JP2010509310A - ３−ベンジル−２−メチル−２，３，３ａ，４，５，６，７，７ａ−オクタヒドロベンゾ［ｄ］イソオキサゾール−４−オンの塩 - Google Patents
３−ベンジル−２−メチル−２，３，３ａ，４，５，６，７，７ａ−オクタヒドロベンゾ［ｄ］イソオキサゾール−４−オンの塩 Download PDFInfo
- Publication number
- JP2010509310A JP2010509310A JP2009535825A JP2009535825A JP2010509310A JP 2010509310 A JP2010509310 A JP 2010509310A JP 2009535825 A JP2009535825 A JP 2009535825A JP 2009535825 A JP2009535825 A JP 2009535825A JP 2010509310 A JP2010509310 A JP 2010509310A
- Authority
- JP
- Japan
- Prior art keywords
- oxalate
- formula
- salt
- compound
- medicament
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 22
- ALQXIMVNPRVWQA-UHFFFAOYSA-N 3-benzyl-2-methyl-3,3a,5,6,7,7a-hexahydro-1,2-benzoxazol-4-one Chemical compound CN1OC2CCCC(=O)C2C1CC1=CC=CC=C1 ALQXIMVNPRVWQA-UHFFFAOYSA-N 0.000 title claims description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 99
- 239000003814 drug Substances 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 150000003891 oxalate salts Chemical class 0.000 claims abstract description 30
- 229940079593 drug Drugs 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 9
- 208000020401 Depressive disease Diseases 0.000 claims abstract description 9
- 206010013654 Drug abuse Diseases 0.000 claims abstract description 9
- 208000019022 Mood disease Diseases 0.000 claims abstract description 9
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 9
- 206010048010 Withdrawal syndrome Diseases 0.000 claims abstract description 9
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 9
- 208000000044 Amnesia Diseases 0.000 claims abstract description 7
- 208000031091 Amnestic disease Diseases 0.000 claims abstract description 7
- 230000006986 amnesia Effects 0.000 claims abstract description 7
- 230000002920 convulsive effect Effects 0.000 claims abstract description 7
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims abstract 2
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 22
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 22
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 22
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 239000000454 talc Substances 0.000 claims description 17
- 229910052623 talc Inorganic materials 0.000 claims description 17
- 239000012458 free base Substances 0.000 claims description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 14
- 229920003109 sodium starch glycolate Polymers 0.000 claims description 12
- 239000008109 sodium starch glycolate Substances 0.000 claims description 12
- 229940079832 sodium starch glycolate Drugs 0.000 claims description 12
- 235000006408 oxalic acid Nutrition 0.000 claims description 8
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 7
- 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 claims description 7
- 229930195725 Mannitol Natural products 0.000 claims description 7
- 229920002472 Starch Polymers 0.000 claims description 7
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 7
- 229930006000 Sucrose Natural products 0.000 claims description 7
- 239000008101 lactose Substances 0.000 claims description 7
- 235000019359 magnesium stearate Nutrition 0.000 claims description 7
- 239000000594 mannitol Substances 0.000 claims description 7
- 235000010355 mannitol Nutrition 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 229940032147 starch Drugs 0.000 claims description 7
- 239000008107 starch Substances 0.000 claims description 7
- 235000019698 starch Nutrition 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- 238000011200 topical administration Methods 0.000 claims description 6
- 238000007911 parenteral administration Methods 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 3
- 206010027175 memory impairment Diseases 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- 206010010904 Convulsion Diseases 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 230000036461 convulsion Effects 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 150000004683 dihydrates Chemical class 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 235000013681 dietary sucrose Nutrition 0.000 claims 1
- 229960001375 lactose Drugs 0.000 claims 1
- 229940057948 magnesium stearate Drugs 0.000 claims 1
- 229960001855 mannitol Drugs 0.000 claims 1
- 229960004274 stearic acid Drugs 0.000 claims 1
- 229960004793 sucrose Drugs 0.000 claims 1
- 229940033134 talc Drugs 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
- 238000013112 stability test Methods 0.000 description 13
- 239000012535 impurity Substances 0.000 description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 10
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000005720 sucrose Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- JGRCHNVLXORPNM-UHFFFAOYSA-N 1,2-oxazol-4-one Chemical compound O=C1CON=C1 JGRCHNVLXORPNM-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 231100000460 acute oral toxicity Toxicity 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000003304 gavage Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LEPHADHYDPOCOO-UHFFFAOYSA-N 3-benzyl-2-methyl-3a,4,5,6,7,7a-hexahydro-3h-1,2-benzoxazole Chemical compound CN1OC2CCCCC2C1CC1=CC=CC=C1 LEPHADHYDPOCOO-UHFFFAOYSA-N 0.000 description 1
- 208000003918 Acute Kidney Tubular Necrosis Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- HAPUAKFDAHBRLX-UHFFFAOYSA-N CN(C(CCc1ccccc1)C12)OC1C=CCC2=O Chemical compound CN(C(CCc1ccccc1)C12)OC1C=CCC2=O HAPUAKFDAHBRLX-UHFFFAOYSA-N 0.000 description 1
- UQZXWQAXHGRSHY-UHFFFAOYSA-N CN1OC(CCC(C2)C=O)C2C1CCc1ccccc1 Chemical compound CN1OC(CCC(C2)C=O)C2C1CCc1ccccc1 UQZXWQAXHGRSHY-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 208000008457 Neurologic Manifestations Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010038540 Renal tubular necrosis 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
- 206010041349 Somnolence Diseases 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- -1 auxiliaries Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- MEWULGVKRKSPIQ-UHFFFAOYSA-N oxalic acid 1,2-oxazol-4-one Chemical compound C(C(=O)O)(=O)O.O1N=CC(C1)=O MEWULGVKRKSPIQ-UHFFFAOYSA-N 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT002102A ITMI20062102A1 (it) | 2006-11-02 | 2006-11-02 | Nuovui sali di 3-benzil-2-metil-2,3,3a,4,5,6,7,7a-ottaidrobenzo-d-isossazol-4-one |
| PCT/IB2007/003292 WO2008053326A1 (en) | 2006-11-02 | 2007-10-31 | A salt of 3-benzyl-2-methyl-2,3,3a,4,5,6,7,7a-octahydrobenzo[d]isoxazol-4-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2010509310A true JP2010509310A (ja) | 2010-03-25 |
Family
ID=39145485
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009535825A Pending JP2010509310A (ja) | 2006-11-02 | 2007-10-31 | ３−ベンジル−２−メチル−２，３，３ａ，４，５，６，７，７ａ−オクタヒドロベンゾ［ｄ］イソオキサゾール−４−オンの塩 |
| JP2009535824A Pending JP2010509309A (ja) | 2006-11-02 | 2007-10-31 | ３−ベンジル−２−メチル−２，３，３ａ，４，５，６，７，７ａ−オクタヒドロベンゾ［ｄ］イソオキサゾール−４−オンの塩 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009535824A Pending JP2010509309A (ja) | 2006-11-02 | 2007-10-31 | ３−ベンジル−２−メチル−２，３，３ａ，４，５，６，７，７ａ−オクタヒドロベンゾ［ｄ］イソオキサゾール−４−オンの塩 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20100069451A1 (enExample) |
| EP (2) | EP2094675B1 (enExample) |
