ES2402084T3 - Derivado de dibenzotiazepina y sus usos - Google Patents
Derivado de dibenzotiazepina y sus usos Download PDFInfo
- Publication number
- ES2402084T3 ES2402084T3 ES09766953T ES09766953T ES2402084T3 ES 2402084 T3 ES2402084 T3 ES 2402084T3 ES 09766953 T ES09766953 T ES 09766953T ES 09766953 T ES09766953 T ES 09766953T ES 2402084 T3 ES2402084 T3 ES 2402084T3
- Authority
- ES
- Spain
- Prior art keywords
- disorder
- pharmaceutically acceptable
- fluoro
- compound
- thiazepine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000008509 dibenzothiazepines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- CXKQSMUCGLKJEI-UHFFFAOYSA-N 8-fluoro-6-piperazin-1-ylbenzo[b][1,4]benzothiazepine Chemical compound C12=CC(F)=CC=C2SC2=CC=CC=C2N=C1N1CCNCC1 CXKQSMUCGLKJEI-UHFFFAOYSA-N 0.000 claims abstract description 23
- 208000020925 Bipolar disease Diseases 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 201000000980 schizophrenia Diseases 0.000 claims description 14
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 208000020016 psychiatric disease Diseases 0.000 claims description 9
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 230000036651 mood Effects 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 description 28
- 238000011282 treatment Methods 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 18
- 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 description 17
- 108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 230000008485 antagonism Effects 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
- 208000035475 disorder Diseases 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 11
- 206010026749 Mania Diseases 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- -1 aminophenyl compound Chemical class 0.000 description 10
- VKHYKHAWFZNIKB-UHFFFAOYSA-N benzo[b][1,4]benzothiazepine Chemical compound C1=NC2=CC=CC=C2SC2=CC=CC=C21 VKHYKHAWFZNIKB-UHFFFAOYSA-N 0.000 description 10
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229960005017 olanzapine Drugs 0.000 description 8
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- BHJJFXMGSTZHIG-UHFFFAOYSA-N 8-fluoro-5h-benzo[b][1,4]benzothiazepin-6-one Chemical compound N1C(=O)C2=CC(F)=CC=C2SC2=CC=CC=C21 BHJJFXMGSTZHIG-UHFFFAOYSA-N 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- 208000024891 symptom Diseases 0.000 description 7
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 7
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 208000019022 Mood disease Diseases 0.000 description 6
- 230000003001 depressive effect Effects 0.000 description 6
- 229960000632 dexamfetamine Drugs 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- ZTHJULTYCAQOIJ-WXXKFALUSA-N quetiapine fumarate Chemical compound [H+].[H+].[O-]C(=O)\C=C\C([O-])=O.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 ZTHJULTYCAQOIJ-WXXKFALUSA-N 0.000 description 6
- 229940035004 seroquel Drugs 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 208000020114 Schizophrenia and other psychotic disease Diseases 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 229960003638 dopamine Drugs 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000007920 subcutaneous administration Methods 0.000 description 5
- QPPOMEOQNLTFRU-UHFFFAOYSA-N 1,4-thiazepine Chemical class S1C=CC=NC=C1 QPPOMEOQNLTFRU-UHFFFAOYSA-N 0.000 description 4
- RFXCQLRFGHQGCI-UHFFFAOYSA-N 6-chloro-8-fluorobenzo[b][1,4]benzothiazepine Chemical compound N1=C(Cl)C2=CC(F)=CC=C2SC2=CC=CC=C21 RFXCQLRFGHQGCI-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 101150049660 DRD2 gene Proteins 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 102000003834 Histamine H1 Receptors Human genes 0.000 description 4
- 108090000110 Histamine H1 Receptors Proteins 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 208000028683 bipolar I disease Diseases 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000010534 mechanism of action Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229960004431 quetiapine Drugs 0.000 description 4
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 3
- DPBHQCZPYGSTIP-UHFFFAOYSA-N 2-(2-aminophenyl)sulfanyl-5-fluorobenzoic acid Chemical compound NC1=CC=CC=C1SC1=CC=C(F)C=C1C(O)=O DPBHQCZPYGSTIP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910019213 POCl3 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 206010041349 Somnolence Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 230000000561 anti-psychotic effect Effects 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 239000003693 atypical antipsychotic agent Substances 0.000 description 3
- 229940127236 atypical antipsychotics Drugs 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OQBMJMJZMDBQSM-UHFFFAOYSA-N 2-bromo-5-fluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1Br OQBMJMJZMDBQSM-UHFFFAOYSA-N 0.000 description 2
- 108060003345 Adrenergic Receptor Proteins 0.000 description 2
- 102000017910 Adrenergic receptor Human genes 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- 208000017667 Chronic Disease Diseases 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 2
- 208000011688 Generalised anxiety disease Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 206010027944 Mood disorder due to a general medical condition Diseases 0.000 description 2
- 208000001089 Multiple system atrophy Diseases 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 206010031127 Orthostatic hypotension Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010039897 Sedation Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 208000025307 bipolar depression Diseases 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 208000026725 cyclothymic disease Diseases 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- XHUNKCWICZXHKQ-UHFFFAOYSA-N ethyl 5-fluoro-2-(2-nitrophenyl)sulfanylbenzoate Chemical compound CCOC(=O)C1=CC(F)=CC=C1SC1=CC=CC=C1[N+]([O-])=O XHUNKCWICZXHKQ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 208000029364 generalized anxiety disease Diseases 0.000 description 2
- 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 2
- 230000002296 hyperlocomotor Effects 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 208000024714 major depressive disease Diseases 0.000 description 2
- 238000013289 male long evans rat Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000003176 neuroleptic agent Substances 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000012154 norepinephrine uptake Effects 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000000306 recurrent effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000036280 sedation Effects 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 1
- HFANPBYTXDKUDJ-UHFFFAOYSA-N 4-fluoro-1-nitro-2-phenylsulfanylbenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1SC1=CC=CC=C1 HFANPBYTXDKUDJ-UHFFFAOYSA-N 0.000 description 1
- SWLWFGHLXXGBNA-UHFFFAOYSA-N 4-fluoro-2-phenylsulfanylaniline Chemical compound NC1=CC=C(F)C=C1SC1=CC=CC=C1 SWLWFGHLXXGBNA-UHFFFAOYSA-N 0.000 description 1
- KBPXNMVPZMSZDE-UHFFFAOYSA-N 5-fluoro-2-(2-nitrophenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1SC1=CC=CC=C1[N+]([O-])=O KBPXNMVPZMSZDE-UHFFFAOYSA-N 0.000 description 1
- WSOZOINWBSJTER-UHFFFAOYSA-N 5-fluoro-2-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1S WSOZOINWBSJTER-UHFFFAOYSA-N 0.000 description 1
- 208000030090 Acute Disease Diseases 0.000 description 1
- 208000017194 Affective disease Diseases 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- 208000008811 Agoraphobia Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 208000021465 Brief psychotic disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000024254 Delusional disease Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 239000012739 FreeStyle 293 Expression medium Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000639975 Homo sapiens Sodium-dependent noradrenaline transporter Proteins 0.000 description 1
- 206010020400 Hostility Diseases 0.000 description 1
- GRRNUXAQVGOGFE-UHFFFAOYSA-N Hygromycin-B Natural products OC1C(NC)CC(N)C(O)C1OC1C2OC3(C(C(O)C(O)C(C(N)CO)O3)O)OC2C(O)C(CO)O1 GRRNUXAQVGOGFE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010061296 Motor dysfunction Diseases 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010052794 Panic disorder with agoraphobia Diseases 0.000 description 1
- 206010033668 Panic disorder without agoraphobia Diseases 0.000 description 1
- 206010034912 Phobia Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000023146 Pre-existing disease Diseases 0.000 description 1
- 206010061921 Psychotic disorder due to a general medical condition Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000020186 Schizophreniform disease Diseases 0.000 description 1
- 208000019568 Shared Paranoid disease Diseases 0.000 description 1
- 208000028810 Shared psychotic disease Diseases 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 208000026345 acute stress disease Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 208000022257 bipolar II disease Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical class C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000008533 dibenzodiazepines Chemical group 0.000 description 1
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 108010017146 dopamine D2L receptor Proteins 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- OBCJCDDVWWAXJW-UHFFFAOYSA-N ethyl 2-(2-aminophenyl)sulfanyl-5-fluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=CC=C1SC1=CC=CC=C1N OBCJCDDVWWAXJW-UHFFFAOYSA-N 0.000 description 1
- PQRHDMMRVLIDMT-UHFFFAOYSA-N ethyl 5-fluoro-2-sulfanylbenzoate Chemical compound CCOC(=O)C1=CC(F)=CC=C1S PQRHDMMRVLIDMT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000011990 functional testing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 102000055827 human SLC6A2 Human genes 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- GRRNUXAQVGOGFE-NZSRVPFOSA-N hygromycin B Chemical compound O[C@@H]1[C@@H](NC)C[C@@H](N)[C@H](O)[C@H]1O[C@H]1[C@H]2O[C@@]3([C@@H]([C@@H](O)[C@@H](O)[C@@H](C(N)CO)O3)O)O[C@H]2[C@@H](O)[C@@H](CO)O1 GRRNUXAQVGOGFE-NZSRVPFOSA-N 0.000 description 1
- 229940097277 hygromycin b Drugs 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000000185 intracerebroventricular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UDBLTZWJCWPYBA-UHFFFAOYSA-N methyl 2,5-difluorobenzoate Chemical compound COC(=O)C1=CC(F)=CC=C1F UDBLTZWJCWPYBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 150000000221 oxazepines Chemical group 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 208000002851 paranoid schizophrenia Diseases 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000013105 post hoc analysis Methods 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 229950001518 raclopride Drugs 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 description 1
- 229960003770 reboxetine Drugs 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229960001534 risperidone Drugs 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 208000022610 schizoaffective disease Diseases 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 201000001716 specific phobia Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000004912 thiazepines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- 239000011345 viscous material Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- XOFLBQFBSOEHOG-UUOKFMHZSA-N γS-GTP Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O XOFLBQFBSOEHOG-UUOKFMHZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D281/16—[b, f]-condensed
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7441708P | 2008-06-20 | 2008-06-20 | |
| US74417P | 2008-06-20 | ||
| PCT/SE2009/050763 WO2009154563A1 (en) | 2008-06-20 | 2009-06-18 | Dibenzothiazepine derivatives and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2402084T3 true ES2402084T3 (es) | 2013-04-26 |
Family
ID=41431860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09766953T Active ES2402084T3 (es) | 2008-06-20 | 2009-06-18 | Derivado de dibenzotiazepina y sus usos |
Country Status (37)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI488854B (zh) * | 2008-06-20 | 2015-06-21 | Astrazeneca Ab | 二苯并噻氮呯衍生物及其用途 |
| CN105981027A (zh) * | 2013-08-12 | 2016-09-28 | 哥莱菲特软件公司 | 安全认证并切换至加密域 |
| CN103524455A (zh) * | 2013-10-30 | 2014-01-22 | 苏州敬业医药化工有限公司 | 一种制备2-氯-二苯并[b,f][1,4]硫氮杂卓-11-[10H]酮的方法 |
| CN106134230A (zh) | 2013-11-21 | 2016-11-16 | 哥莱菲特软件公司 | 用于移动信息设备上的远程内容和配置控制的管理域 |
| CN104447615A (zh) * | 2014-02-28 | 2015-03-25 | 广东东阳光药业有限公司 | 喹硫平中间体的制备方法 |
| CN120981447A (zh) * | 2023-03-08 | 2025-11-18 | 法兰克福大学 | Slack激活化合物及其医学用途 |
| EP4428132A1 (en) * | 2023-03-08 | 2024-09-11 | Johann-Wolfgang-Goethe-Universität Frankfurt am Main | Slack-activating compounds and their medical use |
Family Cites Families (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL293201A (enExample) | ||||
| NL294355A (enExample) | ||||
| DE1620703B2 (de) * | 1960-08-16 | 1976-11-25 | Ausscheidung aus: 12 80 879 Dr. A. Wander AG, Bern | 11-basisch substituierte dibenzo eckige klammer auf b,f eckige klammer zu-eckige klammer auf 1,4 eckige klammer zu-thiazepine |
| CH422793A (de) | 1961-07-20 | 1966-10-31 | Wander Ag Dr A | Verfahren zur Herstellung 11-basisch substituierter Dibenzo(b,f) (1,4)thiazepine |
| DE1620713A1 (de) * | 1962-05-25 | 1970-07-02 | Wander Ag Dr A | Verfahren zur Herstellung von 11-basisch substituierter Dibenzo[b,f][1,4]thiazepine |
| CH476753A (de) | 1962-06-08 | 1969-08-15 | Wander Ag Dr A | Verfahren zur Herstellung von 11-basisch substituierter Dibenzo(b,f)(1,4)thiazepine |
| NL140242B (nl) | 1963-03-01 | 1973-11-15 | Wander Ag Dr A | Werkwijze voor het bereiden van op de 11-plaats door een basische groep gesubstitueerde dibenz (b.f.)(1.4) oxazepinen. |
| NL293210A (enExample) | 1963-05-09 | |||
| US3908010A (en) | 1967-03-22 | 1975-09-23 | Wander Ag Dr A | Basically substituted heterocycles as anti-emetics |
| US3683034A (en) | 1963-09-27 | 1972-08-08 | Upjohn Co | Process for the preparation of substituted hydroquinones |
| US3884920A (en) | 1967-07-14 | 1975-05-20 | Sandoz Ag | 11-Basically substituted dibenz {8 b,f{9 {0 {8 1,4{9 {0 oxazepines |
| US3412193A (en) | 1965-12-13 | 1968-11-19 | American Cyanamid Co | 11-(4-methyl-1-piperazinyl)dibenz[b, f][1, 4]oxazepines or thiazepines for controlling fertility |
| US3444169A (en) | 1966-01-17 | 1969-05-13 | American Cyanamid Co | Process for 11 - aminodibenz(b,f)(1,4)oxazepines and analogous thiazepines |
| NL6715650A (enExample) | 1966-12-16 | 1968-06-17 | ||
| US3852446A (en) | 1967-03-13 | 1974-12-03 | Sandoz Ag | Organic compounds in treatment of psychotic disturbances |
| US3758479A (en) | 1967-03-22 | 1973-09-11 | Sandoz Ag | Nitro and sulphamoyl substituted dibenzodiazepines |
| US3539573A (en) * | 1967-03-22 | 1970-11-10 | Jean Schmutz | 11-basic substituted dibenzodiazepines and dibenzothiazepines |
| CH569731A5 (enExample) * | 1972-04-04 | 1975-11-28 | Wander Ag Dr A | |
| US3962248A (en) * | 1972-04-04 | 1976-06-08 | Sandoz, Inc. | Process for making 11-piperazino-diazepines, oxazepines, thiazepines and azepines |
| GB8607684D0 (en) | 1986-03-27 | 1986-04-30 | Ici America Inc | Thiazepine compounds |
| GB8705574D0 (en) | 1987-03-10 | 1987-04-15 | Ici Plc | Preparation of thiazepine compound |
| JPH04211071A (ja) * | 1990-03-05 | 1992-08-03 | Hokuriku Seiyaku Co Ltd | 多環式化合物 |
| JPH0565257A (ja) | 1991-07-05 | 1993-03-19 | Hokuriku Seiyaku Co Ltd | 多環式化合物及びその用途 |
| US5661184A (en) | 1994-08-12 | 1997-08-26 | Eli Lilly And Company | Psychiatric agents |
| CZ289512B6 (cs) | 1994-08-24 | 2002-02-13 | Astra Aktiebolag | Spiro-azabicyklické sloučeniny pouľitelné při terapii |
| US5602121A (en) * | 1994-12-12 | 1997-02-11 | Allelix Biopharmaceuticals, Inc. | Alkyl-substituted compounds having dopamine receptor affinity |
| SE9504661D0 (sv) | 1995-12-22 | 1995-12-22 | Astra Pharma Inc | New compounds |
| SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
| AR013184A1 (es) | 1997-07-18 | 2000-12-13 | Astrazeneca Ab | Aminas heterociclicas espiroazobiciclicas, composicion farmaceutica, uso de dichas aminas para preparar medicamentos y metodo de tratamiento o profilaxis |
| SE9702799D0 (sv) | 1997-07-25 | 1997-07-25 | Astra Ab | New compounds |
| US6342488B1 (en) | 1998-08-18 | 2002-01-29 | Sepracor, Inc. | Phosphonorisperidone and sulforisperidone compositions and methods |
| SE9900100D0 (sv) | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| WO2001008680A1 (de) | 1999-07-28 | 2001-02-08 | Oswald Wiss | Präparate mit sauerstoffsparender wirkung bei körperlicher leistung |
| SE9903760D0 (sv) | 1999-10-18 | 1999-10-18 | Astra Ab | New compounds |
| SE0002729D0 (sv) | 2000-07-20 | 2000-07-20 | Astrazeneca Ab | Novel compound form |
| AU2002249885A1 (en) | 2000-11-17 | 2002-08-12 | Adolor Corporation | Delta agonist analgesics |
| IL139975A0 (en) | 2000-11-29 | 2002-02-10 | Univ Ramot | Anti proliferative drugs |
| ES2319876T3 (es) | 2001-05-18 | 2009-05-14 | Astrazeneca Ab | Derivados de 4 (fenil-piperazinil-metil) benzamida y su uso para el tratamiento de la ansiedad o trastornos gastrointestinales. |
| SI1397366T1 (sl) | 2001-06-01 | 2007-06-30 | Astrazeneca Ab | Nov ligand za nikotinske acetilholinske receptorje, koristen v terapiji |
| ES2330837T3 (es) | 2001-07-09 | 2009-12-16 | Combinatorx, Incorporated | Combinaciones para el tratamiento de trastornos inflamatorios. |
| US7544681B2 (en) | 2001-09-27 | 2009-06-09 | Ramot At Tel Aviv University Ltd. | Conjugated psychotropic drugs and uses thereof |
| KR100996239B1 (ko) | 2001-09-27 | 2010-11-23 | 바-일란 유니버시티 | 접합된 항-정신병 약물 및 그의 용도 |
| US7417049B2 (en) | 2002-04-18 | 2008-08-26 | Astrazeneca Ab | Furyl compounds |
| EP1499616B1 (en) | 2002-04-18 | 2009-06-17 | AstraZeneca AB | Heterocyclic compounds |
| DE60333746D1 (de) | 2002-04-18 | 2010-09-23 | Astrazeneca Ab | Thienylverbindungen |
| SE0202430D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New Compounds |
| SE0202465D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| SE0202598D0 (sv) | 2002-09-02 | 2002-09-02 | Astrazeneca Ab | Alpha-7 Nicotinic receptor agonists and statins in combination |
| CN1681388A (zh) | 2002-09-18 | 2005-10-12 | Fmc有限公司 | 三环衍生物杀虫剂 |
| EP1578198A1 (en) | 2002-12-20 | 2005-09-28 | Basf Aktiengesellschaft | Pesticidal dibenzo(hetero)azepine derivatives |
| MXPA05007784A (es) | 2003-01-23 | 2005-09-30 | Acadia Pharm Inc | Empleo de la n-desmetilclozapina para tratar las enfermedades neuropsiquiatricas humanas. |
| EP1495008A1 (en) | 2003-02-22 | 2005-01-12 | Teva Pharmaceutical Industries Limited | Synthesis of quetiapine and pharmaceutically acceptable salts thereof |
| DE10310196A1 (de) | 2003-03-06 | 2004-09-23 | Rina-Netzwerk Rna Technologien Gmbh | Verwendung eines trizyklischen Antidepressivums zur Förderung der Endozytose |
| JP2006523707A (ja) | 2003-04-15 | 2006-10-19 | アストラゼネカ アクツィエボラーグ | 治療化合物 |
| US20060217366A1 (en) * | 2003-07-02 | 2006-09-28 | Astrazeneca Ab | Method of treating schizophrenia and other disorders |
| PL195728B1 (pl) | 2003-07-18 | 2007-10-31 | Helm Ag | Sposób wytwarzania 11-(1-piperazynylo)dibenzo[b,f][1,4]tiazepiny |
| RU2394030C2 (ru) * | 2003-12-22 | 2010-07-10 | Акадиа Фармасьютикалз Инк. | АМИНОЗАМЕЩЕННЫЕ АНАЛОГИ ДИАРИЛ [a,d] ЦИКЛОГЕПТЕНА В КАЧЕСТВЕ МУСКАРИНОВЫХ АГОНИСТОВ И СПОСОБЫ ЛЕЧЕНИЯ ПСИХОНЕВРОЛОГИЧЕСКИХ РАССТРОЙСТВ |
| PT1696931E (pt) | 2003-12-22 | 2009-06-12 | Acadia Pharm Inc | Análogos diaril[a,d]ciclo-hepteno substituídos com amino utilizados como agonistas muscarínicos e métodos de tratamento de perturbações neuropsiquiátricas |
| US20060063754A1 (en) * | 2004-09-21 | 2006-03-23 | Edgar Dale M | Methods of treating a sleep disorder |
| WO2006071730A1 (en) | 2004-12-27 | 2006-07-06 | Astrazeneca Ab | Pyrazolone compounds as metabotropic glutamate receptor agonists for the treatment of neurological and psychiatric disorders |
| WO2006073360A1 (en) * | 2005-01-07 | 2006-07-13 | Astrazeneca Ab | NEW USE OF 11-PIPERAZIN-1-YLDIBENZO [b,f] [1,4] THIAZEPINE OR ITS PHARMACEUTICALLY ACCEPTABLE SALT AND TO ORAL PHARMACEUTICAL COMPOSITIONS |
| EP1865962A2 (en) * | 2005-04-04 | 2007-12-19 | Arcadia Pharmaceuticals Inc. | Use of n-desmethylclozapine and related compounds as dopamine stabilizing agents |
| WO2007053618A1 (en) * | 2005-10-31 | 2007-05-10 | Acadia Pharmaceuticals Inc. | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| WO2008079847A1 (en) | 2006-12-20 | 2008-07-03 | Astrazeneca Ab (Se/Se) | Compounds and uses thereof |
| WO2008100715A1 (en) | 2007-02-09 | 2008-08-21 | Astrazeneca Ab | Aza-isoindolones and their use as metabotropic glutamate receptor potentiators - 613 |
| US7491871B2 (en) | 2007-04-25 | 2009-02-17 | Stine Seed Farm, Inc. | Soybean cultivar S060299 |
| TWI417100B (zh) | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-842之用途 |
| TW200911255A (en) | 2007-06-07 | 2009-03-16 | Astrazeneca Ab | Metabotropic glutamate receptor oxadiazole ligands and their use as potentiators-841 |
| TWI488854B (zh) * | 2008-06-20 | 2015-06-21 | Astrazeneca Ab | 二苯并噻氮呯衍生物及其用途 |
-
2009
- 2009-06-18 TW TW098120494A patent/TWI488854B/zh not_active IP Right Cessation
- 2009-06-18 ME MEP-2013-27A patent/ME01516B/me unknown
- 2009-06-18 PT PT97669535T patent/PT2307389E/pt unknown
- 2009-06-18 KR KR1020117001427A patent/KR20110019781A/ko not_active Ceased
- 2009-06-18 AU AU2009260905A patent/AU2009260905B2/en not_active Ceased
- 2009-06-18 UY UY0001031919A patent/UY31919A/es not_active Application Discontinuation
- 2009-06-18 PL PL09766953T patent/PL2307389T3/pl unknown
- 2009-06-18 CA CA2728675A patent/CA2728675A1/en not_active Abandoned
- 2009-06-18 CN CN200980132601.5A patent/CN102131791B/zh not_active Expired - Fee Related
- 2009-06-18 SI SI200930544T patent/SI2307389T1/sl unknown
- 2009-06-18 JP JP2011514540A patent/JP5468068B2/ja not_active Expired - Fee Related
- 2009-06-18 WO PCT/SE2009/050763 patent/WO2009154563A1/en not_active Ceased
- 2009-06-18 EA EA201001889A patent/EA201001889A1/ru unknown
- 2009-06-18 RS RS20130109A patent/RS52703B/sr unknown
- 2009-06-18 NZ NZ590616A patent/NZ590616A/xx not_active IP Right Cessation
- 2009-06-18 BR BRPI0914231A patent/BRPI0914231A2/pt not_active IP Right Cessation
- 2009-06-18 HR HRP20130234AT patent/HRP20130234T1/hr unknown
- 2009-06-18 US US12/999,808 patent/US20110160184A1/en not_active Abandoned
- 2009-06-18 ES ES09766953T patent/ES2402084T3/es active Active
- 2009-06-18 MY MYPI2010006035A patent/MY157518A/en unknown
- 2009-06-18 EP EP09766953A patent/EP2307389B1/en active Active
- 2009-06-18 DK DK09766953.5T patent/DK2307389T3/da active
- 2009-06-18 PE PE2010001170A patent/PE20110029A1/es not_active Application Discontinuation
- 2009-06-18 MX MX2010014203A patent/MX2010014203A/es active IP Right Grant
- 2009-06-18 UA UAA201015001A patent/UA105903C2/uk unknown
- 2009-06-19 AR ARP090102240A patent/AR072200A1/es unknown
- 2009-06-19 US US12/487,725 patent/US8158618B2/en not_active Expired - Fee Related
-
2010
- 2010-12-16 IL IL210081A patent/IL210081A/en not_active IP Right Cessation
- 2010-12-17 CL CL2010001471A patent/CL2010001471A1/es unknown
- 2010-12-20 HN HN2010002683A patent/HN2010002683A/es unknown
- 2010-12-20 SV SV2010003769A patent/SV2010003769A/es not_active Application Discontinuation
- 2010-12-20 CU CU20100252A patent/CU23884B1/es not_active IP Right Cessation
- 2010-12-20 EC EC2010010698A patent/ECSP10010698A/es unknown
- 2010-12-20 NI NI201000224A patent/NI201000224A/es unknown
- 2010-12-20 DO DO2010000393A patent/DOP2010000393A/es unknown
- 2010-12-20 CR CR11860A patent/CR11860A/es unknown
-
2011
- 2011-01-19 ZA ZA2011/00488A patent/ZA201100488B/en unknown
-
2012
- 2012-04-12 US US13/445,347 patent/US8653257B2/en not_active Expired - Fee Related
-
2013
- 2013-03-22 CY CY20131100246T patent/CY1113845T1/el unknown
- 2013-11-21 IL IL229560A patent/IL229560A/en not_active IP Right Cessation
-
2014
- 2014-01-27 JP JP2014011979A patent/JP2014098006A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2402084T3 (es) | Derivado de dibenzotiazepina y sus usos | |
| ES2565229T3 (es) | Derivados 2-amino-4-(piridin-2-il)-5,6-dihidro-4H-1,3-oxazina y su uso como inhibidores de BACE-1 y/o BACE-2 | |
| ES2761423T3 (es) | Compuestos para tratar la atrofia muscular espinal | |
| ES2441017T3 (es) | Compuesto de pirazolo[1,5-A]pirimidina como antagonista del receptor CB1 | |
| ES2368691T3 (es) | Derivados de benzotiazepina y su utilización como moduladores de los receptores ampa y nmda. | |
| ES2638912T3 (es) | Compuestos orgánicos | |
| ES2341127T3 (es) | Compuestos de bencisoxazol-piperazina y procedimiento de uso. | |
| PT2250172E (pt) | Inibidores de pirrolpirazina-cinase | |
| JP4897683B2 (ja) | チエノピリジノン化合物及び治療方法 | |
| JP2008514643A (ja) | 新規ピペリジニルアミノ−チエノ[2,3−d]ピリミジン化合物 | |
| JP7174963B2 (ja) | 疾患の処置のための複素環化合物 | |
| AU2025267332A1 (en) | Psychotropic agents and uses thereof | |
| ES2316619T3 (es) | Derivados de arilsulfonilo con afinidad receptora de 5-ht 6. | |
| ES2378452T3 (es) | �?cido 3-[4-(dibenzo[b,f][1,4]oxazepin-11-il)-piperazin-1-il]-2,2¿dimetil-propanoico para usarlo en el tratamiento de trastornos del sueño | |
| ES2309398T3 (es) | Derivados 3,4-dihidro-tieno (2,3-d)pirimidin-4-ona-3-sustituidos, produccion y sus usos. | |
| ES2768602T3 (es) | Derivados de fenil-urea y de fenil-carbamato como inhibidores de la agregación de proteínas | |
| ES2371053T3 (es) | Compuestos de benzazepina que tienen afinidad por el receptor d3 de dopamina y usos de los mismos. | |
| ES2239592T3 (es) | Derivados de carbamoil tetrahidropirina. | |
| ES2333918T3 (es) | Derivados de pirrolidina que tiene la actividad en el transportador glyt1. | |
| ES2321217T3 (es) | Inhibidores del transporte de glicina. | |
| ES2307750T3 (es) | Antagonistas del factor de liberacion de corticotropina. | |
| CA3138284A1 (en) | Nanoparticle formulation of bcl-2 inhibitor | |
| ES2256506T3 (es) | Agonistas triciclicos del receptor crf. | |
| HK1156308B (en) | Dibenzothiazepine derivative and use thereof | |
| JP2007533715A (ja) | GlyT1阻害剤として用いるためのモルホリニルおよびピペリジニル基を有する化合物 |