TWI504589B - 作為香草類化合物受體之配體之經取代芳香族羧醯胺及尿素衍生物 - Google Patents
作為香草類化合物受體之配體之經取代芳香族羧醯胺及尿素衍生物 Download PDFInfo
- Publication number
- TWI504589B TWI504589B TW099114463A TW99114463A TWI504589B TW I504589 B TWI504589 B TW I504589B TW 099114463 A TW099114463 A TW 099114463A TW 99114463 A TW99114463 A TW 99114463A TW I504589 B TWI504589 B TW I504589B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- carbon atoms
- methyl
- substituted
- trifluoromethyl
- Prior art date
Links
- -1 aromatic carboxamide Chemical class 0.000 title claims description 501
- 108010062740 TRPV Cation Channels Proteins 0.000 title description 4
- 102000011040 TRPV Cation Channels Human genes 0.000 title description 3
- 150000003672 ureas Chemical class 0.000 title description 2
- 239000003446 ligand Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 885
- 125000000217 alkyl group Chemical group 0.000 claims description 502
- 125000003277 amino group Chemical group 0.000 claims description 489
- 125000001424 substituent group Chemical group 0.000 claims description 254
- 239000000460 chlorine Substances 0.000 claims description 230
- 229910052801 chlorine Inorganic materials 0.000 claims description 226
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 224
- 239000011737 fluorine Substances 0.000 claims description 224
- 229910052731 fluorine Inorganic materials 0.000 claims description 224
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 223
- 229910052794 bromium Inorganic materials 0.000 claims description 223
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 222
- 125000003545 alkoxy group Chemical group 0.000 claims description 213
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 152
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 142
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 139
- 229920006395 saturated elastomer Polymers 0.000 claims description 138
- 125000003118 aryl group Chemical group 0.000 claims description 133
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 132
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 119
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 117
- 125000001072 heteroaryl group Chemical group 0.000 claims description 103
- 125000000623 heterocyclic group Chemical group 0.000 claims description 102
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 97
- 229910052757 nitrogen Inorganic materials 0.000 claims description 95
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 89
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 85
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 78
- 229910052799 carbon Inorganic materials 0.000 claims description 75
- 150000001721 carbon Chemical group 0.000 claims description 73
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 73
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 68
- 125000002252 acyl group Chemical group 0.000 claims description 67
- 125000001153 fluoro group Chemical group F* 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 57
- 229910052717 sulfur Inorganic materials 0.000 claims description 57
- 150000001412 amines Chemical class 0.000 claims description 55
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 53
- 125000004434 sulfur atom Chemical group 0.000 claims description 53
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 52
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 52
- 125000004414 alkyl thio group Chemical group 0.000 claims description 51
- 125000004076 pyridyl group Chemical group 0.000 claims description 51
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 39
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 38
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 38
- 125000001544 thienyl group Chemical group 0.000 claims description 36
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 208000002193 Pain Diseases 0.000 claims description 25
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 24
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 238000006467 substitution reaction Methods 0.000 claims description 19
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 229940100389 Sulfonylurea Drugs 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 17
- 230000036407 pain Effects 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 16
- 229910052720 vanadium Inorganic materials 0.000 claims description 14
- 208000011117 substance-related disease Diseases 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000003172 aldehyde group Chemical group 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 239000011630 iodine Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 108050004388 Transient receptor potential cation channel subfamily V member 1 Proteins 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 10
- 125000004149 thio group Chemical group *S* 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 108010025083 TRPV1 receptor Proteins 0.000 claims description 8
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 206010013663 drug dependence Diseases 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000000879 imine group Chemical group 0.000 claims description 8
- 150000002466 imines Chemical group 0.000 claims description 8
- YSGBLPATSIPNLI-UHFFFAOYSA-N C(F)(F)(SC(SF)(Cl)Cl)Cl Chemical group C(F)(F)(SC(SF)(Cl)Cl)Cl YSGBLPATSIPNLI-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000000565 sulfonamide group Chemical group 0.000 claims description 7
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical group COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 206010013654 Drug abuse Diseases 0.000 claims description 5
- IUXKZVGPSBYUFA-UHFFFAOYSA-N FSC(Cl)Cl Chemical group FSC(Cl)Cl IUXKZVGPSBYUFA-UHFFFAOYSA-N 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 125000005427 anthranyl group Chemical group 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 230000007823 neuropathy Effects 0.000 claims description 5
- 201000001119 neuropathy Diseases 0.000 claims description 5
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical group 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 206010011224 Cough Diseases 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 208000003251 Pruritus Diseases 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 3
- 229960002504 capsaicin Drugs 0.000 claims description 3
- 235000017663 capsaicin Nutrition 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000006612 decyloxy group Chemical group 0.000 claims description 3
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
- 230000029142 excretion Effects 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 230000000626 neurodegenerative effect Effects 0.000 claims description 3
- PLXPTFQGYWXIEA-UHFFFAOYSA-N nitroformonitrile Chemical compound [O-][N+](=O)C#N PLXPTFQGYWXIEA-UHFFFAOYSA-N 0.000 claims description 3
- OTTPWWFPWBCJBS-UHFFFAOYSA-N o-(trifluoromethyl)hydroxylamine Chemical group NOC(F)(F)F OTTPWWFPWBCJBS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical group CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- FNGLQNMQHOAIJQ-UHFFFAOYSA-N Cl[S](Cl)Cl Chemical compound Cl[S](Cl)Cl FNGLQNMQHOAIJQ-UHFFFAOYSA-N 0.000 claims description 2
- 206010046543 Urinary incontinence Diseases 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003725 azepanyl group Chemical group 0.000 claims description 2
- 125000004069 aziridinyl group Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 2
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 2
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000532 dioxanyl group Chemical group 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000006038 hexenyl group Chemical group 0.000 claims description 2
- GZJRKAIDKPLXEA-UHFFFAOYSA-N hydroxy(trifluoromethoxy)cyanamide Chemical compound C(#N)N(OC(F)(F)F)O GZJRKAIDKPLXEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000005981 pentynyl group Chemical group 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 2
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 208000009935 visceral pain Diseases 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 56
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 52
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 24
- 239000004202 carbamide Substances 0.000 claims 24
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 7
- 208000024891 symptom Diseases 0.000 claims 7
- 208000007848 Alcoholism Diseases 0.000 claims 6
- 208000027418 Wounds and injury Diseases 0.000 claims 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 206010020853 Hypertonic bladder Diseases 0.000 claims 4
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 4
- 239000007822 coupling agent Substances 0.000 claims 4
- 230000006378 damage Effects 0.000 claims 4
- 208000014674 injury Diseases 0.000 claims 4
- 208000020629 overactive bladder Diseases 0.000 claims 4
- 208000017520 skin disease Diseases 0.000 claims 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- 208000004454 Hyperalgesia Diseases 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- RLWGDRLXZSLGHV-UHFFFAOYSA-N 1-[[4-(2-aminoethoxy)-3-methoxyphenyl]methyl]-3-[(4-tert-butylphenyl)methyl]urea Chemical compound C1=C(OCCN)C(OC)=CC(CNC(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1 RLWGDRLXZSLGHV-UHFFFAOYSA-N 0.000 claims 2
