TW200808321A - Certain chemical entities, compositions and methods - Google Patents

Info

Publication number

TW200808321A

TW200808321A TW095146918A TW95146918A TW200808321A TW 200808321 A TW200808321 A TW 200808321A TW 095146918 A TW095146918 A TW 095146918A TW 95146918 A TW95146918 A TW 95146918A TW 200808321 A TW200808321 A TW 200808321A

Authority

TW

Taiwan

Prior art keywords

methyl

amino

phenyl

fluoro

optionally substituted

Prior art date

2005-12-15

Links

• Espacenet
• Global Dossier
• Discuss

• 239000000203 mixture Substances 0.000 title claims description 95
• 238000000034 method Methods 0.000 title claims description 47
• 150000005829 chemical entities Chemical class 0.000 title 1
• 206010019280 Heart failures Diseases 0.000 claims abstract description 26
• 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 20
• 238000011282 treatment Methods 0.000 claims abstract description 18
• 230000000747 cardiac effect Effects 0.000 claims abstract description 11
• 208000008253 Systolic Heart Failure Diseases 0.000 claims abstract 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 729
• -1 cyano, hydroxy Chemical group 0.000 claims description 708
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 519
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 209
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 197
• 125000000217 alkyl group Chemical group 0.000 claims description 171
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 163
• 229910052739 hydrogen Inorganic materials 0.000 claims description 133
• 239000001257 hydrogen Substances 0.000 claims description 133
• 125000001072 heteroaryl group Chemical group 0.000 claims description 86
• 150000001875 compounds Chemical class 0.000 claims description 85
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 84
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
• 239000002253 acid Substances 0.000 claims description 68
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 65
• 239000000126 substance Substances 0.000 claims description 61
• 125000004076 pyridyl group Chemical group 0.000 claims description 59
• 125000003386 piperidinyl group Chemical group 0.000 claims description 55
• 125000001041 indolyl group Chemical group 0.000 claims description 54
• TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 54
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 52
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 51
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 48
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 48
• 125000001153 fluoro group Chemical group F* 0.000 claims description 47
• 125000005843 halogen group Chemical group 0.000 claims description 47
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 43
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 42
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 41
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 41
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 41
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 40
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 39
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 150000001412 amines Chemical class 0.000 claims description 34
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 34
• 210000002216 heart Anatomy 0.000 claims description 33
• 150000004702 methyl esters Chemical class 0.000 claims description 31
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 31
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 30
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 30
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 29
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 28
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 27
• 239000004202 carbamide Substances 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
• 125000003107 substituted aryl group Chemical group 0.000 claims description 25
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 24
• 125000003277 amino group Chemical group 0.000 claims description 24
• 235000013877 carbamide Nutrition 0.000 claims description 22
• 239000007789 gas Substances 0.000 claims description 22
• 239000000052 vinegar Substances 0.000 claims description 22
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• YKFLJYAKACCWMH-UHFFFAOYSA-N methyl piperidine-1-carboxylate Chemical compound COC(=O)N1CCCCC1 YKFLJYAKACCWMH-UHFFFAOYSA-N 0.000 claims description 21
• 235000021419 vinegar Nutrition 0.000 claims description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 20
• 125000005842 heteroatom Chemical group 0.000 claims description 19
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 19
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 18
• 235000019253 formic acid Nutrition 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 18
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
• 229930182817 methionine Natural products 0.000 claims description 15
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 14
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 208000019622 heart disease Diseases 0.000 claims description 14
• 230000001965 increasing effect Effects 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 13
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 12
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 12
• 229940079593 drug Drugs 0.000 claims description 12
• 125000004494 ethyl ester group Chemical group 0.000 claims description 12
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 12
• 230000008602 contraction Effects 0.000 claims description 11
• 239000002689 soil Substances 0.000 claims description 11
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 11
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 10
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 9
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
• 229910052786 argon Inorganic materials 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 8
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 8
• 150000002923 oximes Chemical class 0.000 claims description 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 7
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 7
• 241000009298 Trigla lyra Species 0.000 claims description 7
• 230000010247 heart contraction Effects 0.000 claims description 7
• 229960003194 meglumine Drugs 0.000 claims description 7
• RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
• YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 239000000651 prodrug Substances 0.000 claims description 6
• 229940002612 prodrug Drugs 0.000 claims description 6
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
• ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 5
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 5
• 239000002243 precursor Substances 0.000 claims description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
• 241001465754 Metazoa Species 0.000 claims description 4
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
• 230000008901 benefit Effects 0.000 claims description 4
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 4
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 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
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 3
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
• 239000000443 aerosol Substances 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 239000006013 carbendazim Substances 0.000 claims description 3
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
• 229940102396 methyl bromide Drugs 0.000 claims description 3
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 3
• 239000006187 pill Substances 0.000 claims description 3
• 229930192474 thiophene Natural products 0.000 claims description 3
• 230000009278 visceral effect Effects 0.000 claims description 3
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
• HVSACIINGLQLCS-UHFFFAOYSA-N 2-methoxyethyl formate Chemical compound COCCOC=O HVSACIINGLQLCS-UHFFFAOYSA-N 0.000 claims description 2
• XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 claims description 2
• QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 claims description 2
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
• WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 claims description 2
• LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 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
• 239000012530 fluid Substances 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 239000007937 lozenge Substances 0.000 claims description 2
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
• XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 2
• 235000019260 propionic acid Nutrition 0.000 claims description 2
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 22
• BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims 4
• 125000005577 anthracene group Chemical group 0.000 claims 2
• GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 2
• CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims 2
• SARMGXPVOFNNNG-UHFFFAOYSA-N 1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine;hydron;chloride Chemical group Cl.CC(C)N=C(N)N=C(N)NC1=CC=C(Cl)C=C1 SARMGXPVOFNNNG-UHFFFAOYSA-N 0.000 claims 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
• UKQJDWBNQNAJHB-UHFFFAOYSA-N 2-hydroxyethyl formate Chemical compound OCCOC=O UKQJDWBNQNAJHB-UHFFFAOYSA-N 0.000 claims 1
• YVDQSNMOVRWOSU-UHFFFAOYSA-N 2-hydroxyethyl piperidine-1-carboxylate Chemical compound OCCOC(=O)N1CCCCC1 YVDQSNMOVRWOSU-UHFFFAOYSA-N 0.000 claims 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
• YSIKHBWUBSFBRZ-UHFFFAOYSA-N 3-methoxypropanoic acid Chemical compound COCCC(O)=O YSIKHBWUBSFBRZ-UHFFFAOYSA-N 0.000 claims 1
• VUTBELPREDJDDH-UHFFFAOYSA-N 4-amino-5-hydroxymethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CO)C(N)=N1 VUTBELPREDJDDH-UHFFFAOYSA-N 0.000 claims 1
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
• RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 claims 1
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
• 241000207929 Scutellaria Species 0.000 claims 1
• 239000002671 adjuvant Substances 0.000 claims 1
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• RDJGWRFTDZZXSM-RNWLQCGYSA-N benzylmorphine Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=C[C@@H]1O)C)C1=C2C4=CC=C1OCC1=CC=CC=C1 RDJGWRFTDZZXSM-RNWLQCGYSA-N 0.000 claims 1
• 229910021386 carbon form Inorganic materials 0.000 claims 1
• 238000005266 casting Methods 0.000 claims 1
• 239000006071 cream Substances 0.000 claims 1
• 239000007933 dermal patch Substances 0.000 claims 1
• RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 claims 1
• 239000012535 impurity Substances 0.000 claims 1
• GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 1
• 229960003105 metformin Drugs 0.000 claims 1
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 1
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims 1
• VTHOTOFWYDBNID-UHFFFAOYSA-N n-decylaniline Chemical compound CCCCCCCCCCNC1=CC=CC=C1 VTHOTOFWYDBNID-UHFFFAOYSA-N 0.000 claims 1
• IKVDMBQGHZVMRN-UHFFFAOYSA-N n-methyldecan-1-amine Chemical compound CCCCCCCCCCNC IKVDMBQGHZVMRN-UHFFFAOYSA-N 0.000 claims 1
• ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims 1
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