ZA200404066B - 3,4-disubstituted, 3,5-disubstituted and 3,4,5-substituted piperidines and piperazines - Google Patents
3,4-disubstituted, 3,5-disubstituted and 3,4,5-substituted piperidines and piperazines Download PDFInfo
- Publication number
- ZA200404066B ZA200404066B ZA200404066A ZA200404066A ZA200404066B ZA 200404066 B ZA200404066 B ZA 200404066B ZA 200404066 A ZA200404066 A ZA 200404066A ZA 200404066 A ZA200404066 A ZA 200404066A ZA 200404066 B ZA200404066 B ZA 200404066B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- group
- chz
- Prior art date
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- 150000004885 piperazines Chemical class 0.000 title description 4
- 150000003053 piperidines Chemical class 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 643
- 150000001875 compounds Chemical class 0.000 claims description 182
- -1 1l-naphthyl Chemical group 0.000 claims description 131
- 125000003545 alkoxy group Chemical group 0.000 claims description 125
- 125000001424 substituent group Chemical group 0.000 claims description 119
- 229910052799 carbon Inorganic materials 0.000 claims description 102
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 96
- 208000024827 Alzheimer disease Diseases 0.000 claims description 62
- 125000003342 alkenyl group Chemical group 0.000 claims description 55
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 51
- 201000010099 disease Diseases 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 49
- 206010012289 Dementia Diseases 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 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 25
- 208000010877 cognitive disease Diseases 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 230000003412 degenerative effect Effects 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 14
- 201000010374 Down Syndrome Diseases 0.000 claims description 12
- 206010044688 Trisomy 21 Diseases 0.000 claims description 12
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 12
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 10
- 210000004558 lewy body Anatomy 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 8
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
- 230000002792 vascular Effects 0.000 claims description 8
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 7
- 208000032843 Hemorrhage Diseases 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 230000001054 cortical effect Effects 0.000 claims description 7
- 230000007850 degeneration Effects 0.000 claims description 7
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 7
- 230000000306 recurrent effect Effects 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims description 6
- 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 6
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- 208000018282 ACys amyloidosis Diseases 0.000 claims description 4
- 208000007487 Familial Cerebral Amyloid Angiopathy Diseases 0.000 claims description 4
- 208000032849 Hereditary cerebral hemorrhage with amyloidosis Diseases 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000005992 dihydrobenzisothiazinyl group Chemical group 0.000 claims description 4
- 125000005993 dihydrobenzisoxazinyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005994 isobenzotetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000005995 isobenzotetrahydrothienyl group Chemical group 0.000 claims description 4
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 4
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 claims description 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 2
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims description 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000003151 isocoumarinyl group Chemical group C1(=O)OC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 18
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 3
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- BGTWFLFIGDHQLW-UHFFFAOYSA-N naphthalene-1-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)O)=CC=CC2=C1 BGTWFLFIGDHQLW-UHFFFAOYSA-N 0.000 claims 2
- XLBBQFVOBCYVAO-UHFFFAOYSA-N piperidin-3-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCCNC1 XLBBQFVOBCYVAO-UHFFFAOYSA-N 0.000 claims 2
- QQYNGKGFOZQMHD-UHFFFAOYSA-N (3-methoxyphenyl) acetate Chemical compound COC1=CC=CC(OC(C)=O)=C1 QQYNGKGFOZQMHD-UHFFFAOYSA-N 0.000 claims 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- GIVGMBPKVYSOKZ-UHFFFAOYSA-N 2-ethylhexanoic acid;hydrochloride Chemical compound Cl.CCCCC(CC)C(O)=O GIVGMBPKVYSOKZ-UHFFFAOYSA-N 0.000 claims 1
- RWFXDZIZBGXSNL-UHFFFAOYSA-N 2-methoxybenzoic acid;hydrochloride Chemical compound Cl.COC1=CC=CC=C1C(O)=O RWFXDZIZBGXSNL-UHFFFAOYSA-N 0.000 claims 1
- JCGGLXLQYKVCJQ-UHFFFAOYSA-N 2-methylbenzoic acid;hydrochloride Chemical compound Cl.CC1=CC=CC=C1C(O)=O JCGGLXLQYKVCJQ-UHFFFAOYSA-N 0.000 claims 1
- DVPLHEDOLZCKHJ-UHFFFAOYSA-N 2-phenoxyacetic acid;hydrochloride Chemical compound Cl.OC(=O)COC1=CC=CC=C1 DVPLHEDOLZCKHJ-UHFFFAOYSA-N 0.000 claims 1
- RHOPUUFLVKWWFP-UHFFFAOYSA-N 2-phenylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CC=C1 RHOPUUFLVKWWFP-UHFFFAOYSA-N 0.000 claims 1
- ATDBEHGVBAPKRE-UHFFFAOYSA-N 3-(2-cyclohexylethoxy)-4-(furan-3-yl)piperidine Chemical compound C1NCCC(C2=COC=C2)C1OCCC1CCCCC1 ATDBEHGVBAPKRE-UHFFFAOYSA-N 0.000 claims 1
- FIUFLISGGHNPSM-UHFFFAOYSA-M 3-(4-methoxyphenyl)propanoate Chemical compound COC1=CC=C(CCC([O-])=O)C=C1 FIUFLISGGHNPSM-UHFFFAOYSA-M 0.000 claims 1
- FQXQBFUUVCDIRK-UHFFFAOYSA-M 3-(trifluoromethyl)benzoate Chemical compound [O-]C(=O)C1=CC=CC(C(F)(F)F)=C1 FQXQBFUUVCDIRK-UHFFFAOYSA-M 0.000 claims 1
- GURJTLNIHIJDTD-UHFFFAOYSA-N 3-benzyl-5-[(3,5-difluorophenyl)methoxy]piperidine;hydrochloride Chemical compound Cl.FC1=CC(F)=CC(COC2CC(CC=3C=CC=CC=3)CNC2)=C1 GURJTLNIHIJDTD-UHFFFAOYSA-N 0.000 claims 1
- OJTPAAHKZRTSMR-UHFFFAOYSA-N 3-benzyl-5-[(3-methylphenyl)methoxy]piperidine;hydrochloride Chemical compound Cl.CC1=CC=CC(COC2CC(CC=3C=CC=CC=3)CNC2)=C1 OJTPAAHKZRTSMR-UHFFFAOYSA-N 0.000 claims 1
- QCYSDQPAJYSSNZ-UHFFFAOYSA-N 3-benzyl-5-[[4-(trifluoromethyl)phenyl]methoxy]piperidine;hydrochloride Chemical compound Cl.C1=CC(C(F)(F)F)=CC=C1COC1CC(CC=2C=CC=CC=2)CNC1 QCYSDQPAJYSSNZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- LXWNTLBMNCXRQN-UHFFFAOYSA-N 4'-fluoro-1,1'-biphenyl-4-carboxylic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1 LXWNTLBMNCXRQN-UHFFFAOYSA-N 0.000 claims 1
- QUVFHVHLCFFINS-UHFFFAOYSA-N 4-(3-aminophenyl)benzoic acid Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)C(O)=O)=C1 QUVFHVHLCFFINS-UHFFFAOYSA-N 0.000 claims 1
- SJIVTXJWSYIMDG-UHFFFAOYSA-N 4-(3-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(Cl)=C1 SJIVTXJWSYIMDG-UHFFFAOYSA-N 0.000 claims 1
- RMDRPJICNOYAKA-UHFFFAOYSA-N 4-(furan-3-yl)-3-phenylmethoxypiperidine Chemical compound C=1C=CC=CC=1COC1CNCCC1C=1C=COC=1 RMDRPJICNOYAKA-UHFFFAOYSA-N 0.000 claims 1
- JJSAEPYHAATHJA-UHFFFAOYSA-N 4-iodobenzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C(I)C=C1 JJSAEPYHAATHJA-UHFFFAOYSA-N 0.000 claims 1
- ZJARCXJVUWYDPB-UHFFFAOYSA-N 4-phenoxybenzoic acid;hydrochloride Chemical compound Cl.C1=CC(C(=O)O)=CC=C1OC1=CC=CC=C1 ZJARCXJVUWYDPB-UHFFFAOYSA-N 0.000 claims 1
- SRAWGZGWKCCCKW-UHFFFAOYSA-N 4-phenylbenzoic acid;hydrochloride Chemical compound Cl.C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 SRAWGZGWKCCCKW-UHFFFAOYSA-N 0.000 claims 1
- DZLGZIGLHCRIMF-UHFFFAOYSA-M 4-pyridin-4-ylbenzoate Chemical compound C1=CC(C(=O)[O-])=CC=C1C1=CC=NC=C1 DZLGZIGLHCRIMF-UHFFFAOYSA-M 0.000 claims 1
- PNLXQFOXOPGOGI-UHFFFAOYSA-N 4-tert-butylbenzoic acid;hydrochloride Chemical compound Cl.CC(C)(C)C1=CC=C(C(O)=O)C=C1 PNLXQFOXOPGOGI-UHFFFAOYSA-N 0.000 claims 1
- PTNWHEHDBNNKEO-UHFFFAOYSA-N 5-thiophen-2-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CS1 PTNWHEHDBNNKEO-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- RCBQTIDFCCOFBL-UHFFFAOYSA-N Cl.OC(=O)c1cccc(c1)-c1ccccc1 Chemical compound Cl.OC(=O)c1cccc(c1)-c1ccccc1 RCBQTIDFCCOFBL-UHFFFAOYSA-N 0.000 claims 1
- RENWPPCDYSOUFP-UHFFFAOYSA-N Cl.S1C(=CC=C1)C1=CC=C(C(=O)O)C=C1 Chemical compound Cl.S1C(=CC=C1)C1=CC=C(C(=O)O)C=C1 RENWPPCDYSOUFP-UHFFFAOYSA-N 0.000 claims 1
- 101100149256 Mus musculus Sema6b gene Proteins 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 235000010582 Pisum sativum Nutrition 0.000 claims 1
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Landscapes
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
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| CN (1) | CN1863530A (zh) |
| ZA (1) | ZA200404066B (zh) |
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| KR20110048491A (ko) * | 2008-07-28 | 2011-05-11 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 스피로아미노디하이드로티아진 유도체들 |
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| CN1863530A (zh) | 2006-11-15 |
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