DE19756236A1 - Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide - Google Patents

Info

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

1997-12-17

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

• Espacenet
• Global Dossier
• DPMA
• Discuss

• 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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