NO322120B1 - Anvendelse av 1-[4-(5-cyanindol-3-yl)butyl]-4-(2-karbamoylbenzofuran-5-yl)-piperazin og dets fysiologisk akseptable salter til fremstilling av medikamenter for behandling av angstforstyrrelser av undertype - Google Patents
Anvendelse av 1-[4-(5-cyanindol-3-yl)butyl]-4-(2-karbamoylbenzofuran-5-yl)-piperazin og dets fysiologisk akseptable salter til fremstilling av medikamenter for behandling av angstforstyrrelser av undertype Download PDFInfo
- Publication number
- NO322120B1 NO322120B1 NO20015746A NO20015746A NO322120B1 NO 322120 B1 NO322120 B1 NO 322120B1 NO 20015746 A NO20015746 A NO 20015746A NO 20015746 A NO20015746 A NO 20015746A NO 322120 B1 NO322120 B1 NO 322120B1
- Authority
- NO
- Norway
- Prior art keywords
- butyl
- piperazine
- cyanindol
- carbamoylbenzofuran
- treatment
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 31
- 238000011282 treatment Methods 0.000 title claims description 23
- SGEGOXDYSFKCPT-UHFFFAOYSA-N vilazodone Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)N)=CNC2=C1 SGEGOXDYSFKCPT-UHFFFAOYSA-N 0.000 title claims description 20
- 208000019901 Anxiety disease Diseases 0.000 title claims description 19
- 239000003814 drug Substances 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 10
- 229940079593 drug Drugs 0.000 title description 9
- 208000008811 Agoraphobia Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 208000019906 panic disease Diseases 0.000 claims description 8
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 8
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 5
- 206010041250 Social phobia Diseases 0.000 claims description 5
- 230000037328 acute stress Effects 0.000 claims description 5
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 5
- 238000001228 spectrum Methods 0.000 claims description 5
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 28
- 238000012360 testing method Methods 0.000 description 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
- 241000700159 Rattus Species 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 241000699666 Mus <mouse, genus> Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229960005141 piperazine Drugs 0.000 description 9
- 239000000018 receptor agonist Substances 0.000 description 9
- 229940044601 receptor agonist Drugs 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- TZJUVVIWVWFLCD-UHFFFAOYSA-N 1,1-dioxo-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 TZJUVVIWVWFLCD-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 230000036506 anxiety Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 229950003599 ipsapirone Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000035882 stress Effects 0.000 description 5
- 206010029897 Obsessive thoughts Diseases 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 208000030459 obsessive-compulsive personality disease Diseases 0.000 description 4
- 208000007656 osteochondritis dissecans Diseases 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 230000003997 social interaction Effects 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 3
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 3
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 3
- 239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 230000002426 anti-panic effect Effects 0.000 description 3
- 238000009933 burial Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 229960002464 fluoxetine Drugs 0.000 description 3
- 229960004038 fluvoxamine Drugs 0.000 description 3
- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- RPZBRGFNBNQSOP-UHFFFAOYSA-N vilazodone hydrochloride Chemical compound Cl.C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)N)=CNC2=C1 RPZBRGFNBNQSOP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ASXGJMSKWNBENU-UHFFFAOYSA-N 8-OH-DPAT Chemical compound C1=CC(O)=C2CC(N(CCC)CCC)CCC2=C1 ASXGJMSKWNBENU-UHFFFAOYSA-N 0.000 description 2
