TWI426908B - 特定化學品、組成物及方法 - Google Patents

Info

Publication number

TWI426908B

TWI426908B TW097130926A TW97130926A TWI426908B TW I426908 B TWI426908 B TW I426908B TW 097130926 A TW097130926 A TW 097130926A TW 97130926 A TW97130926 A TW 97130926A TW I426908 B TWI426908 B TW I426908B

Authority

TW

Taiwan

Prior art keywords

methyl

amino

chloro

fluorophenyl

isoquinolinyl

Prior art date

2007-08-15

Links

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• 239000000203 mixture Substances 0.000 title claims description 160
• 239000000126 substance Substances 0.000 title claims description 68
• 238000000034 method Methods 0.000 title description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 783
• -1 pyrido[3,4-d]pyridinyl Chemical group 0.000 claims description 747
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 517
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 278
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 143
• 125000000217 alkyl group Chemical group 0.000 claims description 131
• 150000001875 compounds Chemical class 0.000 claims description 110
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 102
• 239000001257 hydrogen Substances 0.000 claims description 97
• 229910052739 hydrogen Inorganic materials 0.000 claims description 97
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 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 84
• 125000001072 heteroaryl group Chemical group 0.000 claims description 82
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 75
• 150000001412 amines Chemical class 0.000 claims description 70
• 102000003505 Myosin Human genes 0.000 claims description 67
• 108060008487 Myosin Proteins 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 66
• 229910052760 oxygen Inorganic materials 0.000 claims description 56
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 55
• 150000002148 esters Chemical class 0.000 claims description 45
• 125000005843 halogen group Chemical group 0.000 claims description 45
• 150000002431 hydrogen Chemical class 0.000 claims description 41
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 37
• 210000002460 smooth muscle Anatomy 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 35
• 125000005842 heteroatom Chemical group 0.000 claims description 34
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 33
• NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 32
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 32
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 28
• 239000001301 oxygen Substances 0.000 claims description 27
• 125000003107 substituted aryl group Chemical group 0.000 claims description 27
• 239000002253 acid Substances 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 23
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 23
• 239000000460 chlorine Substances 0.000 claims description 22
• NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 claims description 21
• 210000003205 muscle Anatomy 0.000 claims description 21
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
• 125000003277 amino group Chemical group 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
• 239000000725 suspension Substances 0.000 claims description 19
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 18
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 claims description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 15
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 14
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 13
• 241000009298 Trigla lyra Species 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 125000004494 ethyl ester group Chemical group 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 12
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 12
• 239000011737 fluorine Substances 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims description 11
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 11
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 10
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 10
• VYCKDIRCVDCQAE-UHFFFAOYSA-N isoquinolin-3-amine Chemical compound C1=CC=C2C=NC(N)=CC2=C1 VYCKDIRCVDCQAE-UHFFFAOYSA-N 0.000 claims description 10
• 229910052721 tungsten Inorganic materials 0.000 claims description 10
• WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 9
• 206010020772 Hypertension Diseases 0.000 claims description 9
• 125000005605 benzo group Chemical group 0.000 claims description 9
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
• ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 9
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 9
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
• 150000003857 carboxamides Chemical class 0.000 claims description 8
• HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
• 239000007788 liquid Substances 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000005493 quinolyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims description 6
• 229960002195 perazine Drugs 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
• 208000010412 Glaucoma Diseases 0.000 claims description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
• 125000004104 aryloxy group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 5
• 230000004064 dysfunction Effects 0.000 claims description 5
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 5
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 4
• XCHFNEFLOKPNOX-UHFFFAOYSA-N 1-methoxy-1,2,2-trimethylhydrazine Chemical compound CON(C)N(C)C XCHFNEFLOKPNOX-UHFFFAOYSA-N 0.000 claims description 4
• ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 claims description 4
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
• 206010006482 Bronchospasm Diseases 0.000 claims description 4
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
• 206010021639 Incontinence Diseases 0.000 claims description 4
• 208000008081 Intestinal Fistula Diseases 0.000 claims description 4
• 208000006011 Stroke Diseases 0.000 claims description 4
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
• 239000000443 aerosol Substances 0.000 claims description 4
• IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 4
• 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
• 229930182817 methionine Natural products 0.000 claims description 4
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 claims description 4
• 229960004448 pentamidine Drugs 0.000 claims description 4
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 4
• 239000000843 powder Substances 0.000 claims description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 4
• 238000007634 remodeling Methods 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 3
• SETHSKIRVBKZTB-UHFFFAOYSA-N NC([O])=O Chemical compound NC([O])=O SETHSKIRVBKZTB-UHFFFAOYSA-N 0.000 claims description 3
• 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 3
• 206010036600 Premature labour Diseases 0.000 claims description 3
• 208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 230000007885 bronchoconstriction Effects 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 3
• 201000001881 impotence Diseases 0.000 claims description 3
• 150000004702 methyl esters Chemical class 0.000 claims description 3
• 230000004899 motility Effects 0.000 claims description 3
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 3
• 208000026440 premature labor Diseases 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 2
• 125000002252 acyl group Chemical group 0.000 claims description 2
• 125000003943 azolyl group Chemical group 0.000 claims description 2
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
• 239000002775 capsule Substances 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000002720 diazolyl group Chemical group 0.000 claims description 2
• 238000005984 hydrogenation reaction Methods 0.000 claims description 2
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
• 125000005496 phosphonium group Chemical group 0.000 claims description 2
• 239000000829 suppository Substances 0.000 claims description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
• 238000012800 visualization Methods 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 44
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 27
• ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 claims 24
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 10
• FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
• UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 claims 9
• KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 claims 8
• RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 claims 8
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 7
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 7
• 125000001207 fluorophenyl group Chemical group 0.000 claims 7
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 6
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims 5
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 4
• NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 claims 4
• ZCJAYDKWZAWMPR-UHFFFAOYSA-N 1-chloro-2-fluorobenzene Chemical compound FC1=CC=CC=C1Cl ZCJAYDKWZAWMPR-UHFFFAOYSA-N 0.000 claims 3
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 3
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 3
• 239000004202 carbamide Substances 0.000 claims 3
• 235000013877 carbamide Nutrition 0.000 claims 3
• 235000019260 propionic acid Nutrition 0.000 claims 3
• RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims 3
• KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 claims 2
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
• RDUHFHDKXQBHMH-UHFFFAOYSA-N 2-benzyl-3-hydroxypropanoic acid Chemical compound OCC(C(O)=O)CC1=CC=CC=C1 RDUHFHDKXQBHMH-UHFFFAOYSA-N 0.000 claims 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims 2
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