KR100886578B1 - 카바메이트 화합물을 포함하는 정신증 장애 예방용 또는 치료용 약제학적 조성물 - Google Patents
카바메이트 화합물을 포함하는 정신증 장애 예방용 또는 치료용 약제학적 조성물 Download PDFInfo
- Publication number
- KR100886578B1 KR100886578B1 KR1020037011292A KR20037011292A KR100886578B1 KR 100886578 B1 KR100886578 B1 KR 100886578B1 KR 1020037011292 A KR1020037011292 A KR 1020037011292A KR 20037011292 A KR20037011292 A KR 20037011292A KR 100886578 B1 KR100886578 B1 KR 100886578B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- group
- schizophrenia
- delete delete
- enantiomer
- 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.)
- Expired - Lifetime
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 16
- 208000028017 Psychotic disease Diseases 0.000 title abstract description 41
- -1 carbamate compound Chemical class 0.000 title abstract description 7
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 abstract description 31
- 238000000034 method Methods 0.000 abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 14
- 239000001257 hydrogen Substances 0.000 abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 abstract description 8
- 239000000460 chlorine Substances 0.000 abstract description 8
- 229910052736 halogen Inorganic materials 0.000 abstract description 8
- 150000002367 halogens Chemical class 0.000 abstract description 8
- 125000001424 substituent group Chemical group 0.000 abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052794 bromium Inorganic materials 0.000 abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 abstract description 5
- 239000011737 fluorine Substances 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract description 5
- BQYRVMAWJCIIKI-UHFFFAOYSA-N carbamic acid;1-phenylethane-1,2-diol Chemical class NC(O)=O.OCC(O)C1=CC=CC=C1 BQYRVMAWJCIIKI-UHFFFAOYSA-N 0.000 abstract description 4
- QTWMTAXHUBXJQF-UHFFFAOYSA-N (2-carbamoyloxy-2-phenylethyl) carbamate Chemical class NC(=O)OCC(OC(N)=O)C1=CC=CC=C1 QTWMTAXHUBXJQF-UHFFFAOYSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 13
- 230000006977 prepulse inhibition Effects 0.000 description 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000003937 drug carrier Substances 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- 230000003542 behavioural effect Effects 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 208000020016 psychiatric disease Diseases 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000561 anti-psychotic effect Effects 0.000 description 4
- 239000000164 antipsychotic agent Substances 0.000 description 4
- 229940005529 antipsychotics Drugs 0.000 description 4
- 229960004170 clozapine Drugs 0.000 description 4
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 238000007917 intracranial administration Methods 0.000 description 4
- 239000007909 solid dosage form Substances 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 206010012239 Delusion Diseases 0.000 description 3
- 208000007101 Muscle Cramp Diseases 0.000 description 3
- 241000283984 Rodentia Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000006735 deficit Effects 0.000 description 3
- 231100000868 delusion Toxicity 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000008297 liquid dosage form Substances 0.000 description 3
- 229960005017 olanzapine Drugs 0.000 description 3
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 3
- 208000002851 paranoid schizophrenia Diseases 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000036278 prepulse Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 2
- 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 208000004547 Hallucinations Diseases 0.000 description 2
- 206010021118 Hypotonia Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 208000036755 Schizophrenia simple Diseases 0.000 description 2
- 208000036752 Schizophrenia, paranoid type Diseases 0.000 description 2
- 208000036750 Schizophrenia, residual type Diseases 0.000 description 2
- 206010039897 Sedation Diseases 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000007894 caplet Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 208000015114 central nervous system disease Diseases 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 230000000857 drug effect Effects 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000007897 gelcap Substances 0.000 description 2
- 239000008187 granular material Substances 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
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000007914 intraventricular administration Methods 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000036640 muscle relaxation Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 229960001534 risperidone Drugs 0.000 description 2
- 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 2
- 230000000862 serotonergic effect Effects 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 0 **(*)C(OCC(c1ccccc1)O)=O Chemical compound **(*)C(OCC(c1ccccc1)O)=O 0.000 description 1
- QVFDMWGKHUFODK-UHFFFAOYSA-N 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine;hydrochloride Chemical compound Cl.COC1=CC(CC(C)N)=C(OC)C=C1I QVFDMWGKHUFODK-UHFFFAOYSA-N 0.000 description 1
- BGMZUEKZENQUJY-UHFFFAOYSA-N 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine Chemical compound COC1=CC(CC(C)N)=C(OC)C=C1I BGMZUEKZENQUJY-UHFFFAOYSA-N 0.000 description 1
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 1
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 208000024254 Delusional disease Diseases 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010021402 Illogical thinking Diseases 0.000 description 1
- 201000006347 Intellectual Disability Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 208000032023 Signs and Symptoms Diseases 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 229940127236 atypical antipsychotics Drugs 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000004641 brain development Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 101150047356 dec-1 gene Proteins 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000008451 emotion Effects 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 230000006397 emotional response Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000012054 flavored emulsion Substances 0.000 description 1
- 235000020375 flavoured syrup Nutrition 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000000380 hallucinogen Substances 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000002357 osmotic agent Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000002974 pharmacogenomic effect Effects 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 229950010883 phencyclidine Drugs 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000002360 prefrontal effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-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
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
-
- 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
- A61P25/24—Antidepressants
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27188901P | 2001-02-27 | 2001-02-27 | |
| US60/271,889 | 2001-02-27 | ||
| US10/081,761 | 2002-02-21 | ||
| US10/081,761 US6541513B2 (en) | 2001-02-27 | 2002-02-21 | Carbamate compounds for use in preventing or treating psychotic disorders |
| PCT/US2002/006119 WO2002067927A1 (en) | 2001-02-27 | 2002-02-21 | Carbamate compounds for use in preventing or treating psychotic disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20030076713A KR20030076713A (ko) | 2003-09-26 |
| KR100886578B1 true KR100886578B1 (ko) | 2009-03-05 |
Family
ID=26765939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020037011292A Expired - Lifetime KR100886578B1 (ko) | 2001-02-27 | 2002-02-21 | 카바메이트 화합물을 포함하는 정신증 장애 예방용 또는 치료용 약제학적 조성물 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6541513B2 (enExample) |
| EP (1) | EP1401424B1 (enExample) |
| JP (1) | JP4276841B2 (enExample) |
| KR (1) | KR100886578B1 (enExample) |
| CN (1) | CN1262271C (enExample) |
| AR (1) | AR032876A1 (enExample) |
| AT (1) | ATE346597T1 (enExample) |
| AU (1) | AU2002242296B2 (enExample) |
| BR (1) | BR0207829A (enExample) |
| CA (1) | CA2439480C (enExample) |
| CZ (1) | CZ302412B6 (enExample) |
| DE (1) | DE60216457T2 (enExample) |
| DK (1) | DK1401424T3 (enExample) |
| ES (1) | ES2275844T3 (enExample) |
| HU (1) | HUP0303342A3 (enExample) |
| IL (2) | IL157588A0 (enExample) |
| MX (1) | MXPA03007722A (enExample) |
| NO (1) | NO20033801L (enExample) |
| NZ (1) | NZ527991A (enExample) |
| PL (1) | PL365021A1 (enExample) |
| PT (1) | PT1401424E (enExample) |
| RS (1) | RS51056B (enExample) |
| RU (1) | RU2302240C2 (enExample) |
| TW (1) | TWI251486B (enExample) |
| WO (1) | WO2002067927A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014142549A1 (en) * | 2013-03-12 | 2014-09-18 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compound and a composition for preventing or treating a memory loss-related disease comprising the same |
| US9682059B2 (en) | 2013-03-12 | 2017-06-20 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compounds for use in preventing or treating epilepsy or epilepsy-related syndrome |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002007822A2 (en) * | 2000-07-21 | 2002-01-31 | Ortho-Mcneil Pharmaceutical, Inc. | Carbamate compounds for use in preventing or treating neuropathic pain and cluster and migraine headache-associated pain |
| CA2439295C (en) * | 2001-02-27 | 2010-05-25 | Ortho-Mcneil Pharmaceutical, Inc. | Carbamate compounds for use in preventing or treating neurodegenerative disorders |
| BR0207830A (pt) * | 2001-02-27 | 2004-06-22 | Ortho Mcneil Pharm Inc | Compostos de carbamato para uso em prevenir ou tratar distúrbios de ansiedade |
| RU2303445C2 (ru) | 2001-07-16 | 2007-07-27 | Орто-Макнейл Фармасьютикал, Инк. | Карбаматные соединения для применения для предотвращения или лечения невропатической боли и боли, связанной с кластерной и мигреневой головной болью |
| WO2005107719A2 (en) * | 2004-05-06 | 2005-11-17 | Sandoz Ag | Pharmaceutical composition comprising hydrophobic drug having improved solubility |
| CN101272776B (zh) * | 2005-07-26 | 2012-10-03 | 詹森药业有限公司 | 氨基甲酸酯在制备治疗物质滥用相关疾病药物中的用途 |
| EA200970436A1 (ru) * | 2006-10-30 | 2009-12-30 | Янссен Фармацевтика, Н.В. | Соединения карбамата для лечения депрессии |
| EP2089011A1 (en) * | 2006-10-31 | 2009-08-19 | Janssen Pharmaceutica N.V. | Treatment of pervasive developmental disorders |
| US8609849B1 (en) | 2010-11-30 | 2013-12-17 | Fox Chase Chemical Diversity Center, Inc. | Hydroxylated sulfamides exhibiting neuroprotective action and their method of use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6103759A (en) * | 1996-01-16 | 2000-08-15 | Sk Corporation | Halogen substituted carbamate compounds from 2-phenyl-1, 2-ethanediol |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US278380A (en) * | 1883-05-29 | Thermometer | ||
| US3313692A (en) * | 1958-04-21 | 1967-04-11 | Armour Pharma | Method of inducing calming and muscle relaxation with carbamates |
| US3265728A (en) * | 1962-07-18 | 1966-08-09 | Armour Pharma | Substituted phenethyl carbamates |
| KR0167346B1 (ko) * | 1989-06-09 | 1999-01-15 | 로버트 에이. 아미테이지 | 중추신경계 활성을 갖는 헤테로사이클릭 아민 |
| US5492930A (en) * | 1994-04-25 | 1996-02-20 | Schering Corporation | Method and formulation for treating CNS disorders |
-
2002
- 2002-02-21 US US10/081,761 patent/US6541513B2/en not_active Expired - Lifetime
- 2002-02-21 JP JP2002567294A patent/JP4276841B2/ja not_active Expired - Lifetime
- 2002-02-21 BR BR0207829-5A patent/BR0207829A/pt not_active Application Discontinuation
- 2002-02-21 ES ES02707927T patent/ES2275844T3/es not_active Expired - Lifetime
- 2002-02-21 AU AU2002242296A patent/AU2002242296B2/en not_active Ceased
- 2002-02-21 CN CNB028089235A patent/CN1262271C/zh not_active Expired - Fee Related
- 2002-02-21 KR KR1020037011292A patent/KR100886578B1/ko not_active Expired - Lifetime
- 2002-02-21 AT AT02707927T patent/ATE346597T1/de active
- 2002-02-21 HU HU0303342A patent/HUP0303342A3/hu unknown
- 2002-02-21 RU RU2003128983/14A patent/RU2302240C2/ru active
- 2002-02-21 CZ CZ20032297A patent/CZ302412B6/cs not_active IP Right Cessation
- 2002-02-21 PL PL02365021A patent/PL365021A1/xx unknown
- 2002-02-21 CA CA2439480A patent/CA2439480C/en not_active Expired - Fee Related
- 2002-02-21 RS YUP-675/03A patent/RS51056B/sr unknown
- 2002-02-21 NZ NZ527991A patent/NZ527991A/en unknown
- 2002-02-21 PT PT02707927T patent/PT1401424E/pt unknown
- 2002-02-21 DK DK02707927T patent/DK1401424T3/da active
- 2002-02-21 DE DE60216457T patent/DE60216457T2/de not_active Expired - Lifetime
- 2002-02-21 EP EP02707927A patent/EP1401424B1/en not_active Expired - Lifetime
- 2002-02-21 IL IL15758802A patent/IL157588A0/xx unknown
- 2002-02-21 WO PCT/US2002/006119 patent/WO2002067927A1/en not_active Ceased
- 2002-02-21 MX MXPA03007722A patent/MXPA03007722A/es active IP Right Grant
- 2002-02-27 AR ARP020100702A patent/AR032876A1/es unknown
- 2002-03-05 TW TW091103972A patent/TWI251486B/zh not_active IP Right Cessation
-
2003
- 2003-08-26 IL IL157588A patent/IL157588A/en not_active IP Right Cessation
- 2003-08-26 NO NO20033801A patent/NO20033801L/no not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6103759A (en) * | 1996-01-16 | 2000-08-15 | Sk Corporation | Halogen substituted carbamate compounds from 2-phenyl-1, 2-ethanediol |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014142549A1 (en) * | 2013-03-12 | 2014-09-18 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compound and a composition for preventing or treating a memory loss-related disease comprising the same |
| WO2014142550A1 (en) * | 2013-03-12 | 2014-09-18 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compound and a composition for preventing or treating a psychiatric disorder comprising the same |
| WO2014142547A1 (en) * | 2013-03-12 | 2014-09-18 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compound and a composition for neuroprotection comprising the same |
| WO2014142548A1 (en) * | 2013-03-12 | 2014-09-18 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compound and a composition for preventing or treating a nerve gas-induced disease comprising the same |
| US9457003B2 (en) | 2013-03-12 | 2016-10-04 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compound and a composition for preventing or treating a nerve gas-induced disease comprising the same |