- 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 208000028017 Psychotic disease 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
- 230000009471 action Effects 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 230000007123 defense Effects 0.000 description 2
- 239000012154 double-distilled water Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000007940 sugar coated tablet Substances 0.000 description 2
- 239000013589 supplement 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
- 238000005406 washing Methods 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-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
- CPXKXLSFUJLYFN-UHFFFAOYSA-N 8-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N(CCC)CCC)CCCC2=C1 CPXKXLSFUJLYFN-UHFFFAOYSA-N 0.000 description 1
- 206010000599 Acromegaly Diseases 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 208000036640 Asperger disease Diseases 0.000 description 1
- 201000006062 Asperger syndrome Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 206010063659 Aversion Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 208000018152 Cerebral disease Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 241001480592 Chlorophyllum molybdites Species 0.000 description 1
- 206010008748 Chorea Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 206010013980 Dyssomnias Diseases 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 208000001836 Firesetting Behavior Diseases 0.000 description 1
- 208000001613 Gambling Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010060891 General symptom Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 201000001916 Hypochondriasis Diseases 0.000 description 1
- 206010058359 Hypogonadism Diseases 0.000 description 1
- 208000030990 Impulse-control disease Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 206010034158 Pathological gambling Diseases 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 208000027520 Somatoform disease 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
- 208000027522 Sydenham chorea Diseases 0.000 description 1
- 206010044074 Torticollis Diseases 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- -1 alkylene glycols Chemical class 0.000 description 1
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000002377 anti-obsessional effect Effects 0.000 description 1
- 208000024823 antisocial personality disease Diseases 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 238000013542 behavioral therapy 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
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960002495 buspirone Drugs 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 238000004140 cleaning Methods 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
- 231100000867 compulsive behavior Toxicity 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 208000018459 dissociative disease Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000011977 dual antiplatelet therapy Methods 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 208000003481 exhibitionism Diseases 0.000 description 1
- 230000021824 exploration behavior Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 206010016531 fetishism Diseases 0.000 description 1
- NYSDRDDQELAVKP-SFHVURJKSA-N flesinoxan Chemical compound C([C@@H](O1)CO)OC2=C1C=CC=C2N(CC1)CCN1CCNC(=O)C1=CC=C(F)C=C1 NYSDRDDQELAVKP-SFHVURJKSA-N 0.000 description 1
- 229950003678 flesinoxan Drugs 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
- QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 description 1
- 229960000647 gepirone Drugs 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 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
- 238000001990 intravenous administration Methods 0.000 description 1
- 206010023461 kleptomania Diseases 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 230000001537 neural effect Effects 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
- 230000002290 panicolytic effect Effects 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 238000011302 passive avoidance test Methods 0.000 description 1
- 208000022821 personality disease Diseases 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 201000004645 pyromania Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012502 risk assessment Methods 0.000 description 1
- 208000022610 schizoaffective disease Diseases 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000003723 serotonin 1A agonist Substances 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000024188 startle response Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 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
- 238000012956 testing procedure Methods 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
- 208000002271 trichotillomania Diseases 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
- 208000008918 voyeurism Diseases 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
-
- 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
- A61K31/495—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
-
- 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
- A61K31/495—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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Reproductive Health (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Gynecology & Obstetrics (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Pregnancy & Childbirth (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Child & Adolescent Psychology (AREA)
- Nutrition Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99109295 | 1999-05-27 | ||
| PCT/EP2000/004376 WO2000072832A2 (en) | 1999-05-27 | 2000-05-16 | Novel use of 1-[4-(cyanoindol-3yl)butyl]-4-(carbamoyl-benzofuran-5yl)-piperazine and its physiologically acceptable salts |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20015746D0 NO20015746D0 (no) | 2001-11-26 |
| NO20015746L NO20015746L (no) | 2001-11-26 |
| NO322120B1 true NO322120B1 (no) | 2006-08-14 |
Family
ID=8238153
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20015746A NO322120B1 (no) | 1999-05-27 | 2001-11-26 | Anvendelse av 1-[4-(5-cyanindol-3-yl)butyl]-4-(2-karbamoylbenzofuran-5-yl)-piperazin og dets fysiologisk akseptable salter til fremstilling av medikamenter for behandling av angstforstyrrelser av undertype |
| NO20061562A NO324230B1 (no) | 1999-05-27 | 2006-04-06 | Anvendelse av 1- [4-(5-cyanindol-3yl)butyl ]-4-(2-karbamoylbenzofuran-5-yl)-piperazin og dets fysiologisk akseptable salter til fremstilling av medikamenter for behandling av bipolare forstyrrelser og mani |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20061562A NO324230B1 (no) | 1999-05-27 | 2006-04-06 | Anvendelse av 1- [4-(5-cyanindol-3yl)butyl ]-4-(2-karbamoylbenzofuran-5-yl)-piperazin og dets fysiologisk akseptable salter til fremstilling av medikamenter for behandling av bipolare forstyrrelser og mani |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US6900212B1 (sl) |
| EP (3) | EP1185272B1 (sl) |
| JP (2) | JP4884588B2 (sl) |
| KR (1) | KR100683367B1 (sl) |
| CN (3) | CN101869565A (sl) |
| AR (1) | AR024112A1 (sl) |
| AT (3) | ATE337008T1 (sl) |
| AU (1) | AU771778B2 (sl) |
| BR (1) | BR0010948A (sl) |
| CA (3) | CA2694866A1 (sl) |
| CY (2) | CY1105750T1 (sl) |
| CZ (1) | CZ295623B6 (sl) |
| DE (3) | DE60009697T2 (sl) |
| DK (3) | DK1185272T3 (sl) |
| ES (3) | ES2330774T3 (sl) |
| HK (1) | HK1048444B (sl) |
| HU (1) | HU229059B1 (sl) |
| IL (2) | IL146707A0 (sl) |
