RU2008119323A - Фармацевтические композиции мускаринового рецептора - Google Patents
Фармацевтические композиции мускаринового рецептора Download PDFInfo
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- RU2008119323A RU2008119323A RU2008119323/15A RU2008119323A RU2008119323A RU 2008119323 A RU2008119323 A RU 2008119323A RU 2008119323/15 A RU2008119323/15 A RU 2008119323/15A RU 2008119323 A RU2008119323 A RU 2008119323A RU 2008119323 A RU2008119323 A RU 2008119323A
- Authority
- RU
- Russia
- Prior art keywords
- compound
- dioxa
- azaspiro
- ene
- phenyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 6
- UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical group C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 411
- -1 cyano, hydroxy Chemical group 0.000 claims abstract 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract 31
- 150000002148 esters Chemical class 0.000 claims abstract 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract 15
- 150000002367 halogens Chemical class 0.000 claims abstract 15
- 239000001257 hydrogen Substances 0.000 claims abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 15
- 239000001301 oxygen Substances 0.000 claims abstract 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 11
- 125000003118 aryl group Chemical group 0.000 claims abstract 11
- 239000011593 sulfur Chemical group 0.000 claims abstract 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 11
- 150000001412 amines Chemical class 0.000 claims abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 8
- 150000001204 N-oxides Chemical class 0.000 claims abstract 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract 7
- 239000002207 metabolite Substances 0.000 claims abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 7
- 229910052757 nitrogen Chemical group 0.000 claims abstract 7
- 239000012453 solvate Substances 0.000 claims abstract 7
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 5
- 239000000651 prodrug Substances 0.000 claims abstract 5
- 229940002612 prodrug Drugs 0.000 claims abstract 5
- 125000001424 substituent group Chemical group 0.000 claims abstract 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims abstract 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 3
- 101150030891 MRAS gene Proteins 0.000 claims abstract 3
- 239000005557 antagonist Substances 0.000 claims abstract 3
- 239000000043 antiallergic agent Substances 0.000 claims abstract 3
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims abstract 3
- 229940124748 beta 2 agonist Drugs 0.000 claims abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims abstract 3
- 239000000812 cholinergic antagonist Substances 0.000 claims abstract 3
- 239000003246 corticosteroid Substances 0.000 claims abstract 3
- 229960001334 corticosteroids Drugs 0.000 claims abstract 3
- 229940052760 dopamine agonists Drugs 0.000 claims abstract 3
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims abstract 3
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims abstract 3
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims abstract 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 3
- 239000011737 fluorine Substances 0.000 claims abstract 3
- 239000011630 iodine Substances 0.000 claims abstract 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract 3
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims abstract 3
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 3
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims abstract 3
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims abstract 3
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract 3
- 239000013312 porous aromatic framework Substances 0.000 claims abstract 3
- 229940043355 kinase inhibitor Drugs 0.000 claims abstract 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims abstract 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 15
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 7
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 6
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 229960001867 guaiacol Drugs 0.000 claims 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 4
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 150000003892 tartrate salts Chemical class 0.000 claims 4
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 3
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 3
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 3
- CVSWUEXZWSBDMC-UHFFFAOYSA-N non-2-ene Chemical compound CCCCCC[CH]C=C CVSWUEXZWSBDMC-UHFFFAOYSA-N 0.000 claims 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims 2
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 2
- YWWQABBXZSDJEK-UHFFFAOYSA-N 3-(3-cycloheptyloxy-4-cyclopentyloxyphenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound C1CCCC1OC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OC1CCCCCC1 YWWQABBXZSDJEK-UHFFFAOYSA-N 0.000 claims 2
- DXKVMSIONQYWOY-UHFFFAOYSA-N 3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2-azaspiro[4.5]dec-2-en-8-ol Chemical compound COC1=CC=C(C=2CC3(ON=2)CCC(O)CC3)C=C1OC1CCCC1 DXKVMSIONQYWOY-UHFFFAOYSA-N 0.000 claims 2
- JNJZDZZUUFIKSD-UHFFFAOYSA-N 3-[3-(cyclopropylmethoxy)-4-propan-2-yloxyphenyl]-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound CC(C)OC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OCC1CC1 JNJZDZZUUFIKSD-UHFFFAOYSA-N 0.000 claims 2
- KKFCQSQFZILURW-FVRDMJKUSA-N 3-[4-(difluoromethoxy)-3-[[(2s)-pyrrolidin-2-yl]methoxy]phenyl]-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound FC(F)OC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OC[C@@H]1CCCN1 KKFCQSQFZILURW-FVRDMJKUSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 239000011975 tartaric acid Substances 0.000 claims 2
- 235000002906 tartaric acid Nutrition 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- DPVJZWJFXGRGJO-SFHVURJKSA-N (5r)-3-(3-cyclopentyloxy-4-methoxyphenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound COC1=CC=C(C=2C[C@@]3(COCC3)ON=2)C=C1OC1CCCC1 DPVJZWJFXGRGJO-SFHVURJKSA-N 0.000 claims 1
- DPVJZWJFXGRGJO-GOSISDBHSA-N (5s)-3-(3-cyclopentyloxy-4-methoxyphenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound COC1=CC=C(C=2C[C@]3(COCC3)ON=2)C=C1OC1CCCC1 DPVJZWJFXGRGJO-GOSISDBHSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 claims 1
- VTIRXKHOOLRNDQ-OOJLDXBWSA-N 1-[(2s)-2-[[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1COC1=CC(C=2CC3(COCC3)ON=2)=CC=C1OC(F)F VTIRXKHOOLRNDQ-OOJLDXBWSA-N 0.000 claims 1
- QXCFQUOIWNHMJB-UHFFFAOYSA-N 1-[3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-en-7-yl]ethanone Chemical compound COC1=CC=C(C=2CC3(CN(CC3)C(C)=O)ON=2)C=C1OC1CCCC1 QXCFQUOIWNHMJB-UHFFFAOYSA-N 0.000 claims 1
- KQNRZHISYIUFFD-UHFFFAOYSA-N 1-[3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]ethanone Chemical compound COC1=CC=C(C=2CC3(ON=2)CCN(CC3)C(C)=O)C=C1OC1CCCC1 KQNRZHISYIUFFD-UHFFFAOYSA-N 0.000 claims 1
- JQTSMCFPUBMDPZ-UHFFFAOYSA-N 1-[3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,9-diazaspiro[4.5]dec-2-en-9-yl]ethanone Chemical compound COC1=CC=C(C=2CC3(ON=2)CN(CCC3)C(C)=O)C=C1OC1CCCC1 JQTSMCFPUBMDPZ-UHFFFAOYSA-N 0.000 claims 1
