DE19756236A1 - Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide - Google Patents
Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamideInfo
- Publication number
- DE19756236A1 DE19756236A1 DE19756236A DE19756236A DE19756236A1 DE 19756236 A1 DE19756236 A1 DE 19756236A1 DE 19756236 A DE19756236 A DE 19756236A DE 19756236 A DE19756236 A DE 19756236A DE 19756236 A1 DE19756236 A1 DE 19756236A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- hydroxy
- piperazin
- alkoxy
- 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.)
- Ceased
Links
- 150000001336 alkenes Chemical class 0.000 title abstract description 3
- 150000001408 amides Chemical class 0.000 title description 7
- -1 alkine acid amides Chemical class 0.000 claims abstract description 359
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 239000003814 drug Substances 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 40
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 17
- 239000000824 cytostatic agent Substances 0.000 claims abstract description 15
- 239000003018 immunosuppressive agent Substances 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims description 135
- 229910052739 hydrogen Inorganic materials 0.000 claims description 135
- 125000003118 aryl group Chemical group 0.000 claims description 118
- 239000000126 substance Substances 0.000 claims description 112
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 100
- 150000002431 hydrogen Chemical class 0.000 claims description 96
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 71
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 68
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 239000000243 solution Substances 0.000 claims description 60
- 239000002904 solvent Substances 0.000 claims description 54
- 239000004480 active ingredient Substances 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 125000006413 ring segment Chemical group 0.000 claims description 45
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 238000002360 preparation method Methods 0.000 claims description 37
- 239000011737 fluorine Substances 0.000 claims description 33
- 229910052731 fluorine Inorganic materials 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 229910005965 SO 2 Inorganic materials 0.000 claims description 31
- 229940079593 drug Drugs 0.000 claims description 31
- 238000000746 purification Methods 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 238000007792 addition Methods 0.000 claims description 28
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 28
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 28
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 26
- 239000000843 powder Substances 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000003254 radicals Chemical class 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 20
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 239000000725 suspension Substances 0.000 claims description 18
- 125000004450 alkenylene group Chemical group 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000002552 dosage form Substances 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 230000001085 cytostatic effect Effects 0.000 claims description 14
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 14
- 239000003826 tablet Substances 0.000 claims description 14
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 13
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 13
- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 239000008101 lactose Substances 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 11
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 11
- 239000003380 propellant Substances 0.000 claims description 11
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 11
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 10
- 150000004677 hydrates Chemical class 0.000 claims description 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 9
- 238000009472 formulation Methods 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 239000002674 ointment Substances 0.000 claims description 9
- 125000002971 oxazolyl group Chemical group 0.000 claims description 9
- 238000002560 therapeutic procedure Methods 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 239000000443 aerosol Substances 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 230000036961 partial effect Effects 0.000 claims description 8
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 7
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 7
- 125000004419 alkynylene group Chemical group 0.000 claims description 7
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 230000001506 immunosuppresive effect Effects 0.000 claims description 7
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 229940071648 metered dose inhaler Drugs 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000010261 cell growth Effects 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- AQNQGBUEVCAVML-UHFFFAOYSA-N oxazepane Chemical compound C1CCNOCC1 AQNQGBUEVCAVML-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 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 claims description 5
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 5
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 5
- 230000003327 cancerostatic effect Effects 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 239000008298 dragée Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 125000005945 imidazopyridyl group Chemical group 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 229940126601 medicinal product Drugs 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 239000007921 spray Substances 0.000 claims description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 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 claims description 4
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 4
- MGEHZOOOVVSDAU-UHFFFAOYSA-N 1h-pyrido[2,3-b][1,4]diazepine Chemical compound N1C=CC=NC2=NC=CC=C12 MGEHZOOOVVSDAU-UHFFFAOYSA-N 0.000 claims description 4
- VWBYXJRDIQCSLW-UHFFFAOYSA-N O=[P](c1ccccc1)c1ccccc1 Chemical group O=[P](c1ccccc1)c1ccccc1 VWBYXJRDIQCSLW-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 claims description 4
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 4
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 4
- 239000007943 implant Substances 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
- 125000004761 (C2-C7) alkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000004763 (C3-C13) dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims description 3
- DJWDAKFSDBOQJK-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.2]octane Chemical compound C1NC2CCC1NC2 DJWDAKFSDBOQJK-UHFFFAOYSA-N 0.000 claims description 3
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- COMRSYCVLKBODY-UHFFFAOYSA-N 3-pyridin-3-yl-n-[4-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)piperazin-1-yl]butyl]prop-2-enamide Chemical compound C1CN(C2C3=CC=CC=C3CCC2)CCN1CCCCNC(=O)C=CC1=CC=CN=C1 COMRSYCVLKBODY-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Transplantation (AREA)
- Oncology (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19756236A DE19756236A1 (de) | 1997-12-17 | 1997-12-17 | Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
| ZA9811235A ZA9811235B (en) | 1997-12-17 | 1998-12-08 | New piperazinyl-substituted pyridylalkane alkene and alkine carboxamides |
| EP98965275A EP1060163B1 (en) | 1997-12-17 | 1998-12-16 | New piperazinyl-substituted pyridylalkane, alkene and alkine carboxamides |
| ES98965275T ES2251794T3 (es) | 1997-12-17 | 1998-12-16 | Nuevas piridilalcano, alqueno y alquina carboxamidas sustituidas con piperazinilo. |
| DK98965275T DK1060163T3 (da) | 1997-12-17 | 1998-12-16 | Nye piperazinyl-substituerede pyridylalkan-, -alken og -alkyncarboxamider |
| DE69831877T DE69831877T2 (de) | 1997-12-17 | 1998-12-16 | Neue piperazinyl-substituierte pyridylalkan, alken and alkin carboxamide |
| PCT/EP1998/008268 WO1999031063A1 (en) | 1997-12-17 | 1998-12-16 | New piperazinyl-substituted pyridylalkane, alkene and alkine carboxamides |
| AU20543/99A AU2054399A (en) | 1997-12-17 | 1998-12-16 | New piperazinyl-substituted pyridylalkane, alkene and alkine carboxamides |
| JP2000538990A JP4855576B2 (ja) | 1997-12-17 | 1998-12-16 | ピペラジニル−置換ピリジルアルカン、アルケンおよびアルキンカルボキサミド類 |
| AT98965275T ATE306473T1 (de) | 1997-12-17 | 1998-12-16 | Neue piperazinyl-substituierte pyridylalkan, alken and alkin carboxamide |
| US09/596,001 US6903118B1 (en) | 1997-12-17 | 2000-06-16 | Piperazinyl-substituted pyridylalkane, alkene and alkine carboxamides |
| JP2011152041A JP2011251976A (ja) | 1997-12-17 | 2011-07-08 | ピペラジニル−置換ピリジルアルカン、アルケンおよびアルキンカルボキサミド類 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19756236A DE19756236A1 (de) | 1997-12-17 | 1997-12-17 | Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19756236A1 true DE19756236A1 (de) | 1999-07-01 |
Family
ID=7852332
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19756236A Ceased DE19756236A1 (de) | 1997-12-17 | 1997-12-17 | Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
| DE69831877T Expired - Lifetime DE69831877T2 (de) | 1997-12-17 | 1998-12-16 | Neue piperazinyl-substituierte pyridylalkan, alken and alkin carboxamide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69831877T Expired - Lifetime DE69831877T2 (de) | 1997-12-17 | 1998-12-16 | Neue piperazinyl-substituierte pyridylalkan, alken and alkin carboxamide |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1060163B1 (https=) |
| JP (2) | JP4855576B2 (https=) |
| AT (1) | ATE306473T1 (https=) |
| AU (1) | AU2054399A (https=) |
| DE (2) | DE19756236A1 (https=) |
| DK (1) | DK1060163T3 (https=) |
| ES (1) | ES2251794T3 (https=) |
| WO (1) | WO1999031063A1 (https=) |
| ZA (1) | ZA9811235B (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000007580A3 (en) * | 1998-08-03 | 2000-05-18 | Gene Kutato Kft N | Pharmaceutical compositions against autoimmune diseases |
| WO2003028728A1 (en) * | 2001-09-28 | 2003-04-10 | Richter Gedeon Vegyészeti Gyár Rt. | 4-(4-substituted piperazinyl-1yl)-butylcarboxamides as d3 dopamine subtype selective ligands |
| EP1348434A1 (en) * | 2002-03-27 | 2003-10-01 | Fujisawa Deutschland GmbH | Use of pyridyl amides as inhibitors of angiogenesis |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19756236A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
| UA65635C2 (uk) * | 1998-09-03 | 2004-04-15 | Н-Гене Кутато Кфт. | НЕНАСИЧЕНІ ПОХІДНІ ГІДРОКСИМОВОЇ КИСЛОТИ, ЩО МАЮТЬ ВЛАСТИВОСТІ ІНГІБІТОРІВ NAD<sup>+</sup>-ADP-РИБОЗИЛТРАНСФЕРАЗИ |
| EP1031564A1 (en) | 1999-02-26 | 2000-08-30 | Klinge Pharma GmbH | Inhibitors of cellular nicotinamide mononucleotide formation and their use in cancer therapy |
| DE10152005A1 (de) | 2001-10-22 | 2003-04-30 | Bayer Cropscience Ag | Pyrazolylsubstituierte Heterocyclen |
| WO2003099272A1 (en) | 2002-05-22 | 2003-12-04 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on alpha-ketoepoxide compounds |
| WO2006115509A2 (en) | 2004-06-24 | 2006-11-02 | Novartis Vaccines And Diagnostics Inc. | Small molecule immunopotentiators and assays for their detection |
| EP2098231A1 (en) | 2008-03-05 | 2009-09-09 | Topotarget Switzerland SA | Use of NAD formation inhibitors for the treatment of ischemia-reperfusion injury |
| JP5688367B2 (ja) | 2008-08-29 | 2015-03-25 | トポターゲット・アクティーゼルスカブＴｏｐｏＴａｒｇｅｔ Ａ／Ｓ | 新規なウレアおよびチオウレア誘導体 |
| 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 |
| PE20140011A1 (es) | 2010-09-03 | 2014-01-31 | Forma Tm Llc | Compuestos y composiciones novedosos para la inhibicion de nampt |
| JP6038792B2 (ja) | 2010-09-03 | 2016-12-07 | フォーマ ティーエム， エルエルシー． | 癌などの疾患の治療のためのｎａｍｐｔ阻害剤としての４−｛［（ピリジン−３−イル−メチル）アミノカルボニル］アミノ｝ベンゼン−スルホン誘導体 |
| CN106243023A (zh) | 2010-09-03 | 2016-12-21 | 福马Tm有限责任公司 | 用于抑制nampt的胍化合物和组合物 |
| RU2017112522A (ru) | 2011-05-04 | 2019-01-24 | ФОРМА ТиЭм, ЭлЭлСИ | Новые соединения и композиции для ингибирования nampt |
| WO2012154194A1 (en) | 2011-05-09 | 2012-11-15 | Forma Tm, Llc | Piperidine derivatives and compositions for the inhibition of nicotinamide phosphoribosyltransferase (nampt) |
| UY35464A (es) | 2013-03-15 | 2014-10-31 | Araxes Pharma Llc | Inhibidores covalentes de kras g12c. |
| CA2915357C (en) | 2013-06-14 | 2023-10-03 | Invictus Oncology Pvt. Ltd. | Lipid-based platinum compounds and nanoparticles |
| TWI659021B (zh) | 2013-10-10 | 2019-05-11 | 亞瑞克西斯製藥公司 | Ｋｒａｓ ｇ１２ｃ之抑制劑 |
| ES2826443T3 (es) * | 2014-09-25 | 2021-05-18 | Araxes Pharma Llc | Inhibidores de proteínas mutantes KRAS G12C |
| JP2018513853A (ja) | 2015-04-10 | 2018-05-31 | アラクセス ファーマ エルエルシー | 置換キナゾリン化合物およびその使用方法 |
| WO2017058902A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| EP3356354A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058807A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| EP3356353A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| US10882847B2 (en) | 2015-09-28 | 2021-01-05 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| US10647703B2 (en) | 2015-09-28 | 2020-05-12 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| KR20180081596A (ko) | 2015-11-16 | 2018-07-16 | 아락세스 파마 엘엘씨 | 치환된 헤테로사이클릭 그룹을 포함하는 2-치환된 퀴나졸린 화합물 및 이의 사용 방법 |
| US10646488B2 (en) | 2016-07-13 | 2020-05-12 | Araxes Pharma Llc | Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof |
| US10280172B2 (en) | 2016-09-29 | 2019-05-07 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| WO2018140514A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(6-(3-hydroxynaphthalen-1-yl)quinazolin-2-yl)azetidin-1-yl)prop-2-en-1-one derivatives and similar compounds as kras g12c inhibitors for the treatment of cancer |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| WO2018140513A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer |
| CN110382482A (zh) | 2017-01-26 | 2019-10-25 | 亚瑞克西斯制药公司 | 稠合的杂-杂二环化合物及其使用方法 |
| EP3573954A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
| US11130740B2 (en) | 2017-04-25 | 2021-09-28 | Arbutus Biopharma Corporation | Substituted 2,3-dihydro-1H-indene analogs and methods using same |
| US11639346B2 (en) | 2017-05-25 | 2023-05-02 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant KRAS, HRAS or NRAS |
| JP2020521741A (ja) | 2017-05-25 | 2020-07-27 | アラクセス ファーマ エルエルシー | がんの処置のための化合物およびその使用の方法 |
| AU2018271990A1 (en) | 2017-05-25 | 2019-12-12 | Araxes Pharma Llc | Covalent inhibitors of KRAS |
| US12083118B2 (en) | 2018-03-29 | 2024-09-10 | Arbutus Biopharma Corporation | Substituted 1,1′-biphenyl compounds, analogues thereof, and methods using same |
| MX2021000887A (es) | 2018-08-01 | 2021-03-31 | Araxes Pharma Llc | Compuestos espiroheterociclicos y metodos de uso de los mismos para el tratamiento de cancer. |
| CN109485646A (zh) * | 2018-12-12 | 2019-03-19 | 中国药科大学 | 一种苯并噻唑醌类化合物及其制备方法和用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0210782A2 (en) * | 1985-07-19 | 1987-02-04 | Dainippon Pharmaceutical Co., Ltd. | Pyridine compounds, process for the preparation thereof and pharmaceutical composition containing the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8005133A (nl) * | 1980-09-12 | 1982-04-01 | Duphar Int Res | Fenylpiperazinederivaten met antiagressieve werking. |
| JPS57136518A (en) * | 1981-02-18 | 1982-08-23 | Eisai Co Ltd | Immunoregulator |
| EP0750496A1 (en) * | 1994-03-14 | 1997-01-02 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | Use of lipoxygenase inhibitors as anti-cancer therapeutic and intervention agents |
| DE19624659A1 (de) * | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalken- und Pyridylalkinsäureamide |
| DE19756236A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
-
1997
- 1997-12-17 DE DE19756236A patent/DE19756236A1/de not_active Ceased
-
1998
- 1998-12-08 ZA ZA9811235A patent/ZA9811235B/xx unknown
- 1998-12-16 AU AU20543/99A patent/AU2054399A/en not_active Abandoned
- 1998-12-16 DE DE69831877T patent/DE69831877T2/de not_active Expired - Lifetime
- 1998-12-16 JP JP2000538990A patent/JP4855576B2/ja not_active Expired - Fee Related
- 1998-12-16 EP EP98965275A patent/EP1060163B1/en not_active Expired - Lifetime
- 1998-12-16 AT AT98965275T patent/ATE306473T1/de active
- 1998-12-16 WO PCT/EP1998/008268 patent/WO1999031063A1/en not_active Ceased
- 1998-12-16 DK DK98965275T patent/DK1060163T3/da active
- 1998-12-16 ES ES98965275T patent/ES2251794T3/es not_active Expired - Lifetime
-
2011
- 2011-07-08 JP JP2011152041A patent/JP2011251976A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0210782A2 (en) * | 1985-07-19 | 1987-02-04 | Dainippon Pharmaceutical Co., Ltd. | Pyridine compounds, process for the preparation thereof and pharmaceutical composition containing the same |
Non-Patent Citations (1)
| Title |
|---|
| Joshisori Nishikawa u.a., Chem. Pharm. Bull. 37 (1989), S.100-105 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000007580A3 (en) * | 1998-08-03 | 2000-05-18 | Gene Kutato Kft N | Pharmaceutical compositions against autoimmune diseases |
| WO2003028728A1 (en) * | 2001-09-28 | 2003-04-10 | Richter Gedeon Vegyészeti Gyár Rt. | 4-(4-substituted piperazinyl-1yl)-butylcarboxamides as d3 dopamine subtype selective ligands |
| EP1348434A1 (en) * | 2002-03-27 | 2003-10-01 | Fujisawa Deutschland GmbH | Use of pyridyl amides as inhibitors of angiogenesis |
| WO2003080054A1 (en) * | 2002-03-27 | 2003-10-02 | Fujisawa Deutschland Gmbh | Use of pyridyl amides as inhibitors of angiogenesis |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1060163B1 (en) | 2005-10-12 |
| EP1060163A1 (en) | 2000-12-20 |
| JP2002508356A (ja) | 2002-03-19 |
| DK1060163T3 (da) | 2006-02-27 |
| AU2054399A (en) | 1999-07-05 |
| ZA9811235B (en) | 1999-06-08 |
| ES2251794T3 (es) | 2006-05-01 |
| WO1999031063A1 (en) | 1999-06-24 |
| JP4855576B2 (ja) | 2012-01-18 |
| ATE306473T1 (de) | 2005-10-15 |
| DE69831877T2 (de) | 2006-07-27 |
| DE69831877D1 (en) | 2006-02-23 |
| JP2011251976A (ja) | 2011-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8131 | Rejection |