| MX (1) | MXPA01012172A (sl) |
| MY (1) | MY135627A (sl) |
| NO (2) | NO322120B1 (sl) |
| PL (3) | PL199650B1 (sl) |
| PT (3) | PT1185272E (sl) |
| RU (1) | RU2237477C2 (sl) |
| SI (2) | SI1185272T1 (sl) |
| SK (1) | SK287851B6 (sl) |
| TR (1) | TR200103361T2 (sl) |
| TW (1) | TW518218B (sl) |
| UA (1) | UA74337C2 (sl) |
| WO (1) | WO2000072832A2 (sl) |
| ZA (1) | ZA200110485B (sl) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW518218B (en) * | 1999-05-27 | 2003-01-21 | Merck Patent Gmbh | Pharmaceutical compositions comprising 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine or its physiologically acceptable salts for use in the treatment of sub-type anxiety disorders |
| UA76130C2 (en) * | 2000-11-20 | 2006-07-17 | Merck Patent Gmbh | Use of compounds combining properties of selective inhibitors of serotonin re-uptake and agonists of 5-ht1a receptor for treatment of irritable bowel syndrome |
| DE10112151A1 (de) | 2001-03-14 | 2002-09-19 | Merck Patent Gmbh | Substituierte Benzofuran-2-carbonsäureamide |
| UA76758C2 (uk) | 2001-06-19 | 2006-09-15 | Мерк Патент Гмбх | Поліморфні форми гідрохлориду 1-'4-(5-ціаноіндол-3-іл)бутил-4-(2-карбамоїлбензофуран-5-іл)піперазину |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| DE10305739A1 (de) * | 2003-02-11 | 2004-08-19 | Merck Patent Gmbh | Benzofuranderivate |
| US20040192730A1 (en) * | 2003-03-13 | 2004-09-30 | Dynogen Pharmaceuticals, Inc. | Methods of using compounds with combined 5-HT1A and SSRI activities as-needed to treat sexual dysfunction |
| EP1732610A2 (en) * | 2004-03-26 | 2006-12-20 | Baylor University | Targeted serotonin reuptake inhibitors |
| US8003676B2 (en) | 2006-05-30 | 2011-08-23 | Astrazeneca Ab | 1,3,4-oxadiazole derivatives as DGAT1 inhibitors |
| BRPI0821274A2 (pt) | 2007-12-20 | 2017-06-13 | Astrazeneca Ab | composto ou um sal, ou pró-droga farmaceuticamente aceitável do mesmo, uso do mesmo, método para tratar uma doença em um animal de sangue quente, e, composição farmacêutica |
| MX2011014018A (es) | 2009-06-19 | 2012-02-22 | Astrazeneca Ab | Pirazincarboxamidas como inhibidores de dgati. |
| CA2779442A1 (en) | 2009-11-06 | 2011-05-12 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating fibromyalgia syndrome |
| CA2779457C (en) | 2009-11-06 | 2017-10-17 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating attention-deficit/hyperactivity disorder |
| US9610274B2 (en) | 2010-06-30 | 2017-04-04 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating bipolar disorder |
| US8623913B2 (en) | 2010-06-30 | 2014-01-07 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating restless legs syndrome |
| TWI577377B (zh) * | 2010-09-16 | 2017-04-11 | Ｖｉｉｖ醫療保健公司 | 醫藥組合物 |
| US9708300B2 (en) | 2011-03-20 | 2017-07-18 | Cadila Healthcare Limited | Amorphous form of vilazodone hydrochloride and process for its preparation |
| CN102949364A (zh) * | 2011-08-30 | 2013-03-06 | 天津药物研究院 | 一种含有效成分盐酸维拉佐酮的缓释片 |
| US9382233B2 (en) | 2012-06-13 | 2016-07-05 | Apotex Inc. | Forms of vilazodone and processes for the preparation thereof |
| CN102860993A (zh) * | 2012-10-16 | 2013-01-09 | 北京诚创思达医药科技有限公司 | 一种盐酸维拉唑酮快速释放片剂及其制备方法 |
| WO2014064715A2 (en) | 2012-10-22 | 2014-05-01 | Cadila Healthcare Limited | Amorphous form of vilazodone hydrochloride and process for preparing thereof |
| CN102977083A (zh) * | 2012-12-17 | 2013-03-20 | 南京海纳医药科技有限公司 | 1-[4-(5-氰基吲哚-3-基)丁基]-4-(2-氨甲酰-苯并呋喃-5-基)-哌嗪盐酸盐的新晶型xⅶ及其制备方法 |
| MX2015009277A (es) | 2013-01-22 | 2015-12-11 | Vistagen Therapeutics Inc | Formas de dosificacion y usos terapauticos de l-4-cloro quinurenina. |
| EP2824104A1 (en) | 2013-07-12 | 2015-01-14 | Sandoz AG | Process for the preparation of form III of Vilazodone hydrochloride |
