DE60012508T2 - Aminosäuren mit polycyclischer struktur als pharmaka - Google Patents
Aminosäuren mit polycyclischer struktur als pharmaka Download PDFInfo
- Publication number
- DE60012508T2 DE60012508T2 DE60012508T DE60012508T DE60012508T2 DE 60012508 T2 DE60012508 T2 DE 60012508T2 DE 60012508 T DE60012508 T DE 60012508T DE 60012508 T DE60012508 T DE 60012508T DE 60012508 T2 DE60012508 T2 DE 60012508T2
- Authority
- DE
- Germany
- Prior art keywords
- aminomethyl
- indan
- acetic acid
- compound according
- medicament
- 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.)
- Expired - Fee Related
Links
- 150000001413 amino acids Chemical class 0.000 title abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000003814 drug Substances 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 33
- 208000002193 Pain Diseases 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 21
- 230000036407 pain Effects 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 208000019116 sleep disease Diseases 0.000 claims description 7
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 208000006083 Hypokinesia Diseases 0.000 claims description 4
- 206010033664 Panic attack Diseases 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 230000003483 hypokinetic effect Effects 0.000 claims description 4
- 230000002981 neuropathic effect Effects 0.000 claims description 4
- 208000019906 panic disease Diseases 0.000 claims description 4
- UXCNMSNACVGRFX-UHFFFAOYSA-N 2-[2-(aminomethyl)-1,3-dihydrocyclopenta[a]naphthalen-2-yl]acetic acid Chemical compound C1=CC=CC2=C(CC(CN)(CC(O)=O)C3)C3=CC=C21 UXCNMSNACVGRFX-UHFFFAOYSA-N 0.000 claims description 3
- RSBRZIIGOOVJFX-UHFFFAOYSA-N 2-[2-(aminomethyl)-1,3-dihydrocyclopenta[b]naphthalen-2-yl]acetic acid Chemical compound C1=CC=C2C=C(CC(CN)(CC(O)=O)C3)C3=CC2=C1 RSBRZIIGOOVJFX-UHFFFAOYSA-N 0.000 claims description 3
- XLHRVJITHVCLJF-UHFFFAOYSA-N 2-[2-(aminomethyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC=C2CC(CN)(CC(O)=O)CC2=C1 XLHRVJITHVCLJF-UHFFFAOYSA-N 0.000 claims description 3
- QCXQQQAXRWJAJR-UHFFFAOYSA-N 2-[2-(aminomethyl)-1,7-bis(trifluoromethyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC(C(F)(F)F)=C2C(C(F)(F)F)C(CN)(CC(O)=O)CC2=C1 QCXQQQAXRWJAJR-UHFFFAOYSA-N 0.000 claims description 3
- MIQDZWUURXHFFF-UHFFFAOYSA-N 2-[2-(aminomethyl)-4,5-diphenyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound C=1C=CC=CC=1C1=C2CC(CN)(CC(O)=O)CC2=CC=C1C1=CC=CC=C1 MIQDZWUURXHFFF-UHFFFAOYSA-N 0.000 claims description 3
- VFMHWFDTLWSLQG-UHFFFAOYSA-N 2-[2-(aminomethyl)-4,7-di(propan-2-yl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC(C)C1=CC=C(C(C)C)C2=C1CC(CN)(CC(O)=O)C2 VFMHWFDTLWSLQG-UHFFFAOYSA-N 0.000 claims description 3
- QSEFYODGNGUBHW-UHFFFAOYSA-N 2-[2-(aminomethyl)-4,7-dibromo-1,3-dihydroinden-2-yl]acetic acid Chemical compound BrC1=CC=C(Br)C2=C1CC(CN)(CC(O)=O)C2 QSEFYODGNGUBHW-UHFFFAOYSA-N 0.000 claims description 3
- PSHXYMCXRQKIAB-UHFFFAOYSA-N 2-[2-(aminomethyl)-4,7-dichloro-1,3-dihydroinden-2-yl]acetic acid Chemical compound ClC1=CC=C(Cl)C2=C1CC(CN)(CC(O)=O)C2 PSHXYMCXRQKIAB-UHFFFAOYSA-N 0.000 claims description 3
- UVHHQJTXTRGROQ-UHFFFAOYSA-N 2-[2-(aminomethyl)-4,7-dimethoxy-1,3-dihydroinden-2-yl]acetic acid Chemical compound COC1=CC=C(OC)C2=C1CC(CN)(CC(O)=O)C2 UVHHQJTXTRGROQ-UHFFFAOYSA-N 0.000 claims description 3
- YRTQJSSCCCCWKO-UHFFFAOYSA-N 2-[2-(aminomethyl)-4,7-dimethyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC1=CC=C(C)C2=C1CC(CN)(CC(O)=O)C2 YRTQJSSCCCCWKO-UHFFFAOYSA-N 0.000 claims description 3
