CA2673370C - Substituted acetophenones useful as pde4 inhibitors - Google Patents
Substituted acetophenones useful as pde4 inhibitors Download PDFInfo
- Publication number
- CA2673370C CA2673370C CA2673370A CA2673370A CA2673370C CA 2673370 C CA2673370 C CA 2673370C CA 2673370 A CA2673370 A CA 2673370A CA 2673370 A CA2673370 A CA 2673370A CA 2673370 C CA2673370 C CA 2673370C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- pyridin
- dimethoxy
- dichloro
- 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.)
- Expired - Fee Related
Links
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 9
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 9
- 150000008062 acetophenones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 695
- -1 alkylalkoxycarbonyl Chemical group 0.000 claims abstract description 151
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 77
- 239000001257 hydrogen Substances 0.000 claims abstract description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 70
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 49
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 46
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 45
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 42
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 40
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 37
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
- 150000002367 halogens Chemical group 0.000 claims abstract description 34
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 23
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 23
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000002500 effect on skin Effects 0.000 claims abstract description 15
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 150000004677 hydrates Chemical class 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000004043 oxo group Chemical group O=* 0.000 claims description 35
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical group CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 15
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 201000004624 Dermatitis Diseases 0.000 claims description 10
- 206010040799 Skin atrophy Diseases 0.000 claims description 10
- 230000032683 aging Effects 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical group CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims description 10
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 9
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 9
- 201000008937 atopic dermatitis Diseases 0.000 claims description 9
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 9
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 8
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- 125000003944 tolyl group Chemical group 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 206010052428 Wound Diseases 0.000 claims description 6
- 208000027418 Wounds and injury Diseases 0.000 claims description 6
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 6
- KNLPKARZJDKEAM-UHFFFAOYSA-N 2-(2,3-dimethoxy-6-methoxycarbonylphenoxy)acetic acid Chemical compound COC(=O)C1=CC=C(OC)C(OC)=C1OCC(O)=O KNLPKARZJDKEAM-UHFFFAOYSA-N 0.000 claims description 5
- IRKBYACLGSSVDO-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2-hydroxy-3,4-dimethoxyphenyl)ethanone Chemical compound OC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl IRKBYACLGSSVDO-UHFFFAOYSA-N 0.000 claims description 5
- SDZOJIYKTNKVMO-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3-ethoxy-2-hydroxy-4-methoxyphenyl)ethanone Chemical compound C1=C(OC)C(OCC)=C(O)C(C(=O)CC=2C(=CN=CC=2Cl)Cl)=C1 SDZOJIYKTNKVMO-UHFFFAOYSA-N 0.000 claims description 5
- DYUBQXVOBFCBPQ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-phenylethoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DYUBQXVOBFCBPQ-UHFFFAOYSA-N 0.000 claims description 5
- MXWZBLXSYIHAKD-UHFFFAOYSA-N 2-[2-(tert-butylamino)-3,5-dichloropyridin-4-yl]-1-[2-[2-(4-fluorophenyl)ethoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC(NC(C)(C)C)=C1Cl MXWZBLXSYIHAKD-UHFFFAOYSA-N 0.000 claims description 5
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 5
- 201000004384 Alopecia Diseases 0.000 claims description 5
- 206010012442 Dermatitis contact Diseases 0.000 claims description 5
- 208000003251 Pruritus Diseases 0.000 claims description 5
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 5
- 208000024780 Urticaria Diseases 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- 206010000496 acne Diseases 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 231100000360 alopecia Toxicity 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 208000010247 contact dermatitis Diseases 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
- ZTVJGLNERKGVDH-UHFFFAOYSA-N methyl 3,4-dimethoxy-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]benzoate Chemical compound COC(=O)C1=CC=C(OC)C(OC)=C1OCC(=O)OC(C)(C)C ZTVJGLNERKGVDH-UHFFFAOYSA-N 0.000 claims description 5
- LYNHJUCTFFHRPC-UHFFFAOYSA-N methyl 3,4-dimethoxy-2-[2-oxo-2-(propylamino)ethoxy]benzoate Chemical compound CCCNC(=O)COC1=C(C(=O)OC)C=CC(OC)=C1OC LYNHJUCTFFHRPC-UHFFFAOYSA-N 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 230000002062 proliferating effect Effects 0.000 claims description 5
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 5
- 208000017520 skin disease Diseases 0.000 claims description 5
- 150000003431 steroids Chemical class 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- SKUOFNDSDASKRV-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2,3-diethoxy-4-methoxyphenyl)ethanone Chemical compound CCOC1=C(OC)C=CC(C(=O)CC=2C(=CN=CC=2Cl)Cl)=C1OCC SKUOFNDSDASKRV-UHFFFAOYSA-N 0.000 claims description 4
- BOVSNWBYIPDQLD-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[2-(4-fluorophenyl)ethoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl BOVSNWBYIPDQLD-UHFFFAOYSA-N 0.000 claims description 4
- XMAYLTKCWBYEPQ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[4-methoxy-2,3-bis(prop-2-enoxy)phenyl]ethanone Chemical compound C=CCOC1=C(OCC=C)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl XMAYLTKCWBYEPQ-UHFFFAOYSA-N 0.000 claims description 4
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 claims description 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 4
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 claims description 4
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 claims description 4
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 claims description 4
- IHPHPGLJYCDONF-UHFFFAOYSA-N Essigsaeure-propylamid Natural products CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 4
- PAVMRYVMZLANOQ-UHFFFAOYSA-N N-(1-phenylethyl)acetamide Chemical compound CC(=O)NC(C)C1=CC=CC=C1 PAVMRYVMZLANOQ-UHFFFAOYSA-N 0.000 claims description 4
- MODKMHXGCGKTLE-UHFFFAOYSA-N N-acetylphenylethylamine Chemical compound CC(=O)NCCC1=CC=CC=C1 MODKMHXGCGKTLE-UHFFFAOYSA-N 0.000 claims description 4
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 claims description 4
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000005425 toluyl group Chemical group 0.000 claims description 4
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims description 3
- JMSLXMMWELRQMU-UHFFFAOYSA-N 1-(2-but-2-ynoxy-3,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound CC#CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl JMSLXMMWELRQMU-UHFFFAOYSA-N 0.000 claims description 3
- VSYDBUNFIWMARN-UHFFFAOYSA-N 1-[2,3-bis(difluoromethoxy)-4-methoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound FC(F)OC1=C(OC(F)F)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VSYDBUNFIWMARN-UHFFFAOYSA-N 0.000 claims description 3
- KNORRWPIABKHRZ-UHFFFAOYSA-N 1-[2-(1,3-benzoxazol-2-ylmethoxy)-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound N=1C2=CC=CC=C2OC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl KNORRWPIABKHRZ-UHFFFAOYSA-N 0.000 claims description 3
