CA2698486A1 - Arylsulfonylaminomethylphosphonic acid derivatives, the preparation thereof and the use thereof as pharmaceutical compositions - Google Patents

Info

Publication number

CA2698486A1

CA2698486A1 CA2698486A CA2698486A CA2698486A1 CA 2698486 A1 CA2698486 A1 CA 2698486A1 CA 2698486 A CA2698486 A CA 2698486A CA 2698486 A CA2698486 A CA 2698486A CA 2698486 A1 CA2698486 A1 CA 2698486A1

Authority

CA

Canada

Prior art keywords

methyl

alkyl

amino

phenylsulphonyl

dichloro

Prior art date

2007-09-05

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000002253 acid Substances 0.000 title abstract description 13
• 238000002360 preparation method Methods 0.000 title description 16
• 239000008194 pharmaceutical composition Substances 0.000 title description 15
• 239000003814 drug Substances 0.000 claims abstract description 9
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 7
• -1 hydroxy, amino Chemical group 0.000 claims description 139
• 150000001875 compounds Chemical class 0.000 claims description 107
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 40
• 238000006243 chemical reaction Methods 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
• ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 239000000126 substance Substances 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
• 239000000460 chlorine Substances 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 13
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
• 229920001774 Perfluoroether Polymers 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000006239 protecting group Chemical group 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 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
• 125000001424 substituent group Chemical group 0.000 claims description 10
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 239000011737 fluorine Substances 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 239000000969 carrier Substances 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
• 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 5
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
• 238000001727 in vivo Methods 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• UIYUGNHEKIRGKS-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-[5-(methylcarbamoyl)naphthalen-2-yl]amino]methylphosphonic acid Chemical compound C=1C=C2C(C(=O)NC)=CC=CC2=CC=1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 UIYUGNHEKIRGKS-UHFFFAOYSA-N 0.000 claims description 4
• SOXNOPBBWFDOMY-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-naphthalen-2-ylamino]methylphosphonic acid Chemical compound C=1C=C2C=CC=CC2=CC=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 SOXNOPBBWFDOMY-UHFFFAOYSA-N 0.000 claims description 4
• MNWZTNAMMWIPMJ-UHFFFAOYSA-N [[5-(benzylcarbamoyl)naphthalen-2-yl]-(3,5-dichlorophenyl)sulfonylamino]methylphosphonic acid Chemical compound C=1C(Cl)=CC(Cl)=CC=1S(=O)(=O)N(CP(O)(=O)O)C(C=C1C=CC=2)=CC=C1C=2C(=O)NCC1=CC=CC=C1 MNWZTNAMMWIPMJ-UHFFFAOYSA-N 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 150000007522 mineralic acids Chemical class 0.000 claims description 4
• 150000007524 organic acids Chemical class 0.000 claims description 4
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 3
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
• 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 3
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 3
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 3
• AXFWFPONLKABGG-UHFFFAOYSA-N [(2-bromonaphthalen-1-yl)-(3,5-dichlorophenyl)sulfonylamino]methylphosphonic acid Chemical compound BrC=1C=CC2=CC=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 AXFWFPONLKABGG-UHFFFAOYSA-N 0.000 claims description 3
• IXYUJRNHYPRJRY-UHFFFAOYSA-N [(2-chloronaphthalen-1-yl)-(3,5-dichlorophenyl)sulfonylamino]methylphosphonic acid Chemical compound ClC=1C=CC2=CC=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 IXYUJRNHYPRJRY-UHFFFAOYSA-N 0.000 claims description 3
• GAQOLQPTJSOIOR-UHFFFAOYSA-N [(2-cyanonaphthalen-1-yl)-(3,5-dichlorophenyl)sulfonylamino]methylphosphonic acid Chemical compound N#CC=1C=CC2=CC=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 GAQOLQPTJSOIOR-UHFFFAOYSA-N 0.000 claims description 3
• MGLDBGNFWUIZQO-UHFFFAOYSA-N [(3,5-dibromophenyl)sulfonyl-naphthalen-1-ylamino]methylphosphonic acid Chemical compound C=1C=CC2=CC=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Br)=CC(Br)=C1 MGLDBGNFWUIZQO-UHFFFAOYSA-N 0.000 claims description 3
• BGTCJJWRBBPSAN-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(2-ethynylnaphthalen-1-yl)amino]methylphosphonic acid Chemical compound C#CC=1C=CC2=CC=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 BGTCJJWRBBPSAN-UHFFFAOYSA-N 0.000 claims description 3
• GOAHMFYCMPWEIU-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(2-methoxynaphthalen-1-yl)amino]methylphosphonic acid Chemical compound COC1=CC=C2C=CC=CC2=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 GOAHMFYCMPWEIU-UHFFFAOYSA-N 0.000 claims description 3
• ISVCSYCXBFWWOE-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(2-methylquinolin-8-yl)amino]methylphosphonic acid Chemical compound C12=NC(C)=CC=C2C=CC=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 ISVCSYCXBFWWOE-UHFFFAOYSA-N 0.000 claims description 3
• YUSLHURSTZFFKS-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(3-methylcinnolin-5-yl)amino]methylphosphonic acid Chemical compound C1=CC=C2N=NC(C)=CC2=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 YUSLHURSTZFFKS-UHFFFAOYSA-N 0.000 claims description 3
• HLYXLDPXCYQLSP-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(3-methylnaphthalen-2-yl)amino]methylphosphonic acid Chemical compound CC1=CC2=CC=CC=C2C=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 HLYXLDPXCYQLSP-UHFFFAOYSA-N 0.000 claims description 3
• XLTIZIRXKLNZKA-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(3-methylquinolin-5-yl)amino]methylphosphonic acid Chemical compound C12=CC(C)=CN=C2C=CC=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 XLTIZIRXKLNZKA-UHFFFAOYSA-N 0.000 claims description 3
• BGERLNNLQMVJTL-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(4-methoxynaphthalen-1-yl)amino]methylphosphonic acid Chemical compound C12=CC=CC=C2C(OC)=CC=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 BGERLNNLQMVJTL-UHFFFAOYSA-N 0.000 claims description 3
• ZTEUXACEVOWDKK-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(5-methoxynaphthalen-1-yl)amino]methylphosphonic acid Chemical compound C1=CC=C2C(OC)=CC=CC2=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 ZTEUXACEVOWDKK-UHFFFAOYSA-N 0.000 claims description 3
• NTXOBAKNKKVSIV-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(6-pyrimidin-2-ylnaphthalen-2-yl)amino]methylphosphonic acid Chemical compound C=1C(Cl)=CC(Cl)=CC=1S(=O)(=O)N(CP(O)(=O)O)C(C=C1C=C2)=CC=C1C=C2C1=NC=CC=N1 NTXOBAKNKKVSIV-UHFFFAOYSA-N 0.000 claims description 3
• JEJAMFJGBMCRGT-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-(7-methylquinolin-8-yl)amino]methylphosphonic acid Chemical compound CC1=CC=C2C=CC=NC2=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 JEJAMFJGBMCRGT-UHFFFAOYSA-N 0.000 claims description 3
• FXELBOZOUJLMIW-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-[4-(dimethylamino)quinazolin-8-yl]amino]methylphosphonic acid Chemical compound C1=CC=C2C(N(C)C)=NC=NC2=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 FXELBOZOUJLMIW-UHFFFAOYSA-N 0.000 claims description 3
• RQNCOYLVHUROPR-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-[5-(2-phenylethylcarbamoyl)naphthalen-1-yl]amino]methylphosphonic acid Chemical compound C=1C(Cl)=CC(Cl)=CC=1S(=O)(=O)N(CP(O)(=O)O)C(C1=CC=C2)=CC=CC1=C2C(=O)NCCC1=CC=CC=C1 RQNCOYLVHUROPR-UHFFFAOYSA-N 0.000 claims description 3
• FZVOXHYBRZUDSZ-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-[5-(dimethylsulfamoyl)naphthalen-1-yl]amino]methylphosphonic acid Chemical compound C1=CC=C2C(S(=O)(=O)N(C)C)=CC=CC2=C1N(CP(O)(O)=O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 FZVOXHYBRZUDSZ-UHFFFAOYSA-N 0.000 claims description 3
• QYPGMZKYQSZTPS-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-[5-(methylcarbamoyl)naphthalen-2-yl]amino]methyl-(2,2-dimethylpropanoyloxymethylperoxy)phosphinic acid Chemical compound C=1C=C2C(C(=O)NC)=CC=CC2=CC=1N(CP(O)(=O)OOCOC(=O)C(C)(C)C)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 QYPGMZKYQSZTPS-UHFFFAOYSA-N 0.000 claims description 3
• PMTVKKJYDQFNAE-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-[6-[(2-phenylacetyl)amino]naphthalen-2-yl]amino]methylphosphonic acid Chemical compound C=1C(Cl)=CC(Cl)=CC=1S(=O)(=O)N(CP(O)(=O)O)C(C=C1C=C2)=CC=C1C=C2NC(=O)CC1=CC=CC=C1 PMTVKKJYDQFNAE-UHFFFAOYSA-N 0.000 claims description 3
• CRRZQKAOKPWQLD-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-naphthalen-1-ylamino]methylphosphonic acid Chemical compound C=1C=CC2=CC=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 CRRZQKAOKPWQLD-UHFFFAOYSA-N 0.000 claims description 3
• QRQPRMRYMHTGHE-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-quinazolin-8-ylamino]methylphosphonic acid Chemical compound C=1C=CC2=CN=CN=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 QRQPRMRYMHTGHE-UHFFFAOYSA-N 0.000 claims description 3
• DITDURCBHHLOAK-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-quinolin-3-ylamino]methylphosphonic acid Chemical compound C=1N=C2C=CC=CC2=CC=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 DITDURCBHHLOAK-UHFFFAOYSA-N 0.000 claims description 3
• GGKYYPROBCRRGZ-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-quinolin-5-ylamino]methylphosphonic acid Chemical compound C=1C=CC2=NC=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 GGKYYPROBCRRGZ-UHFFFAOYSA-N 0.000 claims description 3
• CZEKNPZDXASHMG-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-quinolin-6-ylamino]methylphosphonic acid Chemical compound C=1C=C2N=CC=CC2=CC=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 CZEKNPZDXASHMG-UHFFFAOYSA-N 0.000 claims description 3
• SZOAXTFCOABKDQ-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-quinolin-7-ylamino]methylphosphonic acid Chemical compound C=1C=C2C=CC=NC2=CC=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 SZOAXTFCOABKDQ-UHFFFAOYSA-N 0.000 claims description 3
• UPEWGINAZOKEGZ-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-quinolin-8-ylamino]methylphosphonic acid Chemical compound C=1C=CC2=CC=CN=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 UPEWGINAZOKEGZ-UHFFFAOYSA-N 0.000 claims description 3
• CLAVFXVMJIHCSP-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-quinoxalin-5-ylamino]methylphosphonic acid Chemical compound C=1C=CC2=NC=CN=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 CLAVFXVMJIHCSP-UHFFFAOYSA-N 0.000 claims description 3
• QKCLTQMWGIRKPU-UHFFFAOYSA-N [(3,5-dichlorophenyl)sulfonyl-quinoxalin-6-ylamino]methylphosphonic acid Chemical compound C=1C=C2N=CC=NC2=CC=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 QKCLTQMWGIRKPU-UHFFFAOYSA-N 0.000 claims description 3
• YALORNPPFJVROW-UHFFFAOYSA-N [(3-bromo-5-chlorophenyl)sulfonyl-naphthalen-1-ylamino]methylphosphonic acid Chemical compound C=1C=CC2=CC=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Br)=C1 YALORNPPFJVROW-UHFFFAOYSA-N 0.000 claims description 3
• VKUAXWFNKKUZCQ-UHFFFAOYSA-N [(3-bromo-5-methylphenyl)sulfonyl-naphthalen-1-ylamino]methylphosphonic acid Chemical compound CC1=CC(Br)=CC(S(=O)(=O)N(CP(O)(O)=O)C=2C3=CC=CC=C3C=CC=2)=C1 VKUAXWFNKKUZCQ-UHFFFAOYSA-N 0.000 claims description 3
• CAWZAHALFAPXFF-UHFFFAOYSA-N [(3-chloro-5-methylphenyl)sulfonyl-naphthalen-1-ylamino]methylphosphonic acid Chemical compound CC1=CC(Cl)=CC(S(=O)(=O)N(CP(O)(O)=O)C=2C3=CC=CC=C3C=CC=2)=C1 CAWZAHALFAPXFF-UHFFFAOYSA-N 0.000 claims description 3
• PVRNWAMPSVSZKW-UHFFFAOYSA-N [(5-cyanonaphthalen-1-yl)-(3,5-dichlorophenyl)sulfonylamino]methylphosphonic acid Chemical compound C=1C=CC2=C(C#N)C=CC=C2C=1N(CP(O)(=O)O)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 PVRNWAMPSVSZKW-UHFFFAOYSA-N 0.000 claims description 3
• PZQCNOWFKVNALR-UHFFFAOYSA-N [[(3,5-dichlorophenyl)sulfonyl-quinolin-6-ylamino]methyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate Chemical compound C=1C=C2N=CC=CC2=CC=1N(CP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 PZQCNOWFKVNALR-UHFFFAOYSA-N 0.000 claims description 3
• PFFCIMWBNNAUGS-UHFFFAOYSA-N [[2-(benzylcarbamoyl)naphthalen-1-yl]-(3,5-dichlorophenyl)sulfonylamino]methylphosphonic acid Chemical compound C=1C(Cl)=CC(Cl)=CC=1S(=O)(=O)N(CP(O)(=O)O)C(C1=CC=CC=C1C=C1)=C1C(=O)NCC1=CC=CC=C1 PFFCIMWBNNAUGS-UHFFFAOYSA-N 0.000 claims description 3
• GWVODDYSBPISCN-UHFFFAOYSA-N [[5-(benzylcarbamoyl)naphthalen-1-yl]-(3,5-dichlorophenyl)sulfonylamino]methylphosphonic acid Chemical compound C=1C(Cl)=CC(Cl)=CC=1S(=O)(=O)N(CP(O)(=O)O)C(C1=CC=C2)=CC=CC1=C2C(=O)NCC1=CC=CC=C1 GWVODDYSBPISCN-UHFFFAOYSA-N 0.000 claims description 3
• GLHGDGAJHDGATA-UHFFFAOYSA-N [[5-[benzyl(methyl)carbamoyl]naphthalen-1-yl]-(3,5-dichlorophenyl)sulfonylamino]methylphosphonic acid Chemical compound C=1C=CC2=C(N(CP(O)(O)=O)S(=O)(=O)C=3C=C(Cl)C=C(Cl)C=3)C=CC=C2C=1C(=O)N(C)CC1=CC=CC=C1 GLHGDGAJHDGATA-UHFFFAOYSA-N 0.000 claims description 3
• 235000005985 organic acids Nutrition 0.000 claims description 3
• LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 3
• CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 3
• BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 claims description 3
• JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 claims description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
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• XABYCTJRTCHRAO-UHFFFAOYSA-N [[(3,5-dichlorophenyl)sulfonyl-[5-(methylcarbamoyl)naphthalen-2-yl]amino]methyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate Chemical compound C=1C=C2C(C(=O)NC)=CC=CC2=CC=1N(CP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 XABYCTJRTCHRAO-UHFFFAOYSA-N 0.000 claims description 2
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