ZA200507634B - Use of pyridin-2-ylmethylamine derivatives for theproduction of a medicament for the treatment of c hronic pain symptoms of neuropathological or psychogenic origin - Google Patents
Use of pyridin-2-ylmethylamine derivatives for theproduction of a medicament for the treatment of c hronic pain symptoms of neuropathological or psychogenic origin Download PDFInfo
- Publication number
- ZA200507634B ZA200507634B ZA200507634A ZA200507634A ZA200507634B ZA 200507634 B ZA200507634 B ZA 200507634B ZA 200507634 A ZA200507634 A ZA 200507634A ZA 200507634 A ZA200507634 A ZA 200507634A ZA 200507634 B ZA200507634 B ZA 200507634B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- pain
- radical
- amino
- atom
- Prior art date
Links
- 208000002193 Pain Diseases 0.000 title claims abstract description 95
- 230000001107 psychogenic effect Effects 0.000 title claims abstract description 20
- 230000002981 neuropathic effect Effects 0.000 title claims abstract description 17
- 208000024891 symptom Diseases 0.000 title claims abstract description 16
- 239000003814 drug Substances 0.000 title claims abstract description 15
- 230000036407 pain Effects 0.000 title abstract description 68
- 238000011282 treatment Methods 0.000 title abstract description 56
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical class NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 title 1
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 28
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 5
- 239000011707 mineral Substances 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 62
- -1 alkyl radical Chemical class 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 16
- 229940079593 drug Drugs 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000009109 curative therapy Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 230000003449 preventive effect Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 claims description 2
- 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 claims description 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 2
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 2
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 2
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 2
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
- 239000002699 waste material Substances 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 abstract description 32
- 230000036592 analgesia Effects 0.000 abstract description 25
- 230000000694 effects Effects 0.000 abstract description 19
- 230000003902 lesion Effects 0.000 abstract description 14
- 208000004296 neuralgia Diseases 0.000 abstract description 12
- 208000021722 neuropathic pain Diseases 0.000 abstract description 12
- 238000012360 testing method Methods 0.000 abstract description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- QBELHBBOLZORGR-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-2-[[(5-methylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=CC(C)=CC=C1CNCC1N(C(=O)C=2C=C(Cl)C(F)=CC=2)CCC(F)C1 QBELHBBOLZORGR-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract 1
- 241000700159 Rattus Species 0.000 abstract 1
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- SWKAGCAGUZJGSS-UHFFFAOYSA-N phenyl-[4-[(pyridin-2-ylmethylamino)methyl]piperidin-1-yl]methanone Chemical class C=1C=CC=CC=1C(=O)N(CC1)CCC1CNCC1=CC=CC=N1 SWKAGCAGUZJGSS-UHFFFAOYSA-N 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000000018 receptor agonist Substances 0.000 abstract 1
- 229940044601 receptor agonist Drugs 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 description 19
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 17
- 239000000730 antalgic agent Substances 0.000 description 15
- 230000001684 chronic effect Effects 0.000 description 12
- 230000009471 action Effects 0.000 description 11
- 230000000638 stimulation Effects 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229960005181 morphine Drugs 0.000 description 8
- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 description 6
- 229940035676 analgesics Drugs 0.000 description 6
