TW200938202A - Heterocyclic compounds - Google Patents

Info

Publication number

TW200938202A

TW200938202A TW098103755A TW98103755A TW200938202A TW 200938202 A TW200938202 A TW 200938202A TW 098103755 A TW098103755 A TW 098103755A TW 98103755 A TW98103755 A TW 98103755A TW 200938202 A TW200938202 A TW 200938202A

Authority

TW

Taiwan

Prior art keywords

phenyl

pyrrolo

pyrimidin

amine

methyl

Prior art date

2008-02-06

Links

• Espacenet
• Global Dossier
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• 150000002391 heterocyclic compounds Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 815
• 238000000034 method Methods 0.000 claims abstract description 548
• 150000003839 salts Chemical class 0.000 claims abstract description 69
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
• 239000003814 drug Substances 0.000 claims abstract description 36
• 201000010099 disease Diseases 0.000 claims abstract description 32
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 13
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 13
• 230000001404 mediated effect Effects 0.000 claims abstract description 13
• 230000008569 process Effects 0.000 claims abstract description 10
• -1 cyclanealkyl Chemical group 0.000 claims description 292
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 191
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 186
• 150000001412 amines Chemical class 0.000 claims description 150
• 125000000217 alkyl group Chemical group 0.000 claims description 118
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 109
• 150000002576 ketones Chemical class 0.000 claims description 92
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
• 229910052739 hydrogen Inorganic materials 0.000 claims description 88
• 239000001257 hydrogen Substances 0.000 claims description 88
• 125000001424 substituent group Chemical group 0.000 claims description 78
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 74
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 48
• 239000007789 gas Substances 0.000 claims description 46
• 238000011282 treatment Methods 0.000 claims description 46
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 43
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 41
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
• 125000003545 alkoxy group Chemical group 0.000 claims description 40
• 125000003944 tolyl group Chemical group 0.000 claims description 40
• 125000000623 heterocyclic group Chemical group 0.000 claims description 36
• 229910052799 carbon Inorganic materials 0.000 claims description 35
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 28
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 28
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 28
• 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims description 27
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
• 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims description 26
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 25
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 25
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
• 239000000126 substance Substances 0.000 claims description 23
• 125000001153 fluoro group Chemical group F* 0.000 claims description 22
• 239000000203 mixture Substances 0.000 claims description 22
• 108090000623 proteins and genes Proteins 0.000 claims description 22
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 21
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 102000004169 proteins and genes Human genes 0.000 claims description 20
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 19
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 19
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 19
• 150000002923 oximes Chemical class 0.000 claims description 19
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 15
• 239000011737 fluorine Substances 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 150000002367 halogens Chemical group 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000000468 ketone group Chemical group 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 13
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 12
• 125000003277 amino group Chemical group 0.000 claims description 12
• XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 12
• 229960005181 morphine Drugs 0.000 claims description 12
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 230000036961 partial effect Effects 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 9
• HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 125000003107 substituted aryl group Chemical group 0.000 claims description 9
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
• JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims description 8
• 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims description 8
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
• 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
• 229910052786 argon Inorganic materials 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 125000001188 haloalkyl group Chemical group 0.000 claims description 8
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• 206010036790 Productive cough Diseases 0.000 claims description 7
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 7
• 125000004212 difluorophenyl group Chemical group 0.000 claims description 7
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 210000003802 sputum Anatomy 0.000 claims description 7
• 208000024794 sputum Diseases 0.000 claims description 7
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 7
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
• 229910000831 Steel Inorganic materials 0.000 claims description 6
• 230000002378 acidificating effect Effects 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 239000000463 material Substances 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 239000007921 spray Substances 0.000 claims description 6
• 239000010959 steel Substances 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 5
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 5
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
• 238000007125 Buchwald synthesis reaction Methods 0.000 claims description 5
• 241000989913 Gunnera petaloidea Species 0.000 claims description 5
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
• 125000001769 aryl amino group Chemical group 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 5
• 150000004032 porphyrins Chemical class 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
• 229910052707 ruthenium Inorganic materials 0.000 claims description 5
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
• 201000009030 Carcinoma Diseases 0.000 claims description 4
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 4
• 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 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 235000013336 milk Nutrition 0.000 claims description 4
• 239000008267 milk Substances 0.000 claims description 4
• 210000004080 milk Anatomy 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 4
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 238000003776 cleavage reaction Methods 0.000 claims description 3
• 125000006612 decyloxy group Chemical group 0.000 claims description 3
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 230000007017 scission Effects 0.000 claims description 3
• 239000011734 sodium Substances 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 239000002689 soil Substances 0.000 claims description 3
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
• WXTPOHDTGNYFSB-RMPHRYRLSA-N (2s,3r,4s,5s,6r)-2-(3,5-dihydroxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1 WXTPOHDTGNYFSB-RMPHRYRLSA-N 0.000 claims description 2
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
• RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims description 2
• DNTQTNXUBQIWFE-UHFFFAOYSA-N 1-sulfanylpiperazine Chemical compound SN1CCNCC1 DNTQTNXUBQIWFE-UHFFFAOYSA-N 0.000 claims description 2
• LMJDWRWZTXQWTI-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-indole Chemical compound C1CCC=C2NCCC21 LMJDWRWZTXQWTI-UHFFFAOYSA-N 0.000 claims description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 2
• WXTPOHDTGNYFSB-UHFFFAOYSA-N Phlorin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC(O)=C1 WXTPOHDTGNYFSB-UHFFFAOYSA-N 0.000 claims description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims description 2
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims description 2
• 230000000739 chaotic effect Effects 0.000 claims description 2
• 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 2
• 238000001035 drying Methods 0.000 claims description 2
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
• 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims 4
• 241001529936 Murinae Species 0.000 claims 2
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 2
• 150000003456 sulfonamides Chemical class 0.000 claims 2
• AEFBNJXWRHSZGO-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydropyrene Chemical compound C1=C2CCCC(CC3)C2=C2C3=CC=CC2=C1 AEFBNJXWRHSZGO-UHFFFAOYSA-N 0.000 claims 1
• UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 claims 1
• PGFIHORVILKHIA-UHFFFAOYSA-N 2-bromopyrimidine Chemical compound BrC1=NC=CC=N1 PGFIHORVILKHIA-UHFFFAOYSA-N 0.000 claims 1
• FDECURPHVMNAKO-UHFFFAOYSA-N 4-nonylaniline Chemical compound CCCCCCCCCC1=CC=C(N)C=C1 FDECURPHVMNAKO-UHFFFAOYSA-N 0.000 claims 1
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
• DERJTSBUJXPVDR-UHFFFAOYSA-N C1(CCNC2C1C1=CC3=CC=CC=C3N=C1CC2)=O Chemical compound C1(CCNC2C1C1=CC3=CC=CC=C3N=C1CC2)=O DERJTSBUJXPVDR-UHFFFAOYSA-N 0.000 claims 1
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