| JP (2) | JP2010509310A (enExample) |
| KR (2) | KR20090077014A (enExample) |
| CN (2) | CN101535281A (enExample) |
| AT (2) | ATE502021T1 (enExample) |
| AU (2) | AU2007315832A1 (enExample) |
| BR (2) | BRPI0718391A2 (enExample) |
| CA (2) | CA2667513A1 (enExample) |
| DE (2) | DE602007013801D1 (enExample) |
| HR (2) | HRP20090477A2 (enExample) |
| IL (2) | IL198444A0 (enExample) |
| IT (1) | ITMI20062102A1 (enExample) |
| MX (2) | MX2009004293A (enExample) |
| NO (2) | NO20092114L (enExample) |
| NZ (2) | NZ577311A (enExample) |
| RS (2) | RS20090389A (enExample) |
| RU (2) | RU2009120667A (enExample) |
| WO (2) | WO2008053326A1 (enExample) |
| ZA (2) | ZA200903618B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20080768A1 (it) * | 2008-04-24 | 2009-10-25 | Abiogen Pharma Spa | Procedimento per la preparazione di un composto in forma cristallina di 3-benzil-2-metil-2,3,3a,4,5,6,7,7a-ottaidro-benzo[d]isossazol-4-one |
| EP2112142A1 (en) * | 2008-04-24 | 2009-10-28 | Abiogen Pharma S.p.A. | Process for preparing a crystalline form compound of 3-benzyl-2-methyl-2,3,3a,4,5,6,7,7a-octahydrobenzo[d]isoxazol-4-one |
| EP2218721A1 (en) * | 2009-02-11 | 2010-08-18 | LEK Pharmaceuticals d.d. | Novel salts of sitagliptin |
| WO2011010332A1 (en) * | 2009-07-23 | 2011-01-27 | Abiogen Pharma S.P.A. | Process for preparing rel-(3r*,3as*,7as*)-3-benzyl-2-methyl-2,3, 3a,4,5,6,7,7a- octahydrobenzo[d]isoxazoi-4-one or a salt thereof |
| EP3250569B1 (en) * | 2015-01-30 | 2019-01-09 | Boehringer Ingelheim International GmbH | Aldosterone synthase inhibitors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07504181A (ja) * | 1992-02-19 | 1995-05-11 | ビーティージー・インターナショナル・リミテッド | ベンズイソキサゾール誘導体及びそれらを含む医薬組成物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4161595A (en) * | 1978-10-02 | 1979-07-17 | Bristol-Myers Company | Levulinic acid salt |
| US4419358A (en) * | 1981-11-12 | 1983-12-06 | Mead Johnson & Company | Isethionic acid salt of 9-cyclohexyl-2-propoxy-9H-purine-6-amine and compositions containing an effective bronchodilating concentration of it |
-
2006
- 2006-11-02 IT IT002102A patent/ITMI20062102A1/it unknown
-
2007
- 2007-10-31 MX MX2009004293A patent/MX2009004293A/es not_active Application Discontinuation
- 2007-10-31 CN CNA2007800406598A patent/CN101535281A/zh active Pending
- 2007-10-31 RU RU2009120667/04A patent/RU2009120667A/ru not_active Application Discontinuation
- 2007-10-31 EP EP07825550A patent/EP2094675B1/en not_active Not-in-force
- 2007-10-31 DE DE602007013801T patent/DE602007013801D1/de active Active
- 2007-10-31 RU RU2009120724/04A patent/RU2009120724A/ru not_active Application Discontinuation
- 2007-10-31 BR BRPI0718391-7A patent/BRPI0718391A2/pt not_active IP Right Cessation
- 2007-10-31 BR BRPI0718392-5A patent/BRPI0718392A2/pt not_active IP Right Cessation
- 2007-10-31 WO PCT/IB2007/003292 patent/WO2008053326A1/en not_active Ceased
- 2007-10-31 CN CNA2007800406691A patent/CN101535282A/zh active Pending
- 2007-10-31 HR HR20090477A patent/HRP20090477A2/hr not_active Application Discontinuation
- 2007-10-31 AT AT07825549T patent/ATE502021T1/de not_active IP Right Cessation
- 2007-10-31 AT AT07825550T patent/ATE504578T1/de not_active IP Right Cessation
- 2007-10-31 AU AU2007315832A patent/AU2007315832A1/en not_active Abandoned
- 2007-10-31 NZ NZ577311A patent/NZ577311A/en unknown
- 2007-10-31 NZ NZ577978A patent/NZ577978A/en unknown
- 2007-10-31 MX MX2009004294A patent/MX2009004294A/es not_active Application Discontinuation
- 2007-10-31 HR HR20090470A patent/HRP20090470A2/hr not_active Application Discontinuation
- 2007-10-31 CA CA002667513A patent/CA2667513A1/en not_active Abandoned
- 2007-10-31 AU AU2007315833A patent/AU2007315833A1/en not_active Abandoned
- 2007-10-31 US US12/513,352 patent/US20100069451A1/en not_active Abandoned
- 2007-10-31 RS RSP-2009/0389A patent/RS20090389A/sr unknown
- 2007-10-31 US US12/513,351 patent/US20100069450A1/en not_active Abandoned
- 2007-10-31 JP JP2009535825A patent/JP2010509310A/ja active Pending
- 2007-10-31 DE DE602007013278T patent/DE602007013278D1/de active Active
- 2007-10-31 KR KR1020097011287A patent/KR20090077014A/ko not_active Withdrawn
- 2007-10-31 RS RSP-2009/0388A patent/RS20090388A/sr unknown
- 2007-10-31 JP JP2009535824A patent/JP2010509309A/ja active Pending
- 2007-10-31 KR KR1020097011322A patent/KR20090082452A/ko not_active Withdrawn
- 2007-10-31 EP EP07825549A patent/EP2094674B1/en not_active Not-in-force
- 2007-10-31 WO PCT/IB2007/003291 patent/WO2008053325A1/en not_active Ceased
- 2007-10-31 CA CA002667515A patent/CA2667515A1/en not_active Abandoned
-
2009
- 2009-04-28 IL IL198444A patent/IL198444A0/en unknown
- 2009-04-28 IL IL198443A patent/IL198443A0/en unknown
- 2009-05-25 ZA ZA200903618A patent/ZA200903618B/xx unknown
- 2009-05-29 NO NO20092114A patent/NO20092114L/no not_active Application Discontinuation
- 2009-05-29 NO NO20092115A patent/NO20092115L/no not_active Application Discontinuation
- 2009-06-01 ZA ZA200903810A patent/ZA200903810B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07504181A (ja) * | 1992-02-19 | 1995-05-11 | ビーティージー・インターナショナル・リミテッド | ベンズイソキサゾール誘導体及びそれらを含む医薬組成物 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5268902B2 (ja) | ピロロピリミジノン誘導体の塩およびその製造方法 | |
| CH639653A5 (fr) | Aminothiazoles et composition pharmaceutique les contenant. | |
| HUE026408T2 (en) | Dabigatran etexylate bis-mesylate salt, solid forms and process for their preparation | |
| AU661483B2 (en) | Crystalline tiagabine hydrochloride monohydrate, its preparation and use | |
| JP2010509310A (ja) | ３−ベンジル−２−メチル−２，３，３ａ，４，５，６，７，７ａ−オクタヒドロベンゾ［ｄ］イソオキサゾール−４−オンの塩 | |
| HUE029847T2 (en) | Optimized synthesis of pure non-polymorphic bile acids having a defined particle size | |
| FR2776660A1 (fr) | Diazepino-indoles de phosphodiesterases iv | |
| CN101404997A (zh) | 度洛西汀盐 | |
| FR2883285A1 (fr) | Sel besylate de la 7-(2-(4-(3-trifluoromethyl-phenyl) -1,2,3,6-tetrahudro-pyrid-1-yl)ethyl) isoquinoleine, sa preparation et son utilisation en therapeutique | |
| EP2271343A1 (fr) | Sels de quinoleines 2-substituees | |
| CN106478616B (zh) | 一种gpr40激动剂的结晶形式及其制备方法 | |
| NL8603236A (nl) | Optisch actieve 2-chloor-12-(3-dimethylamino-2-methyl-propyl)-12h-dibenzod,g1,3,6dioxazocinen en een werkwijze voor de bereiding ervan. | |
| JPH0341459B2 (enExample) | ||
| KR20130036210A (ko) | 신규 다형체 및 염 | |
| JP3001975B2 (ja) | 結晶性チアガビン塩酸塩−水和物、その製造方法および用途 | |
| FR2566775A1 (fr) | Derives de tetrahydro-4,5,6,7 furo ou 1h-pyrrolo(2,3-c)pyridine, leur preparation et leur application en therapeutique | |
| KR20220154791A (ko) | (1r,3s)-3-(5-시아노-4-페닐-1,3-티아졸-2-일카바모일)사이클로펜탄 카복실산의 공결정 | |
| KR20070094230A (ko) | 클로피도그렐 캄파술폰산염 또는 이의 결정다형을 함유하는약학 조성물 | |
| JP2021531329A (ja) | ベンゾチオフェン化合物のマレイン酸塩、その結晶形式及びその用途 | |
| HK1174608A (en) | Novel polymorphs and salts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20101019 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20101025 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20101019 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20121122 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20130515 |