NO300211B1 - Heterosykliske karboksylsyrer, farmasöytiske preparater og anvendelse av karboksylsyrene til fremstilling av preparatene - Google Patents
Heterosykliske karboksylsyrer, farmasöytiske preparater og anvendelse av karboksylsyrene til fremstilling av preparatene Download PDFInfo
- Publication number
- NO300211B1 NO300211B1 NO934159A NO934159A NO300211B1 NO 300211 B1 NO300211 B1 NO 300211B1 NO 934159 A NO934159 A NO 934159A NO 934159 A NO934159 A NO 934159A NO 300211 B1 NO300211 B1 NO 300211B1
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- mixture
- ethoxy
- dihydro
- added
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- -1 Heterocyclic carboxylic acids Chemical class 0.000 title description 15
- 150000001735 carboxylic acids Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 208000012902 Nervous system disease Diseases 0.000 claims description 5
- 208000015114 central nervous system disease Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- AQTQDQNTSBTPHZ-HXUWFJFHSA-N (3R)-1-[2-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylmethylideneamino)oxyethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCON=CC1C2=CC=CC=C2CCC2=CC=CC=C21 AQTQDQNTSBTPHZ-HXUWFJFHSA-N 0.000 claims 1
- VQANFEQCHHCOAG-QGZVFWFLSA-N (3r)-1-[2-(2-phenothiazin-10-ylethoxy)ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCCN1C2=CC=CC=C2SC2=CC=CC=C21 VQANFEQCHHCOAG-QGZVFWFLSA-N 0.000 claims 1
- HVUBXVHCVWJVHW-QGZVFWFLSA-N (3r)-1-[2-(2-phenoxazin-10-ylethoxy)ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCCN1C2=CC=CC=C2OC2=CC=CC=C21 HVUBXVHCVWJVHW-QGZVFWFLSA-N 0.000 claims 1
- QAHRRKXCHVXIFM-LJQANCHMSA-N (3r)-1-[2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)oxyethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCON=C1C2=CC=CC=C2CCC2=CC=CC=C21 QAHRRKXCHVXIFM-LJQANCHMSA-N 0.000 claims 1
- YFGNKQZRTRUJTI-HXUWFJFHSA-N (3r)-1-[2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylidenemethoxy)ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOC=C1C2=CC=CC=C2CCC2=CC=CC=C21 YFGNKQZRTRUJTI-HXUWFJFHSA-N 0.000 claims 1
- FCQCCTYVNXSZCZ-JOCHJYFZSA-N (3r)-1-[2-[2-(11,12-dihydro-10h-benzo[b][1]benzazocin-5-yl)ethoxy]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCCN1C2=CC=CC=C2CCCC2=CC=CC=C21 FCQCCTYVNXSZCZ-JOCHJYFZSA-N 0.000 claims 1
- SFXNBCLCFHXQSF-LJQANCHMSA-N (3r)-1-[2-[2-(2,9-dichloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethoxy]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCCN1C2=CC(Cl)=CC=C2CCC2=CC=C(Cl)C=C21 SFXNBCLCFHXQSF-LJQANCHMSA-N 0.000 claims 1
- NPESLZCQHNYEEB-MRXNPFEDSA-N (3r)-1-[2-[2-(2-chlorophenothiazin-10-yl)ethoxy]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 NPESLZCQHNYEEB-MRXNPFEDSA-N 0.000 claims 1
- UIYNLGPDQIVGHU-LWMIZPGFSA-N (3r)-1-[2-[2-(5,6,11,12-tetrahydrobenzo[c][1]benzazocin-12-yl)ethoxy]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCCC1C2=CC=CC=C2NCC2=CC=CC=C2C1 UIYNLGPDQIVGHU-LWMIZPGFSA-N 0.000 claims 1
- UAYYDSSBLNAIGY-OAQYLSRUSA-N (3r)-1-[2-[2-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethoxy]ethyl]piperidine-3-carboxylic acid Chemical group C1[C@H](C(=O)O)CCCN1CCOCCN1C2=CC=CC=C2CCC2=CC=CC=C21 UAYYDSSBLNAIGY-OAQYLSRUSA-N 0.000 claims 1
- JAYKIOPDHWYQDF-OAQYLSRUSA-N (3r)-1-[2-[2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylidene)ethoxy]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCC=C1C2=CC=CC=C2CCC2=CC=CC=C21 JAYKIOPDHWYQDF-OAQYLSRUSA-N 0.000 claims 1
- TXSUTHVBHAHZCA-JOCHJYFZSA-N (3r)-1-[2-[2-(6,11-dihydrobenzo[c][1]benzazepin-5-yl)ethoxy]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCCN1C2=CC=CC=C2CC2=CC=CC=C2C1 TXSUTHVBHAHZCA-JOCHJYFZSA-N 0.000 claims 1
- AIHJCKMMAOEQKB-JOCHJYFZSA-N (3r)-1-[2-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propoxy]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCOCCCN1C2=CC=CC=C2CCC2=CC=CC=C21 AIHJCKMMAOEQKB-JOCHJYFZSA-N 0.000 claims 1