- RPGKESJJHALPAH-UHFFFAOYSA-N 1-[3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2-azaspiro[4.5]dec-2-en-8-yl]-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1CCC2(ON=C(C2)C=2C=C(OC3CCCC3)C(OC)=CC=2)CC1 RPGKESJJHALPAH-UHFFFAOYSA-N 0.000 claims 1
- KMFUVVRLBOYMAY-UHFFFAOYSA-N 1-[3-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1OC1=CC(C=2CC3(COCC3)ON=2)=CC=C1OC(F)F KMFUVVRLBOYMAY-UHFFFAOYSA-N 0.000 claims 1
- NXTVNOKGNYDNBY-UHFFFAOYSA-N 1-[3-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]piperidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCCC1OC1=CC(C=2CC3(COCC3)ON=2)=CC=C1OC(F)F NXTVNOKGNYDNBY-UHFFFAOYSA-N 0.000 claims 1
- JAJTVVDBPOVKQM-UHFFFAOYSA-N 1-[4-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1OC1=CC(C=2CC3(COCC3)ON=2)=CC=C1OC(F)F JAJTVVDBPOVKQM-UHFFFAOYSA-N 0.000 claims 1
- LECHGRBFRSCYPJ-UHFFFAOYSA-N 1-[4-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCC1OC1=CC(C=2CC3(COCC3)ON=2)=CC=C1OC(F)F LECHGRBFRSCYPJ-UHFFFAOYSA-N 0.000 claims 1
- MRKIOAZSDBZENQ-UHFFFAOYSA-N 1-butyl-3-[3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2-azaspiro[4.5]dec-2-en-8-yl]urea Chemical compound C1CC(NC(=O)NCCCC)CCC11ON=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C1 MRKIOAZSDBZENQ-UHFFFAOYSA-N 0.000 claims 1
- YPRHEPKTGFUHCK-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-yloxy)-4-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenol Chemical compound C1=C(OC2CC3=CC=CC=C3C2)C(O)=CC=C1C(C1)=NOC21CCOC2 YPRHEPKTGFUHCK-UHFFFAOYSA-N 0.000 claims 1
- HUPVBFQYJHFONM-UHFFFAOYSA-N 2-(4-fluorophenyl)acetamide Chemical compound NC(=O)CC1=CC=C(F)C=C1 HUPVBFQYJHFONM-UHFFFAOYSA-N 0.000 claims 1
- MOWKSKDNBFDKRV-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]acetonitrile Chemical compound C1=C(OCC#N)C(OC(F)F)=CC=C1C(C1)=NOC11COCC1 MOWKSKDNBFDKRV-UHFFFAOYSA-N 0.000 claims 1
- FGMJOLZIJYUYRN-UHFFFAOYSA-N 2-[5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)-2-methoxyphenoxy]acetamide Chemical compound C1=C(OCC(N)=O)C(OC)=CC=C1C(C1)=NOC11COCC1 FGMJOLZIJYUYRN-UHFFFAOYSA-N 0.000 claims 1
- PJTOVCQEWMEDFI-UHFFFAOYSA-N 2-[5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)-2-methoxyphenoxy]acetonitrile Chemical compound C1=C(OCC#N)C(OC)=CC=C1C(C1)=NOC11COCC1 PJTOVCQEWMEDFI-UHFFFAOYSA-N 0.000 claims 1
- GMNDCMQPBWZHLK-UHFFFAOYSA-N 2-[5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)-2-methoxyphenoxy]cyclopentan-1-ol Chemical compound COC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OC1CCCC1O GMNDCMQPBWZHLK-UHFFFAOYSA-N 0.000 claims 1
- NNCQRRYTAYEFDO-UHFFFAOYSA-N 2-cyclopentyloxy-4-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenol Chemical compound OC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OC1CCCC1 NNCQRRYTAYEFDO-UHFFFAOYSA-N 0.000 claims 1
- UPTMVIKIZMEHFW-UHFFFAOYSA-N 3-(3,4-dicyclopentyloxyphenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound C1CCCC1OC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OC1CCCC1 UPTMVIKIZMEHFW-UHFFFAOYSA-N 0.000 claims 1
- NAGHGSBKEYNIAA-UHFFFAOYSA-N 3-(3-butoxy-4-cyclohexyloxyphenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound CCCCOC1=CC(C=2CC3(COCC3)ON=2)=CC=C1OC1CCCCC1 NAGHGSBKEYNIAA-UHFFFAOYSA-N 0.000 claims 1
- GKFDYDIBPWPJDH-UHFFFAOYSA-N 3-(3-butoxy-4-cyclopentyloxyphenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound CCCCOC1=CC(C=2CC3(COCC3)ON=2)=CC=C1OC1CCCC1 GKFDYDIBPWPJDH-UHFFFAOYSA-N 0.000 claims 1
- VSHYHRWYSGFZIM-UHFFFAOYSA-N 3-(3-butoxy-4-ethoxyphenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound C1=C(OCC)C(OCCCC)=CC(C=2CC3(COCC3)ON=2)=C1 VSHYHRWYSGFZIM-UHFFFAOYSA-N 0.000 claims 1
