NL8601763A - Psychogeriatrische diazinylpiperidinederivaten van cyclische amiden en imiden. - Google Patents
Psychogeriatrische diazinylpiperidinederivaten van cyclische amiden en imiden. Download PDFInfo
- Publication number
- NL8601763A NL8601763A NL8601763A NL8601763A NL8601763A NL 8601763 A NL8601763 A NL 8601763A NL 8601763 A NL8601763 A NL 8601763A NL 8601763 A NL8601763 A NL 8601763A NL 8601763 A NL8601763 A NL 8601763A
- Authority
- NL
- Netherlands
- Prior art keywords
- compound
- methyl
- pyrrolidinone
- piperidinyl
- pyrimidinyl
- Prior art date
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- 150000003950 cyclic amides Chemical class 0.000 title claims description 9
- 150000003949 imides Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 108
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- -1 2-chloro-4-pyrimidinyl Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052752 metalloid Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- BRBGYELIWTUMJL-UHFFFAOYSA-N 1-[[1-(2-chloro-6-methylpyrimidin-4-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound ClC1=NC(C)=CC(N2CCC(CN3C(CCC3)=O)CC2)=N1 BRBGYELIWTUMJL-UHFFFAOYSA-N 0.000 claims 1
- WZRWFDQLLRKMRS-UHFFFAOYSA-N 1-[[1-(4-chloro-6-methylpyrimidin-2-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound CC1=CC(Cl)=NC(N2CCC(CN3C(CCC3)=O)CC2)=N1 WZRWFDQLLRKMRS-UHFFFAOYSA-N 0.000 claims 1
- JAGAFYRCPMXOJP-UHFFFAOYSA-N 1-[[1-(4-chloropyrimidin-2-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound ClC1=CC=NC(N2CCC(CN3C(CCC3)=O)CC2)=N1 JAGAFYRCPMXOJP-UHFFFAOYSA-N 0.000 claims 1
- NSGZNMOCHFCWDH-UHFFFAOYSA-N 1-[[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound N1=CC(Cl)=CN=C1N1CCC(CN2C(CCC2)=O)CC1 NSGZNMOCHFCWDH-UHFFFAOYSA-N 0.000 claims 1
- FXWJYWSKTOGXJN-UHFFFAOYSA-N 1-[[1-(5-iodopyrimidin-2-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound N1=CC(I)=CN=C1N1CCC(CN2C(CCC2)=O)CC1 FXWJYWSKTOGXJN-UHFFFAOYSA-N 0.000 claims 1
- SKHXZTDMPYXSKU-UHFFFAOYSA-N 1-[[1-[2,6-bis(trifluoromethyl)pyrimidin-4-yl]piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound FC(C1=NC(=CC(=N1)N1CCC(CC1)CN1C(CCC1)=O)C(F)(F)F)(F)F SKHXZTDMPYXSKU-UHFFFAOYSA-N 0.000 claims 1
- QATHZPJMLYIHSZ-UHFFFAOYSA-N 1-[[1-[5-chloro-2-(trifluoromethyl)pyrimidin-4-yl]piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C1=NC=C(Cl)C(N2CCC(CN3C(CCC3)=O)CC2)=N1 QATHZPJMLYIHSZ-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 150000004040 pyrrolidinones Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 230000035939 shock Effects 0.000 description 17
- 238000007920 subcutaneous administration Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 208000000044 Amnesia Diseases 0.000 description 15
- 208000031091 Amnestic disease Diseases 0.000 description 15
- 230000006986 amnesia Effects 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 description 12
- 230000014759 maintenance of location Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000000460 chlorine Chemical group 0.000 description 7
- 125000003386 piperidinyl group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
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- 125000002947 alkylene group Chemical group 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- ZUNGTEUNVMHDIX-UHFFFAOYSA-N (1-pyrimidin-2-ylpiperidin-4-yl)methanol Chemical compound C1CC(CO)CCN1C1=NC=CC=N1 ZUNGTEUNVMHDIX-UHFFFAOYSA-N 0.000 description 5
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- 239000000843 powder Substances 0.000 description 4
- 229960003389 pramiracetam Drugs 0.000 description 4
- ZULJGOSFKWFVRX-UHFFFAOYSA-N pramiracetam Chemical compound CC(C)N(C(C)C)CCNC(=O)CN1CCCC1=O ZULJGOSFKWFVRX-UHFFFAOYSA-N 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 206010027374 Mental impairment Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- DDSZWBCJXDRQDU-UHFFFAOYSA-N [N].C1CCNCC1 Chemical group [N].C1CCNCC1 DDSZWBCJXDRQDU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- 238000005804 alkylation reaction Methods 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
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- 238000003556 assay Methods 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
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- 229910052801 chlorine Chemical group 0.000 description 1
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- 208000010877 cognitive disease Diseases 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
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- 238000010586 diagram Methods 0.000 description 1
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- 239000007884 disintegrant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 238000002635 electroconvulsive therapy Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 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
- 230000008570 general process Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 230000006993 memory improvement Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229960001227 oxiracetam Drugs 0.000 description 1
- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000011426 transformation method Methods 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
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75300685A | 1985-07-08 | 1985-07-08 | |
| US75300685 | 1985-07-08 | ||
| US86846886A | 1986-05-30 | 1986-05-30 | |
| US86846886 | 1986-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8601763A true NL8601763A (nl) | 1987-02-02 |
Family
ID=27115677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8601763A NL8601763A (nl) | 1985-07-08 | 1986-07-07 | Psychogeriatrische diazinylpiperidinederivaten van cyclische amiden en imiden. |
Country Status (28)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2634208B1 (fr) * | 1988-07-12 | 1990-11-23 | Synthelabo | Derives de ((piperidinyl-4)methyl)-2 dihydro-2,3 1h-isoindole, leur preparation et leur application en therapeutique |
| EP0351283A1 (fr) * | 1988-07-12 | 1990-01-17 | Synthelabo | Dérivés de [(pipéridinyl-4) méthyl]-2 dihydro-2,3 1H-isoindole et tétrahydro-2,3,4,5 1H-benzazépines, leur préparation et leur application en thérapeutique |
| US5356906A (en) * | 1989-10-27 | 1994-10-18 | The Du Pont Merck Pharmaceutical Company | (N-phthalimidoalkyl) piperidines useful as treatments for psychosis |
| HU206878B (en) * | 1989-10-27 | 1993-01-28 | Bristol Myers Squibb Co | Process for producing 1-//1-/2-/trifluoromethyl/-4-pyrimidinyl/-4-piperidinyl/-methyl/-2-pirrolidinone |
| CA2069318A1 (en) * | 1989-10-27 | 1991-04-28 | Engelbert Ciganek | (n-phthalimidoalkyl) piperidines |
| US5098904A (en) * | 1990-06-27 | 1992-03-24 | Bristol-Myers Squibb Company | Cerebral function enhancing pyrimidinyl derivatives |
| US5190951A (en) * | 1990-10-19 | 1993-03-02 | Ss Pharmaceutical Co., Ltd. | Quinoline derivatives |
| US5240934A (en) * | 1990-10-19 | 1993-08-31 | Ss Pharmaceutical Co., Ltd. | Quinoline derivatives |
| US5401744A (en) * | 1993-10-04 | 1995-03-28 | Bristol-Myers Squibb Company | Useful hemi-hydrate form of a cerebral function enhancing agent |
| CN106188039B (zh) * | 2016-06-30 | 2019-01-01 | 广东工业大学 | 一种二酮衍生物及其制备方法与应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE759371A (fr) * | 1969-11-24 | 1971-05-24 | Bristol Myers Co | Azaspirodecanediones heterocycliques et procedes pour leur preparation |
| ZA76475B (en) * | 1975-03-10 | 1977-08-31 | Ciba Geigy Ag | Indolyalkylpiperidines |
| EP0009465A1 (de) * | 1978-09-20 | 1980-04-02 | Ciba-Geigy Ag | N-(1-(4-Amino-2-chinazolinyl)-3- oder -4-piperidyl-lactame, Verfahren zu ihrer Herstellung, sowie pharmazeutische Präparate enthaltend diese Verbindungen |
| US4423049A (en) * | 1981-12-28 | 1983-12-27 | Mead Johnson & Company | 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyrimidines |
| US4524206A (en) * | 1983-09-12 | 1985-06-18 | Mead Johnson & Company | 1-Heteroaryl-4-(2,5-pyrrolidinedion-1-yl)alkyl)piperazine derivatives |
-
1986
- 1986-07-01 NZ NZ216720A patent/NZ216720A/xx unknown
- 1986-07-03 YU YU1186/86A patent/YU45017B/xx unknown
- 1986-07-03 FR FR8609666A patent/FR2584408B1/fr not_active Expired
- 1986-07-03 FI FI862830A patent/FI88300C/fi not_active IP Right Cessation
- 1986-07-07 BE BE0/216887A patent/BE905061A/fr not_active IP Right Cessation
- 1986-07-07 GR GR861765A patent/GR861765B/el unknown
- 1986-07-07 CH CH2740/86A patent/CH671579A5/de not_active IP Right Cessation
- 1986-07-07 IE IE182686A patent/IE59424B1/en not_active IP Right Cessation
- 1986-07-07 HU HU862835A patent/HU199455B/hu unknown
- 1986-07-07 NL NL8601763A patent/NL8601763A/nl active Search and Examination
- 1986-07-07 DK DK323986A patent/DK170441B1/da not_active IP Right Cessation
- 1986-07-07 AU AU59787/86A patent/AU595215B2/en not_active Expired
- 1986-07-07 NO NO862729A patent/NO167389C/no not_active IP Right Cessation
- 1986-07-07 GB GB8616504A patent/GB2177692B/en not_active Expired
- 1986-07-07 IT IT21049/86A patent/IT1196467B/it active
- 1986-07-07 CA CA000513196A patent/CA1272725A/en not_active Expired - Lifetime
- 1986-07-07 SE SE8603026A patent/SE462491B/sv not_active IP Right Cessation
- 1986-07-07 IL IL79351A patent/IL79351A/xx not_active IP Right Cessation
- 1986-07-08 DE DE3622842A patent/DE3622842C2/de not_active Expired - Lifetime
- 1986-07-08 CN CN86104681A patent/CN1012364B/zh not_active Expired
- 1986-07-08 PT PT82942A patent/PT82942B/pt unknown
- 1986-07-08 EG EG416/86A patent/EG18310A/xx active
- 1986-07-08 ES ES8600190A patent/ES2000476A6/es not_active Expired
- 1986-07-08 KR KR1019860005480A patent/KR940003756B1/ko not_active Expired - Fee Related
- 1986-07-08 AT AT0185286A patent/AT395850B/de not_active IP Right Cessation
-
1987
- 1987-06-10 YU YU1073/87A patent/YU44947B/xx unknown
-
1991
- 1991-12-31 SG SG1110/91A patent/SG111091G/en unknown
-
1992
- 1992-02-13 HK HK112/92A patent/HK11292A/xx not_active IP Right Cessation
- 1992-07-10 CY CY1630A patent/CY1630A/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DNT | Communications of changes of names of applicants whose applications have been laid open to public inspection |
Free format text: BRISTOL-MYERS SQUIBB COMPANY |
|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BN | A decision not to publish the application has become irrevocable |