JP2003512467A - チアゾールおよびイミダゾ（４，５−ｂ）ピリジン化合物ならびにそれらの医薬用途 - Google Patents
チアゾールおよびイミダゾ（４，５−ｂ）ピリジン化合物ならびにそれらの医薬用途Info
- Publication number
- JP2003512467A JP2003512467A JP2001533132A JP2001533132A JP2003512467A JP 2003512467 A JP2003512467 A JP 2003512467A JP 2001533132 A JP2001533132 A JP 2001533132A JP 2001533132 A JP2001533132 A JP 2001533132A JP 2003512467 A JP2003512467 A JP 2003512467A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- optionally
- substituted
- fluorophenyl
- pyrimidinyl
- 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.)
- Pending
Links
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title claims description 34
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title description 3
- 239000002253 acid Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract description 14
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 108
- -1 Each Halo Chemical group 0.000 claims description 101
- 239000000126 substance Substances 0.000 claims description 85
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 70
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000006413 ring segment Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 239000002243 precursor Substances 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 208000023275 Autoimmune disease Diseases 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 230000001363 autoimmune Effects 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 6
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 239000003018 immunosuppressive agent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- ICHINRNOSJBRCE-HNNXBMFYSA-N 2-(4-fluorophenyl)-1-[2-[[(1s)-1-phenylethyl]amino]pyrimidin-4-yl]imidazo[4,5-b]pyridin-5-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1N(C1=CC=C(N)N=C1N=1)C=1C1=CC=C(F)C=C1 ICHINRNOSJBRCE-HNNXBMFYSA-N 0.000 claims description 4
- XUQRICHQPSQKSS-FQEVSTJZSA-N 4-[2-(4-fluorophenyl)-5-(4-methylpiperazin-1-yl)imidazo[4,5-b]pyridin-1-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1N(C1=CC=2)C(C=3C=CC(F)=CC=3)=NC1=NC=2N1CCN(C)CC1 XUQRICHQPSQKSS-FQEVSTJZSA-N 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000001091 aminosulfinyl group Chemical class [H]N([H])S(*)=O 0.000 claims description 4
- 125000004682 aminothiocarbonyl group Chemical class NC(=S)* 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 229940125721 immunosuppressive agent Drugs 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- GFJQCVZKRHKDIX-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-pyridin-4-ylimidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(C=3C=CN=CC=3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 GFJQCVZKRHKDIX-UHFFFAOYSA-N 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- QWLKXLNJJRBNII-UHFFFAOYSA-N 1-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[4,5-b]pyridin-5-amine Chemical compound N=1C2=NC(N)=CC=C2N(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 QWLKXLNJJRBNII-UHFFFAOYSA-N 0.000 claims description 3
- HQYTZGXGJITFDL-UHFFFAOYSA-N 1-[2-(cyclopentylamino)pyrimidin-4-yl]-n-(3-fluorophenyl)-2-(4-fluorophenyl)imidazo[4,5-b]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(NC=3C=C(F)C=CC=3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 HQYTZGXGJITFDL-UHFFFAOYSA-N 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 238000006254 arylation reaction Methods 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- MGIUUUFXHGZVRO-UHFFFAOYSA-N n-benzyl-1-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[4,5-b]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(NCC=3C=CC=CC=3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 MGIUUUFXHGZVRO-UHFFFAOYSA-N 0.000 claims description 3
- UBTOWEAWXVZTQD-UHFFFAOYSA-N n-cyclobutyl-4-[2-(4-fluorophenyl)-5-(4-methylpiperazin-1-yl)imidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=C(N(C(=N2)C=3C=CC(F)=CC=3)C=3N=C(NC4CCC4)N=CC=3)C2=N1 UBTOWEAWXVZTQD-UHFFFAOYSA-N 0.000 claims description 3
- DESTZNVBBLDULL-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-(1-methylpiperidin-4-yl)imidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1C1=CC=C(N(C(=N2)C=3C=CC(F)=CC=3)C=3N=C(NC4CCCC4)N=CC=3)C2=N1 DESTZNVBBLDULL-UHFFFAOYSA-N 0.000 claims description 3
- BARFMAOTOPEJFY-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-(4-methylpiperazin-1-yl)imidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=C(N(C(=N2)C=3C=CC(F)=CC=3)C=3N=C(NC4CCCC4)N=CC=3)C2=N1 BARFMAOTOPEJFY-UHFFFAOYSA-N 0.000 claims description 3
- YGDCPBYTBSIICB-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-morpholin-4-ylimidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(N3CCOCC3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 YGDCPBYTBSIICB-UHFFFAOYSA-N 0.000 claims description 3
- CMDWMHFRSWQQAO-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-pyridin-3-ylimidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NC2=NC(C=3C=NC=CC=3)=CC=C2N1C1=CC=NC(NC2CCCC2)=N1 CMDWMHFRSWQQAO-UHFFFAOYSA-N 0.000 claims description 3
- WRFUMBPRGLYOAV-UHFFFAOYSA-N n-cyclopropyl-4-[2-(4-fluorophenyl)-5-(4-methylpiperazin-1-yl)imidazo[4,5-b]pyridin-1-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=C(N(C(=N2)C=3C=CC(F)=CC=3)C=3N=C(NC4CC4)N=CC=3)C2=N1 WRFUMBPRGLYOAV-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 2
- 230000001861 immunosuppressant effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
- 125000000027 (C1-C10) alkoxy group Chemical class 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- MJMDLUIORMBKHA-IBGZPJMESA-N 4-[4-(4-fluorophenyl)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C=1SC(N2CCC(C)CC2)=NC=1C1=CC=C(F)C=C1 MJMDLUIORMBKHA-IBGZPJMESA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 241001274216 Naso Species 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical class NS(=O)(=O)* 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 1
- OONDROKXCHJESN-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-[4-(4-fluorophenyl)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound C1CC(C)CCN1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=C(NCC3CC3)N=CC=2)S1 OONDROKXCHJESN-UHFFFAOYSA-N 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
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- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 238000005160 1H NMR spectroscopy Methods 0.000 description 53
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- QCNCMKGQOCQRNB-KRWDZBQOSA-N 4-[4-(4-fluorophenyl)-2-piperidin-4-yl-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C=1SC(C2CCNCC2)=NC=1C1=CC=C(F)C=C1 QCNCMKGQOCQRNB-KRWDZBQOSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
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- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9925441.9 | 1999-10-27 | ||
| GBGB9925441.9A GB9925441D0 (en) | 1999-10-27 | 1999-10-27 | Organic compounds |
| GB9926173.7 | 1999-11-04 | ||
| GBGB9926173.7A GB9926173D0 (en) | 1999-11-04 | 1999-11-04 | Organic compounds |
| PCT/EP2000/010528 WO2001030778A1 (en) | 1999-10-27 | 2000-10-25 | Thiazole and imidazo [4,5-b] pyridine compounds and their pharmaceutical use |
Publications (2)
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| JP2003512467A true JP2003512467A (ja) | 2003-04-02 |
| JP2003512467A5 JP2003512467A5 (cg-RX-API-DMAC10.html) | 2007-12-06 |
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| EP (1) | EP1224185B1 (cg-RX-API-DMAC10.html) |
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| AT (1) | ATE311385T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU7922900A (cg-RX-API-DMAC10.html) |
| CO (1) | CO5251463A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE60024480T2 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2254238T3 (cg-RX-API-DMAC10.html) |
| PE (1) | PE20011039A1 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2001030778A1 (cg-RX-API-DMAC10.html) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005016910A1 (ja) * | 2003-08-18 | 2006-10-12 | 富士フイルムファインケミカルズ株式会社 | ピリジルテトラヒドロピリジン類およびピリジルピペリジン類とそれらの製造方法 |
| JP2007518767A (ja) * | 2004-01-21 | 2007-07-12 | ノバルティス アクチエンゲゼルシャフト | Ａ２ｂアンタゴニストとしてのチアゾール誘導体 |
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| JPWO2005016910A1 (ja) * | 2003-08-18 | 2006-10-12 | 富士フイルムファインケミカルズ株式会社 | ピリジルテトラヒドロピリジン類およびピリジルピペリジン類とそれらの製造方法 |
| US8530662B2 (en) | 2003-08-18 | 2013-09-10 | Fujifilm Finechemicals Co., Ltd | Pyridyltetrahydropyridines and pyridylpiperidines, and method of manufacturing them |
| JP2007518767A (ja) * | 2004-01-21 | 2007-07-12 | ノバルティス アクチエンゲゼルシャフト | Ａ２ｂアンタゴニストとしてのチアゾール誘導体 |
| JP2010538000A (ja) * | 2007-08-27 | 2010-12-09 | シガ・テクノロジーズ・インコーポレーテッド | アレナウイルス感染症を治療するための抗ウイルス薬 |
| JP2011520887A (ja) * | 2008-05-13 | 2011-07-21 | アイアールエム・リミテッド・ライアビリティ・カンパニー | キナーゼ阻害剤としての縮合窒素含有ヘテロ環およびその組成物 |
| JP2012527461A (ja) * | 2009-05-19 | 2012-11-08 | ダウ アグロサイエンシィズ エルエルシー | 真菌を防除するための化合物および方法 |
| JP2016529292A (ja) * | 2013-08-30 | 2016-09-23 | ピーティーシー セラピューティクス， インコーポレイテッド | 置換ピリミジンＢｍｉ−１阻害剤 |
| JP2016539979A (ja) * | 2013-12-09 | 2016-12-22 | ユーシービー バイオファルマ エスピーアールエル | Ｔｎｆ活性のモジュレーターとしてのイミダゾピリジン誘導体 |
| JP2018508553A (ja) * | 2015-03-18 | 2018-03-29 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 置換三環式ヘテロ環式化合物 |
| JP2018508554A (ja) * | 2015-03-18 | 2018-03-29 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｔｎｆ阻害剤として有用な三環式ヘテロ環式化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6891039B2 (en) | 2005-05-10 |
| EP1224185A1 (en) | 2002-07-24 |
| US6608072B1 (en) | 2003-08-19 |
| CO5251463A1 (es) | 2003-02-28 |
| ES2254238T3 (es) | 2006-06-16 |
| AU7922900A (en) | 2001-05-08 |
| US20040082604A1 (en) | 2004-04-29 |
| DE60024480T2 (de) | 2006-07-27 |
| AR029011A1 (es) | 2003-06-04 |
| ATE311385T1 (de) | 2005-12-15 |
| EP1224185B1 (en) | 2005-11-30 |
| PE20011039A1 (es) | 2001-10-30 |
| WO2001030778A1 (en) | 2001-05-03 |
| DE60024480D1 (de) | 2006-01-05 |
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