HRP20120334T1 - Supstituirani piperidino-dihidrotienopirimidini - Google Patents
Supstituirani piperidino-dihidrotienopirimidini Download PDFInfo
- Publication number
- HRP20120334T1 HRP20120334T1 HRP20120334AT HRP20120334T HRP20120334T1 HR P20120334 T1 HRP20120334 T1 HR P20120334T1 HR P20120334A T HRP20120334A T HR P20120334AT HR P20120334 T HRP20120334 T HR P20120334T HR P20120334 T1 HRP20120334 T1 HR P20120334T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- ethyl
- alkylene
- methylene
- phenyl
- Prior art date
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- JMUGMZBGUVOSPU-UHFFFAOYSA-N 1-piperidin-1-yl-2h-thieno[3,2-d]pyrimidine Chemical class C1CCCCN1N1C(C=CS2)=C2C=NC1 JMUGMZBGUVOSPU-UHFFFAOYSA-N 0.000 title 1
- -1 -het Chemical group 0.000 claims abstract 88
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 55
- 150000001875 compounds Chemical class 0.000 claims abstract 52
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 49
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims abstract 48
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims abstract 48
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims abstract 48
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims abstract 47
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 41
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 41
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 31
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 30
- 125000005842 heteroatom Chemical group 0.000 claims abstract 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract 19
- 150000002367 halogens Chemical class 0.000 claims abstract 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 19
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 17
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 133
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 61
- 239000005977 Ethylene Substances 0.000 claims 58
- 229910052731 fluorine Inorganic materials 0.000 claims 57
- 229910052801 chlorine Inorganic materials 0.000 claims 56
- 239000000460 chlorine Substances 0.000 claims 56
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 56
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 55
- 150000003839 salts Chemical class 0.000 claims 44
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 43
- 150000004677 hydrates Chemical class 0.000 claims 43
- 239000012453 solvate Substances 0.000 claims 43
- 229910052794 bromium Inorganic materials 0.000 claims 39
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 39
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 9
- 239000011737 fluorine Substances 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- OPKQXJQFEPNJTP-UHFFFAOYSA-N 1-phenylpropa-1,2-dienylbenzene Chemical group C=1C=CC=CC=1C(=C=C)C1=CC=CC=C1 OPKQXJQFEPNJTP-UHFFFAOYSA-N 0.000 claims 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 claims 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 208000028683 bipolar I disease Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 230000002093 peripheral effect Effects 0.000 claims 2
- 210000001428 peripheral nervous system Anatomy 0.000 claims 2
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 230000000241 respiratory effect Effects 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
- CXIPCVGKMMYCCL-UHFFFAOYSA-N 1-cyclopropylpropa-1,2-dienylcyclopropane Chemical group C1CC1C(=C=C)C1CC1 CXIPCVGKMMYCCL-UHFFFAOYSA-N 0.000 claims 1
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims 1
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims 1
- KDYWHKGSKGUIQO-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-2h-1,2-benzoxazine Chemical compound C1C=CC=C2ONCCC21 KDYWHKGSKGUIQO-UHFFFAOYSA-N 0.000 claims 1
