CZ303808B6 - Nové pyrazolové deriváty jako farmaceutická cinidla - Google Patents

Info

Publication number

CZ303808B6

CZ303808B6 CZ20033128A CZ20033128A CZ303808B6 CZ 303808 B6 CZ303808 B6 CZ 303808B6 CZ 20033128 A CZ20033128 A CZ 20033128A CZ 20033128 A CZ20033128 A CZ 20033128A CZ 303808 B6 CZ303808 B6 CZ 303808B6

Authority

CZ

Czechia

Prior art keywords

dihydro

pyrrolo

pyrazol

pyridin

quinoline

Prior art date

2001-05-24

Links

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• Global Dossier
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• 239000008177 pharmaceutical agent Substances 0.000 title abstract description 3
• 150000003233 pyrroles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 219
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
• -1 aminophenyl Chemical group 0.000 claims description 707
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 515
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 510
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 232
• 229910052739 hydrogen Inorganic materials 0.000 claims description 130
• 239000001257 hydrogen Substances 0.000 claims description 130
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 108
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 106
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 72
• 229910052757 nitrogen Inorganic materials 0.000 claims description 69
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 62
• WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 claims description 62
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 59
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
• 125000000217 alkyl group Chemical group 0.000 claims description 42
• 125000003118 aryl group Chemical group 0.000 claims description 42
• HOGJMYWGRCJUQW-UHFFFAOYSA-N 4-(2-pyridin-2-yl-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-7-carboxylic acid Chemical compound C=1C=NC2=CC(C(=O)O)=CC=C2C=1C1=C2CCCN2N=C1C1=CC=CC=N1 HOGJMYWGRCJUQW-UHFFFAOYSA-N 0.000 claims description 41
• HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 40
• 150000002367 halogens Chemical class 0.000 claims description 37
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 33
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 32
• 239000002253 acid Substances 0.000 claims description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 28
• 150000001412 amines Chemical class 0.000 claims description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 25
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
• 150000001408 amides Chemical class 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 238000006467 substitution reaction Methods 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 20
• 150000002148 esters Chemical class 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 15
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 15
• 150000004702 methyl esters Chemical class 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims description 14
• 150000003857 carboxamides Chemical class 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
• 229940080818 propionamide Drugs 0.000 claims description 13
• 229910005965 SO 2 Inorganic materials 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 12
• RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 12
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 11
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 11
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 11
• 150000003217 pyrazoles Chemical class 0.000 claims description 11
• FBNVOSBSLQPUBQ-UHFFFAOYSA-N quinolin-1-ium-7-sulfonate Chemical compound C1=CC=NC2=CC(S(=O)(=O)O)=CC=C21 FBNVOSBSLQPUBQ-UHFFFAOYSA-N 0.000 claims description 11
• XCRPPAPDRUBKRJ-UHFFFAOYSA-N quinolin-7-ol Chemical compound C1=CC=NC2=CC(O)=CC=C21 XCRPPAPDRUBKRJ-UHFFFAOYSA-N 0.000 claims description 11
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 10
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
• 125000001589 carboacyl group Chemical group 0.000 claims description 10
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 10
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004423 acyloxy group Chemical group 0.000 claims description 9
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 claims description 9
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 8
• RHLRQCJZAXAGML-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl]quinoline-7-carboxylic acid Chemical compound CC1=CC=CC(C=2C(=C3CCCN3N=2)C=2C3=CC=C(C=C3N=CC=2)C(O)=O)=N1 RHLRQCJZAXAGML-UHFFFAOYSA-N 0.000 claims description 8
• PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 150000003222 pyridines Chemical class 0.000 claims description 8
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 8
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 8
• 150000003248 quinolines Chemical class 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 7
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 7
• KJTRXVXWSSPHRV-UHFFFAOYSA-N 4-benzoyl-5-methyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C=2C=CC=CC=2)=C(C)NN1C1=CC=CC=C1 KJTRXVXWSSPHRV-UHFFFAOYSA-N 0.000 claims description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
• 239000005977 Ethylene Substances 0.000 claims description 7
• GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical compound C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 claims description 7
• BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 7
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 239000004202 carbamide Substances 0.000 claims description 7
• IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 7
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 7
• 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 7
• QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims description 6
• IRNAEDHJBNPCEZ-UHFFFAOYSA-N 1-n,1-n,2-trimethylpropane-1,2-diamine Chemical compound CN(C)CC(C)(C)N IRNAEDHJBNPCEZ-UHFFFAOYSA-N 0.000 claims description 6
• FHPLXZDRNSGYSK-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)quinoline Chemical compound N1N=CC=C1C1=CC=C(C=CC=C2)C2=N1 FHPLXZDRNSGYSK-UHFFFAOYSA-N 0.000 claims description 6
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• YOKUGHHDNXZKFC-UHFFFAOYSA-N 4-(2-pyridin-2-yl-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-6-carboxylic acid Chemical compound C12=CC(C(=O)O)=CC=C2N=CC=C1C1=C2CCCN2N=C1C1=CC=CC=N1 YOKUGHHDNXZKFC-UHFFFAOYSA-N 0.000 claims description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
• YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims description 6
• 150000007942 carboxylates Chemical class 0.000 claims description 6
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 6
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 6
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 6
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims description 6
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 5
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
• ZTQKCBQVGOJTSS-UHFFFAOYSA-N 4-(2-pyridin-2-yl-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-7-sulfonic acid Chemical compound C=1C=NC2=CC(S(=O)(=O)O)=CC=C2C=1C1=C2CCCN2N=C1C1=CC=CC=N1 ZTQKCBQVGOJTSS-UHFFFAOYSA-N 0.000 claims description 5
• MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 claims description 5
• PUCPFBRDUSBTHF-UHFFFAOYSA-N 7-(3-chloropropoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)quinoline Chemical compound C=1C=NC2=CC(OCCCCl)=CC=C2C=1C1=C2CCCN2N=C1C1=CC=CC=N1 PUCPFBRDUSBTHF-UHFFFAOYSA-N 0.000 claims description 5
• 239000005711 Benzoic acid Substances 0.000 claims description 5
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 235000010233 benzoic acid Nutrition 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
• ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 claims description 4
• ZHNYCSVPOLBQEU-UHFFFAOYSA-N 2-pyridin-2-yl-3-quinolin-4-yl-6,7-dihydro-4h-pyrazolo[5,1-c][1,4]oxazine Chemical compound C=1C=NC2=CC=CC=C2C=1C1=C2COCCN2N=C1C1=CC=CC=N1 ZHNYCSVPOLBQEU-UHFFFAOYSA-N 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• OXRWANGTCXYDBZ-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl]quinoline-6-carboxylic acid Chemical compound CC1=CC=CC(C=2C(=C3CCCN3N=2)C=2C3=CC(=CC=C3N=CC=2)C(O)=O)=N1 OXRWANGTCXYDBZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000002541 furyl group Chemical class 0.000 claims description 4
• PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 4
• QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 claims description 4
• HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 claims description 4
• 235000019260 propionic acid Nutrition 0.000 claims description 4
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 238000011282 treatment Methods 0.000 claims description 4
• OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 claims description 3
• RRQHLOZQFPWDCA-UHFFFAOYSA-N 1-n,1-n-dimethylpropane-1,2-diamine Chemical compound CC(N)CN(C)C RRQHLOZQFPWDCA-UHFFFAOYSA-N 0.000 claims description 3
• KAUABWYBFARJAF-UHFFFAOYSA-N 1h-pyrazol-4-ol Chemical compound OC=1C=NNC=1 KAUABWYBFARJAF-UHFFFAOYSA-N 0.000 claims description 3
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• YXZNVLYXBIIIOB-UHFFFAOYSA-N methyl 3-fluorobenzoate Chemical compound COC(=O)C1=CC=CC(F)=C1 YXZNVLYXBIIIOB-UHFFFAOYSA-N 0.000 description 1
• QNCMNBKPTMWICH-UHFFFAOYSA-N methyl 4-(2-pyridin-2-yl-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2N=CC=C1C1=C2CCCN2N=C1C1=CC=CC=N1 QNCMNBKPTMWICH-UHFFFAOYSA-N 0.000 description 1
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• TWUXBVMXSBEKHA-UHFFFAOYSA-N methyl 6-chloropyridine-2-carboxylate Chemical compound COC(=O)C1=CC=CC(Cl)=N1 TWUXBVMXSBEKHA-UHFFFAOYSA-N 0.000 description 1
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• RFTMIAAQVNHPBE-UHFFFAOYSA-N n-(benzhydrylideneamino)-5-[tert-butyl(dimethyl)silyl]oxy-4-hydroxypentanamide Chemical compound C=1C=CC=CC=1C(=NNC(=O)CCC(O)CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1 RFTMIAAQVNHPBE-UHFFFAOYSA-N 0.000 description 1
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• BEENTKNKPLFNKS-UHFFFAOYSA-N n-ethyl-n'-(3-pyrrolidin-1-ylpropyl)methanediimine Chemical compound CCN=C=NCCCN1CCCC1 BEENTKNKPLFNKS-UHFFFAOYSA-N 0.000 description 1
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