HRP20161497T1 - Lijek koji je djelotvoran protiv neuropatskih bolova - Google Patents
Lijek koji je djelotvoran protiv neuropatskih bolova Download PDFInfo
- Publication number
- HRP20161497T1 HRP20161497T1 HRP20161497TT HRP20161497T HRP20161497T1 HR P20161497 T1 HRP20161497 T1 HR P20161497T1 HR P20161497T T HRP20161497T T HR P20161497TT HR P20161497 T HRP20161497 T HR P20161497T HR P20161497 T1 HRP20161497 T1 HR P20161497T1
- Authority
- HR
- Croatia
- Prior art keywords
- acid
- compound
- pharmaceutically acceptable
- group
- pharmaceutical formulation
- Prior art date
Links
- 208000004296 neuralgia Diseases 0.000 title claims 3
- 208000021722 neuropathic pain Diseases 0.000 title claims 3
- 239000003814 drug Substances 0.000 title 1
- 229940079593 drug Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 15
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 12
- 239000011707 mineral Substances 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 239000002253 acid Substances 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 239000003513 alkali Substances 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims 2
- AXWLKJWVMMAXBD-UHFFFAOYSA-N 1-butylpiperidine Chemical compound CCCCN1CCCCC1 AXWLKJWVMMAXBD-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- LDDMACCNBZAMSG-BDVNFPICSA-N (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal Chemical compound CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO LDDMACCNBZAMSG-BDVNFPICSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- LPCWDBCEHWHJGX-UHFFFAOYSA-N 1-ethyl-2-methylpiperidine Chemical compound CCN1CCCCC1C LPCWDBCEHWHJGX-UHFFFAOYSA-N 0.000 claims 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 239000004097 EU approved flavor enhancer Substances 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 239000004909 Moisturizer Substances 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 208000008765 Sciatica Diseases 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 239000002250 absorbent Substances 0.000 claims 1
- 230000002745 absorbent Effects 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 230000002421 anti-septic effect Effects 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims 1
- -1 disintegrators Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 235000019264 food flavour enhancer Nutrition 0.000 claims 1
- 235000003599 food sweetener Nutrition 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 235000011167 hydrochloric acid Nutrition 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 235000014413 iron hydroxide Nutrition 0.000 claims 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 1
- 239000000347 magnesium hydroxide Substances 0.000 claims 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 230000001333 moisturizer Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 239000002674 ointment Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 230000003204 osmotic effect Effects 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000008174 sterile solution Substances 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000003765 sweetening agent Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 1
- KKLAORVGAKUOPZ-UHFFFAOYSA-M trimethyl(phenyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)C1=CC=CC=C1 KKLAORVGAKUOPZ-UHFFFAOYSA-M 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims 1
- 229940007718 zinc hydroxide Drugs 0.000 claims 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Claims (25)
1. Spoj, naznačen time, da ima sljedeću formulu (I):
[image]
u kojoj
R je linearna ili razgranata alkil-skupina koja sadrži od jednog do tri atoma ugljika,
Y je CH ili N, i
p je cijeli broj od 0 do 3,
te njegove soli, bilo kiselinske adicijske soli s farmaceutski prihvatljivom organskom ili mineralnom kiselinom, ili lužnate adicijske soli s farmaceutski prihvatljivom organskom ili mineralnom lužinom.
2. Spoj prema zahtjevu 1, naznačen time, da R je linearna ili razgranata alkil-skupina koja sadrži od dva do tri atoma ugljika.
3. Spoj prema zahtjevu 1, naznačen time, da Y je CH.
4. Spoj prema zahtjevu 1, naznačen time, da p je cijeli broj od 0 do 1.
5. Spoj prema zahtjevu 1, naznačen time, da su R, Y i p te pozicija sljedeće skupine:
[image]
,
predstavljeni u sljedećoj tablici:
[image]
6. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da je navedena farmaceutski prihvatljiva organska ili mineralna kiselina odabrana iz skupine koju čine oksalna kiselina, maleična kiselina, metansulfonska kiselina,
para-toluensulfonska kiselina, sukcinska kiselina, limunska kiselina, vinska kiselina, mliječna kiselina, klorovodična kiselina, fosforna kiselina, sumporna kiselina, aspartna kiselina i glutaminska kiselina.
7. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time, da je navedena farmaceutski prihvatljiva organska ili mineralna lužina odabrana iz skupine koju čine metilamin, dimetilamin, trimetilamin, etilamin, dietilamin, trietilamin, propilamin, dipropilamin, tripropilamin, etilendiamin, monoetanolamin, dietanolamin, trietanolamin, guanidin, morfolin, piperidin, pirolidin, piperazin,
1-butilpiperidin, 1-etil-2-metilpiperidin, N-metil-piperazin, 1,4-dimetilpiperazin,
N-benzilfeniletilamin, N-metilglukozamin, tris(hidroksimetil)aminometan, arginin,
lizin, amonijak, natrijev hidroksid, kalcijev hidroksid, kalijev hidroksid, aluminijev hidroksid, željezni hidroksid, magnezijev hidroksid i cinkov hidroksid.
8. Farmaceutska formulacija, naznačena time, da obuhvaća učinkovitu količinu spoja sljedeće formule (I):
[image]
u kojoj:
R je linearna ili razgranata alkil-skupina koja sadrži od jednog do tri atoma ugljika,
Y je CH ili N, i
p je cijeli broj od 0 do 3,
i njegove soli, bilo kiselinske adicijske soli s farmaceutski prihvatljivom organskom ili mineralnom kiselinom, ili lužnate adicijske soli s farmaceutski prihvatljivom organskom ili mineralnom lužinom, te
najmanje jedno farmaceutski prihvatljivo pomoćno sredstvo.
9. Farmaceutska formulacija prema zahtjevu 8, naznačena time, da je navedeno najmanje jedno farmaceutski prihvatljivo pomoćno sredstvo odabrano iz skupine koju čine sredstva za otpuštanje, veziva, dezintegratori, punila, razrjeđivači, bojila, fluidizatori, klizači, maziva, konzervansi, stabilizatori, ovlaživači, apsorbenti, tenzidi, puferi, soli za regulaciju osmotskog tlaka, emulzifikatori, pojačivači okusa i zaslađivači.
10. Farmaceutska formulacija prema zahtjevu 8, naznačena time, da je spoj formule (I) definiran u skladu s bilo kojim od zahtjeva 1 do 7.
11. Farmaceutska formulacija prema bilo kojem od zahtjeva 8 do 10, naznačena time, da je farmaceutska formulacija odabrana iz skupine koju čine tablete, kapsule, obložene tablete, granule, otopine i sirupi za oralnu primjenu, antiseptički flasteri, otopine, kaše, kreme i masti za transdermalnu primjenu, supozitoriji za rektalnu primjenu, sterilne otopine za injekcijsku ili aerosolnu primjenu, u obliku trenutnog otpuštanja ili u obliku odgođenog otpuštanja.
12. Farmaceutska formulacija prema bilo kojem od zahtjeva 8 do 11, naznačena time, da navedena farmaceutska formulacija obuhvaća takvu količinu spoja formule (I) ili njegove kiselinske adicijske soli ili njegove lužnate adicijske soli, izraženo u slobodnom obliku, koja omogućava razinu primjene spoja formule (I) od 0,001 do 100 mg/kg po danu.
13. Farmaceutska formulacija prema zahtjevu 12, naznačena time, da navedena količina omogućava razinu primjene od 0,05 do 50 mg/kg po danu.
14. Farmaceutska formulacija prema zahtjevu 12, naznačena time, da navedena količina omogućava razinu primjene od 0,1 do 10 mg/kg po danu.
15. Postupak priprave spoja sljedeće formule (I):
[image]
u kojoj
R je linearna ili razgranata alkil-skupina koja sadrži od jednog do tri atoma ugljika,
Y je CH ili N, i
p je cijeli broj od 0 do 3,
te njegove soli, bilo kiselinske adicijske soli s farmaceutski prihvatljivom organskom ili mineralnom kiselinom, ili lužnate adicijske soli s farmaceutski prihvatljivom organskom ili mineralnom lužinom,
naznačen time, da obuhvaća sljedeće korake:
(1) reakcija između spoja sljedeće formule A:
[image]
u kojoj:
R ima značenje koje je gore opisano, dok A predstavlja anionski ostatak mineralne ili organske kiseline,
i spoja sljedeće formule B:
[image]
u kojoj Y i p imaju značenje koje je gore opisano, R1 predstavlja linearnu ili razgranatu alkilnu, arilnu, arilalkilnu ili alkilarilnu skupinu, koja sadrži od jednog do 10 atoma ugljika, dok X predstavlja atom halogena, i
(2) naknadna hidroliza estera koji je dobiven iz reakcije u koraku (1).
16. Proizvodni postupak prema zahtjevu 15, naznačen time, da je navedeni ostatak A odabran iz skupine koju čine halid, fosfat, sulfat, nitrat i organski karboksilat.
17. Proizvodni postupak prema zahtjevu 16, naznačen time, da je navedeni ostatak A odabran iz skupine koju čine klorid, bromid i jodid.
18. Proizvodni postupak prema zahtjevu 15, naznačen time, da je navedeni ostatak X odabran iz skupine koju čine klorid, bromid i jodid.
19. Proizvodni postupak prema zahtjevu 15, naznačen time, da je navedena skupina R1 odabrana iz skupine koju čine linearni ili razgranati alkil koji sadrži od jednog do šest atoma ugljika, te aril, arilalkil i alkilaril koji sadrže od 7 do 8 atoma ugljika.
20. Proizvodni postupak prema bilo kojem od zahtjeva 15 do 19, naznačen time, da se navedena reakcija (1) izvodi u organskom otapalu koje je odabrano iz skupine koju čine polarna aprotska otapala.
21. Proizvodni postupak prema zahtjevu 20, naznačen time, da je navedeno organsko otapalo odabrano iz skupine koju čine aceton, metiletilketon, tetrahidrofuran, dimetilformamid, dimetilsulfoksid, dioksan i acetonitril.
22. Proizvodni postupak prema bilo kojem od zahtjeva 15 do 21, naznačen time, da se navedena reakcija (1) izvodi u prisutnosti organskog ili mineralnog lužnatog spoja.
23. Proizvodni postupak prema bilo kojem od zahtjeva 15 do 22, naznačen time, da se navedena reakcija (1) izvodi u prisutnosti aktivacijskog sredstva odabranog iz skupine koju čine kalijev jodid, cezijev jodid, tetrabutilamonijev jodid i trimetilfenilamonijev jodid.
24. Uporaba spoja sljedeće formule (I):
[image]
u kojoj
R je linearna ili razgranata alkil-skupina koja sadrži od jednog do tri atoma ugljika,
Y je CH ili N, i
p je cijeli broj od 0 do 3,
te njegove soli, bilo kiselinske adicijske soli s farmaceutski prihvatljivom organskom ili mineralnom kiselinom, ili lužnate adicijske soli s farmaceutski prihvatljivom organskom ili mineralnom lužinom,
naznačena time, da je za proizvodnju farmaceutskog sastava za liječenje neuropatskih bolova.
25. Uporaba spoja prema zahtjevu 24, naznačena time, da je za proizvodnju farmaceutskog sastava za liječenje neuropatskih bolova koji su uzrokovani sljedećim stanjima: dijabetes, rak, imunološka deficijencija, ozljeda, ishemija, multipla skleroza, išijas, trigeminalna neuralgija i postherpetični sindrom.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07425709 | 2007-11-12 | ||
| EP08850378.4A EP2207776B9 (en) | 2007-11-12 | 2008-11-06 | Drug active in neuropathic pain |
| PCT/EP2008/065081 WO2009062883A1 (en) | 2007-11-12 | 2008-11-06 | Drug active in neuropathic pain |
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| US (1) | US8455519B2 (hr) |
| EP (1) | EP2207776B9 (hr) |
| JP (1) | JP5443372B2 (hr) |
| KR (1) | KR101555626B1 (hr) |
| CN (1) | CN101855220B (hr) |
| AR (1) | AR069249A1 (hr) |
| AU (1) | AU2008323026B2 (hr) |
| CA (1) | CA2702874C (hr) |
| CY (1) | CY1118131T1 (hr) |
| DK (1) | DK2207776T3 (hr) |
| EA (1) | EA019405B1 (hr) |
| ES (1) | ES2601250T3 (hr) |
| GE (1) | GEP20125526B (hr) |
| HK (1) | HK1142884A1 (hr) |
| HR (1) | HRP20161497T1 (hr) |
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| LT (1) | LT2207776T (hr) |
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| PL (1) | PL2207776T3 (hr) |
| PT (1) | PT2207776T (hr) |
| SG (1) | SG185982A1 (hr) |
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| WO2013124158A1 (en) | 2012-02-21 | 2013-08-29 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | 1h-indazole-3-carboxamide compounds as glycogen synthase kinase 3 beta inhibitors |
| SG10201701171TA (en) | 2012-02-21 | 2017-04-27 | Acraf | Use of 1h-indazole-3-carboxamide compounds as glycogen synthase kinase 3 beta inhibitors |
| WO2020027150A1 (ja) * | 2018-07-31 | 2020-02-06 | 小野薬品工業株式会社 | ベンゼン誘導体 |
| JP7384179B2 (ja) * | 2020-01-29 | 2023-11-21 | 小野薬品工業株式会社 | ベンゼン誘導体を含有する医薬組成物 |
| KR20220132537A (ko) * | 2020-01-29 | 2022-09-30 | 오노 야꾸힝 고교 가부시키가이샤 | 벤젠 유도체의 신규 결정형 |
| KR102374820B1 (ko) | 2020-11-04 | 2022-03-16 | 전남대학교병원 | 프레가발린 및 티아넵틴을 포함하는 신경병성 통증 치료용 약학적 조성물 |
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| DE69627323T2 (de) * | 1995-05-31 | 2004-01-15 | Nisshin Seifun Group Inc | Indazolderivate mit einer cyclischen aminogruppe |
| IT1291569B1 (it) | 1997-04-15 | 1999-01-11 | Angelini Ricerche Spa | Indazolammidi come agenti serotoninergici |
| AU3676100A (en) | 1999-04-09 | 2000-11-14 | Mochida Pharmaceutical Co., Ltd. | Remedies for neuropathic pain |
| ITMI20030972A1 (it) * | 2003-05-15 | 2004-11-16 | Acraf | Indazolo dotato di attivita' analgesica, metodo per prepararlo e composizione farmaceutica che lo comprende. |
| ITMI20031468A1 (it) | 2003-07-18 | 2005-01-19 | Acraf | Farmaco ativo nel dolore neuropatico |
| US7834010B2 (en) * | 2003-12-23 | 2010-11-16 | Serodus As | Modulators of peripheral 5-HT receptors |
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