NL8401907A - Spirosuccinimiden en werkwijzen voor het bereiden en toepassen van deze spirosuccinimiden. - Google Patents
Spirosuccinimiden en werkwijzen voor het bereiden en toepassen van deze spirosuccinimiden. Download PDFInfo
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- NL8401907A NL8401907A NL8401907A NL8401907A NL8401907A NL 8401907 A NL8401907 A NL 8401907A NL 8401907 A NL8401907 A NL 8401907A NL 8401907 A NL8401907 A NL 8401907A NL 8401907 A NL8401907 A NL 8401907A
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- NL
- Netherlands
- Prior art keywords
- group
- carbon atoms
- formula
- alkyl
- compounds
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- 238000000034 method Methods 0.000 title claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 85
- -1 tetrahydro-benzocycloheptenyl group Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000006193 alkinyl group Chemical group 0.000 claims description 6
- FPWYXHKGPQQAAG-UHFFFAOYSA-N 3-oxodecanal Chemical compound CCCCCCCC(=O)CC=O FPWYXHKGPQQAAG-UHFFFAOYSA-N 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 206010020651 Hyperkinesia Diseases 0.000 claims description 3
- 208000000269 Hyperkinesis Diseases 0.000 claims description 3
- 206010026749 Mania Diseases 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 2
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- FHXFORFSIVKKDF-UHFFFAOYSA-N 2-ethyl-8-(2,2,2-trifluoroethyl)-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound O=C1N(CC)C(=O)CC11CCN(CC(F)(F)F)CC1 FHXFORFSIVKKDF-UHFFFAOYSA-N 0.000 claims 1
- REUYZVSLTRHIIU-UHFFFAOYSA-N 2-ethyl-8-methyl-8-oxido-2-aza-8-azoniaspiro[4.5]decane-1,3-dione Chemical compound O=C1N(CC)C(=O)CC11CC[N+](C)([O-])CC1 REUYZVSLTRHIIU-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 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
- 239000000725 suspension Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- UIHKDOBBVHGTAQ-UHFFFAOYSA-N 2-ethyl-8-methyl-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound O=C1N(CC)C(=O)CC11CCN(C)CC1 UIHKDOBBVHGTAQ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010008748 Chorea Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010039966 Senile dementia Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003727 cerebral blood flow Effects 0.000 description 2
- 208000012601 choreatic disease Diseases 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical class [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- NERNEXMEYQFFHU-UHFFFAOYSA-N 1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound N1C(=O)NC(=O)C11CCCCC1 NERNEXMEYQFFHU-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- HIBJEGRTZANTFJ-UHFFFAOYSA-N 2-(3-ethoxycarbonylpiperidin-3-yl)acetic acid Chemical compound C(C)OC(=O)C1(CNCCC1)CC(=O)O HIBJEGRTZANTFJ-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- OODAUJSHKGCQSF-UHFFFAOYSA-N 2-ethyl-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound O=C1N(CC)C(=O)CC11CCNCC1 OODAUJSHKGCQSF-UHFFFAOYSA-N 0.000 description 1
- CAHDYNYJWYSNKM-UHFFFAOYSA-N 2-ethyl-2,9-diazaspiro[4.5]decane-1,3-dione Chemical compound O=C1N(CC)C(=O)CC11CNCCC1 CAHDYNYJWYSNKM-UHFFFAOYSA-N 0.000 description 1
- NBQDGUQLQLNBOR-UHFFFAOYSA-N 2-ethyl-8-methyl-3-sulfanylidene-2,8-diazaspiro[4.5]decan-1-one Chemical compound C(C)N1C(C2(CC1=S)CCN(CC2)C)=O NBQDGUQLQLNBOR-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- IWWUYHVZGPWVDP-UHFFFAOYSA-N 3-oxodecanethial Chemical compound C(CC(CCCCCCC)=O)=S IWWUYHVZGPWVDP-UHFFFAOYSA-N 0.000 description 1
- GVGPQXVHNPFKSN-UHFFFAOYSA-N 3-sulfanylidenedecanethial Chemical compound C(CC(CCCCCCC)=S)=S GVGPQXVHNPFKSN-UHFFFAOYSA-N 0.000 description 1
- KRDCQZQJIOVAJY-UHFFFAOYSA-N 8-(cyclopropylmethyl)-2-ethyl-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound O=C1N(CC)C(=O)CC11CCN(CC2CC2)CC1 KRDCQZQJIOVAJY-UHFFFAOYSA-N 0.000 description 1
- JESJDYKIFCIOMN-UHFFFAOYSA-N 8-(cyclopropylmethyl)-2-ethyl-8-oxido-2-aza-8-azoniaspiro[4.5]decane-1,3-dione Chemical compound C(C)N1C(C2(CC1=O)CC[N+](CC2)(CC2CC2)[O-])=O JESJDYKIFCIOMN-UHFFFAOYSA-N 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 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 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
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- 210000004556 brain Anatomy 0.000 description 1
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
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- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VWQXCLBFGRMQJC-UHFFFAOYSA-N ethyl 3-oxopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCC(=O)C1 VWQXCLBFGRMQJC-UHFFFAOYSA-N 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 210000003715 limbic system Anatomy 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000008454 sleep-wake cycle Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH350383 | 1983-06-27 | ||
| CH350383 | 1983-06-27 | ||
| CH350483 | 1983-06-27 | ||
| CH350583 | 1983-06-27 | ||
| CH350483 | 1983-06-27 | ||
| CH350583 | 1983-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8401907A true NL8401907A (nl) | 1985-01-16 |
Family
ID=27174377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8401907A NL8401907A (nl) | 1983-06-27 | 1984-06-15 | Spirosuccinimiden en werkwijzen voor het bereiden en toepassen van deze spirosuccinimiden. |
Country Status (16)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3431195A1 (de) * | 1984-08-24 | 1986-03-06 | Troponwerke GmbH & Co KG, 5000 Köln | Neue benzodiazepine, verfahren zu ihrer herstellung sowie ihre verwendung |
| EP0273659A1 (en) * | 1986-12-27 | 1988-07-06 | Takeda Chemical Industries, Ltd. | Azaspiro compounds, their production and use |
| US5407938A (en) * | 1990-04-10 | 1995-04-18 | Israel Institute For Biological Research | Certain 1-methyl-piperidine-4-spiro-4'-(1'-3'-oxazolines) and corresponding -(1',3' thiazolines) |
| JP2800953B2 (ja) * | 1990-07-06 | 1998-09-21 | 住友製薬株式会社 | 新規なイミド誘導体 |
| BE1007765A5 (fr) | 1994-06-27 | 1995-10-17 | Blagden Ind Plc | Fut metallique a ouverture totale. |
| DE19715758C1 (de) * | 1997-04-16 | 1998-11-05 | Man B & W Diesel Gmbh | Kolben für eine Hubkolbenbrennkraftmaschine |
| WO1999032489A1 (en) * | 1997-12-23 | 1999-07-01 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| JP4749715B2 (ja) | 2002-07-05 | 2011-08-17 | ターガセプト，インコーポレイテッド | Ｎ−アリールジアザスピロ環式化合物、並びにその製造及び使用方法 |
| ATE521610T1 (de) * | 2003-09-10 | 2011-09-15 | Virochem Pharma Inc | Spiroverbindungen und -verfahren zur modulation von chemokin-rezeptor-aktivität |
| US9017724B2 (en) | 2004-02-24 | 2015-04-28 | The General Hospital Corporation | Catalytic radiofluorination |
| US8257680B1 (en) | 2004-02-24 | 2012-09-04 | The General Hospital Corporation | Catalytic radiofluorination |
| JO2676B1 (en) | 2004-04-06 | 2012-06-17 | جانسين فارماسوتيكا ان. في | Derivatives of second-aza-spiro- (5,4) -dikan and their use as antihistamines |
| MX2007011079A (es) | 2005-03-08 | 2007-10-08 | Janssen Pharmaceutica Nv | Derivados de diaza-espiro-[4-4]-nonano como antagonistas de la neurocinina (nk1). |
| EP2268647B1 (en) | 2008-03-21 | 2017-01-25 | The General Hospital Corporation | Compounds and compositions for the detection and treatment of alzheimer's disease and related disorders |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB936477A (en) * | 1959-03-25 | 1963-09-11 | Sandoz Ltd | Improvements in or relating to substituted succinimides |
| DE1211646B (de) * | 1959-03-25 | 1966-03-03 | Sandoz Ag | Verfahren zur Herstellung von Spirosuccinimiden und deren Salzen |
| US3198800A (en) * | 1964-05-07 | 1965-08-03 | Sandoz Ltd | 2, 8-(para-f-4-oxo-butyl)-diazaspiro[4, 5]-decane-1, 3-diones |
| BE897058A (fr) * | 1982-06-25 | 1983-12-16 | Sandoz Sa | Utilisation d'un derive du spiro-succinimide dans le traitement de la demence du type alzheimer |
-
1984
- 1984-06-15 NL NL8401907A patent/NL8401907A/nl not_active Application Discontinuation
- 1984-06-15 HU HU842326A patent/HUT36793A/hu unknown
- 1984-06-16 DE DE3422411A patent/DE3422411A1/de not_active Withdrawn
- 1984-06-18 WO PCT/CH1984/000099 patent/WO1985000171A1/de unknown
- 1984-06-22 FR FR8410017A patent/FR2549061A1/fr active Pending
- 1984-06-25 DK DK310184A patent/DK310184A/da not_active Application Discontinuation
- 1984-06-25 GR GR75100A patent/GR82274B/el unknown
- 1984-06-25 PT PT78787A patent/PT78787B/pt unknown
- 1984-06-25 SE SE8403376A patent/SE8403376L/xx not_active Application Discontinuation
- 1984-06-25 AU AU29833/84A patent/AU2983384A/en not_active Abandoned
- 1984-06-25 GB GB08416172A patent/GB2142332A/en not_active Withdrawn
- 1984-06-25 IL IL72218A patent/IL72218A0/xx unknown
- 1984-06-25 FI FI842547A patent/FI842547A7/fi not_active Application Discontinuation
- 1984-06-26 IT IT48458/84A patent/IT1199148B/it active
- 1984-06-26 ES ES533735A patent/ES8601202A1/es not_active Expired
- 1984-06-27 LU LU85434A patent/LU85434A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES533735A0 (es) | 1985-10-16 |
| IT8448458A0 (it) | 1984-06-26 |
| FI842547A7 (fi) | 1984-12-28 |
| HUT36793A (en) | 1985-10-28 |
| AU2983384A (en) | 1985-01-03 |
| LU85434A1 (fr) | 1985-03-26 |
| SE8403376L (sv) | 1984-12-28 |
| FI842547A0 (fi) | 1984-06-25 |
| DK310184D0 (da) | 1984-06-25 |
| PT78787A (en) | 1984-07-01 |
| GB8416172D0 (en) | 1984-08-01 |
| DK310184A (da) | 1984-12-28 |
| GR82274B (enrdf_load_stackoverflow) | 1984-12-13 |
| GB2142332A (en) | 1985-01-16 |
| ES8601202A1 (es) | 1985-10-16 |
| FR2549061A1 (fr) | 1985-01-18 |
| IL72218A0 (en) | 1984-10-31 |
| DE3422411A1 (de) | 1985-01-03 |
| PT78787B (en) | 1986-06-05 |
| IT1199148B (it) | 1988-12-30 |
| SE8403376D0 (sv) | 1984-06-25 |
| WO1985000171A1 (en) | 1985-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |