NO329583B1 - Anvendelse av (R)-(-)-2[5-(4-fluorfenyl)-3-pyridylmetylaminometyl]kroman og dets fysiologisk akseptable salter til fremstilling av medikamenter, samt farmasoytiske preparater som omfatter forbindelsene og minst ett legemiddel mot Parkinsonssykdom - Google Patents
Anvendelse av (R)-(-)-2[5-(4-fluorfenyl)-3-pyridylmetylaminometyl]kroman og dets fysiologisk akseptable salter til fremstilling av medikamenter, samt farmasoytiske preparater som omfatter forbindelsene og minst ett legemiddel mot Parkinsonssykdom Download PDFInfo
- Publication number
- NO329583B1 NO329583B1 NO20024291A NO20024291A NO329583B1 NO 329583 B1 NO329583 B1 NO 329583B1 NO 20024291 A NO20024291 A NO 20024291A NO 20024291 A NO20024291 A NO 20024291A NO 329583 B1 NO329583 B1 NO 329583B1
- Authority
- NO
- Norway
- Prior art keywords
- pyridylmethylaminomethyl
- fluorophenyl
- chromane
- disease
- parkinson
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 109
- 239000003814 drug Substances 0.000 title claims abstract description 90
- 229940079593 drug Drugs 0.000 title claims description 81
- 208000018737 Parkinson disease Diseases 0.000 title claims description 66
- 238000002360 preparation method Methods 0.000 title claims description 44
- 150000001875 compounds Chemical class 0.000 title description 23
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- HKFMQJUJWSFOLY-OAQYLSRUSA-N sarizotan Chemical compound C1=CC(F)=CC=C1C1=CN=CC(CNC[C@@H]2OC3=CC=CC=C3CC2)=C1 HKFMQJUJWSFOLY-OAQYLSRUSA-N 0.000 claims abstract description 102
- 238000011282 treatment Methods 0.000 claims abstract description 71
- 208000016285 Movement disease Diseases 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 230000000694 effects Effects 0.000 claims description 29
- 208000012661 Dyskinesia Diseases 0.000 claims description 27
- 206010044565 Tremor Diseases 0.000 claims description 24
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 17
- 206010034010 Parkinsonism Diseases 0.000 claims description 16
- 206010008748 Chorea Diseases 0.000 claims description 15
- 230000000632 dystonic effect Effects 0.000 claims description 15
- 230000009931 harmful effect Effects 0.000 claims description 15
- 208000011580 syndromic disease Diseases 0.000 claims description 12
- 208000002033 Myoclonus Diseases 0.000 claims description 10
- 208000027776 Extrapyramidal disease Diseases 0.000 claims description 8
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 8
- 206010058504 Ballismus Diseases 0.000 claims description 7
- 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 7
- 208000018839 Wilson disease Diseases 0.000 claims description 7
- 229960000911 benserazide Drugs 0.000 claims description 5
- BNQDCRGUHNALGH-UHFFFAOYSA-N benserazide Chemical compound OCC(N)C(=O)NNCC1=CC=C(O)C(O)=C1O BNQDCRGUHNALGH-UHFFFAOYSA-N 0.000 claims description 5
- 229960004205 carbidopa Drugs 0.000 claims description 3
- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 claims description 3
- QDLVYMYXOLGZOD-ZMBIFBSDSA-N [(2r)-3,4-dihydro-2h-chromen-2-yl]methyl-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]azanium;chloride Chemical group Cl.C1=CC(F)=CC=C1C1=CN=CC(CNC[C@@H]2OC3=CC=CC=C3CC2)=C1 QDLVYMYXOLGZOD-ZMBIFBSDSA-N 0.000 abstract description 32
- 230000002939 deleterious effect Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 21
- 241000700159 Rattus Species 0.000 description 14
- 238000010171 animal model Methods 0.000 description 13
- 208000001089 Multiple system atrophy Diseases 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 208000024891 symptom Diseases 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- 208000028017 Psychotic disease Diseases 0.000 description 9
- 208000012601 choreatic disease Diseases 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 208000023105 Huntington disease Diseases 0.000 description 8
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 241000282693 Cercopithecidae Species 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000902 placebo Substances 0.000 description 7