| PT3297619T (pt) * | 2015-05-22 | 2022-08-05 | Vistagen Therapeutics Inc | Utilizações terapêuticas de l-4-cloroquinurenina |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4333254A1 (de) * | 1993-09-30 | 1995-04-06 | Merck Patent Gmbh | Piperidine und Piperazine |
| GB9406857D0 (en) * | 1994-04-07 | 1994-06-01 | Sandoz Ltd | Improvements in or relating to organic compounds |
| DE19514567A1 (de) * | 1995-04-20 | 1996-10-24 | Merck Patent Gmbh | Benzofurane |
| US5763457A (en) * | 1995-11-13 | 1998-06-09 | Eli Lilly And Company | Method for treating anxiety |
| US5914394A (en) * | 1997-03-27 | 1999-06-22 | Millenium Pharmaceuticals, Inc. | Methods and compositions for the diagnosis and treatment of neuropsychiatric disorders |
| US5900420A (en) * | 1997-06-19 | 1999-05-04 | Cole; William L. | Method for treating chronic fatigue syndrome and fibromyalgia with buprenorphine |
| US6470933B1 (en) * | 1998-03-09 | 2002-10-29 | Pirelli Pneumatici S.P.A. | Tire containing at least part of an electrical current generator intended for the supply of sensors and/or other electrical devices present within the tire, and method for manufacture the said tire |
| 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 |
| TW518218B (en) * | 1999-05-27 | 2003-01-21 | Merck Patent Gmbh | Pharmaceutical compositions comprising 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine or its physiologically acceptable salts for use in the treatment of sub-type anxiety disorders |
| EP1291660A3 (en) * | 2001-09-11 | 2003-05-28 | Koyo Seiko Co., Ltd. | Magnetic pulser ring, magnetizing device and method, and bearing unit having a magnetic pulser ring |
| FR2844591B1 (fr) * | 2002-09-13 | 2005-04-15 | Arvinmeritor Light Vehicle Sys | Dispositif de determination du deplacement d'un arbre |
-
1999
- 1999-11-15 TW TW088119882A patent/TW518218B/zh not_active IP Right Cessation
-
2000
- 2000-05-16 CZ CZ20014226A patent/CZ295623B6/cs not_active IP Right Cessation
- 2000-05-16 AT AT04001441T patent/ATE337008T1/de active
- 2000-05-16 PL PL383406A patent/PL199650B1/pl unknown
- 2000-05-16 DK DK00935031T patent/DK1185272T3/da active
- 2000-05-16 SI SI200030423T patent/SI1185272T1/sl unknown
- 2000-05-16 DK DK04001441T patent/DK1410800T3/da active
- 2000-05-16 ES ES06017231T patent/ES2330774T3/es not_active Expired - Lifetime
- 2000-05-16 KR KR1020017015141A patent/KR100683367B1/ko not_active IP Right Cessation
- 2000-05-16 PL PL383006A patent/PL200490B1/pl unknown
- 2000-05-16 DE DE60009697T patent/DE60009697T2/de not_active Expired - Lifetime
- 2000-05-16 TR TR2001/03361T patent/TR200103361T2/xx unknown
- 2000-05-16 PT PT00935031T patent/PT1185272E/pt unknown
- 2000-05-16 DE DE60030338T patent/DE60030338T2/de not_active Expired - Lifetime
- 2000-05-16 MX MXPA01012172A patent/MXPA01012172A/es active IP Right Grant
- 2000-05-16 PT PT06017231T patent/PT1736158E/pt unknown
- 2000-05-16 WO PCT/EP2000/004376 patent/WO2000072832A2/en active IP Right Grant
- 2000-05-16 EP EP00935031A patent/EP1185272B1/en not_active Expired - Lifetime
- 2000-05-16 US US09/979,922 patent/US6900212B1/en not_active Expired - Lifetime
- 2000-05-16 DE DE60042710T patent/DE60042710D1/de not_active Expired - Lifetime
- 2000-05-16 SI SI200030902T patent/SI1410800T1/sl unknown
- 2000-05-16 ES ES04001441T patent/ES2271707T3/es not_active Expired - Lifetime
- 2000-05-16 DK DK06017231T patent/DK1736158T3/da active
- 2000-05-16 HU HU0201275A patent/HU229059B1/hu not_active IP Right Cessation
- 2000-05-16 IL IL14670700A patent/IL146707A0/xx active IP Right Grant
- 2000-05-16 BR BR0010948-7A patent/BR0010948A/pt not_active Application Discontinuation
- 2000-05-16 AU AU50663/00A patent/AU771778B2/en not_active Ceased
- 2000-05-16 AT AT06017231T patent/ATE438399T1/de active
- 2000-05-16 CA CA2694866A patent/CA2694866A1/en not_active Abandoned
