TWI725004B - 4,6-經取代之吡唑并［1,5-ａ］吡 - Google Patents

Info

Publication number

TWI725004B

TWI725004B TW104140878A TW104140878A TWI725004B TW I725004 B TWI725004 B TW I725004B TW 104140878 A TW104140878 A TW 104140878A TW 104140878 A TW104140878 A TW 104140878A TW I725004 B TWI725004 B TW I725004B

Authority

TW

Taiwan

Prior art keywords

pyrazol

pyridine

pyrazolo

pent

alkyl

Prior art date

2014-12-05

Links

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• Global Dossier
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• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 279
• 150000003839 salts Chemical class 0.000 claims abstract description 120
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 25
• 210000000056 organ Anatomy 0.000 claims abstract description 18
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 17
• 239000003112 inhibitor Substances 0.000 claims abstract description 17
• 102000042838 JAK family Human genes 0.000 claims abstract description 6
• 108091082332 JAK family Proteins 0.000 claims abstract description 6
• -1 cyclopropylidene Chemical group 0.000 claims description 437
• 125000000217 alkyl group Chemical group 0.000 claims description 431
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 207
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 98
• 238000000034 method Methods 0.000 claims description 92
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 75
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 74
• 201000010099 disease Diseases 0.000 claims description 67
• 125000003545 alkoxy group Chemical group 0.000 claims description 66
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 63
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 59
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 54
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
• 239000008194 pharmaceutical composition Substances 0.000 claims description 49
• 229910052757 nitrogen Inorganic materials 0.000 claims description 48
• 238000002360 preparation method Methods 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 125000001424 substituent group Chemical group 0.000 claims description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 36
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 32
• 239000003814 drug Substances 0.000 claims description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
• 210000004027 cell Anatomy 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 25
• 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 23
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 238000006243 chemical reaction Methods 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 239000002585 base Substances 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 229940124597 therapeutic agent Drugs 0.000 claims description 18
• 210000001519 tissue Anatomy 0.000 claims description 17
• 239000004146 Propane-1,2-diol Substances 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 235000013772 propylene glycol Nutrition 0.000 claims description 16
• 229960004063 propylene glycol Drugs 0.000 claims description 16
• 206010052779 Transplant rejections Diseases 0.000 claims description 14
• YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• MFNYBOWJWGPXFM-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1CCC1 MFNYBOWJWGPXFM-UHFFFAOYSA-N 0.000 claims description 12
• 206010025135 lupus erythematosus Diseases 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 208000024891 symptom Diseases 0.000 claims description 10
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 9
• 125000005228 aryl sulfonate group Chemical group 0.000 claims description 9
• 125000002393 azetidinyl group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims description 8
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical group CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 7
• 108010036949 Cyclosporine Proteins 0.000 claims description 7
• 125000005227 alkyl sulfonate group Chemical group 0.000 claims description 7
• 230000003211 malignant effect Effects 0.000 claims description 7
• HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 claims description 7
• 230000019491 signal transduction Effects 0.000 claims description 7
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• 239000003153 chemical reaction reagent Substances 0.000 claims description 6
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 6
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
• 208000004232 Enteritis Diseases 0.000 claims description 5
• 239000004593 Epoxy Substances 0.000 claims description 5
• 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 claims description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 5
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000004980 cyclopropylene group Chemical group 0.000 claims description 5
• 230000000694 effects Effects 0.000 claims description 5
• HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 claims description 5
• 208000017520 skin disease Diseases 0.000 claims description 5
• 230000008685 targeting Effects 0.000 claims description 5
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
• 206010020751 Hypersensitivity Diseases 0.000 claims description 4
• CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• 238000011374 additional therapy Methods 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
• XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 229960002009 naproxen Drugs 0.000 claims description 4
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 4
• 229960002702 piroxicam Drugs 0.000 claims description 4
• 108090000623 proteins and genes Proteins 0.000 claims description 4
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 4
• 108020004491 Antisense DNA Proteins 0.000 claims description 3
• 108020005544 Antisense RNA Proteins 0.000 claims description 3
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 3
• 229940123587 Cell cycle inhibitor Drugs 0.000 claims description 3
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
• 229930105110 Cyclosporin A Natural products 0.000 claims description 3
• 208000002249 Diabetes Complications Diseases 0.000 claims description 3
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 3
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 3
• 229940079156 Proteasome inhibitor Drugs 0.000 claims description 3
• QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 3
• 229960003697 abatacept Drugs 0.000 claims description 3
• 229960001138 acetylsalicylic acid Drugs 0.000 claims description 3
• 239000002168 alkylating agent Substances 0.000 claims description 3
• 229940100198 alkylating agent Drugs 0.000 claims description 3
• 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 3
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 3
• 239000003242 anti bacterial agent Substances 0.000 claims description 3
• 230000002280 anti-androgenic effect Effects 0.000 claims description 3
• 230000003388 anti-hormonal effect Effects 0.000 claims description 3
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
• 230000000340 anti-metabolite Effects 0.000 claims description 3
• 239000000051 antiandrogen Substances 0.000 claims description 3
• 229940088710 antibiotic agent Drugs 0.000 claims description 3
• 229940100197 antimetabolite Drugs 0.000 claims description 3
• 239000002256 antimetabolite Substances 0.000 claims description 3
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• 229960001265 ciclosporin Drugs 0.000 claims description 3
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• 239000000824 cytostatic agent Substances 0.000 claims description 3
• 230000001085 cytostatic effect Effects 0.000 claims description 3
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• 238000010790 dilution Methods 0.000 claims description 3
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• 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 3
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• 239000003102 growth factor Substances 0.000 claims description 3
• 229960004171 hydroxychloroquine Drugs 0.000 claims description 3
• XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 claims description 3
• 229960001680 ibuprofen Drugs 0.000 claims description 3
• 239000000367 immunologic factor Substances 0.000 claims description 3
• 238000000338 in vitro Methods 0.000 claims description 3
• 238000003780 insertion Methods 0.000 claims description 3
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• 229960000681 leflunomide Drugs 0.000 claims description 3
• VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 claims description 3
• 210000004962 mammalian cell Anatomy 0.000 claims description 3
• 229960003105 metformin Drugs 0.000 claims description 3
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 3
• 229960000485 methotrexate Drugs 0.000 claims description 3
• 229960000951 mycophenolic acid Drugs 0.000 claims description 3
• 239000007800 oxidant agent Substances 0.000 claims description 3
• 229910052763 palladium Inorganic materials 0.000 claims description 3
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 239000003207 proteasome inhibitor Substances 0.000 claims description 3
• 102000004169 proteins and genes Human genes 0.000 claims description 3
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 3
• 208000023504 respiratory system disease Diseases 0.000 claims description 3
• 102000027483 retinoid hormone receptors Human genes 0.000 claims description 3
• 108091008679 retinoid hormone receptors Proteins 0.000 claims description 3
• 229960002930 sirolimus Drugs 0.000 claims description 3
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 3
• 150000003431 steroids Chemical class 0.000 claims description 3
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• 229940044693 topoisomerase inhibitor Drugs 0.000 claims description 3
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• 239000002451 tumor necrosis factor inhibitor Substances 0.000 claims description 3
• 206010012655 Diabetic complications Diseases 0.000 claims description 2
• 206010016654 Fibrosis Diseases 0.000 claims description 2
• 201000005569 Gout Diseases 0.000 claims description 2
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
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• 206010033661 Pancytopenia Diseases 0.000 claims description 2
• 206010037660 Pyrexia Diseases 0.000 claims description 2
• 206010040047 Sepsis Diseases 0.000 claims description 2
• 208000006045 Spondylarthropathies Diseases 0.000 claims description 2
• 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims description 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
• 125000005907 alkyl ester group Chemical class 0.000 claims description 2
• 229910021529 ammonia Inorganic materials 0.000 claims description 2
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 239000003795 chemical substances by application Substances 0.000 claims description 2
• 150000001924 cycloalkanes Chemical class 0.000 claims description 2
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 2
• 230000004761 fibrosis Effects 0.000 claims description 2
• 125000001072 heteroaryl group Chemical group 0.000 claims description 2
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• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 2
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• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
• WDBQDZRKKFDOQF-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=C=C[N]N21 WDBQDZRKKFDOQF-UHFFFAOYSA-N 0.000 claims 37
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• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 4
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• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
• 239000004358 Butane-1, 3-diol Substances 0.000 claims 2
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• 229940014456 mycophenolate Drugs 0.000 claims 2
• AKDQIPLNCVYFPR-UHFFFAOYSA-N propane-1,2-diol hydrochloride Chemical compound Cl.CC(O)CO.CC(O)CO AKDQIPLNCVYFPR-UHFFFAOYSA-N 0.000 claims 2
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
• 241000009298 Trigla lyra Species 0.000 claims 1
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• WEMTXCOQGNENQZ-UHFFFAOYSA-N cyclobutanethiol Chemical compound SC1CCC1 WEMTXCOQGNENQZ-UHFFFAOYSA-N 0.000 claims 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
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• 208000030533 eye disease Diseases 0.000 claims 1
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