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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- A—HUMAN NECESSITIES
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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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- Chemical & Material Sciences (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07118901 | 2007-10-19 | ||
| PCT/EP2008/063999 WO2009050248A1 (de) | 2007-10-19 | 2008-10-16 | Substituierte piperidino-dihydrothienopyrimidine |
Publications (1)
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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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| SI (2) | SI2215092T1 (pt) |
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| TW (1) | TWI421077B (pt) |
| UA (1) | UA99309C2 (pt) |
| UY (1) | UY31405A1 (pt) |
| WO (1) | WO2009050248A1 (pt) |
| ZA (1) | ZA201001683B (pt) |
Families Citing this family (32)
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| EP1847543A1 (de) | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen |
| US8653282B2 (en) | 2007-10-18 | 2014-02-18 | Boehringer Ingelheim International Gmbh | Preparation of dihydrothieno [3,2-D] pyrimidines and intermediates used therein |
| CA2705414C (en) * | 2007-10-19 | 2016-05-24 | Boehringer Ingelheim International Gmbh | Substituted piperidino-dihydrothienopyrimidines |
| WO2009050236A1 (de) | 2007-10-19 | 2009-04-23 | Boehringer Ingelheim International Gmbh | Neue piperazino-dihydrothienopyrimidin-derivate |
| CN101827853A (zh) | 2007-10-19 | 2010-09-08 | 贝林格尔.英格海姆国际有限公司 | 杂环取代的哌嗪子基-二氢噻吩并嘧啶 |
| CA2753604A1 (en) * | 2009-02-27 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Drug combinations containing pde4-inhibitors and nsaids |
| WO2011124524A1 (de) | 2010-04-08 | 2011-10-13 | Boehringer Ingelheim International Gmbh | Arzneimittelkombinationen enthaltend pde4-inhibitoren und ep4-rezeptor-antagonisten |
| EP2555774B1 (de) | 2010-04-08 | 2015-10-21 | Boehringer Ingelheim International GmbH | Arnzeimittelkombinationen enthaltend pde4-inhibitoren und ep4-rezeptor-antagonisten |
| US9365539B2 (en) | 2010-05-11 | 2016-06-14 | Merck Sharp & Dohme Corp. | 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 |
| WO2014117948A1 (en) * | 2013-02-04 | 2014-08-07 | Grünenthal GmbH | Novel substituted condensed pyrimidine compounds |
| 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 |
| WO2018003962A1 (ja) * | 2016-06-30 | 2018-01-04 | 国立研究開発法人理化学研究所 | 新規化合物又はその薬理学的に許容される塩 |
| CN111108109A (zh) | 2017-09-20 | 2020-05-05 | 利奥制药有限公司 | 取代的二氢噻吩并嘧啶及其作为磷酸二酯酶抑制剂的用途 |
| EA202090977A1 (ru) | 2017-10-23 | 2020-09-04 | Бёрингер Ингельхайм Интернациональ Гмбх | Новая комбинация активных агентов для лечения прогрессирующих фиброзирующих интерстициальных заболеваний легких (pf-ild) |
| ES2935615T3 (es) | 2017-12-15 | 2023-03-08 | Union Therapeutics As | Azetidina dihidrotienopiridinas sustituidas y su uso como inhibidores de la fosfodiesterasa |
| WO2019115774A1 (en) | 2017-12-15 | 2019-06-20 | Leo Pharma A/S | Substituted azetidine dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| WO2019115775A1 (en) | 2017-12-15 | 2019-06-20 | Leo Pharma 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 |
| TW202339731A (zh) | 2021-12-09 | 2023-10-16 | 德商百靈佳殷格翰國際股份有限公司 | 用於治療進行性纖維化間質性肺病之新穎口服醫藥組合物及劑量療法 |
| 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 |
| CN117247395A (zh) * | 2022-06-16 | 2023-12-19 | 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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| BE663693A (pt) | 1965-03-31 | |||
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| CA2753604A1 (en) | 2009-02-27 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Drug combinations containing pde4-inhibitors and nsaids |
| EP2400961B1 (de) | 2009-02-27 | 2017-11-22 | Boehringer Ingelheim International GmbH | Arzneimittelkombinationen enthaltend pde4-inhibitoren und nsaids |
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