JPH0381277A - ２―オキソ―３，８―ジアザスピロ〔４，５〕デカン誘導体，それを含む医薬組成物及びその製造方法 - Google Patents
２―オキソ―３，８―ジアザスピロ〔４，５〕デカン誘導体，それを含む医薬組成物及びその製造方法Info
- Publication number
- JPH0381277A JPH0381277A JP2209362A JP20936290A JPH0381277A JP H0381277 A JPH0381277 A JP H0381277A JP 2209362 A JP2209362 A JP 2209362A JP 20936290 A JP20936290 A JP 20936290A JP H0381277 A JPH0381277 A JP H0381277A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- oxo
- diazaspiro
- group
- decane
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- ASPBBYVNTMIKLA-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decan-3-one Chemical class C1NC(=O)CC21CCNCC2 ASPBBYVNTMIKLA-UHFFFAOYSA-N 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 62
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- -1 methylsulfonyloxy Chemical group 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 16
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
- DTNXRKYDRUCILN-UHFFFAOYSA-N (4-acetylpiperidin-4-yl) carbamate Chemical class NC(=O)OC1(C(=O)C)CCNCC1 DTNXRKYDRUCILN-UHFFFAOYSA-N 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 230000036571 hydration Effects 0.000 claims description 2
- 238000006703 hydration reaction Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 230000003204 osmotic effect Effects 0.000 claims 2
- 239000003002 pH adjusting agent Substances 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims 2
- YMANQWHUUFJQOW-UHFFFAOYSA-N 1,2-diazaspiro[4.5]decane Chemical class N1NCCC11CCCCC1 YMANQWHUUFJQOW-UHFFFAOYSA-N 0.000 claims 1
- PAPJZJIQQXETDJ-UHFFFAOYSA-N 1-methylidene-2,8-diazaspiro[4.5]decan-3-one Chemical class C=C1NC(=O)CC11CCNCC1 PAPJZJIQQXETDJ-UHFFFAOYSA-N 0.000 claims 1
- IIOHDEHWJZVISP-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)but-3-enyl]-3-butyl-4-hydroxy-4-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one;hydrochloride Chemical compound Cl.CC1(O)N(CCCC)C(=O)OC11CCN(CCC=C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 IIOHDEHWJZVISP-UHFFFAOYSA-N 0.000 claims 1
- IEFWYEJWJNWYKN-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)but-3-enyl]-3-tert-butyl-4-hydroxy-4-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one;hydrochloride Chemical compound Cl.CC1(O)N(C(C)(C)C)C(=O)OC11CCN(CCC=C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 IEFWYEJWJNWYKN-UHFFFAOYSA-N 0.000 claims 1
- WKMXAZFERDLNIA-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)but-3-enyl]-4-hydroxy-3,4-dimethyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one;hydrochloride Chemical compound Cl.CC1(O)N(C)C(=O)OC11CCN(CCC=C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 WKMXAZFERDLNIA-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZDFMXEWTPFAMSB-UHFFFAOYSA-N Cl.N1NCCC11CCCCC1 Chemical compound Cl.N1NCCC11CCCCC1 ZDFMXEWTPFAMSB-UHFFFAOYSA-N 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 241001465754 Metazoa Species 0.000 description 22
- 238000000354 decomposition reaction Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 210000004556 brain Anatomy 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 206010021143 Hypoxia Diseases 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 239000003826 tablet Substances 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OYKIERKRPUDEIV-UHFFFAOYSA-N decane;hydrochloride Chemical compound Cl.CCCCCCCCCC OYKIERKRPUDEIV-UHFFFAOYSA-N 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 6
- 230000001146 hypoxic effect Effects 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 206010048962 Brain oedema Diseases 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 239000000047 product Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 230000003137 locomotive effect Effects 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000010627 oxidative phosphorylation Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229960004526 piracetam Drugs 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- ABWVLWHPVBHFLQ-UHFFFAOYSA-M sodium;2-oxo-3-phenylpropanoate;hydrate Chemical compound O.[Na+].[O-]C(=O)C(=O)CC1=CC=CC=C1 ABWVLWHPVBHFLQ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical group C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU4094/89 | 1989-08-10 | ||
| HU894094A HU204276B (en) | 1989-08-10 | 1989-08-10 | Process for producing new 1-oxa-2-oxo-4-methylen-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0381277A true JPH0381277A (ja) | 1991-04-05 |
Family
ID=10966866
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2209362A Pending JPH0381277A (ja) | 1989-08-10 | 1990-08-09 | ２―オキソ―３，８―ジアザスピロ〔４，５〕デカン誘導体，それを含む医薬組成物及びその製造方法 |
| JP2209363A Pending JPH0383985A (ja) | 1989-08-10 | 1990-08-09 | 新規４―メチレン―２―オキソ―８―アザスピロ〔４，５〕デカン誘導体，それらを含む医薬組成物およびそれらの調整方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2209363A Pending JPH0383985A (ja) | 1989-08-10 | 1990-08-09 | 新規４―メチレン―２―オキソ―８―アザスピロ〔４，５〕デカン誘導体，それらを含む医薬組成物およびそれらの調整方法 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US5132309A (OSRAM) |
| EP (2) | EP0413516B1 (OSRAM) |
| JP (2) | JPH0381277A (OSRAM) |
| KR (2) | KR940002826B1 (OSRAM) |
| CN (1) | CN1025031C (OSRAM) |
| AT (2) | ATE104671T1 (OSRAM) |
| AU (2) | AU621771B2 (OSRAM) |
| CA (2) | CA2023015A1 (OSRAM) |
| DD (2) | DD299428A5 (OSRAM) |
| DE (2) | DE69014008T2 (OSRAM) |
| DK (1) | DK0413516T3 (OSRAM) |
| ES (2) | ES2063923T3 (OSRAM) |
| FI (1) | FI93456C (OSRAM) |
| HK (1) | HK118295A (OSRAM) |
| HU (2) | HU206677B (OSRAM) |
| IE (1) | IE902885A1 (OSRAM) |
| IL (2) | IL95325A (OSRAM) |
| IN (1) | IN170979B (OSRAM) |
| IS (1) | IS3612A7 (OSRAM) |
| MY (1) | MY107240A (OSRAM) |
| NO (1) | NO903511L (OSRAM) |
| NZ (2) | NZ234846A (OSRAM) |
| PL (2) | PL163899B1 (OSRAM) |
| SG (1) | SG59864G (OSRAM) |
| YU (2) | YU150489A (OSRAM) |
| ZA (3) | ZA906299B (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2074981T3 (es) * | 1986-12-17 | 1995-10-01 | Glaxo Group Ltd | Uso de derivados heterociclicos en el tratamiento de trastornos cognoscitivos. |
| HU204529B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| YU150489A (sh) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
| US5534520A (en) * | 1990-04-10 | 1996-07-09 | Fisher; Abraham | Spiro compounds containing five-membered rings |
| US5852029A (en) * | 1990-04-10 | 1998-12-22 | Israel Institute For Biological Research | Aza spiro compounds acting on the cholinergic system with muscarinic agonist activity |
| EP0492020A1 (en) * | 1990-12-21 | 1992-07-01 | Merrell Dow Pharmaceuticals Inc. | Use of certain esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one and related compounds for treating cognitive disorders |
| GB9206989D0 (en) * | 1992-03-31 | 1992-05-13 | Glaxo Group Ltd | Chemical compounds |
| US5756743A (en) | 1996-04-10 | 1998-05-26 | Hoechst Marion Roussel Inc. | Spiro cyclopent b!indole-piperidines! |
| US6100256A (en) * | 1996-12-02 | 2000-08-08 | Merck Sharp & Dohme Ltd. | Use of NK-1 receptors antagonists for treating schizophrenic disorders |
| US6974825B1 (en) | 1996-12-20 | 2005-12-13 | Astrazeneca Canada Inc. | Compounds with analgesic effect |
| SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
| SE9904675D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
| SE0101770D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101771D0 (sv) | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101769D0 (sv) | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101773D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| KR20030087248A (ko) * | 2002-05-08 | 2003-11-14 | (주)씨엔아이 | 온라인을 통한 상거래 기초항목의 설정기능을 갖는 상거래관리장치 |
| EP2443124B1 (en) * | 2009-06-16 | 2014-01-22 | Merck Sharp & Dohme Corp. | Substituted -1,3,8-triazaspiro[4.5]decane-2,4-diones |
| GB201416352D0 (en) * | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Spirocyclic derivatives |
| GB201416346D0 (en) * | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Spirocyclic derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL127065C (OSRAM) * | 1964-04-22 | |||
| CH601304A5 (OSRAM) * | 1974-02-12 | 1978-07-14 | Buskine Sa | |
| BE790675A (fr) * | 1971-10-29 | 1973-04-27 | Science Union & Cie | Nouveaux derives de l'oxa-1 diaza-3,8 spiro (4,5) decane |
| FR2615515B1 (fr) * | 1987-05-22 | 1989-06-30 | Adir | Nouveaux derives du spiro 4, 5 decane, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| HU204530B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| HU204529B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| YU150489A (sh) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
-
1989
- 1989-07-27 YU YU150489A patent/YU150489A/sh unknown
- 1989-08-10 HU HU903233A patent/HU206677B/hu not_active IP Right Cessation
- 1989-08-10 HU HU894094A patent/HU204276B/hu not_active IP Right Cessation
-
1990
- 1990-08-08 KR KR1019900012168A patent/KR940002826B1/ko not_active Expired - Fee Related
- 1990-08-08 KR KR1019900012169A patent/KR940000830B1/ko not_active Expired - Fee Related
- 1990-08-09 EP EP90308783A patent/EP0413516B1/en not_active Expired - Lifetime
- 1990-08-09 CA CA002023015A patent/CA2023015A1/en not_active Abandoned
- 1990-08-09 IN IN687/CAL/90A patent/IN170979B/en unknown
- 1990-08-09 IS IS3612A patent/IS3612A7/is unknown
- 1990-08-09 ES ES90308779T patent/ES2063923T3/es not_active Expired - Lifetime
- 1990-08-09 IL IL9532590A patent/IL95325A/en not_active IP Right Cessation
- 1990-08-09 DD DD90343354A patent/DD299428A5/de not_active IP Right Cessation
- 1990-08-09 DE DE69014008T patent/DE69014008T2/de not_active Expired - Fee Related
- 1990-08-09 DK DK90308783.1T patent/DK0413516T3/da active
- 1990-08-09 NZ NZ234846A patent/NZ234846A/en unknown
- 1990-08-09 DE DE69008275T patent/DE69008275T2/de not_active Expired - Fee Related
- 1990-08-09 ZA ZA906299A patent/ZA906299B/xx unknown
- 1990-08-09 JP JP2209362A patent/JPH0381277A/ja active Pending
- 1990-08-09 JP JP2209363A patent/JPH0383985A/ja active Pending
- 1990-08-09 IL IL9532490A patent/IL95324A/en not_active IP Right Cessation
- 1990-08-09 YU YU154090A patent/YU154090A/sh unknown
- 1990-08-09 SG SG1995903969A patent/SG59864G/en unknown
- 1990-08-09 NZ NZ234843A patent/NZ234843A/en unknown
- 1990-08-09 IE IE288590A patent/IE902885A1/en unknown
- 1990-08-09 ZA ZA906300A patent/ZA906300B/xx unknown
- 1990-08-09 AT AT9090308783T patent/ATE104671T1/de not_active IP Right Cessation
- 1990-08-09 EP EP90308779A patent/EP0412821B1/en not_active Expired - Lifetime
- 1990-08-09 ES ES90308783T patent/ES2052179T3/es not_active Expired - Lifetime
- 1990-08-09 AU AU60803/90A patent/AU621771B2/en not_active Ceased
- 1990-08-09 DD DD90343359A patent/DD299431A5/de not_active IP Right Cessation
- 1990-08-09 ZA ZA906304A patent/ZA906304B/xx unknown
- 1990-08-09 CA CA002023018A patent/CA2023018C/en not_active Expired - Fee Related
- 1990-08-09 NO NO90903511A patent/NO903511L/no unknown
- 1990-08-09 AU AU60804/90A patent/AU621238B2/en not_active Ceased
- 1990-08-09 AT AT90308779T patent/ATE113951T1/de not_active IP Right Cessation
- 1990-08-10 MY MYPI90001343A patent/MY107240A/en unknown
- 1990-08-10 FI FI903974A patent/FI93456C/fi not_active IP Right Cessation
- 1990-08-10 PL PL90286443A patent/PL163899B1/pl unknown
- 1990-08-10 US US07/566,279 patent/US5132309A/en not_active Expired - Fee Related
- 1990-08-10 US US07/566,278 patent/US5132303A/en not_active Expired - Fee Related
- 1990-08-10 PL PL90291648A patent/PL164662B1/pl unknown
- 1990-08-10 CN CN90106974A patent/CN1025031C/zh not_active Expired - Fee Related
-
1995
- 1995-07-20 HK HK118295A patent/HK118295A/en not_active IP Right Cessation
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