- 2000-05-16 PT PT04001441T patent/PT1410800E/pt unknown
- 2000-05-16 UA UA2001128861A patent/UA74337C2/uk unknown
- 2000-05-16 JP JP2000620944A patent/JP4884588B2/ja not_active Expired - Fee Related
- 2000-05-16 AT AT00935031T patent/ATE263564T1/de active
- 2000-05-16 CN CN200910113677A patent/CN101869565A/zh active Pending
- 2000-05-16 PL PL352373A patent/PL199516B1/pl unknown
- 2000-05-16 CA CA2615271A patent/CA2615271C/en not_active Expired - Fee Related
- 2000-05-16 CN CNA2005100544177A patent/CN1679577A/zh active Pending
- 2000-05-16 CA CA002372668A patent/CA2372668C/en not_active Expired - Fee Related
- 2000-05-16 RU RU2001133342A patent/RU2237477C2/ru not_active IP Right Cessation
- 2000-05-16 EP EP06017231A patent/EP1736158B1/en not_active Expired - Lifetime
- 2000-05-16 SK SK1646-2001A patent/SK287851B6/sk not_active IP Right Cessation
- 2000-05-16 ES ES00935031T patent/ES2219342T3/es not_active Expired - Lifetime
- 2000-05-16 EP EP04001441A patent/EP1410800B1/en not_active Expired - Lifetime
- 2000-05-16 CN CNB008081352A patent/CN1198618C/zh not_active Expired - Fee Related
- 2000-05-25 MY MYPI20002314A patent/MY135627A/en unknown
- 2000-05-26 AR ARP000102575A patent/AR024112A1/es unknown
-
2001
- 2001-11-22 IL IL146707A patent/IL146707A/en not_active IP Right Cessation
- 2001-11-26 NO NO20015746A patent/NO322120B1/no not_active IP Right Cessation
- 2001-12-20 ZA ZA200110485A patent/ZA200110485B/en unknown
-
2003
- 2003-01-23 HK HK03100617.0A patent/HK1048444B/zh not_active IP Right Cessation
-
2004
- 2004-11-23 US US10/994,226 patent/US7371756B2/en not_active Expired - Lifetime
-
2006
- 2006-04-06 NO NO20061562A patent/NO324230B1/no not_active IP Right Cessation
- 2006-11-02 CY CY20061101575T patent/CY1105750T1/el unknown
-
2007
- 2007-11-28 US US11/946,149 patent/US7642261B2/en not_active Expired - Fee Related
-
2009
- 2009-10-14 CY CY20091101063T patent/CY1109472T1/el unknown
- 2009-11-17 US US12/620,049 patent/US20100063062A1/en not_active Abandoned
-
2011
- 2011-02-10 JP JP2011027903A patent/JP2011148799A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO322120B1 (no) | Anvendelse av 1-[4-(5-cyanindol-3-yl)butyl]-4-(2-karbamoylbenzofuran-5-yl)-piperazin og dets fysiologisk akseptable salter til fremstilling av medikamenter for behandling av angstforstyrrelser av undertype | |
| Kane et al. | Efficacy and safety of aripiprazole and haloperidol versus placebo in patients with schizophrenia and schizoaffective disorder | |
| Rickels et al. | Paroxetine treatment of generalized anxiety disorder: a double-blind, placebo-controlled study | |
| Pollack et al. | Paroxetine in the treatment of generalized anxiety disorder: results of a placebo-controlled, flexible-dosage trial | |
| Giuliano et al. | Serotonin and premature ejaculation: from physiology to patient management | |
| Clayton et al. | Bupropion extended release compared with escitalopram: effects on sexual functioning and antidepressant efficacy in 2 randomized, double-blind, placebo-controlled studies | |
| Rudd et al. | The involvement of TRPV1 in emesis and anti-emesis | |
| US20120010242A1 (en) | Low dose pipamperone in treating mood disorders | |
| Kolar | Scopolamine as a potential treatment option in major depressive disorder—A literature review | |
| JP6448990B2 (ja) | 薬物依存症の治療薬としてのＴｒｋＢ受容体拮抗薬 | |
| US20120077825A1 (en) | Novel use of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine and its physiologically acceptable salts | |
| Fava | The combination of buspirone and bupropion in the treatment of depression | |
| WO2023215342A1 (en) | Compositions and methods for treating trigeminal neuralgia | |
| Patel et al. | Continuing Education Activity | |
| Montgomery | Treatment of Affective Disorders |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |