HRP20090470A2 - Sol 3-benzil-2-methil-2.3.3.a.4.5.6.7,7a-octahidrobenzo[d]isoksazol-4-ona - Google Patents
Sol 3-benzil-2-methil-2.3.3.a.4.5.6.7,7a-octahidrobenzo[d]isoksazol-4-ona Download PDFInfo
- Publication number
- HRP20090470A2 HRP20090470A2 HR20090470A HRP20090470A HRP20090470A2 HR P20090470 A2 HRP20090470 A2 HR P20090470A2 HR 20090470 A HR20090470 A HR 20090470A HR P20090470 A HRP20090470 A HR P20090470A HR P20090470 A2 HRP20090470 A2 HR P20090470A2
- Authority
- HR
- Croatia
- Prior art keywords
- oxalate salt
- oxalate
- compound
- drug
- salt
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims description 23
- 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 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 150000003891 oxalate salts Chemical class 0.000 claims abstract description 53
- 239000003814 drug Substances 0.000 claims abstract description 27
- 229940079593 drug Drugs 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 208000000044 Amnesia Diseases 0.000 claims abstract description 10
- 208000031091 Amnestic disease Diseases 0.000 claims abstract description 10
- 230000006986 amnesia Effects 0.000 claims abstract description 10
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 9
- 208000019022 Mood disease Diseases 0.000 claims abstract description 9
- 230000002920 convulsive effect Effects 0.000 claims abstract description 9
- 230000036506 anxiety Effects 0.000 claims abstract description 8
- 230000006872 improvement Effects 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 4
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 22
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 22
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 22
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 22
- 239000003826 tablet Substances 0.000 claims description 17
- 239000000454 talc Substances 0.000 claims description 17
- 229910052623 talc Inorganic materials 0.000 claims description 17
- 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 claims description 16
- 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
- 239000000243 solution Substances 0.000 claims description 11
- 206010013654 Drug abuse Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 208000011117 substance-related disease Diseases 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
- 229920000881 Modified 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
- 235000006408 oxalic acid Nutrition 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- 239000005720 sucrose Substances 0.000 claims description 7
- 206010013754 Drug withdrawal syndrome Diseases 0.000 claims description 6
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000007911 parenteral administration Methods 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000000725 suspension 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
- 229920002472 Starch Polymers 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 150000004683 dihydrates Chemical group 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000000499 gel 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
- 229940032147 starch Drugs 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- NIFHFRBCEUSGEE-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O NIFHFRBCEUSGEE-UHFFFAOYSA-N 0.000 claims 2
- JGRCHNVLXORPNM-UHFFFAOYSA-N 1,2-oxazol-4-one Chemical compound O=C1CON=C1 JGRCHNVLXORPNM-UHFFFAOYSA-N 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- -1 oxalate compound Chemical class 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 239000012535 impurity Substances 0.000 description 16
- 238000003860 storage Methods 0.000 description 15
- 238000013112 stability test Methods 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000000354 decomposition reaction 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000002904 solvent Substances 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000003304 gavage Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
- 150000003890 succinate salts Chemical class 0.000 description 2
- 210000005239 tubule Anatomy 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 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 1
- 208000003918 Acute Kidney Tubular Necrosis Diseases 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical group CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-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
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- 206010060860 Neurological symptom Diseases 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010038540 Renal tubular necrosis Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 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
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect 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
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000002689 maleic acids Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 231100000418 oral toxicity Toxicity 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
- 230000007170 pathology Effects 0.000 description 1
- 238000004321 preservation Methods 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
- 230000002441 reversible effect Effects 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
- 238000003756 stirring Methods 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (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 (fr) | 2006-11-02 | 2007-10-31 | Sel de 3-benzyl-2-méthyl-2,3,3a,4,5,6,7,7a-octahydrobenzo[d]isoxazol-4-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090470A2 true HRP20090470A2 (hr) | 2009-11-30 |
Family
ID=39145485
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090470A HRP20090470A2 (hr) | 2006-11-02 | 2009-09-03 | Sol 3-benzil-2-methil-2.3.3.a.4.5.6.7,7a-octahidrobenzo[d]isoksazol-4-ona |
| HR20090477A HRP20090477A2 (hr) | 2006-11-02 | 2009-09-08 | SOL 3-BENZIL-2-METIL-2,3,3A,4,5,6,7,7A-OKTAHIDROBENZO[d]IZOKSAZOL-4-ONA |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090477A HRP20090477A2 (hr) | 2006-11-02 | 2009-09-08 | SOL 3-BENZIL-2-METIL-2,3,3A,4,5,6,7,7A-OKTAHIDROBENZO[d]IZOKSAZOL-4-ONA |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20100069451A1 (fr) |
| EP (2) | EP2094675B1 (fr) |
| JP (2) | JP2010509310A (fr) |
| KR (2) | KR20090082452A (fr) |
| CN (2) | CN101535282A (fr) |
| AT (2) | ATE502021T1 (fr) |
| AU (2) | AU2007315832A1 (fr) |
| BR (2) | BRPI0718391A2 (fr) |
| CA (2) | CA2667513A1 (fr) |
| DE (2) | DE602007013801D1 (fr) |
| HR (2) | HRP20090470A2 (fr) |
| IL (2) | IL198444A0 (fr) |
| IT (1) | ITMI20062102A1 (fr) |
| MX (2) | MX2009004294A (fr) |
| NO (2) | NO20092115L (fr) |
| NZ (2) | NZ577978A (fr) |
| RS (2) | RS20090389A (fr) |
| RU (2) | RU2009120667A (fr) |
| WO (2) | WO2008053326A1 (fr) |
| ZA (2) | ZA200903618B (fr) |
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 (fr) * | 2008-04-24 | 2009-10-28 | Abiogen Pharma S.p.A. | Procédé de préparation d'une forme cristalline du 3-benzyl-2-methyl-2,3,3a,4,5,6,7,7a-octahydrobenzo[d]isoxazol-4-one |
| EP2218721A1 (fr) * | 2009-02-11 | 2010-08-18 | LEK Pharmaceuticals d.d. | Nouveaux sels de sitagliptine |
| WO2011010332A1 (fr) * | 2009-07-23 | 2011-01-27 | Abiogen Pharma S.P.A. | Procédé de préparation de rel-(3r*,3as*,7as*)-3-benzyl-2-méthyl-2,3, 3a,4,5,6,7,7a-octahydrobenzo[d]isoxazol-4-one ou de l'un de ses sels |
| US10131642B1 (en) * | 2015-01-30 | 2018-11-20 | Boehringer Ingelheim International Gmbh | Aldosterone synthase inhibitors |
Family Cites Families (3)
| 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 |
| GB2264299B (en) * | 1992-02-19 | 1995-07-26 | British Tech Group | Iso-oxazolidine derivatives |
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