- DTYNTAQEFRZTOF-UHFFFAOYSA-N 1-[2-(2-cyclohexylethoxy)-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C1CCCCC1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DTYNTAQEFRZTOF-UHFFFAOYSA-N 0.000 claims description 3
- JPPSVGGLBXSRPM-UHFFFAOYSA-N 1-[2-(cyclohexylmethoxy)-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C1CCCCC1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl JPPSVGGLBXSRPM-UHFFFAOYSA-N 0.000 claims description 3
- UUALYBMSYGWDOD-UHFFFAOYSA-N 1-[2-[(3-chlorophenyl)methoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=CC(Cl)=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl UUALYBMSYGWDOD-UHFFFAOYSA-N 0.000 claims description 3
- QMAFRTURZBLNNV-UHFFFAOYSA-N 1-[2-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound N=1N=C(C2CC2)SC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl QMAFRTURZBLNNV-UHFFFAOYSA-N 0.000 claims description 3
- DOQIRWPNZIGHBL-UHFFFAOYSA-N 1-[2-[2-(3-bromophenyl)ethoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=CC(Br)=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DOQIRWPNZIGHBL-UHFFFAOYSA-N 0.000 claims description 3
- FIWOJRHNMZWIII-UHFFFAOYSA-N 1-[2-[2-(4-chlorophenyl)ethoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=C(Cl)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl FIWOJRHNMZWIII-UHFFFAOYSA-N 0.000 claims description 3
- XGNROMYEANDWBV-UHFFFAOYSA-N 1-[3-(cyclopropylmethoxy)-2,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound COC1=C(OCC2CC2)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl XGNROMYEANDWBV-UHFFFAOYSA-N 0.000 claims description 3
- QCFYWMAMQISZND-UHFFFAOYSA-N 2-(2-amino-3,5-dichloropyridin-4-yl)-1-[2-[2-(4-fluorophenyl)ethoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC(N)=C1Cl QCFYWMAMQISZND-UHFFFAOYSA-N 0.000 claims description 3
- ASJWCPHMNSBYKS-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2,4-dimethoxy-3-phenylmethoxyphenyl)ethanone Chemical compound COC1=C(OCC=2C=CC=CC=2)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl ASJWCPHMNSBYKS-UHFFFAOYSA-N 0.000 claims description 3
- NBXASMDRACSYCU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2,4-dimethoxy-3-prop-2-ynoxyphenyl)ethanone Chemical compound COC1=C(OCC#C)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl NBXASMDRACSYCU-UHFFFAOYSA-N 0.000 claims description 3
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- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 claims description 3
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 claims description 3
- DRBWRJPFNOBNIO-KOLCDFICSA-N [(2r)-1-[(2r)-2-(pyridine-4-carbonylamino)propanoyl]pyrrolidin-2-yl]boronic acid Chemical compound N([C@H](C)C(=O)N1[C@@H](CCC1)B(O)O)C(=O)C1=CC=NC=C1 DRBWRJPFNOBNIO-KOLCDFICSA-N 0.000 claims description 3
- YGPZYYDTPXVBRA-RTDBHSBRSA-N [(2r,3s,4r,5r,6s)-2-[[(2r,3r,4r,5s,6r)-3-[[(3r)-3-dodecanoyloxytetradecanoyl]amino]-6-(hydroxymethyl)-5-phosphonooxy-4-[(3r)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]oxymethyl]-3,6-dihydroxy-5-[[(3r)-3-hydroxytetradecanoyl]amino]oxan-4-yl] (3r)-3-hydr Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](O)O1 YGPZYYDTPXVBRA-RTDBHSBRSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims description 3
- OTKPPUXRIADSGD-PPRNARJGSA-N avoparcina Chemical compound O([C@@H]1C2=CC=C(C(=C2)Cl)OC=2C=C3C=C(C=2O[C@H]2C([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@H](N)C2)OC2=CC=C(C=C2)[C@@H](O)[C@H](C(N[C@H](C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)C=1C=CC(O)=CC=1)=O)NC(=O)[C@H](NC)C=1C=CC(O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)=CC=1)[C@H]1C[C@@H](N)[C@@H](O)[C@H](C)O1 OTKPPUXRIADSGD-PPRNARJGSA-N 0.000 claims description 3
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- UOQJISLMCFWFNY-UHFFFAOYSA-N benzyl 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]acetate Chemical compound C=1C=CC=CC=1COC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl UOQJISLMCFWFNY-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- LENLZXDUFDBDQZ-UHFFFAOYSA-N methyl 3-[[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C(=C(OC)C=CC=2C(=O)CC=2C(=CN=CC=2Cl)Cl)OC)=C1 LENLZXDUFDBDQZ-UHFFFAOYSA-N 0.000 claims description 3
- DOMKXMBAWZRPQL-UHFFFAOYSA-N methyl 4-[[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1COC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC DOMKXMBAWZRPQL-UHFFFAOYSA-N 0.000 claims description 3
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- IHCHOVVAJBADAH-UHFFFAOYSA-N n-[2-hydroxy-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1C2=CC(OC)=CC=C2OCC1C(=O)NC(C(=C1)O)=CC=C1C=1C=NNC=1 IHCHOVVAJBADAH-UHFFFAOYSA-N 0.000 claims description 3
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 claims description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
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- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims description 3
- AUXSMGHTDXFMAO-UHFFFAOYSA-N tert-butyl 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-3-methoxy-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenoxy]acetate Chemical compound CC(C)(C)OC(=O)COC1=C(OCC(=O)OC(C)(C)C)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl AUXSMGHTDXFMAO-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
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- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical class CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229950006828 timegadine Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 108700026220 vif Genes Proteins 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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]
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Toxicology (AREA)
- Epidemiology (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87168906P | 2006-12-22 | 2006-12-22 | |
| US60/871,689 | 2006-12-22 | ||
| US94547007P | 2007-06-21 | 2007-06-21 | |
| US60/945,470 | 2007-06-21 | ||
| PCT/DK2007/000564 WO2008077404A1 (en) | 2006-12-22 | 2007-12-21 | Substituted acetophenones useful as pde4 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2673370A1 CA2673370A1 (en) | 2008-07-03 |
| CA2673370C true CA2673370C (en) | 2015-11-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2673370A Expired - Fee Related CA2673370C (en) | 2006-12-22 | 2007-12-21 | Substituted acetophenones useful as pde4 inhibitors |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US8148537B2 (enExample) |
| EP (1) | EP2125736B1 (enExample) |
| JP (1) | JP5342451B2 (enExample) |
| KR (1) | KR101507717B1 (enExample) |
| AT (1) | ATE503742T1 (enExample) |
| AU (1) | AU2007336538B2 (enExample) |
| BR (1) | BRPI0721113A2 (enExample) |
| CA (1) | CA2673370C (enExample) |
| CR (1) | CR10877A (enExample) |
| CY (1) | CY1111596T1 (enExample) |
| DE (1) | DE602007013617D1 (enExample) |
| DK (1) | DK2125736T3 (enExample) |
| GT (1) | GT200900172A (enExample) |
| HR (1) | HRP20110464T1 (enExample) |
| IL (1) | IL199383A (enExample) |
| MX (1) | MX2009006593A (enExample) |
| MY (1) | MY146022A (enExample) |
| NO (1) | NO20092372L (enExample) |
| NZ (1) | NZ577863A (enExample) |
| PL (1) | PL2125736T3 (enExample) |
| PT (1) | PT2125736E (enExample) |
| RU (1) | RU2493149C2 (enExample) |
| WO (1) | WO2008077404A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2785253A1 (en) | 2009-12-22 | 2011-06-30 | Leo Pharma A/S | Calcipotriol monohydrate nanocrystals |
| EP2515866B1 (en) | 2009-12-22 | 2014-02-19 | Leo Pharma A/S | Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue |
| JP5873439B2 (ja) | 2009-12-22 | 2016-03-01 | レオ ファーマ アクティーゼルスカブ | ビタミンｄ類似体および溶媒と界面活性剤の混合物を含む皮膚組成物 |
| CN102775345A (zh) * | 2011-05-13 | 2012-11-14 | 上海特化医药科技有限公司 | 制备罗氟司特的方法及中间体 |
| EP2925364A1 (en) * | 2012-11-30 | 2015-10-07 | Leo Pharma A/S | A method of inhibiting the expression of il-22 in activated t-cells |
| WO2014096018A1 (en) * | 2012-12-19 | 2014-06-26 | Leo Pharma A/S | Methods for the preparation of substituted acetophenones |
| SI3587400T1 (sl) | 2013-10-22 | 2024-05-31 | Chiesi Farmaceutici S.P.A. | Postopek za pripravo zaviralca pde4 |
| CN106459081B (zh) | 2014-06-23 | 2019-09-10 | 利奥制药有限公司 | 1,3-苯并二氧杂环戊烯杂环化合物的制备方法 |
| WO2017089347A1 (en) | 2015-11-25 | 2017-06-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas |
| MX385592B (es) | 2015-12-18 | 2025-03-18 | Union Therapeutics As | Metodos para preparacion de compuestos heterociclicos de 1,3-benzodioxol. |
| KR101702648B1 (ko) * | 2016-05-10 | 2017-02-03 | 주식회사 엑티브온 | 피부 외용제용 보존제, 이를 포함하는 화장료 조성물 및 약학 조성물 |
| CN118344381A (zh) | 2017-06-20 | 2024-07-16 | 联合疗法公司 | 用于制备1,3-苯并二氧杂环戊烯杂环化合物的方法 |
| EP3838967A1 (en) | 2019-12-16 | 2021-06-23 | Spago Nanomedical AB | Immobilization of phenolic compounds |
| CN117924243B (zh) * | 2024-01-16 | 2025-09-12 | 沈阳药科大学 | 一种喹啉衍生物及其药用组合物和应用 |
Family Cites Families (8)
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| TW263495B (enExample) * | 1992-12-23 | 1995-11-21 | Celltech Ltd | |
| GB9401460D0 (en) * | 1994-01-26 | 1994-03-23 | Rhone Poulenc Rorer Ltd | Compositions of matter |
| JP4172817B2 (ja) * | 1995-05-19 | 2008-10-29 | 協和醗酵工業株式会社 | 含酸素複素環化合物 |
| US6514996B2 (en) * | 1995-05-19 | 2003-02-04 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of benzofuran or benzodioxole |
| WO1998022455A1 (en) * | 1996-11-19 | 1998-05-28 | Kyowa Hakko Kogyo Co., Ltd. | Oxygenic heterocyclic compounds |
| HRP20050905A2 (hr) * | 2003-03-17 | 2006-04-30 | Kyowa Hakko Kogyo Co. | Terapeutski i/ili preventivni agensi za kronične kožne bolesti |
| WO2006040645A1 (en) * | 2004-10-11 | 2006-04-20 | Ranbaxy Laboratories Limited | N-(3,5-dichloropyridin-4-yl)-2,4,5-alkoxy and 2,3,4-alkoxy benzamide derivatives as pde-iv (phophodiesterase type-iv) inhibitors for the treatment of inflammatory diseases such as asthma |
| EP1888528A2 (en) * | 2005-06-10 | 2008-02-20 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
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2007
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- 2007-12-21 CA CA2673370A patent/CA2673370C/en not_active Expired - Fee Related
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- 2007-12-21 RU RU2009128191/04A patent/RU2493149C2/ru not_active IP Right Cessation
- 2007-12-21 HR HR20110464T patent/HRP20110464T1/hr unknown
- 2007-12-21 NZ NZ577863A patent/NZ577863A/en not_active IP Right Cessation
- 2007-12-21 PL PL07846434T patent/PL2125736T3/pl unknown
- 2007-12-21 AT AT07846434T patent/ATE503742T1/de active
- 2007-12-21 PT PT07846434T patent/PT2125736E/pt unknown
- 2007-12-21 KR KR1020097015481A patent/KR101507717B1/ko not_active Expired - Fee Related
- 2007-12-21 JP JP2009541766A patent/JP5342451B2/ja not_active Expired - Fee Related
- 2007-12-21 MX MX2009006593A patent/MX2009006593A/es active IP Right Grant
- 2007-12-21 WO PCT/DK2007/000564 patent/WO2008077404A1/en not_active Ceased
- 2007-12-21 EP EP07846434A patent/EP2125736B1/en active Active
- 2007-12-21 US US12/520,325 patent/US8148537B2/en not_active Expired - Fee Related
- 2007-12-21 AU AU2007336538A patent/AU2007336538B2/en not_active Ceased
- 2007-12-21 MY MYPI20092592A patent/MY146022A/en unknown
- 2007-12-21 DK DK07846434.4T patent/DK2125736T3/da active
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2009
- 2009-06-16 IL IL199383A patent/IL199383A/en active IP Right Grant
- 2009-06-19 CR CR10877A patent/CR10877A/es unknown
- 2009-06-19 GT GT200900172A patent/GT200900172A/es unknown
- 2009-06-22 NO NO20092372A patent/NO20092372L/no not_active Application Discontinuation
-
2011
- 2011-06-28 CY CY20111100615T patent/CY1111596T1/el unknown
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2012
- 2012-02-28 US US13/406,932 patent/US8324394B2/en not_active Expired - Fee Related
- 2012-07-11 US US13/546,758 patent/US8497380B2/en not_active Expired - Fee Related
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| EEER | Examination request | ||
| EEER | Examination request |
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| MKLA | Lapsed |
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