍼니 리미티드 | Btk 및/또는 jak3 키나제의 활성을 억제하는 화합물 |
| EP3057956B1 (en) | 2013-10-18 | 2021-05-05 | Dana-Farber Cancer Institute, Inc. | Polycyclic inhibitors of cyclin-dependent kinase 7 (cdk7) |
| CN108064274A (zh) | 2014-07-30 | 2018-05-22 | 耶达研究及发展有限公司 | 用于培养多能干细胞的培养基 |
| JP6854762B2 (ja) | 2014-12-23 | 2021-04-07 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | サイクリン依存性キナーゼ７（ｃｄｋ７）の阻害剤 |
| USRE50776E1 (en) | 2015-03-27 | 2026-02-03 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| AU2016319125B2 (en) | 2015-09-09 | 2021-04-08 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| US10722515B2 (en) * | 2016-09-30 | 2020-07-28 | Sri International | Dual CLK/CDK1 inhibitors for cancer treatment |
| CN110691782A (zh) * | 2016-12-01 | 2020-01-14 | 艾普托斯生物科学公司 | 作为brd4和jak2双重抑制剂的稠合的嘧啶化合物及其使用方法 |
| EP3810132A4 (en) | 2018-06-25 | 2022-06-22 | Dana-Farber Cancer Institute, Inc. | TAIRE FAMILY KINASE INHIBITORS AND RELATED USES |
| EP3914698B1 (en) | 2019-01-23 | 2024-12-11 | Yeda Research and Development Co. Ltd | Culture media for pluripotent stem cells |
| EP3947382B1 (en) | 2019-03-26 | 2025-09-24 | Academia Sinica | Compounds for uses in pharmacological induction of hbf for treatment of sickle cell disease and beta-thalassemia |
| US20240247001A1 (en) | 2022-12-16 | 2024-07-25 | Astrazeneca Ab | 2,6,9-trisubstituted purines |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE212535C (https=) | ||||
| DE3529497A1 (de) | 1985-08-17 | 1987-02-26 | Boehringer Mannheim Gmbh | N(pfeil hoch)6(pfeil hoch)-disubstituierte purinderivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| US5565566A (en) | 1987-04-24 | 1996-10-15 | Discovery Therapeutics, Inc. | N6 -substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| US5066655A (en) | 1987-04-24 | 1991-11-19 | Whitby Research, Inc. | N6-substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| CA1340361C (en) | 1987-04-24 | 1999-02-02 | Whitby Research, Inc. | N6-substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| KR910700253A (ko) | 1989-01-31 | 1991-03-14 | 로버트 제이, 바란 | N_6-치환-9-메틸아데닌: 신규한 부류의 아데노신 수용체 길항질 |
| US6403599B1 (en) | 1995-11-08 | 2002-06-11 | Pfizer Inc | Corticotropin releasing factor antagonists |
| AU7296896A (en) * | 1995-11-01 | 1997-05-22 | Novartis Ag | Purine derivatives and processes for their preparation |
| FR2741881B1 (fr) | 1995-12-01 | 1999-07-30 | Centre Nat Rech Scient | Nouveaux derives de purine possedant notamment des prorietes anti-proliferatives et leurs applications biologiques |
| US6107300A (en) | 1996-03-27 | 2000-08-22 | Dupont Pharmaceuticals | Arylamino fused pyrimidines |
| US5866702A (en) | 1996-08-02 | 1999-02-02 | Cv Therapeutics, Incorporation | Purine inhibitors of cyclin dependent kinase 2 |
| US5753635A (en) | 1996-08-16 | 1998-05-19 | Berlex Laboratories, Inc. | Purine derivatives and their use as anti-coagulants |
| WO1998016528A1 (en) * | 1996-10-11 | 1998-04-23 | Chiron Corporation | Purine inhibitors of glycogen synthase kinase 3 (gsk3) |
| US6255485B1 (en) * | 1997-08-07 | 2001-07-03 | The Regents Of The University Of California | Purine inhibitors of protein kinases, G proteins and polymerases |
| AUPO912997A0 (en) | 1997-09-11 | 1997-10-02 | Commonwealth Scientific And Industrial Research Organisation | Antiviral agents |
| US6479487B1 (en) * | 1998-02-26 | 2002-11-12 | Aventis Pharmaceuticals Inc. | 6, 9-disubstituted 2-[trans-(4-aminocyclohexyl)amino] purines |
-
1999
- 1999-02-18 GB GBGB9903762.4A patent/GB9903762D0/en not_active Ceased
-
2000
- 2000-02-16 CA CA002360353A patent/CA2360353A1/en not_active Abandoned
- 2000-02-16 AU AU38045/00A patent/AU3804500A/en not_active Abandoned
- 2000-02-16 EP EP00916840A patent/EP1153024B1/en not_active Expired - Lifetime
- 2000-02-16 WO PCT/EP2000/001271 patent/WO2000049018A1/en not_active Ceased
- 2000-02-16 DE DE60010234T patent/DE60010234T2/de not_active Expired - Fee Related
- 2000-02-16 JP JP2000599757A patent/JP2002537300A/ja active Pending
- 2000-02-16 PT PT00916840T patent/PT1153024E/pt unknown
- 2000-02-16 BR BR0008365-8A patent/BR0008365A/pt not_active Application Discontinuation
- 2000-02-16 ES ES00916840T patent/ES2219326T3/es not_active Expired - Lifetime
- 2000-02-16 AT AT00916840T patent/ATE265456T1/de not_active IP Right Cessation
- 2000-02-16 CN CNB008038155A patent/CN1183133C/zh not_active Expired - Fee Related
-
2001
- 2001-08-10 US US09/927,322 patent/US6767906B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60010234T2 (de) | 2005-04-14 |
| DE60010234D1 (de) | 2004-06-03 |
| ES2219326T3 (es) | 2004-12-01 |
| JP2002537300A (ja) | 2002-11-05 |
| GB9903762D0 (en) | 1999-04-14 |
| ATE265456T1 (de) | 2004-05-15 |
| HK1042479A1 (en) | 2002-08-16 |
| AU3804500A (en) | 2000-09-04 |
| CN1183133C (zh) | 2005-01-05 |
| US6767906B2 (en) | 2004-07-27 |
| CN1340054A (zh) | 2002-03-13 |
| EP1153024A1 (en) | 2001-11-14 |
| BR0008365A (pt) | 2001-11-13 |
| PT1153024E (pt) | 2004-08-31 |
| EP1153024B1 (en) | 2004-04-28 |
| US20020016329A1 (en) | 2002-02-07 |
| WO2000049018A1 (en) | 2000-08-24 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |