NO760329L - - Google Patents
Info
- Publication number
- NO760329L NO760329L NO760329*[A NO760329A NO760329L NO 760329 L NO760329 L NO 760329L NO 760329 A NO760329 A NO 760329A NO 760329 L NO760329 L NO 760329L
- Authority
- NO
- Norway
- Prior art keywords
- triazolo
- thiadiazine
- dihydro
- ethyl
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 43
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- KLVQAIJZDCCJRZ-UHFFFAOYSA-N 2h-1,3,4-thiadiazine Chemical compound C1SC=CN=N1 KLVQAIJZDCCJRZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003852 triazoles Chemical class 0.000 claims description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- -1 methylene radicals Chemical class 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 7
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 7
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 7
- 229960003147 reserpine Drugs 0.000 description 7
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UXVCSPSWUNMPMT-UHFFFAOYSA-N 2-bromo-2,3-dihydroinden-1-one Chemical class C1=CC=C2C(=O)C(Br)CC2=C1 UXVCSPSWUNMPMT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 238000009472 formulation Methods 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
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000006188 syrup Substances 0.000 description 6
- 235000020357 syrup Nutrition 0.000 description 6
- AYNCWMIFKFADCZ-UHFFFAOYSA-N 2-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical class C1=CC=C2C(=O)C(Br)CCC2=C1 AYNCWMIFKFADCZ-UHFFFAOYSA-N 0.000 description 5
- 208000009132 Catalepsy Diseases 0.000 description 5
- 206010047853 Waxy flexibility Diseases 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000007903 gelatin capsule Substances 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000006735 deficit Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NSPWDODUFKPVMO-UHFFFAOYSA-N 2-bromo-5,6-dimethoxy-2,3-dihydroinden-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)C(Br)C2 NSPWDODUFKPVMO-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 206010033799 Paralysis Diseases 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- PELQCSAKKLXVLQ-UHFFFAOYSA-N 2-bromo-4-methyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(C)CC(Br)C(=O)C2=C1 PELQCSAKKLXVLQ-UHFFFAOYSA-N 0.000 description 2
- YYCUBXRVXPVFPC-UHFFFAOYSA-N 2-iodo-2,3-dihydroinden-1-one Chemical class C1=CC=C2C(=O)C(I)CC2=C1 YYCUBXRVXPVFPC-UHFFFAOYSA-N 0.000 description 2
- MHOFMGWBCRJNRX-UHFFFAOYSA-N 2-iodo-3,4-dihydro-2h-naphthalen-1-one Chemical class C1=CC=C2C(=O)C(I)CCC2=C1 MHOFMGWBCRJNRX-UHFFFAOYSA-N 0.000 description 2
- DLLBXBCKFUPBJE-UHFFFAOYSA-N 4-amino-1h-1,2,4-triazole-5-thione Chemical compound NN1C=NNC1=S DLLBXBCKFUPBJE-UHFFFAOYSA-N 0.000 description 2
- NHJQUZUFQOQBNE-UHFFFAOYSA-N 4-amino-3-ethyl-1h-1,2,4-triazole-5-thione Chemical compound CCC1=NNC(=S)N1N NHJQUZUFQOQBNE-UHFFFAOYSA-N 0.000 description 2
- SRLHDEROUKFEMJ-UHFFFAOYSA-N 4-methyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(C)CCC(=O)C2=C1 SRLHDEROUKFEMJ-UHFFFAOYSA-N 0.000 description 2
- IHMQOBPGHZFGLC-UHFFFAOYSA-N 5,6-dimethoxy-2,3-dihydroinden-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)CC2 IHMQOBPGHZFGLC-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 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 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 206010044565 Tremor Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000003001 depressive effect Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003176 neuroleptic agent Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- MACMNSLOLFMQKL-UHFFFAOYSA-N 1-sulfanyltriazole Chemical class SN1C=CN=N1 MACMNSLOLFMQKL-UHFFFAOYSA-N 0.000 description 1
- HMKKAPQUSMRHTR-UHFFFAOYSA-N 14-ethyl-4,5-dimethoxy-10-thia-12,13,15,16-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2,4,6,11,13-hexaene Chemical compound COC1=C(OC)C=C2C3=NN4C(CC)=NN=C4SC3CC2=C1 HMKKAPQUSMRHTR-UHFFFAOYSA-N 0.000 description 1
- AWADDHWPMYXYES-UHFFFAOYSA-N 14-tert-butyl-4,5-dimethyl-10-thia-12,13,15,16-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,11,13-hexaene Chemical compound C1C2SC3=NN=C(C(C)(C)C)N3N=C2C2=C1C=C(C)C(C)=C2 AWADDHWPMYXYES-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- LQVTVZWTYPASEL-UHFFFAOYSA-N 2-bromo-3-butyl-5-methyl-2,3-dihydroinden-1-one Chemical compound C1=C(C)C=C2C(CCCC)C(Br)C(=O)C2=C1 LQVTVZWTYPASEL-UHFFFAOYSA-N 0.000 description 1
- UXTBMFYJXJNPCZ-UHFFFAOYSA-N 2-bromo-3-ethyl-6-propoxy-2,3-dihydroinden-1-one Chemical compound CCCOC1=CC=C2C(CC)C(Br)C(=O)C2=C1 UXTBMFYJXJNPCZ-UHFFFAOYSA-N 0.000 description 1
- HSGMTQVILQESDP-UHFFFAOYSA-N 2-bromo-4,5,6,7-tetramethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound CC1=C(C)C(C)=C2C(C)CC(Br)C(=O)C2=C1 HSGMTQVILQESDP-UHFFFAOYSA-N 0.000 description 1
- JVKLTBQDKVXAGA-UHFFFAOYSA-N 2-bromo-4,5,6-triethyl-2,3-dihydroinden-1-one Chemical compound CCC1=C(CC)C(CC)=CC2=C1CC(Br)C2=O JVKLTBQDKVXAGA-UHFFFAOYSA-N 0.000 description 1
- XQBFUGFFYRKZIY-UHFFFAOYSA-N 2-bromo-4,7-diethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound CCC1=CC=C2C(CC)CC(Br)C(=O)C2=C1 XQBFUGFFYRKZIY-UHFFFAOYSA-N 0.000 description 1
- FRPRSBPWLJJFBC-UHFFFAOYSA-N 2-bromo-4-methyl-2,3-dihydroinden-1-one Chemical compound CC1=CC=CC2=C1CC(Br)C2=O FRPRSBPWLJJFBC-UHFFFAOYSA-N 0.000 description 1
- VKFDDZFJNCXFBI-UHFFFAOYSA-N 2-bromo-5,6-dibutoxy-2,3-dihydroinden-1-one Chemical compound C1=C(OCCCC)C(OCCCC)=CC2=C1C(=O)C(Br)C2 VKFDDZFJNCXFBI-UHFFFAOYSA-N 0.000 description 1
- FWBOQGUOFMOFNJ-UHFFFAOYSA-N 2-bromo-5-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C(Br)CCC2=C1C=CC=C2OC FWBOQGUOFMOFNJ-UHFFFAOYSA-N 0.000 description 1
- SIEYRIMVCZCULR-UHFFFAOYSA-N 2-bromo-5-methyl-4-propyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC(C)=C2C(CCC)CC(Br)C(=O)C2=C1 SIEYRIMVCZCULR-UHFFFAOYSA-N 0.000 description 1
- LPIUDXOQYBQZDR-UHFFFAOYSA-N 2-bromo-5-propan-2-yl-2,3-dihydroinden-1-one Chemical compound CC(C)C1=CC=C2C(=O)C(Br)CC2=C1 LPIUDXOQYBQZDR-UHFFFAOYSA-N 0.000 description 1
- KIUBAMHSEVAGPP-UHFFFAOYSA-N 2-bromo-6,7-diethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC(Br)C(=O)C2=C1C=C(CC)C(CC)=C2 KIUBAMHSEVAGPP-UHFFFAOYSA-N 0.000 description 1
- NAXVBXDTOCUKNH-UHFFFAOYSA-N 2-bromo-6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C(Br)CCC2=CC(OC)=CC=C21 NAXVBXDTOCUKNH-UHFFFAOYSA-N 0.000 description 1
- PXBWAMRUHSEYCI-UHFFFAOYSA-N 2-bromo-6-tert-butyl-4-ethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(C(C)(C)C)C=C2C(CC)CC(Br)C(=O)C2=C1 PXBWAMRUHSEYCI-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- XDBKPTOOJLUTRK-UHFFFAOYSA-N 3-ethyl-10,10a-dihydroindeno[1,2-e]-s-triazolo[3,4-b][1,3,4]thiadiazine Chemical compound C1=CC=C2C3=NN4C(CC)=NN=C4SC3CC2=C1 XDBKPTOOJLUTRK-UHFFFAOYSA-N 0.000 description 1
- XMBWTDZXDDFTSX-UHFFFAOYSA-N 3-ethyl-6-propoxy-2,3-dihydroinden-1-one Chemical compound CCCOC1=CC=C2C(CC)CC(=O)C2=C1 XMBWTDZXDDFTSX-UHFFFAOYSA-N 0.000 description 1
- HJJCVPALCWUMKM-UHFFFAOYSA-N 4,14-dimethyl-10-thia-12,13,15,16-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,11,13-hexaene Chemical compound C1=C(C)C=C2C3=NN4C(C)=NN=C4SC3CC2=C1 HJJCVPALCWUMKM-UHFFFAOYSA-N 0.000 description 1
- VQDBZGKXIDXUJZ-UHFFFAOYSA-N 4,5,6,14-tetraethyl-10-thia-12,13,15,16-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,11,13-hexaene Chemical compound C12=NN3C(CC)=NN=C3SC2CC2=C1C=C(CC)C(CC)=C2CC VQDBZGKXIDXUJZ-UHFFFAOYSA-N 0.000 description 1
- VLLQJGLFMCFZHS-UHFFFAOYSA-N 4,5,6,7-tetramethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound CC1=C(C)C(C)=C2C(C)CCC(=O)C2=C1 VLLQJGLFMCFZHS-UHFFFAOYSA-N 0.000 description 1
- XZQZPOFTBMXVDC-UHFFFAOYSA-N 4,5,6-triethyl-14-propan-2-yl-10-thia-12,13,15,16-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,11,13-hexaene Chemical compound C12=NN(C(=NN=3)C(C)C)C=3SC2CC2=C1C=C(CC)C(CC)=C2CC XZQZPOFTBMXVDC-UHFFFAOYSA-N 0.000 description 1
- YXDVKKQDWXLJBX-UHFFFAOYSA-N 4,5,6-triethyl-2,3-dihydroinden-1-one Chemical compound CCC1=C(CC)C(CC)=CC2=C1CCC2=O YXDVKKQDWXLJBX-UHFFFAOYSA-N 0.000 description 1
- WVTPBLSSZNEXKC-UHFFFAOYSA-N 4,7-diethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound CCC1=CC=C2C(CC)CCC(=O)C2=C1 WVTPBLSSZNEXKC-UHFFFAOYSA-N 0.000 description 1
- NTUKJYMPIKZIAC-UHFFFAOYSA-N 4,8-dimethyl-14-(2-methylpropyl)-10-thia-12,13,15,16-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,11,13-hexaene Chemical compound C1=C(C)C=C2C3=NN4C(CC(C)C)=NN=C4SC3C(C)C2=C1 NTUKJYMPIKZIAC-UHFFFAOYSA-N 0.000 description 1
- VMECUCZJLBBLIY-UHFFFAOYSA-N 4-amino-3-(2-methylpropyl)-1h-1,2,4-triazole-5-thione Chemical compound CC(C)CC1=NNC(=S)N1N VMECUCZJLBBLIY-UHFFFAOYSA-N 0.000 description 1
- KBKNKJFPVHUXCW-UHFFFAOYSA-N 4-amino-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1N KBKNKJFPVHUXCW-UHFFFAOYSA-N 0.000 description 1
- UKHPTMIZKBTYKD-UHFFFAOYSA-N 4-amino-3-propan-2-yl-1h-1,2,4-triazole-5-thione Chemical compound CC(C)C1=NNC(=S)N1N UKHPTMIZKBTYKD-UHFFFAOYSA-N 0.000 description 1
- ROAXVRKEIASZAE-UHFFFAOYSA-N 4-amino-3-propyl-1h-1,2,4-triazole-5-thione Chemical compound CCCC1=NNC(=S)N1N ROAXVRKEIASZAE-UHFFFAOYSA-N 0.000 description 1
- BMVRIMOCVZOKME-UHFFFAOYSA-N 4-amino-3-tert-butyl-1h-1,2,4-triazole-5-thione Chemical compound CC(C)(C)C1=NNC(=S)N1N BMVRIMOCVZOKME-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- RUORWXQKVXTQJJ-UHFFFAOYSA-N 4-methyl-2,3-dihydroinden-1-one Chemical compound CC1=CC=CC2=C1CCC2=O RUORWXQKVXTQJJ-UHFFFAOYSA-N 0.000 description 1
- IDXCJZORBMVWFS-UHFFFAOYSA-N 5,6-dibutoxy-2,3-dihydroinden-1-one Chemical compound C1=C(OCCCC)C(OCCCC)=CC2=C1C(=O)CC2 IDXCJZORBMVWFS-UHFFFAOYSA-N 0.000 description 1
- GJDKUQZAYQMKHH-UHFFFAOYSA-N 5,8,14-trimethyl-10-thia-12,13,15,16-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,11,13-hexaene Chemical compound C12=CC=C(C)C=C2C(C)C2C1=NN1C(C)=NN=C1S2 GJDKUQZAYQMKHH-UHFFFAOYSA-N 0.000 description 1
- FSHJKEQFTLNPDT-UHFFFAOYSA-N 5-propan-2-yl-2,3-dihydroinden-1-one Chemical compound CC(C)C1=CC=C2C(=O)CCC2=C1 FSHJKEQFTLNPDT-UHFFFAOYSA-N 0.000 description 1
- ANJGWLAGNBINHQ-UHFFFAOYSA-N 6,7-diethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=C1C=C(CC)C(CC)=C2 ANJGWLAGNBINHQ-UHFFFAOYSA-N 0.000 description 1
- SZXRDZAELPHXBP-UHFFFAOYSA-N 6-tert-butyl-4-ethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(C(C)(C)C)C=C2C(CC)CCC(=O)C2=C1 SZXRDZAELPHXBP-UHFFFAOYSA-N 0.000 description 1
- FTTPUMZADACVGJ-UHFFFAOYSA-N 7-propan-2-yl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(C(C)C)=CC=C21 FTTPUMZADACVGJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001539473 Euphoria Species 0.000 description 1
- 206010015535 Euphoric mood Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000699694 Gerbillinae Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 206010027951 Mood swings Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010052904 Musculoskeletal stiffness Diseases 0.000 description 1
- 241000282339 Mustela Species 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical group C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- VDIHFNQRHGYISG-UHFFFAOYSA-N cyclopentylbenzene Chemical group C1CCCC1C1=CC=CC=C1 VDIHFNQRHGYISG-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 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
- 239000003292 glue Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004630 mental health Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 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
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003236 psychic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- DZCJZBPBJLJJCT-UHFFFAOYSA-N triazolo[4,5-e]thiadiazine Chemical group N1=NSC2=NN=NC2=C1 DZCJZBPBJLJJCT-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/571,941 US3954983A (en) | 1975-04-28 | 1975-04-28 | Triazolobenzocycloalkylthiadiazine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO760329L true NO760329L (de) | 1976-10-29 |
Family
ID=24285689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO760329*[A NO760329L (de) | 1975-04-28 | 1976-02-02 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3954983A (de) |
| JP (1) | JPS51127100A (de) |
| BE (1) | BE839035A (de) |
| CA (1) | CA1049011A (de) |
| CH (1) | CH619237A5 (de) |
| DE (1) | DE2607570A1 (de) |
| DK (1) | DK140502B (de) |
| ES (1) | ES444925A1 (de) |
| FR (1) | FR2309229A1 (de) |
| GB (1) | GB1492163A (de) |
| IE (1) | IE42419B1 (de) |
| IL (1) | IL49102A (de) |
| NL (1) | NL7601321A (de) |
| NO (1) | NO760329L (de) |
| PH (1) | PH11476A (de) |
| SE (1) | SE7601209L (de) |
| ZA (1) | ZA76621B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9908752D0 (en) * | 1999-04-16 | 1999-06-09 | Bp Oil Int | Purification process |
| DE10041478A1 (de) * | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| US20030026830A1 (en) * | 2001-05-08 | 2003-02-06 | Thomas Lauterback | Transdermal therapeutic system for parkinson's disease inducing high plasma levels of rotigotine |
| US20030027793A1 (en) * | 2001-05-08 | 2003-02-06 | Thomas Lauterback | Transdermal treatment of parkinson's disease |
-
1975
- 1975-04-28 US US05/571,941 patent/US3954983A/en not_active Expired - Lifetime
-
1976
- 1976-02-02 NO NO760329*[A patent/NO760329L/no unknown
- 1976-02-03 ZA ZA621A patent/ZA76621B/xx unknown
- 1976-02-03 IE IE210/76A patent/IE42419B1/en unknown
- 1976-02-04 SE SE7601209A patent/SE7601209L/xx unknown
- 1976-02-04 DK DK45876AA patent/DK140502B/da unknown
- 1976-02-05 GB GB4487/76A patent/GB1492163A/en not_active Expired
- 1976-02-05 ES ES444925A patent/ES444925A1/es not_active Expired
- 1976-02-10 NL NL7601321A patent/NL7601321A/xx not_active Application Discontinuation
- 1976-02-13 PH PH18101A patent/PH11476A/en unknown
- 1976-02-19 CA CA76246112A patent/CA1049011A/en not_active Expired
- 1976-02-24 FR FR7605111A patent/FR2309229A1/fr active Granted
- 1976-02-25 IL IL49102A patent/IL49102A/xx unknown
- 1976-02-25 DE DE19762607570 patent/DE2607570A1/de not_active Withdrawn
- 1976-02-27 BE BE164728A patent/BE839035A/xx unknown
- 1976-02-27 CH CH245576A patent/CH619237A5/de not_active IP Right Cessation
- 1976-03-31 JP JP51034588A patent/JPS51127100A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK140502B (da) | 1979-09-17 |
| CA1049011A (en) | 1979-02-20 |
| PH11476A (en) | 1978-02-01 |
| FR2309229B1 (de) | 1978-11-10 |
| DE2607570A1 (de) | 1976-11-11 |
| IL49102A0 (en) | 1976-04-30 |
| ZA76621B (en) | 1977-01-26 |
| FR2309229A1 (fr) | 1976-11-26 |
| US3954983A (en) | 1976-05-04 |
| JPS51127100A (en) | 1976-11-05 |
| AU1080676A (en) | 1977-08-11 |
| NL7601321A (nl) | 1976-11-01 |
| IE42419B1 (en) | 1980-07-30 |
| CH619237A5 (de) | 1980-09-15 |
| BE839035A (fr) | 1976-06-16 |
| SE7601209L (sv) | 1976-10-29 |
| IL49102A (en) | 1978-07-31 |
| ES444925A1 (es) | 1977-04-16 |
| DK45876A (de) | 1976-10-29 |
| IE42419L (en) | 1976-10-28 |
| GB1492163A (en) | 1977-11-16 |
| DK140502C (de) | 1980-02-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20010022241A (ko) | 결정형 디벤조티아제핀 유도체 및 이것의항정신병제로서의 용도 | |
| JPS62142198A (ja) | 新規中間体 | |
| EP2880023A1 (de) | Griseofulvinderivate | |
| IL33473A (en) | History of 1,3-dihydro-5-phenyl-H2-thiano] E-2,3 [and] E-3,2 [-1,4-diazipin-2-one | |
| US3379729A (en) | Piperazinyldibenzothiepins | |
| JPS61249966A (ja) | ベンゾアゼピン誘導体 | |
| NO760329L (de) | ||
| US3726870A (en) | 10-carbamoyl-dibenzo(a,d)cyclohepta(1,4,6)trien-5-ones | |
| EP0001002B1 (de) | Indanamine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Präparate | |
| JP2013545760A (ja) | キノリン誘導体化合物、その製造方法およびそれを含む薬学組成物 | |
| US3467755A (en) | Compositions and methods for producing sedation and tranquilization with substituted 4,5,6,7- tetrahydro-4-oxindoles | |
| JP2815150B2 (ja) | 置換されたジベンゾシクロヘプテンイミン | |
| JPS6344749B2 (de) | ||
| US3359263A (en) | Nu-substituted-1-phenyl-2-aminopropanes | |
| US3452052A (en) | Certain 1-(2**1-benzofuranyl)-1-hydroxy-2-alkylamino or aralkylamino ethanes | |
| NO125534B (de) | ||
| HU184791B (en) | Process for preparing derivatives of tetrahydro-pyrid-4-yl-indole | |
| DK162989B (da) | Den (-)-enantiomere af 2-(4-chlorphenoxymethyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol eller et fysiologisk acceptabelt syreadditionssalt deraf, dens anvendelse til fremstilling af farmaceutiske praeparater med antimycotiske virkninger samt laegemiddel indeholdende den (-)-enantiomere | |
| US3047571A (en) | Derivatives of oxopiperidinyl phenthiazines | |
| MX2015001963A (es) | Formulaciones farmaceuticas que contienen derivados con 3-(4-cinamil-1-piperazinil)-amino de 3-formilrifamicinas sv y 3-formilrifamicina s y un proceso para su preparacion. | |
| EP0000693A1 (de) | Aminophenoxymethyl-2-morpholinderivate, ihre Herstellung und sie enthaltende Arzneimittel | |
| NO125385B (de) | ||
| US4278798A (en) | 1-Ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxonicotinic acid and esters thereof | |
| JPS6229428B2 (de) | ||
| NO760418L (de) |