CA2624879A1 - Imidazopyridine derivatives as a2b adenosine receptor antagonists - Google Patents
Imidazopyridine derivatives as a2b adenosine receptor antagonists Download PDFInfo
- Publication number
- CA2624879A1 CA2624879A1 CA002624879A CA2624879A CA2624879A1 CA 2624879 A1 CA2624879 A1 CA 2624879A1 CA 002624879 A CA002624879 A CA 002624879A CA 2624879 A CA2624879 A CA 2624879A CA 2624879 A1 CA2624879 A1 CA 2624879A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- imidazo
- fluoropyridin
- pyridine
- 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
- 101150078577 Adora2b gene Proteins 0.000 title claims description 13
- 229940121359 adenosine receptor antagonist Drugs 0.000 title 1
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 title 1
- 239000005557 antagonist Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 133
- 238000000034 method Methods 0.000 claims description 86
- -1 C1-4alkylthio Chemical group 0.000 claims description 60
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 58
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 230000008485 antagonism Effects 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 230000001575 pathological effect Effects 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 229940043355 kinase inhibitor Drugs 0.000 claims description 6
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 208000017442 Retinal disease Diseases 0.000 claims description 5
- 206010038923 Retinopathy Diseases 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 208000031225 myocardial ischemia Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical class 0.000 claims description 4
- JTOPDADHARSMBZ-UHFFFAOYSA-N 6-(3,5-difluoropyridin-4-yl)-5-pyridin-3-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC1=CN=CC(F)=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(=O)N2 JTOPDADHARSMBZ-UHFFFAOYSA-N 0.000 claims description 3
- 206010006482 Bronchospasm Diseases 0.000 claims description 3
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims description 3
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims description 3
- 108010008212 Integrin alpha4beta1 Proteins 0.000 claims description 3
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 3
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 3
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 3
- 102100037346 Substance-P receptor Human genes 0.000 claims description 3
- 102000000551 Syk Kinase Human genes 0.000 claims description 3
- 108010016672 Syk Kinase Proteins 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
- 230000007885 bronchoconstriction Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
- 239000000018 receptor agonist Substances 0.000 claims description 3
- 229940044601 receptor agonist Drugs 0.000 claims description 3
- CMGXDPCRFRFEQJ-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C=C3OCCOC3=CC=1)=N2 CMGXDPCRFRFEQJ-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBCQUZAGZOW-UHFFFAOYSA-N 2-cyclohexyl-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1H-imidazo[4,5-b]pyridine 6-(3-fluoropyridin-4-yl)-2-methyl-5-pyridin-3-yl-1H-imidazo[4,5-b]pyridine Chemical compound FC=1C=NC=CC1C=1C=C2C(=NC1C=1C=NC=CC1)NC(=N2)C.C2(CCCCC2)C2=NC=1C(=NC(=C(C1)C1=C(C=NC=C1)F)C=1C=NC=CC1)N2 UIIMBCQUZAGZOW-UHFFFAOYSA-N 0.000 claims description 2
- SIBXJJSFYUSKKF-UHFFFAOYSA-N 3-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2NC3=NC(=C(C=4C(=CN=CC=4)F)C=C3N=2)C=2C=NC=CC=2)=C1 SIBXJJSFYUSKKF-UHFFFAOYSA-N 0.000 claims description 2
- FNODNDXVTBQNKZ-UHFFFAOYSA-N ClC=1C=NC=CC1C1=C(C=C2C(=N1)NC(N2)=O)C2=C(C=NC=C2)Cl.ClC=2C=NC=CC2C2=C(C=C1C(=N2)NC(=N1)C1=CC=C(C=C1)F)C1=C(C=NC=C1)F Chemical compound ClC=1C=NC=CC1C1=C(C=C2C(=N1)NC(N2)=O)C2=C(C=NC=C2)Cl.ClC=2C=NC=CC2C2=C(C=C1C(=N2)NC(=N1)C1=CC=C(C=C1)F)C1=C(C=NC=C1)F FNODNDXVTBQNKZ-UHFFFAOYSA-N 0.000 claims description 2
- FUNCKMRRMDSPIY-UHFFFAOYSA-N FC=1C=NC=C(C1C=1C=C2C(=NC1C=1C=NC=CC1)NC(=N2)C2=CC=C(C(=O)O)C=C2)F.FC=2C=NC=C(C2C=2C=C1C(=NC2C=2C=NC=CC2)NC(=N1)C1=CC=C(C=C1)F)F Chemical compound FC=1C=NC=C(C1C=1C=C2C(=NC1C=1C=NC=CC1)NC(=N2)C2=CC=C(C(=O)O)C=C2)F.FC=2C=NC=C(C2C=2C=C1C(=NC2C=2C=NC=CC2)NC(=N1)C1=CC=C(C=C1)F)F FUNCKMRRMDSPIY-UHFFFAOYSA-N 0.000 claims description 2
- CDYVNSLDLSBKKS-UHFFFAOYSA-N FC=1C=NC=CC1C=1C=C2C(=NC1C=1C=NC=CC1)NC(=N2)N2CCCCC2.FC=2C=NC=CC2C=2C=C1C(=NC2C=2C=NC=CC2)NC(=N1)N1CCOCC1 Chemical compound FC=1C=NC=CC1C=1C=C2C(=NC1C=1C=NC=CC1)NC(=N2)N2CCCCC2.FC=2C=NC=CC2C=2C=C1C(=NC2C=2C=NC=CC2)NC(=N1)N1CCOCC1 CDYVNSLDLSBKKS-UHFFFAOYSA-N 0.000 claims description 2
- HNBMFBBYJKQYDH-UHFFFAOYSA-N FC=1C=NC=CC1C=1C=C2C(=NC1C=1OC=CN1)NC=N2.FC=2C=NC=CC2C=2C=C1C(=NC2C=2OC=CN2)NC(N1)=O Chemical compound FC=1C=NC=CC1C=1C=C2C(=NC1C=1OC=CN1)NC=N2.FC=2C=NC=CC2C=2C=C1C(=NC2C=2OC=CN2)NC(N1)=O HNBMFBBYJKQYDH-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 208000035269 cancer or benign tumor Diseases 0.000 claims 2
- KUWIWMQUBPJPGE-UHFFFAOYSA-N 2-(3-fluorophenyl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1H-imidazo[4,5-b]pyridine 6-(3-fluoropyridin-4-yl)-2,5-dipyridin-3-yl-1H-imidazo[4,5-b]pyridine Chemical compound FC=1C=NC=CC1C=1C=C2C(=NC1C=1C=NC=CC1)NC(=N2)C=2C=NC=CC2.FC=2C=C(C=CC2)C2=NC=1C(=NC(=C(C1)C1=C(C=NC=C1)F)C=1C=NC=CC1)N2 KUWIWMQUBPJPGE-UHFFFAOYSA-N 0.000 claims 1
- QEFGTGPZSGHXNT-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-(2-methylpyrazol-3-yl)-5-pyridin-3-yl-1H-imidazo[4,5-b]pyridine Chemical compound CN1N=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 QEFGTGPZSGHXNT-UHFFFAOYSA-N 0.000 claims 1
- YJJBVCAWJOZRLC-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]-5-pyridin-3-yl-1H-imidazo[4,5-b]pyridine Chemical compound CN1N=C(C(F)(F)F)C=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 YJJBVCAWJOZRLC-UHFFFAOYSA-N 0.000 claims 1
- 102000007470 Adenosine A2B Receptor Human genes 0.000 claims 1
- 108010085273 Adenosine A2B receptor Proteins 0.000 claims 1
- STRHNGYZIUTJMX-UHFFFAOYSA-N C1(CC1)C1=NC=2C(=NC(=C(C2)C2=C(C=NC=C2)F)C=2C=NC=CC2)N1.FC=1C=NC=CC1C=1C=C2C(=NC1C=1C=NC=CC1)NC(N2)=O Chemical compound C1(CC1)C1=NC=2C(=NC(=C(C2)C2=C(C=NC=C2)F)C=2C=NC=CC2)N1.FC=1C=NC=CC1C=1C=C2C(=NC1C=1C=NC=CC1)NC(N2)=O STRHNGYZIUTJMX-UHFFFAOYSA-N 0.000 claims 1
- TVAHJJKHYAKUNX-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC1=NC=2C(=NC(=C(C2)C2=C(C=NC=C2)F)C=2C=NC=CC2)N1.FC=1C=C(C=C(C1)F)C(=O)C1=NC=2C(=NC(=C(C2)C2=C(C=NC=C2)F)C=2C=NC=CC2)N1 Chemical compound ClC1=CC=C(C=C1)NC1=NC=2C(=NC(=C(C2)C2=C(C=NC=C2)F)C=2C=NC=CC2)N1.FC=1C=C(C=C(C1)F)C(=O)C1=NC=2C(=NC(=C(C2)C2=C(C=NC=C2)F)C=2C=NC=CC2)N1 TVAHJJKHYAKUNX-UHFFFAOYSA-N 0.000 claims 1
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- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
- LHJCZOXMCGQVDQ-UHFFFAOYSA-N tri(propan-2-yl)silyl trifluoromethanesulfonate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F LHJCZOXMCGQVDQ-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITBMRVUPEVXILF-UHFFFAOYSA-N tributyl-(3,5-difluoropyridin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=C(F)C=NC=C1F ITBMRVUPEVXILF-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- 230000006442 vascular tone Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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
- A61K31/435—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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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
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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
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ESP200502433 | 2005-10-06 | ||
| ES200502433A ES2274712B1 (es) | 2005-10-06 | 2005-10-06 | Nuevos derivados imidazopiridina. |
| PCT/EP2006/009620 WO2007039297A1 (en) | 2005-10-06 | 2006-10-05 | Imidazopyridine derivatives as a2b adenosine receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2624879A1 true CA2624879A1 (en) | 2007-04-12 |
Family
ID=36295447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002624879A Abandoned CA2624879A1 (en) | 2005-10-06 | 2006-10-05 | Imidazopyridine derivatives as a2b adenosine receptor antagonists |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7855202B2 (https=) |
| EP (1) | EP1931666A1 (https=) |
| JP (1) | JP2009510152A (https=) |
| KR (1) | KR20080050475A (https=) |
| CN (1) | CN101326181A (https=) |
| AR (1) | AR055676A1 (https=) |
| AU (1) | AU2006299028A1 (https=) |
| CA (1) | CA2624879A1 (https=) |
| EC (1) | ECSP088343A (https=) |
| ES (1) | ES2274712B1 (https=) |
| IL (1) | IL190336A0 (https=) |
| NO (1) | NO20082121L (https=) |
| PE (1) | PE20070706A1 (https=) |
| RU (1) | RU2008117329A (https=) |
| TW (1) | TW200800985A (https=) |
| UY (1) | UY29836A1 (https=) |
| WO (1) | WO2007039297A1 (https=) |
| ZA (1) | ZA200802588B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2011299894B2 (en) * | 2010-09-10 | 2015-08-06 | Shionogi & Co., Ltd. | Hetero ring-fused imidazole derivative having AMPK activating effect |
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| ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| MX337906B (es) | 2006-10-19 | 2016-03-28 | Signal Pharm Llc | Compuestos de heteroarilo, composiciones de los mismos, y su uso como inhibidores de proteina cinasas. |
| ES2303776B1 (es) * | 2006-12-29 | 2009-08-07 | Laboratorios Almirall S.A. | Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b. |
| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| CA2684105C (en) | 2007-05-03 | 2011-09-06 | Pfizer Limited | Pyridine derivatives |
| AU2008343813B2 (en) * | 2007-12-19 | 2012-04-12 | Amgen Inc. | Inhibitors of PI3 kinase |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| PT2294066E (pt) * | 2008-04-28 | 2014-11-21 | Janssen Pharmaceutica Nv | Benzoimidazoles como inibidores da prolil-hidroxilase |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| WO2010133534A1 (en) * | 2009-05-19 | 2010-11-25 | Cellzome Limited | Bicyclic amino substituted compounds as pi3k inhibitors |
| EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
| US20120003329A1 (en) | 2010-06-30 | 2012-01-05 | Gilead Sciences, Inc. | Use of A2B Adenosine Receptor Antagonists for Treating Pulmonary Hypertension |
| AR085942A1 (es) | 2011-04-07 | 2013-11-06 | Gilead Sciences Inc | Uso de receptor de aadenosina para tratar la insuficiencia cardiaca y la arritmia en pacientes posinfarto de miocardio |
| CA2836487A1 (en) * | 2011-06-09 | 2012-12-13 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of gpr-119 |
| WO2013063221A1 (en) | 2011-10-25 | 2013-05-02 | Janssen Pharmaceutica Nv | Meglumine salt formulations of 1-(5,6-dichloro-1h-benzo[d]imidazol-2-yl)-1h-pyrazole-4-carboxylic acid |
| EA201400990A1 (ru) | 2012-04-06 | 2015-01-30 | Пфайзер Инк. | Ингибиторы диацилглицеринацилтрансферазы 2 |
| EP2861596B1 (en) * | 2012-06-19 | 2019-03-20 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| WO2014145852A2 (en) * | 2013-03-15 | 2014-09-18 | Knopp Biosciences Llc | Imidazo(4,5-b) pyridin-2-yl amides as kv7 channel activators |
| US11175268B2 (en) | 2014-06-09 | 2021-11-16 | Biometry Inc. | Mini point of care gas chromatographic test strip and method to measure analytes |
| CN106537128B (zh) | 2014-06-09 | 2021-06-18 | 生物统计股份有限公司 | 用于测量分析物的低成本测试条和方法 |
| SMT202300362T1 (it) | 2014-09-12 | 2023-11-13 | Biohaven Therapeutics Ltd | Benzoimidazol-1,2-il-ammidi come attivatori di canale kv7 |
| ES2580702B1 (es) * | 2015-02-25 | 2017-06-08 | Palobiofarma, S.L. | Derivados de 2-aminopiridina como antagonistas del receptor A2b de adenosina y ligandos del receptor MT3 de melatonina |
| CN114859028A (zh) | 2016-07-19 | 2022-08-05 | 生物统计股份有限公司 | 使用批量可校准测试条测量分析物的方法和系统 |
| EP3562306B1 (en) | 2016-12-29 | 2025-02-26 | Ji Xing Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| JP7227157B2 (ja) | 2016-12-29 | 2023-02-21 | フェーズバイオ ファーマシューティカルズ，インコーポレイテッド | 金属酵素阻害剤化合物 |
| JP6836693B2 (ja) | 2017-09-28 | 2021-03-03 | シーストーン・ファーマスーティカルズ・（スージョウ）・カンパニー・リミテッドＣｓｔｏｎｅ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ （Ｓｕｚｈｏｕ） Ｃｏ．， Ｌｔｄ． | Ａ２ａ受容体アンタゴニストとしての縮合環誘導体 |
| PT3792260T (pt) * | 2018-05-08 | 2024-10-02 | Nippon Shinyaku Co Ltd | Compostos de azabenzimidazol e produtos farmacêuticos |
| JP2022516969A (ja) | 2019-01-08 | 2022-03-03 | フェーズバイオ ファーマシューティカルズ，インコーポレイテッド | 金属酵素阻害剤化合物 |
| MX2021008094A (es) | 2019-01-11 | 2021-09-21 | Omeros Corp | Metodos y composiciones para el tratamiento del cancer. |
| CA3161582A1 (en) | 2019-11-13 | 2021-05-20 | Nippon Shinyaku Co., Ltd. | Azabenzimidazole compound and medicine |
| BR112022008457A2 (pt) * | 2019-11-13 | 2022-07-26 | Nippon Shinyaku Co Ltd | Agente terapêutico e agente profilático para distúrbios gastrointestinais funcionais e xerostomia |
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| GB9309573D0 (en) * | 1993-05-10 | 1993-06-23 | Merck Sharp & Dohme | Therapeutic agents |
| KR0151816B1 (ko) * | 1994-02-08 | 1998-10-15 | 강박광 | 신규의 치환된 피리딜 이미다졸 유도체 및 그의 제조방법 |
| US5686470A (en) * | 1995-02-10 | 1997-11-11 | Weier; Richard M. | 2, 3-substituted pyridines for the treatment of inflammation |
| US6096748A (en) | 1996-03-13 | 2000-08-01 | Smithkline Beecham Corporation | Pyrimidine compounds useful in treating cytokine mediated diseases |
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| IL136711A0 (en) | 1997-12-19 | 2001-06-14 | Amgen Inc | Substituted pyridine and pyridazine compounds and their pharmaceutical use |
| WO1999065897A1 (en) | 1998-06-19 | 1999-12-23 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| US6545002B1 (en) | 1999-06-01 | 2003-04-08 | University Of Virginia Patent Foundation | Substituted 8-phenylxanthines useful as antagonists of A2B adenosine receptors |
| US6841549B1 (en) * | 1999-07-02 | 2005-01-11 | Eisai Co., Ltd. | Condensed imidazole compounds and a therapeutic agent for diabetes mellitus |
| DE60001969T2 (de) | 1999-08-31 | 2004-02-05 | Vanderbilt University, Nashville | Selektive antagonisten von a2b adenosinrezeptoren |
| EP1255550A2 (en) | 2000-02-17 | 2002-11-13 | Cv Therapeutics, Inc. | Method for identifying and using a 2b adenosine receptor antagonists to mediate mammalian cell proliferation |
| WO2001062233A2 (en) | 2000-02-25 | 2001-08-30 | F. Hoffmann La Roche Ag | Adenosine receptor modulators |
| AU5260601A (en) | 2000-04-26 | 2001-11-07 | Eisai Co Ltd | Medicinal compositions promoting bowel movement |
| CN1446202A (zh) | 2000-08-11 | 2003-10-01 | 卫材株式会社 | 2－氨基吡啶化合物及其作为药物的用途 |
| AU9502601A (en) | 2000-09-06 | 2002-03-22 | Chiron Corp | Inhibitors of glycogen synthase kinase 3 |
| WO2002022605A1 (en) | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| EP1360286A2 (en) | 2000-09-19 | 2003-11-12 | Chiron Corporation | Characterization of the gsk-3beta protein and methods of use thereof |
| GB0028383D0 (en) | 2000-11-21 | 2001-01-03 | Novartis Ag | Organic compounds |
| DK1401837T3 (da) * | 2001-06-29 | 2005-11-07 | Cv Therapeutics Inc | Purinderivater som A2B-adenosinreceptorantagonister |
| TWI330183B (https=) | 2001-10-22 | 2010-09-11 | Eisai R&D Man Co Ltd | |
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| WO2003068773A1 (en) * | 2002-02-12 | 2003-08-21 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| EP1492784A4 (en) | 2002-03-28 | 2006-03-29 | Merck & Co Inc | SUBSTITUTED 2,3-DIPHENYLPYRIDINES |
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| KR101222364B1 (ko) | 2003-08-25 | 2013-01-15 | 트로비스 파마슈티칼스 엘엘씨 | 치환된 8-헤테로아릴 크산틴 |
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| GB0323138D0 (en) | 2003-10-03 | 2003-11-05 | Chang Lisa C W | Pyrimidines substituted in the 2,4,6 positions and their different uses |
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| ES2241496B1 (es) * | 2004-04-15 | 2006-12-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridina. |
| ES2270715B1 (es) | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| ES2303776B1 (es) | 2006-12-29 | 2009-08-07 | Laboratorios Almirall S.A. | Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b. |
-
2005
- 2005-10-06 ES ES200502433A patent/ES2274712B1/es not_active Expired - Fee Related
-
2006
- 2006-10-03 UY UY29836A patent/UY29836A1/es unknown
- 2006-10-04 PE PE2006001205A patent/PE20070706A1/es not_active Application Discontinuation
- 2006-10-05 KR KR1020087008297A patent/KR20080050475A/ko not_active Withdrawn
- 2006-10-05 AU AU2006299028A patent/AU2006299028A1/en not_active Abandoned
- 2006-10-05 WO PCT/EP2006/009620 patent/WO2007039297A1/en not_active Ceased
- 2006-10-05 CA CA002624879A patent/CA2624879A1/en not_active Abandoned
- 2006-10-05 AR ARP060104379A patent/AR055676A1/es unknown
- 2006-10-05 RU RU2008117329/04A patent/RU2008117329A/ru not_active Application Discontinuation
- 2006-10-05 JP JP2008533934A patent/JP2009510152A/ja active Pending
- 2006-10-05 US US12/089,050 patent/US7855202B2/en not_active Expired - Fee Related
- 2006-10-05 EP EP06806042A patent/EP1931666A1/en not_active Withdrawn
- 2006-10-05 CN CNA2006800371946A patent/CN101326181A/zh active Pending
- 2006-10-05 TW TW095137259A patent/TW200800985A/zh unknown
-
2008
- 2008-03-20 IL IL190336A patent/IL190336A0/en unknown
- 2008-03-20 ZA ZA200802588A patent/ZA200802588B/xx unknown
- 2008-04-03 EC EC2008008343A patent/ECSP088343A/es unknown
- 2008-05-06 NO NO20082121A patent/NO20082121L/no not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2011299894B2 (en) * | 2010-09-10 | 2015-08-06 | Shionogi & Co., Ltd. | Hetero ring-fused imidazole derivative having AMPK activating effect |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200800985A (en) | 2008-01-01 |
| JP2009510152A (ja) | 2009-03-12 |
| AR055676A1 (es) | 2007-08-29 |
| NO20082121L (no) | 2008-07-07 |
| KR20080050475A (ko) | 2008-06-05 |
| ECSP088343A (es) | 2008-05-30 |
| ES2274712B1 (es) | 2008-03-01 |
| ZA200802588B (en) | 2009-09-30 |
| US7855202B2 (en) | 2010-12-21 |
| CN101326181A (zh) | 2008-12-17 |
| UY29836A1 (es) | 2007-04-30 |
| EP1931666A1 (en) | 2008-06-18 |
| IL190336A0 (en) | 2009-09-22 |
| WO2007039297A1 (en) | 2007-04-12 |
| US20080275038A1 (en) | 2008-11-06 |
| PE20070706A1 (es) | 2007-09-24 |
| ES2274712A1 (es) | 2007-05-16 |
| RU2008117329A (ru) | 2009-11-20 |
| AU2006299028A1 (en) | 2007-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |