JP2003525853A5 - - Google Patents
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- JP2003525853A5 JP2003525853A5 JP2000538987A JP2000538987A JP2003525853A5 JP 2003525853 A5 JP2003525853 A5 JP 2003525853A5 JP 2000538987 A JP2000538987 A JP 2000538987A JP 2000538987 A JP2000538987 A JP 2000538987A JP 2003525853 A5 JP2003525853 A5 JP 2003525853A5
- Authority
- JP
- Japan
- Prior art keywords
- fifteen
- alkyl
- hydroxy
- group
- hydrogen
- 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.)
- Granted
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- -1 CThree-C8-Cycloalkyl Chemical group 0.000 description 251
- 229910052739 hydrogen Inorganic materials 0.000 description 85
- 239000001257 hydrogen Substances 0.000 description 85
- 125000003118 aryl group Chemical group 0.000 description 84
- 150000002431 hydrogen Chemical class 0.000 description 71
- 229910052757 nitrogen Inorganic materials 0.000 description 64
- 229910052760 oxygen Inorganic materials 0.000 description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 58
- 229910052717 sulfur Inorganic materials 0.000 description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 54
- 125000000217 alkyl group Chemical group 0.000 description 50
- 125000000623 heterocyclic group Chemical group 0.000 description 48
- 125000006413 ring segment Chemical group 0.000 description 48
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 46
- 239000011737 fluorine Substances 0.000 description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 36
- 229910052736 halogen Inorganic materials 0.000 description 32
- 150000002367 halogens Chemical class 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 31
- 125000004093 cyano group Chemical group *C#N 0.000 description 30
- 229910052731 fluorine Inorganic materials 0.000 description 24
- 125000005842 heteroatom Chemical group 0.000 description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 description 24
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 20
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 20
- 125000003003 spiro group Chemical group 0.000 description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 18
- 125000004076 pyridyl group Chemical group 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 16
- 125000004122 cyclic group Chemical group 0.000 description 16
- 125000001624 naphthyl group Chemical group 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 12
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 description 12
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 12
- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 11
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 125000003282 alkyl amino group Chemical group 0.000 description 10
- 125000001041 indolyl group Chemical group 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 125000003368 amide group Chemical group 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 8
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 8
- 125000004043 oxo group Chemical group O=* 0.000 description 8
- 125000003373 pyrazinyl group Chemical group 0.000 description 8
- 125000002098 pyridazinyl group Chemical group 0.000 description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 6
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000002541 furyl group Chemical group 0.000 description 6
- 125000002883 imidazolyl group Chemical group 0.000 description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 description 6
- 125000000335 thiazolyl group Chemical group 0.000 description 6
- 125000001425 triazolyl group Chemical group 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 5
- SHDIFTVYQLNRLR-UHFFFAOYSA-N 11h-pyrido[3,2-b][1]benzazepine Chemical compound C1=CC2=NC=CC=C2NC2=CC=CC=C21 SHDIFTVYQLNRLR-UHFFFAOYSA-N 0.000 description 4
- VIQDTRXYTKXIMM-UHFFFAOYSA-N 5h-benzo[d][1]benzazepine Chemical compound N1C=CC2=CC=CC=C2C2=CC=CC=C12 VIQDTRXYTKXIMM-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- VETZQUSVLXLLPE-UHFFFAOYSA-N N1=CC=CC=C2NC=CC=C21 Chemical compound N1=CC=CC=C2NC=CC=C21 VETZQUSVLXLLPE-UHFFFAOYSA-N 0.000 description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 4
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 description 4
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 4
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 4
- 125000005945 imidazopyridyl group Chemical group 0.000 description 4
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 4
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 4
- 125000001786 isothiazolyl group Chemical group 0.000 description 4
- 125000000842 isoxazolyl group Chemical group 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000002971 oxazolyl group Chemical group 0.000 description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- JDEUSZPWWMACHZ-UHFFFAOYSA-N pyrido[2,3-e][1,4]diazepin-5-one Chemical compound O=C1N=CC=NC2=NC=CC=C12 JDEUSZPWWMACHZ-UHFFFAOYSA-N 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 125000005493 quinolyl group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 125000006823 (C1-C6) acyl group Chemical group 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 2
- CVEXTAUZJWYDJX-UHFFFAOYSA-N 1,3,4,10-Tetrahydro-9(2H)-acridinone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1CCCC2 CVEXTAUZJWYDJX-UHFFFAOYSA-N 0.000 description 2
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 description 2
- UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 description 2
- DJWDAKFSDBOQJK-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.2]octane Chemical compound C1NC2CCC1NC2 DJWDAKFSDBOQJK-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- GYLMCBOAXJVARF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptane Chemical compound C1C2CCC1NC2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 description 2
- KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical compound C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 description 2
- KYMYKPMRBZQPCG-UHFFFAOYSA-N 3-pyridin-3-yl-n-[4-[4-(5h-thieno[2,3-c][2]benzothiepin-10-ylidene)piperidin-1-yl]butyl]prop-2-enamide Chemical compound C1CC(=C2C3=CC=CC=C3CSC=3SC=CC=32)CCN1CCCCNC(=O)C=CC1=CC=CN=C1 KYMYKPMRBZQPCG-UHFFFAOYSA-N 0.000 description 2
- ABZAKAHITMFTMC-UHFFFAOYSA-N 3-pyridin-3-yl-n-[4-[4-(5h-thieno[2,3-c][2]benzothiepin-10-ylidene)piperidin-1-yl]butyl]propanamide Chemical compound C1CC(=C2C3=CC=CC=C3CSC=3SC=CC=32)CCN1CCCCNC(=O)CCC1=CC=CN=C1 ABZAKAHITMFTMC-UHFFFAOYSA-N 0.000 description 2
- SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 2
- XXRGLCKZBCIEKO-DLMDZQPMSA-N azocine Chemical compound C/1=C/C=C\N=C/C=C\1 XXRGLCKZBCIEKO-DLMDZQPMSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 description 2
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 2
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 2
- 125000005046 dihydronaphthyl group Chemical group 0.000 description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- DLXWMXVHNNIOFN-UHFFFAOYSA-N n-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCC21OCCO2 DLXWMXVHNNIOFN-UHFFFAOYSA-N 0.000 description 2
- LYRLTNWCNOCAJL-UHFFFAOYSA-N n-[4-(4,4-diphenylpiperidin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 LYRLTNWCNOCAJL-UHFFFAOYSA-N 0.000 description 2
- CGAXTMRHPISBOD-UHFFFAOYSA-N n-[4-(4-diphenylphosphoryloxypiperidin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCC1OP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 CGAXTMRHPISBOD-UHFFFAOYSA-N 0.000 description 2
- LPLXNYOOYXDJFK-UHFFFAOYSA-N n-[4-(4-phenylpiperidin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCC1C1=CC=CC=C1 LPLXNYOOYXDJFK-UHFFFAOYSA-N 0.000 description 2
- NGBNRCCMTHHKSH-UHFFFAOYSA-N n-[4-[4-(1h-indol-3-yl)piperidin-1-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C1CC(C=2C3=CC=CC=C3NC=2)CCN1CCCCNC(=O)C=CC1=CC=CN=C1 NGBNRCCMTHHKSH-UHFFFAOYSA-N 0.000 description 2
- ZHLUQUDTCYTYJA-UHFFFAOYSA-N n-[4-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1CCCCNC(=O)C=CC1=CC=CN=C1 ZHLUQUDTCYTYJA-UHFFFAOYSA-N 0.000 description 2
- KYIWUGOKVJFIQC-UHFFFAOYSA-N n-[4-[4-(6h-benzo[c][1]benzothiepin-11-ylidene)piperidin-1-yl]butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CC(=C2C3=CC=CC=C3SCC3=CC=CC=C32)CCN1CCCCNC(=O)CCC1=CC=CN=C1 KYIWUGOKVJFIQC-UHFFFAOYSA-N 0.000 description 2
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- JXJTZTBPTUIBQF-UHFFFAOYSA-N n-[4-[4-(benzotriazol-1-yl)piperidin-1-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C1CC(N2C3=CC=CC=C3N=N2)CCN1CCCCNC(=O)C=CC1=CC=CN=C1 JXJTZTBPTUIBQF-UHFFFAOYSA-N 0.000 description 2
- GQFMOSGSXLGHTK-UHFFFAOYSA-N n-[4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butyl]-2-pyridin-3-yloxyacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C(CC1)CCN1CCCCNC(=O)COC1=CC=CN=C1 GQFMOSGSXLGHTK-UHFFFAOYSA-N 0.000 description 2
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
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- 230000009885 systemic effect Effects 0.000 description 2
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
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- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000021559 Dicerandra Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
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- 239000004480 active ingredient Substances 0.000 description 1
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- 230000001085 cytostatic effect Effects 0.000 description 1
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- 210000004392 genitalia Anatomy 0.000 description 1
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| DE19756235.3 | 1997-12-17 | ||
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| PCT/EP1998/008269 WO1999031060A2 (en) | 1997-12-17 | 1998-12-16 | Piperidinyl-substituted pyridylalkane, alkene and alkine carboxamides as cytostatics and immunesuppressants |
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| PT (1) | PT1044197E (enExample) |
| WO (1) | WO1999031060A2 (enExample) |
| ZA (1) | ZA9811241B (enExample) |
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| EP1031564A1 (en) | 1999-02-26 | 2000-08-30 | Klinge Pharma GmbH | Inhibitors of cellular nicotinamide mononucleotide formation and their use in cancer therapy |
| SE9902765D0 (sv) * | 1999-07-21 | 1999-07-21 | Astra Pharma Prod | Novel compounds |
| WO2002018383A2 (en) * | 2000-09-01 | 2002-03-07 | Chiron Corporation | Aza heterocyclic derivatives and their therapeutic use |
| ATE309996T1 (de) * | 2000-09-11 | 2005-12-15 | Chiron Corp | Chinolinonderivate als tyrosin-kinase inhibitoren |
| US20030028018A1 (en) * | 2000-09-11 | 2003-02-06 | Chiron Coporation | Quinolinone derivatives |
| EP1330436B1 (en) * | 2000-10-09 | 2010-06-30 | Novartis AG | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr3-3 receptor antagonists |
| AU2002215928A1 (en) * | 2000-10-09 | 2002-04-22 | Novartis Pharma Gmbh | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr3 receptor antagonists |
| EP1348434A1 (en) * | 2002-03-27 | 2003-10-01 | Fujisawa Deutschland GmbH | Use of pyridyl amides as inhibitors of angiogenesis |
| AU2003248122A1 (en) * | 2002-07-25 | 2004-02-16 | Kotobuki Pharmaceutical Co., Ltd. | Sodium channel inhibitor |
| US7825132B2 (en) * | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
| EP1539754A4 (en) * | 2002-08-23 | 2009-02-25 | Novartis Vaccines & Diagnostic | BENZIMIDAZOCHINOLINONE AND ITS USE |
| US20050256157A1 (en) * | 2002-08-23 | 2005-11-17 | Chiron Corporation | Combination therapy with CHK1 inhibitors |
| US7838527B2 (en) * | 2002-11-13 | 2010-11-23 | Novartis Vaccines And Diagnostics, Inc. | Methods of treating cancer and related methods |
| GEP20094705B (en) | 2003-04-24 | 2009-06-10 | Incyte Corp | Aza spiro alkane derivatives as inhibitors of metalloproteases |
| JP4890255B2 (ja) * | 2003-11-07 | 2012-03-07 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | 改良された薬物特性を有するキノリノン化合物の薬学的に受容可能な塩 |
| RU2377988C2 (ru) * | 2004-02-20 | 2010-01-10 | Новартис Вэксинес Энд Дайэгностикс, Инк. | Модуляция воспалительных и метастатических процессов |
| EP2583678A3 (en) | 2004-06-24 | 2013-11-13 | Novartis Vaccines and Diagnostics, Inc. | Small molecule immunopotentiators and assays for their detection |
| BRPI0608436A2 (pt) | 2005-03-17 | 2009-12-29 | Pfizer | derivados de n-(n-sulfonilaminometil) ciclopropanocarboxamida utilizáveis para o tratamento de dor |
| KR101319122B1 (ko) | 2005-05-13 | 2013-10-23 | 노파르티스 아게 | 약물 저항성 암을 치료하는 방법 |
| BRPI0610355A2 (pt) * | 2005-05-17 | 2010-06-15 | Novartis Ag | métodos par sintetizar compostos heterocìclicos |
| AU2006249847B2 (en) * | 2005-05-23 | 2012-12-20 | Novartis Ag | Crystalline and other forms of 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one lactic acid salts |
| US7910108B2 (en) * | 2006-06-05 | 2011-03-22 | Incyte Corporation | Sheddase inhibitors combined with CD30-binding immunotherapeutics for the treatment of CD30 positive diseases |
| EP2098231A1 (en) | 2008-03-05 | 2009-09-09 | Topotarget Switzerland SA | Use of NAD formation inhibitors for the treatment of ischemia-reperfusion injury |
| RU2505315C2 (ru) * | 2008-07-30 | 2014-01-27 | Нитто Денко Корпорейшн | Носители лекарственных средств |
| RU2011111728A (ru) | 2008-08-29 | 2012-10-10 | Топотаргет А/С (Dk) | Новые производные мочевины и тиомочевины |
| WO2010066709A1 (en) * | 2008-12-09 | 2010-06-17 | Topotarget A/S | Novel pyridinyl acrylamide derivatives |
| CA2768338A1 (en) | 2009-07-17 | 2011-01-20 | Topotarget A/S | Method for predicting the utility of administering nicotinic acid or a precursor or prodrug thereof to reduce the severity of side-effects of cancer treatment with nicotinamide phosphoribosyltransferase inhibitors |
| JP5881705B2 (ja) | 2010-09-03 | 2016-03-09 | フォーマ ティーエム， エルエルシー． | Ｎａｍｐｔの阻害のための新規化合物及び組成物 |
| CN106986856A (zh) | 2010-09-03 | 2017-07-28 | 福马Tm有限责任公司 | 作为用于治疗疾病诸如癌症的nampt抑制剂的4‑{[(吡啶‑3‑基‑甲基)氨基羰基]氨基}苯‑砜衍生物 |
| KR20130114119A (ko) | 2010-09-03 | 2013-10-16 | 포르마 티엠, 엘엘씨. | Ｎａｍｐｔ의 억제를 위한 신규 화합물 및 조성물 |
| AU2011367222B2 (en) | 2011-05-04 | 2017-04-13 | Forma Tm, Llc | Novel compounds and compositions for the inhibition of NAMPT |
| TW201245188A (en) | 2011-05-09 | 2012-11-16 | Forma Therapeutics Inc | Novel compounds and compositions for the inhibition of NAMPT |
| US9216180B2 (en) | 2012-10-02 | 2015-12-22 | New York University | Pharmaceutical compositions and treatment of genetic diseases associated with nonsense mediated RNA decay |
| CN108299411B (zh) * | 2017-01-13 | 2021-02-05 | 中国人民解放军军事医学科学院毒物药物研究所 | 4,4-二苯基哌啶类化合物或其可药用盐、药物组合物及用途 |
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| DE19624704A1 (de) * | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalkansäureamide |
-
1997
- 1997-12-17 DE DE19756235A patent/DE19756235A1/de not_active Ceased
-
1998
- 1998-12-08 ZA ZA9811241A patent/ZA9811241B/xx unknown
- 1998-12-16 AT AT98965846T patent/ATE323692T1/de active
- 1998-12-16 ES ES98965846T patent/ES2262254T3/es not_active Expired - Lifetime
- 1998-12-16 AU AU21625/99A patent/AU2162599A/en not_active Abandoned
- 1998-12-16 DK DK98965846T patent/DK1044197T3/da active
- 1998-12-16 DE DE69834269T patent/DE69834269T2/de not_active Expired - Lifetime
- 1998-12-16 JP JP2000538987A patent/JP4570247B2/ja not_active Expired - Fee Related
- 1998-12-16 EP EP98965846A patent/EP1044197B1/en not_active Expired - Lifetime
- 1998-12-16 WO PCT/EP1998/008269 patent/WO1999031060A2/en not_active Ceased
- 1998-12-16 PT PT98965846T patent/PT1044197E/pt unknown
-
2000
- 2000-06-16 US US09/595,547 patent/US6593344B1/en not_active Expired - Fee Related
-
2006
- 2006-07-07 CY CY20061100940T patent/CY1106117T1/el unknown
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