- NUXGFPYICWCXIY-JOCHJYFZSA-N (3r)-1-[3-[2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylidene)ethoxy]propyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCCOCC=C1C2=CC=CC=C2CCC2=CC=CC=C21 NUXGFPYICWCXIY-JOCHJYFZSA-N 0.000 claims 1
- ZANUBNKMSFQEMK-JOCHJYFZSA-N (3r)-1-[3-[2-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)ethoxy]propyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCCOCCC1C2=CC=CC=C2CCC2=CC=CC=C21 ZANUBNKMSFQEMK-JOCHJYFZSA-N 0.000 claims 1
- KXBLCVCXERBVLN-JOCHJYFZSA-N (3r)-1-[3-[2-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)ethoxy]propyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCCOCC=C1C2=CC=CC=C2C=CC2=CC=CC=C21 KXBLCVCXERBVLN-JOCHJYFZSA-N 0.000 claims 1
- DOIGDCYCEVVBBY-INIZCTEOSA-N (3s)-1-[2-[2-[2-(trifluoromethyl)phenothiazin-10-yl]ethoxy]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@@H](C(=O)O)CCCN1CCOCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 DOIGDCYCEVVBBY-INIZCTEOSA-N 0.000 claims 1
- TVWXYLJYXTXZQK-UHFFFAOYSA-N 1-[2-[2-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethoxy]ethyl]-3,6-dihydro-2h-pyridine-5-carboxylic acid Chemical compound C1C(C(=O)O)=CCCN1CCOCCN1C2=CC=CC=C2CCC2=CC=CC=C21 TVWXYLJYXTXZQK-UHFFFAOYSA-N 0.000 claims 1
- WOQUQXZPZUZTOR-UHFFFAOYSA-N 1-[2-[2-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)ethoxy]ethyl]-3,6-dihydro-2h-pyridine-5-carboxylic acid Chemical compound C1C(C(=O)O)=CCCN1CCOCCC1C2=CC=CC=C2CCC2=CC=CC=C21 WOQUQXZPZUZTOR-UHFFFAOYSA-N 0.000 claims 1
- PNTIDWVMMVQJKP-UHFFFAOYSA-N 2-[1-[2-[2-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethoxy]ethyl]pyrrolidin-3-yl]acetic acid Chemical compound C1C(CC(=O)O)CCN1CCOCCN1C2=CC=CC=C2CCC2=CC=CC=C21 PNTIDWVMMVQJKP-UHFFFAOYSA-N 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 168
- 239000000203 mixture Substances 0.000 description 151
- 239000000243 solution Substances 0.000 description 142
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 108
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 96
- 239000002904 solvent Substances 0.000 description 93
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
- 239000003921 oil Substances 0.000 description 71
- 235000019198 oils Nutrition 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
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- 239000012071 phase Substances 0.000 description 59
- 239000012074 organic phase Substances 0.000 description 57
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
- 239000007787 solid Substances 0.000 description 31
- 238000004809 thin layer chromatography Methods 0.000 description 31
- 229910004298 SiO 2 Inorganic materials 0.000 description 29
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- 238000010992 reflux Methods 0.000 description 27
- 229910052938 sodium sulfate Inorganic materials 0.000 description 27
- 235000011152 sodium sulphate Nutrition 0.000 description 27
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 26
- 235000019341 magnesium sulphate Nutrition 0.000 description 26
- 239000008346 aqueous phase Substances 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 21
- 239000003480 eluent Substances 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- 239000012299 nitrogen atmosphere Substances 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- 239000000284 extract Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
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- 238000003756 stirring Methods 0.000 description 10
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- HHPGQKZOPPDLNH-OGFXRTJISA-N 2,3-dihydroxybutanedioic acid;ethyl (3r)-piperidine-3-carboxylate Chemical compound OC(=O)C(O)C(O)C(O)=O.CCOC(=O)[C@@H]1CCCNC1 HHPGQKZOPPDLNH-OGFXRTJISA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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- 239000006260 foam Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
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- 230000002378 acidificating effect Effects 0.000 description 6
- XIWBSOUNZWSFKU-SSDOTTSWSA-N ethyl (3r)-piperidine-3-carboxylate Chemical compound CCOC(=O)[C@@H]1CCCNC1 XIWBSOUNZWSFKU-SSDOTTSWSA-N 0.000 description 6
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 5
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- 230000005764 inhibitory process Effects 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- 239000012312 sodium hydride Substances 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- TXQKSMSLZVKQBI-UHFFFAOYSA-N 1-(4,4-diphenylbut-3-enyl)-3-piperidinecarboxylic acid Chemical compound C1C(C(=O)O)CCCN1CCC=C(C=1C=CC=CC=1)C1=CC=CC=C1 TXQKSMSLZVKQBI-UHFFFAOYSA-N 0.000 description 2
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- FRDUWSVJBKDUIM-UHFFFAOYSA-N 10-[2-[2-(oxan-2-yloxy)ethoxy]ethyl]phenothiazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CCOCCOC1CCCCO1 FRDUWSVJBKDUIM-UHFFFAOYSA-N 0.000 description 2
- BODGXGJKTSVHAL-UHFFFAOYSA-N 11-(2-bromoethoxymethylidene)-5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulene Chemical compound C1CC2=CC=CC=C2C(=COCCBr)C2=CC=CC=C21 BODGXGJKTSVHAL-UHFFFAOYSA-N 0.000 description 2
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- 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
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid group Chemical group C(\C=C/C(=O)O)(=O)O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GUUZKGTZIQDLQO-UHFFFAOYSA-N methyl 2-[1-[2-[2-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethoxy]ethyl]pyrrolidin-3-yl]acetate Chemical compound C1C(CC(=O)OC)CCN1CCOCCN1C2=CC=CC=C2CCC2=CC=CC=C21 GUUZKGTZIQDLQO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 210000000063 presynaptic terminal Anatomy 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 238000005406 washing Methods 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/20—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
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK91937A DK93791D0 (da) | 1991-05-17 | 1991-05-17 | Nye heterocykliske carboxylsyrer |
| PCT/DK1992/000155 WO1992020658A1 (en) | 1991-05-17 | 1992-05-14 | Novel heterocyclic carboxylic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO934159L NO934159L (no) | 1993-11-17 |
| NO934159D0 NO934159D0 (no) | 1993-11-17 |
| NO300211B1 true NO300211B1 (no) | 1997-04-28 |
Family
ID=8099201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO934159A NO300211B1 (no) | 1991-05-17 | 1993-11-17 | Heterosykliske karboksylsyrer, farmasöytiske preparater og anvendelse av karboksylsyrene til fremstilling av preparatene |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5348965A (ja) |
| EP (1) | EP0585314B1 (ja) |
| JP (1) | JPH06507616A (ja) |
| AT (1) | ATE143009T1 (ja) |
| AU (1) | AU665761B2 (ja) |
| CA (1) | CA2102811A1 (ja) |
| DE (1) | DE69213935T2 (ja) |
| DK (2) | DK93791D0 (ja) |
| ES (1) | ES2094357T3 (ja) |
| FI (1) | FI103116B1 (ja) |
| GR (1) | GR3021822T3 (ja) |
| IL (1) | IL101887A (ja) |
| NO (1) | NO300211B1 (ja) |
| NZ (1) | NZ242759A (ja) |
| WO (1) | WO1992020658A1 (ja) |
| ZA (1) | ZA923556B (ja) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK74493D0 (da) * | 1993-06-23 | 1993-06-23 | Novo Nordisk As | Novel heterocyclic chemistry |
| DK74393D0 (da) * | 1993-06-23 | 1993-06-23 | Novo Nordisk As | Novel heterocyclic chemistry |
| DK74693D0 (da) * | 1993-06-23 | 1993-06-23 | Novo Nordisk As | Novel heterocyclic chemistry |
| IL112223A0 (en) * | 1994-01-04 | 1995-03-30 | Novo Nordisk As | Pharmaceutical compositions for the treatment of neurological inflammatory conditions |
| US5698551A (en) * | 1995-04-07 | 1997-12-16 | Novo Nordisk A/S | Heterocyclic compounds |
| US5962449A (en) | 1995-04-07 | 1999-10-05 | Novo Nordisk A/S | Tricyclic compounds in treating hyperalgesic conditions and NIDDM |
| WO1997022342A1 (en) * | 1995-12-15 | 1997-06-26 | Novo Nordisk A/S | Novel method |
| WO1999000376A1 (en) * | 1997-06-25 | 1999-01-07 | Novo Nordisk A/S | Novel heterocyclic compounds |
| IE970588A1 (en) | 1997-08-01 | 2000-08-23 | Elan Corp Plc | Controlled release pharmaceutical compositions containing tiagabine |
| US6468996B1 (en) * | 1998-10-21 | 2002-10-22 | Novo Nordisk A/S | Substituted hetero-polycyclic compounds as PPARα and PPARγ activators |
| CN1382441A (zh) * | 2002-05-21 | 2002-12-04 | 中国科学院上海生命科学研究院 | γ－氨基丁酸转运蛋白抑制剂在制备镇痛药物中的应用 |
| US7417040B2 (en) * | 2004-03-01 | 2008-08-26 | Bristol-Myers Squibb Company | Fused tricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3 |
| US7378426B2 (en) * | 2004-03-01 | 2008-05-27 | Bristol-Myers Squibb Company | Fused heterotricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL99690C (ja) * | 1956-11-15 | |||
| BE560750A (ja) * | 1957-07-26 | |||
| CH368178A (de) * | 1958-09-10 | 1963-03-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen basisch substituierten heterocyclischen Verbindungen |
| DK704488D0 (da) * | 1988-12-19 | 1988-12-19 | Novo Industri As | Nye n-substituerede azaheterocykliske carboxylsyrer |
| US4910312A (en) * | 1985-11-08 | 1990-03-20 | Warner-Lambert Company | Various N-substituted 3-piperidine carboxylic acids or N-substituted 3-pyridinecarboxylic acids and derivatives thereof |
| FI864246A (fi) * | 1985-11-08 | 1987-05-09 | Warner Lambert Co | N-substituerade 3-piperidin- eller 3-pyridinkarboxylsyror samt deras derivat. |
| DK270488D0 (da) * | 1988-05-18 | 1988-05-18 | Novo Industri As | Hidtil ukendte o-substituerede ketoximer |
-
1991
- 1991-05-17 DK DK91937A patent/DK93791D0/da not_active Application Discontinuation
-
1992
- 1992-05-14 AT AT92910899T patent/ATE143009T1/de not_active IP Right Cessation
- 1992-05-14 DK DK92910899.1T patent/DK0585314T3/da active
- 1992-05-14 US US07/882,788 patent/US5348965A/en not_active Expired - Fee Related
- 1992-05-14 WO PCT/DK1992/000155 patent/WO1992020658A1/en active IP Right Grant
- 1992-05-14 ES ES92910899T patent/ES2094357T3/es not_active Expired - Lifetime
- 1992-05-14 JP JP4509775A patent/JPH06507616A/ja active Pending
- 1992-05-14 CA CA2102811A patent/CA2102811A1/en not_active Abandoned
- 1992-05-14 AU AU17837/92A patent/AU665761B2/en not_active Ceased
- 1992-05-14 EP EP92910899A patent/EP0585314B1/en not_active Expired - Lifetime
- 1992-05-14 DE DE69213935T patent/DE69213935T2/de not_active Expired - Fee Related
- 1992-05-15 ZA ZA923556A patent/ZA923556B/xx unknown
- 1992-05-15 IL IL10188792A patent/IL101887A/en not_active IP Right Cessation
- 1992-05-15 NZ NZ242759A patent/NZ242759A/en unknown
-
1993
- 1993-11-16 FI FI935064A patent/FI103116B1/fi active
- 1993-11-17 NO NO934159A patent/NO300211B1/no not_active IP Right Cessation
-
1996
- 1996-11-28 GR GR960403213T patent/GR3021822T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2094357T3 (es) | 1997-01-16 |
| WO1992020658A1 (en) | 1992-11-26 |
| ATE143009T1 (de) | 1996-10-15 |
| JPH06507616A (ja) | 1994-09-01 |
| FI935064A (fi) | 1993-11-16 |
| DE69213935D1 (en) | 1996-10-24 |
| US5348965A (en) | 1994-09-20 |
| NZ242759A (en) | 1995-03-28 |
| AU665761B2 (en) | 1996-01-18 |
| IL101887A0 (en) | 1992-12-30 |
| FI103116B (fi) | 1999-04-30 |
| IL101887A (en) | 1996-10-16 |
| EP0585314B1 (en) | 1996-09-18 |
| NO934159L (no) | 1993-11-17 |
| ZA923556B (en) | 1993-01-27 |
| NO934159D0 (no) | 1993-11-17 |
| FI935064A0 (fi) | 1993-11-16 |
| DE69213935T2 (de) | 1997-03-27 |
| DK0585314T3 (ja) | 1997-05-05 |
| FI103116B1 (fi) | 1999-04-30 |
| GR3021822T3 (en) | 1997-02-28 |
| EP0585314A1 (en) | 1994-03-09 |
| DK93791D0 (da) | 1991-05-17 |
| AU1783792A (en) | 1992-12-30 |
| CA2102811A1 (en) | 1992-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN NOVEMBER 2000 |