CA2784013A1 - 3,4,4a,10b-tetrahydro-1h-thiopyrano-[4, 3-c] isoquinoline derivatives - Google Patents
3,4,4a,10b-tetrahydro-1h-thiopyrano-[4, 3-c] isoquinoline derivatives Download PDFInfo
- Publication number
- CA2784013A1 CA2784013A1 CA2784013A CA2784013A CA2784013A1 CA 2784013 A1 CA2784013 A1 CA 2784013A1 CA 2784013 A CA2784013 A CA 2784013A CA 2784013 A CA2784013 A CA 2784013A CA 2784013 A1 CA2784013 A1 CA 2784013A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- ethyl
- oxadiazol
- compound
- phenyl
- 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
- ZQCSTHXMOLTGJA-UHFFFAOYSA-N 3,4,4a,10b-tetrahydro-1h-thiopyrano[4,3-c]isoquinoline Chemical class N1=CC2=CC=CC=C2C2C1CCSC2 ZQCSTHXMOLTGJA-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 709
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims abstract description 19
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims abstract description 19
- -1 pyrazol-4-yl Chemical group 0.000 claims description 794
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 170
- 238000000034 method Methods 0.000 claims description 111
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 69
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 63
- 229910052717 sulfur Inorganic materials 0.000 claims description 61
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 51
- 201000010099 disease Diseases 0.000 claims description 43
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims description 32
- 239000011737 fluorine Substances 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 23
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 23
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
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- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 5
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- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 4
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims description 3
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 3
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 3
- 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 claims description 3
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 3
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 3
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 3
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 3
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 3
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- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims 2
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Classifications
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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
-
- 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
-
- 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
- A61K31/495—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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- 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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| CN103501776A (zh) * | 2011-02-17 | 2014-01-08 | 西普拉有限公司 | 甘罗铵与β2激动剂的组合物 |
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| US20150322049A1 (en) * | 2012-12-13 | 2015-11-12 | Ludwig Aigner | Leukotriene pathway antagonists for the treatment of dementia, cognitive deficits in parkinson's disease and/or learning and memory deficiencies in parkinson's disease |
| CA2899962A1 (en) | 2013-02-04 | 2014-08-07 | Grunenthal Gmbh | 3-substituted pyrazoles and use as dlk inhibitors4-amino substituted condensed pyrimidine compounds as pde4 inhibitors |
| MA38333A1 (fr) | 2013-02-19 | 2017-02-28 | Pfizer | Composés d'azabenzimidazole en tant qu'inhibiteurs d'isozymes pde4 pour le traitement de troubles du snc et d'autres affections |
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| WO2022006470A1 (en) | 2020-07-01 | 2022-01-06 | Vanderbilt University | Methods of treatment for a kidney disease |
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| FZDE | Discontinued |
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