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
- GHNYHFGMOINDRA-UHFFFAOYSA-N n-[4-[4-(6h-benzo[c][1]benzothiepin-11-ylidene)piperidin-1-yl]butyl]-5-pyridin-3-ylpentanamide Chemical compound C1CC(=C2C3=CC=CC=C3SCC3=CC=CC=C32)CCN1CCCCNC(=O)CCCCC1=CC=CN=C1 GHNYHFGMOINDRA-UHFFFAOYSA-N 0.000 description 2
- 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
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 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
- 230000001225 therapeutic effect Effects 0.000 description 2
- 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
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- 206010028980 Neoplasm Diseases 0.000 description 1
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- 239000000443 aerosol Substances 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
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- 239000007938 effervescent tablet Substances 0.000 description 1
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- 210000004392 genitalia Anatomy 0.000 description 1
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- 229940125721 immunosuppressive agent Drugs 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
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- LAYPMCGIWDGYKX-UHFFFAOYSA-N trichloromethyl hydrogen carbonate Chemical compound OC(=O)OC(Cl)(Cl)Cl LAYPMCGIWDGYKX-UHFFFAOYSA-N 0.000 description 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19756235A DE19756235A1 (de) | 1997-12-17 | 1997-12-17 | Neue piperidinylsubstituierte Pyridylalkan- alken- und -alkincarbonsäureamide |
| DE19756235.3 | 1997-12-17 | ||
| PCT/EP1998/008269 WO1999031060A2 (en) | 1997-12-17 | 1998-12-16 | Piperidinyl-substituted pyridylalkane, alkene and alkine carboxamides as cytostatics and immunesuppressants |
Publications (3)
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| JP2003525853A JP2003525853A (ja) | 2003-09-02 |
| JP2003525853A5 true JP2003525853A5 (https=) | 2006-02-09 |
| JP4570247B2 JP4570247B2 (ja) | 2010-10-27 |
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| Country | Link |
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| EP (1) | EP1044197B1 (https=) |
| JP (1) | JP4570247B2 (https=) |
| AT (1) | ATE323692T1 (https=) |
| AU (1) | AU2162599A (https=) |
| CY (1) | CY1106117T1 (https=) |
| DE (2) | DE19756235A1 (https=) |
| DK (1) | DK1044197T3 (https=) |
| ES (1) | ES2262254T3 (https=) |
| PT (1) | PT1044197E (https=) |
| WO (1) | WO1999031060A2 (https=) |
| ZA (1) | ZA9811241B (https=) |
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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 |
| ATE448226T1 (de) * | 2000-09-01 | 2009-11-15 | Novartis Vaccines & Diagnostic | Aza heterocyclische derivate und ihre therapeutische verwendung |
| DE60115069T2 (de) * | 2000-09-11 | 2006-08-03 | Chiron Corp., Emeryville | Chinolinonderivate als tyrosin-kinase inhibitoren |
| US20030028018A1 (en) * | 2000-09-11 | 2003-02-06 | Chiron Coporation | Quinolinone derivatives |
| WO2002030899A1 (en) * | 2000-10-09 | 2002-04-18 | Novartis Ag | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr3 receptor antagonists |
| EP1330436B1 (en) | 2000-10-09 | 2010-06-30 | Novartis AG | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr3-3 receptor antagonists |
| EP1348434A1 (en) * | 2002-03-27 | 2003-10-01 | Fujisawa Deutschland GmbH | Use of pyridyl amides as inhibitors of angiogenesis |
| JPWO2004011430A1 (ja) * | 2002-07-25 | 2005-11-24 | アステラス製薬株式会社 | ナトリウムチャネル阻害剤 |
| 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 |
| US7825132B2 (en) * | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
| SG148864A1 (en) * | 2002-11-13 | 2009-01-29 | Chiron Corp | Methods of treating cancer and related methods |
| EP1622569B1 (en) | 2003-04-24 | 2015-12-02 | Incyte Corporation | Aza spiro alkane derivatives as inhibitors of metallproteases |
| US20050209247A1 (en) * | 2003-11-07 | 2005-09-22 | Chiron Corporation | Pharmaceutically acceptable salts of quinolinone compounds having improved pharmaceutical properties |
| EP1718306A2 (en) * | 2004-02-20 | 2006-11-08 | Chiron Corporation | Modulation of inflammatory and metastatic processes |
| WO2006115509A2 (en) | 2004-06-24 | 2006-11-02 | Novartis Vaccines And Diagnostics Inc. | Small molecule immunopotentiators and assays for their detection |
| EA200701745A1 (ru) | 2005-03-17 | 2008-06-30 | Пфайзер, Инк. | Циклопропанкарбоксамидные производные |
| EP1885187B1 (en) * | 2005-05-13 | 2013-09-25 | Novartis AG | Methods for treating drug resistant cancer |
| EP2465857B1 (en) * | 2005-05-17 | 2014-06-04 | Novartis AG | Methods for synthesizing heterocyclic compounds |
| BRPI0611375A2 (pt) * | 2005-05-23 | 2010-08-31 | Novartis Ag | formas cristalinas e outras de sais de ácido láctico de 4-amino-5-flúor-3-[6-(4-metilpiperazin-1-il)-1h-benzimid azol-2-il]-1h-quinolin-2-ona |
| 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 |
| ES2657214T3 (es) * | 2008-07-30 | 2018-03-02 | Nitto Denko Corporation | Vehículos de fármacos |
| 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 |
| EP2611804A1 (en) | 2010-09-03 | 2013-07-10 | Forma TM, LLC. | Novel compounds and compositions for the inhibition of nampt |
| CN103270023B (zh) | 2010-09-03 | 2016-11-02 | 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 |
| AR082886A1 (es) | 2010-09-03 | 2013-01-16 | Forma Therapeutics Inc | Compuestos y composiciones farmaceuticas que los contienen |
| RU2616612C2 (ru) | 2011-05-04 | 2017-04-18 | ФОРМА ТиЭм, ЭлЭлСИ | Новые соединения и композиции для ингибирования nampt |
| MX347459B (es) | 2011-05-09 | 2017-04-26 | Forma Tm Llc | Nuevos compuestos y composiciones para la inhibición de 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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| US5260323A (en) | 1990-06-28 | 1993-11-09 | Hoechst Aktiengesellschaft | 2,4- and 2,5-substituted pyridine-N-oxides, processes for their preparation and their use |
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| EP0479601B1 (en) * | 1990-10-05 | 1999-12-15 | Ajinomoto Co., Inc. | Piperidine derivatives and their use as antiarrhythmic agents |
| FR2676053B1 (fr) | 1991-05-03 | 1993-08-27 | Sanofi Elf | Nouveaux composes dialkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| US5246948A (en) | 1991-05-10 | 1993-09-21 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
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-
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 PT PT98965846T patent/PT1044197E/pt unknown
- 1998-12-16 EP EP98965846A patent/EP1044197B1/en not_active Expired - Lifetime
- 1998-12-16 ES ES98965846T patent/ES2262254T3/es not_active Expired - Lifetime
- 1998-12-16 DK DK98965846T patent/DK1044197T3/da active
- 1998-12-16 DE DE69834269T patent/DE69834269T2/de not_active Expired - Lifetime
- 1998-12-16 AU AU21625/99A patent/AU2162599A/en not_active Abandoned
- 1998-12-16 JP JP2000538987A patent/JP4570247B2/ja not_active Expired - Fee Related
- 1998-12-16 WO PCT/EP1998/008269 patent/WO1999031060A2/en not_active Ceased
- 1998-12-16 AT AT98965846T patent/ATE323692T1/de active
-
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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