- UEIBXNATDIOJQT-UHFFFAOYSA-N 3-(3-butoxy-4-propan-2-yloxyphenyl)-1,7-dioxa-2-azaspiro[4.4]non-2-ene Chemical compound C1=C(OC(C)C)C(OCCCC)=CC(C=2CC3(COCC3)ON=2)=C1 UEIBXNATDIOJQT-UHFFFAOYSA-N 0.000 claims 1
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- ITBSVYDQYCMHMW-UHFFFAOYSA-N 7-amino-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-en-6-one Chemical compound COC1=CC=C(C=2CC3(C(N(N)CC3)=O)ON=2)C=C1OC1CCCC1 ITBSVYDQYCMHMW-UHFFFAOYSA-N 0.000 claims 1
- SVJYUTVNJHMTRG-UHFFFAOYSA-N 8-benzyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene Chemical compound COC1=CC=C(C=2CC3(ON=2)CCN(CC=2C=CC=CC=2)CC3)C=C1OC1CCCC1 SVJYUTVNJHMTRG-UHFFFAOYSA-N 0.000 claims 1
- DZYHDPWVQXHZSS-UHFFFAOYSA-N Cl.C1(CCCC1)OC=1C=C(C=CC1OC)C1=NOC2(C1)CCN(CC2)CCC Chemical compound Cl.C1(CCCC1)OC=1C=C(C=CC1OC)C1=NOC2(C1)CCN(CC2)CCC DZYHDPWVQXHZSS-UHFFFAOYSA-N 0.000 claims 1
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- OGJQMTWBMNSECG-VEXWJQHLSA-N [(3s)-3-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]pyrrolidin-1-yl]-phenylmethanone Chemical compound C([C@@H](C1)OC2=CC(=CC=C2OC(F)F)C=2CC3(COCC3)ON=2)CN1C(=O)C1=CC=CC=C1 OGJQMTWBMNSECG-VEXWJQHLSA-N 0.000 claims 1
- JTKZNDWRAHGHLN-UHFFFAOYSA-N [3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-en-7-yl]-(oxolan-3-yl)methanone Chemical compound COC1=CC=C(C=2CC3(CN(CC3)C(=O)C3COCC3)ON=2)C=C1OC1CCCC1 JTKZNDWRAHGHLN-UHFFFAOYSA-N 0.000 claims 1
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- DHCBDZBAOMEZQE-UHFFFAOYSA-N cyclopentyl-[3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,9-diazaspiro[4.5]dec-2-en-9-yl]methanone Chemical compound COC1=CC=C(C=2CC3(ON=2)CN(CCC3)C(=O)C2CCCC2)C=C1OC1CCCC1 DHCBDZBAOMEZQE-UHFFFAOYSA-N 0.000 claims 1
- PJSADAFDKGDXMW-UHFFFAOYSA-N cyclopentyl-[3-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]piperidin-1-yl]methanone Chemical compound FC(F)OC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OC(C1)CCCN1C(=O)C1CCCC1 PJSADAFDKGDXMW-UHFFFAOYSA-N 0.000 claims 1
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- DBBHOJIBWCTKFC-UHFFFAOYSA-N ethyl 3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2-azaspiro[4.5]dec-2-ene-4-carboxylate Chemical compound CCOC(=O)C1C(C=2C=C(OC3CCCC3)C(OC)=CC=2)=NOC11CCCCC1 DBBHOJIBWCTKFC-UHFFFAOYSA-N 0.000 claims 1
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- PPJGSQYDBPIBAZ-UHFFFAOYSA-N n-benzyl-2-[5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)-2-(2,2,2-trifluoroethoxy)phenoxy]acetamide Chemical compound FC(F)(F)COC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OCC(=O)NCC1=CC=CC=C1 PPJGSQYDBPIBAZ-UHFFFAOYSA-N 0.000 claims 1
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- JIUBDOYSGTZBGJ-UHFFFAOYSA-N n-butyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,9-diazaspiro[4.5]dec-2-ene-9-carboxamide Chemical compound C1N(C(=O)NCCCC)CCCC11ON=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C1 JIUBDOYSGTZBGJ-UHFFFAOYSA-N 0.000 claims 1
- SQCSYQVNDCMRCE-UHFFFAOYSA-N n-cyclopentyl-2-[5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)-2-(2,2,2-trifluoroethoxy)phenoxy]acetamide Chemical compound FC(F)(F)COC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OCC(=O)NC1CCCC1 SQCSYQVNDCMRCE-UHFFFAOYSA-N 0.000 claims 1
- CBEJRQJYGPDALT-UHFFFAOYSA-N n-cyclopropyl-2-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]acetamide Chemical compound FC(F)OC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OCC(=O)NC1CC1 CBEJRQJYGPDALT-UHFFFAOYSA-N 0.000 claims 1
- MBVRPQATEATQRS-UHFFFAOYSA-N n-cyclopropyl-2-[5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)-2-(2,2,2-trifluoroethoxy)phenoxy]acetamide Chemical compound FC(F)(F)COC1=CC=C(C=2CC3(COCC3)ON=2)C=C1OCC(=O)NC1CC1 MBVRPQATEATQRS-UHFFFAOYSA-N 0.000 claims 1