- BGDOLELXXPTPFX-UHFFFAOYSA-N 3,4-dihydro-2h-1,2-benzoxazine Chemical compound C1=CC=C2ONCCC2=C1 BGDOLELXXPTPFX-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010009137 Chronic sinusitis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- NTURVSFTOYPGON-UHFFFAOYSA-N Dihydroquinazoline Chemical compound C1=CC=C2C=NCNC2=C1 NTURVSFTOYPGON-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 239000000808 adrenergic beta-agonist Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 1
- 230000003454 betamimetic effect Effects 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 208000025307 bipolar depression Diseases 0.000 claims 1
- 230000006931 brain damage Effects 0.000 claims 1
- 231100000874 brain damage Toxicity 0.000 claims 1
- 208000029028 brain injury Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 229940121647 egfr inhibitor Drugs 0.000 claims 1
- YIWFBNMYFYINAD-UHFFFAOYSA-N ethenylcyclopropane Chemical group C=CC1CC1 YIWFBNMYFYINAD-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003843 mucus production Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- DTHHUAXKOMWYBI-UHFFFAOYSA-N oxadiazolidine Chemical compound C1CONN1 DTHHUAXKOMWYBI-UHFFFAOYSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- 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
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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Applications Claiming Priority (2)
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EP07118901 | 2007-10-19 | ||
PCT/EP2008/063999 WO2009050248A1 (de) | 2007-10-19 | 2008-10-16 | Substituierte piperidino-dihydrothienopyrimidine |
Publications (1)
Publication Number | Publication Date |
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HRP20120334T1 true HRP20120334T1 (hr) | 2012-05-31 |
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HRP20120334AT HRP20120334T1 (hr) | 2007-10-19 | 2012-04-16 | Supstituirani piperidino-dihidrotienopirimidini |
HRP20141153AT HRP20141153T1 (hr) | 2007-10-19 | 2014-11-26 | Supstituirani piperidino-dihidrotieno-pirimidini |
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HRP20141153AT HRP20141153T1 (hr) | 2007-10-19 | 2014-11-26 | Supstituirani piperidino-dihidrotieno-pirimidini |
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US (1) | US8754073B2 (da) |
EP (3) | EP2215092B1 (da) |
JP (2) | JP5150728B2 (da) |
KR (1) | KR101548975B1 (da) |
CN (2) | CN101827852B (da) |
AR (1) | AR069075A1 (da) |
AT (1) | ATE542825T1 (da) |
AU (1) | AU2008313660B2 (da) |
BR (1) | BRPI0818006B8 (da) |
CA (1) | CA2705414C (da) |
CL (1) | CL2008003096A1 (da) |
CY (2) | CY1112703T1 (da) |
DK (2) | DK2610258T3 (da) |
EA (1) | EA019480B1 (da) |
EC (1) | ECSP10010156A (da) |
ES (2) | ES2524910T3 (da) |
HK (1) | HK1145677A1 (da) |
HR (2) | HRP20120334T1 (da) |
MA (1) | MA31845B1 (da) |
ME (1) | ME01330B (da) |
MX (1) | MX2010004026A (da) |
MY (1) | MY153979A (da) |
NZ (1) | NZ585346A (da) |
PE (2) | PE20091386A1 (da) |
PL (2) | PL2610258T3 (da) |
PT (2) | PT2215092E (da) |
RS (1) | RS52271B (da) |
SI (2) | SI2610258T1 (da) |
TN (1) | TN2010000175A1 (da) |
TW (1) | TWI421077B (da) |
UA (1) | UA99309C2 (da) |
UY (1) | UY31405A1 (da) |
WO (1) | WO2009050248A1 (da) |
ZA (1) | ZA201001683B (da) |
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EP2215092B1 (de) * | 2007-10-19 | 2012-01-25 | Boehringer Ingelheim International GmbH | Substituierte piperidino-dihydrothienopyrimidine |
CA2702524A1 (en) | 2007-10-19 | 2009-04-23 | Boehringer Ingelheim International Gmbh | Heterocycle-substituted piperazino-dihydrothienopyrimidines |
WO2009050236A1 (de) | 2007-10-19 | 2009-04-23 | Boehringer Ingelheim International Gmbh | Neue piperazino-dihydrothienopyrimidin-derivate |
WO2010097334A1 (de) * | 2009-02-27 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Arzneimittelkombinationen enthaltend pde4-inhibitoren und nsaids |
WO2011124525A1 (de) | 2010-04-08 | 2011-10-13 | Boehringer Ingelheim International Gmbh | Arnzeimittelkombinationen enthaltend pde4-inhibitoren und ep4-rezeptor-antagonisten |
JP2013529184A (ja) | 2010-04-08 | 2013-07-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Pde4阻害剤及びep4受容体アンタゴニストを含有する医薬の組み合わせ |
WO2011143057A1 (en) | 2010-05-11 | 2011-11-17 | Merck Sharp & Dohme Corp. | Novel prolylcarboxypeptidase inhibitors |
US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
US9802954B2 (en) | 2011-08-24 | 2017-10-31 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
US9013997B2 (en) | 2012-06-01 | 2015-04-21 | Broadcom Corporation | System for performing distributed data cut-through |
US9499519B2 (en) | 2012-12-26 | 2016-11-22 | Medivation Technologies, Inc. | Fused pyrimidine compounds and use thereof |
MX2015009677A (es) * | 2013-02-04 | 2015-11-25 | Gruenenthal Gmbh | Compuestos de pirimidina condensada sustituida novedosos. |
WO2014124860A1 (en) | 2013-02-14 | 2014-08-21 | Boehringer Ingelheim International Gmbh | Specific pde4b-inhibitors for the treatment of diabetes mellitus |
HUP1300139A2 (en) * | 2013-03-06 | 2014-09-29 | Richter Gedeon Nyrt | Phenoxypiperidine h3 antagonists |
CN104892720B (zh) * | 2014-03-07 | 2016-10-26 | 华东师范大学 | 4,4-二甲基石胆酸-2,3-骈n-芳基吡唑衍生物及其制备方法和应用 |
ES2874185T3 (es) * | 2016-06-30 | 2021-11-04 | Riken | Nuevo compuesto o una sal farmacéuticamente aceptable del mismo |
US11365204B2 (en) | 2017-09-20 | 2022-06-21 | UNION therapeutics A/S | Substituted dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
MX2020004173A (es) | 2017-10-23 | 2020-08-03 | Boehringer Ingelheim Int | Nueva combinacion de agentes activos para el tratamiento de enfermedades pulmonares intersticiales fibrosantes progresivas (pf-ild). |
EP3724196B9 (en) | 2017-12-15 | 2023-03-22 | UNION therapeutics A/S | Substituted azetidine dihydrothienopyridines and their use as phosphodiesterase inhibitors |
US11292799B2 (en) | 2017-12-15 | 2022-04-05 | UNION therapeutics A/S | Substituted azetidine dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
US11299497B2 (en) | 2017-12-15 | 2022-04-12 | UNION therapeutics A/S | Substituted tetrahydropyran dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
WO2020048827A1 (en) * | 2018-09-03 | 2020-03-12 | Bayer Aktiengesellschaft | 1, 3, 9-triazaspiro[5.5] undecan-2-one compounds |
US20230190754A1 (en) | 2021-12-09 | 2023-06-22 | Boehringer Ingelheim International Gmbh | Therapeutic combinations for the treatment of Progressive Fibrosing interstitial lung diseases |
US20230181590A1 (en) | 2021-12-09 | 2023-06-15 | Boehringer Ingelheim International Gmbh | New oral pharmaceutical composition and dose regimen for the therapy of progressive fibrosing interstitial lung diseases |
WO2023232135A1 (zh) * | 2022-06-02 | 2023-12-07 | 西藏海思科制药有限公司 | Pde4b抑制剂及其用途 |
WO2023241684A1 (zh) * | 2022-06-16 | 2023-12-21 | 武汉人福创新药物研发中心有限公司 | Pde4b抑制剂 |
CN115040503B (zh) * | 2022-07-26 | 2023-10-10 | 云南民族大学 | 螺环二烯酮型木脂素类化合物在制药中的应用 |
WO2024032673A1 (zh) * | 2022-08-09 | 2024-02-15 | 西藏海思科制药有限公司 | Pde4b抑制剂及其用途 |
WO2024068386A1 (en) | 2022-09-28 | 2024-04-04 | Boehringer Ingelheim International Gmbh | Use of biomarkers in the treatment of fibrotic conditions with a pde4b-inhibitor |
WO2024067660A1 (zh) * | 2022-09-29 | 2024-04-04 | 苏州爱科百发生物医药技术有限公司 | 氮杂稠环类化合物、其制备方法及其在医药上的应用 |
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-
2008
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2010
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- 2010-05-05 EC EC2010010156A patent/ECSP10010156A/es unknown
- 2010-05-12 MA MA32832A patent/MA31845B1/fr unknown
- 2010-12-22 HK HK10111978.1A patent/HK1145677A1/xx not_active IP Right Cessation
-
2012
- 2012-04-16 HR HRP20120334AT patent/HRP20120334T1/hr unknown
- 2012-04-23 CY CY20121100378T patent/CY1112703T1/el unknown
- 2012-12-03 JP JP2012264647A patent/JP5615889B2/ja active Active
-
2014
- 2014-11-26 HR HRP20141153AT patent/HRP20141153T1/hr unknown
- 2014-11-26 CY CY20141100984T patent/CY1115858T1/el unknown
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