UA81051C2 - Use of indazole derivatives for the treatment of neuropathic pain - Google Patents
Use of indazole derivatives for the treatment of neuropathic pain Download PDFInfo
- Publication number
- UA81051C2 UA81051C2 UAA200600307A UAA200600307A UA81051C2 UA 81051 C2 UA81051 C2 UA 81051C2 UA A200600307 A UAA200600307 A UA A200600307A UA A200600307 A UAA200600307 A UA A200600307A UA 81051 C2 UA81051 C2 UA 81051C2
- Authority
- UA
- Ukraine
- Prior art keywords
- compound
- neuropathic pain
- treatment
- formula
- pain
- Prior art date
Links
- 208000004296 neuralgia Diseases 0.000 title abstract description 18
- 208000021722 neuropathic pain Diseases 0.000 title abstract description 15
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 208000002193 Pain Diseases 0.000 claims description 8
- 230000036407 pain Effects 0.000 claims description 3
- 230000002981 neuropathic effect Effects 0.000 claims 1
- 241000700159 Rattus Species 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 208000004454 Hyperalgesia Diseases 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 206010053552 allodynia Diseases 0.000 description 6
- 210000003497 sciatic nerve Anatomy 0.000 description 6
- 208000000094 Chronic Pain Diseases 0.000 description 5
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 5
- 229960001052 streptozocin Drugs 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- 208000000114 Pain Threshold Diseases 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000037040 pain threshold Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 208000035154 Hyperesthesia Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 210000003414 extremity Anatomy 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002641 glycemic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 210000000548 hind-foot Anatomy 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 201000001119 neuropathy Diseases 0.000 description 2
- 230000007823 neuropathy Effects 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 208000033808 peripheral neuropathy Diseases 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ZLJNDKIJSSGTIQ-UHFFFAOYSA-N 1-propan-2-ylindazole Chemical compound C1=CC=C2N(C(C)C)N=CC2=C1 ZLJNDKIJSSGTIQ-UHFFFAOYSA-N 0.000 description 1
- DYYVTFCYVZEQDG-UHFFFAOYSA-N 4-(2-bromoethyl)phenol Chemical compound OC1=CC=C(CCBr)C=C1 DYYVTFCYVZEQDG-UHFFFAOYSA-N 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- 208000017228 Gastrointestinal motility disease Diseases 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000007813 immunodeficiency Effects 0.000 description 1
- -1 indazole compound Chemical class 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000003040 nociceptive effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000014 opioid analgesic Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000037324 pain perception Effects 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 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
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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]
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT001468A ITMI20031468A1 (it) | 2003-07-18 | 2003-07-18 | Farmaco ativo nel dolore neuropatico |
PCT/EP2004/007635 WO2005013989A1 (en) | 2003-07-18 | 2004-07-08 | Use of indazole derivatives for the treatment of neuropathic pain |
Publications (1)
Publication Number | Publication Date |
---|---|
UA81051C2 true UA81051C2 (en) | 2007-11-26 |
Family
ID=34131194
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UAA200600307A UA81051C2 (en) | 2003-07-18 | 2004-08-07 | Use of indazole derivatives for the treatment of neuropathic pain |
Country Status (22)
Country | Link |
---|---|
US (1) | US7638534B2 (zh) |
EP (1) | EP1646387B1 (zh) |
JP (1) | JP4881729B2 (zh) |
KR (1) | KR101073993B1 (zh) |
CN (1) | CN100427089C (zh) |
AR (1) | AR045994A1 (zh) |
AT (1) | ATE345134T1 (zh) |
AU (1) | AU2004262878B2 (zh) |
CA (1) | CA2526052C (zh) |
DE (1) | DE602004003251T2 (zh) |
DK (1) | DK1646387T3 (zh) |
EA (1) | EA008144B1 (zh) |
ES (1) | ES2275232T3 (zh) |
GE (1) | GEP20084343B (zh) |
HK (1) | HK1087026A1 (zh) |
IL (1) | IL172101A (zh) |
IT (1) | ITMI20031468A1 (zh) |
MX (1) | MXPA06000651A (zh) |
PL (1) | PL1646387T3 (zh) |
PT (1) | PT1646387E (zh) |
UA (1) | UA81051C2 (zh) |
WO (1) | WO2005013989A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20062230A1 (it) * | 2006-11-22 | 2008-05-23 | Acraf | Composto 2-alchil-indazolico procedimento per preparalo e composizione farmaceutica che lo comprende |
UA99927C2 (uk) * | 2007-11-12 | 2012-10-25 | Ацьенде Кимике Риуните Анджелини Франческо А.Чи.Р.А.Ф. С.П.А. | Медикамент, який є активним при невропатичному болі |
ES2399066T3 (es) | 2008-07-29 | 2013-03-25 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Compuesto con actividad serotoninérgica, procedimiento para su preparación y composición farmacéutica que lo comprende |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2435092A (en) * | 1991-08-20 | 1993-03-16 | Smithkline Beecham Plc | 5-ht4 receptor antagonists |
ATE182591T1 (de) * | 1991-09-12 | 1999-08-15 | Smithkline Beecham Plc | 5-ht4 rezeptor antagonisten |
MA22647A1 (fr) * | 1991-09-14 | 1993-04-01 | Smithkline Beecham Plc | Procede de preparation d'un ester ou d'un amide d'un nouveau produit . |
GB9120628D0 (en) | 1991-09-27 | 1991-11-06 | Fujisawa Pharmaceutical Co | Pyrrolobenzoxazine derivatives and process for preparation thereof |
NZ249565A (en) | 1992-03-12 | 1997-07-27 | Smithkline Beecham Plc | Hetring[1,2-a]indole-carboxy derivatives |
US5864039A (en) * | 1994-03-30 | 1999-01-26 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzoic acid compounds and use thereof as medicaments |
IL117438A (en) * | 1995-03-16 | 2001-12-23 | Lilly Co Eli | Indazolecarboxamides, their preparation and pharmaceutical compositions containing them |
IT1291569B1 (it) * | 1997-04-15 | 1999-01-11 | Angelini Ricerche Spa | Indazolammidi come agenti serotoninergici |
US6069152A (en) * | 1997-10-07 | 2000-05-30 | Eli Lilly And Company | 5-HT4 agonists and antagonists |
DE10132746A1 (de) * | 2001-07-05 | 2003-02-06 | Gruenenthal Gmbh | Substituierte 1-Phenethylpiperidinverbindungen |
US6624162B2 (en) * | 2001-10-22 | 2003-09-23 | Pfizer Inc. | Imidazopyridine compounds as 5-HT4 receptor modulators |
AU2003255767A1 (en) | 2002-08-10 | 2004-02-25 | Astex Technology Limited | 3-(carbonyl) 1h-indazole compounds as cyclin dependent kinases (cdk) inhibitors |
ITMI20030287A1 (it) * | 2003-02-18 | 2004-08-19 | Acraf | Indazolammidi dotate di attivita' analgesica metodo, per |
ITMI20030972A1 (it) * | 2003-05-15 | 2004-11-16 | Acraf | Indazolo dotato di attivita' analgesica, metodo per prepararlo e composizione farmaceutica che lo comprende. |
-
2003
- 2003-07-18 IT IT001468A patent/ITMI20031468A1/it unknown
-
2004
- 2004-07-08 WO PCT/EP2004/007635 patent/WO2005013989A1/en active IP Right Grant
- 2004-07-08 AU AU2004262878A patent/AU2004262878B2/en not_active Ceased
- 2004-07-08 CN CNB2004800176802A patent/CN100427089C/zh not_active Expired - Fee Related
- 2004-07-08 MX MXPA06000651A patent/MXPA06000651A/es active IP Right Grant
- 2004-07-08 AT AT04763164T patent/ATE345134T1/de active
- 2004-07-08 DK DK04763164T patent/DK1646387T3/da active
- 2004-07-08 US US10/564,854 patent/US7638534B2/en not_active Expired - Fee Related
- 2004-07-08 PT PT04763164T patent/PT1646387E/pt unknown
- 2004-07-08 JP JP2006519845A patent/JP4881729B2/ja not_active Expired - Fee Related
- 2004-07-08 PL PL04763164T patent/PL1646387T3/pl unknown
- 2004-07-08 EP EP04763164A patent/EP1646387B1/en not_active Expired - Lifetime
- 2004-07-08 KR KR1020067000489A patent/KR101073993B1/ko not_active IP Right Cessation
- 2004-07-08 GE GEAP20049234A patent/GEP20084343B/en unknown
- 2004-07-08 CA CA2526052A patent/CA2526052C/en not_active Expired - Fee Related
- 2004-07-08 ES ES04763164T patent/ES2275232T3/es not_active Expired - Lifetime
- 2004-07-08 DE DE602004003251T patent/DE602004003251T2/de not_active Expired - Lifetime
- 2004-07-08 EA EA200600271A patent/EA008144B1/ru not_active IP Right Cessation
- 2004-07-15 AR ARP040102487A patent/AR045994A1/es unknown
- 2004-08-07 UA UAA200600307A patent/UA81051C2/uk unknown
-
2005
- 2005-11-22 IL IL172101A patent/IL172101A/en not_active IP Right Cessation
-
2006
- 2006-06-28 HK HK06107280A patent/HK1087026A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP1646387B1 (en) | 2006-11-15 |
CA2526052C (en) | 2011-08-30 |
IL172101A0 (en) | 2009-02-11 |
DE602004003251T2 (de) | 2007-05-10 |
ES2275232T3 (es) | 2007-06-01 |
JP2009513544A (ja) | 2009-04-02 |
EP1646387A1 (en) | 2006-04-19 |
PT1646387E (pt) | 2007-01-31 |
AU2004262878A1 (en) | 2005-02-17 |
EA008144B1 (ru) | 2007-04-27 |
KR20060033006A (ko) | 2006-04-18 |
DE602004003251D1 (de) | 2006-12-28 |
GEP20084343B (en) | 2008-03-25 |
HK1087026A1 (en) | 2006-10-06 |
PL1646387T3 (pl) | 2007-03-30 |
WO2005013989A1 (en) | 2005-02-17 |
AR045994A1 (es) | 2005-11-23 |
US7638534B2 (en) | 2009-12-29 |
ATE345134T1 (de) | 2006-12-15 |
US20060183775A1 (en) | 2006-08-17 |
ITMI20031468A1 (it) | 2005-01-19 |
MXPA06000651A (es) | 2006-03-30 |
AU2004262878B2 (en) | 2009-12-17 |
CN100427089C (zh) | 2008-10-22 |
KR101073993B1 (ko) | 2011-10-17 |
CA2526052A1 (en) | 2005-02-17 |
JP4881729B2 (ja) | 2012-02-22 |
IL172101A (en) | 2011-08-31 |
EA200600271A1 (ru) | 2006-06-30 |
CN1809356A (zh) | 2006-07-26 |
DK1646387T3 (da) | 2007-03-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5371790B2 (ja) | 睡眠および認知に関するうつ病における残存症状の治療のための組み合わされたセロトニン再取り込み、5−ht3および5−ht1a活性を有する化合物としての1−[2−(2,4−ジメチルフェニルスルファニル)フェニル]ピペラジン | |
CZ282142B6 (cs) | Cykloalkylsubstituované glutaramidové deriváty, farmaceutický prostředek obsahující tyto sloučeniny a použití | |
US20190322698A1 (en) | Water-soluble allopregnenolone derivative and use thereof | |
TWI441630B (zh) | 曲馬朵(Tramadol)和可舒葆(Coxib)之共結晶物 | |
ES2601250T3 (es) | Fármaco activo contra el dolor neuropático | |
UA81051C2 (en) | Use of indazole derivatives for the treatment of neuropathic pain | |
WO2015101294A1 (zh) | 镇痛活性化合物及其医药用途 | |
EP4294789A1 (en) | Compositions of essentially pure form iv of n-((r)-2,3- dihydroxypropoxy)-3,4-difluoro-2- (2-fluoro-4-iodophenylamino)- benzamide and uses thereof | |
WO1998014430A1 (fr) | Derives de pyrimidine | |
CA3125655A1 (en) | Crystalline forms of (s)-2-(7-cyano-1h-benzimidazol-1 yl)- n-{1-[4-(1-cyano-1-methylethyl)phenyl]ethyl}acetamide | |
JP5060133B2 (ja) | エステル誘導体及びその医薬用途 | |
JPS622583B2 (zh) | ||
WO2019034059A1 (zh) | 新化合物及其在治疗炎症或炎症相关疾病方面的应用 | |
UA81050C2 (en) | Use of 2h[1,3]-oxazino[3, 2-a]indole derivatives for the treatment of neuropathic pain | |
JPS6270384A (ja) | 新規なリン酸エステル化合物 |