CA2834901A1 - Substituted imidazopyridines and imidazopyridazines and the use thereof - Google Patents
Substituted imidazopyridines and imidazopyridazines and the use thereof Download PDFInfo
- Publication number
- CA2834901A1 CA2834901A1 CA2834901A CA2834901A CA2834901A1 CA 2834901 A1 CA2834901 A1 CA 2834901A1 CA 2834901 A CA2834901 A CA 2834901A CA 2834901 A CA2834901 A CA 2834901A CA 2834901 A1 CA2834901 A1 CA 2834901A1
- Authority
- CA
- Canada
- Prior art keywords
- fluorine
- formula
- hydrogen
- alkyl
- group
- 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
- 150000005233 imidazopyridazines Chemical class 0.000 title abstract description 4
- 150000005232 imidazopyridines Chemical class 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 88
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 54
- 238000011282 treatment Methods 0.000 claims abstract description 40
- 238000011321 prophylaxis Methods 0.000 claims abstract description 37
- 239000003814 drug Substances 0.000 claims abstract description 14
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 279
- -1 hydroxy, phenyl Chemical group 0.000 claims description 200
- 229910052739 hydrogen Inorganic materials 0.000 claims description 123
- 239000001257 hydrogen Substances 0.000 claims description 123
- 229910052731 fluorine Inorganic materials 0.000 claims description 119
- 239000011737 fluorine Substances 0.000 claims description 118
- 150000002431 hydrogen Chemical class 0.000 claims description 103
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 91
- 150000003839 salts Chemical class 0.000 claims description 89
- 239000012453 solvate Substances 0.000 claims description 81
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 80
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 76
- 125000001153 fluoro group Chemical group F* 0.000 claims description 61
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 57
- 239000002904 solvent Substances 0.000 claims description 57
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 50
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 44
- 208000035475 disorder Diseases 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 36
- 239000012442 inert solvent Substances 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 239000002585 base Substances 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 239000000460 chlorine Chemical group 0.000 claims description 23
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 22
- 125000002393 azetidinyl group Chemical group 0.000 claims description 22
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 22
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 22
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 20
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 19
- LIUMDGLYGBIKBM-SFYKDHMMSA-N [(2s)-3-[[(2s)-1-[[(2s)-1-amino-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-[[3-[4-(3-chlorophenyl)phenyl]-1,2-oxazol-5-yl]methyl]-3-oxopropyl]-(4-bromophenyl)phosphinic acid Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(N)=O)CP(O)(=O)C=1C=CC(Br)=CC=1)C(ON=1)=CC=1C(C=C1)=CC=C1C1=CC=CC(Cl)=C1 LIUMDGLYGBIKBM-SFYKDHMMSA-N 0.000 claims description 18
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 18
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 18
- 125000000335 thiazolyl group Chemical group 0.000 claims description 18
- 125000001425 triazolyl group Chemical group 0.000 claims description 18
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 206010019280 Heart failures Diseases 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000003112 inhibitor Substances 0.000 claims description 17
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 230000003176 fibrotic effect Effects 0.000 claims description 14
- 201000006370 kidney failure Diseases 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims description 14
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 13
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 12
- 206010020772 Hypertension Diseases 0.000 claims description 12
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 11
- 206010002383 Angina Pectoris Diseases 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 230000009424 thromboembolic effect Effects 0.000 claims description 10
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 9
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 9
- 208000028867 ischemia Diseases 0.000 claims description 9
- GCVFCUPRTZORNH-UHFFFAOYSA-N n,n-dimethyl-3-[4-(1,10-phenanthrolin-4-yl)butoxy]aniline;2-pyridin-2-ylpyridine;ruthenium Chemical compound [Ru].N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1.CN(C)C1=CC=CC(OCCCCC=2C3=C(C4=NC=CC=C4C=C3)N=CC=2)=C1 GCVFCUPRTZORNH-UHFFFAOYSA-N 0.000 claims description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000003566 oxetanyl group Chemical group 0.000 claims description 8
- 208000019553 vascular disease Diseases 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 6
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000003146 anticoagulant agent Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
- 230000037356 lipid metabolism Effects 0.000 claims description 4
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 229960004676 antithrombotic agent Drugs 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 claims description 3
- 239000002220 antihypertensive agent Substances 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- GGCSQMNZKHRBJW-UHFFFAOYSA-N 3-[(4-ethoxyphenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1CNC1=NC2=CC(C(F)(F)F)=CC=C2N=C1C(O)=O GGCSQMNZKHRBJW-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 120
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 120
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 117
- 239000000203 mixture Substances 0.000 description 78
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 71
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 68
- 238000006243 chemical reaction Methods 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 39
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 39
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 34
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 32
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 29
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 235000019253 formic acid Nutrition 0.000 description 20
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 20
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 19
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 17
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- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 10
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- 239000005557 antagonist Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000002953 preparative HPLC Methods 0.000 description 9
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 8
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- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102011075399.0 | 2011-05-06 | ||
| DE102011075399A DE102011075399A1 (de) | 2011-05-06 | 2011-05-06 | Substituierte Imidazopyridine und Imidazopyridazine und ihre Verwendung |
| DE102012200356.8 | 2012-01-11 | ||
| DE201210200356 DE102012200356A1 (de) | 2012-01-11 | 2012-01-11 | Substituierte Imidazopyridine und Imidazopyridazine und ihre Verwendung |
| PCT/EP2012/058046 WO2012152629A1 (de) | 2011-05-06 | 2012-05-02 | Substituierte imidazopyridine und imidazopyridazine und ihre verwendung |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8765769B2 (en) | 2010-07-09 | 2014-07-01 | Bayer Intellectual Property Gmbh | Ring-fused 4-aminopyrimidines and use thereof as stimulators of soluable guanylate cyclases |
| US8859569B2 (en) | 2011-09-02 | 2014-10-14 | Bayer Pharma Aktiengesellschaft | Substituted annellated pyrimidines and use thereof |
| US9023849B2 (en) | 2012-01-11 | 2015-05-05 | Bayer Intellectual Property Gmbh | Substituted fused imidazoles and pyrazoles and use thereof |
| US9090610B2 (en) | 2011-04-21 | 2015-07-28 | Bayer Intellectual Property Gmbh | Fluoroalkyl-substituted pyrazolopyridines and use thereof |
| US9096592B2 (en) | 2010-09-03 | 2015-08-04 | Bayer Intellectual Property Gmbh | Bicyclic aza heterocycles, and use thereof |
| US9133191B2 (en) | 2012-01-11 | 2015-09-15 | Bayer Intellectual Property Gmbh | Substituted triazine derivatives and use thereof as stimulators of soluble guanylate cyclase |
| US9216978B2 (en) | 2010-07-09 | 2015-12-22 | Bayer Intellectual Property Gmbh | Ring-fused pyrimidines and triazines and use thereof for the treatment and/or prophylaxis of cardiovascular diseases |
| US9266871B2 (en) | 2013-03-01 | 2016-02-23 | Bayer Pharma Aktiengesellschaft | Trifluoromethyl-substituted fused pyrimidines and their use |
| US9498480B2 (en) | 2012-03-06 | 2016-11-22 | Bayer Intellectual Property Gmbh | Substituted azabicycles and use thereof |
| US9505786B2 (en) | 2012-01-11 | 2016-11-29 | Bayer Pharma Aktiengesellschaft | Substituted annulated triazines and use thereof |
| US9605008B2 (en) | 2013-07-10 | 2017-03-28 | Bayer Pharma Aktiengesellschaft | Benzyl-1H-pyrazolo[3,4-b]pyridines and use thereof |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2705851C (en) | 2007-11-21 | 2016-11-01 | Oregon Health & Science University | Anti-factor xi monoclonal antibodies and methods of use thereof |
| AU2009335643B2 (en) | 2008-12-18 | 2014-05-29 | Oregon Health & Science University | Anti-fXI antibodies and methods of use |
| DK3415515T3 (da) | 2009-11-27 | 2020-03-16 | Adverio Pharma Gmbh | Fremgangsmåde til fremstilling af methyl-{4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamat |
| US20140171434A1 (en) * | 2011-01-11 | 2014-06-19 | Bayer Pharma Aktiengessellschaft | Substituted imidazopyridines and imidazopyridazines and the use thereof |
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| DE102006043443A1 (de) * | 2006-09-15 | 2008-03-27 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
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| US20140171434A1 (en) * | 2011-01-11 | 2014-06-19 | Bayer Pharma Aktiengessellschaft | Substituted imidazopyridines and imidazopyridazines and the use thereof |
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2012
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- 2012-05-02 ES ES12717331.8T patent/ES2592267T3/es active Active
- 2012-05-02 EP EP12717331.8A patent/EP2705037B1/de not_active Not-in-force
- 2012-05-02 JP JP2014508787A patent/JP5976788B2/ja not_active Expired - Fee Related
- 2012-05-02 CA CA2834901A patent/CA2834901A1/en not_active Abandoned
- 2012-05-02 WO PCT/EP2012/058046 patent/WO2012152629A1/de not_active Ceased
- 2012-05-02 CN CN201280033572.9A patent/CN103649093B/zh not_active Expired - Fee Related
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| US8765769B2 (en) | 2010-07-09 | 2014-07-01 | Bayer Intellectual Property Gmbh | Ring-fused 4-aminopyrimidines and use thereof as stimulators of soluable guanylate cyclases |
| US9216978B2 (en) | 2010-07-09 | 2015-12-22 | Bayer Intellectual Property Gmbh | Ring-fused pyrimidines and triazines and use thereof for the treatment and/or prophylaxis of cardiovascular diseases |
| US9096592B2 (en) | 2010-09-03 | 2015-08-04 | Bayer Intellectual Property Gmbh | Bicyclic aza heterocycles, and use thereof |
| US9090610B2 (en) | 2011-04-21 | 2015-07-28 | Bayer Intellectual Property Gmbh | Fluoroalkyl-substituted pyrazolopyridines and use thereof |
| US8859569B2 (en) | 2011-09-02 | 2014-10-14 | Bayer Pharma Aktiengesellschaft | Substituted annellated pyrimidines and use thereof |
| US9023849B2 (en) | 2012-01-11 | 2015-05-05 | Bayer Intellectual Property Gmbh | Substituted fused imidazoles and pyrazoles and use thereof |
| US9133191B2 (en) | 2012-01-11 | 2015-09-15 | Bayer Intellectual Property Gmbh | Substituted triazine derivatives and use thereof as stimulators of soluble guanylate cyclase |
| US9505786B2 (en) | 2012-01-11 | 2016-11-29 | Bayer Pharma Aktiengesellschaft | Substituted annulated triazines and use thereof |
| US9498480B2 (en) | 2012-03-06 | 2016-11-22 | Bayer Intellectual Property Gmbh | Substituted azabicycles and use thereof |
| US9266871B2 (en) | 2013-03-01 | 2016-02-23 | Bayer Pharma Aktiengesellschaft | Trifluoromethyl-substituted fused pyrimidines and their use |
| US9605008B2 (en) | 2013-07-10 | 2017-03-28 | Bayer Pharma Aktiengesellschaft | Benzyl-1H-pyrazolo[3,4-b]pyridines and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012152629A1 (de) | 2012-11-15 |
| JP2014513112A (ja) | 2014-05-29 |
| ES2592267T3 (es) | 2016-11-29 |
| JP5976788B2 (ja) | 2016-08-24 |
| US20140171434A1 (en) | 2014-06-19 |
| EP2705037A1 (de) | 2014-03-12 |
| EP2705037B1 (de) | 2016-06-22 |
| CN103649093A (zh) | 2014-03-19 |
| CN103649093B (zh) | 2017-07-07 |
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