| US9566261B2 (en) | 2013-03-12 | 2017-02-14 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compound and a composition for preventing or treating a memory loss-related disease comprising the same |
| KR101739677B1 (ko) | 2013-03-12 | 2017-05-24 | (주)바이오팜솔루션즈 | 페닐카바메이트 화합물 및 이를 포함하는 정신 질환의 예방 또는 치료용 조성물 |
| US9682059B2 (en) | 2013-03-12 | 2017-06-20 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compounds for use in preventing or treating epilepsy or epilepsy-related syndrome |
| US9872847B2 (en) | 2013-03-12 | 2018-01-23 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compounds for use in preventing or treating a movement disorder |
| US9907776B2 (en) | 2013-03-12 | 2018-03-06 | Bio-Pharm Solutions, Co., Ltd. | Phenyl carbamate compound and a composition for preventing or treating a psychiatric disorder comprising the same |
| US10525030B2 (en) | 2013-03-12 | 2020-01-07 | Bio-Pharm Solutions Co., Ltd. | Phenyl carbamate compound and a composition for neuroprotection comprising the same |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101783632B1 (ko) | 주의력 결핍/과잉행동 장애(ａｄｈｄ)의 치료 방법 | |
| KR101335941B1 (ko) | 수면-각성 장애의 치료 | |
| JP2010531879A (ja) | 水素化ピリド［４，３−ｂ］インドールに基づく抗不安作用を示す薬物、その薬理学的な化合物および適用方法 | |
| KR100886578B1 (ko) | 카바메이트 화합물을 포함하는 정신증 장애 예방용 또는 치료용 약제학적 조성물 | |
| KR20080089405A (ko) | 신경보호제로써 벤조-융합된 헤테로사이클 설파미드유도체의 용도 | |
| TWI250872B (en) | Carbamate compounds for use in preventing or treating bipolar disorder | |
| HK1247847A1 (zh) | 四氢-N，N-二甲基-2，2-二苯基-3-呋喃甲胺的对映体(ANAVEX2-73)及其在治疗阿尔海默氏病和其他由σ1受体调节的疾病中的用途 | |
| AU2002242296A1 (en) | Carbamate compounds for use in preventing or treating psychotic disorders | |
| KR101199499B1 (ko) | 물질 관련 장애를 치료하는 방법 | |
| Zhang et al. | Neurotoxicity and toxicokinetics of norfloxacin in conscious rats | |
| US20230201150A1 (en) | The combination of acetyl leucine and 4-aminopyridine or acetazolamide for treating ataxia | |
| ZA200307469B (en) | Carbamate compounds for use in preventing or treating psychotic disorders. | |
| WO2024226995A1 (en) | Compositions and methods for treating post-traumatic stress disorder | |
| CN119923255A (zh) | 用于改善记忆和认知的组合物和方法 | |
| Kertész et al. | P. 1. c. 044 Improvement of AMPA antagonist activity by methyl substitution on the aniline ring of 2, 3-benzodiazepine derivatives | |
| HK1209058B (en) | Compositions for treating drug addiction and improving addiction-related behavior | |
| HK1209058A1 (en) | Compositions for treating drug addiction and improving addiction-related behavior | |
| HK1176285B (en) | Compositions for treating drug addiction and improving addiction-related behavior |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20030827 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20070220 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20080324 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20081126 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20090225 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20090226 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20111215 Start annual number: 4 End annual number: 4 |
|
| FPAY | Annual fee payment |
Payment date: 20130111 Year of fee payment: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20130111 Start annual number: 5 End annual number: 5 |
|
| FPAY | Annual fee payment |
Payment date: 20140122 Year of fee payment: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20140122 Start annual number: 6 End annual number: 6 |
|
| FPAY | Annual fee payment |
Payment date: 20150128 Year of fee payment: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20150128 Start annual number: 7 End annual number: 7 |
|
| FPAY | Annual fee payment |
Payment date: 20160122 Year of fee payment: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20160122 Start annual number: 8 End annual number: 8 |
|
| FPAY | Annual fee payment |
Payment date: 20170106 Year of fee payment: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20170106 Start annual number: 9 End annual number: 9 |
|
| FPAY | Annual fee payment |
Payment date: 20171213 Year of fee payment: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20171213 Start annual number: 10 End annual number: 10 |
|
| FPAY | Annual fee payment |
Payment date: 20181227 Year of fee payment: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20181227 Start annual number: 11 End annual number: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20200108 Year of fee payment: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20200108 Start annual number: 12 End annual number: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20210104 Start annual number: 13 End annual number: 13 |
|
| PC1801 | Expiration of term |
Termination date: 20220821 Termination category: Expiration of duration |