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- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
- OMVVJADQPFQYKT-UEDXYCIISA-N tert-butyl (3s)-3-[2-(difluoromethoxy)-5-(1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl)phenoxy]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@@H]1OC1=CC(C=2CC3(COCC3)ON=2)=CC=C1OC(F)F OMVVJADQPFQYKT-UEDXYCIISA-N 0.000 claims 1
- UUXULYLAARCZOB-UHFFFAOYSA-N tert-butyl 3-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxa-2,9-diazaspiro[4.5]dec-2-ene-9-carboxylate Chemical compound COC1=CC=C(C=2CC3(ON=2)CN(CCC3)C(=O)OC(C)(C)C)C=C1OC1CCCC1 UUXULYLAARCZOB-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
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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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- A61P17/00—Drugs for dermatological disorders
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- 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
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
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- Epidemiology (AREA)
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- Oncology (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| RU2008119323/15A RU2008119323A (ru) | 2005-10-19 | 2006-10-19 | Фармацевтические композиции мускаринового рецептора |
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| US20080009535A1 (en) * | 2004-08-30 | 2008-01-10 | Sarala Balachandran | Inhibitors of phosphodiesterase type-IV |
| EP2059505A2 (en) * | 2006-09-04 | 2009-05-20 | Ranbaxy Laboratories Limited | Muscarinic receptor antagonists |
| EA200900472A1 (ru) * | 2006-09-22 | 2009-10-30 | Ранбакси Лабораторис Лимитед | Ингибиторы фосфодиэстеразы iv типа |
| US20100152269A1 (en) * | 2006-12-21 | 2010-06-17 | Ranbaxy Laboratories Limited | Modified-release formulations of azabicyclo derivatives |
| EP2111861A1 (en) * | 2008-04-21 | 2009-10-28 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type IV inhibitors |
| EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| TW201517906A (zh) * | 2013-07-25 | 2015-05-16 | Almirall Sa | 含有ｍａｂａ化合物和皮質類固醇之組合 |
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| CA3142351A1 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
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| NL124473C (cg-RX-API-DMAC7.html) | 1960-07-26 | |||
| GB1047518A (en) | 1963-06-11 | 1966-11-02 | Glaxo Lab Ltd | 17ª-monoesters of 11,17,21-trihydroxy steroid compounds |
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-
2006
- 2006-10-19 AU AU2006305619A patent/AU2006305619A1/en not_active Abandoned
- 2006-10-19 RU RU2008119323/15A patent/RU2008119323A/ru not_active Application Discontinuation
- 2006-10-19 WO PCT/IB2006/002930 patent/WO2007045979A1/en not_active Ceased
- 2006-10-19 US US12/090,805 patent/US20090221664A1/en not_active Abandoned
- 2006-10-19 EP EP06809068A patent/EP1948164A1/en not_active Withdrawn
- 2006-10-19 BR BRPI0617674-7A patent/BRPI0617674A2/pt not_active IP Right Cessation
- 2006-10-19 JP JP2008536146A patent/JP2009512676A/ja not_active Withdrawn
- 2006-10-19 CA CA002626612A patent/CA2626612A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009512676A (ja) | 2009-03-26 |
| AU2006305619A1 (en) | 2007-04-26 |
| US20090221664A1 (en) | 2009-09-03 |
| EP1948164A1 (en) | 2008-07-30 |
| CA2626612A1 (en) | 2007-04-26 |
| BRPI0617674A2 (pt) | 2011-08-02 |
| WO2007045979A1 (en) | 2007-04-26 |
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Legal Events
| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20110111 |