HRP20180324T1 - Supstituirani derivati 2-[2-(fenil)etilamino]alkanamida i njihova upotreba kao modulatora natrijevih i/ili kalcijevih kanala - Google Patents
Supstituirani derivati 2-[2-(fenil)etilamino]alkanamida i njihova upotreba kao modulatora natrijevih i/ili kalcijevih kanala Download PDFInfo
- Publication number
- HRP20180324T1 HRP20180324T1 HRP20180324TT HRP20180324T HRP20180324T1 HR P20180324 T1 HRP20180324 T1 HR P20180324T1 HR P20180324T T HRP20180324T T HR P20180324TT HR P20180324 T HRP20180324 T HR P20180324T HR P20180324 T1 HRP20180324 T1 HR P20180324T1
- Authority
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- Croatia
- Prior art keywords
- ethylamino
- alkyl
- compound
- hydrogen
- butoxyphenyl
- Prior art date
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- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 title claims 4
- 108090000312 Calcium Channels Proteins 0.000 title claims 3
- 102000003922 Calcium Channels Human genes 0.000 title claims 3
- 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 title claims 3
- 108010052164 Sodium Channels Proteins 0.000 title claims 3
- 102000018674 Sodium Channels Human genes 0.000 title claims 3
- 239000011734 sodium Substances 0.000 title claims 3
- 229910052708 sodium Inorganic materials 0.000 title claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 37
- 229910052739 hydrogen Inorganic materials 0.000 claims 29
- 239000001257 hydrogen Substances 0.000 claims 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- 208000035475 disorder Diseases 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical group C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 230000003287 optical effect Effects 0.000 claims 6
- 208000002193 Pain Diseases 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- GRHBODILPPXVKN-UHFFFAOYSA-N 2-[2-(3-butoxyphenyl)ethylamino]-n,n-dimethylacetamide Chemical compound CCCCOC1=CC=CC(CCNCC(=O)N(C)C)=C1 GRHBODILPPXVKN-UHFFFAOYSA-N 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- 239000003693 atypical antipsychotic agent Substances 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000006530 (C4-C6) alkyl group Chemical group 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 208000025609 Urogenital disease Diseases 0.000 claims 3
- 239000000164 antipsychotic agent Substances 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 229960004170 clozapine Drugs 0.000 claims 3
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims 3
- 230000001149 cognitive effect Effects 0.000 claims 3
- 208000010643 digestive system disease Diseases 0.000 claims 3
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229960003878 haloperidol Drugs 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 208000020016 psychiatric disease Diseases 0.000 claims 3
- 229960001534 risperidone Drugs 0.000 claims 3
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 210000000987 immune system Anatomy 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 230000007170 pathology Effects 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- VVVBEZQPVJOPON-KSLSDJDQSA-N (2R)-2-[2-(3-butoxyphenyl)ethylamino]-N,N-dimethylpropanamide 2-[2-[3-butoxy-2-(trifluoromethyl)phenyl]ethylamino]-N,N-dimethylacetamide Chemical compound C(CCC)OC=1C(=C(C=CC1)CCNCC(=O)N(C)C)C(F)(F)F.C(CCC)OC=1C=C(C=CC1)CCN[C@@H](C(=O)N(C)C)C VVVBEZQPVJOPON-KSLSDJDQSA-N 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006531 (C2-C5) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- NUAHCZNEPOUXAO-UHFFFAOYSA-N 2-[2-(3-butoxy-2,6-difluorophenyl)ethylamino]-n,n-dimethylacetamide Chemical compound CCCCOC1=CC=C(F)C(CCNCC(=O)N(C)C)=C1F NUAHCZNEPOUXAO-UHFFFAOYSA-N 0.000 claims 1
- HEBZOZGBZXKENA-UHFFFAOYSA-N 2-[2-(3-butylsulfonylphenyl)ethylamino]-n,n-dimethylacetamide Chemical compound CCCCS(=O)(=O)C1=CC=CC(CCNCC(=O)N(C)C)=C1 HEBZOZGBZXKENA-UHFFFAOYSA-N 0.000 claims 1
- IMFFKOWDBWQFOM-UHFFFAOYSA-N 2-[2-(3-hexoxyphenyl)ethylamino]-n,n-dimethylacetamide Chemical compound CCCCCCOC1=CC=CC(CCNCC(=O)N(C)C)=C1 IMFFKOWDBWQFOM-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- JTTWLNNOMMGAGB-UHFFFAOYSA-N C(CCC)OC=1C(=C(C=CC1)CCNCC(=O)N(C)C)F.C(CCC)OC=1C(=C(C=CC1)CCNCC(=O)N(C)C)Cl.C(CCC)SC=1C=C(C=CC1)CCNCC(=O)N(C)C Chemical compound C(CCC)OC=1C(=C(C=CC1)CCNCC(=O)N(C)C)F.C(CCC)OC=1C(=C(C=CC1)CCNCC(=O)N(C)C)Cl.C(CCC)SC=1C=C(C=CC1)CCNCC(=O)N(C)C JTTWLNNOMMGAGB-UHFFFAOYSA-N 0.000 claims 1
- DALQTPVCQMVNNL-UHFFFAOYSA-N C(CCC)OC=1C=C(C=C(C1)C(F)(F)F)CCNCC(=O)N(C)C.C(CCC)OC=1C=C(C=CC1C(F)(F)F)CCNCC(=O)N(C)C Chemical compound C(CCC)OC=1C=C(C=C(C1)C(F)(F)F)CCNCC(=O)N(C)C.C(CCC)OC=1C=C(C=CC1C(F)(F)F)CCNCC(=O)N(C)C DALQTPVCQMVNNL-UHFFFAOYSA-N 0.000 claims 1
- ROMBYXLKDVMYTB-UHFFFAOYSA-N C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)COC.C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)CO.C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)C Chemical compound C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)COC.C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)CO.C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)C ROMBYXLKDVMYTB-UHFFFAOYSA-N 0.000 claims 1
- GOCYRFPYTLYFBS-UHFFFAOYSA-N C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N(C)C.C(CCCCC)OC=1C=C(C=CC1)CCNCC(=O)NC.C(CCCC)OC=1C=C(C=CC1)CCNCC(=O)NC Chemical compound C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N(C)C.C(CCCCC)OC=1C=C(C=CC1)CCNCC(=O)NC.C(CCCC)OC=1C=C(C=CC1)CCNCC(=O)NC GOCYRFPYTLYFBS-UHFFFAOYSA-N 0.000 claims 1
- UOUSPOHEYLJZJG-UHFFFAOYSA-N C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N(CCC)CCC.C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N(CC)CC.C(CCC)OC=1C=C(C=CC1OC)CCNCC(=O)N(C)C Chemical compound C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N(CCC)CCC.C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N(CC)CC.C(CCC)OC=1C=C(C=CC1OC)CCNCC(=O)N(C)C UOUSPOHEYLJZJG-UHFFFAOYSA-N 0.000 claims 1
- OHPMYRGVAKIWAS-UHFFFAOYSA-N C(CCC)OC=1C=C(C=CC1)CCNCC(=O)NC.C(CCCCC)OC=1C=C(C=CC1)CCNCC(=O)N.C(CCCC)OC=1C=C(C=CC1)CCNCC(=O)N.C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N Chemical compound C(CCC)OC=1C=C(C=CC1)CCNCC(=O)NC.C(CCCCC)OC=1C=C(C=CC1)CCNCC(=O)N.C(CCCC)OC=1C=C(C=CC1)CCNCC(=O)N.C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N OHPMYRGVAKIWAS-UHFFFAOYSA-N 0.000 claims 1
- WVUUVEHFPDUDFH-JAVZBQFESA-N C(CCC)OC=1C=C(C=CC1)CCN[C@@H](C(=O)NC)C.C(CCC)OC=1C=C(C=CC1)CCN[C@@H](C(=O)N)C.C(CCC)OC=1C=C(C=CC1)CCN[C@H](C(=O)N(C)C)C Chemical compound C(CCC)OC=1C=C(C=CC1)CCN[C@@H](C(=O)NC)C.C(CCC)OC=1C=C(C=CC1)CCN[C@@H](C(=O)N)C.C(CCC)OC=1C=C(C=CC1)CCN[C@H](C(=O)N(C)C)C WVUUVEHFPDUDFH-JAVZBQFESA-N 0.000 claims 1
- MBQVGFDQYDCDLJ-QZCDQQELSA-N C(CCC)OC=1C=C(C=CC1)CCN[C@H](C(=O)NC)C.C(CCC)OC=1C=C(C=CC1)CCN[C@H](C(=O)N)C.C(CCCCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)(C)C Chemical compound C(CCC)OC=1C=C(C=CC1)CCN[C@H](C(=O)NC)C.C(CCC)OC=1C=C(C=CC1)CCN[C@H](C(=O)N)C.C(CCCCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)(C)C MBQVGFDQYDCDLJ-QZCDQQELSA-N 0.000 claims 1
- WZOFNFHSLGILIU-UHFFFAOYSA-N C(CCCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)(C)C.C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)(C)C.C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)COCCC Chemical compound C(CCCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)(C)C.C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)(C)C.C(CCC)OC=1C=C(C=CC1)CCNC(C(=O)N(C)C)COCCC WZOFNFHSLGILIU-UHFFFAOYSA-N 0.000 claims 1
- DINVUBGYMBZYFB-UHFFFAOYSA-N C(CCCCC)OC=1C=C(C=CC1)CCNCC(=O)N(C)C.C(CCCC)OC=1C=C(C=CC1)CCNCC(=O)N(C)C.C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N(CCCC)CCCC Chemical compound C(CCCCC)OC=1C=C(C=CC1)CCNCC(=O)N(C)C.C(CCCC)OC=1C=C(C=CC1)CCNCC(=O)N(C)C.C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N(CCCC)CCCC DINVUBGYMBZYFB-UHFFFAOYSA-N 0.000 claims 1
- ZFMQDQVUZUYOGT-UHFFFAOYSA-N C(CCCCC)OC=1C=C(C=CC1)CCNCC(=O)N1CCCC1.C(CCCC)OC=1C=C(C=CC1)CCNCC(=O)N1CCCC1.C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N1CCCC1 Chemical compound C(CCCCC)OC=1C=C(C=CC1)CCNCC(=O)N1CCCC1.C(CCCC)OC=1C=C(C=CC1)CCNCC(=O)N1CCCC1.C(CCC)OC=1C=C(C=CC1)CCNCC(=O)N1CCCC1 ZFMQDQVUZUYOGT-UHFFFAOYSA-N 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- BKISUIVCTANPFV-UHFFFAOYSA-N FC(CCCOC=1C=C(C=CC1)CCNCC(=O)N(C)C)(F)F.C(CCC)OC=1C=C(C=CC1)C(CNCC(=O)N(C)C)(C)C.C(CCC)OC=1C=C(C=CC1)CCNCC(=S)N(C)C Chemical compound FC(CCCOC=1C=C(C=CC1)CCNCC(=O)N(C)C)(F)F.C(CCC)OC=1C=C(C=CC1)C(CNCC(=O)N(C)C)(C)C.C(CCC)OC=1C=C(C=CC1)CCNCC(=S)N(C)C BKISUIVCTANPFV-UHFFFAOYSA-N 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000002917 arthritic effect Effects 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002124 endocrine Effects 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- VRLSELRYHHSXAL-UHFFFAOYSA-N n,n-dimethyl-2-[2-(3-pentoxyphenyl)ethylamino]acetamide Chemical compound CCCCCOC1=CC=CC(CCNCC(=O)N(C)C)=C1 VRLSELRYHHSXAL-UHFFFAOYSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A—HUMAN NECESSITIES
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4515—Non condensed piperidines, e.g. piperocaine having a butyrophenone group in position 1, e.g. haloperidol
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/00—Drugs for disorders of the urinary system
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- A—HUMAN NECESSITIES
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
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Claims (34)
1. Spoj opće formule (I):
[image]
(I)
u kojoj:
X je -O-, -S- ili -SO2-;
Y je vodik, OH ili O(C1-C4)alkil;
Z je =O ili =S;
R je (C3-C10)alkil; ω-trifluor(C3-C10)alkil;
R1 i R2 jesu, neovisno, vodik, hidroksi, (C1-C8)alkoksi, (C1-C8)alkiltio, halogen, trifluormetil ili 2,2,2-trifluoretil; ili jedan od R1 i R2 je u ortho-položaju prema R-X- i, uzet zajedno s istim R-X-, predstavlja skupinu
[image]
u kojoj R0 jest (C2-C9)alkil;
R3 i R’3 jesu, neovisno, vodik ili (C1-C4)alkil;
R4 i R5 jesu, neovisno, vodik, (C1-C4)alkil; ili R4 je vodik te R5 je skupina odabrana od -CH2-OH, -CH2-O-(C1-C6)alkil, -CH(CH3)-OH,
-(CH2)2-S-CH3, benzil i 4-hidroksibenzil; ili R4 i R5, uzeti zajedno sa susjednim ugljikovim atomom, tvore (C3-C6)cikloalkilni ostatak;
R6 i R7 jesu neovisno vodik ili (C1-C6)alkil; ili uzeti zajedno sa susjednim dušikovim atomom tvore peteročlani ili šesteročlani monociklički zasićeni heterociklički prsten, koji može sadržavati jedan dodatni heteroatom odabran od -O-, -S- i -NR8- gdje R8 je vodik ili (C1-C6)alkil;
pod uvjetom da kada X jest -S- ili -SO2-, tada Y nije OH ili O(C1-C4)alkil; u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
2. Spoj iz patentnog zahtjeva 1 naznačeno time da:
X je -O-, -S-;
Y je vodik, OH ili O(C1-C3)alkil;
Z je =O ili =S;
R je (C4-C7)alkil ili ω-trifluor(C4-C6)alkil;
R1 i R2 jesu, neovisno, vodik, (C1-C4)alkoksi, halogen, trifluormetil ili 2,2,2-trifluoretil; ili jedan od R1 i R2 je u ortho-položaju prema R-X- i, uzet zajedno s istim R-X-, predstavlja skupinu
[image]
u kojoj R0 jest (C2-C5)alkil;
R3 i R’3 jesu, neovisno, vodik ili (C1-C3)alkil;
R4 i R5 jesu, neovisno, vodik ili (C1-C4)alkil; ili R4 je vodik te R5 je skupina odabrana od -CH2-OH, -CH2-O-(C1-C3)alkil, -(CH2)2-S-CH3, benzil i 4-hidroksibenzil;
R6 i R7 jesu, neovisno, vodik ili (C1-C4)alkil; ili uzeti zajedno sa susjednim dušikovim atomom tvore peteročlani ili šesteročlani monociklički zasićeni heterociklički prsten, koji može sadržavati jedan dodatni heteroatom odabran od -O- i -NR8- gdje R8 je vodik ili (C1-C3)alkil;
pod uvjetom da kada X jest -S-, tada Y nije OH ili O(C1-C3)alkil;
u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
3. Spoj iz patentnog zahtjeva 1 naznačeno time da:
X je -O-, -S-;
Y je vodik ili O(C1-C3)alkil;
Z je =O ili =S;
R je (C4-C7)alkil ili ω-trifluor(C4-C6)alkil;
R1 i R2 jesu, neovisno, vodik, (C1-C3)alkoksi, fluor, klor, trifluormetil ili 2,2,2-trifluoretil; ili jedan od R1 i R2 je u ortho-položaju prema R-X- i uzet zajedno s istim R-X-, predstavlja skupinu
[image]
u kojoj R0 jest (C3-C4)alkil;
R3 i R’3 jesu, neovisno, vodik ili (C1-C3)alkil;
R4 i R5 jesu, neovisno, vodik ili (C1-C4)alkil; ili R4 je vodik te R5 je skupina odabrana od
-CH2-OH, -CH2-O-(C1-C3)alkil, benzil i 4-hidroksibenzil;
R6 i R7 jesu, neovisno, vodik ili (C1-C3)alkil; ili uzeti zajedno sa susjednim dušikovim atomom tvore peteročlani ili šesteročlani monociklički zasićeni heterociklički prsten, koji može sadržavati jedan dodatni heteroatom odabran od -O- i -NR8-, gdje R8 je vodik ili (C1-C3)alkil;
pod uvjetom da kada X jest -S-, tada Y nije O(C1-C3)alkil;
u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
4. Spoj iz patentnog zahtjeva 1 naznačeno time da:
X je -O-;
Y je vodik;
Z je =O;
R je (C4-C6)alkil;
R1 i R2 jesu, neovisno, vodik ili halogen, preferirano fluor;
R3, R’3, R4 i R5 su vodik;
R6 i R7 jesu, neovisno, vodik ili (C1-C3)alkil;
u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
5. Spoj iz patentnog zahtjeva 1 naznačeno time da je odabran od:
2-[2-(3-butoksifenil)-etilamino]-acetamid
2-[2-(3-pentiloksifenil)-etilamino]-acetamid
2-[2-(3-heksiloksifenil)-etilamino]-acetamid
2-[2-(3-butoksifenil)-etilamino]-N-metilacetamid
2-[2-(3-pentiloksifenil)-etilamino]-N-metilacetamid
2-[2-(3-heksiloksifenil)-etilamino]-N-metilacetamid
2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butilsulfonilfenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksifenil)-(N’-hidroksi)etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksifenil)-(N’-metoksi)etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksifenil)-(N’-propoksi)etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksifenil)-etilamino]-N,N-dimetil-tioacetamid
2-[2-(3-butoksifenil)-2-metilpropilamino]-N,N-dimetilacetamid
2-{2-[3-(4,4,4-trifluorbutoksi)fenil]-etilamino}-N,N-dimetilacetamid
2-[2-(3-butiltiofenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksi-2-klorfenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksi-2-fluorfenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksi-4-metoksifenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksifenil)-etilamino]-N,N-dietilacetamid
2-[2-(3-butoksifenil)-etilamino]-N,N-dipropilacetamid
2-[2-(3-butoksifenil)-etilamino]-N,N-dibutilacetamid
2-[2-(3-pentiloksifenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-heksiloksifenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksifenil)-etilamino]-1-pirolidin-1-il-etan-1-on
2-[2-(3-pentiloksifenil)-etilamino]-1-pirolidin-1-il-etan-1-on
2-[2-(3-heksiloksifenil)-etilamino]-1-pirolidin-1-il-etan-1-on
2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilpropanamid
2-[2-(3-butoksifenil)-etilamino]-3-hidroksi-N,N-dimetilpropanamid
2-[2-(3-butoksifenil)-etilamino]-3-metoksi-N,N-dimetilpropanamid
2-[2-(3-butoksifenil)-etilamino]-3-propoksi-N,N-dimetilpropanamid
2-[2-(3-butoksifenil)-etilamino]-2,N,N-trimetilpropanamid
2-[2-(3-pentiloksifenil)-etilamino]-2,N,N-trimetilpropanamid
2-[2-(3-heksiloksifenil)-etilamino]-2,N,N-trimetilpropanamid
(S)-2-[2-(3-butoksifenil)-etilamino]-propanamid
(S)-2-[2-(3-butoksifenil)-etilamino]-N-metilpropanamid
(S)-2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilpropanamid
(R)-2-[2-(3-butoksifenil)-etilamino]-propanamid
(R)-2-[2-(3-butoksifenil)-etilamino]-N-metilpropanamid
(R)-2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilpropanamid
2-[2-(3-butoksi-2-trifluormetilfenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksi-4-trifluormetilfenil)-etilamino]-N,N-dimetilacetamid
2-[2-(3-butoksi-5-trifluormetilfenil)-etilamino]-N,N-dimetilacetamid
u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli, preferirano njegova sol s klorovodičnom ili metansulfonskom kiselinom.
6. Spoj iz patentnog zahtjeva 1 naznačeno time da je 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid, 2-[2-(3-butoksi-2,6-difluorfenil)-etilamino]-N,N-dimetilacetamid, 2-[2-(3-pentiloksifenil)-etilamino]-N,N-dimetilacetamid, ili 2-[2-(3-heksiloksifenil)-etilamino]-N,N-dimetilacetamid, i njihove farmaceutski prihvatljive soli.
7. Spoj iz patentnog zahtjeva 6 naznačeno time da je 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid ili njegova farmaceutski prihvatljiva sol.
8. Spoj iz bilo kojeg od patentnih zahtjeva 6 i 7 naznačeno time da farmaceutski prihvatljiva sol jest hidroklorid ili metansulfonat.
9. Spoj iz patentnog zahtjeva 1 naznačeno time da:
X je -SO2-; ili
Y je OH ili O(C1-C4)alkil; ili
Z je =S; ili
R je (C9-C10)alkil ili ω-trifluor(C3-C10)alkil; ili
R1 i/ili R2 su različiti od vodika; ili
oba R3 i R'3 su različiti od vodika; ili
oba R4 i R5 su različiti od vodika, ali kad su uzeti zajedno sa susjednim ugljikovim atomom ne tvore (C3-C6)cikloalkilni ostatak; ili
R6 i R7, uzeti zajedno sa susjednim dušikovim atomom tvore monociklički peteročlani ili šesteročlani zasićeni heterociklički prsten, koji može sadržavati jedan dodatni heteroatom odabran od -O-, -S- i -NR8-, gdje R8 je vodik ili (C1-C6)alkil;
pod uvjetom da kada X jest -S- ili -SO2-, tada Y nije OH ili O(C1-C4)alkil;
u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
10. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu kao lijek.
11. Spoj iz patentnog zahtjeva 1 za upotrebu kao lijek aktivan kao modulator natrijevih i/ili kalcijevih kanala za liječenje patologija u kojima gore rečeni mehanizam (mehanzimi) igra (igraju) patološku ulogu, koja je neurološki, kognitivni, psihijatrijski, upalni, urogenitalni ili gastrointestinalni poremećaj, a rečeni lijek uopće nema MAO inhibitorsku aktivnost ili ima znatno smanjenu MAO inhibitorsku aktivnost.
12. Spoj iz bilo kojeg od patentnih zahtjeva 2, 3 i 4 za upotrebu prema patentnom zahtjevu 11.
13. Spoj iz patentnog zahtjeva 5 za upotrebu prema patentnom zahtjevu 11.
14. Spoj iz patetnog zahtjeva 6 za upotrebu prema patentnom zahtjevu 11.
15. Spoj iz patentnog zahtjeva 7 za upotrebu prema patentnom zahtjevu 11.
16. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest neurološki poremećaj odabran od boli i migrene.
17. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 16 pri čemu bol jest sindrom neuropatske boli ili sindrom upalne boli.
18. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 16 pri čemu bol jest akutna ili kronična bol.
19. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest neurološki poremećaj odabran od Alzheimerove bolesti, Parkinsonove bolesti, epilepsije, sindroma nemirnih nogu, moždanog udara ili cerebralne ishemije.
20. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest upalni proces koji djeluje na sve sustave tijela odabran od artritičnog stanja, poremećaja koji djeluje na kožu i pripadajuća tkiva, poremećaja respiratornog sustava ili poremećaja imunološkog i endokrinološkog sustava.
21. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest kognitivni i/ili psihijatrijski poremećaj odabran od blagog kognitivnog oštećenja, depresije, bipolarnog poremećaja, manije, shizofrenije, psihoze, anksioznosti i ovisnosti.
22. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest urogenitalni poremećaj.
23. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest gastrointestinalni poremećaj.
24. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema bilo kojem od patentnih zahtjeva 11 i 16 do 23, pri čemu je rečeni spoj kombiniran s jednim ili više drugih terapeutskih sredstava.
25. Farmaceutski pripravak koji sadrži, kao aktivnu tvar, spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 zajedno s farmaceutski prihvatljivim terapeutski inertnim organskim ili anorganskim materijalima za nosač.
26. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 21, pri čemu je rečeni spoj kombiniran s jednim ili više drugih terapeutskih sredstava prema patentnom zahtjevu 24, pri čemu je drugo terapeutsko sredstvo tipično ili atipično antipsihotičko sredstvo.
27. Spoj iz patentnog zahtjeva 26 naznačeno time da tipično antipsihotičko sredstvo jest haloperidol, a atipično antipsihotičko sredstvo odabrano je od risperidona i klozapina.
28. Spoj iz patentnog zahtjeva 26, naznačeno time da rečeni spoj jest 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid ili njegova farmaceutski prihvatljiva sol, tipično antipsihotičko sredstvo jest haloperidol, a atipično antipsihotičko sredstvo odabrano je od risperidona i klozapina.
29. Spoj iz patentnog zahtjeva 26, naznačeno time da rečeni spoj jest hidroklorid ili metansulfonat 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamida te tipično antipsihotičko sredstvo jest haloperidol, a atipično antipsihotičko sredstvo odabrano je od risperidona i klozapina.
30. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 20, pri čemu poremećaj jest poremećaj imunološkog sustava.
31. Spoj iz patentnog zahtjeva 30, naznačeno time da poremećaj imunološkog sustava jest multipla skleroza ili drugi demijelinizirajući poremećaji.
32. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema bilo kojem od patentnih zahtjeva 11 do 24 i 26 do 31 gdje su pacijenti koji pate od poremećaja (poremećaja) posebno osjetljivi na neželjene nuspojave zbog MAO inhibitorske aktivnosti.
33. Upotreba spoja iz bilo kojeg od patentnih zahtjeva 1 do 9 za pripravu lijeka aktivnog kao modulator natrijevog i/ili kalcijevog kanala za liječenje patologija u kojima gore rečeni mehanizam (mehanizimi) igra (igraju) patološku ulogu, koja je neurološki, kognitivni, psihijatrijski, upalni, urogenitalni ili gastrointestinalni poremećaj, a rečeni lijek uopće nema MAO inhibitorsku aktivnost ili ima znatno smanjenu MAO inhibitorsku aktivnost.
34. Upotreba prema patentnom zahtjevu 33 pri čemu poremećaj jest kao u bilo kojem od patentnih zahtjeva 16 do 23.
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EP07011766 | 2007-06-15 | ||
PCT/EP2008/003848 WO2008151702A1 (en) | 2007-06-15 | 2008-05-14 | Substituted 2- [2- (phenyl) ethylamino] alkaneamide derivatives and their use as sodium and/or calcium channel modulators |
EP08749449.8A EP2155663B1 (en) | 2007-06-15 | 2008-05-14 | Substituted 2-[2-(phenyl)ethylamino]alkaneamide derivatives and their use as sodium and/or calcium channel modulators |
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US (8) | US8519000B2 (hr) |
EP (1) | EP2155663B1 (hr) |
JP (1) | JP5440496B2 (hr) |
KR (1) | KR101545124B1 (hr) |
CN (1) | CN101687773B (hr) |
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CY (1) | CY1119787T1 (hr) |
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EA (1) | EA018195B1 (hr) |
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HU (1) | HUE038113T2 (hr) |
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PL (1) | PL2155663T3 (hr) |
PT (1) | PT2155663T (hr) |
RS (1) | RS56780B1 (hr) |
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PL2723710T3 (pl) * | 2011-06-27 | 2017-02-28 | Newron Pharmaceuticals S.P.A. | Fluorowane pochodne aryloalkiloaminokarboksyamidowe |
CN103804341B (zh) * | 2012-11-13 | 2018-04-10 | 中国人民解放军军事医学科学院毒物药物研究所 | 酰胺衍生物及其医药用途 |
CN104761531B (zh) * | 2014-01-03 | 2017-12-01 | 中国人民解放军军事医学科学院毒物药物研究所 | 镇痛活性化合物及其医药用途 |
CA3004448A1 (en) * | 2015-11-12 | 2017-05-18 | Afasci, Inc. | Ion channel inhibitory compounds, pharmaceutical formulations and uses |
CN106316824B (zh) * | 2016-08-18 | 2018-10-19 | 广州康瑞泰药业有限公司 | 一种合成2-氟环丙烷甲酸的新方法 |
CN112041296B (zh) * | 2018-04-28 | 2023-12-29 | 上海璃道医药科技有限公司 | 包含苯并含氧脂肪环结构的氨基乙酰胺类化合物及其用途 |
DE112019004296T5 (de) * | 2018-08-30 | 2021-07-22 | Sabic Global Technologies B.V. | Aromatisierungskatalysator mit verbesserter isomerisierung, herstellungsverfahren und verwendung davon |
EP3725769A1 (en) * | 2019-04-17 | 2020-10-21 | Newron Pharmaceuticals S.p.A. | Process for the production of substituted 2-[2-(phenyl) ethylamino]alkaneamide derivatives |
EP3725768A1 (en) * | 2019-04-17 | 2020-10-21 | Newron Pharmaceuticals S.p.A. | Process for the production of substituted 2-[2-(phenyl) ethylamino]alkaneamide derivatives |
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