- OUEKLNJUMVZULZ-UHFFFAOYSA-N 2-[4-(2-aminoethoxy)-3-methoxyphenyl]-n-[3-(3,4-dimethylphenyl)propyl]acetamide;hydron;chloride Chemical compound Cl.C1=C(OCCN)C(OC)=CC(CC(=O)NCCCC=2C=C(C)C(C)=CC=2)=C1 OUEKLNJUMVZULZ-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006820 Arthralgia Diseases 0.000 claims 2
- 206010006482 Bronchospasm Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- IKYCZSUNGFRBJS-UHFFFAOYSA-N Euphorbia factor RL9 = U(1) = Resiniferatoxin Natural products COC1=CC(O)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 IKYCZSUNGFRBJS-UHFFFAOYSA-N 0.000 claims 2
- 206010015946 Eye irritation Diseases 0.000 claims 2
- 208000035154 Hyperesthesia Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010020843 Hyperthermia Diseases 0.000 claims 2
- 208000008081 Intestinal Fistula Diseases 0.000 claims 2
- OPZKBPQVWDSATI-KHPPLWFESA-N N-Vanillyloleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 OPZKBPQVWDSATI-KHPPLWFESA-N 0.000 claims 2
- QVLMCRFQGHWOPM-ZKWNWVNESA-N N-arachidonoyl vanillylamine Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC1=CC=C(O)C(OC)=C1 QVLMCRFQGHWOPM-ZKWNWVNESA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 208000004880 Polyuria Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 206010040880 Skin irritation Diseases 0.000 claims 2
- 208000007107 Stomach Ulcer Diseases 0.000 claims 2
- 206010052428 Wound Diseases 0.000 claims 2
- 230000002411 adverse Effects 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 206010001584 alcohol abuse Diseases 0.000 claims 2
- 208000025746 alcohol use disease Diseases 0.000 claims 2
- 230000036626 alertness Effects 0.000 claims 2
- 230000000172 allergic effect Effects 0.000 claims 2
- 208000022531 anorexia Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 230000003376 axonal effect Effects 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 230000007885 bronchoconstriction Effects 0.000 claims 2
- 210000000748 cardiovascular system Anatomy 0.000 claims 2
- 230000001149 cognitive effect Effects 0.000 claims 2
- 206010061428 decreased appetite Diseases 0.000 claims 2
- 230000035619 diuresis Effects 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 208000000718 duodenal ulcer Diseases 0.000 claims 2
- 210000001508 eye Anatomy 0.000 claims 2
- 231100000013 eye irritation Toxicity 0.000 claims 2
- 201000005917 gastric ulcer Diseases 0.000 claims 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 2
- 230000036031 hyperthermia Effects 0.000 claims 2
- 210000000936 intestine Anatomy 0.000 claims 2
- 230000007803 itching Effects 0.000 claims 2
- 238000002690 local anesthesia Methods 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 210000002850 nasal mucosa Anatomy 0.000 claims 2
- 210000005036 nerve Anatomy 0.000 claims 2
- 230000002981 neuropathic effect Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- OPZKBPQVWDSATI-UHFFFAOYSA-N oleoyl vanillylamide Natural products CCCCCCCCC=CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 OPZKBPQVWDSATI-UHFFFAOYSA-N 0.000 claims 2
- 229950010717 olvanil Drugs 0.000 claims 2
- 229940005483 opioid analgesics Drugs 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- DSDNAKHZNJAGHN-UHFFFAOYSA-N resinferatoxin Natural products C1=C(O)C(OC)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-UHFFFAOYSA-N 0.000 claims 2
- DSDNAKHZNJAGHN-MXTYGGKSSA-N resiniferatoxin Chemical compound C1=C(O)C(OC)=CC(CC(=O)OCC=2C[C@]3(O)C(=O)C(C)=C[C@H]3[C@@]34[C@H](C)C[C@@]5(O[C@@](O4)(CC=4C=CC=CC=4)O[C@@H]5[C@@H]3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-MXTYGGKSSA-N 0.000 claims 2
- 229940073454 resiniferatoxin Drugs 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 230000035946 sexual desire Effects 0.000 claims 2
- 210000003491 skin Anatomy 0.000 claims 2
- 230000036556 skin irritation Effects 0.000 claims 2
- 231100000475 skin irritation Toxicity 0.000 claims 2
- 210000003932 urinary bladder Anatomy 0.000 claims 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- WYBOZFUMORGCRV-UHFFFAOYSA-N 1-(1,3-benzothiazol-5-yl)-3-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=C3N=CSC3=CC=2)N1C1=CC=CC(Cl)=C1 WYBOZFUMORGCRV-UHFFFAOYSA-N 0.000 claims 1
- FCTLCIFCWATOJV-UHFFFAOYSA-N 1-(1,3-benzothiazol-6-yl)-3-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=C3SC=NC3=CC=2)N1C1=CC=CC(Cl)=C1 FCTLCIFCWATOJV-UHFFFAOYSA-N 0.000 claims 1
- RYKWRIADKOQIMZ-UHFFFAOYSA-N 1-(1,3-benzothiazol-6-yl)-3-[[2-(dipropylamino)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound CCCN(CCC)N1N=C(C(F)(F)F)C=C1CNC(=O)NC1=CC=C(N=CS2)C2=C1 RYKWRIADKOQIMZ-UHFFFAOYSA-N 0.000 claims 1
- OWYFAENZVWAAGQ-UHFFFAOYSA-N 1-(1,3-benzoxazol-6-yl)-3-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=C3OC=NC3=CC=2)N1C1=CC=CC(Cl)=C1 OWYFAENZVWAAGQ-UHFFFAOYSA-N 0.000 claims 1
- ZYJMFWDGJQRBQF-UHFFFAOYSA-N 1-(1-chloroisoquinolin-5-yl)-3-[[2-piperidin-1-yl-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C3=CC=NC(Cl)=C3C=CC=2)N1N1CCCCC1 ZYJMFWDGJQRBQF-UHFFFAOYSA-N 0.000 claims 1
- VJLYHMVBXPGYLB-UHFFFAOYSA-N 1-(1-methylisoquinolin-5-yl)-3-[[2-piperidin-1-yl-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound C1=CC=C2C(C)=NC=CC2=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1N1CCCCC1 VJLYHMVBXPGYLB-UHFFFAOYSA-N 0.000 claims 1
- BBTCXSCQIOBJCO-UHFFFAOYSA-N 1-(1h-indazol-4-yl)-3-[[2-[(4-methoxyphenyl)methyl]-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound C1=CC(OC)=CC=C1CN1C(CNC(=O)NC=2C=3C=NNC=3C=CC=2)=CC(C(F)(F)F)=N1 BBTCXSCQIOBJCO-UHFFFAOYSA-N 0.000 claims 1
- ACQCQISWSOMQLM-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=C3N=CNC3=CC=2)N1C1=CC=CC(Cl)=C1 ACQCQISWSOMQLM-UHFFFAOYSA-N 0.000 claims 1
- OTVDUMBPFDUTPU-UHFFFAOYSA-N 1-(5-chloro-1h-indazol-4-yl)-3-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=3C=NNC=3C=CC=2Cl)N1C1=CC=CC(Cl)=C1 OTVDUMBPFDUTPU-UHFFFAOYSA-N 0.000 claims 1
- BMTYNMKBRYVZER-UHFFFAOYSA-N 1-(7-hydroxynaphthalen-1-yl)-3-[[2-piperidin-1-yl-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound C12=CC(O)=CC=C2C=CC=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1N1CCCCC1 BMTYNMKBRYVZER-UHFFFAOYSA-N 0.000 claims 1
- ATABGOFXBKZNIL-UHFFFAOYSA-N 1-[(5-tert-butyl-2-cyclohexylsulfanylpyrazol-3-yl)methyl]-3-(2-methylquinolin-5-yl)urea Chemical compound C=1C=CC2=NC(C)=CC=C2C=1NC(=O)NCC1=CC(C(C)(C)C)=NN1SC1CCCCC1 ATABGOFXBKZNIL-UHFFFAOYSA-N 0.000 claims 1
- MTBOHROPUSRDDI-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-4-methyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1h-indazol-4-yl)urea Chemical compound N1=C(C(F)(F)F)C(C)=C(CNC(=O)NC=2C=3C=NNC=3C=CC=2)N1C1=CC=CC(Cl)=C1 MTBOHROPUSRDDI-UHFFFAOYSA-N 0.000 claims 1
- YJVCGMRRKRMMAM-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1-methylindol-4-yl)urea Chemical compound C1=CC=C2N(C)C=CC2=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 YJVCGMRRKRMMAM-UHFFFAOYSA-N 0.000 claims 1
- NAHYRLOXRZTJAL-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1h-indazol-4-yl)urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=3C=NNC=3C=CC=2)N1C1=CC=CC(Cl)=C1 NAHYRLOXRZTJAL-UHFFFAOYSA-N 0.000 claims 1
- MGIPRFBECFSHNE-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1h-indol-5-yl)urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=C3C=CNC3=CC=2)N1C1=CC=CC(Cl)=C1 MGIPRFBECFSHNE-UHFFFAOYSA-N 0.000 claims 1
- ISSPVONIBWMIFZ-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(2-methyl-1h-indol-5-yl)urea Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 ISSPVONIBWMIFZ-UHFFFAOYSA-N 0.000 claims 1
- WTFGFCWOYYKAID-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)urea Chemical compound C=12CC(O)CCC2=CC=CC=1NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 WTFGFCWOYYKAID-UHFFFAOYSA-N 0.000 claims 1
- NOKCIQZSXNFEOT-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(7-hydroxynaphthalen-1-yl)urea Chemical compound C12=CC(O)=CC=C2C=CC=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 NOKCIQZSXNFEOT-UHFFFAOYSA-N 0.000 claims 1
- WTFGFCWOYYKAID-KRWDZBQOSA-N 1-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-[(7s)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl]urea Chemical compound C([C@@H](CC1=2)O)CC1=CC=CC=2NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 WTFGFCWOYYKAID-KRWDZBQOSA-N 0.000 claims 1
- AWXGTGQTIIDGET-UHFFFAOYSA-N 1-[[2-(6-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(7-hydroxynaphthalen-1-yl)urea Chemical compound C12=CC(O)=CC=C2C=CC=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=N1 AWXGTGQTIIDGET-UHFFFAOYSA-N 0.000 claims 1
- ACZIBYYDHGOCNU-UHFFFAOYSA-N 1-[[2-(cyclopropylmethoxy)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1h-indazol-4-yl)urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=3C=NNC=3C=CC=2)N1OCC1CC1 ACZIBYYDHGOCNU-UHFFFAOYSA-N 0.000 claims 1
- XWSHDNGSZWCNNU-UHFFFAOYSA-N 1-[[2-(dipropylamino)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(7-hydroxynaphthalen-1-yl)urea Chemical compound CCCN(CCC)N1N=C(C(F)(F)F)C=C1CNC(=O)NC1=CC=CC2=CC=C(O)C=C12 XWSHDNGSZWCNNU-UHFFFAOYSA-N 0.000 claims 1
- ZBZSXUFNGWNHIG-UHFFFAOYSA-N 1-[[2-butoxy-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1-methylindazol-4-yl)urea Chemical compound CCCCON1N=C(C(F)(F)F)C=C1CNC(=O)NC1=CC=CC2=C1C=NN2C ZBZSXUFNGWNHIG-UHFFFAOYSA-N 0.000 claims 1
- UCXMVLGBHTYHEY-UHFFFAOYSA-N 1-[[2-butoxy-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1h-indazol-4-yl)urea Chemical compound CCCCON1N=C(C(F)(F)F)C=C1CNC(=O)NC1=CC=CC2=C1C=NN2 UCXMVLGBHTYHEY-UHFFFAOYSA-N 0.000 claims 1
- WIBYBAJKSDPGEY-UHFFFAOYSA-N 1-[[2-cyclohexylsulfanyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(7-hydroxynaphthalen-1-yl)urea Chemical compound C12=CC(O)=CC=C2C=CC=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1SC1CCCCC1 WIBYBAJKSDPGEY-UHFFFAOYSA-N 0.000 claims 1
- JRSNKTPUASWXHG-UHFFFAOYSA-N 1-[[2-cyclopentyloxy-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1h-indazol-4-yl)urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=3C=NNC=3C=CC=2)N1OC1CCCC1 JRSNKTPUASWXHG-UHFFFAOYSA-N 0.000 claims 1
- PSEWEOAZEQUPJX-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-(2,2-difluoro-1,3-benzodioxol-5-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=C3OC(F)(F)OC3=CC=2)N1C1=CC=CC(Cl)=C1 PSEWEOAZEQUPJX-UHFFFAOYSA-N 0.000 claims 1
- LXCJSADKPQQIMM-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-(2,3-dihydro-1-benzofuran-7-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=3OCCC=3C=CC=2)N1C1=CC=CC(Cl)=C1 LXCJSADKPQQIMM-UHFFFAOYSA-N 0.000 claims 1
- HXGIGQBRICUXJO-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-(5,6,7,8-tetrahydronaphthalen-1-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=3CCCCC=3C=CC=2)N1C1=CC=CC(Cl)=C1 HXGIGQBRICUXJO-UHFFFAOYSA-N 0.000 claims 1
- FGJXRMQPCDXJDM-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-(5-hydroxynaphthalen-2-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=C3C=CC=C(O)C3=CC=2)N1C1=CC=CC(Cl)=C1 FGJXRMQPCDXJDM-UHFFFAOYSA-N 0.000 claims 1
- VIQDFUAVDNIDBW-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-(6-hydroxynaphthalen-2-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=C3C=CC(O)=CC3=CC=2)N1C1=CC=CC(Cl)=C1 VIQDFUAVDNIDBW-UHFFFAOYSA-N 0.000 claims 1
- CEFMLFJJFAGHIX-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-(7-hydroxynaphthalen-1-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C3=CC(O)=CC=C3C=CC=2)N1C1=CC=CC(Cl)=C1 CEFMLFJJFAGHIX-UHFFFAOYSA-N 0.000 claims 1
- LLOWTJRQPVVLCO-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-isoquinolin-4-ylurea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C3=CC=CC=C3C=NC=2)N1C1=CC=CC(Cl)=C1 LLOWTJRQPVVLCO-UHFFFAOYSA-N 0.000 claims 1
- XQUJSMJJIJSXBT-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-isoquinolin-8-ylurea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C3=CN=CC=C3C=CC=2)N1C1=CC=CC(Cl)=C1 XQUJSMJJIJSXBT-UHFFFAOYSA-N 0.000 claims 1
- SLAAORPLPUTGAR-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-naphthalen-1-ylurea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C3=CC=CC=C3C=CC=2)N1C1=CC=CC(Cl)=C1 SLAAORPLPUTGAR-UHFFFAOYSA-N 0.000 claims 1
- OMUMJYZPZYEXBH-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-quinolin-3-ylurea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=C3C=CC=CC3=NC=2)N1C1=CC=CC(Cl)=C1 OMUMJYZPZYEXBH-UHFFFAOYSA-N 0.000 claims 1
- LUBCKCSIZNBBRJ-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(6-chloropyridin-2-yl)pyrazol-3-yl]methyl]-3-(1-methylisoquinolin-5-yl)urea Chemical compound C1=CC=C2C(C)=NC=CC2=C1NC(=O)NCC1=CC(C(C)(C)C)=NN1C1=CC=CC(Cl)=N1 LUBCKCSIZNBBRJ-UHFFFAOYSA-N 0.000 claims 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
- SWTYEGKNPYREDM-UHFFFAOYSA-N 2-(2-methylquinolin-5-yl)-n-[[2-piperidin-1-yl-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound C=1C=CC2=NC(C)=CC=C2C=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1N1CCCCC1 SWTYEGKNPYREDM-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- FRVWXHTYEWELNU-UHFFFAOYSA-N 3-tert-butyl-1-(3-chlorophenyl)pyrazole Chemical compound N1=C(C(C)(C)C)C=CN1C1=CC=CC(Cl)=C1 FRVWXHTYEWELNU-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 208000001387 Causalgia Diseases 0.000 claims 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 1
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims 1
- 208000010201 Exanthema Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims 1
- 206010021639 Incontinence Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 229960000643 adenine Drugs 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 206010053552 allodynia Diseases 0.000 claims 1
- 230000000049 anti-anxiety effect Effects 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 201000005884 exanthem Diseases 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000005980 hexynyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 1
- VLTBIKSCTKKEOQ-UHFFFAOYSA-N isoquinolin-5-ylurea Chemical compound N1=CC=C2C(NC(=O)N)=CC=CC2=C1 VLTBIKSCTKKEOQ-UHFFFAOYSA-N 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 claims 1
- 230000037023 motor activity Effects 0.000 claims 1
- JZVXRVBFWJRZSK-UHFFFAOYSA-N n-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-2-quinolin-6-ylpropanamide Chemical compound C=1C=C2N=CC=CC2=CC=1C(C)C(=O)NCC1=CC(C(C)(C)C)=NN1C1=CC=CC(Cl)=C1 JZVXRVBFWJRZSK-UHFFFAOYSA-N 0.000 claims 1
- PVJUWEUISFBADS-UHFFFAOYSA-N n-[[5-tert-butyl-2-(cyclohexen-1-yl)pyrazol-3-yl]methyl]-2-(7-hydroxynaphthalen-1-yl)propanamide Chemical compound C=1C=CC2=CC=C(O)C=C2C=1C(C)C(=O)NCC1=CC(C(C)(C)C)=NN1C1=CCCCC1 PVJUWEUISFBADS-UHFFFAOYSA-N 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 230000001452 natriuretic effect Effects 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 206010037844 rash Diseases 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 230000036325 urinary excretion Effects 0.000 claims 1
- 210000001835 viscera Anatomy 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 113
- 239000002585 base Substances 0.000 description 18
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 description 5
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000005138 alkoxysulfonyl group Chemical group 0.000 description 4
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
- 125000005142 aryl oxy sulfonyl group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 description 3
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 3
- 125000005368 heteroarylthio group Chemical group 0.000 description 3
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000019136 lipoic acid Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 229960002663 thioctic acid Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 description 1
- FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- VIKBNMWOLLIQPG-UHFFFAOYSA-N 2-methyldecanedioic acid Chemical compound OC(=O)C(C)CCCCCCCC(O)=O VIKBNMWOLLIQPG-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- XSMGUHQJAWSIJI-UHFFFAOYSA-N N(=S(=O)=O)OS Chemical group N(=S(=O)=O)OS XSMGUHQJAWSIJI-UHFFFAOYSA-N 0.000 description 1
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 102000003566 TRPV1 Human genes 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 101150016206 Trpv1 gene Proteins 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 125000004651 chloromethoxy group Chemical group ClCO* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
- 125000005366 cycloalkylthio group Chemical group 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical group FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- BPFZRKQDXVZTFD-UHFFFAOYSA-N disulfur decafluoride Chemical compound FS(F)(F)(F)(F)S(F)(F)(F)(F)F BPFZRKQDXVZTFD-UHFFFAOYSA-N 0.000 description 1
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003753 nitric oxide Drugs 0.000 description 1
- 235000019391 nitrogen oxide Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000005824 oxyalkoxy group Chemical group 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 150000003871 sulfonates Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- 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
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Virology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Reproductive Health (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Gynecology & Obstetrics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17627709P | 2009-05-07 | 2009-05-07 | |
| EP09006221 | 2009-05-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201120010A TW201120010A (en) | 2011-06-16 |
| TWI504589B true TWI504589B (zh) | 2015-10-21 |
Family
ID=40848721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099114463A TWI504589B (zh) | 2009-05-07 | 2010-05-06 | 作為香草類化合物受體之配體之經取代芳香族羧醯胺及尿素衍生物 |
Country Status (16)
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110092554A1 (en) * | 2007-11-19 | 2011-04-21 | Richard Chesworth | 1,3,5 tri-subtituted benzenes for treatment of alzheimer's disease and other disorders |
| WO2009086277A1 (en) | 2007-12-20 | 2009-07-09 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
| US8946204B2 (en) * | 2009-05-07 | 2015-02-03 | Gruenenthal Gmbh | Substituted phenylureas and phenylamides as vanilloid receptor ligands |
| RU2553392C2 (ru) * | 2009-05-07 | 2015-06-10 | Грюненталь Гмбх | Замещенные фенилмочевины и фениламиды в качестве лигандов ваниллоидных рецепторов |
| SG10201502484SA (en) | 2010-03-30 | 2015-05-28 | Verseon Corp | Multisubstituted aromatic compounds as inhibitors of thrombin |
| HK1198697A1 (en) | 2011-07-26 | 2015-05-29 | Grünenthal GmbH | Substituted heteroaromatic pyrazole-containing carboxamide and urea derivatives as vanilloid receptor ligands |
| WO2013013816A1 (en) | 2011-07-26 | 2013-01-31 | Grünenthal GmbH | Substituted bicyclic aromatic carboxamide and urea derivatives as vanilloid receptor ligands |
| AU2012308243B2 (en) * | 2011-09-15 | 2017-09-14 | Taipei Medical University | Use of indolyl and indolinyl hydroxamates for treating heart failure of neuronal injury |
| AR088701A1 (es) | 2011-11-09 | 2014-06-25 | Gruenenthal Gmbh | Derivados de carboxamida y urea basados en pirazolilo, sustituidos, que contienen una porcion fenilo sustituida con un grupo que contiene n como ligandos del receptor de vanilloide |
| EP2776424A1 (en) | 2011-11-09 | 2014-09-17 | Grünenthal GmbH | Substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an n-cyclic group as vanilloid receptor ligands |
| IN2014KN00865A (cg-RX-API-DMAC10.html) | 2011-11-09 | 2015-10-02 | Gruenenthal Gmbh | |
| EP2776400A1 (en) | 2011-11-09 | 2014-09-17 | Grünenthal GmbH | Substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with a co-containing group as vanilloid receptor ligands |
| IN2014KN00849A (cg-RX-API-DMAC10.html) * | 2011-11-09 | 2015-10-02 | Gruenenthal Gmbh | |
| WO2014149139A2 (en) | 2013-03-15 | 2014-09-25 | Verseon, Inc. | Halogenopyrazoles as inhibitors of thrombin |
| DK2968297T3 (en) | 2013-03-15 | 2019-01-07 | Verseon Inc | MULTI-SUBSTITUTED AROMATIC COMPOUNDS AS SERINE PROTEASE INHIBITORS |
| CN103787895A (zh) * | 2014-01-23 | 2014-05-14 | 安徽华润涂料有限公司 | 一种4-溴-2-甲基苯胺合成的生产工艺 |
| JP2017528486A (ja) | 2014-09-17 | 2017-09-28 | ヴァーセオン コーポレイション | セリンプロテアーゼ阻害剤としてのピラゾリル置換ピリドン化合物 |
| JP6822145B2 (ja) | 2015-01-13 | 2021-01-27 | 日産化学株式会社 | 反応混合物中のスズ化合物の処理方法 |
| ES2931460T3 (es) | 2015-02-27 | 2022-12-29 | Verseon Int Corporation | Compuestos de pirazol sustituido como inhibidores de serina proteasa |
| HUE057041T2 (hu) | 2015-07-06 | 2022-04-28 | Alkermes Inc | Hiszton deacetiláz hetero-halogén gátlói |
| WO2017007755A1 (en) | 2015-07-06 | 2017-01-12 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| EP3130590A1 (en) * | 2015-08-13 | 2017-02-15 | Grünenthal GmbH | Aromatic aza compounds as vr1/trpv1 ligands |
| MX2018009633A (es) | 2016-02-09 | 2018-12-17 | Inventisbio Inc | Inhibidor de indoleamina-2,3-dioxigenasa (ido). |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CN107805221A (zh) * | 2016-09-09 | 2018-03-16 | 西华大学 | 一种制备1h‑吲唑衍生物的方法 |
| CN110139862B (zh) * | 2016-11-03 | 2024-01-16 | 百时美施贵宝公司 | 可用作romk通道抑制剂的经取代的二环杂环衍生物 |
| HRP20220223T1 (hr) | 2017-01-11 | 2022-04-29 | Alkermes, Inc. | Biciklički inhibitori histon deacetilaze |
| WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
| US11225475B2 (en) | 2017-08-07 | 2022-01-18 | Alkermes, Inc. | Substituted pyridines as inhibitors of histone deacetylase |
| CN110627683A (zh) * | 2018-06-25 | 2019-12-31 | 广东东阳光药业有限公司 | 一种茚满酮中间体的制备方法 |
| CN112409191A (zh) * | 2019-08-23 | 2021-02-26 | 持田制药株式会社 | 光学活性的氨基醇的制备方法 |
| WO2021039023A1 (ja) * | 2019-08-23 | 2021-03-04 | 持田製薬株式会社 | ヘテロシクリデンアセトアミド誘導体の製造方法 |
| CN110563693B (zh) * | 2019-09-30 | 2022-10-21 | 苏州弘森药业股份有限公司 | 一种胡椒环制备方法 |
| CN115197146A (zh) * | 2021-04-13 | 2022-10-18 | 西格莱(苏州)生物医药有限公司 | 吲唑类化合物的制备方法 |
| US20260009142A1 (en) | 2022-07-11 | 2026-01-08 | Bayer Ag | Electrochemical synthesis of pyrazolines and pyrazoles |
| CN115282134B (zh) * | 2022-07-20 | 2023-06-23 | 天津中医药大学 | 辣椒素在制备治疗脆性x染色体综合征的药物中的应用 |
| EP4703351A1 (en) * | 2023-04-25 | 2026-03-04 | JW Pharmaceutical Corporation | Method of preparing 4-aminoindan and method of preparing dihydroindenyl-pyrazolo[3,4-b]pyridine-amine compound |
| CN117304009A (zh) * | 2023-10-10 | 2023-12-29 | 韶远科技（上海)有限公司 | 一种3-氟-4-甲基-8-氧代-5,6,7,8-四氢萘的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008059370A2 (en) * | 2006-11-17 | 2008-05-22 | Pfizer Japan Inc. | Substituted bicyclocarboxyamide compounds |
| TW200833663A (en) * | 2006-12-21 | 2008-08-16 | Astrazeneca Ab | Therapeutic agents |
| WO2008137102A2 (en) * | 2007-05-04 | 2008-11-13 | Torreypines Therapeutics, Inc. | Methods of modulating amyloid beta and compounds useful therefor |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR230994A1 (es) | 1981-08-31 | 1984-08-31 | Pfizer | Procedimiento para preparar compuesto de 3'-substituido-5'-(2-amino-4-piridil)-1',2',4'-triazol |
| JPH06157469A (ja) | 1992-11-13 | 1994-06-03 | Ube Ind Ltd | ピラゾールカルボニルウレア誘導体、その製法及び有害生物防除剤 |
| US6455559B1 (en) | 2001-07-19 | 2002-09-24 | Pharmacia Italia S.P.A. | Phenylacetamido-pyrazole derivatives, process for their preparation and their use as antitumor agents |
| GB0206876D0 (en) * | 2002-03-22 | 2002-05-01 | Merck Sharp & Dohme | Therapeutic agents |
| EP1497270A4 (en) * | 2002-03-27 | 2006-01-04 | Smithkline Beecham Corp | AMID COMPOUNDS AND METHOD FOR THEIR USE |
| WO2005004810A2 (en) | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Arylsulfonamide derivatives |
| WO2005048953A2 (en) | 2003-11-13 | 2005-06-02 | Ambit Biosciences Corporation | Amide derivatives as kinase modulators |
| US7838524B2 (en) | 2004-04-30 | 2010-11-23 | Bayer Healthcare Llc | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
| DE102005037499A1 (de) | 2005-08-09 | 2007-02-15 | Merck Patent Gmbh | Pyrazolderivate |
| JP2009518298A (ja) | 2005-12-01 | 2009-05-07 | バイエル ヘルスケア リミティド ライアビリティ カンパニー | 癌治療に有用な尿素化合物 |
| BRPI0713187A2 (pt) * | 2006-07-20 | 2012-10-16 | Mehmet Kahraman | método de inibir rho-quinase, método de tratamento de doença mediada por rho-quinase, composto e composição farmacêutica |
| JP2010083763A (ja) * | 2008-09-29 | 2010-04-15 | Mitsui Chemicals Inc | ピラゾール誘導体およびその製造方法、ならびに殺菌剤 |
-
2010
- 2010-05-06 PL PL10720996T patent/PL2427436T3/pl unknown
- 2010-05-06 PT PT107209967T patent/PT2427436E/pt unknown
- 2010-05-06 WO PCT/EP2010/002785 patent/WO2010127855A1/en not_active Ceased
- 2010-05-06 ES ES10720996T patent/ES2402805T3/es active Active
- 2010-05-06 US US12/775,155 patent/US8334315B2/en not_active Expired - Fee Related
- 2010-05-06 BR BRPI1011192A patent/BRPI1011192A2/pt not_active IP Right Cessation
- 2010-05-06 HR HRP20130128AT patent/HRP20130128T1/hr unknown
- 2010-05-06 AR ARP100101548A patent/AR076753A1/es unknown
- 2010-05-06 DK DK10720996.7T patent/DK2427436T3/da active
- 2010-05-06 TW TW099114463A patent/TWI504589B/zh not_active IP Right Cessation
- 2010-05-06 CA CA2758289A patent/CA2758289A1/en not_active Abandoned
- 2010-05-06 SI SI201030151T patent/SI2427436T1/sl unknown
- 2010-05-06 EP EP10720996A patent/EP2427436B1/en not_active Not-in-force
- 2010-05-06 MX MX2011011800A patent/MX2011011800A/es active IP Right Grant
- 2010-05-06 AU AU2010244684A patent/AU2010244684B2/en not_active Ceased
- 2010-05-06 JP JP2012508950A patent/JP5767631B2/ja not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008059370A2 (en) * | 2006-11-17 | 2008-05-22 | Pfizer Japan Inc. | Substituted bicyclocarboxyamide compounds |
| TW200833663A (en) * | 2006-12-21 | 2008-08-16 | Astrazeneca Ab | Therapeutic agents |
| WO2008137102A2 (en) * | 2007-05-04 | 2008-11-13 | Torreypines Therapeutics, Inc. | Methods of modulating amyloid beta and compounds useful therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| PT2427436E (pt) | 2013-03-04 |
| EP2427436B1 (en) | 2013-01-09 |
| HRP20130128T1 (hr) | 2013-03-31 |
| SI2427436T1 (sl) | 2013-04-30 |
| JP2012526061A (ja) | 2012-10-25 |
| PL2427436T3 (pl) | 2013-06-28 |
| EP2427436A1 (en) | 2012-03-14 |
| JP5767631B2 (ja) | 2015-08-19 |
| WO2010127855A1 (en) | 2010-11-11 |
| MX2011011800A (es) | 2012-01-27 |
| BRPI1011192A2 (pt) | 2016-03-15 |
| US20110003795A1 (en) | 2011-01-06 |
| CA2758289A1 (en) | 2010-11-11 |
| AU2010244684A1 (en) | 2011-11-03 |
| AU2010244684B2 (en) | 2014-07-03 |
| US8334315B2 (en) | 2012-12-18 |
| TW201120010A (en) | 2011-06-16 |
| AR076753A1 (es) | 2011-07-06 |
| DK2427436T3 (da) | 2013-04-02 |
| ES2402805T3 (es) | 2013-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI491595B (zh) | 作為香草類化合物受體之配體之經取代苯基尿素及苯基醯胺 | |
| JP5767631B2 (ja) | バニロイド受容体リガンドとしての置換された芳香族カルボキサミドおよび尿素誘導体 | |
| US8598355B2 (en) | Amide compound | |
| TW201305139A (zh) | 作為類香草素受體配體之經取代雜芳基甲醯胺及尿素衍生物 | |
| US9624215B2 (en) | Amine derivative or salt thereof | |
| US9937158B2 (en) | Benzoheterocyclic compounds and use thereof | |
| EP2460787A1 (en) | Amide compounds and their use as PGE2 antagonists. | |
| JP2009501236A (ja) | ヒストンデアセチラーゼ阻害剤 | |
| JP2013534229A (ja) | バニロイド受容体リガンドとしての置換された環状カルボキサミド誘導体および尿素誘導体 | |
| EA008801B1 (ru) | Получение арилалкилкарбаматных производных и их применение в терапии | |
| CN101563322A (zh) | 用作ppar调节剂的1h-吲哚-2-甲酸衍生物 | |
| US9029378B2 (en) | Substituted bicyclic aromatic carboxamide and urea compounds as vanilloid receptor ligands | |
| US20090275628A1 (en) | Substituted Spiro-Compounds And The Use Thereof For Producing Medicaments | |
| TW201302712A (zh) | 作為類香草素受體配體之經取代雙環甲醯胺及尿素衍生物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |