JP2001521532A - 置換されたフエニル誘導体、その製造方法及びその使用方法 - Google Patents
置換されたフエニル誘導体、その製造方法及びその使用方法Info
- Publication number
- JP2001521532A JP2001521532A JP54475998A JP54475998A JP2001521532A JP 2001521532 A JP2001521532 A JP 2001521532A JP 54475998 A JP54475998 A JP 54475998A JP 54475998 A JP54475998 A JP 54475998A JP 2001521532 A JP2001521532 A JP 2001521532A
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethylphenyl
- tetrazolyl
- phenylurea
- hydroxy
- alkyl
- Prior art date
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- -1 cyano, nitro, amino Chemical group 0.000 claims abstract description 120
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 208000007056 sickle cell anemia Diseases 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 5
- 239000004305 biphenyl Substances 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims abstract description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 238000001727 in vivo Methods 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000524 functional group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000006267 biphenyl group Chemical group 0.000 claims abstract 3
- 125000004122 cyclic group Chemical group 0.000 claims abstract 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 20
- 108010062745 Chloride Channels Proteins 0.000 claims description 19
- 102000011045 Chloride Channels Human genes 0.000 claims description 19
- 208000035475 disorder Diseases 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 13
- 208000010412 Glaucoma Diseases 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 206010048962 Brain oedema Diseases 0.000 claims description 10
- 108091006146 Channels Proteins 0.000 claims description 10
- 206010020772 Hypertension Diseases 0.000 claims description 10
- 208000001132 Osteoporosis Diseases 0.000 claims description 10
- 208000004880 Polyuria Diseases 0.000 claims description 10
- 208000006752 brain edema Diseases 0.000 claims description 10
- 230000035619 diuresis Effects 0.000 claims description 10
- 208000028867 ischemia Diseases 0.000 claims description 10
- 206010012735 Diarrhoea Diseases 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 210000002700 urine Anatomy 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 230000004968 inflammatory condition Effects 0.000 claims description 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- VGFPBFXHVIOYJA-UHFFFAOYSA-N 1-(3-acetylphenyl)-1-[2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound CC(=O)C1=CC=CC(N(C(N)=O)C=2C(=CC=CC=2)C=2NN=NN=2)=C1 VGFPBFXHVIOYJA-UHFFFAOYSA-N 0.000 claims description 3
- KVBDPDPKYDLTJA-UHFFFAOYSA-N 1-(3-bromophenyl)-1-[4-bromo-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C=1C=C(Br)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(Br)=C1 KVBDPDPKYDLTJA-UHFFFAOYSA-N 0.000 claims description 3
- SYVZTFRUMHJQIR-UHFFFAOYSA-N 1-[2-(4-hydroxy-1,2,4-triazol-3-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC=C(C=2N(C=NN=2)O)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 SYVZTFRUMHJQIR-UHFFFAOYSA-N 0.000 claims description 3
- JFGXFYKXRPMSJT-UHFFFAOYSA-N 1-[4-bromo-2-(2h-tetrazol-5-yl)phenyl]-1-(3-pyridin-3-ylphenyl)urea Chemical compound C=1C=C(Br)C=C(C=2NN=NN=2)C=1N(C(=O)N)C(C=1)=CC=CC=1C1=CC=CN=C1 JFGXFYKXRPMSJT-UHFFFAOYSA-N 0.000 claims description 3
- FFCHMMOMHWKHMU-UHFFFAOYSA-N 1-[4-nitro-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C([N+]([O-])=O)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 FFCHMMOMHWKHMU-UHFFFAOYSA-N 0.000 claims description 3
- GAHLXGAQEUNMBN-UHFFFAOYSA-N 4-[4-[n-carbamoyl-3-(trifluoromethyl)anilino]-3-(2h-tetrazol-5-yl)phenyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1N(C(N)=O)C1=CC=CC(C(F)(F)F)=C1 GAHLXGAQEUNMBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- ZSRNFXQWCQXPSR-UHFFFAOYSA-N [4-(2-phenylphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(C=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1C1=NN=NN1 ZSRNFXQWCQXPSR-UHFFFAOYSA-N 0.000 claims description 3
- NYFSCMAKKWTJAH-UHFFFAOYSA-N [4-bromo-3-(2-phenylphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound N=1N=NNC=1C=1C(NC(=O)N)=CC=C(Br)C=1C1=CC=CC=C1C1=CC=CC=C1 NYFSCMAKKWTJAH-UHFFFAOYSA-N 0.000 claims description 3
- GLQRNQRAFLONQC-UHFFFAOYSA-N [5-(2,3-dihydro-1h-inden-1-yl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound NC(=O)NC1=CC(C2C3=CC=CC=C3CC2)=CC=C1C1=NN=NN1 GLQRNQRAFLONQC-UHFFFAOYSA-N 0.000 claims description 3
- 230000007815 allergy Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 230000000172 allergic effect Effects 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- SJERSZKZAMCPFQ-UHFFFAOYSA-N 1-[2-(2-oxo-3h-1,3,4-oxadiazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC=C(C=2OC(=O)NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 SJERSZKZAMCPFQ-UHFFFAOYSA-N 0.000 claims 1
- OXBAZTJQAOWYEO-UHFFFAOYSA-N 1-[2-(2h-tetrazol-5-yl)-4-thiophen-3-ylphenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(C2=CSC=C2)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 OXBAZTJQAOWYEO-UHFFFAOYSA-N 0.000 claims 1
- AVGUGCMPZHFFFN-UHFFFAOYSA-N 1-[4-naphthalen-1-yl-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 AVGUGCMPZHFFFN-UHFFFAOYSA-N 0.000 claims 1
- VQBJJJXWHFPMKQ-UHFFFAOYSA-N 1-[4-naphthalen-2-yl-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(C=2C=C3C=CC=CC3=CC=2)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 VQBJJJXWHFPMKQ-UHFFFAOYSA-N 0.000 claims 1
- HUBHORIFRWPUBD-UHFFFAOYSA-N 1-[4-pyridin-3-yl-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(C=2C=NC=CC=2)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 HUBHORIFRWPUBD-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 abstract description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 241001024304 Mino Species 0.000 abstract description 2
- 125000005418 aryl aryl group Chemical group 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 26
- 239000004480 active ingredient Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000725 suspension Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 210000003743 erythrocyte Anatomy 0.000 description 10
- 239000003826 tablet Substances 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 210000004379 membrane Anatomy 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 230000004907 flux Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 108010016797 Sickle Hemoglobin Proteins 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 239000007937 lozenge Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006392 deoxygenation reaction Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000004410 intraocular pressure Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RJMGFBLUESJXEQ-UHFFFAOYSA-N 1-[2-(5-oxo-1h-1,2,4-triazol-2-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC=C(N2NC(=O)N=C2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 RJMGFBLUESJXEQ-UHFFFAOYSA-N 0.000 description 2
- HMTUJPZREZVLTC-UHFFFAOYSA-N 1-[4-(furan-3-yl)-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(C2=COC=C2)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 HMTUJPZREZVLTC-UHFFFAOYSA-N 0.000 description 2
- KMMQBTQXLFANBB-UHFFFAOYSA-N 1-[4-amino-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(N)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 KMMQBTQXLFANBB-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- PNISDQZEZLFVKO-UHFFFAOYSA-N 4-[4-[n-carbamoyl-3-(trifluoromethyl)anilino]-3-(2h-tetrazol-5-yl)phenyl]benzoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C(O)=O)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 PNISDQZEZLFVKO-UHFFFAOYSA-N 0.000 description 2
- SIAVMDKGVRXFAX-UHFFFAOYSA-N 4-carboxyphenylboronic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C=C1 SIAVMDKGVRXFAX-UHFFFAOYSA-N 0.000 description 2
- 241000220479 Acacia Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- MMNICIJVQJJHHF-UHFFFAOYSA-N Cetiedil Chemical compound C1CCCCC1C(C1=CSC=C1)C(=O)OCCN1CCCCCC1 MMNICIJVQJJHHF-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 208000007502 anemia Diseases 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229960003549 cetiedil Drugs 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- ZUHBJLCMPPFGJO-UHFFFAOYSA-N n-[4-[n-carbamoyl-3-(trifluoromethyl)anilino]-3-(2h-tetrazol-5-yl)phenyl]acetamide Chemical compound N=1N=NNC=1C1=CC(NC(=O)C)=CC=C1N(C(N)=O)C1=CC=CC(C(F)(F)F)=C1 ZUHBJLCMPPFGJO-UHFFFAOYSA-N 0.000 description 2
- 210000003928 nasal cavity Anatomy 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 102220240796 rs553605556 Human genes 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- GNRHNKBJNUVWFZ-UHFFFAOYSA-N (4-carbamoylphenyl)boronic acid Chemical compound NC(=O)C1=CC=C(B(O)O)C=C1 GNRHNKBJNUVWFZ-UHFFFAOYSA-N 0.000 description 1
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
- 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
- 125000004508 1,2,5-oxadiazol-4-yl group Chemical group O1N=CC(=N1)* 0.000 description 1
- 125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 description 1
- 125000004519 1,2,5-thiadiazol-4-yl group Chemical group S1N=CC(=N1)* 0.000 description 1
- GOFIUEUUROFVMA-UHFFFAOYSA-N 1-(1h-indol-5-yl)ethanone Chemical compound CC(=O)C1=CC=C2NC=CC2=C1 GOFIUEUUROFVMA-UHFFFAOYSA-N 0.000 description 1
- DQYPZIFRMCRLHE-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-[2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C=1C=CC=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(Cl)=C1 DQYPZIFRMCRLHE-UHFFFAOYSA-N 0.000 description 1
- AGMGBMQVFDFWKF-UHFFFAOYSA-N 1-[2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]thiourea Chemical compound C=1C=CC=C(C=2NN=NN=2)C=1N(C(=S)N)C1=CC=CC(C(F)(F)F)=C1 AGMGBMQVFDFWKF-UHFFFAOYSA-N 0.000 description 1
- VVNRISUAOQVRPG-UHFFFAOYSA-N 1-[2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 VVNRISUAOQVRPG-UHFFFAOYSA-N 0.000 description 1
- HCPZAMPYBSCWPY-UHFFFAOYSA-N 1-[2-(2h-tetrazol-5-yl)phenyl]-1-[4-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=C(C(F)(F)F)C=C1 HCPZAMPYBSCWPY-UHFFFAOYSA-N 0.000 description 1
- JPVQUBBVVQFJTC-UHFFFAOYSA-N 1-[4-bromo-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea;1-isocyanato-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=C=O)=C1.C=1C=C(Br)C=C(C2=NNN=N2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 JPVQUBBVVQFJTC-UHFFFAOYSA-N 0.000 description 1
- WTBROQALTWPXJD-UHFFFAOYSA-N 1-[4-phenyl-2-(2h-tetrazol-5-yl)phenyl]-1-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C(C=2C=CC=CC=2)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 WTBROQALTWPXJD-UHFFFAOYSA-N 0.000 description 1
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- DDZNZNHGKDEIDK-UHFFFAOYSA-N 1-phenyl-1-[2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C=1C=CC=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC=C1 DDZNZNHGKDEIDK-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YNMFGZWXMBKNIK-UHFFFAOYSA-N 2-(2-amino-4-bromophenyl)-1h-1,2,4-triazol-5-one Chemical compound NC1=CC(Br)=CC=C1N1NC(=O)N=C1 YNMFGZWXMBKNIK-UHFFFAOYSA-N 0.000 description 1
- PJZSLSTVOOQRLT-UHFFFAOYSA-N 2-(2-amino-4-phenylphenyl)-1h-1,2,4-triazol-5-one Chemical compound NC1=CC(C=2C=CC=CC=2)=CC=C1N1C=NC(=O)N1 PJZSLSTVOOQRLT-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- GUCGQKSPWMDAEX-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)aniline Chemical compound NC1=CC=CC=C1C1=NNN=N1 GUCGQKSPWMDAEX-UHFFFAOYSA-N 0.000 description 1
- CWLZVWCWIXSCKD-UHFFFAOYSA-N 2-(4-hydroxy-1,2,4-triazol-3-yl)aniline Chemical compound NC1=CC=CC=C1C1=NN=CN1O CWLZVWCWIXSCKD-UHFFFAOYSA-N 0.000 description 1
- HSKRHNHJEOBQPN-UHFFFAOYSA-N 2-[n-carbamoyl-3-(trifluoromethyl)anilino]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 HSKRHNHJEOBQPN-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- CATSHJCKVONEFX-UHFFFAOYSA-N 4-bromo-2-(2h-tetrazol-5-yl)aniline Chemical compound NC1=CC=C(Br)C=C1C1=NN=NN1 CATSHJCKVONEFX-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGTJLJZQQFGTJD-UHFFFAOYSA-N Carbonylcyanide-3-chlorophenylhydrazone Chemical compound ClC1=CC=CC(NN=C(C#N)C#N)=C1 UGTJLJZQQFGTJD-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- YVCXOEHJAXPTER-UHFFFAOYSA-N FC(C=1C(=C(C=CC1)NC(=O)N)C(=O)O)(F)F Chemical compound FC(C=1C(=C(C=CC1)NC(=O)N)C(=O)O)(F)F YVCXOEHJAXPTER-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000026350 Inborn Genetic disease Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000238383 Loligo Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- YOGKIHDBBUFCER-UHFFFAOYSA-N N1N=NN=C1N(C(=O)N)C1=CC=CC=C1 Chemical compound N1N=NN=C1N(C(=O)N)C1=CC=CC=C1 YOGKIHDBBUFCER-UHFFFAOYSA-N 0.000 description 1
- XBWQIZTWXVQHGL-UHFFFAOYSA-N NC1=C(C#N)C=CC(=C1)C1=COC=C1.NC1=C(C#N)C=CC(=C1)C1=CC=C(C=C1)C(F)(F)F.NC1=C(C#N)C=CC(=C1)C1=CC=CC2=CC=CC=C12.NC1=C(C#N)C=CC(=C1)C=1C=NC=CC1.NC1=C(C#N)C=CC(=C1)C1=CC2=CC=CC=C2C=C1 Chemical compound NC1=C(C#N)C=CC(=C1)C1=COC=C1.NC1=C(C#N)C=CC(=C1)C1=CC=C(C=C1)C(F)(F)F.NC1=C(C#N)C=CC(=C1)C1=CC=CC2=CC=CC=C12.NC1=C(C#N)C=CC(=C1)C=1C=NC=CC1.NC1=C(C#N)C=CC(=C1)C1=CC2=CC=CC=C2C=C1 XBWQIZTWXVQHGL-UHFFFAOYSA-N 0.000 description 1
- FDEACPIYUCUUCM-UHFFFAOYSA-N NC1=C(C#N)C=CC=C1.NC1=C(C=CC=C1)C1=NN=NN1 Chemical compound NC1=C(C#N)C=CC=C1.NC1=C(C=CC=C1)C1=NN=NN1 FDEACPIYUCUUCM-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 108010067973 Valinomycin Proteins 0.000 description 1
- 206010053648 Vascular occlusion Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 241001080519 Zera Species 0.000 description 1
- QJYYVSIRDJVQJW-UHFFFAOYSA-N [4-(dimethylcarbamoyl)phenyl]boronic acid Chemical compound CN(C)C(=O)C1=CC=C(B(O)O)C=C1 QJYYVSIRDJVQJW-UHFFFAOYSA-N 0.000 description 1
- ICPBJKWHDBFRAV-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC1N1NC(N=C1)=O)C1=CC=CC=C1.NC1=C(C#N)C=CC(=C1)C1=CC=C(C=C1)C(=O)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC1N1NC(N=C1)=O)C1=CC=CC=C1.NC1=C(C#N)C=CC(=C1)C1=CC=C(C=C1)C(=O)N ICPBJKWHDBFRAV-UHFFFAOYSA-N 0.000 description 1
- YPMCBEBTVKFDSU-UHFFFAOYSA-N [N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[K+].[K+].[K+] Chemical compound [N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[K+].[K+].[K+] YPMCBEBTVKFDSU-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000003050 axon Anatomy 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002727 chloride channel blocking agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- FCFNRCROJUBPLU-UHFFFAOYSA-N compound M126 Natural products CC(C)C1NC(=O)C(C)OC(=O)C(C(C)C)NC(=O)C(C(C)C)OC(=O)C(C(C)C)NC(=O)C(C)OC(=O)C(C(C)C)NC(=O)C(C(C)C)OC(=O)C(C(C)C)NC(=O)C(C)OC(=O)C(C(C)C)NC(=O)C(C(C)C)OC1=O FCFNRCROJUBPLU-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 230000009395 genetic defect Effects 0.000 description 1
- 208000016361 genetic disease Diseases 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 description 1
- 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 description 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 description 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- NERSCRJAMJDGOP-UHFFFAOYSA-N n-[4-[n-carbamoyl-3-(trifluoromethyl)anilino]-3-(2h-tetrazol-5-yl)phenyl]benzamide Chemical compound C=1C=C(NC(=O)C=2C=CC=CC=2)C=C(C=2NN=NN=2)C=1N(C(=O)N)C1=CC=CC(C(F)(F)F)=C1 NERSCRJAMJDGOP-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- INTJZENRAYCATA-UHFFFAOYSA-N pyrrol-3-one Chemical compound O=C1C=CN=C1 INTJZENRAYCATA-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 210000002363 skeletal muscle cell Anatomy 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- FCFNRCROJUBPLU-DNDCDFAISA-N valinomycin Chemical compound CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC1=O FCFNRCROJUBPLU-DNDCDFAISA-N 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/47—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK45297 | 1997-04-22 | ||
| DK0452/97 | 1997-04-22 | ||
| PCT/DK1998/000162 WO1998047879A1 (en) | 1997-04-22 | 1998-04-21 | Substituted phenyl derivatives, their preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001521532A true JP2001521532A (ja) | 2001-11-06 |
| JP2001521532A5 JP2001521532A5 (enExample) | 2007-04-05 |
Family
ID=8093724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54475998A Abandoned JP2001521532A (ja) | 1997-04-22 | 1998-04-21 | 置換されたフエニル誘導体、その製造方法及びその使用方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6297261B1 (enExample) |
| EP (1) | EP0977741B1 (enExample) |
| JP (1) | JP2001521532A (enExample) |
| CN (1) | CN1118462C (enExample) |
| AT (1) | ATE248824T1 (enExample) |
| AU (1) | AU728520B2 (enExample) |
| BR (1) | BR9808938A (enExample) |
| CA (1) | CA2285424A1 (enExample) |
| CZ (1) | CZ295822B6 (enExample) |
| DE (1) | DE69817802T2 (enExample) |
| DK (1) | DK0977741T3 (enExample) |
| ES (1) | ES2205472T3 (enExample) |
| IL (1) | IL132107A (enExample) |
| NZ (1) | NZ337976A (enExample) |
| PT (1) | PT977741E (enExample) |
| RU (1) | RU2197482C2 (enExample) |
| SK (1) | SK282818B6 (enExample) |
| TR (1) | TR199902593T2 (enExample) |
| WO (1) | WO1998047879A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001526258A (ja) * | 1997-12-22 | 2001-12-18 | バイエル コーポレイション | 対称および非対称置換ジフェニル尿素を用いるrafキナーゼの阻害 |
| JP2005538152A (ja) * | 2002-09-05 | 2005-12-15 | ニューロサーチ、アクティーゼルスカブ | ジアリール誘導体及びこれをクロライドチャネル遮断剤として使用する方法 |
| JP2006527735A (ja) * | 2003-06-17 | 2006-12-07 | ノイロサーチ アクティーゼルスカブ | ジフェニル尿素誘導体、及びクロライドチャネル遮断剤としてのそれらの使用 |
| JP2007504202A (ja) * | 2003-09-04 | 2007-03-01 | ポセイドン ファーマシュティカルズ アクティーゼルスカブ | 心臓不整脈を治療するためのergチャネル開口薬 |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6696475B2 (en) | 1997-04-22 | 2004-02-24 | Neurosearch A/S | Substituted phenyl derivatives, their preparation and use |
| CN1263733C (zh) | 1998-10-22 | 2006-07-12 | 神经研究公司 | 取代苯基衍生物,它们的制备和用途 |
| US20050080112A1 (en) * | 2001-06-22 | 2005-04-14 | Madsen Lars Siim | Compounds for use in disorders associated with mast cell or basophil acitvity |
| US7087631B2 (en) * | 2002-07-18 | 2006-08-08 | Inotek Pharmaceuticals Corporation | Aryltetrazole compounds, and compositions thereof |
| US7078423B2 (en) * | 2002-07-18 | 2006-07-18 | Inotek Pharmaceuticals Corporation | 5-Aryltetrazole compounds, compositions thereof, and uses therefor |
| CA2493253A1 (en) * | 2002-08-01 | 2004-02-12 | Neurosearch A/S | Compounds useful for the treatment of diseases responsive to antiangiogenetic therapy |
| WO2004022525A1 (en) * | 2002-09-05 | 2004-03-18 | Neurosearch A/S | Amide derivatives and their use as chloride channel blockers |
| US7041693B2 (en) * | 2002-10-04 | 2006-05-09 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
| JP2006507329A (ja) | 2002-11-21 | 2006-03-02 | ニューロサーチ、アクティーゼルスカブ | 新規アリールウレイド安息香酸誘導体及びその使用 |
| US20060229335A1 (en) * | 2002-12-24 | 2006-10-12 | Bradley Teegarden | Diarylamine and arylheteroarylamine pyrazole derivatives as modulators of 5ht2a |
| HRP20060100T3 (en) | 2003-07-22 | 2007-03-31 | Arena Pharmaceuticals Inc | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of disorders related thereto |
| US7202363B2 (en) | 2003-07-24 | 2007-04-10 | Abbott Laboratories | Thienopyridine and furopyridine kinase inhibitors |
| WO2005023238A1 (en) * | 2003-09-04 | 2005-03-17 | Poseidon Pharmaceuticals A/S | Erg channel openers for the treatment of hyperexcitability-related neuronal diseases |
| JP2007509846A (ja) * | 2003-10-15 | 2007-04-19 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | テトラヒドロ−ナフタレンおよび尿素誘導体 |
| JP2007528420A (ja) * | 2004-03-11 | 2007-10-11 | グラクソ グループ リミテッド | 新規m3ムスカリン性アセチルコリン受容体アンタゴニスト |
| CN1926114B (zh) * | 2004-03-23 | 2011-08-24 | 艾尼纳制药公司 | 用于制备经取代n-芳基-n′-′3-(1h-吡唑-5-基)苯基脲及其中间体的方法 |
| SA05260357B1 (ar) * | 2004-11-19 | 2008-09-08 | ارينا فارماسيتو تيكالز ، أنك | مشتقات 3_فينيل_بيرازول كمعدلات لمستقبل سيروتينين 5_ht2a مفيدة في علاج الاضطرابات المتعلقه به |
| US20070078121A1 (en) * | 2004-12-23 | 2007-04-05 | Flynn Daniel L | Enzyme modulators and treatments |
| USRE45336E1 (en) | 2006-05-18 | 2015-01-13 | Arena Pharmaceuticals, Inc. | Primary amines and derivatives thereof as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| WO2007136689A2 (en) | 2006-05-18 | 2007-11-29 | Arena Pharmaceuticals, Inc. | Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor |
| CA2646076C (en) | 2006-05-18 | 2015-06-30 | Arena Pharmaceuticals, Inc. | Ethers, secondary amines and derivatives thereof as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| TWI415845B (zh) * | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與5-ht2a血清素受體相關聯病症之作為5-ht2a血清素受體之調節劑的吡唑衍生物 |
| US7790756B2 (en) * | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| US20100137381A1 (en) | 2007-05-03 | 2010-06-03 | Neurosearch A/S | Acetamide derivatives as potassium channel modulators |
| EP2190844B3 (en) | 2007-08-15 | 2013-07-17 | Arena Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| WO2009123714A2 (en) * | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto |
| TR201805216T4 (en) | 2008-10-28 | 2018-06-21 | Arena Pharm Inc | COMPOSITIONS OF A USEFUL 5-HT2A SEROTONINE RECEPTOR MODULATOR FOR THE TREATMENT OF RELATED DISORDERS |
| KR101639642B1 (ko) | 2008-12-05 | 2016-07-14 | 애브비 바하마스 리미티드 | 암 치료에 사용하기 위한 키나제 억제제로서의 티에노[3,2-c]피리딘 유도체 |
| WO2011075596A1 (en) | 2009-12-18 | 2011-06-23 | Arena Pharmaceuticals, Inc. | Crystalline forms of certain 3-phenyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| WO2013012909A1 (en) | 2011-07-20 | 2013-01-24 | Abbott Laboratories | Kinase inhibitor with improved aqueous solubility |
| CN103709185A (zh) * | 2013-12-30 | 2014-04-09 | 大连联化医药技术有限公司 | 一种4-(n-甲基甲酰氨)苯基硼酸的制备方法 |
| JP2018516992A (ja) | 2015-06-12 | 2018-06-28 | アクソファント サイエンシーズ ゲーエムベーハーAxovant Sciences Gmbh | レム睡眠行動障害の予防および処置のために有用なジアリールおよびアリールヘテロアリール尿素誘導体 |
| WO2017011767A2 (en) | 2015-07-15 | 2017-01-19 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease |
| SI3622953T1 (sl) | 2016-05-17 | 2021-05-31 | Scandion Oncology A/S | Kombinirano zdravljenje raka |
| WO2019014352A1 (en) | 2017-07-11 | 2019-01-17 | Vertex Pharmaceuticals Incorporated | CARBOXAMIDES AS INHIBITORS OF SODIUM CHANNELS |
| WO2020146682A1 (en) | 2019-01-10 | 2020-07-16 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
| US12440481B2 (en) | 2019-01-10 | 2025-10-14 | Vertex Pharmaceuticals Incorporated | Esters and carbamates as modulators of sodium channels |
| CN117229258B (zh) * | 2022-06-07 | 2024-07-19 | 杭州壹瑞医药科技有限公司 | N-四唑基芳基脲类衍生物及其制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3682136D1 (de) | 1985-07-31 | 1991-11-28 | Hoechst Ag | N-substituierte 5-nitroanthranilsaeuren, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen. |
| US4889612A (en) | 1987-05-22 | 1989-12-26 | Abbott Laboratories | Ion-selective electrode having a non-metal sensing element |
| US5489612A (en) | 1991-08-23 | 1996-02-06 | The University Of Alabama At Birmingham Research Foundation | Calixarene chloride-channel blockers |
| US5273992A (en) | 1992-11-02 | 1993-12-28 | Beth Israel Hospital Assoc. Inc. | Method for reducing sickle erythrocyte dehydration and delaying the occurrence of erythrocyte sickling in-situ |
| DK41193D0 (da) | 1993-04-07 | 1993-04-07 | Neurosearch As | Ionkanalaabnere |
| US5362744A (en) * | 1993-11-22 | 1994-11-08 | Warner-Lambert Company | Tetrazole-substituted urea acat inhibitors |
| US5559151A (en) | 1994-11-30 | 1996-09-24 | Allergan | Method for reducing intraocular pressure in the mammalian eye by administration of chloride channel blockers |
| IL126922A0 (en) * | 1996-05-24 | 1999-09-22 | Neurosearch As | Phenyl derivatives containing an acidic group their preparation and their use as chloride channel blockers |
| AU2962297A (en) * | 1996-05-24 | 1998-01-05 | Neurosearch A/S | Phenyl derivatives useful as blockers of chloride channels |
-
1998
- 1998-04-21 EP EP98914851A patent/EP0977741B1/en not_active Expired - Lifetime
- 1998-04-21 WO PCT/DK1998/000162 patent/WO1998047879A1/en not_active Ceased
- 1998-04-21 ES ES98914851T patent/ES2205472T3/es not_active Expired - Lifetime
- 1998-04-21 NZ NZ337976A patent/NZ337976A/en unknown
- 1998-04-21 DK DK98914851T patent/DK0977741T3/da active
- 1998-04-21 BR BR9808938-2A patent/BR9808938A/pt not_active Application Discontinuation
- 1998-04-21 RU RU99124188/04A patent/RU2197482C2/ru not_active IP Right Cessation
- 1998-04-21 SK SK1447-99A patent/SK282818B6/sk not_active IP Right Cessation
- 1998-04-21 AT AT98914851T patent/ATE248824T1/de not_active IP Right Cessation
- 1998-04-21 AU AU69196/98A patent/AU728520B2/en not_active Ceased
- 1998-04-21 DE DE69817802T patent/DE69817802T2/de not_active Expired - Lifetime
- 1998-04-21 TR TR1999/02593T patent/TR199902593T2/xx unknown
- 1998-04-21 PT PT98914851T patent/PT977741E/pt unknown
- 1998-04-21 US US09/402,165 patent/US6297261B1/en not_active Expired - Fee Related
- 1998-04-21 CN CN98804446A patent/CN1118462C/zh not_active Expired - Fee Related
- 1998-04-21 CZ CZ19993699A patent/CZ295822B6/cs not_active IP Right Cessation
- 1998-04-21 JP JP54475998A patent/JP2001521532A/ja not_active Abandoned
- 1998-04-21 IL IL13210798A patent/IL132107A/en not_active IP Right Cessation
- 1998-04-21 CA CA002285424A patent/CA2285424A1/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001526258A (ja) * | 1997-12-22 | 2001-12-18 | バイエル コーポレイション | 対称および非対称置換ジフェニル尿素を用いるrafキナーゼの阻害 |
| JP2005538152A (ja) * | 2002-09-05 | 2005-12-15 | ニューロサーチ、アクティーゼルスカブ | ジアリール誘導体及びこれをクロライドチャネル遮断剤として使用する方法 |
| JP2006527735A (ja) * | 2003-06-17 | 2006-12-07 | ノイロサーチ アクティーゼルスカブ | ジフェニル尿素誘導体、及びクロライドチャネル遮断剤としてのそれらの使用 |
| JP2007504202A (ja) * | 2003-09-04 | 2007-03-01 | ポセイドン ファーマシュティカルズ アクティーゼルスカブ | 心臓不整脈を治療するためのergチャネル開口薬 |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ369999A3 (cs) | 2000-02-16 |
| EP0977741B1 (en) | 2003-09-03 |
| US6297261B1 (en) | 2001-10-02 |
| IL132107A (en) | 2004-09-27 |
| BR9808938A (pt) | 2000-08-01 |
| RU2197482C2 (ru) | 2003-01-27 |
| HK1026909A1 (en) | 2000-12-29 |
| CN1118462C (zh) | 2003-08-20 |
| WO1998047879A1 (en) | 1998-10-29 |
| ATE248824T1 (de) | 2003-09-15 |
| CA2285424A1 (en) | 1998-10-29 |
| NZ337976A (en) | 2001-05-25 |
| SK144799A3 (en) | 2000-05-16 |
| CZ295822B6 (cs) | 2005-11-16 |
| DE69817802D1 (de) | 2003-10-09 |
| IL132107A0 (en) | 2001-03-19 |
| SK282818B6 (sk) | 2002-12-03 |
| CN1253553A (zh) | 2000-05-17 |
| PT977741E (pt) | 2004-01-30 |
| DK0977741T3 (da) | 2003-12-01 |
| EP0977741A1 (en) | 2000-02-09 |
| ES2205472T3 (es) | 2004-05-01 |
| AU6919698A (en) | 1998-11-13 |
| DE69817802T2 (de) | 2004-04-08 |
| AU728520B2 (en) | 2001-01-11 |
| TR199902593T2 (xx) | 2000-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2001521532A (ja) | 置換されたフエニル誘導体、その製造方法及びその使用方法 | |
| JP4073489B2 (ja) | 酸性基を有するフエニル誘導体、その製造方法及びそれをクロライドチャンネル遮断剤として使用する方法 | |
| JP3040485B2 (ja) | ベンズイミダゾール化合物、およびgabaaレセプター複合体モジュレーターとしてのその使用 | |
| KR100799892B1 (ko) | 치환된 페닐 유도체 및 이를 포함하는 약제학적 조성물 | |
| US6696475B2 (en) | Substituted phenyl derivatives, their preparation and use | |
| JP2000510862A (ja) | クロライドチャンネル遮断剤として有用なフエニル誘導体 | |
| JP2002526522A (ja) | ジアミノシクロブテン−3,4−ジオン誘導体、その製造方法及びその使用方法 | |
| HK1026909B (en) | Substituted phenyl derivatives, their preparation and use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050307 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050307 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20060911 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20060922 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060926 |
|
| A762 | Written abandonment of application |
Free format text: JAPANESE INTERMEDIATE CODE: A762 Effective date: 20080512 |