- 229960000794 baclofen Drugs 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 208000001640 Fibromyalgia Diseases 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 208000026935 allergic disease Diseases 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000009610 hypersensitivity Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 210000004209 hair Anatomy 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- 208000004454 Hyperalgesia Diseases 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- 230000036441 nociceptive stimulation Effects 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 208000033808 peripheral neuropathy Diseases 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000002636 symptomatic treatment Methods 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- 206010019233 Headaches Diseases 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- 208000000114 Pain Threshold Diseases 0.000 description 2
- 208000004983 Phantom Limb Diseases 0.000 description 2
- 208000004550 Postoperative Pain Diseases 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 208000003443 Unconsciousness Diseases 0.000 description 2
- 206010053552 allodynia Diseases 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- 230000002996 emotional effect Effects 0.000 description 2
- 206010016256 fatigue Diseases 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical class CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 2
- 201000001119 neuropathy Diseases 0.000 description 2
- 230000007823 neuropathy Effects 0.000 description 2
- 230000037040 pain threshold Effects 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 210000001428 peripheral nervous system Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- VLPIATFUUWWMKC-SNVBAGLBSA-N (2r)-1-(2,6-dimethylphenoxy)propan-2-amine Chemical compound C[C@@H](N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-SNVBAGLBSA-N 0.000 description 1
- SPQWTMZQAGLHOX-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-[[(6-fluoropyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound FC1=CC=CC(CNCC2CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 SPQWTMZQAGLHOX-UHFFFAOYSA-N 0.000 description 1
- TXLLMBFXXGBJFH-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-[[(6-imidazol-1-ylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1CCC(CNCC=2N=C(C=CC=2)N2C=NC=C2)CC1 TXLLMBFXXGBJFH-UHFFFAOYSA-N 0.000 description 1
- WROWADQWIRVOEP-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-[[(6-methylsulfanylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound CSC1=CC=CC(CNCC2CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 WROWADQWIRVOEP-UHFFFAOYSA-N 0.000 description 1
- ONVWLRZNLPURPS-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-[[(6-pyrazol-1-ylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1CCC(CNCC=2N=C(C=CC=2)N2N=CC=C2)CC1 ONVWLRZNLPURPS-UHFFFAOYSA-N 0.000 description 1
- LFPSRLUYDXHPCX-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-[[(6-pyrrol-1-ylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1CCC(CNCC=2N=C(C=CC=2)N2C=CC=C2)CC1 LFPSRLUYDXHPCX-UHFFFAOYSA-N 0.000 description 1
- CKSMNIPCJNWJND-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-[[(6-thiophen-2-ylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1CCC(CNCC=2N=C(C=CC=2)C=2SC=CC=2)CC1 CKSMNIPCJNWJND-UHFFFAOYSA-N 0.000 description 1
- NTCYZWZXRNJMAE-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-[[[6-(1,3-thiazol-2-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1CCC(CNCC=2N=C(C=CC=2)C=2SC=CN=2)CC1 NTCYZWZXRNJMAE-UHFFFAOYSA-N 0.000 description 1
- KSZMCVDTZBUUIA-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-[[[6-(furan-2-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1CCC(CNCC=2N=C(C=CC=2)C=2OC=CC=2)CC1 KSZMCVDTZBUUIA-UHFFFAOYSA-N 0.000 description 1
- IARSIFGESCFKQY-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[(5-methylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=CC(C)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CC1 IARSIFGESCFKQY-UHFFFAOYSA-N 0.000 description 1
- WMXTUBZKRKRZBU-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[(6-fluoropyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound FC1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 WMXTUBZKRKRZBU-UHFFFAOYSA-N 0.000 description 1
- DNSZTEYKWCCSTD-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[(6-methoxypyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound COC1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 DNSZTEYKWCCSTD-UHFFFAOYSA-N 0.000 description 1
- RIGJMEXZMQNBKZ-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[(6-pyrazol-1-ylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1CN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CCC1(F)CNCC(N=1)=CC=CC=1N1C=CC=N1 RIGJMEXZMQNBKZ-UHFFFAOYSA-N 0.000 description 1
- ADGCARVTPQCUGH-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[(6-thiophen-2-ylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1CN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CCC1(F)CNCC(N=1)=CC=CC=1C1=CC=CS1 ADGCARVTPQCUGH-UHFFFAOYSA-N 0.000 description 1
- IWSQYCLFGIYRMU-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[[6-(1,3-oxazol-5-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1CN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CCC1(F)CNCC(N=1)=CC=CC=1C1=CN=CO1 IWSQYCLFGIYRMU-UHFFFAOYSA-N 0.000 description 1
- NYFVZSBKYHXQCT-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[[6-(1,3-thiazol-2-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1CN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CCC1(F)CNCC(N=1)=CC=CC=1C1=NC=CS1 NYFVZSBKYHXQCT-UHFFFAOYSA-N 0.000 description 1
- MWDFFRURRYIQMB-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[[6-(1-methylpyrazol-3-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound CN1C=CC(C=2N=C(CNCC3(F)CCN(CC3)C(=O)C=3C=C(Cl)C(Cl)=CC=3)C=CC=2)=N1 MWDFFRURRYIQMB-UHFFFAOYSA-N 0.000 description 1
- UTIFBMOIOKNYIT-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[[6-(1h-pyrazol-5-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1CN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CCC1(F)CNCC(N=1)=CC=CC=1C=1C=CNN=1 UTIFBMOIOKNYIT-UHFFFAOYSA-N 0.000 description 1
- GKQHLLOQAMECJU-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[[6-(fluoromethyl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound FCC1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 GKQHLLOQAMECJU-UHFFFAOYSA-N 0.000 description 1
- RJKIATOONRELLI-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[[6-(furan-2-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1CN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CCC1(F)CNCC(N=1)=CC=CC=1C1=CC=CO1 RJKIATOONRELLI-UHFFFAOYSA-N 0.000 description 1
- ZKDQXTANHABPRI-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[[6-(furan-3-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1CN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CCC1(F)CNCC(N=1)=CC=CC=1C=1C=COC=1 ZKDQXTANHABPRI-UHFFFAOYSA-N 0.000 description 1
- NDYWHACDLHAKHK-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[[6-(methylamino)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound CNC1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 NDYWHACDLHAKHK-UHFFFAOYSA-N 0.000 description 1
- UJWLUMAAOUJRIN-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-[[[6-(diethylamino)pyridin-2-yl]methylamino]methyl]-4-fluoropiperidin-1-yl]methanone Chemical compound CCN(CC)C1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(F)=CC=2)=N1 UJWLUMAAOUJRIN-UHFFFAOYSA-N 0.000 description 1
- ATPFLJYVAXSNHV-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-[[[6-(dimethylamino)-4-methylpyridin-2-yl]methylamino]methyl]-4-fluoropiperidin-1-yl]methanone Chemical compound CN(C)C1=CC(C)=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(F)=CC=2)=N1 ATPFLJYVAXSNHV-UHFFFAOYSA-N 0.000 description 1
- KTNPWLGBAAFMNK-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-[[[6-(dimethylamino)pyridin-2-yl]methylamino]methyl]-4-fluoropiperidin-1-yl]methanone Chemical compound CN(C)C1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(F)=CC=2)=N1 KTNPWLGBAAFMNK-UHFFFAOYSA-N 0.000 description 1
- DGXPRFFOVPWQOE-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-[[[6-(ethylamino)pyridin-2-yl]methylamino]methyl]-4-fluoropiperidin-1-yl]methanone Chemical compound CCNC1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(F)=CC=2)=N1 DGXPRFFOVPWQOE-UHFFFAOYSA-N 0.000 description 1
- VTOWCNHGZNRYSU-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[(5-methyl-6-pyrazol-1-ylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=C(N2N=CC=C2)C(C)=CC=C1CNCC(CC1)(F)CCN1C(=O)C1=CC=C(F)C(Cl)=C1 VTOWCNHGZNRYSU-UHFFFAOYSA-N 0.000 description 1
- WGGCKIOKOAQRNS-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[(6-pyrazol-1-ylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound C1=C(Cl)C(F)=CC=C1C(=O)N1CCC(F)(CNCC=2N=C(C=CC=2)N2N=CC=C2)CC1 WGGCKIOKOAQRNS-UHFFFAOYSA-N 0.000 description 1
- YDAKHFOEDZWMLA-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[[6-(furan-2-yl)-5-methylpyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=C(C=2OC=CC=2)C(C)=CC=C1CNCC(CC1)(F)CCN1C(=O)C1=CC=C(F)C(Cl)=C1 YDAKHFOEDZWMLA-UHFFFAOYSA-N 0.000 description 1
- BGKIREVCNUFEMA-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[[6-(methylamino)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound CNC1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(F)=CC=2)=N1 BGKIREVCNUFEMA-UHFFFAOYSA-N 0.000 description 1
- ZVOKHVDANBFMRT-UHFFFAOYSA-N (3-chloro-4-methylphenyl)-[4-[[[6-(dimethylamino)pyridin-2-yl]methylamino]methyl]-4-fluoropiperidin-1-yl]methanone Chemical compound CN(C)C1=CC=CC(CNCC2(F)CCN(CC2)C(=O)C=2C=C(Cl)C(C)=CC=2)=N1 ZVOKHVDANBFMRT-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- JHVHEDNLONERHY-UHFFFAOYSA-N 2-(2-chloro-5-methylsulfanylphenyl)-1-methyl-1-(3-methylsulfanylphenyl)guanidine Chemical compound CSC1=CC=CC(N(C)C(N)=NC=2C(=CC=C(SC)C=2)Cl)=C1 JHVHEDNLONERHY-UHFFFAOYSA-N 0.000 description 1
- IFZZDINNCWFGEO-UHFFFAOYSA-N 2-propan-2-yloxypyridine Chemical compound CC(C)OC1=CC=CC=N1 IFZZDINNCWFGEO-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- UCTWMZQNUQWSLP-UHFFFAOYSA-N Adrenaline Natural products CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010016059 Facial pain Diseases 0.000 description 1
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 1
- 229940122459 Glutamate antagonist Drugs 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- 208000004044 Hypesthesia Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 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 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- VTGBZWHPJFMTKS-UHFFFAOYSA-N N-(4-amino-2-methyl-6-quinolinyl)-2-[(4-ethylphenoxy)methyl]benzamide Chemical compound C1=CC(CC)=CC=C1OCC1=CC=CC=C1C(=O)NC1=CC=C(N=C(C)C=C2N)C2=C1 VTGBZWHPJFMTKS-UHFFFAOYSA-N 0.000 description 1
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 1
- 102000048266 Nociceptin Human genes 0.000 description 1
- 108090000622 Nociceptin Proteins 0.000 description 1
- 206010056238 Phantom pain Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010040030 Sensory loss Diseases 0.000 description 1
- 206010040108 Serotonin syndrome Diseases 0.000 description 1
- 241000772296 Terebrantes Species 0.000 description 1
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- ZUIIRJOZQKJSMP-UHFFFAOYSA-N [4-[[(4-chloropyridin-2-yl)methylamino]methyl]piperidin-1-yl]-(3,4-dichlorophenyl)methanone Chemical compound ClC1=CC=NC(CNCC2CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 ZUIIRJOZQKJSMP-UHFFFAOYSA-N 0.000 description 1
- KHFLBIVINQTEPJ-UHFFFAOYSA-N [4-[[(6-cyclopentyloxypyridin-2-yl)methylamino]methyl]piperidin-1-yl]-(3,4-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1CCC(CNCC=2N=C(OC3CCCC3)C=CC=2)CC1 KHFLBIVINQTEPJ-UHFFFAOYSA-N 0.000 description 1
- DOICMSZGRIYFQO-UHFFFAOYSA-N [4-[[(6-cyclopropylpyridin-2-yl)methylamino]methyl]-4-fluoropiperidin-1-yl]-(3,4-dichlorophenyl)methanone Chemical compound C1CN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CCC1(F)CNCC(N=1)=CC=CC=1C1CC1 DOICMSZGRIYFQO-UHFFFAOYSA-N 0.000 description 1
- LNIQZQYUYOSMFT-UHFFFAOYSA-N [4-[[[6-(azetidin-1-yl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]-(3,4-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1CCC(CNCC=2N=C(C=CC=2)N2CCC2)CC1 LNIQZQYUYOSMFT-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229940102884 adrenalin Drugs 0.000 description 1
- 239000003194 amino acid receptor blocking agent Substances 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- PKZXLMVXBZICTF-UHFFFAOYSA-N befiradol Chemical compound N1=CC(C)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(Cl)C(F)=CC=2)CC1 PKZXLMVXBZICTF-UHFFFAOYSA-N 0.000 description 1
- 229930003827 cannabinoid Natural products 0.000 description 1
- 239000003557 cannabinoid Substances 0.000 description 1
- 229940065144 cannabinoids Drugs 0.000 description 1
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical class COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000000064 cholinergic agonist Substances 0.000 description 1
- 208000022371 chronic pain syndrome Diseases 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- NFHRQQKPEBFUJK-HSZRJFAPSA-N devazepide Chemical compound O=C([C@@H](NC(=O)C=1NC2=CC=CC=C2C=1)N=1)N(C)C2=CC=CC=C2C=1C1=CC=CC=C1 NFHRQQKPEBFUJK-HSZRJFAPSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 229960002870 gabapentin Drugs 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 208000034783 hypoesthesia Diseases 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 description 1
- 229960004002 levetiracetam Drugs 0.000 description 1
- HPHUVLMMVZITSG-ZCFIWIBFSA-N levetiracetam Chemical compound CC[C@H](C(N)=O)N1CCCC1=O HPHUVLMMVZITSG-ZCFIWIBFSA-N 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 1
- 229960004640 memantine Drugs 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229960003404 mexiletine Drugs 0.000 description 1
- 229960005195 morphine hydrochloride Drugs 0.000 description 1
- XELXKCKNPPSFNN-BJWPBXOKSA-N morphine hydrochloride trihydrate Chemical compound O.O.O.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XELXKCKNPPSFNN-BJWPBXOKSA-N 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- PULGYDLMFSFVBL-SMFNREODSA-N nociceptin Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)[C@@H](C)O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 PULGYDLMFSFVBL-SMFNREODSA-N 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- MKTAGSRKQIGEBH-SSDOTTSWSA-N tebanicline Chemical compound C1=NC(Cl)=CC=C1OC[C@@H]1NCC1 MKTAGSRKQIGEBH-SSDOTTSWSA-N 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 229960004394 topiramate Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0303099A FR2852244B1 (fr) | 2003-03-13 | 2003-03-13 | Utilisation de derives de pyridin-2-yl-methylamine pour la preparation d'un medicament destine au traitement des symptomes de la douleur chronique d'origine neuropathique ou psychogene |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200507634B true ZA200507634B (en) | 2006-06-28 |
Family
ID=32893267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200507634A ZA200507634B (en) | 2003-03-13 | 2005-09-21 | Use of pyridin-2-ylmethylamine derivatives for theproduction of a medicament for the treatment of c hronic pain symptoms of neuropathological or psychogenic origin |
Country Status (25)
Country | Link |
---|---|
US (1) | US8609694B2 (ko) |
EP (1) | EP1603564B1 (ko) |
JP (1) | JP4684994B2 (ko) |
KR (1) | KR101100002B1 (ko) |
CN (1) | CN1761467B (ko) |
AT (1) | ATE366111T1 (ko) |
AU (1) | AU2004222051B2 (ko) |
BR (1) | BRPI0408293A (ko) |
CA (1) | CA2518591C (ko) |
CY (1) | CY1106900T1 (ko) |
DE (1) | DE602004007364T2 (ko) |
DK (1) | DK1603564T3 (ko) |
ES (1) | ES2289494T3 (ko) |
FR (1) | FR2852244B1 (ko) |
HK (1) | HK1079120A1 (ko) |
IL (1) | IL170743A (ko) |
MX (1) | MXPA05009782A (ko) |
NO (1) | NO334997B1 (ko) |
NZ (1) | NZ542461A (ko) |
PL (1) | PL1603564T3 (ko) |
PT (1) | PT1603564E (ko) |
RU (1) | RU2359674C2 (ko) |
UA (1) | UA81023C2 (ko) |
WO (1) | WO2004083171A2 (ko) |
ZA (1) | ZA200507634B (ko) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8071778B2 (en) | 2006-07-27 | 2011-12-06 | Bristol-Myers Squibb Company | Substituted heterocyclic ethers and their use in CNS disorders |
WO2009096941A1 (en) * | 2008-01-28 | 2009-08-06 | Bristol-Myers Squibb Company | Substituted heterocyclic ethers and their use in cns disorders |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996021661A1 (en) | 1995-01-12 | 1996-07-18 | Glaxo Group Limited | Piperidine derivatives having tachykinin antagonist activity |
FR2755967B1 (fr) * | 1996-11-21 | 1999-01-29 | Pf Medicament | Derives de la pyridin-2-yl-methylamine, leur procede de preparation et leur application comme medicaments |
FR2784378B1 (fr) * | 1998-10-09 | 2000-12-29 | Pf Medicament | Nouveaux derives d'aryl-(4-fluoro-4-[(2-pyridin-2-yl- ethylamino)-methyl]-piperidin-1-yl)-methanone, leur procede de preparation et leur utilisation a titre de medicaments |
FR2840900B1 (fr) * | 2002-06-18 | 2005-02-25 | Pf Medicament | Nouveaux derives d'aryl[4-halogeno-4- [(heteroaryl-methylamino)-methyl]-piperidin-1-yl]-methanone, leur procede de preparation et leur utilisation a titre de medicaments |
-
2003
- 2003-03-13 FR FR0303099A patent/FR2852244B1/fr not_active Expired - Fee Related
-
2004
- 2004-03-15 CA CA2518591A patent/CA2518591C/fr not_active Expired - Lifetime
- 2004-03-15 WO PCT/FR2004/000630 patent/WO2004083171A2/fr active IP Right Grant
- 2004-03-15 KR KR1020057017151A patent/KR101100002B1/ko active IP Right Grant
- 2004-03-15 DK DK04720637T patent/DK1603564T3/da active
- 2004-03-15 BR BRPI0408293-1A patent/BRPI0408293A/pt not_active Application Discontinuation
- 2004-03-15 AU AU2004222051A patent/AU2004222051B2/en not_active Ceased
- 2004-03-15 NZ NZ542461A patent/NZ542461A/en not_active IP Right Cessation
- 2004-03-15 DE DE602004007364T patent/DE602004007364T2/de not_active Expired - Lifetime
- 2004-03-15 PL PL04720637T patent/PL1603564T3/pl unknown
- 2004-03-15 RU RU2005131615/15A patent/RU2359674C2/ru not_active IP Right Cessation
- 2004-03-15 EP EP04720637A patent/EP1603564B1/fr not_active Expired - Lifetime
- 2004-03-15 MX MXPA05009782A patent/MXPA05009782A/es active IP Right Grant
- 2004-03-15 US US10/549,076 patent/US8609694B2/en active Active
- 2004-03-15 PT PT04720637T patent/PT1603564E/pt unknown
- 2004-03-15 ES ES04720637T patent/ES2289494T3/es not_active Expired - Lifetime
- 2004-03-15 CN CN2004800068827A patent/CN1761467B/zh not_active Expired - Lifetime
- 2004-03-15 AT AT04720637T patent/ATE366111T1/de active
- 2004-03-15 JP JP2006505728A patent/JP4684994B2/ja not_active Expired - Lifetime
- 2004-03-15 UA UAA200509594A patent/UA81023C2/uk unknown
-
2005
- 2005-09-08 IL IL170743A patent/IL170743A/en not_active IP Right Cessation
- 2005-09-21 ZA ZA200507634A patent/ZA200507634B/en unknown
- 2005-10-11 NO NO20054673A patent/NO334997B1/no not_active IP Right Cessation
-
2006
- 2006-01-24 HK HK06101061A patent/HK1079120A1/xx not_active IP Right Cessation
-
2007
- 2007-10-02 CY CY20071101255T patent/CY1106900T1/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2012258219B2 (en) | Use of sigma ligands in diabetes type-2 associated pain | |
KR101825972B1 (ko) | 운동 장애 치료를 위한 세로토닌 수용체 작용제의 조합 | |
JP2002538176A (ja) | トラマドール物質および選択的cox−2阻害薬を含んで成る組成物 | |
TWI629984B (zh) | σ配體在與間質性膀胱炎/膀胱疼痛綜合徵(IC/BPS)相關的疼痛的預防和治療中的應用 | |
NO335245B1 (no) | Anvendelse av alfa-aminoamidderivater med antiinflammatorisk aktivitet for fremstilling av medikamenter | |
WO2021231905A1 (en) | Ketamine treatment for amyotrophic lateral sclerosis | |
ZA200507634B (en) | Use of pyridin-2-ylmethylamine derivatives for theproduction of a medicament for the treatment of c hronic pain symptoms of neuropathological or psychogenic origin | |
JP2017514884A (ja) | 医療用の(r)−ピルリンドールおよびその薬学的に許容可能な塩 | |
US20140094446A1 (en) | Cyclic Amino Acids for the Treatment of Pain | |
KR20200103042A (ko) | 세페타프로스트와 Rho 키나아제 저해제의 조합 의약 | |
US11191758B2 (en) | Use of selective serotonin 5-HT1A receptor agonists for treating side-effects of VMAT inhibitors | |
KR20180010475A (ko) | Trpc3의 억제제를 유효성분으로 포함하는 가려움증 치료용 약제학적 조성물 | |
KR20090002888A (ko) | 파킨슨씨 병을 포함한 뇌신경질환 치료효과 및 뇌보호효과를 갖는 치환된 벤젠 유도체 화합물을 포함하는약제학적 조성물 및 상기 화합물을 이용한 뇌질환 치료방법 | |
JP2012250952A (ja) | アデノシン誘導体とRhoキナーゼ阻害剤の組合せ剤 |