AU2011253203A1 - Bifunctional quinoline derivatives - Google Patents
Bifunctional quinoline derivatives Download PDFInfo
- Publication number
- AU2011253203A1 AU2011253203A1 AU2011253203A AU2011253203A AU2011253203A1 AU 2011253203 A1 AU2011253203 A1 AU 2011253203A1 AU 2011253203 A AU2011253203 A AU 2011253203A AU 2011253203 A AU2011253203 A AU 2011253203A AU 2011253203 A1 AU2011253203 A1 AU 2011253203A1
- Authority
- AU
- Australia
- Prior art keywords
- amino
- hydroxy
- phenyl
- oxo
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 5
- 230000001588 bifunctional effect Effects 0.000 title description 4
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 570
- 239000000203 mixture Substances 0.000 claims abstract description 179
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 118
- 238000000034 method Methods 0.000 claims abstract description 71
- 206010035664 Pneumonia Diseases 0.000 claims abstract description 37
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 27
- 206010006482 Bronchospasm Diseases 0.000 claims abstract description 13
- 230000007885 bronchoconstriction Effects 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims description 99
- -1 methoxyphenyl Chemical group 0.000 claims description 96
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 89
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 88
- 238000011282 treatment Methods 0.000 claims description 66
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 125000006413 ring segment Chemical group 0.000 claims description 43
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 39
- 125000002947 alkylene group Chemical group 0.000 claims description 39
- 125000004450 alkenylene group Chemical group 0.000 claims description 37
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000004419 alkynylene group Chemical group 0.000 claims description 31
- 206010006451 bronchitis Diseases 0.000 claims description 31
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 27
- 201000009267 bronchiectasis Diseases 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 22
- 208000006673 asthma Diseases 0.000 claims description 20
- 201000009890 sinusitis Diseases 0.000 claims description 20
- 239000013543 active substance Substances 0.000 claims description 19
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
- 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 18
- 206010006448 Bronchiolitis Diseases 0.000 claims description 17
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 14
- 206010014561 Emphysema Diseases 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 208000007451 chronic bronchitis Diseases 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 208000000884 Airway Obstruction Diseases 0.000 claims description 13
- 206010011224 Cough Diseases 0.000 claims description 13
- 206010044314 Tracheobronchitis Diseases 0.000 claims description 13
- 230000002427 irreversible effect Effects 0.000 claims description 13
- 230000002441 reversible effect Effects 0.000 claims description 13
- 208000009470 Ventilator-Associated Pneumonia Diseases 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
- YSIMFLSKCUKIKV-UHFFFAOYSA-N 2-methylquinoline-3-carboxamide Chemical compound C1=CC=C2C=C(C(N)=O)C(C)=NC2=C1 YSIMFLSKCUKIKV-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000003857 carboxamides Chemical class 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000812 cholinergic antagonist Substances 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- BRRAAVRHYYQTFP-UHFFFAOYSA-N 8-methylquinoline-3-carboxamide Chemical compound NC(=O)C1=CN=C2C(C)=CC=CC2=C1 BRRAAVRHYYQTFP-UHFFFAOYSA-N 0.000 claims description 5
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- DEKUILZSWDGHAM-UHFFFAOYSA-N 4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC=CC(C)=C3N=CC=2C(N)=O)=C1 DEKUILZSWDGHAM-UHFFFAOYSA-N 0.000 claims description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 229940125715 antihistaminic agent Drugs 0.000 claims description 4
- 239000000739 antihistaminic agent Substances 0.000 claims description 4
- 229960005475 antiinfective agent Drugs 0.000 claims description 4
- 239000004599 antimicrobial Substances 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 239000002713 epithelial sodium channel blocking agent Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229940043355 kinase inhibitor Drugs 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- HJBZAZITZDSWKD-RWYGWLOXSA-N 6-[3-[[4-[5-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]pent-1-ynyl]phenyl]carbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NC=2C=CC(=CC=2)C#CCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 HJBZAZITZDSWKD-RWYGWLOXSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- LQGFARIRZVIMAL-WBCKFURZSA-N 6-[3-[[4-[6-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]hex-1-ynyl]phenyl]carbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NC=2C=CC(=CC=2)C#CCCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 LQGFARIRZVIMAL-WBCKFURZSA-N 0.000 claims description 2
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 2
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- 239000004305 biphenyl Substances 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- DQLVYPNGWDAROB-BHVANESWSA-N 6-[3-[6-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]hexylcarbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NCCCCCCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 DQLVYPNGWDAROB-BHVANESWSA-N 0.000 claims 1
- ZDFDVHNJXKVUAX-RWYGWLOXSA-N 6-[3-[[3-[5-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]pent-1-ynyl]phenyl]carbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NC=2C=C(C=CC=2)C#CCCCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=C1 ZDFDVHNJXKVUAX-RWYGWLOXSA-N 0.000 claims 1
- UZWQWAVCZAHYNC-RWYGWLOXSA-N 6-[3-[[4-[5-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]pentyl]phenyl]carbamoyl]phenyl]sulfonyl-4-(3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(C=CC=2)C(=O)NC=2C=CC(CCCCCNC[C@H](O)C=3C=C(CO)C(O)=CC=3)=CC=2)=C1 UZWQWAVCZAHYNC-RWYGWLOXSA-N 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- YXNHHCXSSOWLFU-GWHBCOKCSA-N [3-[3-carbamoyl-4-(3-methoxyanilino)-8-methylquinolin-6-yl]sulfonylphenyl]methyl 4-[4-[4-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]butyl]phenyl]piperazine-1-carboxylate Chemical compound COC1=CC=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)C=2C=C(COC(=O)N3CCN(CC3)C=3C=CC(CCCCNC[C@H](O)C=4C=5C=CC(=O)NC=5C(O)=CC=4)=CC=3)C=CC=2)=C1 YXNHHCXSSOWLFU-GWHBCOKCSA-N 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 229940125846 compound 25 Drugs 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 15
- 239000000543 intermediate Substances 0.000 description 563
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
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- 239000000243 solution Substances 0.000 description 93
- 239000000758 substrate Substances 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 76
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- 125000005843 halogen group Chemical group 0.000 description 33
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
- 241000124008 Mammalia Species 0.000 description 30
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- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 27
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- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 27
- 239000011734 sodium Substances 0.000 description 27
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- 238000012360 testing method Methods 0.000 description 24
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- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 description 20
- WDCOJSGXSPGNFK-UHFFFAOYSA-N 8-aminooctan-1-ol Chemical compound NCCCCCCCCO WDCOJSGXSPGNFK-UHFFFAOYSA-N 0.000 description 19
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 235000009518 sodium iodide Nutrition 0.000 description 1
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- MREGGBKMNSBSDX-UHFFFAOYSA-N tert-butyl n-[2-[4-[2-(methylamino)ethoxy]phenyl]ethyl]carbamate Chemical compound CNCCOC1=CC=C(CCNC(=O)OC(C)(C)C)C=C1 MREGGBKMNSBSDX-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-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
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- 125000004927 thianaphthalenyl group Chemical group S1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229960001205 tridihexethyl chloride Drugs 0.000 description 1
- XJGONMZLEDGBRM-UHFFFAOYSA-M tridihexethyl chloride Chemical compound [Cl-].C=1C=CC=CC=1C(O)(CC[N+](CC)(CC)CC)C1CCCCC1 XJGONMZLEDGBRM-UHFFFAOYSA-M 0.000 description 1
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- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
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- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 description 1
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- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33302010P | 2010-05-10 | 2010-05-10 | |
| US61/333,020 | 2010-05-10 | ||
| US40693010P | 2010-10-26 | 2010-10-26 | |
| US61/406,930 | 2010-10-26 | ||
| US201161477263P | 2011-04-20 | 2011-04-20 | |
| US61/477,263 | 2011-04-20 | ||
| PCT/US2011/035738 WO2011143105A1 (en) | 2010-05-10 | 2011-05-09 | Bifunctional quinoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2011253203A1 true AU2011253203A1 (en) | 2012-11-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011253203A Abandoned AU2011253203A1 (en) | 2010-05-10 | 2011-05-09 | Bifunctional quinoline derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8394829B2 (https=) |
| EP (1) | EP2569285A1 (https=) |
| JP (2) | JP5807058B2 (https=) |
| AR (1) | AR081026A1 (https=) |
| AU (1) | AU2011253203A1 (https=) |
| CA (1) | CA2796826A1 (https=) |
| NZ (1) | NZ603136A (https=) |
| UY (1) | UY33372A (https=) |
| WO (1) | WO2011143105A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2569285A1 (en) * | 2010-05-10 | 2013-03-20 | Gilead Sciences, Inc. | Bifunctional quinoline derivatives |
| CN105121439A (zh) | 2013-02-19 | 2015-12-02 | 辉瑞公司 | 作为pde4亚型抑制剂用于治疗cns和其他病症的氮杂苯并咪唑化合物 |
| EP3102569A1 (en) * | 2014-02-06 | 2016-12-14 | AbbVie Inc. | 6-heteroaryloxy- and 6-aryloxy-quinoline-2-carboxamides and uses thereof |
| JP6125467B2 (ja) * | 2014-06-16 | 2017-05-10 | 富士フイルム株式会社 | プリント注文受付機とその作動方法および作動プログラム |
| WO2016012896A1 (en) | 2014-07-24 | 2016-01-28 | Pfizer Inc. | Pyrazolopyrimidine compounds |
| PL3177624T3 (pl) | 2014-08-06 | 2019-09-30 | Pfizer Inc. | Związki imidazopirydazynowe |
| DK3236972T3 (en) | 2014-12-26 | 2021-10-04 | Univ Emory | Antivirale N4-hydroxycytidin-derivativer |
| CN106554350B (zh) * | 2015-09-29 | 2019-12-20 | 四川海思科制药有限公司 | 具有β2激动活性的苯并杂环衍生物及其制法和应用 |
| 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 |
| JP6804790B1 (ja) | 2017-12-07 | 2020-12-23 | エモリー ユニバーシティー | Ｎ４−ヒドロキシシチジンおよび誘導体ならびにそれらに関連する抗ウイルス用途 |
| CN112250557A (zh) * | 2020-10-23 | 2021-01-22 | 徐州工程学院 | 一种高效合成1,6-二烯-3-酮衍生物的方法 |
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2011
- 2011-05-09 EP EP11719748A patent/EP2569285A1/en not_active Withdrawn
- 2011-05-09 CA CA2796826A patent/CA2796826A1/en not_active Abandoned
- 2011-05-09 NZ NZ603136A patent/NZ603136A/en not_active IP Right Cessation
- 2011-05-09 AU AU2011253203A patent/AU2011253203A1/en not_active Abandoned
- 2011-05-09 US US13/103,577 patent/US8394829B2/en not_active Expired - Fee Related
- 2011-05-09 UY UY0001033372A patent/UY33372A/es not_active Application Discontinuation
- 2011-05-09 WO PCT/US2011/035738 patent/WO2011143105A1/en not_active Ceased
- 2011-05-09 AR ARP110101593A patent/AR081026A1/es unknown
- 2011-05-09 JP JP2013510204A patent/JP5807058B2/ja not_active Expired - Fee Related
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2012
- 2012-09-14 US US13/619,636 patent/US20130012504A1/en not_active Abandoned
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2015
- 2015-03-09 JP JP2015045538A patent/JP2015131833A/ja active Pending
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| Publication number | Publication date |
|---|---|
| EP2569285A1 (en) | 2013-03-20 |
| JP2013526520A (ja) | 2013-06-24 |
| US20110275622A1 (en) | 2011-11-10 |
| NZ603136A (en) | 2014-11-28 |
| UY33372A (es) | 2011-12-30 |
| WO2011143105A1 (en) | 2011-11-17 |
| AR081026A1 (es) | 2012-05-30 |
| US20130012504A1 (en) | 2013-01-10 |
| US8394829B2 (en) | 2013-03-12 |
| CA2796826A1 (en) | 2011-11-17 |
| JP2015131833A (ja) | 2015-07-23 |
| JP5807058B2 (ja) | 2015-11-10 |
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