AU2007336538B2 - Substituted acetophenones useful as PDE4 inhibitors - Google Patents
Substituted acetophenones useful as PDE4 inhibitors Download PDFInfo
- Publication number
- AU2007336538B2 AU2007336538B2 AU2007336538A AU2007336538A AU2007336538B2 AU 2007336538 B2 AU2007336538 B2 AU 2007336538B2 AU 2007336538 A AU2007336538 A AU 2007336538A AU 2007336538 A AU2007336538 A AU 2007336538A AU 2007336538 B2 AU2007336538 B2 AU 2007336538B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- pyridin
- dichloro
- dimethoxy
- 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.)
- Ceased
Links
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 10
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 10
- 150000008062 acetophenones Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 685
- -1 alkylalkoxycarbonyl Chemical group 0.000 claims abstract description 151
- 238000000034 method Methods 0.000 claims abstract description 112
- 239000001257 hydrogen Substances 0.000 claims abstract description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 78
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 68
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 47
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 38
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 37
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 35
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 33
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 31
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
- 150000002367 halogens Chemical group 0.000 claims abstract description 26
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 19
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 18
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 18
- 230000002500 effect on skin Effects 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims abstract description 15
- 239000012453 solvate Substances 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 8
- 150000004677 hydrates Chemical class 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
- 238000002560 therapeutic procedure Methods 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 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 44
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 28
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
- 125000004043 oxo group Chemical group O=* 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 201000004624 Dermatitis Diseases 0.000 claims description 12
- 206010040799 Skin atrophy Diseases 0.000 claims description 12
- 230000032683 aging Effects 0.000 claims description 12
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-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 10
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 10
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 10
- 201000008937 atopic dermatitis Diseases 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 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 compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims description 10
- 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
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 230000002757 inflammatory effect Effects 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
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 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
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 125000003944 tolyl group Chemical group 0.000 claims description 7
- 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 6
- BHSKOINIMXXGFJ-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]acetic acid Chemical compound OC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl BHSKOINIMXXGFJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 6
- 201000004384 Alopecia Diseases 0.000 claims description 6
- 206010012442 Dermatitis contact Diseases 0.000 claims description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 6
- 208000003251 Pruritus Diseases 0.000 claims description 6
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 6
- 208000024780 Urticaria Diseases 0.000 claims description 6
- 206010052428 Wound Diseases 0.000 claims description 6
- 208000027418 Wounds and injury Diseases 0.000 claims description 6
- 206010000496 acne Diseases 0.000 claims description 6
- 231100000360 alopecia Toxicity 0.000 claims description 6
- 208000010668 atopic eczema 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 208000010247 contact dermatitis Diseases 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 230000002062 proliferating effect Effects 0.000 claims description 6
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 6
- 208000017520 skin disease Diseases 0.000 claims description 6
- 150000003431 steroids Chemical class 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
- 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
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 230000001684 chronic effect Effects 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
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 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
- 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
- PDOHITFVBCRDID-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[4-ethoxy-3-methoxy-2-(2-phenylethoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCOC1=C(OC)C(OCC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl PDOHITFVBCRDID-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
- 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
- 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
- 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 239000002253 acid 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
- 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 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 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
- GMRZCWUZXHCTOJ-UHFFFAOYSA-N 1-(2-but-3-enoxy-3,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=CCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl GMRZCWUZXHCTOJ-UHFFFAOYSA-N 0.000 claims description 3
- NFUFDHIMMGDBHD-UHFFFAOYSA-N 1-(3-but-2-ynoxy-2,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound COC1=C(OCC#CC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl NFUFDHIMMGDBHD-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
- 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
- AUDYFIBIJYSVQY-UHFFFAOYSA-N 1-[2-[(5-chlorothiophen-2-yl)methoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=C(Cl)SC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl AUDYFIBIJYSVQY-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
- 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
- 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
- UUYBYQPDBPQDRD-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2-hexoxy-3,4-dimethoxyphenyl)ethanone Chemical compound C1=CC(OC)=C(OC)C(OCCCCCC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl UUYBYQPDBPQDRD-UHFFFAOYSA-N 0.000 claims description 3
- MZVCROAJYCFFBU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxy-2-pent-4-enoxyphenyl)ethanone Chemical compound C=CCCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl MZVCROAJYCFFBU-UHFFFAOYSA-N 0.000 claims description 3
- KHMSWQIKMLFUAB-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxy-2-pentoxyphenyl)ethanone Chemical compound C1=CC(OC)=C(OC)C(OCCCCC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl KHMSWQIKMLFUAB-UHFFFAOYSA-N 0.000 claims description 3
- BFSZKUJJMOONNH-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3-hydroxy-2,4-dimethoxyphenyl)ethanone Chemical compound COC1=C(O)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl BFSZKUJJMOONNH-UHFFFAOYSA-N 0.000 claims description 3
- JJPBTJGCARKTTP-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2,4-dimethoxy-3-(2-methoxyethoxy)phenyl]ethanone Chemical compound COCCOC1=C(OC)C=CC(C(=O)CC=2C(=CN=CC=2Cl)Cl)=C1OC JJPBTJGCARKTTP-UHFFFAOYSA-N 0.000 claims description 3
- DVEVGBSUTXMHHE-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-(2-ethylbutoxy)-3,4-dimethoxyphenyl]ethanone Chemical compound C1=CC(OC)=C(OC)C(OCC(CC)CC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl DVEVGBSUTXMHHE-UHFFFAOYSA-N 0.000 claims description 3
- VPTJUCWNNSOTPJ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-(2-hydroxyethoxy)-3,4-dimethoxyphenyl]ethanone Chemical compound OCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VPTJUCWNNSOTPJ-UHFFFAOYSA-N 0.000 claims description 3
- LIADZBYPVJGPAC-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[(4-fluorophenyl)methoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl LIADZBYPVJGPAC-UHFFFAOYSA-N 0.000 claims description 3
- QGZHZKISGDRSGJ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-methoxyethoxy)phenyl]ethanone Chemical compound C1=CC(OC)=C(OC)C(OCCOC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl QGZHZKISGDRSGJ-UHFFFAOYSA-N 0.000 claims description 3
- VCZXNLUGQYGLGR-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(5-methylhexoxy)phenyl]ethanone Chemical compound CC(C)CCCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VCZXNLUGQYGLGR-UHFFFAOYSA-N 0.000 claims description 3
- IOBPYOLVXMNYCA-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(naphthalen-2-ylmethoxy)phenyl]ethanone Chemical compound C=1C=C2C=CC=CC2=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl IOBPYOLVXMNYCA-UHFFFAOYSA-N 0.000 claims description 3
- SKCAOGYWGHQINO-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(2-methylphenyl)methoxy]phenyl]ethanone Chemical compound C=1C=CC=C(C)C=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl SKCAOGYWGHQINO-UHFFFAOYSA-N 0.000 claims description 3
- CJOMHHRTMYLZAU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(2-methylquinolin-6-yl)methoxy]phenyl]ethanone Chemical compound C=1C=C2N=C(C)C=CC2=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl CJOMHHRTMYLZAU-UHFFFAOYSA-N 0.000 claims description 3
- XLCLLFRIVQWTLX-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(4-methoxyphenyl)-2-oxoethoxy]phenyl]ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)COC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC XLCLLFRIVQWTLX-UHFFFAOYSA-N 0.000 claims description 3
- QTMAZYGAVHCKKX-UHFFFAOYSA-N 2-[(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]propane-1,3-diol Chemical compound NC1=NC=NC2=C1C(Br)=CN2COC(CO)CO QTMAZYGAVHCKKX-UHFFFAOYSA-N 0.000 claims description 3
- GOVSWHMHBSRKRD-UHFFFAOYSA-N 2-[2,3-dimethoxy-6-(2-quinolin-4-ylacetyl)phenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=CC=NC2=CC=CC=C12 GOVSWHMHBSRKRD-UHFFFAOYSA-N 0.000 claims description 3
- BVBZISHRASEXBD-UHFFFAOYSA-N 2-[2,3-dimethoxy-6-[2-(2-methoxypyridin-4-yl)acetyl]phenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=CC=NC(OC)=C1 BVBZISHRASEXBD-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
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- DKXYEGNIOKXIKZ-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-phenoxyethyl)acetamide Chemical compound C=1C=CC=CC=1OCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DKXYEGNIOKXIKZ-UHFFFAOYSA-N 0.000 claims description 3
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- GKXQOALDXIWVFF-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(3-hydroxypropyl)acetamide Chemical compound OCCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl GKXQOALDXIWVFF-UHFFFAOYSA-N 0.000 claims description 3
- LFUPPELHGPIHFO-CILPGNKCSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]acetamide Chemical compound C([C@H]1O)C2=CC=CC=C2C1NC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl LFUPPELHGPIHFO-CILPGNKCSA-N 0.000 claims description 3
- NTKPBNIVYQNNMP-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(3-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC(CNC(=O)COC=2C(=C(OC)C=CC=2C(=O)CC=2C(=CN=CC=2Cl)Cl)OC)=C1 NTKPBNIVYQNNMP-UHFFFAOYSA-N 0.000 claims description 3
- ULRSLYOKYFRMBD-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-ethylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl ULRSLYOKYFRMBD-UHFFFAOYSA-N 0.000 claims description 3
- PWJAONOQKNOFHN-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-methylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl PWJAONOQKNOFHN-UHFFFAOYSA-N 0.000 claims description 3
- HOMXWYBOLCQCME-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-phenylacetamide Chemical compound C=1C=CC=CC=1NC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl HOMXWYBOLCQCME-UHFFFAOYSA-N 0.000 claims description 3
- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims description 3
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- SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 claims description 3
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims description 3
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- GVCLNACSYKYUHP-UHFFFAOYSA-N 4-amino-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine-5-carbothioamide Chemical compound C1=NC(N)=C2C(C(=S)N)=CN(COCCO)C2=N1 GVCLNACSYKYUHP-UHFFFAOYSA-N 0.000 claims description 3
- GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims description 3
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 claims description 3
- NJIAKNWTIVDSDA-FQEVSTJZSA-N 7-[4-(1-methylsulfonylpiperidin-4-yl)phenyl]-n-[[(2s)-morpholin-2-yl]methyl]pyrido[3,4-b]pyrazin-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=CC=C(C=2N=C(NC[C@H]3OCCNC3)C3=NC=CN=C3C=2)C=C1 NJIAKNWTIVDSDA-FQEVSTJZSA-N 0.000 claims description 3
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims description 3
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 claims description 3
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 claims description 3
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 claims description 3
- SCJNYBYSTCRPAO-LXBQGUBHSA-N CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 Chemical compound CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 SCJNYBYSTCRPAO-LXBQGUBHSA-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
- 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
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 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
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 3
- ATHHOZFTRSFWRA-UHFFFAOYSA-N n-(cycloheptylmethyl)-2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]acetamide Chemical compound C1CCCCCC1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl ATHHOZFTRSFWRA-UHFFFAOYSA-N 0.000 claims description 3
- KPPYPCAZNJRQEY-UHFFFAOYSA-N n-(cyclohexylmethyl)-2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]acetamide Chemical compound C1CCCCC1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl KPPYPCAZNJRQEY-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- TUCLWFKMQCCWOY-UHFFFAOYSA-N n-cyclopentyl-2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]acetamide Chemical compound C1CCCC1NC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl TUCLWFKMQCCWOY-UHFFFAOYSA-N 0.000 claims description 3
- PDUSWJORWQPNRP-UHFFFAOYSA-N n-propan-2-ylacetamide Chemical compound CC(C)NC(C)=O PDUSWJORWQPNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl 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
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 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
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- 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
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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
- A61P17/08—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
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- 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
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- 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
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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
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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
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Toxicology (AREA)
- Oncology (AREA)
- Pain & Pain Management (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)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2012203892A AU2012203892A1 (en) | 2006-12-22 | 2012-07-03 | Substituted acetophenones useful as PDE4 inhibitors |
Applications Claiming Priority (5)
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| 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2012203892A Division AU2012203892A1 (en) | 2006-12-22 | 2012-07-03 | Substituted acetophenones useful as PDE4 inhibitors |
Publications (2)
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| AU2007336538A1 AU2007336538A1 (en) | 2008-07-03 |
| AU2007336538B2 true AU2007336538B2 (en) | 2012-04-05 |
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| AU2007336538A Ceased AU2007336538B2 (en) | 2006-12-22 | 2007-12-21 | Substituted acetophenones useful as PDE4 inhibitors |
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| US (3) | US8148537B2 (https=) |
| EP (1) | EP2125736B1 (https=) |
| JP (1) | JP5342451B2 (https=) |
| KR (1) | KR101507717B1 (https=) |
| AT (1) | ATE503742T1 (https=) |
| AU (1) | AU2007336538B2 (https=) |
| BR (1) | BRPI0721113A2 (https=) |
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| CY (1) | CY1111596T1 (https=) |
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| PT (1) | PT2125736E (https=) |
| RU (1) | RU2493149C2 (https=) |
| WO (1) | WO2008077404A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ601001A (en) | 2009-12-22 | 2014-07-25 | Leo Pharma As | Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue |
| BR112012015433B8 (pt) | 2009-12-22 | 2020-03-03 | Leo Pharma As | composição farmacêutica substancialmente anidra para aplicação cutânea |
| MX2012007234A (es) | 2009-12-22 | 2012-07-30 | Leo Pharma As | Nanocristales de monohidrato de calciprotiol. |
| 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 |
| SI3060551T1 (sl) * | 2013-10-22 | 2019-11-29 | Chiesi Farm Spa | Postopek za pripravo inhibitorja PDE4 |
| MX2016016378A (es) * | 2014-06-23 | 2017-10-16 | Leo Pharma As | Metodos para la preparacion de compuestos heterociclicos de 1,3-benzodioxol. |
| 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 |
| DK3390407T3 (da) | 2015-12-18 | 2023-11-06 | Union Therapeutics As | Fremgangsmåder til fremstilling af heterocykliske 1,3-benzodioxolforbindelser |
| KR101702648B1 (ko) * | 2016-05-10 | 2017-02-03 | 주식회사 엑티브온 | 피부 외용제용 보존제, 이를 포함하는 화장료 조성물 및 약학 조성물 |
| DK3642210T3 (da) | 2017-06-20 | 2024-12-09 | Union Therapeutics As | Fremgangsmåder til fremstilling af heterocykliske 1,3-benzodioxolforbindelser |
| 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 |
Citations (1)
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| EP0943613A1 (en) * | 1996-11-19 | 1999-09-22 | Kyowa Hakko Kogyo Kabushiki Kaisha | Oxygenic heterocyclic compounds |
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| TW263495B (https=) * | 1992-12-23 | 1995-11-21 | Celltech Ltd | |
| GB9401460D0 (en) * | 1994-01-26 | 1994-03-23 | Rhone Poulenc Rorer Ltd | Compositions of matter |
| ATE325110T1 (de) * | 1995-05-19 | 2006-06-15 | Kyowa Hakko Kogyo Kk | Sauerstoff enthaltende heterocyclische verbindungen |
| US6514996B2 (en) * | 1995-05-19 | 2003-02-04 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of benzofuran or benzodioxole |
| MXPA05009921A (es) * | 2003-03-17 | 2005-11-04 | Kyowa Hakko Kogyo Kk | Agentes terapeuticos y/o preventivos para enfermedades cutaneas cronicas. |
| 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 |
| WO2006135828A2 (en) * | 2005-06-10 | 2006-12-21 | Memory Pharmaceuticals Corporation | Trisubstituted amines as phosphodiesterase 4 inhibitors |
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2007
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- 2007-12-21 DE DE602007013617T patent/DE602007013617D1/de active Active
- 2007-12-21 US US12/520,325 patent/US8148537B2/en not_active Expired - Fee Related
- 2007-12-21 NZ NZ577863A patent/NZ577863A/en not_active IP Right Cessation
- 2007-12-21 RU RU2009128191/04A patent/RU2493149C2/ru not_active IP Right Cessation
- 2007-12-21 BR BRPI0721113-9A2A patent/BRPI0721113A2/pt not_active Application Discontinuation
- 2007-12-21 AT AT07846434T patent/ATE503742T1/de active
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- 2007-12-21 HR HR20110464T patent/HRP20110464T1/hr unknown
- 2007-12-21 MX MX2009006593A patent/MX2009006593A/es active IP Right Grant
- 2007-12-21 MY MYPI20092592A patent/MY146022A/en unknown
- 2007-12-21 JP JP2009541766A patent/JP5342451B2/ja not_active Expired - Fee Related
- 2007-12-21 PL PL07846434T patent/PL2125736T3/pl unknown
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2009
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2011
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- 2012-07-11 US US13/546,758 patent/US8497380B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0943613A1 (en) * | 1996-11-19 | 1999-09-22 | Kyowa Hakko Kogyo Kabushiki Kaisha | Oxygenic heterocyclic compounds |
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