- 229940068196 placebo Drugs 0.000 description 7
- 206010044074 Torticollis Diseases 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- WBLZUCOIBUDNBV-UHFFFAOYSA-N 3-nitropropanoic acid Chemical compound OC(=O)CC[N+]([O-])=O WBLZUCOIBUDNBV-UHFFFAOYSA-N 0.000 description 5
- 206010001540 Akathisia Diseases 0.000 description 5
- 208000009132 Catalepsy Diseases 0.000 description 5
- 208000014094 Dystonic disease Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 208000001431 Psychomotor Agitation Diseases 0.000 description 5
- 206010047853 Waxy flexibility Diseases 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 208000010118 dystonia Diseases 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 206010001541 Akinesia Diseases 0.000 description 4
- 102000004073 Dopamine D3 Receptors Human genes 0.000 description 4
- 108090000525 Dopamine D3 Receptors Proteins 0.000 description 4
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 4
- 208000016620 Tourette disease Diseases 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 206010005159 blepharospasm Diseases 0.000 description 4
- 230000000744 blepharospasm Effects 0.000 description 4
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 4
- 229960002495 buspirone Drugs 0.000 description 4
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 4
- 229960004170 clozapine Drugs 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 4
- 229960003878 haloperidol Drugs 0.000 description 4
- 230000001537 neural effect Effects 0.000 description 4
- 239000003176 neuroleptic agent Substances 0.000 description 4
- 230000000422 nocturnal effect Effects 0.000 description 4
- 201000002212 progressive supranuclear palsy Diseases 0.000 description 4
- 238000007619 statistical method Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- PLRACCBDVIHHLZ-UHFFFAOYSA-N 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1N(C)CCC(C=2C=CC=CC=2)=C1 PLRACCBDVIHHLZ-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 102000015554 Dopamine receptor Human genes 0.000 description 3
- 108050004812 Dopamine receptor Proteins 0.000 description 3
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 3
- 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 3
- 206010049816 Muscle tightness Diseases 0.000 description 3
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 3
- 208000024453 abnormal involuntary movement Diseases 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 230000000648 anti-parkinson Effects 0.000 description 3
- 239000000939 antiparkinson agent Substances 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229940052760 dopamine agonists Drugs 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 201000006517 essential tremor Diseases 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000002151 myoclonic effect Effects 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 230000021542 voluntary musculoskeletal movement Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
- 208000019352 Blepharospasm-oromandibular dystonia syndrome Diseases 0.000 description 2
- 206010006100 Bradykinesia Diseases 0.000 description 2
- 108020002739 Catechol O-methyltransferase Proteins 0.000 description 2
- 102000006378 Catechol O-methyltransferase Human genes 0.000 description 2
- 208000011990 Corticobasal Degeneration Diseases 0.000 description 2
- 241000699800 Cricetinae Species 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- 208000010496 Heart Arrest Diseases 0.000 description 2
- 208000006083 Hypokinesia Diseases 0.000 description 2
- 241000282567 Macaca fascicularis Species 0.000 description 2
- 201000005190 Meige syndrome Diseases 0.000 description 2
- 102000010909 Monoamine Oxidase Human genes 0.000 description 2
- 108010062431 Monoamine oxidase Proteins 0.000 description 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
- 208000009106 Shy-Drager Syndrome Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000003270 anti-cataleptic effect Effects 0.000 description 2
- 230000001090 anti-dopaminergic effect Effects 0.000 description 2
- 230000000561 anti-psychotic effect Effects 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 210000000548 hind-foot Anatomy 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 230000037230 mobility Effects 0.000 description 2
- 210000001577 neostriatum Anatomy 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 208000031237 olivopontocerebellar atrophy Diseases 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 230000000284 resting effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000007940 sugar coated tablet Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- ANXOJXYTTDGHAJ-GHVWMZMZSA-N 1-[(2r)-3,4-dihydro-2h-chromen-2-yl]-n-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]methanamine;dihydrochloride Chemical compound Cl.Cl.C1=CC(F)=CC=C1C1=CN=CC(CNC[C@@H]2OC3=CC=CC=C3CC2)=C1 ANXOJXYTTDGHAJ-GHVWMZMZSA-N 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- 206010000599 Acromegaly Diseases 0.000 description 1
- 201000010000 Agranulocytosis Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 108030001720 Bontoxilysin Proteins 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 description 1
- 206010008027 Cerebellar atrophy Diseases 0.000 description 1
- 208000018152 Cerebral disease Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010011953 Decreased activity Diseases 0.000 description 1
- 229940123603 Dopamine D2 receptor antagonist Drugs 0.000 description 1
- 206010017577 Gait disturbance Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010071602 Genetic polymorphism Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010058359 Hypogonadism Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010052904 Musculoskeletal stiffness Diseases 0.000 description 1
- 208000011644 Neurologic Gait disease Diseases 0.000 description 1
- 101710138657 Neurotoxin Proteins 0.000 description 1
- 206010069917 Orthostatic tremor Diseases 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- -1 alkylene glycols Chemical class 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 229960003805 amantadine Drugs 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003374 anti-dyskinetic effect Effects 0.000 description 1
- 229940125713 antianxiety drug Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003935 attention Effects 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940053031 botulinum toxin Drugs 0.000 description 1
- 229960002802 bromocriptine Drugs 0.000 description 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
- 229960002452 budipine Drugs 0.000 description 1
- QIHLUZAFSSMXHQ-UHFFFAOYSA-N budipine Chemical compound C1CN(C(C)(C)C)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 QIHLUZAFSSMXHQ-UHFFFAOYSA-N 0.000 description 1
- 229960004596 cabergoline Drugs 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 201000002866 cervical dystonia Diseases 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000000442 dopamine 2 receptor blocking agent Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960003337 entacapone Drugs 0.000 description 1
- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 description 1
- 229960003133 ergot alkaloid Drugs 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000003370 grooming effect Effects 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000018197 inherited torticollis Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000003447 ipsilateral effect Effects 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229960003587 lisuride Drugs 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000007087 memory ability Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- 230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 239000002581 neurotoxin Substances 0.000 description 1
- 231100000618 neurotoxin Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 229960004851 pergolide Drugs 0.000 description 1
- YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229960003089 pramipexole Drugs 0.000 description 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960001879 ropinirole Drugs 0.000 description 1
- UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
- 229960003946 selegiline Drugs 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 230000003997 social interaction Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000011301 standard therapy Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 208000003755 striatonigral degeneration Diseases 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960004603 tolcapone Drugs 0.000 description 1
- MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 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
- 229960002622 triacetin Drugs 0.000 description 1
- 230000028838 turning behavior Effects 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 230000009184 walking Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4433—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00104531 | 2000-03-10 | ||
PCT/EP2001/001038 WO2001068063A2 (en) | 2000-03-10 | 2001-02-01 | Novel use of (r)-(-)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]-chromane and its physiologically acceptable salts |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20024291L NO20024291L (no) | 2002-09-09 |
NO20024291D0 NO20024291D0 (no) | 2002-09-09 |
NO329583B1 true NO329583B1 (no) | 2010-11-15 |
Family
ID=8168017
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20024291A NO329583B1 (no) | 2000-03-10 | 2002-09-09 | Anvendelse av (R)-(-)-2[5-(4-fluorfenyl)-3-pyridylmetylaminometyl]kroman og dets fysiologisk akseptable salter til fremstilling av medikamenter, samt farmasoytiske preparater som omfatter forbindelsene og minst ett legemiddel mot Parkinsonssykdom |
Country Status (29)
Country | Link |
---|---|
US (1) | US7928128B2 (es) |
EP (2) | EP1299099B1 (es) |
JP (1) | JP4901046B2 (es) |
KR (1) | KR100830139B1 (es) |
CN (1) | CN1188123C (es) |
AR (1) | AR033807A1 (es) |
AT (1) | ATE307578T1 (es) |
AU (2) | AU2001230222C1 (es) |
BR (1) | BR0109119A (es) |
CA (1) | CA2402402C (es) |
CO (1) | CO5271686A1 (es) |
CZ (1) | CZ301807B6 (es) |
DE (1) | DE60114419T2 (es) |
DK (1) | DK1299099T3 (es) |
ES (1) | ES2251460T3 (es) |
HK (1) | HK1054198B (es) |
HU (1) | HU229309B1 (es) |
ME (1) | MEP5608A (es) |
MX (1) | MXPA02008800A (es) |
MY (1) | MY136976A (es) |
NO (1) | NO329583B1 (es) |
PL (1) | PL200781B1 (es) |
RS (1) | RS51316B (es) |
RU (1) | RU2278663C2 (es) |
SI (1) | SI1299099T1 (es) |
SK (1) | SK286933B6 (es) |
UA (1) | UA73981C2 (es) |
WO (1) | WO2001068063A2 (es) |
ZA (1) | ZA200208133B (es) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UA73981C2 (en) | 2000-03-10 | 2005-10-17 | Merck Patent Gmbh | (r)-(-)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]-chromane for treatment of extrapyramidal movement disorders (variants), pharmaceutical composition and kit |
CN1292749C (zh) * | 2001-07-26 | 2007-01-03 | 默克专利股份有限公司 | 2-[5-(4-氟苯基)-3-吡啶基甲氨基甲基]苯并二氢吡喃及其生理学上可接受的盐的新用途 |
PT1427724E (pt) * | 2001-09-19 | 2006-09-29 | Merck Patent Gmbh | Utilizacao nova de aminometilcromanos substituidos |
EP1896021B1 (de) * | 2005-06-21 | 2009-04-15 | Merck Patent GmbH | Feste pharmazeutische zubereitung enthaltend (r)-(-)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]-chroman |
US9066903B2 (en) | 2006-02-28 | 2015-06-30 | The United States Of America As Represented By The Department Of Veterans Affairs | Pharmacological treatment of Parkinson's disease |
US10010515B2 (en) | 2011-03-01 | 2018-07-03 | Pharnext | Therapeutic approaches for treating Parkinson's disease |
US9248111B2 (en) * | 2011-03-01 | 2016-02-02 | Pharnext | Therapeutic approaches for treating parkinson's disease |
CN108937972A (zh) * | 2018-06-08 | 2018-12-07 | 青岛大学附属医院 | 一种多特征融合的就诊用户情绪监控方法 |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2364685C3 (de) | 1973-12-27 | 1978-06-15 | Beiersdorf Ag, 2000 Hamburg | Phenoxyäthylamine |
US4438119A (en) * | 1982-12-23 | 1984-03-20 | Mead Johnson & Company | Method for alleviation of extrapyramidal motor disorders |
CA1337429C (en) | 1983-12-05 | 1995-10-24 | Guy Rosalia Eugene Van Lommen | Derivatives of 2,2'-iminobisethanol |
SE460947B (sv) * | 1986-08-26 | 1989-12-11 | Lejus Medical Ab | En multiple-unit-dos komposition av l-dopa |
DE3901814A1 (de) * | 1988-07-28 | 1990-02-01 | Bayer Ag | Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga |
DE69123090D1 (de) * | 1990-07-06 | 1996-12-19 | Yoshitomi Pharmaceutical | Kondensierte Thiophenverbindungen und deren Verwendung |
DE4135474A1 (de) * | 1991-10-28 | 1993-04-29 | Bayer Ag | 2-aminomethyl-chromane |
US5314888A (en) * | 1992-02-21 | 1994-05-24 | Trustees Of Tufts College | Veterinary method for treating inappropriate elimination of urine in household pets |
SI9300097B (en) | 1992-02-27 | 2001-12-31 | Janssen Pharmaceutica Nv | (benzodioxan, benzofuran or benzopyran) alkylamino) alkyl substituted guanidines |
JPH07507058A (ja) * | 1992-03-11 | 1995-08-03 | インターニューロン ファーマシューティカルズ,インコーポレーテッド | 大型の中性アミノ酸(lnaa)の血中濃度の食後変動の低減 |
DE4226527A1 (de) | 1992-08-11 | 1994-02-17 | Merck Patent Gmbh | 1,4-Benzodioxanderivate |
JPH08503448A (ja) * | 1992-12-07 | 1996-04-16 | メレルダウファーマス−ティカルズ インコーポレイテッド | 5ht▲下1▼▲a▼受容体アゴニストによる不随意運動の処置 |
GB9302622D0 (en) | 1993-02-10 | 1993-03-24 | Wellcome Found | Heteroaromatic compounds |
JPH09509398A (ja) * | 1993-11-19 | 1997-09-22 | ザ ボード オブ ガヴァナーズ フォー ハイアー エデュケーション,ステイト オブ ロードアイランド アンド プロヴィデンス プランテーションズ | オクタヒドロベンゾ[f]キノリン系受容体アゴニストおよびアンタゴニスト |
IL114027A (en) | 1994-06-08 | 1999-11-30 | Lundbeck & Co As H | 4-Phenyl piperazine (piperidine or tetrahydropyridine) derivatives serotinin 5-HT1A and dopamin D2 receptor ligand pharmaceutical compositions containing them |
FR2723091B1 (fr) * | 1994-07-29 | 1996-11-08 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
SI0707007T1 (en) * | 1994-10-14 | 2002-04-30 | Merck Patent Gmbh | (R)-(-)-2-(5-(4-fluorophenyl)-3-pyridylmethylaminomethyl)chromane as CNS active agent |
US5502080A (en) * | 1994-11-01 | 1996-03-26 | Hitzig; Pietr | Combined use of dopamine and serotonin agonists in the treatment of allergic disorders |
US5554383A (en) * | 1995-04-06 | 1996-09-10 | Trustees Of Tufts College | Veterinary method for clinically modifying the behavior of dogs exhibiting canine affective aggression |
US5541199A (en) * | 1995-06-02 | 1996-07-30 | American Home Products Corporation | Chroman-2-ylmethylamino derivatives |
GB9514380D0 (en) | 1995-07-13 | 1995-09-13 | Knoll Ag | Therapeutic agents |
AU6517196A (en) * | 1995-07-13 | 1997-02-10 | Knoll Aktiengesellschaft | Piperazine derivatives as therapeutic agents |
US5670667A (en) * | 1995-07-25 | 1997-09-23 | American Home Products Corporation | Chroman-2-ylmethylamino derivatives |
US5756521A (en) * | 1996-04-03 | 1998-05-26 | American Home Products Corporation | Chroman-2-ylmethylamino derivatives |
DE19648384A1 (de) | 1996-11-22 | 1998-05-28 | Merck Patent Gmbh | Fluorene, Dibenzofurane und Dibenzothiophene |
EP0900792B1 (en) | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists |
DE69819266T2 (de) * | 1997-09-02 | 2004-07-29 | Duphar International Research B.V. | Piperidin- und Piperazin Derivate als 5-HT1-Rezeptor-Agonisten |
DE19751949A1 (de) * | 1997-11-24 | 1999-05-27 | Bayer Ag | Verwendung von substituierten Aminomethyl-Chromanen zur Verhinderung der neuronalen Degeneration und zur Förderung der neuronalen Regeneration |
WO1999045906A1 (en) | 1998-03-09 | 1999-09-16 | Trustees Of Tufts College | Treatment of compulsive behaviours in man and animals |
US6136861A (en) * | 1998-03-17 | 2000-10-24 | Pfizer Inc | Bicyclo[2.2.1]heptanes and related compounds |
FR2781671A1 (fr) * | 1998-07-28 | 2000-02-04 | Synthelabo | Compositions pharmaceutiques contenant un inhibiteur de la recapture de la serotonine et leur application en therapeutique |
UA71590C2 (en) | 1998-11-13 | 2004-12-15 | Duphar Int Res | Piperazine and piperidine derivatives |
UA73981C2 (en) | 2000-03-10 | 2005-10-17 | Merck Patent Gmbh | (r)-(-)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]-chromane for treatment of extrapyramidal movement disorders (variants), pharmaceutical composition and kit |
-
2001
- 2001-01-02 UA UA2002108054A patent/UA73981C2/uk unknown
- 2001-02-01 US US10/221,031 patent/US7928128B2/en not_active Expired - Fee Related
- 2001-02-01 MX MXPA02008800A patent/MXPA02008800A/es active IP Right Grant
- 2001-02-01 HU HU0300079A patent/HU229309B1/hu not_active IP Right Cessation
- 2001-02-01 DE DE60114419T patent/DE60114419T2/de not_active Expired - Lifetime
- 2001-02-01 ES ES01902375T patent/ES2251460T3/es not_active Expired - Lifetime
- 2001-02-01 CA CA2402402A patent/CA2402402C/en not_active Expired - Fee Related
- 2001-02-01 EP EP01902375A patent/EP1299099B1/en not_active Expired - Lifetime
- 2001-02-01 EP EP05022178A patent/EP1645273A3/en not_active Withdrawn
- 2001-02-01 BR BR0109119-0A patent/BR0109119A/pt not_active Application Discontinuation
- 2001-02-01 AU AU2001230222A patent/AU2001230222C1/en not_active Ceased
- 2001-02-01 JP JP2001566627A patent/JP4901046B2/ja not_active Expired - Fee Related
- 2001-02-01 ME MEP-56/08A patent/MEP5608A/xx unknown
- 2001-02-01 CZ CZ20022951A patent/CZ301807B6/cs not_active IP Right Cessation
- 2001-02-01 KR KR1020027011793A patent/KR100830139B1/ko not_active IP Right Cessation
- 2001-02-01 WO PCT/EP2001/001038 patent/WO2001068063A2/en active IP Right Grant
- 2001-02-01 AT AT01902375T patent/ATE307578T1/de active
- 2001-02-01 CN CNB018062725A patent/CN1188123C/zh not_active Expired - Fee Related
- 2001-02-01 RU RU2002127006/15A patent/RU2278663C2/ru not_active IP Right Cessation
- 2001-02-01 DK DK01902375T patent/DK1299099T3/da active
- 2001-02-01 SK SK1264-2002A patent/SK286933B6/sk not_active IP Right Cessation
- 2001-02-01 PL PL356428A patent/PL200781B1/pl not_active IP Right Cessation
- 2001-02-01 RS YUP-674/02A patent/RS51316B/sr unknown
- 2001-02-01 AU AU3022201A patent/AU3022201A/xx active Pending
- 2001-02-01 SI SI200130475T patent/SI1299099T1/sl unknown
- 2001-03-07 MY MYPI20011030A patent/MY136976A/en unknown
- 2001-03-09 AR ARP010101105A patent/AR033807A1/es unknown
- 2001-03-12 CO CO01019802A patent/CO5271686A1/es not_active Application Discontinuation
-
2002
- 2002-09-09 NO NO20024291A patent/NO329583B1/no not_active IP Right Cessation
- 2002-10-09 ZA ZA200208133A patent/ZA200208133B/en unknown
-
2003
- 2003-09-11 HK HK03106499.0A patent/HK1054198B/zh not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2455621C (en) | Use of (r/s)-(-/+) or (s)-(+)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]chromane for the treatment of extrapyramidal movement disorders | |
NO329583B1 (no) | Anvendelse av (R)-(-)-2[5-(4-fluorfenyl)-3-pyridylmetylaminometyl]kroman og dets fysiologisk akseptable salter til fremstilling av medikamenter, samt farmasoytiske preparater som omfatter forbindelsene og minst ett legemiddel mot Parkinsonssykdom | |
AU2002355170A1 (en) | Novel use of 2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]-chromane and its physiologically acceptable salts | |
AU2001230222A1 (en) | Novel use of (R)-(-)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]- chromane and its physiologically acceptable salts | |
EP1425008B1 (en) | Use of substituted aminomethyl chromans in the treatment of side effects of neuroleptics | |
AU2002331220A1 (en) | Novel use of substituted aminomethyl chromans for the treatment of movement disorder and of adverse effects induced by drugs administered to treat extrapyramidal movement disorders | |
ZA200401592B (en) | Novel use of 2-[5- (4-fluorophenyl)-3-pyridylmethylaminomethyl} -chromane and its physiologically acceptable salts |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |