JP2008537741A5 - - Google Patents
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- Publication number
- JP2008537741A5 JP2008537741A5 JP2008503245A JP2008503245A JP2008537741A5 JP 2008537741 A5 JP2008537741 A5 JP 2008537741A5 JP 2008503245 A JP2008503245 A JP 2008503245A JP 2008503245 A JP2008503245 A JP 2008503245A JP 2008537741 A5 JP2008537741 A5 JP 2008537741A5
- Authority
- JP
- Japan
- Prior art keywords
- triazabicyclo
- trien
- deca
- adamantyl
- acetamide
- 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.)
- Withdrawn
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- -1 amino, cyano, sulfo, sulfanyl Chemical group 0.000 claims 585
- CKBZJTAMRPPVSR-UHFFFAOYSA-N adamantane-1-carboxamide Chemical compound C1C(C2)CC3CC2CC1(C(=O)N)C3 CKBZJTAMRPPVSR-UHFFFAOYSA-N 0.000 claims 217
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 190
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 121
- 150000001875 compounds Chemical class 0.000 claims 47
- 150000003857 carboxamides Chemical class 0.000 claims 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 27
- 239000008194 pharmaceutical composition Substances 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 16
- 208000004296 neuralgia Diseases 0.000 claims 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 15
- 208000002193 Pain Diseases 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 125000002252 acyl group Chemical group 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 11
- 125000001475 halogen functional group Chemical group 0.000 claims 11
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 206010061218 Inflammation Diseases 0.000 claims 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 230000004054 inflammatory process Effects 0.000 claims 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 8
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 7
- 208000023275 Autoimmune disease Diseases 0.000 claims 7
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 208000020925 Bipolar disease Diseases 0.000 claims 6
- 208000014644 Brain disease Diseases 0.000 claims 6
- 208000003251 Pruritus Diseases 0.000 claims 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 208000037765 diseases and disorders Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims 6
- 230000001404 mediated effect Effects 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- 150000003457 sulfones Chemical class 0.000 claims 6
- 150000003462 sulfoxides Chemical class 0.000 claims 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 5
- 206010029240 Neuritis Diseases 0.000 claims 5
- 125000004442 acylamino group Chemical group 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 5
- 208000021722 neuropathic pain Diseases 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 201000008482 osteoarthritis Diseases 0.000 claims 5
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 5
- 208000024891 symptom Diseases 0.000 claims 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 4
- 208000019695 Migraine disease Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 206010043269 Tension headache Diseases 0.000 claims 4
- 208000008548 Tension-Type Headache Diseases 0.000 claims 4
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 150000001540 azides Chemical class 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 4
- 206010015037 epilepsy Diseases 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 238000001727 in vivo Methods 0.000 claims 4
- 208000014674 injury Diseases 0.000 claims 4
- 206010027599 migraine Diseases 0.000 claims 4
- 210000002307 prostate Anatomy 0.000 claims 4
- 208000023504 respiratory system disease Diseases 0.000 claims 4
- 208000004371 toothache Diseases 0.000 claims 4
- 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 claims 3
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 3
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical group ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 claims 3
- 125000002981 3-(trifluoromethyl)benzoyl group Chemical group FC(C=1C=C(C(=O)*)C=CC1)(F)F 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 208000000094 Chronic Pain Diseases 0.000 claims 3
- 208000006561 Cluster Headache Diseases 0.000 claims 3
- 208000030814 Eating disease Diseases 0.000 claims 3
- 208000034347 Faecal incontinence Diseases 0.000 claims 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 3
- 206010019233 Headaches Diseases 0.000 claims 3
- 206010020751 Hypersensitivity Diseases 0.000 claims 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 3
- 206010065390 Inflammatory pain Diseases 0.000 claims 3
- 206010022998 Irritability Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims 3
- 206010046543 Urinary incontinence Diseases 0.000 claims 3
- 206010046851 Uveitis Diseases 0.000 claims 3
- 208000027418 Wounds and injury Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 208000005298 acute pain Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 201000009961 allergic asthma Diseases 0.000 claims 3
- 208000026935 allergic disease Diseases 0.000 claims 3
- 201000010105 allergic rhinitis Diseases 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 208000028683 bipolar I disease Diseases 0.000 claims 3
- 230000036772 blood pressure Effects 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 208000018912 cluster headache syndrome Diseases 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 210000001072 colon Anatomy 0.000 claims 3
- NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 claims 3
- 230000006378 damage Effects 0.000 claims 3
- 235000014632 disordered eating Nutrition 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000004064 dysfunction Effects 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 206010014599 encephalitis Diseases 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 231100000869 headache Toxicity 0.000 claims 3
- 230000009610 hypersensitivity Effects 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 230000007803 itching Effects 0.000 claims 3
- 150000002632 lipids Chemical class 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 208000010125 myocardial infarction Diseases 0.000 claims 3
- 230000000926 neurological effect Effects 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 230000008085 renal dysfunction Effects 0.000 claims 3
- 230000000241 respiratory effect Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 208000020431 spinal cord injury Diseases 0.000 claims 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- 230000000472 traumatic effect Effects 0.000 claims 3
- 210000003932 urinary bladder Anatomy 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- 206010006482 Bronchospasm Diseases 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 208000021965 Glossopharyngeal Nerve disease Diseases 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 208000018569 Respiratory Tract disease Diseases 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 230000007885 bronchoconstriction Effects 0.000 claims 2
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims 2
- 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 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 230000006806 disease prevention Effects 0.000 claims 2
- 206010013990 dysuria Diseases 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 201000005442 glossopharyngeal neuralgia Diseases 0.000 claims 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- IZWHQUZOPBEYKY-AATRIKPKSA-N (e)-3-[4-[[4-[[2-(1-adamantyl)acetyl]amino]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1CN1CC(N=CN=C2NC(=O)CC34CC5CC(CC(C5)C3)C4)=C2CC1 IZWHQUZOPBEYKY-AATRIKPKSA-N 0.000 claims 1
- 125000000980 1H-indol-3-ylmethyl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[*])C2=C1[H] 0.000 claims 1
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims 1
- 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 claims 1
- GXKAVGBEDMNAHX-UHFFFAOYSA-N 2-(1-adamantyl)-n-(7-benzyl-6,8-dihydro-5h-1,7-naphthyridin-4-yl)acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC(C=1CC2)=CC=NC=1CN2CC1=CC=CC=C1 GXKAVGBEDMNAHX-UHFFFAOYSA-N 0.000 claims 1
- RIVCPBYSDNUPTD-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[(4-fluorophenyl)methyl]-1h-isoquinolin-5-yl]acetamide Chemical compound C1=CC(F)=CC=C1CN1C=CC2=C(NC(=O)CC34CC5CC(CC(C5)C3)C4)C=CC=C2C1 RIVCPBYSDNUPTD-UHFFFAOYSA-N 0.000 claims 1
- 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002995 2-(trifluoromethyl)benzoyl group Chemical group FC(C1=C(C(=O)*)C=CC=C1)(F)F 0.000 claims 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000005916 2-methylpentyl group Chemical group 0.000 claims 1
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 206010003399 Arthropod bite Diseases 0.000 claims 1
- ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims 1
- 208000001387 Causalgia Diseases 0.000 claims 1
- 206010008334 Cervicobrachial syndrome Diseases 0.000 claims 1
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims 1
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 1
- 206010020880 Hypertrophy Diseases 0.000 claims 1
- 208000006877 Insect Bites and Stings Diseases 0.000 claims 1
- 206010049949 Intercostal neuralgia Diseases 0.000 claims 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 1
- 208000002472 Morton Neuroma Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 206010068106 Occipital neuralgia Diseases 0.000 claims 1
- 208000004983 Phantom Limb Diseases 0.000 claims 1
- 206010056238 Phantom pain Diseases 0.000 claims 1
- 206010036105 Polyneuropathy Diseases 0.000 claims 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 1
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 claims 1
- 208000008765 Sciatica Diseases 0.000 claims 1
- 206010040744 Sinus headache Diseases 0.000 claims 1
- 208000004078 Snake Bites Diseases 0.000 claims 1
- 208000003589 Spider Bites Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- WLYPBMBWKYALCG-UHFFFAOYSA-N [2,4-bis(trifluoromethyl)phenyl]boronic acid Chemical group OB(O)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F WLYPBMBWKYALCG-UHFFFAOYSA-N 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims 1
- 230000002146 bilateral effect Effects 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 229960002504 capsaicin Drugs 0.000 claims 1
- 235000017663 capsaicin Nutrition 0.000 claims 1
- 230000035606 childbirth Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims 1
- 208000012790 cranial neuralgia Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
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-
2006
- 2006-03-17 US US11/384,199 patent/US7402596B2/en not_active Expired - Fee Related
- 2006-03-17 US US11/384,045 patent/US7297700B2/en not_active Expired - Fee Related
- 2006-03-24 EP EP06739520A patent/EP1865774A4/en not_active Withdrawn
- 2006-03-24 CA CA002602717A patent/CA2602717A1/en not_active Abandoned
- 2006-03-24 WO PCT/US2006/010774 patent/WO2006102588A1/en not_active Ceased
- 2006-03-24 MX MX2007011854A patent/MX2007011854A/es active IP Right Grant
- 2006-03-24 WO PCT/US2006/010880 patent/WO2006102610A2/en not_active Ceased
- 2006-03-24 CA CA002602718A patent/CA2602718A1/en not_active Abandoned
- 2006-03-24 EP EP06739589A patent/EP1860942A4/en not_active Withdrawn
- 2006-03-24 JP JP2008503223A patent/JP2008534511A/ja not_active Withdrawn
- 2006-03-24 JP JP2008503245A patent/JP2008537741A/ja not_active Withdrawn
- 2006-03-24 MX MX2007011855A patent/MX2007011855A/es active IP Right Grant
-
2007
- 2007-07-03 US US11/773,106 patent/US20080039478A1/en not_active Abandoned
-
2008
- 2008-07-16 US US12/218,620 patent/US20090170838A1/en not_active Abandoned
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