NO314303B1 - Fremgangsmåte for syntese av kinolinderivater - Google Patents
Fremgangsmåte for syntese av kinolinderivater Download PDFInfo
- Publication number
- NO314303B1 NO314303B1 NO20001387A NO20001387A NO314303B1 NO 314303 B1 NO314303 B1 NO 314303B1 NO 20001387 A NO20001387 A NO 20001387A NO 20001387 A NO20001387 A NO 20001387A NO 314303 B1 NO314303 B1 NO 314303B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- reaction mixture
- alkyl
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 52
- 230000008569 process Effects 0.000 title claims description 16
- 230000015572 biosynthetic process Effects 0.000 title description 16
- 238000003786 synthesis reaction Methods 0.000 title description 14
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 158
- 239000011541 reaction mixture Substances 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- -1 cyano, carboxy Chemical group 0.000 claims description 22
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 22
- BIAVGWDGIJKWRM-FQEVSTJZSA-N 3-hydroxy-2-phenyl-n-[(1s)-1-phenylpropyl]quinoline-4-carboxamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(O)C=1C1=CC=CC=C1 BIAVGWDGIJKWRM-FQEVSTJZSA-N 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 150000003839 salts Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 230000003213 activating effect Effects 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000004442 acylamino group Chemical group 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- XAPRFLSJBSXESP-UHFFFAOYSA-N oxycinchophen Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=C(O)C=1C1=CC=CC=C1 XAPRFLSJBSXESP-UHFFFAOYSA-N 0.000 claims description 9
- 150000003248 quinolines Chemical class 0.000 claims description 9
- AQFLVLHRZFLDDV-VIFPVBQESA-N (1s)-1-phenylpropan-1-amine Chemical compound CC[C@H](N)C1=CC=CC=C1 AQFLVLHRZFLDDV-VIFPVBQESA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 8
- 125000005518 carboxamido group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- PMZKDGRAZFDNFC-BVMKMSJKSA-N C=1C=CC=CC=1C(CC)NC(=O)C([C@@]1(O)C=2N=C3C=CC=CC3=CC=2)(C(O)=O)C2=CC=CC=C2NC1(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C(CC)NC(=O)C([C@@]1(O)C=2N=C3C=CC=CC3=CC=2)(C(O)=O)C2=CC=CC=C2NC1(C=1C=CC=CC=1)C1=CC=CC=C1 PMZKDGRAZFDNFC-BVMKMSJKSA-N 0.000 claims description 6
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- BHCSUEHQURQVLD-BDQAORGHSA-N 3-hydroxy-2-phenyl-n-[(1s)-1-phenylpropyl]quinoline-4-carboxamide;hydrochloride Chemical group Cl.N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(O)C=1C1=CC=CC=C1 BHCSUEHQURQVLD-BDQAORGHSA-N 0.000 claims description 3
- FZFIIACJTIBJMH-UHFFFAOYSA-N ethyl 3-acetyloxy-2-phenylquinoline-4-carboxylate Chemical compound N=1C2=CC=CC=C2C(C(=O)OCC)=C(OC(C)=O)C=1C1=CC=CC=C1 FZFIIACJTIBJMH-UHFFFAOYSA-N 0.000 claims description 3
- UPTYCYWTFGTCCG-UHFFFAOYSA-N 5-(1-piperazinylsulfonyl)isoquinoline Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCNCC1 UPTYCYWTFGTCCG-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 229910001868 water Inorganic materials 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 13
- 230000008878 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
- 229940061720 alpha hydroxy acid Drugs 0.000 description 7
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 102000002003 Neurokinin-3 Receptors Human genes 0.000 description 5
- 108010040716 Neurokinin-3 Receptors Proteins 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- BGAXCPSNMHVHJC-UHFFFAOYSA-N phenacyl acetate Chemical class CC(=O)OCC(=O)C1=CC=CC=C1 BGAXCPSNMHVHJC-UHFFFAOYSA-N 0.000 description 5
- 239000002464 receptor antagonist Substances 0.000 description 5
- 229940044551 receptor antagonist Drugs 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
- 229910001863 barium hydroxide Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 229940095643 calcium hydroxide Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 2
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical compound COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 206010046543 Urinary incontinence Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011210 chromatographic step Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- MXNVEJDRXSFZQB-UHFFFAOYSA-N 3-hydroxyquinoline-4-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=NC2=C1 MXNVEJDRXSFZQB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
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- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000251778 Squalus acanthias Species 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- INKDAKMSOSCDGL-UHFFFAOYSA-N [O].OC1=CC=CC=C1 Chemical compound [O].OC1=CC=CC=C1 INKDAKMSOSCDGL-UHFFFAOYSA-N 0.000 description 1
- IMRFHKJOBUPLSP-UHFFFAOYSA-N [amino(hydroxy)-lambda3-chloranyl]oxymethane Chemical compound COCl(N)O IMRFHKJOBUPLSP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000036428 airway hyperreactivity Effects 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 239000012467 final product Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
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- 150000003948 formamides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000013638 trimer Substances 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
- C07D215/20—Oxygen atoms
-
- 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
- C07D215/36—Sulfur atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- 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
- C07D215/38—Nitrogen atoms
-
- 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
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5930397P | 1997-09-17 | 1997-09-17 | |
| PCT/US1998/019434 WO1999014196A1 (en) | 1997-09-17 | 1998-09-17 | Method for the synthesis of quinoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20001387D0 NO20001387D0 (no) | 2000-03-16 |
| NO20001387L NO20001387L (no) | 2000-03-16 |
| NO314303B1 true NO314303B1 (no) | 2003-03-03 |
Family
ID=22022126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20001387A NO314303B1 (no) | 1997-09-17 | 2000-03-16 | Fremgangsmåte for syntese av kinolinderivater |
Country Status (32)
| Country | Link |
|---|---|
| US (6) | US6335448B1 (ru) |
| EP (1) | EP1017676B1 (ru) |
| JP (1) | JP2001516744A (ru) |
| KR (1) | KR20010024031A (ru) |
| CN (1) | CN1125815C (ru) |
| AP (1) | AP1201A (ru) |
| AR (1) | AR015445A1 (ru) |
| AT (1) | ATE353879T1 (ru) |
| AU (1) | AU744538B2 (ru) |
| BG (1) | BG104243A (ru) |
| BR (1) | BR9812085A (ru) |
| CA (1) | CA2303026A1 (ru) |
| DE (1) | DE69837100T2 (ru) |
| DZ (1) | DZ2607A1 (ru) |
| EA (1) | EA002633B1 (ru) |
| ES (1) | ES2283072T3 (ru) |
| HU (1) | HUP0004855A3 (ru) |
| ID (1) | ID24140A (ru) |
| IL (1) | IL134991A0 (ru) |
| MA (1) | MA24644A1 (ru) |
| MY (1) | MY120237A (ru) |
| NO (1) | NO314303B1 (ru) |
| NZ (1) | NZ503307A (ru) |
| OA (1) | OA11340A (ru) |
| PE (1) | PE129299A1 (ru) |
| PL (1) | PL339340A1 (ru) |
| SK (1) | SK3672000A3 (ru) |
| TR (1) | TR200000720T2 (ru) |
| TW (1) | TW509678B (ru) |
| UY (2) | UY25174A1 (ru) |
| WO (1) | WO1999014196A1 (ru) |
| ZA (1) | ZA988455B (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AP1201A (en) * | 1997-09-17 | 2003-09-01 | Smithkline Beecham Corp | Method for the synthesis of quinoline derivatives. |
| WO2000058313A1 (en) | 1999-03-29 | 2000-10-05 | Neurogen Corporation | 4-substituted quinoline derivatives as gaba receptor ligands |
| GEP20084360B (en) | 2004-02-04 | 2008-04-29 | Pfizer Prod Inc | Substituted quinoline compounds |
| CA2611060A1 (en) * | 2005-06-03 | 2006-12-07 | R. Thomas Simpson | Quinoline derivatives as nk3 antagonists |
| US20080194623A1 (en) * | 2005-08-02 | 2008-08-14 | Labaw Clifford S | Method for the Synthesis of Quinoline Derivatives |
| JP2009504642A (ja) * | 2005-08-11 | 2009-02-05 | アストラゼネカ・アクチエボラーグ | Ｎｋ−３受容体の調節剤としてのオキソピリジルキノリンアミド |
| JP2009508944A (ja) * | 2005-09-21 | 2009-03-05 | アストラゼネカ・アクチエボラーグ | Ｎｋ−３受容体リガンドとしてのｎ−オキソ複素環及びｎ−オキソ−アルキルキノリン−４−カルボキシアミド類 |
| AR057130A1 (es) * | 2005-09-21 | 2007-11-14 | Astrazeneca Ab | Quinolinas de alquilsulfoxido y una composicion farmaceutica |
| US20090054445A1 (en) * | 2006-01-27 | 2009-02-26 | Astrazeneca Ab | Amide Substituted Quinolines |
| CN102702099A (zh) * | 2012-06-21 | 2012-10-03 | 江苏恩华药业股份有限公司 | (s)-3-羟基-2-苯基-n-(1-苯基丙基)喹啉-4-甲酰胺的制备方法 |
| CN102924375B (zh) * | 2012-06-21 | 2015-02-18 | 江苏恩华药业股份有限公司 | Talnetant中间体及其制备方法和应用 |
| CN103214416A (zh) * | 2013-04-26 | 2013-07-24 | 扬州大学 | 一种合成多取代喹啉类化合物的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776290A (en) * | 1957-01-01 | Hydroxy cevchoninates and carboxylic | ||
| KR100316571B1 (ko) * | 1994-05-27 | 2002-05-30 | 파올로 비지, 엔리꼬 카쭐라니 | 타키키닌nk3수용체길항제로서퀴놀린유도체 |
| US5627193A (en) * | 1995-02-09 | 1997-05-06 | Mitsui Toatsu Chemicals, Inc. | Quinoline-4-carbonylguanidine derivatives, process for producing the same and pharmaceutical preparations containing the compounds |
| AP1201A (en) * | 1997-09-17 | 2003-09-01 | Smithkline Beecham Corp | Method for the synthesis of quinoline derivatives. |
-
1998
- 1998-05-08 AP APAP/P/2000/001767A patent/AP1201A/en active
- 1998-09-08 UY UY25174A patent/UY25174A1/es not_active Application Discontinuation
- 1998-09-08 MA MA25246A patent/MA24644A1/fr unknown
- 1998-09-11 PE PE1998000868A patent/PE129299A1/es not_active Application Discontinuation
- 1998-09-14 DZ DZ980217A patent/DZ2607A1/xx active
- 1998-09-15 MY MYPI98004207A patent/MY120237A/en unknown
- 1998-09-16 AR ARP980104603A patent/AR015445A1/es not_active Application Discontinuation
- 1998-09-16 ZA ZA988455A patent/ZA988455B/xx unknown
- 1998-09-17 EA EA200000322A patent/EA002633B1/ru not_active IP Right Cessation
- 1998-09-17 HU HU0004855A patent/HUP0004855A3/hu unknown
- 1998-09-17 KR KR1020007002766A patent/KR20010024031A/ko not_active Application Discontinuation
- 1998-09-17 DE DE69837100T patent/DE69837100T2/de not_active Expired - Lifetime
- 1998-09-17 AT AT98947099T patent/ATE353879T1/de not_active IP Right Cessation
- 1998-09-17 JP JP2000511747A patent/JP2001516744A/ja active Pending
- 1998-09-17 EP EP98947099A patent/EP1017676B1/en not_active Expired - Lifetime
- 1998-09-17 TR TR2000/00720T patent/TR200000720T2/xx unknown
- 1998-09-17 ES ES98947099T patent/ES2283072T3/es not_active Expired - Lifetime
- 1998-09-17 IL IL13499198A patent/IL134991A0/xx unknown
- 1998-09-17 CN CN98810978A patent/CN1125815C/zh not_active Expired - Fee Related
- 1998-09-17 CA CA002303026A patent/CA2303026A1/en not_active Abandoned
- 1998-09-17 ID IDW20000498A patent/ID24140A/id unknown
- 1998-09-17 BR BR9812085-9A patent/BR9812085A/pt not_active IP Right Cessation
- 1998-09-17 AU AU93958/98A patent/AU744538B2/en not_active Ceased
- 1998-09-17 SK SK367-2000A patent/SK3672000A3/sk unknown
- 1998-09-17 PL PL98339340A patent/PL339340A1/xx unknown
- 1998-09-17 WO PCT/US1998/019434 patent/WO1999014196A1/en active IP Right Grant
- 1998-09-17 US US09/508,358 patent/US6335448B1/en not_active Expired - Fee Related
- 1998-09-17 NZ NZ503307A patent/NZ503307A/en unknown
- 1998-09-29 TW TW087114858A patent/TW509678B/zh not_active IP Right Cessation
-
1999
- 1999-02-26 UY UY25407A patent/UY25407A1/es unknown
-
2000
- 2000-03-15 BG BG104243A patent/BG104243A/xx unknown
- 2000-03-16 OA OA1200000078A patent/OA11340A/en unknown
- 2000-03-16 NO NO20001387A patent/NO314303B1/no not_active IP Right Cessation
-
2001
- 2001-10-17 US US09/981,185 patent/US20020038029A1/en not_active Abandoned
-
2002
- 2002-06-17 US US10/174,458 patent/US20020173657A1/en not_active Abandoned
-
2003
- 2003-05-20 US US10/441,708 patent/US20040049031A1/en not_active Abandoned
-
2005
- 2005-03-30 US US11/093,701 patent/US20050171152A1/en not_active Abandoned
-
2006
- 2006-04-28 US US11/413,932 patent/US20060189809A1/en not_active Abandoned
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