- OHXKEDNGJJTYDK-UHFFFAOYSA-N 2-[2-(aminomethyl)-4,7-diphenyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1C(CN)(CC(O)=O)CC2=C1C(C=1C=CC=CC=1)=CC=C2C1=CC=CC=C1 OHXKEDNGJJTYDK-UHFFFAOYSA-N 0.000 claims description 3
- HHHGGJXZGPBCBI-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-(2-methylpropyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC(C)CC1=CC=CC2=C1CC(CN)(CC(O)=O)C2 HHHGGJXZGPBCBI-UHFFFAOYSA-N 0.000 claims description 3
- ZGZXBFQTIXGCCM-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-(dimethylamino)-1,3-dihydroinden-2-yl]acetic acid Chemical compound CN(C)C1=CC=CC2=C1CC(CN)(CC(O)=O)C2 ZGZXBFQTIXGCCM-UHFFFAOYSA-N 0.000 claims description 3
- ALVMUTGCMBSVHL-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-(methylamino)-1,3-dihydroinden-2-yl]acetic acid Chemical compound CNC1=CC=CC2=C1CC(CN)(CC(O)=O)C2 ALVMUTGCMBSVHL-UHFFFAOYSA-N 0.000 claims description 3
- ZWWKDQZNDVWZPE-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-(trifluoromethyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC(C(F)(F)F)=C2CC(CN)(CC(O)=O)CC2=C1 ZWWKDQZNDVWZPE-UHFFFAOYSA-N 0.000 claims description 3
- DXKTVPJGEJGNDZ-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-bromo-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC(Br)=C2CC(CN)(CC(O)=O)CC2=C1 DXKTVPJGEJGNDZ-UHFFFAOYSA-N 0.000 claims description 3
- OJOZXHYPHMBHEE-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-chloro-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC(Cl)=C2CC(CN)(CC(O)=O)CC2=C1 OJOZXHYPHMBHEE-UHFFFAOYSA-N 0.000 claims description 3
- MLSOKLXJRHKHGL-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-cyano-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC(C#N)=C2CC(CN)(CC(O)=O)CC2=C1 MLSOKLXJRHKHGL-UHFFFAOYSA-N 0.000 claims description 3
- GVNXVHZUNBRSSW-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-hydroxy-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC(O)=C2CC(CN)(CC(O)=O)CC2=C1 GVNXVHZUNBRSSW-UHFFFAOYSA-N 0.000 claims description 3
- AESOQYXOAGBNOF-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-iodo-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC(I)=C2CC(CN)(CC(O)=O)CC2=C1 AESOQYXOAGBNOF-UHFFFAOYSA-N 0.000 claims description 3
- KFKKTNSNOHQTQI-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-methoxy-1,3-dihydroinden-2-yl]acetic acid Chemical compound COC1=CC=CC2=C1CC(CN)(CC(O)=O)C2 KFKKTNSNOHQTQI-UHFFFAOYSA-N 0.000 claims description 3
- JKPDBBJXYQIFBR-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-methyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC1=CC=CC2=C1CC(CN)(CC(O)=O)C2 JKPDBBJXYQIFBR-UHFFFAOYSA-N 0.000 claims description 3
- CEIWUGHYGHQCMY-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-nitro-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC([N+]([O-])=O)=C2CC(CN)(CC(O)=O)CC2=C1 CEIWUGHYGHQCMY-UHFFFAOYSA-N 0.000 claims description 3
- LVQOLBGEJGXSMK-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-phenyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound C=12CC(CN)(CC(O)=O)CC2=CC=CC=1C1=CC=CC=C1 LVQOLBGEJGXSMK-UHFFFAOYSA-N 0.000 claims description 3
- OQUGOVRWSBWITN-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-propan-2-yl-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC(C)C1=CC=CC2=C1CC(CN)(CC(O)=O)C2 OQUGOVRWSBWITN-UHFFFAOYSA-N 0.000 claims description 3
- SQMSWUQMENMMNP-UHFFFAOYSA-N 2-[2-(aminomethyl)-5,6-bis(trifluoromethyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound FC(F)(F)C1=C(C(F)(F)F)C=C2CC(CN)(CC(O)=O)CC2=C1 SQMSWUQMENMMNP-UHFFFAOYSA-N 0.000 claims description 3
- ZYPKQKMYWBOENT-UHFFFAOYSA-N 2-[2-(aminomethyl)-5,6-dibromo-1,3-dihydroinden-2-yl]acetic acid Chemical compound BrC1=C(Br)C=C2CC(CN)(CC(O)=O)CC2=C1 ZYPKQKMYWBOENT-UHFFFAOYSA-N 0.000 claims description 3
- GTDPSHREZDIPGW-UHFFFAOYSA-N 2-[2-(aminomethyl)-5,6-dichloro-1,3-dihydroinden-2-yl]acetic acid Chemical compound ClC1=C(Cl)C=C2CC(CN)(CC(O)=O)CC2=C1 GTDPSHREZDIPGW-UHFFFAOYSA-N 0.000 claims description 3
- CJRPZSYBVSXRPM-UHFFFAOYSA-N 2-[2-(aminomethyl)-5,6-dimethoxy-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(OC)C(OC)=CC2=C1CC(CN)(CC(O)=O)C2 CJRPZSYBVSXRPM-UHFFFAOYSA-N 0.000 claims description 3
- UFJVNXKJSFPRSW-UHFFFAOYSA-N 2-[2-(aminomethyl)-5,6-dimethyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(C)C(C)=CC2=C1CC(CN)(CC(O)=O)C2 UFJVNXKJSFPRSW-UHFFFAOYSA-N 0.000 claims description 3
- TZMKPNYEPPXLKG-UHFFFAOYSA-N 2-[2-(aminomethyl)-5,6-diphenyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound C=1C=CC=CC=1C=1C=C2CC(CN)(CC(O)=O)CC2=CC=1C1=CC=CC=C1 TZMKPNYEPPXLKG-UHFFFAOYSA-N 0.000 claims description 3
- OIWMRNPUPDNZCH-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-(2-methylpropyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC(C)CC1=CC=C2CC(CN)(CC(O)=O)CC2=C1 OIWMRNPUPDNZCH-UHFFFAOYSA-N 0.000 claims description 3
- ZSQAMHGUMHHCNT-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-(methylamino)-1,3-dihydroinden-2-yl]acetic acid Chemical compound CNC1=CC=C2CC(CN)(CC(O)=O)CC2=C1 ZSQAMHGUMHHCNT-UHFFFAOYSA-N 0.000 claims description 3
- RPFDJYQZQVIZMW-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-(trifluoromethyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C=C2CC(CN)(CC(O)=O)CC2=C1 RPFDJYQZQVIZMW-UHFFFAOYSA-N 0.000 claims description 3
- SRFJQVXMHDSZNK-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-bromo-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(Br)C=C2CC(CN)(CC(O)=O)CC2=C1 SRFJQVXMHDSZNK-UHFFFAOYSA-N 0.000 claims description 3
- ZHRMXRCZZHMQBS-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-chloro-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(Cl)C=C2CC(CN)(CC(O)=O)CC2=C1 ZHRMXRCZZHMQBS-UHFFFAOYSA-N 0.000 claims description 3
- WWZYNZFKAYHRAR-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-cyano-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(C#N)C=C2CC(CN)(CC(O)=O)CC2=C1 WWZYNZFKAYHRAR-UHFFFAOYSA-N 0.000 claims description 3
- MOWVRSCJVCQMSE-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-hydroxy-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(O)C=C2CC(CN)(CC(O)=O)CC2=C1 MOWVRSCJVCQMSE-UHFFFAOYSA-N 0.000 claims description 3
- LANGCJKTGXHZHH-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-iodo-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(I)C=C2CC(CN)(CC(O)=O)CC2=C1 LANGCJKTGXHZHH-UHFFFAOYSA-N 0.000 claims description 3
- YJLDEDWEXYIOMD-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-methoxy-1,3-dihydroinden-2-yl]acetic acid Chemical compound COC1=CC=C2CC(CN)(CC(O)=O)CC2=C1 YJLDEDWEXYIOMD-UHFFFAOYSA-N 0.000 claims description 3
- SBVLRQZRSHNZRC-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-methyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC1=CC=C2CC(CN)(CC(O)=O)CC2=C1 SBVLRQZRSHNZRC-UHFFFAOYSA-N 0.000 claims description 3
- TVNMFMXAGHQSSI-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-nitro-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C([N+]([O-])=O)C=C2CC(CN)(CC(O)=O)CC2=C1 TVNMFMXAGHQSSI-UHFFFAOYSA-N 0.000 claims description 3
- KAQPTHHXXLYVOD-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-phenyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C2CC(CN)(CC(O)=O)CC2=CC=C1C1=CC=CC=C1 KAQPTHHXXLYVOD-UHFFFAOYSA-N 0.000 claims description 3
- HUPXXTVXEPGYBD-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-propan-2-yl-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC(C)C1=CC=C2CC(CN)(CC(O)=O)CC2=C1 HUPXXTVXEPGYBD-UHFFFAOYSA-N 0.000 claims description 3
- DBRBFIMBDUXPGL-UHFFFAOYSA-N 2-[4-amino-2-(aminomethyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=CC(N)=C2CC(CN)(CC(O)=O)CC2=C1 DBRBFIMBDUXPGL-UHFFFAOYSA-N 0.000 claims description 3
- UNMGIOSWSAOLKX-UHFFFAOYSA-N 2-[5-amino-2-(aminomethyl)-1,3-dihydroinden-2-yl]acetic acid Chemical compound C1=C(N)C=C2CC(CN)(CC(O)=O)CC2=C1 UNMGIOSWSAOLKX-UHFFFAOYSA-N 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 208000022148 skull disease Diseases 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- QCXMLTOWLPGLGT-UHFFFAOYSA-N 2-(aminomethyl)-2-(carboxymethyl)-1,3-dihydroindene-4-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2CC(CN)(CC(O)=O)CC2=C1 QCXMLTOWLPGLGT-UHFFFAOYSA-N 0.000 claims description 2
- BHNNPATUPSXNSA-UHFFFAOYSA-N 2-(aminomethyl)-2-(carboxymethyl)-1,3-dihydroindene-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2CC(CN)(CC(O)=O)CC2=C1 BHNNPATUPSXNSA-UHFFFAOYSA-N 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- PHTBHEKKNNTFCQ-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-methoxycarbonyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound COC(=O)C1=CC=CC2=C1CC(CN)(CC(O)=O)C2 PHTBHEKKNNTFCQ-UHFFFAOYSA-N 0.000 claims 1
- RJBAUYMNKHEERV-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-methoxycarbonyl-1,3-dihydroinden-2-yl]acetic acid Chemical compound COC(=O)C1=CC=C2CC(CN)(CC(O)=O)CC2=C1 RJBAUYMNKHEERV-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 32
- 229940079593 drug Drugs 0.000 description 26
- 150000002431 hydrogen Chemical class 0.000 description 25
- -1 chloro, bromo, hydroxy, hydroxymethyl Chemical group 0.000 description 19
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 17
- 241000699670 Mus sp. Species 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 239000000651 prodrug Substances 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 8
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 229960002870 gabapentin Drugs 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 208000006011 Stroke Diseases 0.000 description 5
- 230000002490 cerebral effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000036651 mood Effects 0.000 description 5
- 230000003040 nociceptive effect Effects 0.000 description 5
- 238000007920 subcutaneous administration Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 4
- 208000004454 Hyperalgesia Diseases 0.000 description 4
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 206010022437 insomnia Diseases 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000001256 tonic effect Effects 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010019196 Head injury Diseases 0.000 description 3
- 208000035154 Hyperesthesia Diseases 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 230000000949 anxiolytic effect Effects 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 125000001786 isothiazolyl group Chemical group 0.000 description 3
- 125000000842 isoxazolyl group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 208000004296 neuralgia Diseases 0.000 description 3
- 229940072228 neurontin Drugs 0.000 description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 230000036544 posture Effects 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003536 tetrazoles Chemical class 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- 125000001984 thiazolidinyl group Chemical group 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- QWCRGCBOYCCWTN-UHFFFAOYSA-N 1,3-diphenyl-1h-indene-2-carboxylic acid Chemical compound OC(=O)C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1C1=CC=CC=C1 QWCRGCBOYCCWTN-UHFFFAOYSA-N 0.000 description 2
- WCFSNTNWKDOFDA-UHFFFAOYSA-N 2-[2-(aminomethyl)-5-(dimethylamino)-1,3-dihydroinden-2-yl]acetic acid Chemical compound CN(C)C1=CC=C2CC(CN)(CC(O)=O)CC2=C1 WCFSNTNWKDOFDA-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000001387 Causalgia Diseases 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- 208000000094 Chronic Pain Diseases 0.000 description 2
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000028389 Nerve injury Diseases 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 206010043994 Tonic convulsion Diseases 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 208000005298 acute pain Diseases 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 208000002173 dizziness Diseases 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 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 2
- 230000008764 nerve damage Effects 0.000 description 2
- 208000021722 neuropathic pain Diseases 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 230000001107 psychogenic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 230000000946 synaptic effect Effects 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- RNFMTDMUQUUXFS-DDWIOCJRSA-N (4r)-2-azaspiro[4.5]decane-4-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)[C@H]1CNCC11CCCCC1 RNFMTDMUQUUXFS-DDWIOCJRSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- JORCRQJTNLBANP-UHFFFAOYSA-N 1,2,3-triphenylindene Chemical compound C1=CC=CC=C1[C]1C2=CC=CC=C2C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JORCRQJTNLBANP-UHFFFAOYSA-N 0.000 description 1
- QVRKSLOJKQRBAU-UHFFFAOYSA-N 1,3,5,6-tetramethoxy-1h-indene Chemical compound COC1=C(OC)C=C2C(OC)C=C(OC)C2=C1 QVRKSLOJKQRBAU-UHFFFAOYSA-N 0.000 description 1
- YNMXNHNIDGDRKX-UHFFFAOYSA-N 1,3-bis(3,4-dimethoxyphenyl)-5,6-dimethoxy-2,3-dihydro-1h-indene Chemical compound C1=C(OC)C(OC)=CC=C1C1C2=CC(OC)=C(OC)C=C2C(C=2C=C(OC)C(OC)=CC=2)C1 YNMXNHNIDGDRKX-UHFFFAOYSA-N 0.000 description 1
- PTZVKDFWFSDSMK-UHFFFAOYSA-N 1,3-diphenyl-1h-indene Chemical compound C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1C1=CC=CC=C1 PTZVKDFWFSDSMK-UHFFFAOYSA-N 0.000 description 1
- SFUVLUPULIDNOI-UHFFFAOYSA-N 1,3-diphenyl-2,3-dihydro-1h-indene Chemical compound C1C(C=2C=CC=CC=2)C2=CC=CC=C2C1C1=CC=CC=C1 SFUVLUPULIDNOI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GIRNEANODVTENH-UHFFFAOYSA-N 1-(2,3-dimethylbut-2-enyl)-1,3-diphenylindene Chemical compound C12=CC=CC=C2C(CC(C)=C(C)C)(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 GIRNEANODVTENH-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- VBONWYVSDKMTNI-UHFFFAOYSA-N 1-ethoxy-1,3-diphenylindene-2-carboxylic acid Chemical compound C12=CC=CC=C2C(OCC)(C=2C=CC=CC=2)C(C(O)=O)=C1C1=CC=CC=C1 VBONWYVSDKMTNI-UHFFFAOYSA-N 0.000 description 1
- QDDPPRDVFIJASZ-UHFFFAOYSA-N 2-(6-fluoro-2-methyl-3h-inden-1-yl)acetic acid Chemical compound FC1=CC=C2CC(C)=C(CC(O)=O)C2=C1 QDDPPRDVFIJASZ-UHFFFAOYSA-N 0.000 description 1
- HTXHSFPVLYTTKQ-UHFFFAOYSA-N 2-[3-(2-hydroxy-4,5-dimethoxyphenyl)-5,6-dimethoxy-2,3-dihydro-1h-inden-1-yl]-4,5-dimethoxyphenol Chemical compound C1=2C=C(OC)C(OC)=CC=2C(C=2C(=CC(OC)=C(OC)C=2)O)CC1C1=CC(OC)=C(OC)C=C1O HTXHSFPVLYTTKQ-UHFFFAOYSA-N 0.000 description 1
- CJRCEWNGLGYFBY-UHFFFAOYSA-N 2-ethoxy-1,3-diphenyl-1h-indene Chemical compound CCOC1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1C1=CC=CC=C1 CJRCEWNGLGYFBY-UHFFFAOYSA-N 0.000 description 1
- YLFDGLUBFPPLMG-UHFFFAOYSA-N 2-methoxy-1,3-diphenyl-1h-indene Chemical compound COC1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1C1=CC=CC=C1 YLFDGLUBFPPLMG-UHFFFAOYSA-N 0.000 description 1
- RESMERCDIMIFOX-UHFFFAOYSA-N 2-methyl-1,3-diphenyl-1h-indene Chemical compound CC1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1C1=CC=CC=C1 RESMERCDIMIFOX-UHFFFAOYSA-N 0.000 description 1
- WQSFBOJKZRPNPL-UHFFFAOYSA-N 2-methyl-1,3-diphenyl-2,3-dihydro-1h-indene Chemical compound CC1C(C=2C=CC=CC=2)C2=CC=CC=C2C1C1=CC=CC=C1 WQSFBOJKZRPNPL-UHFFFAOYSA-N 0.000 description 1
- 239000003477 4 aminobutyric acid receptor stimulating agent Substances 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000000412 Avitaminosis Diseases 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 0 CC1(*)C(*)(*)*(BC*(C)=*)(CC(O*)=O)C(*)(*)C1(*)* Chemical compound CC1(*)C(*)(*)*(BC*(C)=*)(CC(O*)=O)C(*)(*)C1(*)* 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 108090000312 Calcium Channels Proteins 0.000 description 1
- 102000003922 Calcium Channels Human genes 0.000 description 1
- 241000288950 Callithrix jacchus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000018152 Cerebral disease Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 1
- 206010014498 Embolic stroke Diseases 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010018985 Haemorrhage intracranial Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 208000029433 Herpesviridae infectious disease Diseases 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- 208000008574 Intracranial Hemorrhages Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 206010027951 Mood swings Diseases 0.000 description 1
- 101100460719 Mus musculus Noto gene Proteins 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010028923 Neonatal asphyxia Diseases 0.000 description 1
- 208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000005890 Neuroma Diseases 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 206010068106 Occipital neuralgia Diseases 0.000 description 1
- 208000006199 Parasomnias Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 208000004983 Phantom Limb Diseases 0.000 description 1
- 206010056238 Phantom pain Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 1
- 208000004550 Postoperative Pain Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 206010038669 Respiratory arrest Diseases 0.000 description 1
- 208000005793 Restless legs syndrome Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 206010047627 Vitamin deficiencies Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 206010053552 allodynia Diseases 0.000 description 1
- 102000015007 alpha-adrenergic receptor activity proteins Human genes 0.000 description 1
- 108040006816 alpha-adrenergic receptor activity proteins Proteins 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 230000000338 anxiogenic effect Effects 0.000 description 1
- 208000008784 apnea Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000003461 brachial plexus Anatomy 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000013172 carotid endarterectomy Methods 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 230000003970 cerebral vascular damage Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000010235 enterohepatic circulation Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 206010020765 hypersomnia Diseases 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 208000003532 hypothyroidism Diseases 0.000 description 1
- 230000002989 hypothyroidism Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 241001515942 marmosets Species 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003349 osteoarthritic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 208000033300 perinatal asphyxia Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 208000030062 persistent idiopathic facial pain Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 208000019899 phobic disease Diseases 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000003653 radioligand binding assay Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 230000003093 somatogenic effect Effects 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000005236 sound signal Effects 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000005809 status epilepticus Diseases 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13610099P | 1999-05-26 | 1999-05-26 | |
| US136100P | 1999-05-26 | ||
| PCT/GB2000/001819 WO2000073259A1 (en) | 1999-05-26 | 2000-05-12 | Fused polycyclic amino acids as pharmaceutical agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60012508D1 DE60012508D1 (de) | 2004-09-02 |
| DE60012508T2 true DE60012508T2 (de) | 2005-06-23 |
Family
ID=22471297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60012508T Expired - Fee Related DE60012508T2 (de) | 1999-05-26 | 2000-05-12 | Aminosäuren mit polycyclischer struktur als pharmaka |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1180094B1 (enExample) |
| JP (1) | JP2003500466A (enExample) |
| AT (1) | ATE272048T1 (enExample) |
| AU (1) | AU4770400A (enExample) |
| BR (1) | BR0010961A (enExample) |
| CA (1) | CA2373210A1 (enExample) |
| DE (1) | DE60012508T2 (enExample) |
| DK (1) | DK1180094T3 (enExample) |
| ES (1) | ES2228524T3 (enExample) |
| HK (1) | HK1040237B (enExample) |
| MX (1) | MXPA01011955A (enExample) |
| PT (1) | PT1180094E (enExample) |
| WO (1) | WO2000073259A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005539092A (ja) * | 2002-08-15 | 2005-12-22 | ファイザー・インク | 縮合二環式または三環式アミノ酸の治療における使用 |
| EP1820502A1 (en) | 2006-02-10 | 2007-08-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising azolylcarbinol compounds |
| EP2116539A1 (en) | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| EP2353591A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| EP2353598A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for use in the prevention and/or treatment of postoperative pain |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| EP2415471A1 (en) | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| AU2014364647A1 (en) | 2013-12-17 | 2016-06-23 | Laboratorios Del Dr. Esteve, S.A. | Serotonin-Norepinephrine Reuptake Inhibitors (SNRIs) and Sigma receptor ligands combinations |
| AU2014364644A1 (en) | 2013-12-17 | 2016-06-23 | Laboratorios Del Dr. Esteve, S.A. | Gabapentinoids and Sigma receptor ligands combinations |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI942059A7 (fi) * | 1991-11-05 | 1994-07-04 | Smithkline Beecham Corp | Endoteliinireseptoreiden antagonisteja |
| AU733896B2 (en) * | 1996-10-23 | 2001-05-31 | Warner-Lambert Company | Substituted gamma aminobutyric acids as pharmaceutical agents |
| CU23048A3 (es) * | 1997-10-27 | 2005-06-24 | Warner Lambert Co | Aminoacidos ciclicos y derivados de los mismos, utiles como agentes farmaceuticos |
-
2000
- 2000-05-12 BR BR0010961-4A patent/BR0010961A/pt not_active Application Discontinuation
- 2000-05-12 WO PCT/GB2000/001819 patent/WO2000073259A1/en not_active Ceased
- 2000-05-12 HK HK02101978.2A patent/HK1040237B/en not_active IP Right Cessation
- 2000-05-12 PT PT00929701T patent/PT1180094E/pt unknown
- 2000-05-12 ES ES00929701T patent/ES2228524T3/es not_active Expired - Lifetime
- 2000-05-12 AU AU47704/00A patent/AU4770400A/en not_active Abandoned
- 2000-05-12 CA CA002373210A patent/CA2373210A1/en not_active Abandoned
- 2000-05-12 DE DE60012508T patent/DE60012508T2/de not_active Expired - Fee Related
- 2000-05-12 AT AT00929701T patent/ATE272048T1/de not_active IP Right Cessation
- 2000-05-12 DK DK00929701T patent/DK1180094T3/da active
- 2000-05-12 EP EP00929701A patent/EP1180094B1/en not_active Expired - Lifetime
- 2000-05-12 JP JP2000621326A patent/JP2003500466A/ja active Pending
- 2000-05-12 MX MXPA01011955A patent/MXPA01011955A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| HK1040237B (en) | 2004-12-31 |
| HK1040237A1 (en) | 2002-05-31 |
| BR0010961A (pt) | 2002-03-26 |
| EP1180094A1 (en) | 2002-02-20 |
| JP2003500466A (ja) | 2003-01-07 |
| PT1180094E (pt) | 2004-10-29 |
| DE60012508D1 (de) | 2004-09-02 |
| ATE272048T1 (de) | 2004-08-15 |
| EP1180094B1 (en) | 2004-07-28 |
| CA2373210A1 (en) | 2000-12-07 |
| AU4770400A (en) | 2000-12-18 |
| MXPA01011955A (es) | 2003-09-04 |
| ES2228524T3 (es) | 2005-04-16 |
| WO2000073259A1 (en) | 2000-12-07 |
| DK1180094T3 (da) | 2004-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60019628T2 (de) | Bicyclische aminosäuren als pharmazeutische mittel | |
| DE69822214T2 (de) | ((cyclo)alkyl substituierte)-.gamma.-aminobuttersäure derivate (=gaba analoga), deren herstellung und deren verwendung bei der behandlung von neurologischen erkrankungen | |
| DE69921340T2 (de) | Verzweigte alkylpyrrolidin-3-carbonsäuren | |
| DE69834204T2 (de) | Zyklische aminosäuren und deren derivate als arzneimittel | |
| DE69709070T2 (de) | Verbrückte zyklische aminosäuren als pharmazeutische mittel | |
| DE69826151T2 (de) | 1-substituierte-1-aminomethyl-cycloalkan derivate (= gabapentin analoga), deren herstellung und deren verwendung bei der behandlung von neurologischen erkrankungen | |
| DE69712877T2 (de) | Zyklischaminosäure als pharmazeutische mittel | |
| DE69707842T2 (de) | Zyklische aminosäure als pharmazeutische wirkstoffe | |
| US6489352B2 (en) | Conformationally constrained compounds as pharmaceutical agents | |
| DE60112079T2 (de) | Vebindungen zur modulation des rage-rezeptors | |
| DE60012508T2 (de) | Aminosäuren mit polycyclischer struktur als pharmaka | |
| DE69635886T2 (de) | Exzitatorisch wirkende Aminosäurederivate | |
| DE60017730T2 (de) | 3-heteroarylalkyl-substituierte gaba-analoga | |
| US20050250800A1 (en) | Conformationally constrained compounds as pharmaceutical agents | |
| PT888285E (pt) | Novos amino acidos ciclicos em ponte como agentes farmaceuticos |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: WARNER-LAMBERT COMPANY LLC, MORRIS PLAINS, N.J., U |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |